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Dirty Boy!

By: JPHutton



John was a geek and he knew it. At 40 years old he still lived at home with his elderly mother and spent most of his time in his bedroom. At school and college John had been top of his class in everything, but his intelligence hadn't won him any friends. He always felt awkward around others and was a social leper. Now a grown man, he still had no real friends, just a few work colleagues who tolerated him, but that was about it. 

As for women, well they had always been absent from his life apart from his mother and a couple of aunties and a female cousin. He'd had 2 dates in his life, both of them disastrous, at college, a girl who spent as much time studying as John did and who also was a bit of a loner, had agreed to go to the cinema with him. She was no stunner, small, with her hair in bunches (even at 19) and wire rimmed spectacles. The night had gone from one calamity to the next until she had stormed off and John had been left alone in a café. The other date had been fixed online, just 5 years previous. He had joined an adult dating site, not just for those looking for love, but for those looking for casual sex. He had eventually met up with a woman in her late 20's and they had gone to the cinema again and afterwards she had taken him in her car to a quiet spot out of town. At that time John hoped he was going to lose his virginity in the back seat of her car. However when she started kissing him and grabbed his hand and put it on her tit, he had ejaculated immediately in his trousers. She noticed straight away and started to laugh and John had been so embarrassed he had left the car there and then and ran away like a 10 year old.

Now he went to work each day, came home, had his tea with his mother and then went to his bedroom. There he would indulge in his hobbies, painting war gaming figures or doing math puzzles. Once he knew his mother was safely tucked up in bed he would spend the last hour or so before he went to bed looking at porn on the internet. He often downloaded porn movies usually teen lesbians and would watch and jerk off into a tissue. There weren't many nights when he didn't finished his day wanking off to two 19 year old sluts licking each others pussies. Now at the age of 40, John had got masturbation down to a fine art. He could keep his cock hard for a long while, often bringing himself up to ejaculation point, but managing to control himself so he didn't cum too soon. This might go on for an hour until he would finally succumb and shoot his load into the tissue which then went straight down the toilet.

As far as he was concerned this was just how life was going to be and so be it, if the only thing he ever fucked was his hand then he might as well enjoy it and do it well, just like he did everything else.

But on a stormy night, life for John changed.

It was gone 11.00pm and John was in his bedroom sitting at his desk. His 70 year old mother had retired to her bedroom half an hour earlier and John was in safe time. His mother never knocked when she entered his bedroom and John didn't feel safe looking at porn whilst she was up and about. Now though he was in his element, on the wide PC screen in front of him 3 teenage sluts were enjoying each other's bodies. The camera zoomed in on a perfectly shaved pussy, being held open by red painted finger nails and the tongue of the blond girl that was licking it. John instinctively stuck his own tongue out and made a licking motion. The thumb of his right hand was gently massaging pre-cum into his swollen dick-head and John felt great. His mind was completely focussed on what he was watching and doing and thus he was completely oblivious to the storm that had come in from the coast. He caught the flash of lightning from the corner of his eye and the roll of thunder followed a few seconds later. John loved storms, but this was not the time to be watching it. The blond girl was now licking her friends arsehole and the screen was filled by the other girls' puckered hole and the tongue that was stabbing in and out of it. Oh how John wished that was his tongue and his hand moved up and down on his shaft just a bit quicker. 

The lightning came again followed more rapidly by the sound of it this time, the storm was getting closer, but so was the storm in his groin and he had no intention of stopping now.

The next flash of lightning was followed almost instantaneously by the thunder it created and the sound seemed to fill the house and though it made John look away from the screen for a few seconds, he was soon back. His eyes transfixed on the blond girls tits now that were being teased by the tongues of her two friends. John was panting slightly now and he was gripping his balls with his left hand and moving his right hand from the stem to the tip of his swollen cock. As he continued to jerk off there was another flash of light, more sustained this time, but John was now coming to the film's and his finale. As the screen filled with one girl squatting over the face of the blond one and squirting her cum all over her face, John let out a little grunt and released the load of spunk he had been harbouring for the past hour. At first it shot into the tissue that was held some inches from his cock and then as the initial load faded and it turned into a dribble, John brought the tissue closer and just held it underneath his leaking cock whilst he relaxed.

"Better?"

John swivelled round in horror, someone was in his bedroom. Barely 3 feet away stood his mother, arms folded, eyes wide and looking straight at his groin.

John felt the colour drain from him, he thought he was going to be sick or faint or have a heart attack. His mother had caught him playing with himself. He would never be able to look her in the face again, his life was over, he would never be able to put this little scene out of his mind and it would always haunt him, he knew it.

"The storm woke me up," she said calmly, "I came to see if you were okay, but you were too busy to notice."

John couldn't speak, he still sat there naked, he was still holding the wet tissue under his now very small limp cock and he felt unable to move or do anything.

His mother finally looked away from him, but didn't move to leave.

"Sorry," she said, "When I came in and saw what you were doing I should have left straight away, but something came over me and I wanted to watch. I'm sorry John."

John managed to control his breathing and forced himself to turn away from his mother. He reached down for his boxer shorts and pulled them on, then he stood up walked straight past his mother and into the bathroom, locking the door behind him. He was shaking as he dropped the tissue into the toilet and flushed it away. He sat down and felt like sobbing, but after a minute or so pulled himself together, took a deep breath, opened his bathroom door and walked back into his room. He had hoped his mother would have gone back to her own room, but instead she was sitting on his bed, still dressed in her long blue dressing gown.

She looked up with pity in her eyes, "Look John I'm sorry and there is nothing to be ashamed about, nothing I haven't seen before."

He was still speechless, why didn't she just go and leave him alone.

"I know that you are a lonely man John and you're not doing anything that I wouldn't expect of a single man your age," she continued, "I know you don't expect to be caught by your own mother but I'm sure it happens quite often especially with younger men."

"This is my room, you should allow me some privacy," John managed to say.

"I know and like I said I'm sorry I have embarrassed you, I should have walked away," his mother hesitated seemingly trying to find the right words, "..but when I saw your erect penis and saw you rubbing it, I couldn't move."

"Mother that is disgusting," John blurted out.

"I know son, I know, but it is true, I'm ashamed to say it, but I wanted to see you ejaculate."

John again had that sickly feeling and his legs felt wobbly. His own mother was talking about seeing his swollen cock and seeing his spunk shoot from it and it just didn't compute in John's head.

She stood up and walked towards the door.

She stopped and turned "I love you son, I don't want this to ruin our relationship."

She left the room, softly closing the door behind her.

John lay down, but sleep wouldn't come, over and over the pictures rolled around in his mind, his cock jerking in his hand, the white globules of spunk landing in the tissue, his mother's eyes fixed on his cock. But as he lay there, different thoughts entered his head and he felt his cock start to stiffen again. His mother had wanted to watch, had she enjoyed looking at his swollen cock, had it made her wet?

He tried to shake himself back to reality but he kept replaying her words over and over again "When I saw your erect penis and saw you rubbing it, I couldn't move........I wanted to watch John."

John's hand reached for his cock again and he started to rub himself again and in a flash of pure filth he was doing in front of his mother. As he pictured her in his mind watching, his cock swelled more than he had ever remembered before. Thinking about doing this in front of his elderly mother was making him more excited than he had ever been before and after just a few tosses with his hand, he was covering his sheets in spunk.

He immediately felt ashamed but at the same time there was something extremely horny about the whole thing.

The next morning John went down for breakfast. His mother was already in the kitchen and she handed him his usual cup of coffee. There was an awkward silence and then John said, 

"I'm sorry Mum, about last night, I didn't mean to snap, it's just that... well.."

"I know son, look I'm to blame, I shouldn't come into your room without knocking, I won't do it again. I still treat you like a little boy and you're a grown man now and you need your own space."

John smiled and reached out and touched his mothers' hand.

"I just feel embarrassed that you saw me like that," John said.

His mother half laughed, "Like I said nothing I haven't seen before, though admittedly not in that state, anyway I know it is natural for men to play with themselves, especially if they have no real sexual release. I don't want you to stop doing things that you enjoy and that are normal just because of me. I promise I'll never disturb you again."

John felt his mouth dry up as a question formulated in his brain,

"So why did you not go when you saw what I was doing?"

She was embarrassed now and she turned away from him.

She walked across to the fridge and put away the milk and turned back to him with a heavy sigh.

"John I'm 70 years old, your father died 6 years ago and was very ill for the 3 years before that. When I came in and saw you, something came over me which I haven't felt in 10 years. I may be old but I'm still a woman and when I saw you playing with your penis I felt weak and excited. I know you are my son and I know I shouldn't have watched, but it was too exciting to walk away and when you finally ejaculated, it was a wonderful thing to behold."

John felt his groin stirring as his mother talked, the thought of her watching was turning him on again. He felt his body go all tingly and for the first time ever he looked at his mother as a woman, a member of the opposite sex, someone with two tits and a pussy. Not just a pussy he had come from and tits he had suckled on, but a pussy he could lick and tits he could suck. His cock was fully hard now as he made out her shape under her dress. His mother had always been a slim lady and as he stared at her he had a mental picture of her coming out of the bathroom naked when he was a teenager. That day he had seen her small breasts and her hairy snatch, but it had done nothing for him, but now the thought of it filled him with lust.

"I was embarrassed last night Mum," he said, "but if you want to watch again, well I won't mind." There he had said it, for hours last night he had thought of ways to say it and discounted each one, but now it was out.

She smiled and said "You're a good son, but it was very naughty of me and I know you are trying to be nice, but I mustn't watch you again."

John's heart dropped, he was hoping she would say yes and they would end up in bed together. She might be 70 and it might be incest, but a cunt was a cunt and tits, however wrinkled they might be, were still tits.

He tried not to sound too disappointed "Okay Mum just thought I'd offer."

He left the kitchen and went and got ready for work and within thirty minutes he was on his way to the office.

All day John was unable to concentrate, what an idiot as if his mother would agree to sex, as if a woman who had cared for him for forty years was now going to leap into bed with him and let him fuck her. He now felt more embarrassed about what he had said in the kitchen than what had happened last night.

When he arrived home his mother had his tea waiting for him and they ate in silence. On the way home John had picked up a war gaming magazine and after his meal, he waved in front of his mother as he went to his room, as if to say this is what I'll be doing tonight.

John was half way through painting a French soldier from the Napoleonic era, when there was a soft knock on the door.

"Come in," he said.

His mother came in sheepishly.

"Are you okay?" she asked.

"Fine Mum, just got to get these soldiers done for the fair next month."

She took a few steps forward and admired the rows of French infantry on the gaming table. She turned back to him.

"Look I've been thinking about this alday," she said "I do want to watch you masturbate."

John felt that tingly feeling again.

"I know it is wrong," she continued, "And we mustn't do anything, but I would like to see your erect cock again and watch you ejaculate."

John's cock was already stirring.

"You can watch one of your movies on the computer and not look at me if you want, I just want to see you darling."

John didn't want to look at a computer screen, he wanted to see his Mum's face. He wanted to see her eyes bulge as she looked at his manhood.

Slowly he stood up and unfastened his trousers, he saw his mother gulp as he did so, they fell to the floor and his boxers soon followed. As his cock sprang out, his mother let out a little gasp. He sat back down in his chair and took his cock in his hand. Clear pre-cum was already running down his bell end and he saw his mother instinctively lick her lips. He slowly moved his hand up and down, pausing each time to collect some pre-cum on his thumb and rub it into his cock. After a few strokes, he collected another globule of pre-cum on his left thumb and raised it to his lips, licking it seductively off. His mother gasped again, louder this time. 

"Is that good?" he asked her.

She nodded and felt her way to the bed, her legs too weak to stand on. She sat herself down as he continued to stroke himself.

"Do you like watching your naughty little boy play with his cock?" he asked.

"Oh darling it's wonderful."

John stood up and walked towards his mother and stopped just a foot or so away from the bed. He pointed his cock at her as he wanked, he wanted her to see the amount of liquid seeping from him.

"Mum, show me your tits please?"

"John I mustn't that is too naughty," but her hand was already reaching for the buttons of her blouse. She unfastened them, never taking her eyes off his throbbing cock. She pulled her blouse open, reached behind herself and unclipped her bra. Her tits were small and drooped slightly and she had small nipples, but for John it was a fantastic sight.

"Oh Mum, your tits are lovely, can I touch them?"

"John you mustn't darling, we can't take this too far, just play with your willy and look."

John was disappointed, but then his mother stood and unhitched her skirt and it fell to her feet. She sat back down in her pale blue panties and then pulled them down too. Her body was not as wrinkly as he had expected and her puffy pussy lips were clearly visible past her pubic hair. She reached down and with both hands slightly opened her cunt, so he could see it.

It was too much and John felt his cum rising, he took one step forward and released his spunk. It flew through the air landing with a splosh onto his mother's belly and grey pubic hair. She let out a little yelp and John saw a finger disappear into her cunt. As his cock continued to jerk, she rapidly forced her finger in and out of herself until she let out another little gasp followed by a moan that seemed to come from deep within her. John watched transfixed as a small amount of liquid seeped from his mother's pussy and onto his bed. He stood there holding his now spent cock, as the stain spread around her and he knew that his mother had cum in front of him. He continued to wank his semi erect cock as he took in her body, knowing that this is how he always wanted to play with himself in future.

After what seemed an age with neither of them saying anything, she stood up and collected her clothes. She stepped forward and gave him a brief kiss.

"That was very, very naughty," she said "You can never tell anyone we did this, but I'm very happy we can please each other."

John reached out and grabbed his mother, he wanted to touch her, feel her, kiss her.

As his hand brushed her right tit, she pulled back.

"No darling, we can't go any further, I will watch you and you can look at me, but that is all." 

She turned and left and John was left alone.

He wanted to go after her, grab her and force her down and then fuck her, but he knew he couldn't and knew that he would have to make do with mutual masturbation.

He heard the shower come on and realised that his mother was washing away the evidence, his cock jerked back to life as he thought of joining her but she wouldn't allow it, she wasn't ready, not yet anyway. 

But who knows what might happen if she continued to watch?

Dirty Business



" Oh my God. "

Those words gave me away. I should have been able to suppress my reaction and retreat quietly out of the apartment and go some place where I could get a stiff drink to calm my nerves. But is was too late, they saw me. The only thing I could do was run in my room and lock the door. 

I tried to busy myself: first by staring at the same page of a book for five minutes, then I turned on the radio as loud as I could to drown out my thoughts. None of these things worked. 

Maybe what I saw was a fabrication. I was awfully tired that day, that's why I came home early. I didn't expect my roommate to be there, I thought he was still at work. I just came home, opened the door, took off my coat, loosened my tie and walked toward my bedroom. It was out of habit that I looked into his room, it was on the way. And his door was open. Usually if he was busy or, engaged, his door was closed; well, it should have been closed this time. . As I passed my roommates room, I peered in and saw… I saw him on top of a girl, humping her. 

Both parties were wearing shirts but no pants. It was all that skin that I noticed first. The girl's legs were raised in the air, naked hips were locked together in sexual gridlock. And that's when I noticed: There was my roommate Jude, fucking his own sister.

I tried to busy myself in my room to subdue the thoughts that I had. I flipped through some books and absent mindedly arranged objects on my nightstand. What I had seen was… it was disgusting. I mean I had known them both for a very long time. Jude and I met in grade school and his little sister Diane was always around. We grew up together and were like family. I guess that's what made it so appalling to me; the fact that it was like I caught my own brother and sister in that way. The whole thing, or at least what I knew of it, shamed me. And the betrayal of those two doing it with me around hurt so much. I had never felt so bad in my life.

I stayed in my room for several hours, trying to wait out Jude and Diane. I thought they might take my confinement as a cue to leave me alone for a while. Eventually I fell asleep but woke up as hunger got the best of me. It was quite late and I heard no sounds coming from the apartment. I opened my door a crack and peered out into the dark hall. I could see a light shining from underneath my roommate's door and I debated for a moment whether to venture out or not. Finally, I decided to make a quick dash to the kitchen, assemble some provisions and head back to my room. Unfortunately, there was no ready to eat food anywhere in our house and I had to settle upon cooking some soup over the stove. 

As I let the pot boil, I heard Jude's door open and the creaking of the wood floor make their way down the hall towards me. I hunched over the stove and stirred the soup, trying to make myself look busy, hoping whoever it was wouldn't disturb me. 

" Jake, man. " Jude called out from behind me in a subdued voice.

" What? " I answered harshly.

" What's going on, man? " he asked. 

I stared into the pot for a bit before I answered. " Just making something to eat. "

He sighed and must have moved, because the floor creaked again. " Look Jake. I know what you saw was pretty… um, pretty weird but… "

Turning around quickly, faced him down. " But what, huh? There is nothing you can say that will explain the fact that you… you, you were doing that with your… with Diane! I mean, that's just wrong, I can't tell you how wrong it is. I mean, there's laws against it because it's so fucking wrong! "

Jude swallowed and looked at me with sad eyes. Lowering his head, he used his feet to trace invisible lines in the floor. I turned around again and stared at my meal but I suddenly was hungry anymore. 

" Jake… you don't have to tell me how wrong it is. But, I mean, it just happened. Some things just happen and you try to fight them and you know they're wrong but there is nothing you can do. You have to understand, we didn't want this… I mean, I know it sounds awful, looks awful but really it's not that wrong. "

I couldn't take it anymore. I turned the stove off, dumped the soup in the sink and went to my bedroom.

The next day, as much as I tried to fight it, I couldn't stop thinking the previous night. What had earlier been a burning sense of anger in my chest, dropped down into my stomach and turned to an empty feeling of sadness. What they did was wrong. Moreover, for some reason I felt just as guilty as they were. It was a feeling that is still hard to explain but I felt as though what ever punishment they were to receive would not escape me as well. 

The three of us had grown up together from way back and had shared in that time a sort of sexual awakening that I always felt was quite normal. I can still remember the day I rushed to Jude's house with a adult video I had borrowed from a kid at school. We sat in his room and just stared at the tape while we waited for his parents to leave. As soon as they were safely down the street, we popped the thing in and were introduced to sex for the first time. It certainly wasn't the only time either: During more times than I could count we masturbated together and once and only once, we masturbated each other. I had never thought anything of that or any other instances. Rather, they were fond memories of growing up with a best friend. 

Because Diane was roughly 2 years younger than me, I felt she was of more a bratty little sister than a peer or sexual creature. She was always trying to tag along with Jude and I and we both spent a great deal of our time trying to shake her off of our tails. As we got older, Diane found her own friends in high school and we ran with different crowds. Still, she was like family and we regarded each other very well. There was one time I caught her undressing though: She was doing laundry and when I walked in on her, her shirt was above her head and her breasts were exposed. Diane never knew I was there because I quietly backed away. I remember feeling a little ashamed at the moment; I never thought of her in a sexual manner. 

Jude I had lived together for several years and were so comfortable with each other that living apart never really entered our minds. Well, I suppose I must speak for myself on that account. Diane, by coincidence, moved into the same neighborhood when she went to college and the three of hung out on a regular basis. 

I decided to walk home that day both to clear my head and kill time until Jude was at work. I no longer was quite as disgusted and alarmed as I had been but I still didn't want to confront either of them, knowing this situation wouldn't pass without an eventual conversation on the matter. But, I had no such luck.

As I walked up my street I could see Diane sitting on our stoop. For a second I thought about turning around and going somewhere else. But, I sucked in my chest and headed home. 

As I approached my building, Diane made no effort to get up. Instead, she reached into her pocket, pulled out a pack of cigarettes and placed one in her mouth. 

" Do you have a light? " she asked.

Reaching into my own pocket, I retrieved my lighter and held it up to her face. She leaned into the flame and brought her hands up to shield it from the wind. There was a brief brush of skin on my hand and I flinched. 

Diane looked up at me with an expression that said she was quite hurt by my reaction. I fumbled for my keys and opened the door.

" Jake, can I come in for a minute? "

I wanted to tell her no, but I couldn't bring myself to say it. She seemed just as pained as I was over this situation. I shrugged my shoulders and walked into the building, leaving the door open so she could follow. I marched up the steps with Diane trailing a short distance behind. Inside my apartment, we didn't say anything to each other for a long time.. As Diane sat on the couch, smoking another cigarette I put a pot of tea on. I poured two glasses and placed Diane's cup on the coffee table. I didn't sit down next her. Rather I just stood there and looked down at her. Her eyes were on the steam rising from the hot tea.

" Jake, I don't know if you talked to Jude or what he said. " She paused for a moment then it all came out in one long sentence. " But, it just happened, I don't really know how or remember when. We knew it was wrong. We… well, I feel dirty all the time but honestly… "

But honestly what? I wanted to know. That you like it? That you love to fuck your brother?

Diane looked up at me, tears were forming in her eyes. I think she knew what I was thinking. " It was both of us. I mean, we both, mutually, did it. Rather, have been doing it. For about a year now. It's just physical, that's all it is. I mean, there's nothing really to a purely physical relationships. It's just sex. "

I slammed the cup down hard on the table and started to pace the room. " Oh god Diane! Do you hear yourself? This is not some guy… it's you brother. Your brother! This is not something you are supposed to do with him. I mean, you guys are like family to me… it's so upsetting. I just, I just can't believe you would… with him…"

Diane got up and came over to me. She wrapped her arms around me and sobbed into my back. I felt bad: bad for her, bad for her brother, bad for me. I turned around and took her into my arms. 

" Diane… Diane? Why are you crying? " 

She wiped some tears away from her face. " I don't know Jake. I guess I'm just scared because we've been caught. I never really thought it would be you. Mom and Dad really… if they ever found out it would be all over. They would just drop dead!"

" If you know it's wrong then why do you do it? " I asked. " I just don't see how it could ever happen. "

" Jude and I… when you where away in Maryland last year. We were hanging out a lot. We've always been close, you know that. I didn't feel like going home that night and you know how sometimes we sleep in the same bed. We've done that since we were kids. I slept with you a lot of times too. " She looked up at me to see if I wanted to hear anymore. The thing is I did, out some curiosity I had. Hearing it was, well, turning me on a bit; enough to send the blood flowing into my dick.

" It was just fooling around at first. We were wrestling or whatever and then he kissed me. " Her eyes got really wide to convey the astonishment she must have had when it happened. " But I didn't stop him at all. It wasn't until he was actually in me that we both realized that it was wrong. Then, we didn't talk to each other for a long time. " I did remember that when I came back, Diane was mysteriously absent from the apartment for a while.

She continued. " When we did finally talk, we both needed someone to comfort us. But we couldn't go to you or… anyone. " I knew " anyone " was Mom and Dad. " I guess our comforting led to it again. After a couple times, it became natural… like we were sleeping with anyone else. "

Diane took a sip of her tea and that seemed to be the end of her story. I wasn't quite sure what she wanted exactly, but it seemed the whole point of this confession was that she ultimately wanted my approval. 

I played with the circumstances in my mind: Yes, I knew this while thing was wrong. But, if they weren't hurting anyone than who was I to deny them anything. And Diane's argument, most likely shared by her brother, that it was just casual sex made a little bit of sense. 

I took a deep breath, and fiddled with an unlit cigarette. " Well, it seems like you both know the consequences of your actions so I can't let you two plead temporary insanity. I suppose I can grow comfortable with this idea but it's really not up to me to decide what you two do. However, I don't want to be party to this lie, as so far as your parents go at least. And you have to at least acknowledge that this thing could turn really bad at any time… pregnancy for instance. "

" Well, I'm on the pill. " She said, her face relaxing a bit. 

" Yes, well, that's good. I just need to be more comfortable with this idea. " My erection was just not going away. " And I guess I could see how it could be a turn on, in ' dangerous sex ' sort of way. "

A broad smile appeared on her face. I could see that she was thinking Oh, a brother and sister fucking turns you on, eh?

" But perhaps we should treat this like any other relationship that Jude or I brings in to this apartment. Behind closed doors… Jude and I are close, but not close enough to flaunt our sex lives all over the apartment. Even if this is… a special circumstance. " The more permissive I allowed myself to be, the more turned on I was getting. The pre-cum filling my pants made me shift in my seat and I didn't want Diane to see the huge bulge in my crotch. 

" Oh Jake, thank you! This is great. I mean, I don't know if Jude and I are going to continue but your support is such a relief… for me anyway. Jude and I haven't really talked in a while. " Diane came over and gave me a big hug. By accident, she shifted all her weight to one knee that happened to be in my crouch. 

" Ow, Ow, Ow, Ow! " I let out. Diane drew back and I sort of raised my hips to shake of the pain. I smiled and mouthed " I'm alright " but Diane patted me on the crouch apologetically. Or rather, patted me right on my erection. I looked up and gave her a cheesy, embarrassed grin because I knew there was no way she couldn't have felt my bulge. 

" Well, well, " She said. " Looks you are accepting this situation pretty easily. " Diane was always known for her dry sense of humor. 

I crossed my legs and tried my best to play my little problem off by putting my arm over the back of the sofa and looking cool. But it just wasn't working. 

Diane knelt on the couch next to me and leaned forward a bit, trying to get a better look at my crouch. Once again, I shifted trying to avoid my the curious onlooker. Finally I blurted out. " Well, these things have a way of, uh, appearing at the most in opportune times. "

She leaned back and placed her hands on her lap. " Jake, you are doing us a favor by supporting us. I could do you a little favor too. If you want, it wouldn't be a big deal. What's a little help between friends when… "

" There is help between siblings. " I finished. She seemed to take this as consent and reached over my crossed leg and placed her hand in my crotch. I really wanted to stop this but I didn't. Yes, I knew this was going to complicate matters but I was never one to keep things simple. 

I spread my legs and Diane reached under me, gave my balls a gentle squeeze and ran her hand up the length of my shaft. I leaned forward to kiss her but she drew away and got up from the couch. I made an attempt to follow but only sleep of the edge on my seat and sat on the floor, reclining on the sofa. 

A warm smile developed on her face. She leaned in and with her free hand she palmed my face and leaned in to kiss me. I obliged and we passionately made out on the floor of the apartment. It was a heated exchang and getting hotter by the moment. We were exploring each other's bodies' underneath our clothes; I traced her spine down her back and slipped my hand into her pants, slowly caressing her ass. Diane cocked her head to the side, exposing her neck to my lips. I traced a line with my tongue from the back of her mouth. Again she pulled away and a string of saliva connected our lips. 

Crossing her arms, she pulled off her shirt. She was wearing a white bra made of nylon or some other smooth material. I could make out the dark circle of her aureoles. Reaching behind her, she undid her bra. Delicately, I slid my finger underneath one of the straps and slowly pulled it down over her shoulder. Her breasts were beautiful: Round and full and covered with smooth almond colored skin, slightly lighter than the rest of her body. I took one in the palm of my hand and rubbed my thumb over her nipple. She responded by arching her back toward me. I kissed her neck and then ran my tongue down until it was over her breast. Kissing her bosom, I felt no shame in what I was doing with her. 

She got up and undid her pants, pushing them down to her ankles and kicking them off. Diane stood before me naked and beautiful. She was good looking girl: she was full figured and round, with wide hips and meaty thighs. But she wasn't fat… No, she was a perfect woman. From the angle I was looking at her, with the light at her back, her silhouette was like staring up at an beautiful plump angel. Although she was twenty years old, there was a sensual pubescent quality to her form. This sight alone justified her brothers actions.

I pulled my shirt off and without getting up, I removed my pants. Sitting there naked, with my back leaning against the chair and full, hard erection in my crouch, I reached out and caressed Diane's smooth leg. I let a finger slide against her silky skin along her inner thigh until I felt the soft hair where her legs met. Gently, I brushed my finger along her sex being careful not to press on her too hard. 

She moved forward and crouched a little bit so that thighs straddled my face. I smelled the scent of her most intimate of places. Softly gripping her by the butt, I raised my head just enough to line up my mouth with her fleshy mound. My tongue left my mouth and licked along the crevice of her sex. Diane responded with a soft moan. Pressing my mouth closer and closer to her, I kissed her pussy passionately. I used my tongue to probe her and moist lips to suck her clit. She started to bounce a little… up and down and up and down on my face as she stroked the back of my head. Finally, I needed air and with a gasp I pulled my head back. 

Diane got down on the floor in front me and took my excited dick in her soft hand. Leaning forward, so that I could feel her hair on my thigh, she kissed the base of my cock. Then slowly, she kissed up its length until finally, she had its head in her mouth. She took it into her slowly and almost got the whole thing into her. But it wasn't blowjob she was interested in giving me; she merely meant to get my member wet and slippery. 

Squatting over me, with one hand on my shoulder and one hand holding my cock straight up, she positioned my dick at the entrance of her snatch. Then gently, she lowered herself on me. She was a little bit tight so it took awhile until I was all the way in her but eventually, her pussy firmly gripped my cock. 

At first she didn't do anything except look at me with a loving smile on her face. With me inside her, we kissed each other. Then slowly, she began to rock back and forth so that my cock wasn't so much going in and out but rather, rubbing around inside her. It felt so damn good to feel her warmth. 

We fucked but it wasn't fast and hard. No, it was slow and gentle as if we were both savoring each little sensation that we had. I could feel my dick swell and I knew an orgasm wasn't too far off. Diane must have been close as well because she was no longer kissing me: her fingernails dug into my back and head was cocked back, her eyes closed. Then she began to ride up and down a little bit, so that her breasts bounced. Her fucking was becoming hard and her nails felt like they puncturing my back. No matter… I was approaching an orgasm rapidly and could care less if she was breaking my skin. 

Diane started to moan but never got too loud. But I knew, the walls of her vagina were gently contracting around my cock. That was it for me as well: my cock started to spasm and an orgasm radiated out from my crotch and ran through my whole body. I shook with pleasure. 

We remained locked together until my dick became soft and both are bodies relazed. Diane slid off of me onto the floor and lay on her back. Regaining my composure, I realized the implications of our act. Diane must have also came to the same thought; she used her hands to cover her face but I couldn't tell if she was crying or what.




Dirty Business Pt. 01



To start this story I will need to fill you in on a little bit of back ground information. I'm Chris, I'm a submissive male my partner of two years knows about my submissiveness and we have been starting to play some games based on this. She is keeping me locked in chastity for brief periods, likes to stretch my balls tease and spank me but other than that our relationship is not very sexual. She used to suck my cock every now and then but that now has stopped. She is very keen to control my orgasms and thus has not let me cum for the last fourteen weeks.

I have always known my cock is at best of an average size measured from the top to the tip it is about a quarter of an inch under five inches this, as far as I was aware had never been a problem, but over the last few months it seemed to be the focus of her attention when teasing me. She got into the routine of getting my cock as hard as she could then measuring it pointing out at every opportunity that this Dicklet as she called it was small and totally inadequate.

One day last week after such a session with the tape measure she looked at me and declared four and a half inches that's the best I can get it to, that's no longer a dicklet and can no longer be counted as a cock at all, she had been on the internet and seen bigger clits so from now on that's what we shall call it your Man Clit. I disagreed and said It was nearer five than four inches but she just slapped my balls and told me she had measured it and that's what it was, a clit and it would be called that from now on.

Now that's the history out of the way I can tell you a bit more about the happening s of the last few days. Friday after work she told me after my shower I should put my cage on and that it would me on until she came back from her business trip to London on the Wednesday evening. 

Monday came far too quickly there had been no mention of my man clit and no reference to the fact that I was in my cage at all. We kissed goodbye at the door I left for work and she left for London At about ten o'clock I got a text form Lynne It said Hi her safely checked into the hotel ok how are you? I answer I was fine. The next time I looked a t my phone was in the evening after Id returned home from work I had five missed calls. The contents of which basically said that now I didn't have a penis to worry about would I be upset if she were to find one on as she put it a real man that she could get some real pleasure from one that would reach the places that needed reaching, one that would make her feel that she had been filled, one that would stretch her in ways my man clit was never going to do. I thought about it for a good hour or so then replied in a text that, until now I didn't realise it was a problem, that I only wanted her to be happy and if that's what it took then she should go for it. Almost straight away I got an answer, Just two kisses xx

I heard nothing more form Lynne until just before I went to bed at about midnight. She asked if I was still up I replied yes. She continued that she had got talking to a group of young men in the bar and had been telling them about my lack of size over the course of the evening they didn't believe how small my man clit was and she wanted me to send her a picture she could show them. She said if I would send one she would tell me where the spare key was and I could let myself out she said send one in the cage and then one out fully hard with the tape measure against it so they could see exactly how small it was as they didn't believe her. I did as she asked and sent the first picture Quickly found the key laid on the bed I stroked my cock put the tape against it and sent the picture.

About thirty minutes went by before I got another text she was clearly a little tipsy she said that it was by far the smallest little thing they had ever seen and wanted to show me exactly what a real man should look like. Two minutes passed and my phone went again it was a picture message it had been taken from under a table and showed four men sat with their cocks out of there trousers dangling soft between the legs. Two white and Two black it was not a very clear photo but it was clear enough to see that all Four cocks were bigger soft than mine was hard. One of the white guys looked to be very very big his cock head was hanging over the edge of the chair and had a big ring through the head. I asked her who took the picture and told her the ringed cock was the biggest thing I had ever seen. 

What seem like an age passed before her reply but it was probably only a few minutes my cock was rock hard and throbbing as I pressed the button on my phone. I read the text, it said in big letters. I hope this answers you question. I scrolled down to see the next picture again it was taken from under the table but this time it was a picture of Lynne crouched down with her legs wide open she was knickerless her big smooth pussy open and wet, it had clearly been played with by at least one of the men, her clit was stood to attention and I could clearly see pussy juice dripping from her open hole. In each hand she had a cock one black and one white they were both now very hard and both extremely big she was pouting like she was giving a big kiss and the text underneath read just three words.

Time for bed xx



Dirty Business Trip



Chapter 1: The Transsexual Hotel Encounter

"Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and her lips were painted a reddish-brown colour. As she looked at the card I watched the long dark lashes on her lids closely slowly over her huge, sparkling eyes. She slowly opened her eyes again, and reached for a box of cardboard cards sitting off beside her computer.

"Yes, Mr. James. I have your reservation here," her voice was low and gravely. She sounded like Demi Moore. I watched her as she punched a few keys on her computer, and I caught myself wondering what she looked like under the green business suit that all the hotel employees wore. "A non-smoking room," she confirmed, and went quickly about her business, printing off my receipt and getting my key card.

She stepped momentarily away from the counter, and I looked at her body. She wore a knee length dress, and underneath black stocking that showed incredible legs. I could feel myself rising in my pants, and pushed closer to the counter in hopes that no one would see the growing bulge in my pants.

"There you go. Room 327. An excellent view. I just need you to sign here indicating that you agree to the rates quoted," she said, pointing at a spot on my bill. She had long red nails and the ends of thin fingers. I imagined her fingers wrapping around the shaft of my hard penis, and gently stroking it. I quickly signed the paper, and tried to push the thought out of my head. I took my key, and let my briefcase fall down in front of me, hopefully covering what must have been a very apparent hard-on if anyone chose to look.

"Thank you very much," I said, smiling at the woman behind the counter. I looked down at her nametag, which was pinned on her amble bosom. "Chantal," said the nametag.

"You're welcome. Just let me know if there is anything that I can do to make your stay more enjoyable," she said, smiling back. Her teeth were perfect and white and straight, and her lips were full. I imagined those lips slowly moving over the head of my penis, and down the shaft until they had swallowed it whole. I could feel my penis pressing up against my briefcase, straining the fabric of my pants.

"Actually," I said, "I have never been in town before, and was looking for a nice place to eat. Could you make any recommendations?"

"There is an excellent sea food restaurant over on Williams, but it's hard to explain how to get there. Listen," she said, leaning closer to me which caused my penis to nearly burst the zipper on my slacks, "I get off in half an hour. If you would like, I could take you there. It's on my way home, so it would actually help me out."

"Yeah, great," I stammered. I could feel the tip of my penis moistening my underpants.

"Excellent. I will meet you in the lobby at 6:15?" She asked. I nodded, thanked her, and ran to my room. I threw my suitcase and briefcase on the bed, whipped open my slacks, and whacked off. My penis was so hard when I touched it, and it took only about 40 seconds until my come was splattering the sink in my bathroom. I can't believe how horny I had been. I collapsed on the bed, and calmed down listening to the radio.

At 6:15, I proceeded down to the lobby, and found Chantal standing by the door. She was still wearing her green dress, but she had taken off the accompanying green jacket and scarf to reveal a white cotton blouse, which had two buttons undone.

"Ready?" she asked, as she bent over to pick up her purse. Her shirt fell open slightly, and I caught a view of her breasts nearly bursting out of a red lacy bra. I could feel my penis start to rise in my pants again.

The restaurant was fairly difficult to get to, and when I pulled into the parking lot, I was concerned that I would have a tough time finding my way back to the hotel. "Chantal, is there an easy way to get back to the hotel from here?"

"You just go back the way you came," she said. I gulped.

"Listen, I don't think I remember how I got here. Let me make you an offer. Why don't you join me for dinner, and afterwards I can give you a lift home and you can give me directions to the hotel. How does that sound?"

Chantal smiled, and pushed her hand through her shoulder-length dark hair. "Alright, Mr. James. Those terms sound agreeable to me."

"Please, call me Alan."

Dinner was excellent. The food was spectacular, just as Chantal had promised. Chantal and I had an excellent conversation. Chantal was working at the hotel until January, when she was going back to school for architecture. As I was in construction, we had an excellent discussion about the business. The conversation was so good that I almost forgot that I was completely turned on by Chantal, and was only reminded when she would lean forward and I would catch a glimpse of her red, lacy bra.

After dinner, as we walked back to my car, Chantal made me an offer that caused my penis to stand straight up in my pants. "Alan, I know that our original deal was for you to drop me off at my house after dinner, however, I would really like to go back to your hotel room, if you don't mind."

I had never been approached so forwardly by a woman before, and I must say, I really liked it. "Of course I don't mind!" I said, and nearly ran to the car. On the way back to the hotel, Chantal's hand caressed my leg, running from my knee up to just below my crotch, and running back down again. My hard-on was larger than ever. Chantal wanted to go through the back entrance, because she was concerned about her co-workers seeing her.

"It's frowned upon for the staff to sleep with the guests," she explained. We went up the stairs to my room, and I put the chain on the door and the "do not disturb" sign on the door.

Once the door was locked Chantal pulled me close to her, and she ran her hands over my chest. I grabbed one of her hands, and pulled it up to my mouth. Her hands were almost the same size as mine. I sucked on her first finger, and she tilted her head back and let out a soft moan.

She pulled her finger out of my mouth, and started undoing the buttons on my shirt. I stepped back so I could look her over as she worked on getting me undressed. She was only about an inch shorter than me, but much skinner. I would guess that her waist was probably about 26 inches around, and her hips were not much larger than that. Her breasts, though, were quite large, and I moved my hand over to her shirt and undid the next button on her blouse. Her blouse fell open, and I could finally get a good look at her breasts and the red bra.

"Do you like them?" Chantal asked. "I had them done. I could have gone back to school two years ago if I hadn't had my breasts enlarged, but I feel so much more confident and sexy since the operation."

"I think that the doctor who did them should get an award." I cupped her breasts in my hands. They were firm, and her nipples were jutting at the material on her bra. I bent down and kissed the top of her breasts. The bra was a front clasp bra, so I undid the clasps and let the bra fall away. Her nipples were large and dark, and they had become hard with excitement. I took her left breast in my mouth, and let my tongue roll around her nipple. Once again, I heard her let out a soft moan.

Chantal was done undoing my shirt, and her hands moved up over my stomach and chest, and down my arms, pushing the shirt off with them. I let my arms hang at my side, and the shirt fell to the floor. Chantal's strong hands then moved back down my chest and stomach, and found the buckle on my belt. Soon she had undone my belt, the top button on my pants and my fly, and her hand was inside my shorts, rubbing my hard cock through my underwear. I moaned, and pushed myself hard against her hand. She wrapped her fingers around the shaft of my cock, and slowly stroked it.

I continued to suck and lick her nipple. She squeezed my penis, causing me to shutter. I took her nipple gently between my teeth, and pulled back slightly. Her hand released, and then grabbed my penis even harder. My pants slid down my legs to the floor and I stepped out of them. Chantal continued to rub my penis through my underwear, and I continued to lick and nibble on her breasts.

Chantal pulled away from me, turned around and walked towards the bed. She removed her shirt and bra, and I could see her naked back. Then she reached behind her, and unzipped her skirt. It feel to the floor, revealing a red pair of thong bikinis and black stocking that went up to her thighs. She lay down on the bed on her stomach and pushed herself up on my elbows. "Do you like my ass? Why don't you come over here and show me how much you like it."

I walked to the bed, lay perpendicular to Chantal and let my face hover right above her ass. I kissed one cheek, and then the other. I moved my hand up to slip off her thong, but she quickly turned over. "Mmm, not just yet," she said, and kept her legs tightly closed. "Why don't you lie back?" she asked.

I lay back, and Chantal removed my underwear. My penis sprung up at the feeling of air against it. Chantal blew on the tip of my penis, which caused it to jerk. She let her tongue roll down the shaft, and gently took my left ball in her mouth. She sucked on it for a moment, and then shifted over and sucked on the right ball. She then ran her tongue back up the shaft of my penis, and put her lips on the head of my penis.

Her mouth moved up and down the shaft while her hand massaged my balls. I raised my hips, pushing my cock deeper inside her mouth. Her hand slid down from my balls, and traced the crack of my ass. Her finger found my asshole, and pushed gently against it. My ass clenched around the tip of her finger, and my cock jerked stiff. I was washed with a fantastic felling, and let out a loud moan. Her finger pulled out of my ass, and her mouth pulled off my penis.

Chantal lifted my legs, and pushed them up in the air and back towards my head. My ass opened up, and Chantal's tongue pushed into my asshole. I had never had anyone do this before, and the sensation caused my penis to jerk violently against my stomach. I felt as if I was going to shoot right there on the spot. Chantal's tongue worked in and out of my asshole. I pushed myself against her face, wanting her tongue to dig deeper and deeper inside me. "Oh God. That's fantastic!" I said. Chantal responded, but I couldn't understand what she said with her face buried in my ass.

Chantal continued to lick my ass, and I couldn't take it anymore. "I am going to explode!" I said. I reached down and started to stroke myself. Chantal's tongue stopped penetrating me, and she moved up and took my penis in her mouth again. My hand fell away from my cock. She pushed up and down the shaft twice, and then pulled away from my cock. She looked at me with a bizarre look on her face, like a child about to get into trouble, and licked her first finger. She then moved back down on my cock with her mouth. I closed my eyes and let her expert mouth work my cock.

Suddenly, I felt something pushing against my asshole. Her finger entered me, and I was so surprised and turned on that I came without warning. Chantal took two shots in her mouth, and then pulled off and the rest of my powerful come shoot far up my stomach and chest. I had never blown my load so forcefully and for such distance before! Chantal let my come dribble out of her mouth and onto my cock. "My, my," she said. "You certainly were ready for that!" Her finger pulled out of me, and I lay back exhausted.

Chantal got up, and walked into the bathroom. When she came back she was carrying a face cloth which she had wet. She ran the face cloth over my chest, stomach and cock, cleaning up the come which covered my torso. "You really liked that, I guess?" she asked.

"You need to ask?" I replied. I sat up and kissed her mouth. Our tongues explored each other's mouth. She ran her fingers through my hair. I let my hands slip down her back, and along the outside of her thighs. Once I reached her knees, I ran my hands back up the inside of her thighs. She closed her legs tightly. "Not yet. Let's give you some time to regenerate," she said. So we continued kissing for about 20 minutes, while my soft penis started to grow. In 20 minutes it was as hard as a rock again. "Now it looks like your ready for me," Chantal said, and stood up.

She pulled my head to her flat, tanned stomach, and I kissed it. While I was kissing her stomach, her hands reached down and adjusted her bikini briefs. I pulled away from her stomach, and looked down at her thong. There was an obvious bulge between her legs.

"Oh my God! You have a cock!" I cried.

"Mmm, yeah," Chantal said, tracing the outline of her large cock with her finger. She slowly rubbed her cock through the fabric of her bikini, and it started to grow. "Does it bother you that I have a cock?"

"I don't know," I said, and I didn't. I certainly didn't expect this, and I had never thought before of having sex with a shemale. Chantal was such a beautiful and sexy woman, it had never even occurred to me that she might be a man. I have seen shemale prostitutes working in downtown before, but they had never looked like this! Those shemales looked like men in women's dresses. Chantal looked like a woman – a beautiful woman. She just happened to have a cock.

"No one has to know, if that's what you are concerned about," she offered. I hadn't even thought about what other people would think if they found out about this. I was still dealing with the shock that I hadn't realized. I always thought myself a pretty observant guy, but I completely missed this one. 

"No, no. That's not a problem," I said.

"So, do you want to continue?" she asked. I wasn't sure. Chantal reached down between my legs and grabbed my cock, which was still rock hard. "It certainly seems like your little head has made its decision."

I leaned forward, and kissed her stomach again. I let my tongue trace down her stomach, through her belly button and over the fabric of her thong. I took her semi-hard penis in my mouth through her underwear, and ran up and down the shaft. It started to grow in my mouth. Chantal pulled back, and slipped her underwear off.

There it was, completely naked – a penis, dark, long and hard. The hair around the base of the penis had been completely shaved off. Chantal was circumcised, and the skin around the tip was darker than the rest. She swung around and lay down beside me on the bed.

I looked at her, from head to toe. Her beautiful, feminine face. Her large, bulbous breasts. Her flat stomach. Her long legs, covered with black stocking. And between her legs, an increasing long and hard cock. "Yes," I decided. "She is still beautiful, and I am still turned on by her."

I don't know if I am gay, or straight, or bisexual. I have never been turned on by a man, and have never thought before of transsexuals. But that night, in the hotel room, it all made sense. I lowered my mouth onto her penis, and started sucking. 

I don't think I was very good at first, but Chantal provided direction. "That's it. Good. Open your teeth a bit, you don't want to scrape the penis. Yes, Yes. Try going farther down the shaft. That's it. Breathe through your nose. Mmmm. Yes. Now take my balls in your mouth. Ow, ow. No gently. Gently. Yes. Yes. That's it. Lick the shaft. Yes. Now lick the head of the penis. Mmmmm. Run your tongue around the tip. Yes, that's it. That's it." Eventually I got the hang of it, and Chantal's directions were replaced with a serious of moans and grunts. 

After about 5 minutes of sucking and licking, Chantal asked, "Would you be interested in tasting my come?" 

"I don't know. What does it taste like?"

"It's both sweet and tart, like eating a lemon and sugar at the same time," she said. "You don't have to swallow if you don't like the taste."

"Okay," I said. The only time I had tasted come before was when there was residue left on the lips or in the pussy of a lover. And I don't recall being adverse to the taste then. 

"Alright. Put your mouth over the tip of my cock," she said. She took the shaft of her cock with her fist, and started pumping up and down. I kept my mouth over the head of her cock, and used my tongue to flick at the tip. 

She came quickly, grabbing my head and pushing it down over her cock and the come hit the back of my mouth. The initial taste was sweet, but it caused my lips to pucker. I let the come slide down my throat, and swallowed it all.

"Oh, you decided to swallow. You are going to be very popular with my friends," she said. I hadn't thought to that point what this meant past this night. However, that comment got me thinking about what I wanted from a relationship. I've had a number of relationships with woman, and they never seem to turn out the way I want them to. I can never get close, emotionally or mentally to a woman. Maybe my answer was here. Maybe I needed a woman who knew (at least partially) what it is like to be a man. Maybe I should start dating transsexuals full time.

Of course, I was jumping ahead of myself. Chantal brought me back into the moment by kissing me on the lips. We kissed deeply. I lay back on the bed, and Chantal crawled on top of me. After 5 or 10 minutes of kissing, I could feel Chantal's cock starting to grow again. Soon our hard cocks were brushing up against one another. I grabbed her hips and pulled her against me. I started humping against her cock. 

"You're moving like a bucking bronco!" she exclaimed. "You seem like you are ready to fuck." Chantal pulled herself off me, and lay on her back by the side of the bed. "Get off the bed and kneel between my legs," she said. I knelt down, and my cock lined up perfectly with her ass. Chantal's hands grabbed my cock, and slathered it with jelly. Chantal had reached behind her and grabbed a jar of KY out of her purse. "This will help you enter me," she explained.

With Chantal's guidance, I pushed my cock into her ass. It gripped my cock tightly, and was warm. I pushed slowly at first, but then Chantal started urging me to fuck faster. I started pumping faster, and faster. Chantal started moaning. I cock slipped in and out of her ass, my balls slapping up against her butt cheeks. Chantal reached down and started playing with her cock, keeping it hard and erect.

It didn't take long before I was shooting my load into Chantal's ass. I pulled my shrinking penis out of Chantal, and looked as my come dripped from her beautiful asshole. "I want you to put your tongue in there and clean me out," Chantal said.

"What?"

"Lick me. Drink your come from my ass. Fuck me with your tongue!" So I licked the come that was running down the crack of her ass, and then started slurping and licking the asshole itself. At first, it was juicy with come, and the slightest touch caused it to come cascading out into my mouth. But soon I had to push my tongue deeper and deeper inside Chantal to taste the come. Chantal pushed against my face.

I could smell Chantal's balls as I licked her, and I longed to have her cock in my mouth again. I watched Chantal's cock get harder and harder, and soon I couldn't take it anymore. I abandoned her asshole, and wholeheartedly pumped my face up and down on her penis. This time, Chantal didn't need to provide any direction. She simply let me work her cock, balls and asshole with my mouth. After another 10 minutes of my tongue treatment, Chantal came and I swallowed every last drop.

That was the end of my sexual adventure for that night. Chantal and I held each other and kissed until we fell asleep in each other's arms. The next morning we both awoke with hard cocks, and once again pleased each other. I stayed at that hotel for a week, and in that week not only meet Chantal, but her two transsexual roommates as well, and the four of us experienced some of the most pleasurable sex I have ever had.




Dirty Business Trip



I have returned home now, and am still deciding what to do about my new found love of the transsexual form. As I said, I am not sure if that week out of town makes me gay, or if I am still straight. However, last night I was at a bar, and talking to a woman, and I must tell you, that I kept hoping that if I got her home, she would slip out of her dress and I would discover a thick cock between her legs.

Chapter 2: The Bungalow

My name is Alan James. I work at a large restaurant chain in their construction division. I spend my time co-ordinating the construction and remodelling of the stores in our chain. Part of my job includes travelling to locations where restaurants are being built, and ensuring that nothing goes wrong.

I was recently in another town, and on my first night in town I hooked up with Chantal, the woman who worked behind the counter. She was an aspiring architect, and so we discussed the construction industry at length over dinner. After dinner, we went back to my hotel, and after some very hot and heavy foreplay, she peeled off her panties and revealed a great, big cock. I had never been with a transsexual before, but the experience was out of this world. And that was only my first night in town.

The next day I was at the construction site, but was distracted all day by the thought of Chantal and her rock hard cock in my mouth. It was tough trying to keep my mind on the job that day, but I did it and returned back to my hotel at 7:30pm that night. My message light was flashing.

"Hi Alan, it's Chantal," the gravely voice on my voice mail said. "I got off at 6 o'clock, and was disappointed that you weren't in your room. I would really like to see you again tonight. Why don't you give me a call at home." I quickly grabbed a pen and copied down the phone number that she gave me. My penis stiffened in my pants as I dialled the number.

"Hello," the voice on the other end of the receiver said.

"Uh, yeah. Hi. Is Chantal there?" I asked. I think I was having trouble putting together words correctly because all the blood had flowed from my brain and into my now solid cock.

"Just a minute," the voice said, and I heard the phone hit the desk. I sat on my bed waiting for Chantal to come to the phone, rubbing my cock through my pants. I so much wanted to break out my cock and whack off, but I didn't want to waste any of my sexual energy on solo adventures if I could be spending it with Chantal. Finally Chantal picked up the phone. I told her who it was, and she wasted no time in inviting me over. I copied down the directions to her house, grabbed my coat and sprinted out the door.

I must have been quite a sight, standing at the door of the bungalow with my cock straining 6 inches out in front of me, trying to pierce through my pants. Chantal opened the door, and she was wearing nothing but a baby-blue teddy and thigh high stockings. She raised her arms and ran her hands through her shoulder-length brown hair. Her arms raising caused the teddy to ride up just a touch, and I caught a glimpse of her cock and balls underneath. My own penis was about to pop open my fly. Chantal looked down at my pants. "I see you are about to explode. Let's get you inside and naked."

As soon as I was inside and the door was closed, Chantal was undoing my belt. Soon, my pants and underwear were lying at the front door as we made our way into the living room. The living room was dimly lit by candles, which danced light on the walls and the various painting of nudes by the great masters (obviously, they were prints). I peeled off my shirt, and took my place on the couch beside Chantal. We started kissing as she rubbed my cock.

She lay me back on the couch, and swung around so that we were positioned to perform a 69. She took my cock in her mouth as I pulled the teddy up slightly and revealed her cock and balls hanging between her beautiful, tanned legs. I lifted my head slightly, and took both her balls and cock in my mouth at the same time. I started working them with my tongue, and only released them once her penis had started to grow, and forced me to choose between either it or her balls.

Chantal pumped her mouth up and down on my penis, while her hands stroked down from my balls to the crack of my ass, and back up again. I took her erect shaft in my mouth, and sucked hungrily on it. Last night was the first night I had ever tasted come, and I was hungry to taste it again.

I came quickly, spraying my load into Chantal's mouth. She swallowed my offering, and then sat up, pivoting her hips so that her asshole was positioned above my mouth. I stuck out my tongue, and started penetrating her hole while she stroke herself off. My tongue moved in and hot of her wet hole, and soon Chantal was pumping furiously at her own cock. She started moving her ass up and down on my face, and groaned loudly as she ejaculated all over my chest. I pushed myself down the couch a touch so I could catch the last few drops of her come and lick her penis of the white juice. Chantal lay back in the corner of the couch and softly stroked her nipples under her teddy. 

"I wish you had warned me you were going to come," I said. "I really wanted to taste it again."

"Mmmm," Chantal moaned, her eyes closed as she played with her left breast and cock. "Don't worry, you will have plenty opportunity for that tonight." I crawled over to the corner of the couch, and placed my lips against Chantal's. Her tongue flirted out of her mouth, and roamed the inside of my mouth.

We were kissing so intently that I didn't hear anyone enter the room. The first indication that I had we were not alone was when a pair of hands stroke my head. At first I thought it was Chantal, but I could feel Chantal's hands on my hips, pulling me close to her. I broke off the kiss, and pulled myself away from Chantal.

Standing behind Chantal was a tall blond with hair down to her shoulder blades. She had blue eyes and pale skin. She was wearing a red sweater that matched the colour of her lipstick and tight black riding pants. She placed her hands on Chantal's shoulders, and than ran them down into the top of her teddy, using her first finger to circle Chantal's nipples.

"I would like to introduce one of my roommates," Chantal said, smiling devilishly. "This is Rebecca. I believe that you talked to her on the phone earlier this evening."

"Hello Alan. Chantal told me all about your adventure last night. She told me that you have quite a tongue for exploring." Rebecca moved from behind Chantal and came around in front of the couch. I could see through her tight pants that she had a bulge growing between her legs. She walked up in front of me, grabbed my hands and placed them on her slim hips. "Tell me, would you like to explore this territory too?"

I looked over at Chantal. I wasn't sure how she would take this. Would she be jealous? But Chantal was smiling. "Go ahead. I bet the three of us could have an excellent time together."

I let my hands explore Rebecca's hips, than pushed them back and caressed her ass. I moved my hands up her back and underneath her sweater, feeling her smooth skin. "Ohhhh," she moaned. "You have such a soft touch." My hands moved around her sides and found her stomach, which was flat and soft. I moved my hands down towards the waist of her pants. I pushed my fingers inside her pants, and slowly started to pull them down. I pulled her pants down past her hips and then past her cock, which sprung out from between her legs. She had shaved all around her penis expect for a small triangle above her cock. I pulled her pants down past her knees, and Rebecca stepped out of them.

I kissed the inside of her leg, just above her knee, and ran my tongue up the side of her leg until I was about 2 inches from her crotch. Then I kissed the inside of her other leg, and repeat the action. I moved up above her cock, and kissed her just above her pubic hair. Rebecca grabbed my head and pulled me close to her. Her cock pressed up against my throat. It was hard and hot. I moved my head down just a bit, and took it in my mouth. I started by sucking the tip, pulling my mouth off and licking the head, and then sucking on the tip again. Soon Rebecca couldn't take the teasing any more, and when I put my mouth back on the shaft, she pushed my head all the way down her cock. I gladly accepted her full length, and started pumping up and down on her shaft.

Chantal got up off the couch, and walked around behind Rebecca. She knelt down, and slowly started licking the crack of Rebecca's ass. Rebecca, torn between the two sensations, pulsed her hips back and forth, alternately pushed deeper into my mouth and pushing harder against Chantal's face. Chantal firmly gripped Rebecca's ass cheeks, and pulled them apart, revealing Rebecca's tight hole. Chantal extended her tongue out as far as she could, and pushed it deep into Rebecca's ass. Rebecca moaned loudly, and pushed back, pulling her cock right out of my mouth.

I watched for a moment as Rebecca, her eyes closed and mouth agape wriggled her butt against Chantal's face, who was growing harder and harder by the moment. My own cock was starting to grow hard again, and my craving to taste come was mounting, so I took Rebecca's cock in my mouth again, and started pumping even harder. Between my mouth and Chantal's tongue, Rebecca couldn't hold out for long and soon she come hard into my mouth. Rebecca nearly screamed as she came and once she was done, she fell onto the couch beside me. Chantal, smiling and hard as a rock, took a seat on the other side of me.

The three of us sat on the couch – me completely naked, Rebecca naked from the waist down but still wearing her red sweater and Chantal in her baby-blue teddy and stockings. We didn't say a word, just breathed heavily and smiled at the thought of the ecstasy that we had all just taken part in. But I couldn't sit still for long. I had a fully erect penis between my legs that needed to be released, and two beautiful shemales to help.

Chantal could obviously see I was ready to go again, so she bent over and started to lick my nipples. They soon grow hard like pebbles, and Chantal's hand ran over my stomach and down to my cock. She rubbed her hand up and down on my crotch, causing my penis to rub up and down against my inner thigh. With my left hand I reached down between her legs and took her penis in my hands. With my right hand I reached around behind her, and let my hand rub up and down her back.

Chantal broke off from my nipples, and started kissing up my chest. Her tongue ran around my Adam's apple as her hand took a firm grip of my cock. I started pumping her penis with my left hand. My right hand creeped farther down her back until my finger was exploring the top of her ass.

Chantal's lips reached mine. Our hands stroked each other's cocks. Chantal repositioned herself so that she was straddling me, allowing my finger to slip even farther down her ass crack until it was pressing against her asshole. Chantal started to stroke my penis harder as I pushed my finger into her ass. We continued to stroke each other and kiss deeply as I finger fucked the beautiful, tanned shemale.

I could feel the come rising to the tip of my penis. My hips jerked up and down and I pushed my finger deeper into Chantal. She pushed back against my hand and pumped my penis furiously. I started stroking her faster, and she responded by pushing her hips back and forth, moving my finger in and out of her ass, and doubling the stroking action of my left hand. My come flowed from my cock and in the throws of orgasm I squeezed Chantal's penis. She yelped and pulled back. As I released her cock from my hand, her white juice jetted out onto my chest. Chantal made circles with her hips and pushed back against my finger as my come soaked my chest. She kissed me softly. 

"I am sorry if I squeezed you too hard," I apologised.

"Oh, it didn't really hurt. I was just surprised. Anyway, the shock of the event made my shoot quite fiercely."

Rebecca was sitting beside us on the couch, smiling and getting hard again. She sat up straight, stuck out her chest and pulled the red sweater off her torso. Her skin was white and smooth and her breasts were small and firm with a small, light red nipple. I moved over to the other side of Rebecca, and took her breast in my mouth. Chantal moved closer to Rebecca, and took Rebecca's other breast in her mouth. Chantal and I sucked on Rebecca's tits as Rebecca lay back and rubber her crotch.

Chantal tapped me on the shoulder, and pointed down at Rebecca's hard penis. Chantal moved down and took the penis in her mouth, enveloping it fully once, and then pulling off. I did the same, opening my mouth as wide as I could, and pushing Rebecca's cock as far back in my throat as it would go. We continued tag-teaming Rebecca's cock for the next few minutes, each sucking it for a few seconds, and then letting the other take over.

"Mmm, that feels so good," Rebecca moaned. "But you two have to speed up. My cock is getting ready to explode, and if it doesn't soon I am going to have a serious case of blue balls." I nearly laughed at the thought of this beautiful, alabaster-skinned blond having blue balls.

Chantal took Rebecca's penis in her mouth. I slide off the couch, and positioned myself between Rebecca's legs, and started sucking on her balls. Chantal moved up and down on Rebecca's cock as I licked underneath Rebecca's ball sack.

"Do you like that?" Chantal asked Rebecca, who moaned a positive response. "Would you like even more to fuck me?" Chantal asked. Rebecca nodded.

Chantal got on all fours on the couch and pulled her teddy up over her hips, revealing her firm tanned ass. Rebecca knelt behind her, and worked Chantal's ass with her tongue, getting it moist. Once Chantal's hole was lubed up with Rebecca's spit, Rebecca pulled herself close to Chantal, and pushed her cock into Chantal's ass.

I watched for a few moments as a beautiful blond fucked the tanned brunette in the ass. Rebecca started pushing harder and she bent over Chantal's back. I looked at Rebecca's ass, which had opened up slightly. I moved in behind Rebecca and started licking and sucking the beautiful puckered hole between her ass cheeks. Soon the hole was wet, and had opened up wide in anticipation. I grabbed my hard cock and pushed it inside Rebecca's ass.

The three of us formed a doggie-style Conga fuck line. Chantal received from Rebecca, who was getting it from me. Soon we had a fluid motion of pushing in and out going, and the girls were moaning furiously. My cock pushed in against Rebecca's closing and opening ass and the inside of her ass was warm. I can't believe how great it felt to fuck someone's ass. It was much better than any pussy I had ever been in. It was tighter and warmer, and the action of Rebecca's sphincter closing and opening on the base of my penis heightened the pleasure.

Rebecca came first. Chantal pulled away, white come dripping out of her ass. Chantal stood up and walked around to the other side of the room, so she could watch as I pumped in and out of Rebecca. Rebecca, now free to concentrate on my penis in her, started moving her hips side to side. With the added motion, it didn't take long for me to come in Rebecca's ass. I bucked up, nearly bending over backwards in an attempt to bury myself deeper inside Rebecca as my come spilled out inside her.

We were done for the night. Chantal went to get us some water as Rebecca and I relaxed on the couch.

"You were excellent for only a second time. Are you sure you haven't sucked a cock before?" Rebecca asked.

"No. I guess I just have received enough blow jobs that I know what works and what doesn't work. I think that's one of the great things about being with you and Chantal. I have never been with women before who knew how well to please a cock. Obviously, you and Chantal would know what it takes to please a cock because you have one."

Rebecca laughed. The conversation turned from sex talk to small talk. Rebecca was a interior decorator, and we discussed the design of restaurants until Chantal returned to the room. Rebecca took a sip of her water, and then got up to leave. "I had a great time tonight. Alan, I would like to continue our discussion some time about design. How long are you in town for?"

"Just until Friday," I said. Suddenly I regretted the fact that I couldn't stay in town longer, and continue to see these two intelligent and sexy shemales.

"Where are you working?" Rebecca asked.

"Down at 8th and South line."

"I have a client that I have to see tomorrow on 8th and Renard. That's just 4 blocks away. My appointment is at 11 o'clock. I should be finished up by noon. Would you like to grab some lunch?" Rebecca asked. She was still completely naked, her cock soft between her legs. What an odd scene, I thought.

"Okay. Just pop by the construction site. I will be in the trailer."

Chantal and I finished our glasses of water, and got dressed. I put on the clothes that I had worn to the house. Chantal changed out of her blue teddy, and put on a casual white summer dress that highlighted her excellent tan. "Are you hungry?" she asked, and I realized that I hadn't eaten since 1 o'clock in the afternoon, and it was already after 9pm. 

"Yes. After all that activity, I am starving." Chantal prepared some pasta, and we sat down in the dining room and had a wonderful conversation about our favourite architects. 

After dinner, we proceeded up to Chantal's bedroom. Chantal stripped off her summer dress and stood naked before me. I pulled off all my clothes, and we embraced. I lay back on the bed, and Chantal climbed on top of me. She took both our penises in her hand, and stroked them against each other. I sat back and let the feeling overtake me. Soon we both came.

We settled underneath the covers of Chantal's bed, and held each other until we fell asleep. The next morning, I drove Chantal to the hotel. She proceeded in, and I waited 5 minutes before following. I grabbed a quick shower, changed, and head right back out of the hotel to the work site. All the way to work I couldn't help but look forward to both my lunch with Rebecca, and whatever erotic pleasures awaited me that night with Chantal. Usually travel is such a pain, but this was turning out to be one of the best trips I had ever taken.

Chapter 3: Lunch with Rebecca

The construction site positively stopped when Rebecca pulled up. I was standing outside the trailer discussing vinyl versus cloth seating with an extremely cost conscious regional manager when the Mazda Miata pulled onto the site. And out stepped Rebecca, and the regional manager stopped nattering about his budget and stared.

Rebecca was wearing a navy pinstripe business suit. The skirt on the suit was raised about 4 inches above her knee, showing off an excellent pair of legs housed in a pair of silk blue hose. She was wearing 2-inch heels, which gave an even better shape to her legs and rounded her ass out even more. Underneath the blue jacket of her suit she was wearing a ribbed t-shirt the clung tightly to her body. As she stood from her car, she jacket flipped open and you could see that she was not wearing a bra, the tight top tracing even line of her small but firm breasts. She did up her jacket and started to walk towards the trailer.

Ever eye followed her. Construction is a very male dominated business, and it is a rare occasion where a woman shows up on the site. It's even rarer when the woman who shows up is a tall, good-looking blond. Rebecca's long blond hair bounced against her back as she walked towards me. I looked around. Inside the partially built store, 3 carpenters that had moments earlier been constructing a counter top stood and watched Rebecca's long, confident stride. Beside me, the regional manager gulped and shift uncomfortably. On my other side, the head contractor smiled and puffed out his chest. Rebecca walked up to me, and in European fashion, kissed each of my cheeks. "Bonjour, mon aime. Are you ready to go?" She asked, keeping her gazed fixed on me.




Dirty Business Trip



"You will have to excuse me, gentleman," I said to my companions. "I am going to lunch with Rebecca here, who is a local interior designer. We are going to discuss some options for the interior of the restaurant."

"Umm, perhaps I should come to?" asked the regional manager, hopefully. The contractor stifled a laugh.

"Oh, I would love to have you along," Rebecca said, shifting her gaze from me to the manager, "but my car is only a two seater. Sorry." Rebecca took my arm, and we started to walk towards her car. Behind me I heard the head contractor laugh out loud.

We reached the car, and I took one last look at the construction site. The regional manager had disappeared into the trailer, but the three carpenters and the contractor were standing together, whispering softly with their eyes fixed on Rebecca. "Horny little bastards," I thought to myself, "if only they knew what amazing surprise is hidden under that skirt."

Rebecca has booked us lunch at a "quiet, dark little restaurant where we can talk in peace," she told me. "I hope you don't have to be back too quickly, we have a lot to discuss."

"Oh no. Firstly, I have already introduced you as a business colleague, so I can always claim that we were actually discussing business. And secondly, I don't think any of those guys could fault me for taking a little extra time at lunch with such a beautiful blond."

"Oh, you are so sweet," she said, downshifting into a corner. "I must admit, though. Having all those hot, blue-collar men staring at me was a bit of a thrill. I have a fantasy about being serviced by a bevy of construction workers in a house being remodelled. I have never had the guts to fulfil it. You never know how a group of men would react to finding out my little secret."

"If I recall from last night," I said, "you're secret wasn't so little. It was big and hard, and tasted great." I could feel my penis growing in my pants. "How do men usually react when they find out you are a transsexual?"

"It depends."

"On what?"

"If they are alone. If I have a man in my bedroom, and it is just the two of us, when I peel off those panties 9 times out of 10 the man gladly sucks me off. Oh, they may play a little 'oh my, you are a guy' game for a minute. But most men are so horny that they will fuck anything."

Rebecca continued, "now, it's a different story if I am with a group of men when they find out. They play all macho, and act disgusted. But let me tell you, more than a few times when I have revealed my secret to a group of men, the men come up individually later to get my phone number. In fact, usually the ones who protest the loudest are the first ones to want to get in your pants and suck you dry. Secretly, I think all men want a spin with a transsexual. They are just afraid to admit it. So what about you, before your night with Chantal, have you ever dreamed about being with a tranny?"

"Actually, no." I said. "But I had never seen one that looked as good as Chantal. Or you. The only transsexuals I had seen worked a street corner in the city, and looked like they could use a good shave."

Rebecca laughed. "Yeah, most of those 'transsexuals' are just gay guys who put on a dress to get some action. Real transsexuals like Chantal or myself are actually women, at least emotionally. Somehow the gender in our head doesn't match the gender of our bodies."

"So, do you want to have a sex change then?"

"Myself, I don't. I am happy with the person I am right now. I have an excellent job, I look fabulous and I have friends and family who love and support me. I feel like a woman, but my penis is a part of me. Cutting off my penis would be like cutting off my arm. I don't see what good that would do."

Rebecca pulled into the parking lot of a small Italian restaurant. She parked the car, but didn't turn it off right away. "Chantal feels the same way I do. We both feel like women right now. We don't need a surgery to confirm that. But not everyone feels like I do. Some of the transsexuals that I know want to go through the surgery and fully become women. If that's what they want, then I say they should go for it. But for me, I could think of better things to spend my money on, like my education or this car." With that Rebecca shut off the engine and we proceeded inside the restaurant.

Our table was at the back of the restaurant, in a small alcove that held only two other tables. Given the fact that there were only 3 other tables in the restaurant currently occupied, it seemed quite likely that we would have the room to ourselves. "The restaurant is quite good," Rebecca said, "despite the small crowd. It is a lot busier at dinner. It's location is very far from any major office parks, so it's not really convenient for lunches, unless you are having an affair and want a discrete place to meet."

"Is that what this is," I asked, pulling out Rebecca's chair for her, "an affair?"

"Oh no," Rebecca said. "Firstly, Chantal knows that we are together. And secondly, we are just having lunch. Nothing more." I could feel my heart sink in my chest. I was very excited about the possibility of having sex with Rebecca, but with that statement it appeared that it wasn't going to happen, at least not at lunch.

I was soon over any regret about not getting to fuck Rebecca. We talked about a number of clients that she had or currently was working on, and the type of design ethics that she employed. I sat memorised as I listened to Rebecca discuss her work. She had such passion for her job that I could see were that confidence came from in her walk. Listen to her, I could understand why she didn't need an operation to confirm she was a woman. She knew who she was, and she didn't care what you thought about that. If you believed what she believed, then she would be your friend. And I could tell that she would be a fierce and loyal friend. And if you didn't see eye to eye with her, she wouldn't concern herself with you. She would leave you to live your life, and she would go on living hers. But if you crossed her, she could take a pound of flesh out of you and leave you whimpering like a hurt puppy in the corner.

"So, enough about me," Rebecca said as we finished our main course and waiter cleared away our plates. "Tell me a bit about what you do. What are you erecting here in town?" she asked. When she said the word erecting, a sly smile came across her face and her bare stocking foot pushed between my legs. My penis sprung to life, quickly becoming erect at the insistence of Rebecca's stroking foot.

"It's a restaurant, part of the chain I work for. They are pretty much an out of the box type thing. Same look at all the locations. Gives the customers a sense of security. Knowing that no matter where they go, they can find something familiar." My left hand reached across the table and stroked Rebecca's hand. My right hand was under the table undoing my fly and allowing Rebecca access to my cock. Her foot worked her way inside my pants and through the fly on my underwear to touch my naked cock. She gripped the shaft of my cock between her first and second toe, and started stroking it up and down.

Above the table, Rebecca's face was calm, like nothing was happening. "That must not provide a lot of creativity on your job, if you are putting up the same thing over and over again. I feel that we all need variety in our lives, don't you? I mean, why keep doing the same thing over and over when something so different, so unique, so special is just around the corner." I wasn't sure if she was talking about my job or my sex life, but I was finding it hard to keep a straight face. I could feel the heat rising in my face, my breathing was becoming heavier, and I was starting to shutter uncontrollably.

"I don't know," I managed to get out, my voice cracking. "There is a lot to be said, at least from the construction point of view, to being consistent. However, I do agree with you on the point about trying different things in your personal life. I, for instance, have never had sex in a public restaurant. How about you?"

Rebecca squeezed my cock between her toes. "Let's see. I have had sex in a club before. Out on the dance floor. I was wearing a short skirt and no panties. I started grinding against my boyfriend at the time and next thing I know he had undone his fly and was entering me. No one even noticed, but it was quite a thrill. Being so close to getting caught. I tell you, all this talk about sex has me quite hot. I think I am going to go to the washroom. Would you care to join me?" Rebecca rose out of her seat and started walking towards the restroom. I quickly pulled up my zipper, and followed.

Rebecca was waiting outside the washroom doors when I arrived. She grabbed me and pulled me in to the ladies room. We entered the first stall, and Rebecca locked the door behind us.

I sat on the toilet, and undid my pants, releasing my hard cock to the air. Rebecca turned around and pulled her skirt up. Her stockings rose up to her thighs, and she was wearing a pair of black panties. She pulled the black panties down around her ankles, and then stuffed them in her jacket pocket. She spread her legs slightly, and her penis, which had been tucked between her legs dropped down. She rubbed her cock and balls a few times, and I could see her penis start to grow.

I grabbed Rebecca's hips, and pulled her close to my face. I started by licking her balls as she slowly stroked her cock. Then I ran my tongue between her butt cheeks. As my tongue reached her asshole, Rebecca pushed back against me. However, I didn't let my tongue enter her, at least not yet. Instead I continued licking her crack up to her back, and then back down again to her balls. Rebecca's cock was now fully erect. I took her balls in my more, and pulled on them. Rebecca let out a shocked moan and started stroking herself even faster.

I released her sack from my mouth and worked my tongue back up to her hole. This time, I didn't resist penetrating it. As my tongue worked in her ass, Rebecca moved her ass back and forth against my face. Her breathing become heavy as my tongue spread her hole wide open. "I think you are ready to be fucked." I said removing my tongue from her ass and sitting back on the toilet. Rebecca lowered herself onto my cock.

I watched Rebecca's blond hair bounce against her back as she slid up and down my cock. I reached around with my hands, using one to massage her clothed breast and using the other to play with her hard shaft. I could feel myself reaching the verge of coming, so I started pushing up against Rebecca, trying to get deeper inside her. With a final few thrusts, I came.

"Oh no," said Rebecca. "I can't put my panties back on like this. Your come is going to run right out and create a wet spot on the back of my dress. How professional would that look?"

"Don't worry," I said, once again grabbing Rebecca's hips and pulling her close to my face. "I will clean you out." I buried my face in between her ass cheeks and sucked my come out of her ass. Rebecca was delighted, it obviously showed when she turned around and her cock was standing out hard in front of her. "Not to mention," I continued, "that we can't let you walk out the restaurant without taking care of this." I slipped my mouth, wet with my own come down onto Rebecca's shaft. Rebecca grabbed the back of my head and started furiously fucking my face. I could barely breathe, but it didn't last long before Rebecca came into my mouth. I swallowed every last drop.

Rebecca slipped back on her panties as I did my pants back up, and he headed back out to the table. The bill was waiting for us, so I paid it and we headed back out to Rebecca's car. "You know," I said, "that restaurant has some excellent food. But the dessert that was served in that washroom stall was the best part of the meal." Rebecca and I both laughed as we climbed into her car.

Chapter 4: Nicole's Room

I had spent nearly 2 hours at lunch that day, so I was very behind at the end of the day. I didn't end up leaving work until 8pm. I was supposed to meet Chantal at her house at 8pm. I phoned at 7:30 and professed my apologies.

"Don't worry," she said. "Rebecca and I are going out to get some dinner. Just come over. By the time you get here, Nicole should be home, and she can let you in. I will see you when Rebecca and I get back."

I arrived at Chantal's house about 8:20pm. Rebecca's Miata wasn't in the driveway, but a Honda Civic that I had not seen before was. I knocked on the door of the bungalow house.

A tall redhead answered the door. She stood about 5 foot 11, and was quite broad shouldered. Her face was square, but pretty, with green eyes. I quickly glanced down her body. She was wearing a t-shirt and jeans. The t-shirt was straining against the size of her breasts, which were incredibly large. She was quite curvaceous, unlike her two roommates who were slender. 

"Hello?" she said.

"Hi, I'm Alan. I am here to see Chantal."

The redhead's face lit up with recognition. "You're Alan. Yes, Chantal told me to expect you. Come in. She and Rebecca went out to get some dinner. They should be back within an hour or so. Make yourself comfortable. Can I offer you something?"

I asked for a glass of wine, and sat down on the couch were the night before Chantal, Rebecca and I had incredible three-way sex. I started reminiscing on the event, and my penis started to get hard in my pants. Nicole returned carrying two glasses of red wine, and took the seat beside me.

"So, Rebecca and Chantal are quite taken with you. They are like two little school girls giggling all the time. You must be quite a man to get two worldly woman like Rebecca and Chantal so giddy."

I blushed. "I don't know about that. We certainly have had a great time together the past couple of days."

"I bet you have," said Nicole. "They wouldn't give me the full details, but they said that your tongue has a way of finding just the right spot inside a woman like myself. You know, we have an hour before the other two get back. We could sit here and try and make polite conversation, or we could go back to my room and I could take you for a test drive."

I wasn't sure. After all, Chantal had given me her blessing to fuck Rebecca, and she hadn't said anything about Nicole. But my cock did perk up at the suggestion, and Chantal hadn't seemed to mind that I had lunch with Rebecca. "Sure. Sounds like it could be fun."

Nicole led me to the back of the house where the three bedrooms were. She opened the door to hers, and I was amazed at what I saw. It was like a sex shop, with hand cuffs and whips hanging from the wall. A large selection of dildos and vibrators were sitting on one shelf. A collection of dirty magazines and porno tapes were set up by the TV. And hanging in the closet which was open were a number of different fetish uniforms – The nurse, the maid, and a cop's outfit. The room was lit with a red light hanging from the ceiling. There were three pictures on the walls. Two photographs of naked man hung on one wall. Above the bed hung a large painted portrait of Nicole, completely naked. A large, thick cock hung between her legs.

Nicole slipped off her shirt and jeans. Underneath she was wearing a lacy one-piece body suit. She pulled me close to her, and I could feel her hard penis jut up against my leg. Our mouths met in a kiss. She wrapped her strong arms around me, and pulled me down with her onto her bed. "So Alan, I hope you like dominant women. Because I like being superior." She pushed me off her, and jumped on top of me. "Women on top!" she said, holding my arms above me head.

Nicole undid by shirt and pants, and undressed me roughly, but quickly. Soon I was lying on my back, naked on Nicole's bed. Nicole, still in her body suit, once again straddled me and held my arms back. "I think I need to ensure that you aren't going to go anywhere," she said, as she pulled a pair of handcuffs from a bedside table. She cuffed one wrist, put the handcuffs through the metal posts on her bed, and cuffed the other wrist. 

I was scared, but also aroused. Part of me wanted to ask Nicole to stop. Part of me wanted to scream. But another part of me wanted Nicole to have her way with me. I looked down at where Nicole sat on me. Our hard penises were touching, and I wanted to badly to have her cock in my mouth.

"What are you looking at?" she asked, glancing down between her legs.

"Your cock. It's quite big."

"9 and a half inches when fully erect. Do you like my cock?"

"Oh yes," I replied, feeling both foolish and turned on at the same time. "I would like your cock in my mouth." Nicole laughed, and pushed the crotch of her body suit away from her penis. She crawled up my chest, and let me taste the tip of her cock. After a few seconds of sucking, she pulled her cock away.

Once again she laughed. "Oh, this is going to be fun!" she said, and pulled the body suit off her left breast. She bent down and shoved the breast into my mouth. I eagerly sucked at it, her nipple getting hard in my mouth. As I sucked on her breast, Nicole humped against my stomach with her cock. I could feel it getting larger and larger. I thought it was impossible that her cock, which was already massive when she slipped it out of her body suit, could get any bigger. But I could feel it growing against me. Finally she removed her breast from my mouth, and I got a glimpse of her penis. 

It was incredible! It was long and thick, bending slightly to the right. Her balls were pulled up tight against her body. She stroked her cock a few times. "Are you sure you want all this in your mouth? You are such a small man, I don't know if you could take it all." She slapped her penis against my chest.

"Please," I said, desperately craving her cock. "Please, let me try." I don't know what came over me, but I needed Nicole's cock in my mouth more than anything. I strained at my cuffs, hoping that I could break free and grab her. But I couldn't. I was helpless. I had to do whatever she said. And if she decided not to let me suck her off, there was nothing I could do about it.

Nicole brought her penis close to my mouth. I strained my neck to try and get at it, but she pulled it back. Then, she traced the head of her cock over my lips. I stuck out my tongue and flicked at it. Nicole moaned with each flick of my tongue. She moved further up, putting her balls in my mouth. Her cock came to rest between my eyes and as she moved slowly up and down, her cock was rubbing against my face. I sucked at her balls and stared cross-eyed at the massive cock that pressed against my face.

Finally Nicole relented, let me take a few inches of her penis in my mouth. I sucked at it like a man who has been in the desert sucks on a wet cloth for water. I so much wanted more of her cock. Nicole moaned and leaned her head back, allowing more of her massive member to slide inside my mouth. She pushed it further and further down. I didn't know if I could take it all, the sides of my mouth were straining to open wide enough, and I could feel myself starting to gag.

But I caught myself. I started to think about breathing through my nose, and suppressed my reflex to gag at the enormity that was inside my mouth. After relaxing, I was able to more fully enjoy the sensation of having so much in my mouth. I moved my head up and down as best I could beneath the weight of Nicole's body. Nicole started pumping up and down on my face and once again I started to loss control. I felt as if I couldn't breath and I could feel my throat start to spasm to clear itself. I breathed harder through my nose, and regained control. Nicole pumped faster and I could taste the pre-cum on the tip of her penis. "Oh yes, I am going to fuck your face," Nicole said. "You dirty little slut. You like this, don't you? You like my huge cock in your mouth. Take it all, you dirty slut!"




Dirty Business Trip



Nicole pumped faster and faster. I ached to rub my cock, now hard as a rock, but I couldn't get my hands free. Nicole continued to talk dirty, calling me a whore and a slut and a horny faggot. I didn't care. I would put up with whatever insults she would throw at me, just so I could taste her come.

"Do you want my come in your mouth?" she asked, still pumping. I couldn't answer the question, my mouth was filled with her 9 and a half inches. I simply waited for the assault of liquid to fill my mouth. I didn't wait long. Nicole started making deeper strokes and the pitch of her voice dropped an octave. "Oh fuck yeah! Oh yeah! You dirty little slut. You lucky little whore. You get to taste all my come. Go ahead, drink it up, faggot. Enjoy my come you dirty little slut." With that, she pressed hard against my face and released herself in my mouth. There was so much come, it was all I could do to continually swallow. I could feel the come running down my cheeks. Nicole pulled out of my mouth, and stood at the foot of the bed.

"Oh my god. You do have an excellent little bitch mouth. No wonder Rebecca and Nicole like you so much. You are the perfect little whore, aren't you? And look at your cock, hard as steel. There I was fucking you in your mouth till the point where you couldn't even breathe, and that turned you on. Didn't it?" Nicole flicked my penis with her finger. It stung for a moment, but the pain quickly passed into pleasure. "I bet you want me to suck you off? Or do you want to fuck me ass?" She asked, slapping her ass with her hands. "Well, no such luck for you, lover boy. But I do promise that you will enjoy want is coming next."

Nicole slipped her body suit completely off, revealing her body. Her skin was white. She had a small shock of red hair right above her cock, but other than that was shaved clean. Nicole came around to the side of the bed, and climbed over me, positioning her ass right above me face. "Let's see what that magic tongue of yours is all about," she said, lowering herself onto my face. I stuck out my tongue, but my penis was aching for release, so I wasn't completely into it.

Suddenly, my penis was roughly being massaged. Nicole was using her feet to jerk me off while supporting herself above my face on her hands. The feeling of her feet against my cock revitalised me, and my tongue started working on her asshole with renewed vigour.

"Oh, that is good. Yes, push that tongue of your deep into me, slut boy. I can see by your cock that you like to lick ass, don't you?" Nicole wiggled her ass above me face and stroked my cock even harder with her feet. 

After a few more minutes of this, Nicole shifted. She got onto her hands and knees, with her cock hanging down over my chest and her mouth above my crotch. Nicole pushed her ass back, and I had to strain my neck to get my tongue in her hole. Nicole started stroking my cock with her hand, and blowing on the tip of the penis.

Her ass closed and opened around my tongue and I dug deeper and deeper. Nicole continued to stroke me and blow on the head of my cock, only stopping occasionally to moan or hurl another insult at me. "Yes, that's it you whore. Push deep into me, slut!"


Nicole's stroking and blowing was working wonders on my cock. Nicole could see that I was about to blow and so just kissed the tip of my cock. That was enough to push me over and my come shot out and all over Nicole's face. Nicole stood up at the foot of the bed again, and looked at me sternly.

"Now look what you have done," she said pointing to the come that was running down her face. "You have messed all over my pretty face." A drop of come ran off her square jaw and onto her breast. "You are going to have to pay for this."

Nicole crawled between my legs, and I noticed that her cock was long and hard again. She reached over beside the bed and pulled a jar of KY jelly out. She opened the jar and spread some on her cock. She grabbed my legs and swung them up onto her shoulders. Then she took another dab of KY jelly, and spread it onto my asshole, using two fingers to spread it around my hole, and then pushing inside me.

My asshole jerked shut and pain shot up through my body. "Relax," Nicole said as she pushed her fingers in and out of my ass. "It doesn't hurt if you relax your ass and let it happen." With each thrust of her finger, the pain was intense. I couldn't imagine that she thought she was going to put her massive cock inside me.

"I don't know about this," I said weakly. I was powerless, and at the mercy of Nicole.

"Don't worry," she said, her voice taking on a soft tone for the first time since arriving in her bedroom. "I won't hurt you. It feels quite nice, you just have to learn to relax and accept it." She continued talking softly, her left hand gently rubbing my leg while her right hand continued to open me up. Soon the fear was leaving me and the pain had disappeared. "Now I am going to try three fingers," Nicole said, and I felt my ass open even wider.

This time, there wasn't any pain. It was an uncomfortable feeling for a moment, but then it passed. Now it felt strange, like I was taking a really long dump. There was no pain, just a feeling of movement inside me. Nicole pulled out her fingers, and my ass felt great. I felt like I had just taken the greatest shit in the world and pleasure engulfed my body. Nicole pulled herself closer to me, and pushed her cock inside.

There was a little pain, but Nicole started talking softly again and I relaxed. The feeling of her cock pushing in and out of me was odd, and I shift around my ass. Occasionally her cock and my ass would hit some magically mark, and my body would shutter with pleasure. Then we would pass it and the feeling of having to go the washroom would return. Nicole continued gently pushing in and out.

I started to get more comfortable with the cock inside me, and started to move my ass around more, trying to find that special spot again. Sometimes I would find it for a moment, sometimes I would hit a spot that hurt. After a couple of minutes of experimentation, I learned how I could move to maximize the probability of finding pleasure and minimize the probability of finding pain. 

Nicole started to push faster and deeper. With each deeper thrust, I again had to experiment to find a comfortable position. But once I found the right position, it was okay getting fucked. Nicole's breathing quickened, and her face started to tense. I could tell she was close to coming. She started pumping harder and faster. I could feel my own cock starting to rise, twitching with each thrust.

"Oh yes," Nicole said, pulling herself out of me and taking her cock in her hand. The feeling of Nicole pulling out of me was even better than any feeling during getting fucked. It was like when you press really hard against your skin, and then release. The spot that just a moment ago you were making feel uncomfortable and painful is now the best feeling spot on your body. That's what my ass felt like. The feeling of the air against it was magically and my penis jerked up in reaction. 

Nicole stroked herself quickly. She threw her head back and started to come. The juice flew onto my chest and stomach as Nicole pumped her cock in her hand. She fell onto the bed beside me, exhausted.

"So Alan, what did you think of that?" she asked, grabbing the keys for the handcuffs and releasing me.

"That was bizarre!" I said. "It was a mix of fear and desire, pleasure and pain. Sometimes I was frightened, and just wanted you to release me and let me limp away. Other times I was so turned on that I would have done anything you asked. You have a real talent for this!"

"Well, I am glad that you enjoyed it. Chantal and Rebecca were right though, you do have an amazing tongue. You can stick that tongue of yours in my ass anytime."

I got up and went to the washroom to clean myself off. I thought about jerking off to take care of my hard-on, but just then I heard the front door open and realized that Chantal and Rebecca were home. "No," I thought to myself, "I am not going to waste this hard-on on a solo adventure. Instead I pulled on my pants and shirt, and headed out into the main hall to greet them.

Chapter 6: Lover's Cave

When I exited the bathroom, I was thinking about all that had happened to me in just three days. When I arrived in town on Monday, I had never even thought of having sex with a transsexual before. Now it was Wednesday night and so much had happened. I sucked my first cock and licked someone's ass for the first time. I had developed a taste for semen. I had a three-way encounter with two transsexuals. I had sex in a public place. I had tongues, fingers and a penis in my asshole. And I had experienced my first taste of bondage. I walked gingerly down the hall. My ass was a touch sore, and I spread my legs a bit as I walked to give it some air. And my jaw muscles were aching from having swallow Nicole's nine and half inch cock. I couldn't believe something that large had been in my mouth. I couldn't believe that it was also in my ass.

Nicole was standing at the door, still completely naked, whispering something in the ear of Chantal. Chantal was listening intently, and then smiled. "Did he enjoy it?" she asked Nicole, while gazing right at me.

"Oh, he had a good time. If you want proof, look at the bulge in his pants." Nicole responded.

I looked down and noticed that my cock was hard and tenting out my pants. Despite all that had occurred in the past couple of days, my cock was still ready for more action. I couldn't believe that this was happening to me, but I couldn't wait to find out what was going to happen next.

Chantal walked up to me, took me by the hand and led me into her room. "So, I hear that you had your cherry popped tonight. And from Nicole's huge cock. You are quite an adventurer to take on so much. I remember two days ago the look on your face when you first saw my cock. And now you are an old pro." Chantal stripped out of the dress she was wearing, and put on a pair of jeans and a sweat top. She dug around in her closets for a moment, and pulled out a sweater for me. "Put this on, it's a little chilly out."

"Are we going outside?" I asked.

"Yes, I thought that after all the adventure that you have had, you might enjoy a quiet walk in the park tonight. Give you a chance to rest." The tip of my penis stung every time it brushed against my underwear, my ass was still stinging a bit and my jaw was aching. Maybe a nice, quiet evening would be a good idea. I pulled the sweater over my head.

The park that Chantal had mentioned was about a 15 minute drive away, north of the city. We took my rental car and I followed the directions that Chantal gave.

"This park is one of my favourite places," she confessed during the drive. "When I was a young boy – 12 and 13 – I was very confused about who I was. While all my other friends were playing football and wrestling, I was feeling like a real outsider. I used to ride my bike to the park – now that was an hour and a half cycle – just to get away from people. I felt fine as long as there were no people around. But if there were people, then I felt pressure to conform. In the park, I felt like I was a part a nature – a natural part of nature. With people, I felt like an outsider from society. I almost dropped out of high school to become a park ranger," she said, laughing. Her face lit up when she laughed. I reached over and took her hand.

Chantal pointed right. "Turn here," she said, and then continued with her story. "Anyway, when I turned 15, in my second year of high school, I was staying late after a gym class. I never liked to change when the other boys were in the change room. Part of me was afraid that I would get aroused if I saw them naked, and another part of me was afraid that they might get aroused if they saw me. I wasn't sure that I wanted anyone to be aroused by me. So I am in the change room, taking a shower when in walks the star running back for the school's football team. And he has a hard on.

"'Oh, I am sorry. I didn't realize anyone else was in here,' he says, covering himself up with his towel. But then he sees it is me, and drops the towel. He walks over to the shower beside me, turns on the water, and starts masturbating right there in the shower. I didn't know what to do. He looked over at me and reached out to touch me. I was so frightened, I ran right out of the shower, got dressed and didn't come back to school for the next three days. You know why I was so frightened? Because when I thought about him whacking off in front of me, and I imagined that he might be thinking of me when he did it, I got aroused.

"I was sure that I was gay, which depressed me endlessly. The last thing I wanted to be was a gay man. I returned to school the next week and of course the first person I run into is the running back. 'Listen,' he says to me, his voice growling, 'if you tell anyone about what I did in the shower, I will fucking kill you. Do you understand?'

"I was so ashamed and humiliated. I thought that he may have liked me, but then he threatens to kill me. I left school right after running into him, went home and packed a bag and ran away.

"I was out on the street for two days when I ran into my first transsexual. I was instantly attracted to her, not because I wanted to be with her, but because I wanted to be her. She was about 10 years older than me, but we became friends, and she asked me to move in with her. Over the next five years, she taught me everything that I learned about being a transsexual woman. How to walk, how to talk, how to dress, how to flirt with men and how to pick out the men who are going to flirt back.

"I am not proud to admit this to you, but during that time I was a prostitute. It wasn't that bad. Most of the men were quite decent, just guys with strange urges that needed a woman like me to fulfil them. During that time I got my breast implants and started taking hormones to appear more female. I even went so far as to meet with a doctor about sex reassignment surgery. But I still didn't feel right. I still felt like I was not me, but someone else. I had hoped that the sex change would erase those feelings.

"Then I meet Rebecca. She was as she is now, the most confident person I had ever met. She was a transsexual, but she didn't want a sex change. The more I talked to her, the more I understood what was wrong with me. It wasn't that I was a woman trapped in a man's body, and that all I needed was to cut off my penis to be happy. I wasn't happy because I didn't like the path my life was taking. Rebecca taught me to figure out what I wanted to do, and pursue it.

"I moved out of my loft downtown, and out to the bungalow with Rebecca. At the time, Nicole wasn't our roommate yet. There was another girl, Cindy. She's married now, to a nice straight man. Anyway, after searching my soul, and trying a number of things, I discovered that I wanted to design environments. I wanted to try and create a man made structure that captures the feelings and emotions that I feel when I am in the park. And as soon as I set myself on the path to become an architect, I lost the urge to have the sex change."

We arrived at the park, and I shut off the car. Chantal got out, threw on a knapsack and walked into the darkness. I followed here. We walked for about 30 seconds along a dark path before we came upon a clearing. Along the north side of the clearing was a 30 foot cliff, and along the top of the cliff I could see a few fires burning. "Campers," Chantal explained and continued through the clearing towards the cliff.

When we arrived at the base of the cliff, we were standing at the entrance to a small cave. It was about 30 feet deep and 10 feet wide. Chantal took out a flashlight, and shone it inside the cave. There was fire pit and old bottles lying around the cave. "The teenagers like to come here to drink. It's a school night, so there won't be many around." Chantal proceeded into the cave and walked to the back. I followed, nearly tripping on the uneven floor a few times.

Chantal climbed up a couple of rocks, and disappeared into a 3 foot by 3 foot opening about 6 feet off the ground. "Come on up," she called. She poked her head out, and shone the flashlight down the rock slope so I could see where to put my feet. I climbed up and entered the small opening.

There was a tunnel that was about 6 feet long, and it then opened up into a small cave that was about 4 feet high, 8 feet deep and 4 feet wide. Chantal opened her knapsack and pulled out a blanket and 4 candles and candleholders. She lay the blanket on the ground, setting all four up at the far end of the cave. Then she lay on the blanket and motioned for me to join her.

It was a tight squeeze, but I managed to shimmy in beside her.

"This is Lover's Cave," Chantal said, putting her arms around me. "When I was in high school, this is were the kids that were dating would come to make out. Obviously, when I was in high school I never came up here."

Chantal closed her eyes, and lay her head on my chest. I kissed the top of her head. The cave was getting warmer. It didn't take the candles long to generate heat for such a small space. With the candles, the sweater I was wearing and Chantal cuddled up beside me, I started to feel beads of sweat developing on my forehead. "Whew, it's getting hot in here." I said.

"Well," Chantal said, "we can't put out the candles, because they we wouldn't have any light. And we can't move farther apart, because there is no where to go. So that leaves only one option. We will have to get you out of those hot clothes."

It was a struggle getting undressed in such a small space. But soon our clothes were off and flung carelessly towards the mouth of the cave. I was completely naked, and Chantal was wearing nothing but her bikini briefs. We started kissing. My hands caressed her soft dark hair. My left hand slid down from her hair towards her breast. I took her breast in my hand and gently played with the nipple. The nipple started to become hard as I fingered it.

Chantal's hand found their way down between my legs. My penis was partially erect, but was aching for a lot of action over the past couple of days. Chantal was gentle with it as she stroked it and it responded by growing in her hand. Our kisses become deeper and more intense. My left hand moved down from Chantal's breast and into her briefs. I found her penis, which was getting hard, and let my hand stroke it. Chantal's mouth opened to let out a moan, but I pushed my tongue deep into it so it wasn't heard.

We sat there for a while, kissing and stroking each other. I slowly moved myself on top of Chantal without breaking our kiss. My hand slipped her briefs down around her thighs and our naked penises touched. I rubbed our cocks up against each other by circling my hips back and forth.

"Rub it against my balls," Chantal said, only breaking our kiss for a moment. With my hand, I bent my penis so it was facing down and started rubbing my cock up and down between her legs. She closed her thighs tightly around my cock, and started swaying them back and forth. With my cock trapped between her legs, I started pumping up and down. It was just like fucking a woman in the missionary position.

I could feel Chantal's hard cock bouncing up and down between us. Her hand moved down and she grabbed the base of her cock with two fingers. She then batted it up and down between us, first hitting my stomach, than hers, than mine again. I continued to pump between Chantal's legs.

The cave was getting even hotter and soon we were both covered with sweat. But I didn't care. I continued fucking Chantal's thighs and she continued to play with her cock. The feeling was heavenly.

But the heavenly feeling had to come to and end. And come to an end it did. After I came, I started to get up, planning on moving down and finishing Chantal off orally. But she held me tight. "No, stay on top of me," she moaned breathlessly and as pulled me close with on hand and continued to masturbate with the other. And so we continued kissing and I caressed her hair until she came, covering both her and my stomach with hot come.




Dirty Business Trip



Chantal and I lay beside each other, facing each other and softly caressing and kissing. Soon a couple of the candles burnt out, and the sweat on our bodies began to chill us. So we got dressed and left the Lover's Cave to the next set of sweethearts. However, I can assure you that no high school couple could reach the passion that Chantal and I reached in that hot, small, dark cave.

Chapter 7: The Last Night

It was Thursday night and my last night in town. On Wednesday night, Chantal and I had talked after making love in the cave. I told her that because it was my last night in town, I wanted to take her out someplace nice. It was a thank you for being so kind to me, and introducing me to such exotic delights.

"How do you feel about dancing?" she asked.

"I left my club clothes at home, but I can probably find a pair of black pants and a black t-shirt that would do the job."

"Great," Chantal said, "because there is a new club I have heard about that I have been dying to try."

And so on Thursday night I went back to my hotel room after work and got ready to go out clubbing. I picked Chantal up at the bungalow at 9 o'clock and we headed to the club. Chantal was wearing a tight black dress and high heels. Her shoulder-length brunette hair was teased up and her lips were painted a bright red.

"Please place is called 'The G Spot.' It is out in an industrial area, but it's the latest rage, apparently." The club was out in the middle of nowhere. But it was surrounded by cars and already had a line up outside. "Don't worry," Chantal said. "One of the doormen here used to work at the hotel. He'll let us skip the line up."

We walked to the front of the line. The line was filled with all the beautiful people – statuesque blond models and ruggedly handsome men. I felt a little underdressed and a little ugly. As I was examining the line and feeling inadequate, Chantal was talking to one of the doormen. She grabbed my arm and pulled me over.

"Alan, this is Phil." I extended my hand and we shock. Phil was big, probably about six foot 2, and his biceps were about as big as my head. He had shaved off all his hair, giving him a nasty appearance. Chantal and Phil chatted for a couple of minutes, and then Phil pulled back the velvet rope and let us enter 'The G Spot.'

The club was a large, empty room. The walls were painted bright red and flashing lights of all colours lit up the floor. The music was unrecognisable to me – just drums and synthesisers. But the crowd seemed to love it and moved maniacally on the dance floor. Chantal and I wandered over the bar and ordered a drink. We stood at the bar and attempted to talk for a moment, but determined that with the music so loud that was a pointless exercise. Chantal pointed out at the dance floor and I nodded.

It had been a while since I had danced at anything except a wedding. And certainly there wasn't anyone out on the floor doing the chicken dance. Some people grooved off in their own little worlds. There were a few large groups of people that danced in circles. And then there were a number of couples and triples out on the floor, bumping and grinding each other like dogs in heat. As I stood there taking in the scene, Chantal stood in front of me and started grinding her ass back into my crotch. My cock immediately responded by getting hard. I grabbed Chantal's hip with my right hand, put my left hand on Chantal's back and started grinding her right back.

Chantal's ass pressed against me. I swivelled my hips until my cock was positioned between her ass cheeks, and then I started pumping up and down. I thought back to Rebecca's story about getting fucked on the dance floor, and wondered if Chantal was wearing any underwear. But the dance floor was a little too empty to provide any cover for that, so I kept my pants done up, and instead continued to hump Chantal's ass through my pants and her dress.

I closed my eyes and listened for the beat, moving my hips up and down with each pulse of the bass drum. Chantal swayed her ass from side to side, bouncing my hard penis around like a pinball. It was only 9:30, and already I was ready to leave the club and fuck. But the club was open until 2pm! I didn't think I would be able to make it through a whole evening of this.

A pair of hands grabbed my hips, and I felt someone press up against my ass. I heard a feminine voice "do you mind if I join in?" The body belonging to the hands and the voice then moved around until they were standing in front of Chantal. There stood a 5 foot 6 inch tall blond. She was thin with average breasts, but one of the prettiest faces that I have ever seen. She leaned over and whispered something in Chantal's ear. Chantal nodded, and the blond sandwiched Chantal so that I was facing Chantal's back and the blond was face-to-face with Chantal. Chantal grabbed my hand that was placed on her hip, and placed it on the blond's ass.

Chantal leaned back. "Pull her closer to me!" she said above the roar of the music. I firmly grabbed the blond's ass and pulled her in tight, sandwiching Chantal between us. The blond was at first surprised and stopped dancing, but then the surprise washed off her face and she started grinding.

"What's your name?" I called over Chantal's shoulder.

"Lucy!" the blond responded back.

Chantal brushed Lucy's blond hair back around her ears. "You are very pretty Lucy," she said. Lucy blushed and mumbled a thank you. Chantal's hips were pressing forward into Lucy's crotch and Chantal's hands worked there way down from Lucy's face towards her breasts.

Lucy looked confused, but let Chantal rub her breasts through her top. Chantal looked at Lucy, and then gave her a quick peck on the lips.

Lucy seemed uneasy. "I am not sure about this. I just wanted to dance. I am not a lesbian," she said weakly, but didn't move away or make any motion to remove Chantal's hands from her breasts. Chantal moved in and kissed Lucy again, this time more deeply. Lucy closed her eyes, and started kissing Lucy back. Soon the two women were making out furiously on the dance floor. I pulled away from Chantal's back and moved over to the side to get a better view. My cock was hard in my pants and jutting out obviously now, but I didn't care. What a great show I was getting!

Lucy's hands roamed up and down Chantal's back. Chantal moved her hands off Lucy's breasts and gripped her ass with both hands. Chantal pulled Lucy towards her. Lucy broke off the kiss.

"I feel something," Lucy said. "Underneath your dress. I can feel something pressing against me."

"Remember how you said you weren't a lesbian?" Chantal asked. "Well, I have good news for you. I am not really a woman. So if you want to fuck me, you won't really be involved in a lesbian act." Chantal smiled, almost laughing at the joke. 

"I don't understand," said Lucy, confusion filling her voice. "You're a guy?"

"No," Chantal responded, still caressing Lucy's ass and grinding their hips together. "I am a shemale. I am a woman with a cock."

The abruptness of Chantal's statement made Lucy jump for a moment. But then she seemed to settle. Lucy raised her hand and stroked Chantal's chin. "This is incredible. I don't know what to think. I am turned on, but also confused. I don't know if I am attracted to you as a man or a woman. This is so strange."

Chantal placed her hand on Lucy's breast. "Go with what your heart tells you. Don't try and overanalyse. If you want to fuck me, then fuck me."

Lucy giggled nervously. "I think I do."

Chantal smiled. "Good. Let's get out of here then." So Lucy, Chantal and I left 'The G Spot' after only being there for half an hour, all of us turned on and ready to get down to business.

I got in the front seat of my rental, and Chantal and Lucy got in the back. They started making out, their hands exploring each other's bodies. Luckily the industrial area that the club was in was deserted at nights, because I was so busy watching the two of them in my rear view mirror that I ran 3 stop signs and nearly hit a telephone pole.

"Take off you clothes," Chantal said, and Lucy obliged. Soon Lucy was stripped down to her birthday suit. Her breasts were firm with large nipples. Her public area was covered with light coloured hair. Chantal placed her hands between Lucy's legs, and rubbed her. Lucy opened her legs to give Chantal better access to her pussy. Chantal fingered Lucy's clit with her thumb and used her first to fingers to penetrate Lucy. Chantal leaned in and started sucking on Lucy's breasts as she continued to finger fuck the young blond. I nearly swerved off the road into a ditch, and decided that I need to concentrate on my driving.

The next time I glanced back, Chantal had moved her head down between Lucy's legs, and was sucking and tonguing Lucy's pussy. Lucy's hands were on top of Chantal's head, pushing it up and down. My cock was about to explode out of my pants. I decided it was best to stare straight ahead at the road until we arrived at Chantal's.

Once we got to Chantal's we quickly moved inside. In Chantal's bedroom I took a chair at the foot of the bed while Chantal and Lucy lay down. Chantal continued to eat Lucy, moving her tongue in and out of Lucy's pussy, and lapping at Lucy's clit. Chantal grabbed Lucy's clit between her teeth and twisted it slightly. This caused Lucy to buck wildly, pushing her crotch up against Chantal's face. Chantal licked furiously as Lucy's hands came down and started to stroke her clit. Lucy moaned with pleasure, and had an orgasm that lasted almost 30 seconds.

As Lucy rested on the bed, Chantal got up and slipped out of her dress. She hadn't been wearing any underwear, and as soon as her dress was off her cock was standing straight out. Lucy looked with wonder at Chantal, this beautiful tanned woman with large breasts and a full cock. "Go ahead," Chantal told Lucy. "Touch it. It's real."

Lucy sat up in the bed and ran her fingers up and down the shaft of Chantal's cock. Chantal put her hand on Lucy's head, and guided it towards her cock. Lucy opened her mouth and swallowed Chantal's penis. Lucy worked back and forth on the shaft with her mouth while her hands masturbated her wet pussy. I had to undo my pants to relieve the pressure that was building.

I sat on the chair and stroke my cock as I watched Lucy bring Chantal to orgasm. Lucy pulled away from Chantal's cock as it unloaded, and Lucy's face was soon covered with Chantal's come. Chantal sat down beside Lucy and started licking the come off Lucy's face. I moaned as the pressure built inside me.

"Looks like everyone has come except Alan," Chantal said, moving to the end of the bed and pulling me off the chair. "Let's help him out." Chantal and Lucy started tag teaming my cock, each taking a few sucks before releasing it and letting the other one take over. After a few minutes of this, Chantal moved down and started licking my balls while Lucy continued to work on my shaft. In no time I exploded, raining cum all over Lucy's face and my stomach and chest.

We rested and drank a couple of glasses of wine while we learned about Lucy. Lucy was a student at the local university, taking a biology degree. She was only 21, and didn't really have a clear picture of what she wanted to do with her life. We told her not to worry, that those things have a tendency of making themselves clear in time. Chantal told her an abridged version of her life story, and I concluded with a quick overview of the highlights of my previously boring life. After a couple of glasses of wine, the conversation turned to sex.

"So," Chantal said. "I bet you have never done anything like this before."

"Not even close," Lucy replied. "I have never been with more than 1 person before, and the most adventurous that ever got was doing it doggie style."

"Do you have a boyfriend?" Chantal asked.

"Not right now. I used to have a guy I was going out with, but he graduated last year and moved to New York. We decided that it would be best to split up instead of trying to carry on a long distance relationship."

"So, what are your fantasies?"

"Oh. Nothing." Lucy replied, her face reddening.

"Come on," Chantal said, pulling herself closer to Lucy. "Us girls always have secret fantasies that we want to fulfil. What are yours? Doing it with another girl? Having a gang-bang with the basketball team? Fucking a goat?"

Lucy's face was bright red. "Oh god, not anything with animals! But I have dreamed about having more than one guy at once. You know, one guy fucking me regular. And the other guy..." Lucy paused.

"The other guy doing what?" Chant asked.

"...the other guy... entering me... in back." Lucy bowed her head down.

"Oh," Chantal said, looking intrigued. "Have you ever had it? In back?"

"Once, yes. But not with a man. With a dildo. My roommate, she's a bit wilder than I am. Anyway, she was out of town a couple of weeks ago, and I noticed that the door to her room was open. So I went to shut it, and then I noticed that there was a dildo sitting on her bed. Right there, out in the open. And I thought about my fantasy, and wondered what it would be like. So I tried it, with the dildo."

Chantal smiled and moved closer, rubbing her hand up and down Lucy's side. "And what did you think?"

"It hurt a bit. At first. But then it was okay."

"Do you want to try your fantasy for real? With Alan and I?"

Lucy didn't say anything for a minute, and then she rolled over onto her stomach and got up on all fours. Chantal climbed underneath Lucy, and Lucy lowered herself onto Chantal's cock. I grabbed a tube of KY off the dresser and started slathering my cock with it. I watched as Lucy pumped slowly up and down on Chantal's cock, and stared intently at her asshole, open and waiting for me to enter. After greasing up my cock, I took a dab of KY and put it around Lucy's asshole. Then, repeating what Nicole had done to me the night before, I enter Lucy. First with one finger, than two, and finally, when I felt that she was relaxed and ready for me, my cock.

Lucy moaned, and I asked her if it was alright. "Better than alright," she responded, and pushed back onto my shaft. I started pumping in and out, and I could feel Chantal pumping up and down underneath me. Lucy started breathing faster, and pushed back against me and down against with Chantal with more force. "Fuck me harder and faster!" she commanded. And we obeyed. Soon I was pumping in and out of Lucy's asshole with speed.

Chantal started to moan, "oh God, yes. I am close. I am close." She pumped faster, and let out a long breath followed by a serious of short breaths as she came inside Lucy's pussy. I started pumping harder, and within 30 seconds I to was ready to come.

"I am going to come," I announced.

"I want your come in my ass!" Lucy screamed. And so I obliged her. I pressed hard against her and my load shot deep into her. After the last drop was exhausted, I pulled out and lay down beside Chantal. Lucy, come seeping from her pussy and ass lay down on the other side of Chantal. And we fell asleep.

That was my last night in town. The next day I got up, drove Lucy to her dorm and then headed for the hotel. I dropped off Chantal and went up to my room to pack. I went down to the front desk and walked up to Chantal, standing there in her green business suit. I put my key card on the counter.

"Checking out?" she asked.

"Sadly, yes." I replied. I couldn't believe how close I felt to Chantal after only a week of knowing her, and I was going to miss her terribly. "I don't suppose you want to quit this job and fly away with me?"

"Alan, I would love to. But I have a life here. I am starting school in January, and all my friends are here. And you don't know that you really want me in your life. What we shared this week was fantastic, but we can't build a serious relationship based purely on the passion that we experienced this week.

"We need to take it easy for a while, digest what occurred. We can keep in touch by phone, and we can visit each other once and a while. But we shouldn't rush anything. For all you know, you may not even be interested in a woman like me for a full time relationship. I may just be a fling, and temporary passion that you had inside you that you needed to exorcise.

"Go home, don't overanalyse it, and call me. Maybe later in our lives we will hook up again, this time for good. Until that day, I had a great time this week. And I would love to see you again. And so would my roommates. Don't be a stranger."

And with that I signed my room bill and headed out the door. Where my new experience with Chantal, Rebecca and Nicole is going to lead, I don't know. But I am sure going to experiment to find out. There is a whole new world of woman out there for me to date now, and I want to find out if the qualities that they have are the qualities that I am looking for in a mate.

Until that day, it figures to be one hell of a great ride!



Dirty Business



I reached for a cigarette and lit it. After taking a long drag I spoke. " What the hell was that? " 

It was an honest question. I was a bit confused at this point, but I wasn't blaming Diane so much as I was searching for some kind of rational explanation to make the whole situation clear. But she was offended.

" It was sex Jake. " she responded tartly.

I don't know, for some reason that comment hit the wrong nerve. Angrily, I yelled at her. " Just sex? Like with your brother? "

She didn't say anything, just got dressed and left. I sat on the floor for awhile trying to search through my thoughts… trying to come up with a justification for what we did and to a certain extent, what Jude and Diane did. I was know drawn into this saga as much as they were, and the slow pain of guilt welled up in my stomach.

Over the next week, I had zero contact with either brother or sister. Jude was on a completely different schedule than me and Diane was… well, she was wherever she was. During those days I became depressed. My life had become complicated and I was in serious danger of losing two of my best friends at once. I figured that Diane was just as confused as I was about Jude and about me; she probably needed a break from it all. And Jude, well, I figured for him, he was confused as well. I didn't think he knew what took place between his sister and I but if he found out, there was no telling his reaction. 

Finally, after more than eight days, Jude and I were both in the house together with nothing else on our calendars. As Jude watched TV in the living room, I was preparing dinner in the kitchen. We hadn't said two words to each other all day and there was a certain something in the air between us. I broke the tension by offering him some of my meal, which he accepted. We sat on the couch eating, both staring intently on the TV as if to purposely avoid unnecessary contact between us. But a basketball game served to broker at least a modicum of peace and started to discuss sports. As the evening went on, our relationship seemingly returned to normal. We both adopted open stances; facing in other on the couch, activity involved in conversation. Although we hadn't talked I only a weeks time, there was loads of catching up to do. Eventually, we switched off the TV, turned on the music and continued our conversation over beer. 

I guess it was the alcohol that loosened Jude up. One minute he was talking about work and the next minute: " I know what happened between you and Diane. No, hold on… let me speak. She told me the other day and I think she is really hurting because of what happened. No, that's not the right way of putting it. Look Jake, she enjoyed what happened, she told me so. But because of recent events… with me… it just threw her into a state. Look, she's really upset and I think we all should talk… to work things out. " 

I took a big gulp of beer and lit a cigarette. I wanted to play the whole thing cautiously. 

" Well, " I said. " I have been as much as a wreak as she has. I mean, it just happened between us and there didn't seem to be any precursor to it. I guess, what I was most concerned about was what you would think man. I mean, you guys have that thing going on, which I guess, I don't mind. The whole incest thing. "

" Aw Jake, don't say the I-word. "

" Hey, but that's what it is man. " 

I could see that Jude was growing a little agitated, so I backed off. 

I searched for the right words. " Look, you two are my best friends, we've known each other since we were little kids. You're both like family to me… "

Jude raised his eyebrows at that last part and I realized the joke. 

"… I just want us to be cool again. So, let's all get together and work this thing out. "

So, it was decided that I should be the one to give Diane a call and we talked a little bit to sort of establish a speaking relationship again. We set up a night that we would all be free and agreed to have a serious discussion about the current state of things.

I decided to prepare a large meal so we could all eat dinner first and become comfortable with each other; I just wanted the night to go as smoothly as possible. Diane came over during the evening; we all had drink before dinner and it seemed to loosen us up. Over the meal, we discussed politics, weather, school but saved the most important subject for later. It wasn't until after dinner that we got down to business. 

With Jude sitting on the floor and Diane and myself on the couch, we finally started to really talk. I don't know who spoke first on this matter but the conversation was going well. Each one of us started out with the preliminary: " I love you guys so much, I don't want to hurt you, it's all my fault. ". But then we started to express our deep down emotions. To my surprise, none of us was deeply hurt about anything. I told them I was cool with the whole brother and sister thing. Jude said he was comfortable with the thing between Diane and I. And Diane was comfortable with seeing both of us, if Jude and I wanted to see her. 

" Well, " Jude said, smacking his hands on his lap. " if you two think there's something serious between you, than you have my blessings. I mean Diane, we really couldn't have anything more than a purely physical relationship anyway. "

It was my turn to be humble. " With all do respect… I mean, I'm not exactly looking for anything serious either. So, you guys should continue to do whatever. It's not going to hurt me at all. "

Diane expressed concern on her face. " Look, I love both of you and have enjoyed being with both of you. But I don't want to become merely an object for you guys to offer to each other either. Maybe we should all just call it quits. I mean Jude, for obvious reasons we shouldn't see each other and Jake, I loved what we did but I don't want to compromise friendships just for the sake of a good fuck. "

Well, at least I'm a good fuck I said to myself half jokingly. However, Diane was right at the moment: the ultimate thing that we should all be concerned about is our friendships with one another. Sex would definitely come between us, or at least I thought. 

The conversation went on for sometime but we really only echoed what had already been said. As the night continued, things were seemingly getting back to normal; we were at least all comfortable with each other again and were able to talk freely. Jude broke out a bottle of Bourbon and with glasses in hand, we started going around and revealing, very explicitly, some of are more adventurous sexual experiences. 

Eventually I ran out of stories to tell and not wanting to be beaten, I leaned over and bumped Jude on the shoulder. " Hey Jude, remember when I brought over that porno and we were both so amazed because it was the first time we saw anyone going at it. "

" Oh shit yea! " He threw his arms up in exclamation. " I remember we were both shaking with anticipation because my parents took for-eeeee-ver to leave. And then I remember we both only had to watch like 30 seconds of the damn thing until we both had to beat-off. "

The three of laughed hysterically and I shouted. " What was it called? Oh, like ' Tijuana Babes ' or something like that, right? "

Jude's face was turning red. " No, no, no. It was something worse like ' Tijuana Tits '! " " ' Tijuana Tits '? " Diane, interjected through laughter. " I can't believe you guys could getoff on trash like that. "

" Oh well Sis, I remember that Jake and I would jack each other off. " Jude said while shooting me a fiery glance. 

Diane looked really intrigued by this bit of information. " Really, you two would do that with each other? I had no idea that you guys swing both ways! "

I leaned back and let the memories of Jude and I flood into my mind. " Hey, we were young and in our experimental phase so it was no big deal. And Jude, it only happened once as I remember. "

" Okay, so it only happened once. " Jude modified his position on the floor so that his arm was resting one knee and his shorts crawled up his leg. Looking down at him, I could the tip of his cock poking out and more than that, it was erect. Was it the memory that was making him horny? I asked myself. I shot a glance down at his crotch again and his dick was still there. My own member was stirring inside my pants but rather than be embarrassed about it, I reached under my belt and positioned my penis so that it was parallel to my stomach. 

" Okay sis… " Jude got this semi-serious look on his face that was consistent with his storytelling mode. " You see, Jake and me would beat-off together all the time when you guys weren't home. And this one time, " He looked at me and I nodded for him to go on. " this one time, we're sitting next to each other and Jake says ' I saw this porno at Harry Ellis' house where these one guy puts his dick between this other guy's butt cheeks. ' "

Diane giggled and I shrugged my shoulders in guilt. Jude continued. " So Jake gets me to lay on my stomach and he puts his dick between my ass cheeks and starts humping me. I mean, I was turned on but nothing happened. "

Jude's sister giggled again and turned to me. I picked up the story. " Okay, so I turn around and get on my stomach and your brother does the same thing. Nothing happens that time around either so finally…"

" Finally we both stand up and face each other and pull on each other's dicks until we both came in each others hands. " Jake finished. 

We all fell back and had a good laugh. There was a silence that I attributed to the three of us letting that memory roll around in our heads. My dick was almost painfully erect and, perhaps out my drunkenly lowered inhibitions, I rubbed it in full view of brother and sister. Neither of them seemed to notice so I gave and excused myself to the bathroom. 

When I came back, Jude had moved next to his sister and was whispering something with a shit-eating grin on his face. Diane laughed and shook her head. 

" Hey you two, cut it out! " I said jokingly.

Jude turned around. " I was just saying that I thought, since we all have seen and done things with each other, why can't we all just do it together? "

Not a bad thought. I said to myself but trying to maintain a little authority. " Now Jude, I thought we were done with all of this dirty business. "

" Yea, and although the thought of being gang-banged by you guys is not too revolting, we probably shouldn't do this. " Diane added. 

But Jude seemed to be set on this idea and buried his face in his sister's chest and ran his hands up her shirt. Diane didn't protest at all and grabbed her brother by the back with a sigh. I hung back for a moment and watched the scene unfold. Brother was now making out with his sister and it was really turning me on. Finally, throwing all caution into the wind, I approached the couple and knelt down beside them. With Jude sucking on her neck, Diane pulled me by the ear until our lips met. Perhaps sensing it was a little crowded, Jude's head brushed past my arm as he made his way down to his sister's stomach. I let up from kissing his sibling so that Jude could lift her shirt up. Diane sat forward, and removed her clothing for him, exposing her bra. I pulled a cup over her breast and she pulled the other one down. With our heads rubbing together, Jude and I both took nipple. 

Preceded with a devilish laugh, Diane breathed. " Oh my two boys! "

I straightened up, smiled at her and watched her brother work on both tits. I was feeling incredibly sexual, my hole body was alive with pleasure. There was probably no limit to what I would do at that moment and in fact, I made a move. Winking at his sister, I tapped Jude on the shoulder. He looked up at me as if to say: Hey, I'm busy here! But I leaned in and kissed him on the lips. I thought he might pull away but instead he stuck his tongue in my mouth and felt around the back of my teeth. I embraced him with my arms and shifted off of his sister and rolled around on the floor with him. The feeling of his weight on me brought back the memories of our earlier experience so many years ago. 

I heard Diane say. " Now this is hot! " and I giggled into Jude's mouth. I shut my eyes tight and let my hand find my way under Jude's pants to his ass. Gripping his butt caused him to buck his hips forward and I felt his hard cock grind into my leg. My own dick was oozing pre-cum and my underwear stuck to my skin. Finally we released each other and Jude rolled over on his back. 

We looked up to his sister who, during our make-out session, had stripped down to her panties and was standing up on the couch. I took all my clothes off and got up, gripped her leg and nibbled at her knee. I heard Jude disrobe as well and he joined me in tasting his sisters skin. Getting up on the sofa, behind Diane, I reached around and cupped her tits and sucked on her neck. I peered over for a moment and saw brother kissing sister on the mound of her sex. Playfully, I gave Diane's ass a little bump with a thrust of my hips so that her snatch would be driven up against Jude's mouth. 

" Hey guys, " I said. " let's go to someone's bed. " Jude agreed and he led the way to his room. 

I sat on the edge of Jude's bed and he reclined against the backboard, both of us staring at Diane as she stepped out of her underwear. 

Diane pushed on my chest. " Sit next to my brother. " I obliged and scooted back, giving Jude a excited pat on his lap. 

Diane crawled on the bed towards us and winked. I decided this was the point of no return and wanted to give both parties a way out. " Hey, are you guys still in to this? "

Jude just nodded enthusiastically. Diane, on the other hand, took my cock in her hand and used my pre-cum to lube my shaft. After pumping it a few times, I was convinced Diane was in it to the end too. She then took my dick into her mouth and used her other hand to satisfy her brother. 

It was either the sight of his sister giving a blow-job to another guy or the hand-job he was receiving that caused Jude to squirm and gasp. " Jeez this is so awesome! " Diane looked up at him and leaned over to take her brother's cock into their mouth, her hand remaining on my cock. Diane must have hit another nerve in her brother because he curled up in pleasure. His sister leaned back, released our dicks and reclined on her back, legs open. Jude and I both went for her crotch at the same time and after several " No, after you " moments I finally began to kiss his sister's snatch. Jude, down but not out, decided to work Diane's tits over with his hands and mouth. The little scene eventually turned into a groping match with the three of us bumping and grinding skin against skin. The thought of so much free flow of sexuality still, to this day, turns me on. 

Somehow, Diane ended up on top of her brother with me laying beside them stroking her body while gently nibbling at his neck. Diane reached behind her and guided her brother's dick in her snatch. He grabbed her by the hips and she rocked gently back and forth. 

It was a truly erotic scene: Brother and sister, who did look remarkably like one another, coupled in that way. That and the fact that, for me at least, this was the first threesome I ever experienced. 

I got up and crawled behind the siblings to get a good view of the action. Jude's nicely sized cock slid in to his sister and when he pulled out, the lips of her sex stretched out ever so slightly. Diane leaned down to kiss her brother, exposing her brown little asshole to me. A brief idea that I could enter her other hole came to me, but I didn't know if Diane was ready to take me in that way. Instead, I leaned and licked her anus, my chin almost brushing up against Jude's working cock. Diane responded positively to my advances, I so I moved in a little closer, working my tongue up her ass. Not wanting her brother to be left out, I reached under and grabbed him gently by the balls giving them a little squeeze. I pulled out of Diane's butt and with a lubricated finger probed her ass again until my there was no finger left. 

Again I removed myself and moved my faced into position again so that I was about a inch away from where brother met sister. The couple's fucking increased and Diane's ass was bumping into my face. Suddenly, Jude's dick left his sister's cunt and hit me in the chin with a Slap!. Diane scooted up a bit on her brother and turned around to look at the current situation. I froze at this moment of coitus interuptus, my hand still on my base of my best friends nuts. 

" Oh well! " I said and moved my hand so that I could stand Jude's cock straight up. I took the mushroomy head of his cock in my mouth and could taste both Diane's tangy juices and his salty pre-cum. With my mouth as wide as it could be, I fed the rest of his length down my throat. Surprisingly, there was little gag relax I slowly began to move up and down on his dick. 

Jude bucked his hips up a little bit and let out a cry. " Hey man, I'm going to cum in a second! " 

What are best friends for? I thought, easing up on his dick a little so that his thick spray would not hit the back of my throat. Finally I felt the thump! of this dick and the first orgasmic spasm released the warm, salty goo in my mouth. I wanted to release him but thought leaving him in mid-orgasm was a cold thing to do; the taste wasn't that bad. And so, with a few swallows and a couple more strokes and swirls of the tongue and I let him finish in my mouth. When his dick started to become flaccid, I sat up and wiped the excess jizz from my lips.

Diane bounced up and down and clapped. " That was the hottest thing I've ever seen! "

I took a shallow bow and winked at Jude. In return his wagged his finger for me to come closer and kneeling over him, I gave him a very salty kiss. He reached and tugged my at my dick and I muffled mmmmmm! into his mouth.

"Hey, hey, hey! " Diane protested. " As long I haven't cum and Jake is still hard, we still have some business to attend. Don't worry Jake, my brother got me most of the way there, you just need to finish the job. ". Diane got on her hands and turned around, meaning I should take her from behind. 

I looked down at Jude and smiled. " Diane, never send a boy to do a man's job. ". Jude objected by giving my cock a slap. 

I positioned myself behind Diane and slid my shaft into her snatch; the position giving me greater depth and a tighter feel. As I rocked rhythmically in and out of his sister's snatch, Jude moved behind my back. 

" What were you doing to my sister when I was fucking her? " Jude said. " Oh yea! " I felt thumbs part my ass cheeks and warm tongue flicker over my asshole. I bucked forward as my butt responded to this new pleasure. Slowly, Jude's mouth muscle slid it's way up my ass, and I had to slow my fucking to accommodate him. It felt like there was a big, juicy shit in my butt but in a more pleasurable manner, of course. 

Diane protested this interruption in her pleasure by forcing her snatch back onto my dick. I snapped out of my rim job and resumed banging her. Jude got up and kneeled along side me, one arm draped on my shoulder, the other arm forcing a finger inside me. 

" Mmmmm, yea! " Diane cried. " It's happening, yea, here it comes! " I hardly had to do anything; rather Diane was bucking back and forth. However, her brother's finger in my ass egged me forward. 

Jude leaned in close to my ear and whispered. " You know Jake, I never got to fuck you in the ass when we were kids man. Someday I'm going to fuck you so hard up you butt you're going to scream! "

Well, the dirty talk did if for me; I let my sperm go into Diane's snatch. Although she had finished her orgasm a moment before, my own climax caused her to let out a few more ooohs! and ahs! Finally, I withdrew and fell back onto the bed about the same time Diane collapsed into an exhausted pile. 




Dirty Business



It wasn't until we had regained composure and cleaned up a bit that we started to talk. The three of us sat in our living room, in various states of recline, puffing at cigarettes and replenishing our fluids. 

" Well, now the circle is complete. " Diane breathed. 

I gave an approving nod and fixed my eyes of Jude. " Hey buddy? "

" Yes. " he said.

" Are you really going to fuck me up the ass like you said in there? " I asked in my best, coy manner. 

Jude looked at me, looked at sister and back at me. " Well, I thought this was a one time only deal? "

I shrugged and said. " Well, I'm game if you're game. "

Jude nodded and glanced at his sister. Diane's smiled broadened. " Yea… me too! "

I was really one of the family now.



Dirty Butt Sex: Anal Threesome



I should start out by stating that the following story is true. I'm 28 years old and I've had sexual encounters with both men and women. While I lean in favor of being with women for dating purposes, I enjoy sleeping with men more. But perhaps the term "sleeping with" is not entirely accurate; I enjoy being fucked by men. Butt sex, as they say, is the best.

I am, for all intents and purposes, what many gay men would consider a "bottom." I enjoy taking cock in my ass. I enjoy having my ass ate out. I enjoy being rimmed, and fingered, and played with. I enjoy the feeling of sliding the largest cucumber I can find in and out of my hole. In short, I love ass play. When I sleep with women, I enjoy fucking them in the ass. In short, I really am sort of an ass man. 

While I've had several sexual experiences with women, I've only had a few encounters with men. Those encounters, however, were - and still are - electrifying to think of. I can remember the first time I had my dick sucked by a guy; the first time I had my ass fucked by a guy; and the first time I stuck another man's dick into my mouth and sucked him off. The memory I'm about to share, likewise, I can remember in vivid detail. It was about my first gay threesome. It gets pretty raunchy so keep that in mind. 

I am very average in real life. I look about average. My cock size is about average. My grades in high school and college are about average. The girls that I date are about average looking. Everything about me is, sadly, just about average. The only thing about me that makes me stand out is, perhaps, the fact that I have a well-defined body. I the first four years out of high school in the Army and developed a very rigid daily workout. The effort for all the work was a well-defined six-pack, pecs and arms. When I'm fully clothed, I'm just an average guy. When I'm naked, I'm a delicious platter of man meat (even with my average sized cock). At least that's what I've been told.

This is how I advertise myself on Craigslist: with my body. I'm not the only one with a six-pack out there true, but in my hometown, it gets you a lot of replies. So imagine my delight when a gay couple just a few miles down the road invites me over for a threesome and to participate as their bottom boy. Since I only do something really gay every few months or so, I try and make it as hardcore as possible. 

Prior to this point, I had only had a few gay encounters, and of those encounters, only twice had been anal. Each one was a painful experience, and I dreaded that I would never enjoy it even though I wanted to. People in porn looked like they enjoyed it, so maybe I was missing something. Maybe I just needed more practice. This turned out to be half true. 

When I showed up at their door, they greeted me and escorted me to their bedroom. As I walked through their home, they introduced themselves as Gary and Mark. I introduced myself by my gay alias, "Alex." As we entered their bedroom, I noticed the small arrangement they had set out for me - namely, towels for their beds and lube for my ass. 

As we're getting naked, I noticed that Gary cock was slightly larger and thicker than mine. He was a solid 6.5 inches and completely shaved except for a little mound above the base of his cock. I thought to myself that I could probably handle his dick in my ass without too much pain. His roommate, however, was much much larger and vastly thicker. I reached out to grab at it and realized that I didn't know what to do with it. I was easily 8 to 9 inches long and easily just as thick. I could barely fit the whole thing in my mouth let alone shove it down my throat. Gripping it in my hand and feeling it's sheer size made me feel both insufficient about myself while at the same time, incredibly turned on. One part of me feared having that thing enter me because it was going to hurt, but the more overwhelming aspect of me wanted to try.

As we started out, both Gary and Mark took turns blowing me. It was so hot. I lay there with my back against the bed, legs curled into my body and above my head while two men took turns licking my asshole and sucking my extremely erect cock. With my legs in the air I could barely see what was taking place, but I knew from the feeling in my bowels that fingers were starting to explore my anal cavity. At this point I hadn't had gay sex in months, so the feeling of - what I suspect - was two or three fingers was uncomfortable. But I loved it. The feeling of having a throat engulfing my cock while fingers moved in and out of my ass was amazing, and almost impossible to describe with words. My body responded by leaking precum. 

A few minutes in, Gary took over and started deep-throating me while Mark placed himself at my side. From this angle he could he could place his dick in my mouth. I tried to cram as much in as possible, but in the end, I just couldn't fit his 9 inches down my throat. Even with the few gay encounters I had previously, I had never really sucked a guy off. This was relatively new experience for me and I didn't know what to do. I compensated by massaging the tip of his cock with my tongue and slowly kissing his shaft. Precum started to ooze from his member and I curiously tasted it. To my surprise it was salty but had no actual "taste." Not bad I thought. 

That's when I heard the definitive sound of lube being opened. It makes a distinctive "pop!" noise. What followed was the sloshing sound of lubricant being generously applied to Gary's cock. Mark whispered in my ear to just relax and enjoy myself. He then signaled his partner to enter my body. I felt my hole stretch to accommodate his above average cock as each inch slowly made progress into my inner bowels. I bit my lip while grasping onto Gary's gigantic cock. He seemed to be enjoying my discomfort. By the time he was about three inches in I felt the uncomfortable pain of needing to shit, but being unable to do so. I tried to relax as he continued to push further into me, but the only thing I could think of was how badly I needed to go. He then started to move outward until he was all the way out. He exited my ass with a pleasant "pop" noise before starting the whole process again. Instead of stopping at three inches, he slowly filled me with four. Then with five. Then with six until he was completely inside of me. 

As I was being slowly broken in, I attempted to suck Gary's dick again. I had to take it out because the pain of having to shit was starting to over take me. I took deep, audible breaths and tried to relax. Instead of blowing Gary I was gripping onto his dick for dear life. The more pain I felt I was in, the harder I gripped his shaft. I tried to distract myself with sucking on his dick and jerking him off, but to little avail. Anal sex still hurt. 

My body was telling me I needed to go. I thought about calling it quits and going home, but I had to keep reminding myself: I had prepared myself earlier that day by emptying my bowels completely prior to coming over. There was nothing inside me that was going to come out. So I... just relaxed and, as gross as this sounds, tried to shit his dick out. And that was the key to anal sex. After a few minutes of training my body to this new sensation it started to feel good. Really good. I put Gary's cock back into my mouth and let Mark slowly plow into my body. My asshole was opening up and I learned to take his entire cock until I could feel his thick balls slapping against my butt cheeks. The feeling of pain started to subside and I focused on how good cock started to feel while it was deep in my ass. 

It was at this point that I realized that neither Gary nor Mark had any condoms, and I was pretty certain that the dick that was balls deep into my ass wasn't wearing one. I was alarmed, but I didn't care enough at this point to realize how reckless I was being. Having anal sex with two complete strangers? This wasn't like me at all - how stupid was I? I tried not to think about it but it couldn't escape me. I knew better. In the end it didn't matter; it felt too good to stop now. My mind's objection to this horribly risky scenario was being overruled by my body's craving for more cock. 

Every inch of Marks throbbing dick went in and out of my ass with a quickening pace. His breathing hastened, his thrusting became rough and erratic when all of a sudden, Mark came hard into my ass. I didn't notice how close he was at the time because I was too busy blowing Gary, but the sudden grunt, extra thrust and fresh flood of warm sperm into my bowels made me aware real quickly. I felt about four waves of sperm push into my bowels and the sensation left me feeling extra full. A few moments later Mark pulled himself out of my ass and I could feel his jizz leak out. I reached back and felt around my asshole. It was gaped wide. I moved my fingers around the perimeter to see how well it had stretched and was surprised on how large my asshole felt. I placed a few fingers inside, amazed by how easily they slide in and out. The sperm made my ass extra slippery. Wow, I thought to myself, I wish I could take a picture of this. 

Gary promptly removed himself from my mouth before his partner lavished his extra long and thick cock with lube. He used a lot and applied it with two hands. He had to his since dick was so large. Gary the laid down with his back and suggested that I sit on top of him. Gary's cock was like a tower. I stood straight up at a 90-degree angle, eager to penetrate me. I jacked it for a few moments, feeling its girth in its entirety before straddling him. I figured it couldn't be that bad. My ass was gaped open and lubricated with the Mark's sperm. I can handle nine inches no problem... right?

Well I thought wrong. As I positioned myself on top of his dick, I didn't realize how a few inches in width would translate into being an anal virgin again. Thank god Mark went first, I thought. I could barely fit Gary's cock into my ass - even after being plowed for 15 minutes! As opened as my asshole was, it felt like I was being fucked for the first time again. It hurt so badly even with my anal revelation of "shitting" a dick. I took about 4 inches over the course of maybe 2 minutes before having to get off to take a breather. Mark told me to relax while he fingered me. He inserted 4 fingers into my ass and I took it with little difficulty. The short time on Gary's dick had apparently stretched me even wider. After a few minutes of this, I got back on top. I slowly, and painfully, slid back down Gary's enormous cock. 

I was sweating. My asshole hurt so bad that I the only thing I could think about was apologizing profusely, grabbing my clothes and leaving. But I had to stick with it. Gary held on to my hips and paced my movement as I bobbed up and down his large shaft. My asshole felt like it was on fire and it wasn't going away. I actually lost my erection because I was so focused on the pain. Mark saw this and gripped my cock, opened his mouth, and started to blow me. I got hard immediately. My body was now torn on wanting to cum and wanting to shit. This sensation kept me from leaving, and I could feel the most powerful orgasm of my life building inside of my balls. About ten minutes later, Gary made me dismount him and position myself on all fours. We were going doggy style. 

To my surprise, Mark was hard again and decided he wanted to fuck. I made no objections; this was my first threesome, and I wanted to get the most out of this. His smaller cock slide into my gapping ass with no problems. He didn't even need lube, and after a few quick strokes, he started thrusting inside me harder and faster. I knew he was racing for an orgasm. I knew that my ass was loose enough for him to go as hard and as fast as he wanted without hurting me. And so I let him. I sank my face into the bed and looked at myself from their headboard mirror. My ass was high in the air with another man fucking the shit out of me while the other one jerked his dick on the side! I was a total anal slut and I loved it. I gripped the sheets of the bed with both hands and pushed back hard as Mark fucked me. I gritted my teeth and moaned. I could feel his balls slapping up against my body as he drilled himself deeper and harder into my bowels. An orgasm was building inside me and I could feel myself on the verge. I had never had an anal induced orgasm before, but this had to be it. It was so close!

But then Mark came. And the buildup stopped. As another load of Mark's sperm filled my bowels, I found myself shaking. I was so close to cumming. My asshole was wrecked and leaking cum and my orgasm that was building was turning into a painful blueballs. I NEEDED to cum SO badly. But Gary took this moment to change positions and immediately penetrate me. I was taken by surprise, once again, on how large Mark was and the painful sensation of having to shit returned. My face was still buried in the pillow, but I bit my lip. I started to breathe heavily and sweat started rolling down my brow. My erection would not disappear this time since I was stuck with an erection because of the blueballs. After all, Mark and Gary had been working my ass for about 40 minutes now and I had been horny all day. 

Gary's shoved his cock slowly into my asshole before picking up the pace. I tried to visualize how his thick cock must have looked as it disappeared, inch by glorious inch, into my inner bowels. I reached back with my hand and felt around my backdoor. It was stretched so wide and was amazed that I was able to take such a large cock. I then felt his balls slap against my hand. All 9 inches were in. Suddenly a sharp pain emerged in my stomach. I lunged forward trying to escape, as if out of reflex, but Gary stayed with me and pressed his body weight onto mine. I collapsed under his weight and was now lying face down with Gary's body on top of me, my hand still under me. I tried to move but Gary was determined to fuck the shit out of me with his large cock. I looked up and saw my reflection in the mirror. I gritted my teeth and gripped the sheets as Gary slowly removed his cock from my ass before thrusting it back in. As he pulled out, I gasped - the pain escaping, but returned each time he crammed all 9 inches back into my ass. I moaned each time, making an "UMPH!" sound. I wanted him to get off me, but I liked how dominated and full I felt. I instead moved my hand onto my cock. I NEEDED to cum I was so turned on. I tried to jerk off but I couldn't move my hand. Gary just rammed harder and harder into my ass, despite my attempts to get up. 

A few minutes of hard fucking with such a large dick made my ass muscles give up. I gave up trying to get up since my butt hole was completely destroyed. At this point I wanted to stop, but I couldn't because at the same time I felt so close to a release. Furthermore, Gary's large cock was starting to feel really good. He let me back up and asked me if I wanted to stop. I got back on all fours and Gary started to fuck me again. I wanted his cum now. I wanted it in my ass so badly. Mark, no longer content on just watching me get my asshole fucked, moved closer and started to jack me off. OH MY GOD, I could feel myself about to cum and it was going to be glorious. Gary removed his hands off my hips and used them to instead spread my asscheeks as wide as he could. He was now going all the way in and all the way out, each time making a wet "popping" noise. I could only imagine the sight he saw. My ass must have been gaped so wide. As Mark jacked me off faster, Gary placed his hands on my hips and started to thrust as hard and as fast as he could. I started to cum.

Mark's hand was like a blur as I started to release my load. I raised my head up, arched my back, and screamed "OH MY GOD!" as I began to cum. My legs were buckling; my toes curled; my body was twitching and contorting as wave after wave of orgasms hit me. The first wave of sperm had a slight delay after my first orgasm hit, but then I couldn't stop cumming. I had never come so hard in my life. My sperm was hot and thick as it poured out of me in one long string after another. The towel that was on the bed was now saturated with it. At the same time I felt my asshole contract as each orgasm came over me. This, in turn, triggered Gary's orgasm. With his last thrust, Gary came hard. All nine inches were in me and I felt an explosion of cum push into my inner bowels. It had nowhere to go as Gary only rammed his cock deeper into my ass as he came. I felt three distinct waves of sperm enter my body while Gary's still massive cock pulsated in my body. I felt so full with nine inches of cock in my ass and at least half a cup of sperm in bowels. 

As he slowly pulled out from my back door, I reached back with my hand to feel just how wide I was gaping. My asshole was MASSIVE. I felt around and determined that I could park a coke can in my asshole and still have room for a few fingers. Then the load of sperm started to leak out. I can't believe how much was in there. When I stood up more came out. I felt so good having the cum run down my leg, and I felt like I just took the best shit in the world. (Not a huge exaggeration really). I laid back down as my legs began to buckle from all the intense orgasms. I was exhausted. 

Gary then placed his cock in my face and I could tell that he wanted me to suck him off. I had never done ass to mouth, nor openly wanted to, but I felt as though I owed him. He just gave me the ass fucking of a lifetime. So I began by kissing his dick. I tasted sperm, lube and my own ass juices for the first time in my life. It wasn't as gross as I thought it would be. Sperm really doesn't taste like much, a bit salty I suppose, and I made sure I cleaned myself out prior to the days ass fucking so there would be no residual cling attached to his dick. I could smell the distinct aroma of my butt around his cock, but I figured I was already engaged this far in debauchery why not go on a little further? So I stopped kissing his dick and instead took him into my mouth. Even after he came he was still large, but he was soft enough to the point where I could fit more of him down my throat. He came a little more while I was sucking him and I licked it up with my tongue. I tasted him while trying to ignore the fact that I also tasted my own ass. I felt a bit queasy when thinking about it, so I stopped after a few moment and removed his cock from my mouth. Mark, whose hand was now soaked in my sperm, took the moment to make me taste myself by licking his finger. I tasted a bit salty myself but nothing bad. I hope my girlfriend thinks the same thing when she gives me a blowjob. 

I promptly washed myself off and put my clothes on before leaving. I always feel awkward after a bout of gay sex. After cumming I felt myself quickly returning to my normal "straight" self and promptly felt the need to get out of there as quickly, but as politely, as possible. I never saw these two again, but I wish I kept in contact with them. Even to this day, this was the most intense sexual experience I can remember and masturbate to it quite often. In fact, I've been so turned on just by typing this that I had to stop and finger my ass before finishing. God I could use a good ass fucking right now.

Well that's the end of my story. If you enjoyed it, and I hope you did, then let me know what you think! I have other experiences that I would like to share, like my first big black cock, my best blow job EVER, and the first time I fucked a girl in the ass, but those will have to wait for next time! 

If you've enjoyed this story - let me know!