5 comments/  40272 views/  6 favorites

My Second Time

By: Lovinhose



I hope you've been enjoying my previous stories thus far. As you know (unless you HAVEN'T read them) my stories are short, true, and to the point, so you may enjoy them that much quicker without reading long drawn out writings. So here is another true story for your enjoyment. 

This was my second time (well, technically my third, as the first guy fucked me twice within ten minutes). From back in the days of placing ads in the personals section of a local paper (the youth of today has no idea what the pre-smartphone era was like), this story takes place. It was somewhere around '96 or' 97, and not too long after the first time. I was married to my first wife at that time, later becoming my ex (but ironically, we got divorced because SHE cheated on ME, having had no idea that I was cheating on HER, by getting fucked by men while dressed in women's clothes. But isn't it cheating only if it were another woman...?). 

So, having really (REALLY) enjoyed my first time, I placed my ad in the paper, and waited, and hoped for, the replies to start coming. Of course I received plenty of replies, just not many serious (or sane) ones. But alas, finally, after a couple weeks if I recall, I got one that I went with (who agreed to meet and could host, the latter of which was, and still is, a must). He lived alone, was about the same age, and was close to where I lived. The shorter the time away from home the better as to not arouse too much suspicion. He was also a crossdresser, which peaked my interest even more. 

For the week prior to the agreed upon date, I was nervous as hell, just like I had been leading up to my first time, and every time thereafter. The nerves never go away, it feels like the first meeting every time. You just don't know what you're getting into until you get there. I've had sex with 19 men to date, the next one will be number 20! Hoping to make this happen very soon, but unfortunately, sometimes the dry spell lasts a year or more. That's not good, but thank goodness for porn and masturbation. And thank goodness for Craigslist too! Sure wish they'd been around back then; I'd be WELL over 19 by now. But better late than never! 

So the day finally came. The day dragged on at work, of course, the anticipation of what would happen later that evening predominantly occupying my mind. I had again made up another story about helping a friend or meeting some guys from work. I had to keep my stuff hidden away, my first wife knew but disapproved of my dressing. So I kept my stash all stuffed away in my toolbox in my basement. We lived in an apartment and had a shared basement, and I would often go down there and change, sneak over to the other side of the basement (someone else's space, so quite risky but so much more erotic), and rubbed one out. Left a lot of DNA in that basement, never getting caught, but came real close a couple times. Just adds to the thrill, and a much more powerful orgasm! 

But on this day, my stash would make it out of the toolbox and into my car for an evening out. Following the directions he gave me (no GPS's back then either, I'm feeling old), and arrived at his apartment. I rang the bell and he buzzed me in. It was a two-family unit, he was in the upstairs apartment, and was waiting atop the stairs dressed in a hot minidress, nylons and high heels. We went inside, he saying he couldn't wait to see me dressed. We talked for what seemed to be too long (I wasn't there to talk), before he finally suggested I change in the bathroom. I changed into the same red velvet dress I wore during my first time, a purple teddy, black fishnets and black 4" strapped sandal 'fuck-me' shoes. 

At this point, I had very little experience, as this was only my second hookup with a guy. I asked if I could ride, he agreed, and I tried. I got on it but it was too painful (now I can ride a baseball bat but not back in the early days). We moved to the floor and I got on all fours. He entered me in what was to be my very first doggy fuck! It hurt as well, but I was going to go to the end. No matter how much it hurt, it was still an amazing feeling, a big cock stretching my asshole to the point of never before. In and out, I couldn't wait for him to finish, and at the same time, I hoped it wouldn't end! 

Eventually (and sadly as well) he came, his cock pulsating in my ass, I could feel it against the ring of my anus. I told him I wanted to fuck him now, but as with most guys, nobody wants to GET fucked after they cum. I look forward to the opportunity to GET fucked AFTER I fuck someone else. I guess it's called 'flip' fucking. I so love getting fucked that I'd have no problem doing that. So as usual, I took care of myself, but certainly was not leaving disappointed! There have been plenty of hookups that WERE disappointing, a 'failure to launch' type of thing, but the majority of my hookups have been successful and memorable, and I'm glad to finally share them with other like-minded people. It's nice to be able to be honest, to share my life experiences, and not be judged as society judges people who engage in this type of lifestyle. They just don't know what they're missing! 

As always, I hope you have enjoyed reading. This was as accurate as I can remember, being so long ago. I might follow with another story if I get enough requests to do so. Thanks to everyone who has read my stories, and special thanks for the kind positive comments, I'm glad you enjoy what I share with you!

My Second Time



All participants in sexual acts are at least eighteen year old, or older.

*****

Wow! I was her "Boy Toy!" That's what Claire had called me before shooing me out and home after our evening of torrid sex.

Let me tell you, there was very little sleep for me that night. Jeez, I tossed and turned and fondled an almost constant erection until compelled into getting up around 2:30 to jerk off. 

Even then it wouldn't go down as the thoughts of what had happened to me yesterday and various scenarios of what else could or would happen to me in the future kept me wide awake and horny as hell.

Around four am I reminded myself of the promise of more that coming afternoon and finally dozed off.

The next morning I did show up at school and realized that nobody seemed to think I looked any different or kidded me about the cock-measuring contest I'd been in the day before. 

With a start I remembered that none of the guys involved went to my school, and Foxy, the #%$!@&! that got me into it went to St. Michael's several blocks away. 

It was kind of depressing NOT to be able to share the adventures with anyone, but I'd promised Claire I wouldn't, and wanting more of her, I kept my word. 

I did find myself looking at the girls somewhat differently, a little more confidently perhaps, and the first two classes raced by.

I cut my pre-lunch class as scheduled and arrived at Claire's promptly at 11:30. We were to have lunch together. I was concerned because I had to be at work by three and even though Claire had assured me we had plenty of time I was still nervous.

My erection was harder than Chinese arithmetic, and I had great difficulty hiding it from the moment I left school until arriving at Claire's.

It may have been my imagination, but I could swear several women stared at my crotch as I walked along the street to Claire's apartment. In later years I came to learn that some women have perfected the art of undressing a man in the most discreet manner imaginable and have an innate sense of a man's sexual arousal. In short, it's very possible they knew I was horny as hell.

I knocked at Claire's door and heard her call out that the door was open and to come in, which I did. As the door closed behind me, Claire called out a sultry greeting from the bedroom. 

I stumbled, tripping over my own feet getting in there. She was fully clothed and gave me a soft, quick wet kiss on the lips and backed away to sit on the bed as I stood in place awaiting instructions.

I couldn't help but touch myself as Claire raised her leg high and started to remove her black boots. I never thought to wonder why she was even wearing them at the time so mesmerized was I with the generous view up her skirt she was providing.

Giggling, she glanced up at me and chided me. 

"Sweetie-pie, aren't you going to wait until we're both ready?"

"Huh?"

"You'd be ungentlemanly by starting without me," she continued, her face a mask of seriousness; her lacquered red fingernail pointing at my groin.

I must have blushed scarlet because she looked me in the eye and smiled. The peal of delightful sounding laughter poured forth from her slender, swan-like throat. I managed an embarrassed smile and looked down at my shoes, managing not to look at the formidable bulge in my pants.

"Sit there," Claire said rubbing her cheek. "I want us to be able to see one another."

And I sat there, enthralled with her beauty and remembrances of the night before. I gaped at her, wanting to leap across the space separating us and bury her beneath me in a passionate embrace.

"Just open your mouth and let the words come out Frank. It's easy. Go on, talk to me."

I was awash in thoughts of tongues and tits and cunts and cocks commingled together. I knew full well that she sensed my desire for I certainly sensed hers. And, there was that scent I was breathing in, unmistakable in its feminine allure. My prick was never harder

(Well, that's a judgment call, alright?")

"So talk to me!"

"Err, what?"

"Just talk to me. I want to hear your voice."

"I... I don't know what to say."

"Just open your mouth and let the words come out. Come on Frank... it's easy."

"Okay," I said nervously, "you're more beautiful today than you were yesterday."

"Oh! Frank," she gushed, obviously pleased. I had surprised her.

"How nice," she beamed, "You're gonna do just fine."

Claire's fingernail traced a circle on my upper thigh, "Keep going," she said with a wide smile.

"I think I'm gonna cum in my pants before long, I'm very ... excited, Claire."

"Well don't!" She said, her divine lips forming a pout.

I had a vision of the day before while racing out for condoms; my knees began to buckle.

"I want you to save it for me. For me, understand?"

I knew she wasn't angry, but she was deadly serious.

"Yes, but how?"

"Concentrate. Think of something different."

"Like what?"

"Do a math problem in your head. You like baseball, think about yesterday's game. Something like that."

I got the point. I concentrated on my driving manual's sample questions and answers. Somehow my prick began to thaw. (This little exercise has helped me numerous times since. Another thank you note never sent.)

"You have such a beautiful face yourself," she said softly. "Did you know that?"

I could swear she was purring. I touched my face as if to discover it for myself.

"Angelic," she murmured happily, as her fingernail roamed along the side of my dick. 

"But with a cock as formidable as Michael the Archangel's sword. Oh yes, I'm a lucky girl to be getting fucked by you. But don't let that go to your head Frank."

Heaving her hips from the bed and pulling her skirt up around her waist, she asked, "Tell me how you got yourself involved in that weird contest?"

I stared in awe. To this day I can still envision Claire hooking her thumbs under her black tights and pulling them down. Oh, God she was beautiful!

She raised her legs, kicked the tights off, and for the second time in my life I gazed through her revealing panties at the mysterious area withheld from me until yesterday, and marveled at the wonder of it all.

"Come on, tell me," Claire repeated as that tormenting fingernail circled the head of my cock like a vulture idly inspecting its prey.

So I did. After I finished Clare was silent for a moment.

"With friends like that you don't need enemies. I'm flattered that I was the lucky one to take you home with me," she said in a soft undertone, and passed the tip of each middle finger quickly over the tip of her tongue like someone about to turn the page of a book. Then those same moistened fingertips traveled down to the areola surrounding each nipple and moved purposefully round and round causing both to quickly rise up like mini-erections.

Of course, I had never seen anyone do that before, and my own erection loomed forth prodigiously against the fabric of my pants.

Claire looked down at it, and licking her lips, said, "Oh, my! Off! Off! Get them off!" she cried, obviously as excited as I was.

"I want to see. I want to suck!" she grasped her left breast with her right hand and pulled on the nipple with the other as though masturbating.

The only sound in the bedroom was my belt unbuckling, followed by the lowering of my zipper. Then pants dropped to the floor with a thud. 

In my haste, I almost ripped my shorts off. Soon afterward, I was bending down and hobbling on one foot as I removed my socks and shoes while standing. Lastly, I pulled my sweatshirt over my head and tossed it casually on a nearby chair and stood there, penis erectus, ready to conquer the world.

Claire put her feet firmly on the floor and wriggled out of her panties. Her dampened pubic hair sparkled from the reflected light pouring in the window. That image is also vivid now, as I pause from my writing ... her fingers wandered under the elastic and peeled those lime green panties from her body. She was completely naked now, except for the lime green panties in her hand. I recall envying the shadows hovering upon her skin. I had this overpowering urge to lick and kiss her everywhere, though I still harbored certain reservations about things that were considered taboo by the guys.

Claire's breasts were full, particularly in contrast with her narrow waist and thin arms, their nipples, still taut from her earlier massage pointed upward. Her pubic hair parted naturally, affording me a glimpse of her vagina whose swollen lips awaited me. Soon, I thought, soon. I took a firm grip on myself.

With a giggle, Claire twirled her underpants over her head on one finger round and round until finally they flew off her hand and landed at my feet.

"Lucky shot," she said, giggling some more as she sank slowly before me to the floor. I picked them up and held them to my nose and inhaled. The musky odor assailed my nostrils. I closed my eyes and found myself heady with lust.

"Why not wear them over your face?" Claire asked, smiling.

I pulled them over my head.

"Can you smell my pussy?" She asked lewdly.

"Oh yes. Yes I can. And it's a wonderful smell Claire," I said reassuringly, surprised that I could see her clearly through the gauze-like material.

"Good, because I smell something good myself," her eyes gleamed and she licked those wanton, salacious lips of hers seductively.

I was ready to bust a load and began stroking my cock, rubbing the early seepage around and into my purple knob. As I manipulated myself I became aware of her breathing, which had intensified.

Claire moved a couple feet away from me and said, "Now watch me, but don't touch me, understand?"

I nodded.

"Look at what you did to me Frank."

Claire's thumbs were hooked inside her pussy and she was spreading it wide apart. The hot pink color leapt out at me.

"I'm opening my pussy for you to see my clit." Her voice dripped sex.

My hand froze, my jaw dropped open and my eyes bulged out of my head!

"See, Frank, it's swelling from me touching it."

I must have been drooling by then, but I still heard Claire whisper huskily; "Look at MY hardon Frank."

Oh, I did, I did.

"Watch as my finger rubs all around it..." Claire licked her lips. "Mmmm mmmm, I'd love to feel you suck it into your mouth Frank," she murmured, becoming the siren luring the thirsty sailor.

"Want to feel your tongue pressing and flicking at it ..." she hissed snakelike and curled her tongue then pulled it back. 

"Mmmmmm, Frank, she croaked, "gimme a lick here baby."

I dropped to my knees and crawled closer.

"You're probably thinking that it's disgusting," Claire crooned to me as I moved within inches of her. Most guys wouldn't ever think of doing that ... for a girl; although they don't mind a girl going down on them, do they Frank?"

Mesmerized, I could only nod affirmatively. That's exactly what the guys had said to me. Somehow it didn't seem fair to me. I reeled closer, drawing in her pungent aroma, entranced by the liquid covering her fingers, which were now oozing in and out of her tight salmon-colored cavern.

"You know Frank, when my thumb nail rubs against it, like this ..." and she flicked it just so. "Mmmmm, it tingles Frank! Oh, and it throbs to ... can you imagine how gooood it feels?"

Both my dick and my mouth were drooling as I nodded.

"Frank, if you wanted to you could put your head right between my legs right now ... " 

Claire's thighs parted some more.

"Mmmmm what a wonderful thought," she sighed.

"Okay," I whispered hoarsely."

"Would you?" Her voice grew deeper.

"Wha... What do I do?"

"Mmmmmmm...Frankie baby, I seem to be soaked here." Claire seemed not to have heard me as she inserted her middle finger and seemed to stir it around. Quivering, she pulled her finger out and offered it to me.

Without hesitating, I accepted it. My tongue licked it feverously, trying to overcome the taboo and assimilate the taste. Slowly Claire withdrew the finger. There had been no awful odor, no repellent taste, rather I found her to be sweet and sour at the same time.

"Watch me Frank, she cooed, and thrust three fingers inside her.

"I can feel them Frank... three fingers... " she shivered as I placed a hand on her shoulder to maintain my balance.

"Mmmmmm, so tight... why look Frank, they're... " she sucked in her breath, "stretching me, Frank. Look how open I am for you baby."

I inched closer to her, my nose brushed against her pubic hairs.

"I'm rubbing my clit Frankie."

Oh, yeah, no lie there.

"Oh look at me baby, look at me. I'm so fucking wet baby..."

Another revelation, I loved hearing her say "fuck." 

I kissed her belly surprising Claire, who drew in her breath. My tongue did a lap or two around her belly button.

Claire rasped, "Oh yes, baby! Come on down!"

I began a series of small, light kisses that could only lead to one place.

Her fingers fluttered in front of my face capturing my attention. I paused in my kissing, focused on those fingers. Claire raised herself up slightly and slid one hand under her ass, the fingers of her other hand moved fleetingly upon her clit.

I resumed my nipping kisses. She moaned saying, "Let me tell you about my pussy Frank. There's a lot to it, ya know." She was panting hard and I could hear the squishing sound her juices made as she plied those fingers in and out of her cunt. Then I realized fingers on her other hand were moving in and out as well, but from her ass!

I continued my trail of wet sloppy kisses into her bush and then I arrived at her pussy. A tentative lick... a taste bud savoring... and I went for it.

"Mmmmmmm, baby, that's nice! Claire likes that very much!"

"You taste good, Claire."

"Ohhhhhh, God, sweetheart!"

"Is it okay, Claire?"

"Of course it's okay, baby," she said, lowering her face and kissing the top of my head.

I continued kissing and licking, emboldened now, I took her large lip into my mouth and sucked as hard as I could.

Claire responded by grasping my head with both hands and holding my face in place.

"Ohhh fuck! There!" she instructed, Right there!"

"Ohhh, do it! Ummmm, yes, yes, yes! Oh, Frankie... there, ahhhh! Right there!"

My prick was so rigid I started to rise to get some relief, but Claire called out in a hoarse whisper, "No, stay put!"

I putted. Sucking her enlarged clit as she'd instructed me.

"There!" She called suddenly. "There! Oh, right there! Oh, GOD that feels so nice!"

I stopped using my mouth for a moment, letting my fingers slip inside her teasing that spot she was raving about. Curious, I spread her legs further apart, to obtain a better view of her pussy.

With the blinds drawn the room was almost dark except for several thin rays of sunlight spilling in and falling across the bed. Two rays highlighted her wet vaginal furrow until I blotted them out by lowering my face once again.

I don't know how long I pleasured her this way. Claire moaned all the while as I licked her, sucked her, nipped her, and caressed her. My fingers roamed upward, discovered her hardened nipples and plied them, bringing forth even louder moans. Claire's arms were thrown back behind her head, which was shaking from side to side. Her hands held tightly to the headboard, and when I slowly bit down into the flesh of her clitoris, she screamed and went rigid, moaning, "No more, no more, no more. It hurts. No more."

I hesitated for a moment then began sucking her clit again.

Claire moaned. "Oh, God. I'm going to come again Frank. Stay there. Watch me come. Watch me now."

I withdrew far enough to see what she was talking about. Both her hands were working almost frenziedly on her cunt. Her ass rose up from the bed, only to fall back then rise up again. Claire stuck her tongue out trying in vain to lick her breast, but she could only reach the beginning of her cleavage, where drops of her saliva pooled and flickered faintly in the dim afternoon lighting. 

She didn't seem to mind this failure.

Then she was smiling, as she calmly said, "I'm there! I'm there! I'm there! Mmmmmm! So good! Oh, so nice."

The rest of her words vanished in the scream of joy erupting from her as her body spasmed from the final chords her fingers played out upon her clitoris and cunt. Slowly, Claire came to rest, until finally she turned her hands palms-up upon her thighs and let her head fall back gently on the pillow so she was staring up at the ceiling. She smiled contentedly and purred. Slowly, her chin came down until she was able to look at me again.

She just lay there, looking at me. I glanced furtively at my hardon. The pre-cum was oozing copiously from the tip.

"That was wonderful," she said in a hoarse voice. "Thank you. You know, for the first time you were... ummm, very, very good. And thank you..." she didn't finish the sentence.

I must have looked at her questioningly.

"For watching," she explained. "It was so much better with you watching. I hope you don't mind."

I shook my head. My prick jerked in the air of its own accord and Claire broke out in a gale of laughter. I looked at her pussy, sumptuously wet and swollen, veiled now with tiny ringlets of dampened pubic hair.

Claire spoke softly to me. "Would you like to try it?"

She saw me staring between her legs and said, "Not me silly. You."

"Oh, I... I couldn't. I mean... I."

"Go on," she said firmly as if knowing I would and only needed to be prodded a bit.

"Really? You really want to watch me jerk off?"

"Yes I do. I really and truly want to watch you do it."

I stood up and took myself in hand.

"Ohhh, look at you," Claire cooed. "Can you really grip it in both hands?"

"Uh, yeah, I can."

With some pride I quickly demonstrated that indeed I could grip it with two hands and there was still about two inches protruding above my fingers.

"I've never seen a cock as big as yours," she whispered, obviously impressed.

"But after the contest I should have known, but still... you make quite an impact on me Frank. Your cock is... formidable. Yes formidable.

I ached for her hand to replace mine, but lacked the courage to ask.

"Go on, Frank, crank it up."

I leaned back slightly thrusting my pelvis at her face, which was only two feet away and began to jerk myself off.

"Claire?"

"Yes?" Her voice already possessed a dream-like quality.

"Can I lick your nipple while I do it?"

"No." But she paused as if giving my request further consideration. "Oh, all right, but keep stoking and don't bite them they're quite sensitive right now."

She stood beside me and presented a breast to my mouth. She even cupped my balls for a minute or so. But I was thwarted from my blissful sucking as Claire pulled her stiffened nipple from my pouting lips and sat down at my feet.

"I'm sorry," she said, "I can see you. I'll let you play with them later, okay?"

I continued with my slow, mechanical stroking, occasionally running my thumb across the head of my uncircumcised prick, tickling the sensitive head.

"That's so beautiful," Claire husked. "Thank you for letting me watch."

"Never done this before," I stammered.

"You've never masturbated before?" She asked incredulously.

"No. Had someone watch me. Normally I'd have come by now."

"I've heard guys sometimes form a circle and have contests to see who will finish first and who will be the last to come."

"Really?" I said. I'd never heard of such goings on.

"Ummm, for sure. But girls don't do that."

"That's strange," I responded, "I thought both sexes were pretty much alike when it comes to sex."

"No, not at all. Girls might get down and dirty with one another though."

I wiped beads of sweat from my eyes and forehead, and asked, "What do you mean?"

"I mean they eat each other. If the group is large enough, say four girls, and they haven't paired off, they might form a circle while eating one another. That's called pulling the train. "




My Second Time



"Look at me," she said, and I did. "I see little droplets of cum on your cock. Wet yourself with them. Pretend you're inside my pussy. I'm still soooo wet. Go ahead."

"I had never heard or dreamt anyone talked like this before. I did as she suggested and squeezed my prick tighter then ever before. My hand became a blur as I felt my scrotum beginning to tighten. My heart was pounding. Sweat trickled down my nose and dropped to my chest. My head was ready to burst.

I watched as Claire's eyes followed my movement - from my hand jacking off to my eyes. Eyes glazed with lust, I focused on her cunt - incredibly turned on by how she looked and how she was acting.

Then I heard her say, "Now, Frank. Now, Frank. Come on me Frank, shoot all over me Frank. That cinched it. Sperm cannonaded from me. Ribbons of white ink poured forth adorning her lips, chin, neck and hair.

My cries of pleasure merged with her yelps of delight. Then all was quiet except for my panting and gasping for air.

When I reached out to her, she wriggled away, crying out, "Not yet, not yet."

Only when I stopped panting did she close in on me and kiss me. I felt her breath leaving her nostrils and breathed deeply through my own to capture and savor it.

We kissed and kissed and kissed again. Our mouths were one for an interminable time before she broke away and laughed happily.

"You're not finished yet." Claire said provocatively, touching my nose with her finger.

'What?" I asked, puzzled.

"Your jism. Lick it off me." And she leaned away from me in order that I might see for myself. With a nonchalance that amazed me, (well, I had tasted myself before.) I sought out the morsel adorning her lower lip and licked it off. 

Holding her head in my hands I removed all traces of my sperm from her face, then kissed her and found her tongue laving mine as though fighting for the spoils of war. It was great fun and when it ended I regretted not having spewed forth even more.

It was a momentary regret, for her tits were bobbing unnervingly close to my mouth. Claire giggled as her hand cupped a breast and held it directly in front of my mouth. Eagerly my lips closed tightly upon her nipple. I was in heaven.

"There are two of them you know," she crooned into my ear.

"Ummm, I know."

"Don't make Mama sore there, be nice and take the other one for a while, then I have a real treat for you."

I followed her suggestion and idly wondered what kind of treat she could have that was better than this. Ahhh, such is the grand foolishness of youth. George Bernard Shaw was right on the money when he wrote, "Youth is wasted on the young."

Then I felt an incredibly warm, wetness envelope my prick as her mouth descended upon it.

"Ummmmmmmmmm," she moaned with satisfaction.

"Ahhhhhhhhhhhhhhh." I groaned in gratification and sank to the floor beside her.

Claire made a slight adjustment to her position and continued with her blowjob, which by the way, is still unmatched in my experience. It seemed to me that Claire continuously changed her sucking technique. I mean, one second she was sucking the very life out of my cock as she went down on it. Then she'd pause and lick, suck, lick, varying the pressure from her lips. Then she was concentrating on the head of my cock, exploring, finding every sensitive area possible.

I lay there in a dream-like state as she raked my testicles with her nails and then kissed them and finally drew them into her mouth. It was exhilarating. It was rapturous. It was fucking great. Once again, I erupted with volcano-like force, this time into her insatiably parched mouth and she swallowed every drop.

We stopped and had some orange juice to help refresh us, then light conversation followed about what I wanted to do with my life. I was surprised to discover I had no idea what I wanted to do. Deftly Claire planted fertile seeds in my brain as my dick hung panting, trying desperately to renew itself.

"Oh, damn, it's one o'clock already," she said, and reached out and ran her fingers across my hairless chest. "We'd better get going again."

She pinched a nipple then ran her hand across my stomach. "Ummm, you're so smooth and sexy."

"Me, sexy? You've gotta be kidding." I really thought she was teasing me.

Claire giggled and said, "If you only knew how sexy you are to a woman your ego would be impossible to deal with. Please stay as sweet as you are Frank.

Promise me."

"I'll certainly try Claire." I managed to gasp as she began to play with my nipples. I was surprised that it felt so good, and told her, "That feels nice."

"That's only the start." Claire said, bending over and licking a nipple with her tongue. She played with them for a while then reached down and gave my cock a playful tug. "I'll bet you're already to go again," she smiled. "Good, I like that."

"I am?" I said.

"You are. Take my word for it."

"I am," I said, reassuring myself for the second time in the last minute, still somewhat surprised at my tumescence as I settled down and grabbed a pillow for my head.

Claire laughed and moved up my chest to reach behind my head, caressing it with her long nails. For some inexplicable reason she kissed me, softly at first then harder and harder. Her mouth opened and a warm, wet tongue forced my mouth open and invaded mine.

I had swapped spit before, but never under these circumstances. Instinctively, I followed her movements and tossed in a few of my own. We were both moaning with the lust of it all.

"Put it in me Frank. It's time to fuck me. Fuck me good Frank."

She seemed to be pleading with me. I hurried to comply, only I couldn't find her hole fast enough to suit her and she gripped me in her fist placed me inside her.

Oh God! I wriggled my skinny ass and found her so wet that I slid in to the point our pubic hair was mingling. I still remember the sensation as her cunt wrapped around me.

"Fuck me Frank! Fuck me hard!"

We went at it like two 'energizer' bunnies. Her face was covered with a sheen of perspiration, her mouth hung open and her tongue lolled out. Claire was panting like a dog, eyes wild, filled with a crazed lust. I laughed thinking how I must look to her and then forgot about thinking and concentrated on fucking as her vaginal muscles squeezed me tightly while I plunged in and out.

"Yesss! Frank, fuck me harder!" She wailed close to my ear. Then lavished it with warm, slippery, moist kisses.

I gripped Claire's ass with both hands and slammed it too her. Her stomach pounded against me as she wrapped her legs around my back, bonding us closer than before. I realized she'd brought my wild thrusting under some semblance of control and I began to pace myself. Her moans grew louder and I realized she was clawing my back with her nails. Later she would tend to these slashes with the utmost care, but then she was tearing my back apart.

I didn't care about the searing pain. I kept slamming my pelvis against hers, driving my cock home. I could feel the eruption building inside me as her juices flowed from her pussy, around my cock and down her thighs, ending up in the crack of her ass.

"I'm gonna come Claire!"

"I am coming and coming and coming, but please don't stop! Oh, God I don't believe this!"

We thrashed about for another minute and then I couldn't hold off any longer and came in a torrent. Claire wriggled under me, thrusting her pelvis about, wringing the last vestiges of her climax from her body.

We lay silent and still, me still on top of her prone body.

Both panting before Claire gently rolled me off her and bent to take me in her mouth. She licked me clean and then kissed me. I tasted my jizm on her tongue and sucked it up, swallowing it knowing this act would bring Claire joy.

It did. She hugged me close and whispered, "You'd better get ready for work. You can take a quick shower if you like."

"No," I said. "I'd rather go through the day with your odor in my nostrils and your taste on my lips." I meant it as I said it. I hadn't reckoned on Claire's take though.

"Oh, Frank, that's the nicest thing any guy ever said to me. You are a romantic!

Give me another kiss you... you wonderful lover you."

This wondrous affair lasted five weeks.

That it ended when it did was my fault. Claire taught me so much I thought I'd be irresistible to the girls at school. 

It was one of the worst decisions I ever made. I ignored her. And eventually she found someone else; and I never knew who. As for me, my prowess as a lover went for naught with girls my own age. They wanted a guy with a car. They wanted a jock. I was a has-been jock now, working 32 hours a week to earn enough for a car. 

I went without pussy for the rest of high school and beyond. For two long years my fist was my solitary lover, until a year out of high school I got lucky again. But that's another story.

I love you Claire, wherever you are. I think of you often. And you will always be youthful, beautiful and sensual to me. I love you and thank you for everything. I wish I'd handled things differently, but that's life.



My Second Time Being Milked



Author's note:

This is the second part of the "My first experience being milked" story. Since I spent a lot of pages setting up the story and introducing Hans and Annie in the first part, I decided to jump into the action from the start in the second part. I tried to find an editor, but no one responded.

*****

I looked down at the blonde head bobbing up and down and wondered how I could have been so lucky. My balls contracted and I let out a low moan as I filled Annie's mouth with my cum.

"Thanks honey. I really needed that," I said.

She licked my cockhead a few times and then wiped some cum off her chin with a finger and smiled at me. "You are welcome. I know things have been hard since we came back, but I am glad things are looking better."

She lay down next to me on the bed and snuggled in close. Her face was facing the window and her ass pushed against my cock. She was naked, Annie always slept naked. I cupped one of her breasts and slowly massaged it. She was warm and smooth, and so different than my ex wife. One of the reasons was that Annie was much younger, only twenty four, while my ex wife was close to fifty. I was forty five, but feeling like twenty five. Annie had that effect on me.

"You know that the big day is almost here," she said.

Christ, I thought, her birthday. I had tried not to think about it. Not that I don't love her, but she only wants one gift and that gift is something I don't like.

"Yeah, I know," I said.

"Are you nervous?"

"Not really, it won't be the first time."

She giggled, "No, it will be your third."

I let go of her boob and kissed her cheek, "What about a nice little cute puppy instead?"

She found my cock behind her and gave it a squeeze. "No, I want to milk you properly, and you promised you would let me."

I sighed and laid back again, letting her have her way with my cock, which grew hard again. Her ass felt very inviting so I adjusted my position and slid inside her wet pussy. 

"Oh, that feels good, honey," she purred, and pressed herself harder against me.

I figured it was a good way to escape the inescapable, and grabbed her boob again while I fucked her from behind.

After showering together we sat down for breakfast. It was a sunny day in late October. We had been back in the states for about four and a half months. When we got home from the flight there was a letter waiting for me from my wife's lawyer where he said that she was going to sue for full custody of our son. The following months had been grueling, but now it was finally over. She had lost and I had the right to see him every other weekend. Then the bitch moved five hundred miles away, so it could only be ones every month. I didn't have the energy to go to court again, so I talked with my son and decided to do the best we could with the shitty situation. He is a mature fifteen year old, and one hell of a student.

During this time Annie had been a great support, not only emotionally but she had helped me with my construction business so I could work with my lawyer. She didn't know one thing about cement, wood, screws or nuts (pun intended), but she was a good administrator. My guys were a bit flirty with her in the beginning, but she handled that by telling them she was out of their league and she only had eyes for me. They sulked for a few days, but when they noticed she got more jobs for us, and therefore more income for them, they took her in as part of the gang. Annie was a great negotiator; she could talk a man into redoing his entire kitchen when he had just asked us for a cupboard. 

I live in a University town somewhere in the middle of America. I wasn't born here, but moved to this town with my ex wife. She had been a professor at the University up until she moved away. It's a big place, I think there are some twenty thousand students and they leave their mark on our town. There are bars and burger joints on every street corner. In the summer you can walk down the street and enjoy watching coeds in tight t shirts not wearing any bras, and with long firm legs. I love it here. 

"I'm going to that flea market today," said Annie, after we finished breakfast.

"Oh, OK. I thought you were coming with me to the office."

"No, you can handle it."

I put on a puppy face, and said. "But I will miss you."

She gave me a kiss on the cheek. "That's good, because it will be so much more fun when we see each other later."

We left at the same time, her on a bicycle and I in my truck. She would bicycle anywhere; I guess that's her Swedish part. Luckily, our town is flat like a pancake so it's easy to get around on a bike.

I met up with some customers in the morning and in the afternoon I spend time with my foreman going over new projects. It was hard to concentrate. Every hour that past brought me closer to the milking. 

Annie loves to milk me. I have only done it twice and that was in Sweden when I first met her. I didn't know at the time that she had a fetish for it. It's not that it scares me. It's more that I don't like the feeling of having her finger up my butt. The sensation when she rubs my prostate is fantastic, but still it's not my thing. I love normal fucking, licking pussy and having my cock sucked. Maybe I am old school, but that's just the way I am.

When I drove up to the house I had rented I saw Annie standing outside talking to a man with a pick up.

"Hi honey, Tim here, was nice enough to drive me home with what I bought."

"No problem, have a nice day."

Tim got into his pick up and backed out. On the other side of the pick up stood Annie's bike and what looked like a table.

"Why did you buy a table, don't we have enough?" I said.

"It's not any kind of table, it's a portable massage table, and I bought it for us."

I put my arm around her shoulder and pulled her close. "That's why I love you. You always think about me, and now you can give me one of those Swedish massages every night."

She laughed, and said. "Not so fast. That table needs a bit of work, but when it's ready it will be my milking table."

I stepped away from her. "You're what?"

"Come here," she took my hand and pulled me along with her. When we stood beside it, she continued. "I will make a hole where your cock will hang down. I can sit on the floor under and just open my mouth and let your nectars drop down into my mouth."

"And who will make the hole, not me."

She picked up a bag next to her bike and opened it. "Roger was nice enough to show how to use this," she was holding an electric saw in her hand.

"Oh, I see. Well, while you play Bob the builder, I will be having a drink. See you later."

While I mixed a Gin Tonic in the kitchen I watched Annie working. Roger had been a good teacher. She was done by the time I had had my first sip. She folded the table and brought it with her.

"Make me one of those," she said when she walked into the kitchen. She had left the table in the hallway.

"How did it go?"

She drank some from her glass. "I'm very pleased; I think it will work great. You will find out tomorrow evening."

The following day was Annie's birthday. I had bought her a necklace and some clothes. I woke her up with breakfast in bed and sang happy birthday to her. Then we fucked and I left to work. She wanted to do some more work on her table she said.

After I finished work I went by a supermarket and bought some wine for the evening together with two steaks and a pre made salad. I had some potatoes at home; I would throw in the oven and make us baked potatoes. While I drove home, I thought about the table she was building and how much it meant to her to milk me. I thought it was an obsession, almost like an addiction. I had asked her where she got the need to do it from but she couldn't give me a straight answer. In the end she had put it down to control. She liked being in control of my orgasm, and she loved to suck the pre cum directly from my cock. 

"I'm home," I called out when I closed the door behind me.

"I'm in the living room."

I dropped the bags in the kitchen and went to look for her. I found her standing by the massage table in the living room and when I walked up to her and put my hand around her waist she kissed my cheek.

"What do you think?" she said.

The table looked like any other of its kind. Except there was an oval hole in it. "I guess that's where I will put my cock and balls?"

"Yes, dear and I will be underneath sucking you."

I looked at the thing and I realized it was impossible to do what she wanted. "You know you can't reach my ass from under there?"

"Of course I can. I will stick my hand through the hole behind your balls."

"It's too small."

She stepped closer and looked at her handy work. She stuck her hand through the hole and shook her head. "Fuck! You are right."

"Sorry honey, I knew you worked hard to make this." Inside I was smiling.

"Don't worry, I have a plan B."

I took her around the shoulder and led her to the kitchen. "And what would that be?"

While helping me with dinner, she said. "Do you remember that vibrator you bought me?"

"Uh-hu."

"Well, I thought that we could use that."

I looked at her from where I was standing by the stove. She was at the kitchen table uncorking one of the wine bottled.

"How would your vibrator help us out? You still won't be able to reach around."

With a loud plop the cork came out and she grinned at me. "You will use it."

"What?"

"Yeah, it's perfect. I will help you insert it, but once it's inside, all you have to do is to slide it in and out."

An image flashed before my eyes of me fucking myself with her eight inch dildo. "I don't think so."

She stood and poured two glasses and took one over to me. "Oh, honey, it's my birthday, and you want to make me happy, don't you?"

Her hand that wasn't holding her glass rubbed my cock through my pants, and he came awake.

"Of course, babe. Anything for you."

"Thank you," she said and kissed me on the cheek.

All through dinner I kept thinking about what was to happen. Annie noted my lack of attention to what she talked about. "Hans, are you OK? Are you freaking out because I asked you to use the vibrator on yourself?"

I took a sip of my wine, and said. "Yes, I am. You know I don't like it."

She took my hand in hers. "Honey, you like to jerk off, don't you? This is almost the same thing, just that, well, you stick a fake cock up your ass." She said the last words with a crooked smile.

"Very funny. I'll do it, but only because I know how important it is to you."

"I love you."

While Annie went to look for her vibrator I got undressed and lay down on the table. It was narrow and I didn't have much room to move. I could only spread my legs a few inches to either side before they dropped off. My cock and balls fitted perfectly in the hole she had made, so that was a relief at least.

"Here we go," she said when she came back.

In her hand she held the vibrator and in the other a tube of lube. She was already naked and her firm boobs hardly moved as she walked towards me. Her pussy was shaved apart from a thin line above her clit.

"Be gentle," I said.

She kissed my ass cheeks and then began to rub lube around my anus and inside it with her finger. The feeling wasn't bad, it tickled a little and I must admit that my cock grew in size. I heard the low buzz when she turned on the vibrator and when the tip touched my anus it tickled even more. She moved around the area, pressing down gently and after a few minutes I moaned. Yes, I know, I say I don't like it, but at the same time the feeling is very intense.

"I think you are ready," she said.

"If you say so, darling."

She put the tip of the vibrator right on my anus and began to press down. I did what she had taught me and breathed slowly. When it slid in I gasped and almost bit into the bed. There was a sharp pain as the cockhead opened me and then it diminished as my anus adjusted around the shaft which was thinner.

"God, you look sexy," she moaned.

"I don't feel very sexy."

"Oh, shut up, I know you like it, you just play hard to get."

Like I said before, the feeling isn't half bad, but you feel like a complete idiot with a dildo sticking out of your ass.

"Hold here, and if you want, you can move it back and forth a little," she said, and placed my right hand on the toy.

It was an odd position and I wasn't very comfortable. I soon forgot all about it because Annie's lips closed around my own cock and her hand played with my balls. I couldn't see what she was doing, but whatever it was, it felt fantastic. She actually sucked on my glans, while using her hand to pull down from the base towards the head. I say actually, because during a normal blowjob the girl will slide her lips up and down the shaft. Annie kept her lips around my cockhead and sucked. 

The vibrator was doing wonders to my prostate and after a few minutes I got that feeling of taking a piss, but I wasn't. It was a tickling feeling inside my cock and I knew the pre cum had begun to flow. I heard how Annie took my cock out of her mouth, and then she said. "Mm, you taste fantastic, keep going for a little while longer and then you can take it out."

I did what she asked and I could hear how she swallowed under the bed. I counted to three hundred and then pulled the vibrator out of my ass. As soon as I did, a whole other type of pleasure had come over me. Annie knew what I had done and instead of just sucking, she began to move her lips up and down my shaft while massaging my balls. My orgasm grew and when I came it was an eruption of cum.

"Wow, considering it wasn't a perfect set up, I say it worked pretty well," said Annie when her head showed up next to mine. She had cum on her cheek and a drop in her hair, and was wearing a big smile.

"Happy birthday, baby," I said.

She hugged me and then pulled me off the bed onto the floor. My cock was still semi erect and she used her hands to make me hard again. Then she straddled me and slid my cock inside her warm and wet pussy.

"Mm, you feel good," I moaned.

"You make me feel good, big boy."

She rode me until she heard from my breathing that I was close to coming and then she switched and I slid into her ass. She gasped once, twice and then she buried her face in my neck and moaned. "Fuck my ass, Hans; I love how you fuck my ass."

When I came for the second time that night I kissed her on the mouth and cheeks, and said. "You are the horniest woman I have ever met."

She kissed me back and pushed herself up, using her hands against my chest. "I have an idea. I hope you like it."

I became suspicious. "What is it?"

"Well, the table works fine, but the problem is that once you get horny enough, you don't want to or can't move the vibrator correctly so the flow of milk stops."

"Oh, I'm sorry. It's kind of hard to concentrate when you have a rubber cock up your ass and a beautiful woman sucking your cock."

"No need to be sarcastic, darling. We will simply find someone to help out."

"Like who, Roger?"

She laughed and hit my shoulder with her clenched fist. "No, stupid, I thought about another girl. Someone young, and eager to try new things. I could check out Craig's list and other similar sites for a woman who is looking for a couple to play with."

"Yeah? And what happens if she turns out to be a psycho and kills us?"

She got up and took my cock in her hand. "This thing needs more attention, and it's obvious that just you and I can't do it. We need help. Think about it. Wouldn't it be nice to fuck a sweet eighteen or nineteen year old pussy?" she gave me a wink.

Don't get me wrong, I love young women, but I already had one. I loved Annie and I didn't feel the need to bring someone else into the relationship.

"Not really, you are young enough for me."

She kissed my forehead. "You are so sweet, but you are a terrible liar. Give me a week or so, and I'll find us the perfect plaything."

Then she lowered her head and wrapped her lips around my cock. The girl loved her milk.

During the following days I spent a lot of time thinking about Annie's plan to bring someone else into our sex life. I guess I was happy about it being a woman and not a guy. Before I met her, Annie was part of a free spirit group in Sweden, which her boyfriend at the time had started. She had been with men and women during that time, both individually and in orgies. I on the other hand had no such experience. My ex wife and I had had a regular sex life as married people have, once or twice a month and always the missionary position. When I was single and in college I almost had a three-sum with two girls, but I was too drunk and passed out before I even got my pants off.

I spent some time on the internet and found out that milking was popular in the fem-dom niche. I watched a couple of videos with women in black leather leading around men with masks that they bound to beds or wooden crosses and then milked. It did not look like something I would enjoy and I prayed that Annie wouldn't find one of those to take home. 

Two weeks after Annie's birthday, she called me at work one afternoon. "Hi, honey. What time do you get off today?" she said.

"Around five. Why?"

"We have a date; meet me at David's pizza house."

"What are we celebrating?"

"Nothing, we are going to meet Ashley."

"Oh, and who is she?"

"She is interested in learning how to milk a man."

"But.."

"See you later."

After she hung up I sat and stared at the phone. Ashley, how old would she be? Did she like to dress in leather and whip her man before stuffing a twelve inch dong up his ass? The thought made me shiver. I hoped Annie knew me well enough not to bring someone like that into our relationship.

I arrived at David's just after six and when I walked in I saw Annie in a corner booth. There was someone else sitting on the opposite side of the table, but I couldn't see her face since she had her back to the entrance.

Annie stood when I approached, and said. "Hans, this is Ashley."

I looked down and the face that looked back at me and smiled was not what I had expected. She was young, a lot younger than Annie, and she looked like someone's secretary. Big glasses, conservative hair cut, plaid skirt, sensible shoes and a white and blue pullover. Her eyes were dark brown and when she had smiled, she had straight white teeth.

"Nice to meet you, Mr. Kallberg."

Her hand was warm and dry in mine, and small. "Nice to meet you too, Ashley. Don't call me Mr. Kallberg, Hans will do."

"Sure, Hans."

"We already ordered the food, but if you want a drink, that is our waitress," said Annie and pointed at a blonde standing by the bar.

I got her attention and signaled I wanted the same as Annie, a beer in a frosted glass. I wanted something stronger to keep my nerves in place, but I didn't want to seem like an alcoholic in front of Ashley.

"How did you meet?" I said, breaking the silence, after I had sat down next to Annie.

"On Craig's list," said Annie.

"I put an ad in a few weeks ago, about being with an older couple and Annie answered it. We exchanged a few e-mails and found out that I was looking for the same thing as you," said Ashley.

I looked around us and the closest people were a few tables away. I leaned in across the table towards Ashley, and asked. "What did Annie tell you?"

I thought I saw her blush for a second. Then she drank some of her wine, and said in almost a whisper. "She needs help milking you."

"Oh, and what else?"

"Not much, just that she had made a table and afterwards realized it was impossible to do what she wanted."

"Have you done anything similar before?"

She giggled. "No, nothing like it, but it sounds cool."

"Cool, eh? Annie, are you sure this is such a good idea?"




My Second Time Being Milked



Annie took my hand in hers. "Of course it is, darling. Let's have a nice dinner and then go back home and try out the table."

When the food arrived Annie asked Ashley to tell us a bit about herself. She was not from town, but from a smaller place some hundred miles away. She was doing her first year in college, majoring in finance. She wanted to go into banking after graduation. She had an on and off boyfriend, but promised us that he wasn't important in her life. Annie asked about her previous sexual experiences and she said she had lost her virginity before graduating High School with an older guy and since then had been with three guys. She said she wanted to expand her sexual experience and hoping that by being with us she would learn new ways to give and get pleasure.

All through the conversation I was staring at her. She looked at me a few times and I guess she might have felt uncomfortable. I just couldn't let go of how she looked like. I knew she was over eighteen, but she didn't look like it. When she stood to go to the bathroom, I saw that she was short, no more than five-five or six. 

"She is too young," I said.

"Nonsense, you should have seen some of the things she wrote me, she is a horny little thing, that's for sure. She is perfect. Just relax and stop staring. By the way, did you see her boobs?"

"Not really, I was looking at her innocent face. What about them?"

"I think they are big. The pullover she is wearing is hiding them, but you just wait until she is naked."

"Uh-hu."

After I paid, Annie and I got into my car and Ashley followed in hers. It was a good looking Japanese car, some kind of hot hatchback. Not the kind of thing I had expected her to drive. 

When we arrived at our house Annie suggested we all take a shower together. Ashley nodded and began to undress in the living room. I was the last one to be naked. I had a hard time concentrating on the buttons on my flannel shirt while Ashley was taking her clothes off, one item at the time. Under the pullover she wore a sports bra, and when she took it off her boobs exploded in my face. Well, not literally, but what I had guessed were A cups, turned out to be C cups. Under her skirt she wore white panties with a lace trim. And when they came off I saw a nice little triangle of pubic hair above her clit.

"What do you think," said Annie, and pointed at my cock.

Ashley walked over to where I was standing and without a word took my limp cock in her hand. She had hardly touched it when it rose and I was standing there with a hard on. She wrapped her little hand around it, and said. "Nice, I like the thickness."

I must have blushed, because Annie said, "don't be shy, Hans. Let's go to the bathroom."

It was cramped in there. We stood in the bathtub and soaped each other's bodies. I did Annie while Ashley did mine, and at one point Ashley offered to do Annie's back again. I thought that there was a moment of understanding between the two women. Maybe Ashley was into girls too, I thought. I wouldn't mind watching her going down on Annie. In fact, that sounded much more fun that being fucked in the ass.

"On the table, honey," said Annie, when we were back in the living room. It was dark outside, but she had drawn all the drapes just to be on the safe side. 

I did what she said, and put my cock through the hole. I lay there feeling like a complete idiot.

"This is what I want you to do, Ashley," said Annie.

"Take this vibrator and make sure it has plenty of lube on it. Lube your finger and slide it in carefully. When he begins to moan you can gently introduce the vibrator. If he says stop, you wait a while."

"OK and how far should I stick it in?"

Annie giggled. "It's eight inches, and I'm pretty sure he can take it all, but you only have to insert it two or three. That's where the prostate is."

I became concerned. "Listen, don't get carried away, Ashley. Two or three is just fine."

Annie slapped my ass, and said. "Don't be such a chicken, honey."

Then she sat down under the table and I felt her hands on my balls and cock. It was semi erect but under her touch it hardened fast. Just as I was relaxing I felt Ashley's finger probing around my anus. I didn't feel any sharp nails which made me relax. She found my tight hole and began to push.

"He is tighter than I thought."

"Keep pushing," said Annie.

Her finger slid in and I breathed in and relaxed as much as I could. There was a difference between the two women. Annie knew where to go with the tip of her finger but Ashley didn't.

"You are looking for a walnut size thing, it's on the side of his tummy," said Annie.

She found it and I must have gasped. "You got it," I heard her say under the table.

"This is so cool. Let me know what is happening," said Ashley.

I closed my eyes and to be perfectly honest, it was much nicer than I had thought. Ashley was gentle and her little finger rubbed my prostate and it didn't take long before I heard Annie say, "Here it comes."

"What?" said Ashley.

"His pre cum, keep going."

I heard more than felt how Ashley looked under the table. "Oh my god, just look at that."

"What?" I said.

"The liquid is just coming out of your cock by itself, Annie isn't touching you."

The pleasure I felt was so intense that I hadn't noticed that Annie had let go of my cock. That strange feeling, like an itching in my cock, was becoming unbearable. Then Ashley decided to insert the vibrator, and turned it on.

What had been a nice comfortable pleasure in my ass, turned into an explosion of it. "Oh my, oh, oh, that is intense," I moaned.

Ashley began to slowly fuck me with the vibrator. "Do you like it, Hans?"

"Yeah, I do, I actually do."

"Good, because you are not dripping anymore, it's running free," I heard Annie say.

She wrapped her lips around my cockhead and began to suck. My breathing increased and I could hear myself moaning loudly. I almost felt ashamed for showing the pleasure I was feeling.

"Can I try some?" said Ashley.

Annie let go of my cock, and they changed places. "Are you OK, she said when she continued to slide the vibrator in and out of me. 

"It's very intense, but I love it."

Ashley didn't just suck on my cockhead. She took as much of me inside her as she could, and played with my balls.

"Annie, I don't think I can hold back much longer."

She kissed my ass cheek, and said. "It's OK; you can come whenever you want."

I stopped trying to hold back, and said. "Ashley, I'm coming soon."

"Mmm," was all she said.

"Oh, yes, yes, here it comes," I moaned.

To my surprise Ashley didn't let go, instead she sucked harder and deeper and when I did shoot my load I heard her swallow as fast as she could. Then there was a wet sound and I heard her breath hard. "God, that was a lot of cum."

Annie slid the vibrator out of me and I managed to turn around on the narrow bed without falling off it. Ashley was standing now and holding on to the bed. There was cum on her lips, her cheek and on her chest. Annie walked around and wiped some of it off her boobs. Then she licked it off her finger. I closed my eyes and thanked my lucky star I had found someone like her and she had found someone like Ashley.

"When can we do this again?" said Ashley after we had showered, this time individually.

We were sitting naked in the living room. Annie and I were on the sofa and Ashley across in an armchair. She had her legs pulled up under her, but I had seen her cute little pussy. I wanted to fuck her so hard, but I wasn't sure how to say it. After all, this had been Annie's idea and for her benefit.

"Sure we can. What do you think, Hans?" said Annie.

"Yeah, of course."

"Today is Friday, what about Sunday afternoon? I need to study tomorrow," said Ashley.

I looked at Annie, who shrugged her shoulders. "Sunday it is."

"Cool. I have to go, but thanks so much, and Hans, you have a very cute butt, and I hope that one day, if Annie is OK with it, you will fuck me."

I was stunned. I just stared at her when she got up and put on her clothes. When she opened the door to leave, she turned and blew us a kiss.

"What a wonderful young girl," said Annie, when Ashley had closed the door.

"Yeah, she is."

She got up and was on her way to the kitchen when she turned around. "Would you like to fuck her?"

I was taken aback by the blunt question. "Well, yeah, I guess."

She grinned at me. "You dirty old man."

"C'mon, I'm not that old and you brought her here."

"I know, I was just teasing you. Sure, you can fuck her, but I want to watch."

Annie brought a bottle of wine and two glasses and after a while I got up and made us some dinner. We ate naked in the living room watching TV. My ass hurt a little, and my balls felt empty. I wasn't sure I would be ready for Sunday, but how could I say now to two sexy women? I had changed my mind about milking. It was something I could get into, especially with two women taking care of me. What I didn't know, was that Ashley had her own game in mind, and Annie would love it.

We had just finished lunch on Sunday when there was a knock on the door. Annie went to open while I cleared the table. I was a bit nervous, which was strange since I honestly looked forward to what was going to happen. I had spent most of Saturday day dreaming about plunging my cock into Ashley's young pussy. Annie had caught me with a vacant stare and had asked what I was thinking about. Being an honest man I told her and she laughed and said she was looking forward to watching us.

"Hi Hans," said Ashley, when she walked into the kitchen.

"Hi, you look great," I said.

She was wearing a mini skirt and a tight t shirt under a leather jacket. On her feet she had a pair of boots that ended just below her knees. She looked very hot.

"I have brought a gift. Well, it's a present for all of us to enjoy," she said, and held out a paper bag to me.

I put it on the kitchen table and looked inside. "Oh, this is a surprise."

"What is it?" said Annie.

I took out the box that was in the bag and showed it to her. "I guess Ashley wants to get close and personal," I said.

"Oh my god, a strap on, that is such a nice thing to buy," said Annie taking the box from me.

"I thought it could be fun, you know. We could both fuck him, and with the strap on it's our movements that bring out the milk. Not a battery driven toy," said Ashley, and her eyes sparkled.

I was glad to see it was not as big as the vibrator. It was shaped like a real cock, but according to the box it was seven inches long, and it looked a bit thinner.

Annie opened it and took out the harness and the dildo. She attached it to the harness and held it up in front of her. "This is so cool, I get to have my own cock," she laughed.

"I think we should skip the table, and just use the floor," said Ashley, and began to push the low table away from the sofa. Under it was a thick rug. Annie helped her and before I knew it, we had enough space to move around. Ashley helped me off with my clothes while Annie went to the bathroom for the lube.

"I'm so looking forward to fucking you. It's a fantasy I have had for a long time. I want to know what it feels like," said Ashley, while pulling down my boxers.

My cock sprang out and it was already hard. She grabbed it and stroked it slowly while looking into my eyes. "I want you to stick your cock into my pussy and ass today, Hans. I want you to open me up. I'm tired of the young guys and their inexperienced dicks."

"Just look at you two. You have to wait until I have had my fun," said Annie, who walked in just as Ashley knelt in front of me.

"Please, let me suck him," she begged.

"No, not yet. Hans, I want you to lie down on the floor, face up. I want to look into your eyes when I fuck your ass."

I did what she said, and Ashley was nice enough to find a pillow from the sofa and put it under my head. Then she got another and pushed it in under my hips.

Annie knelt between my legs and poured plenty of lube on my cock and balls. "Ashley, why don't you stroke him while I lube his ass?"

The young woman knelt beside me and took my cock in her small hand. She had a good grip, and began to stroke me while watching intently how Annie used her middle finger to lube my anus. I had to lift up my hips for her to reach, and I wasn't really clear on how she planned to fuck me in that position. 

She slid a finger inside me and after a few minutes another one. I guessed my ass was used to it by now, because it didn't feel strange and it didn't hurt a bit. It just felt good when her fingertips touched my prostate. She continued to rub it and when Ashley smiled, and said. "Look, he is dripping," she pulled out her fingers.

Ashley lowered her face and licked the first few drops of my cockhead. "Mm, it tastes good."

"I need you to put your legs up on my shoulders, Hans."

I did what she said, and when they were in place, she leaned forward so my knees bent and I felt the dildo touching my anus. "Wow, do I feel like a bitch now," I said with a grin.

They both laughed, and Ashley said. "Relax, you are no one's bitch, you are a great guy, who let us fuck you and drink your milk."

Annie adjusted her body and said. "Let me know, when it's in place."

"Now," I said.

She pushed with her hips and my already lubed ass opened up and she slid in. "Oh, this feels much better than the vibrator. There is no pain at all," I said, with surprise in my voice.

Annie began to move with slow thrusts, not pushing in more than a few inches. "This feels so hot, Hans. I can't believe I am actually fucking you."

Her skin against mine, her movements and the dildo running over my prostate made me moan with pleasure. Ad to that Ashley's hands on my cock and I was close to coming in minutes.

"Annie, stop, stop or I will come. I want Ashley to do it, and you drink."

The women changed position and when Ashley entered me, she was not as gentle as Annie. She took hold of my hips and went to town with hard and long thrusts. There was still not much pain but after a while my legs began to shake, and an amazing feeling spread from my balls through my entire body.

"Just look at that," said Annie, pointing at my cock.

I lifted my head as much as I could, and I saw clear fluid coming out of my cockhead and running down my shaft. She lowered her head and licked it off. Then she moved up and took me in her mouth. 

As I watched her suck my cock, her right hand moved up over Ashley's stomach until it reached one of her boobs. When she pinched her nipple, Ashley moaned and closed her eyes.

Annie sucked a bit longer and then let go of my cock. She moved around so she was behind Ashley and massaged her boobs and kissed her neck. The younger woman turned and they met in a kiss. 

"Oh, Annie, can he fuck me now, please," she moaned.

"Are you ready to fuck her, Hans?"

I was so horny I didn't know what to do with myself. "Yeah, I'm ready."

"Then do it."

Ashley pulled out of me and moved up so she was straddling me. She was just about to grab my cock when Annie said. "Let me help you."

She guided my cock to Ashley's pussy lips and when I felt her skin against mine, she lowered herself slowly. My cockhead pushed in between her lips and when it entered her, she sighed. "Oh, fuck me, Hans. Fuck my young pussy."

That did it for me. I grabbed her hips and moved her up and down until I came inside her. Her fingers dug into my chest and she threw her head back, and came loudly. When she had calmed down, she got off me and lay on the floor and gasped for air. Annie moved up and lowered her head towards her swollen pussy lips. 

There is something beautiful about two women being together. I lay there next to them, watching how Annie ran her tongue up and down Ashley's little pussy slit. I thought she would be exhausted, but she only needed a little bit of attention to come back. They moved into a sixty-nine with Ashley on top. Watching them turned me on, so I got up and drove my cock into Ashley tight pussy from behind. My balls slapped into Annie chin and face. When my cock was wet from her juices I pulled it out and slowly pushed it into Ashley's tight asshole. When I was all the way in, she turned and looked at me. "I love it; I hope you liked it as much when I fucked your ass."

"I did, and I want both of you to do it again."

"Just as soon as you have enough milk built up."

Again she came loudly and when I pulled out and shot my cum over her ass, she said. "That feels so good." 

Then she used her hands to smear the juice all over her ass cheeks.

When Ashley had left Annie opened a bottle of wine. It was after eight at night and we sat on the sofa. She poured two glasses and put the bottle on the table. Then she took my hand in hers. "Hans, did you enjoy what we did today?"

"Yes, I did, I actually enjoyed it a lot."

"I'm glad you did. See, I told you that milking was something fun."

"Well, I don't know about the actual milking. If I'm not mistaken, I dumped the first load into Ashley's pussy and the second on her ass cheeks."

"You are so cute. I had plenty of pre cum while she fucked your ass. She was very good to be a first timer."

"I guess she is eager to learn."

"Next time, I will let her have the bulk of your milk and you can fuck me in the ass."

I kissed her and held her tight. "I can't wait."

Over the next months we would meet every weekend and the women would fuck me and sometimes each other with the strap on. What did I learn? That being milked is a fantastic experience if it is done by the right person or persons. I'm sure I will have new experiences with new women soon. Annie is talking about going on a cruise over the winter Holidays and I caught her checking if there were any swinger's cruises available.



My Second Time with Mom



NOTE - Well, there's an old saying which goes, "Incest is Best" and boy is it the truth. Following my first time with my mom, I did feel a little guilty, but after what recently happened, there is no doubt in my mind. Without question, my mother is the greatest fuck I've ever had and my only hope is that if any horny mothers and sons read my story, they decide to give into the lust.

After our first time together, my mother and I refrained from sleeping together for a while. I think my mom's conscience had gotten the best of her. No question that she had enjoyed riding my cock, after all, her pussy nearly exploded. But even so, she is a church going woman and very proper. No matter how badly she wanted me inside of her, she was doing her best to resist the urges.

Not so for me. Things have become quite strange for me since that fateful day. I'm more distracted at work, spending most of my time fantasizing about my mom's big pussy and ass. And my relationship with my girlfriend has deteriorated. I'd honestly rather be fucking my own mother than my girlfriend. More than one time, when having sex with her, I've closed my eyes and thought of my plump mommy and her hanging titties.

Fortunately for me, my mother is not completely immune to her desires and we continue with our daily "feedings." To say the least, my mother breastfeeding her adult son is kinky but she rationalizes it by saying it is a "bonding" experience. Once in the morning and once more at night, I get the luxury of sucking on those huge mammaries. And without failure, every time, I get an instant erection. My mother has developed a little schedule. I suck on each tit for 5 minutes and that's it. I guess she figures by making it a regimented process it's not really incest or "wrong." 

But aside from these daily sessions, my mother and I have not had any true sexual contact until the other day, and what a day it was!

Our home state was recently bombarded with a major snowstorm, it hit right before Christmas. Now my mom hates to drive, so when it snows, she absolutely refuses to leave the house. Unfortunately for her, on the morning of this mini blizzard she was called into work at the pharmacy and I had the pleasure of driving her. The plan was simple, I would drop her off and then head off to work myself. I would pick her up as soon as I got home.

The roads were treacherous that day so traffic was nearly at a standstill. To help me cope with the traffic and all the tension that goes with it, I decided to put on my favorite AM radio talk show. This show tends to get a little raunchy and some of the things they discuss are perverse if not completely sick. It's not uncommon for them to talk about a woman's breast size, her ass or even her vagina. You get the idea, it's not politically correct. Mind you, prior to my "first time" with my mother, I would never have thought of listening to the show with her around. But what the hell, I just got done sucking on her fat tits for ten minutes, I didn't think she'd mind the crude radio show.

Just my luck, on that morning, the disc jockeys were playing a game called, "Guess Her Bra Size" and were brining in random girls off the streets and having them stand there in their bra and underwear, to determine what cup size they were. I'm a "tit man" and hearing about a busty girl standing in her bra and panties turns me on. I was wearing my suit (headed to work) and the pants were a relatively thin fabric. After about 5 minutes of hearing about a young girl with a 40D bust and thong underwear, I noticed myself developing a slight erection. As the girl described her tits further and how they "bounced like crazy" during sex, my slight erection became a full-fledged boner. I know, I know, rather pathetic but I was horny as a toad. Sucking my mom's tits but not being able to fuck her had me really hard up. It didn't take much to get me aroused.

Normally, getting a boner in front of my mom would be the ultimate humiliation but obviously things had changed between us. So, I sat there quietly, with my hard on in plain view. As we neared the pharmacy, my mother took a casual glance at me and noticed my bulging cock. She giggled slightly to herself and looked out the window. I was praying to myself that she'd take my cock and suck me off until I passed out but I didn't think I'd be so lucky. Little did I know!

When we finally arrived my mother told me to drive around back where the dumpster was. I thought this was a little odd because there were no parking spots back there nor was there a back entrance. Rather than ask questions, I did as she said.

There were no cars in sight and the wind was howling with snow coming down in sheets. I parked the car next to the dumpster and looked at my mom, "Well, we're here, you better go Mom, you're going to be late and I have to be at work soon."

My mother said nothing. She undid her seatbelt and looked down at my cock, which was slowly losing it's "hardness." She looked at me and gently began caressing my crotch. It felt good, really good. After several moments, my dick felt like it was going to explode. She stopped (much to my dismay) and began to take off my suit jacket and tie. She slowly unbuttoned my dress shirt and began to rub my chest and circle my nipples. Loan moans were coming from her mouth. All I could manage to do was lean my head back and close my eyes. I needed release and I needed it soon.

After several minutes of fondling me, my mother began to undo her blouse and she said, "Son, suck my titties." She took off her bra and her fat, saggy titties fell beyond her naval. I thought my mother's request was odd. Normally, she'd refer to this as "feeding time" - it sounded less sexual. But I did as she asked and began feverishly sucking on her heavy hangers. They smelled like perfume, it was perfect. I sucked on her enormously fat nipples and licked her huge aereolas. My mom leaned her head back and began to breathe rapidly. I was sucking like a wild man, it felt so good, so right.

After about 5 minutes of this, my mom began to talk dirty to me, "Oh son, that's it, that's it, suck momma's tits, oh baby boy, suck me." My mom had not spoken to me like this since our first fuck and it turned me on. I decided to keep it up. I slid my hand down her pants and felt her cum drenched panties! My mom was turned on and I knew I had to keep going. I began to finger her massively hairy cunt which was coated in her juices. She spread her legs further apart to allow me better access and she began to whimper with pleasure. I took a break from her tits and began to slide her paints down her waist. I lowered my face down to her vagina and slid her panties to the side.

I was in heaven. My mom's cunt was hairier than most men's heads and her juices were literally seeping from her vagina. Her bulging belly hung over her cunt, it was more than I could take. I plunged into her pussy and began to thrash my head around, greedily lapping up her juices and tonguing her clit. I don't think my mom was prepared for it because she yelled out as I sucked on her twat. Her tits hung low and swayed back and forth as she arched her back, calling out in pleasure, "Oh my god, oh, uh, uh, uh, oh god, oh shit."

I could not believe how I was turning her on. She began to grab hold of her fat boobies and brought one of them up to her mouth. My mom began to lick her own nipple. At that moment, I considered myself to be the luckiest person alive. I kept eating her pussy as she began to lift her fat, cellulite filled ass and wide hips off the seat. She was thrusting her cunt into my mouth, literally fucking my face! It didn't take long before her fat pussy exploded, covering my face with her juices.

My mother was out of breath after my oral assault. Her nipples looked as if they could cut glass. Meanwhile, I had some pre cum on my dick head and I needed my mom to take care of me. My mom looked at me and gave me what I wanted, "It's your turn baby."

I closed my eyes and leaned back and as she slowly slid my pants off. My cock nearly took her eye out, it was as hard as a rock. She got on her knees and leaned across the console, with her fat tits hanging low. I nearly shot a load right there, looking at her in that position. She took my cock in her mouth and began to bob her head up and down. As she sucked harder, I could hear her massive tits slap up against her belly. I was losing all self control and I yelled out, "Oh shit mom, oh god yeah." I shot load, after load, after load in her mouth. My mom gagged on most of it which was dribbled down onto her tits and nipples. By far, that was the most powerful orgasm I ever had up to that point.

Making things even more erotic was the fact that we were doing this in my car. Having sex with my mom and risking being caught turned me on even more! When she was done sucking my cock, my mom whispered to me, "Crawl into the back seat." I then knew that I would fuck her again.

I awkwardly managed to get in the back seat and sat in the middle, with my 9-inch cock high in the air. My mom stumbled in after me and straddled my knees. I began to fondle her big titties, which were covered in my cum, and she slowly stroked my cock. After a few seconds, she held my cock and began to position her big twat and ass over it. I closed my eyes in anticipation of the pleasure. My mom slowly lowered her massive pussy over my cock. Her messy wealth of pubic hairs tickled my dick head and I could hear my cock sloshing through as she sat down on me.

When my mom had taken my entire cock, she moaned and her eyes closed. Her tits began to flop up and down as she slowly grinded her ass and hips on my cock. I wasn't able to hold out long at all. The feel of her tits on my chest, feeling her belly and tits slam against my stomach and watching her eyes roll to the back of her head were too much. I grabbed hold of her hips and began to meet her thrusts, I was fucking her quite hard. After a few more seconds, I was spent. I shot several loads of cum into her twat and moaned in delight. My mom tossed her head back and yelled, "Oh, oh, oh, oh, oh, ah, ah, ah, yeah, yeah."

My mother fell onto my chest and stayed there for several minutes. We were both exhausted, covered in sweat and our own juices.

She then looked up at me and said, "Let's just play hookey and skip work today."

We managed to crawl back into the front seat and make our way back home in the ice and snow. While we didn't fuck each other again that day, we had a few more "feedings" than usual. I spent most of the afternoon sucking on her udders.

Well, hopefully I will be lucky enough to enter that big old pussy again. You know what they say, third time is the charm! If I get that lucky, I will be sure to let you know.

And interestingly enough, my 19 year old sister is home on Christmas break. Hmmmmmm, maybe she's into breast feeding! Who knows?