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Mikey and Bobby Ch. 01

By: cleanly_shaven



It all happened by accident. We never intended to be the lovers we are today. My friend Mikey and I (Bobby) were always really close. We did everything together. I'm a trust fund baby and no one knows that except for Mikey, and didn't tell him until I knew I could trust him. It took years for me to do it because I didn't trust anyone after I had moved here, knowing that if people knew that I was going to get millions of dollars from my real parents, who died when I was too young to remember, after I left home that all kinds of fake people would want to "befriend" me. People are real fake and phony here anyway, which leads into what I was getting at.

And we literally did everything together. My parents had a guest house in the back that they never used and Mikey and I overtook it. We did everything that two 18 year old boys would do back there, including watching porn. At first we would take turns watching it on the big screen TV, but eventually we would jack off together. We would have some porn going on in the background while we would be playing ping pong, and then something would catch our eye. For me, it was usually when I would see some hot bitch getting DP'd. I would love watching a chick getting two cocks in her pussy at the same time. I would get real turned on when I saw two cocks up some hot bitch's ass. I remember specifically stopping what I was doing one night and walking right over to the couch to watch this girl get dick after dick up her ass and pussy, and it was usually two at the same time. She was covered in cum and that put me over the edge. I started jerking off right there and Mikey joined me. I could see his cock in the glowing light of the TV and it was amazing. He had this skinny, little body and this monster of a dick. I wanted to look at it more than the porn on the screen. He caught me looking at it and continued to jerk his big dick off while he was moaning with pleasure. His cock made me really horny, and came to the sight of it. I came so hard all over myself that night, thinking about my best friend's big cock. We hadn't said anything to each other about it since.

Mikey and I are pretty much the same build. We're both about 5' 9" and rail thin. We weren't built to look like men. I have longer, blond hair, while Mikey had just plain short black hair. His eyes were amazing. Even before I thought him fucking me, I always thought that his crystal blue eyes were sexy, especially with his black hair. Even at 18 and in our senior year of high school, we aren't big boys. We're skinny like girls. And that didn't help out our situation with the girls here at school. They were all into the beefy studs with muscles, and well, we just didn't have any.

Mikey always had this thing for this one girl at school, Mindy. She was really hot, I have to admit. Skinny, blonde, nice B-cup tits, tan...she was really hot. Mindy always Knew that Mikey had a thing for her and would lead him on and be friendly, but it would never lead to anything. Mikey thought differently though.

We were still both virgins and were nearing that last week of our senior year. Mikey was really insisting that he was going to get laid and he thought for sure that Mindy was going to give it to him. He kept telling me at school that she was becoming more flirty with him and touching him and laying her head on his shoulder during class and whatnot.

Mikey insisted that we go to this guy Shane's house that weekend because he knew that Mindy would be there at his house party. As usual, I followed Mikey's lead and went with him, even though I couldn't stand Shane or anyone that would be at Shane's house.

Needless to say it was a complete disaster. We got there and sure enough, a bunch of over testosterone knuckleheads were already drunk out of their minds and playing grab ass with each other. We would walk further into the house and once and a while someone else was bumping into us because they were pushing each other around. 

Finally we got out to the back where there was a path through the tree line into the lake area where others were at. We could see a campfire on the beach and people gathered around it. It was there that Mikey would witness exactly what he didn't want to see.

Mindy was there alight, but she was already straddled on top of some muscle bound moron and dry humping him right there un front of the crowd on the beach. People were cheering them on as they started to undress. I continued to watch as I saw Mindy's shirt came off, and shortly there after, her jeans. She was hot and I wasn't going to miss that show. She had the tiniest pair of light blue thongs on and she was grinding hard into that guy's crotch. The crowd got louder and then I witnessed something that I definitely didn't think I would see that night. That guy buried his cock into her pussy. I couldn't believe it.

I turned to see what kind of reaction Mikey was having, but he was already half way back to the house. I ran to catch him.

"Hey," I said. "I'm sorry what happened back there. I'll do whatever you want to do. Do you wanna go back to my house?"

"Whatever," he said. "Let's just go."

I drove the two of us back to the guest house. My parents were gone as usual. They were always gone to some fancy dinner party with all of my dad's work friends. They never cared to talk to me and I didn't really care since I had Mikey and the guest house all to myself.

We got inside and we immediately both sat on the couch. Mikey was still fuming mad and I could tell by the look on his face.

"Fuck that bitch!" he yelled. "Fuck all of those girls! I'm so sick of all of those boneheads fucking all of our girls all the time. Who cares if they lift weights. They're just going to beat them down the line anyway."

"It's alright," I said. "We're leaving this stupid place soon anyway and we won't have to deal with them again in our lives. I'm telling you, we can go wherever we want. I can buy us a house somewhere, anywhere...and we can say 'fuck you' to all of these chumps."

"You're right," he said. "But I still want to get laid though. I still want to fuck her so bad. You saw her, she would be so hot...that body, that blonde hair, that tanned skin..."

I thought to myself that I had all of the things that Mikey just mentioned. And my cock started to grow thinking about Mikey's big dick. I knew that he didn't care about me looking at his dick when we jacked off together that one time. I even remember him looking at mine when we did it, and I could have sworn that he even gasped when he looked at it like he wanted it. I had a crazy plan.

"Hey, let's just chill out, I'll put on some porn, we'll go have a cigarette, and we'll just have a chill night, ok?" I asked.

"Yeah, let's just chill here tonight." he said.

I turned on the TV and threw him my pack of smokes and I walked into the extra bedroom. Mikey walked out on the porch and lit up the cig. I walked into the bedroom and remembered that my older sister, who was not any relation to me, had some extra clothes that she had left here while she was at college. I used to put on her clothes just to feel like what it would be like to be a slutty girl sometimes and I would jerk off wearing her panties. It felt really good when I would do it. I grabbed the sluttiest pair of panties and matching bra I could find along with a white button up shirt and a plaid, really short skirt. I walked out into the living room with them in my hand behind my back. I found Mikey on the couch rubbing his dick through his pants watching the porn. I was glad he was still in the mood.

"Don't get mad at me, but I have a crazy idea." I said to him.

"Ok," he said.

I know you like Mindy because of her body type and hair and whatnot...I think you could still fuck her tonight..." I said.

"What do you mean?" he asked.

"I could totally look like her for you and I would let let you fuck me, Mikey. I know how badly you want to get laid before we leave here and I really want you to also. I really think I could dress up and be her for you if you wanted that." I couldn't believe that I just told him that.

He was stunned but he was obviously still horny since he was still rubbing his dick through his pants. "You would seriously do that for me? You let me fuck you? Anally?"

"Yes, Mikey. Ever since I saw your dick the other day, all I ever think about is your big dick." I was starting to get confident in what I was saying since I didn't see any hesitation form him. "Here is what I would wear for you," and I revealed the the bra, panties, shirt and skirt.

"Oh my god, Bobby! Yes! Go wear that for me!" he said as he tugged harder at his dick.

"Ok,' I said with excitement. "Give me a little bit, cuz I wanna make sure I do this right for you. My sister showed me how to apply makeup and I found some of her's in the bathroom the other day."

"Fuck yeah! Oh my god I can't believe we're going to do this!" He truly was excited and so was I. I was going to have that dick inside of me.

I ran into the bathroom and stripped down. I pulled the pair of purple, tiny, lacy thongs up over my ass and my dick. My dick was almost rock hard, so my dick was bulging out of them. Luckily, I had completely shaved all of my pubic hair earlier that night, so I was hairless down there. Next I put the bra on and I looked at myself in the mirror. With my long, blonde hair, I could almost be recognized as a girl right there. The makeup was going to add so much. I grabbed the makeup bag and began applying the eye shadow, then the eye liner, then the base and the blush, and finally the lip gloss. I took a look at myself and got really horny. I would fuck me too!

I put the shirt on and the tiny, plaid mini-skirt up over my little panties, took a deep breath, and walked out of the bathroom and into the living room where I saw my boy on the couch, bare-ass naked with his awesome, rock hard cock sticking straight up. 

"Oh my god, Bobby...you look amazing!" He said to me.

"It's not Bobby tonight," I said to him in my best girly voice. "I'm Mindy and I want you to fuck me."

I have watched plenty of girls on webcam in my day and even imitated them when they strip for you and I began doing the same for my new fuck buddy. I was bending my body so sexy for him and began to lose the shirt by unbuttoning it as I was shaking my little ass for him. I threw the shirt to the floor and got closer as I walked with a sexy strut over to him on the couch.

"Don't touch your cock while I strip for you. I want you to enjoy this tease." I said.

He let go of his monster and his jaw was wide open, gazing at my body as I did my little dance for him. I unzipped the side of the skirt as my mouth was wide open and I let out a big sigh as I let it hit the floor. I got down on all fours and crawled up to him and grabbed his legs. I whipped my hair and my mouth was so close to his cock now. My mouth was wide open and I held my breath and then let out a little moan as my breath hit his cock. I went to lick it but I missed it intentionally, just to tease him even more. I could see in his face that he was ready to fuck but I wanted him to get a nice tease so his cock would be so hard that he could just fuck me immediately.

I stood up and turned around so that my panty clad ass was in his face. I slowly squatted down so that his cock was barely rubbing my ass cheeks. It felt so damn good and I knew that he liked it too since I could hear his moans and sounds. 

I completely sat down on his cock and started to grind on it with my ass, getting his dick between my cheeks and sliding his shaft up and down my ass crack.

"Oooooo baby...do you wanna fuck me, huh? Do you wanna big your big dick in my ass?" I asked him.

"Oh god yes! I wanna fuck you so bad!" He said. I was so happy and I got a big smile on my face. I got up off of his dick and reached into the side table next to the couch where our jack off lube was. I poured a bunch into my hand and the next thing that happened was amazing. I grabbed that boy's beautiful, big dick and lubed him up. I used both hands at first and then used my left hand to hold the base of it while my right hand rubbed the lube all over his cock. My left thumb was placed right between the bottom of his shaft and where his balls met his dick. He moaned hard and gasped and I loved looking at him while I made his dick feel good.

"Ok baby..." I said as I stripped off my panties. "Fuck my ass with your big, hard cock!"

I turned around again like I was when I was doing my strip tease for him and spread my ass cheeks and lowered myself down for him. He grabbed his lubed dick and lined it up for my virgin asshole.

"Just get it in there, baby. Just fuck me already! I can't take it anymore!" I had no idea what got into me but I loved talking like a dirty whore.

"Ok..." he said. "Lower yourself."

I did what I was told and I felt his cock going up my ass. I loved it immediately and then completely lowered my ass onto his dick so that our balls were touching. Mikey's big cock was buried in my ass!

I started to grind on it. I loved the way it felt so deep in my ass. I always wanted to be a little slut at heart, and now I had my friend's huge cock all the way up my ass. I moaned like a little girl as I grinded on it.

"Oh my god that feels so good." Mikey said. I was glad to know that my ass felt good wrapped around that cock of his. This made my dick fully erect and it was sticking straight out. But like any good slut, I needed to get fucked, so I began to bounce up and down his dick.

"Fuck me!" I said each time I bounced up and down. "Fuck me! Fuck me! Fuck me! Fuck me! Oooooooo!"

He told me to stand up and I did, leaving his dick in me as we stood together. He fucked me real good as he had one hand on my stomach and the other one waist.

"Ah god yes, Mikey! I fucking love your big dick! You can fuck me anytime you want!" I yelled.

He started fucking me harder and faster. He was giving my virgin ass a real good fucking for it being the first time. He started to kiss my neck and I moved my head to let him while he fucked my ass. He could have done whatever he wanted to me.

"Oh fuck baby...I'm gonna cum." He said.

"I wanna feel it. I want you to cum so deep in me. Cum in my ass...cum in my ass...cum in my ASS!!!!!" I finally yelled.

He was fucking me so hard and fast that when he was cumming, his cum was going in my ass and flying out when he pulled back. All i heard was splashing and my new lover groaning in ecstasy as he came inside of my little butt.

He collapsed on the couch and I turned around to see him smile at me. My cock was still raging and I was happy cuz I wanted to save my load for something special. I didn't want to cum just yet.

*************

School ended shortly after that week and Mikey and I spent our summer looking for house to rent a long way form here. I had my money and we were ready to leave and start our lives as lovers. The nights in the guest house that summer were amazing. Sometimes I wouldn't even dress up and Mikey and I would wake up in the morning lying naked next to each other and we begin screwing around. I would usually grab his dick while he was still asleep and play with it till it got hard and then I would rub it on my ass and he would wake up and we would fuck. We did all kinds of positions. I would ride him cowgirl, or he would fuck me doggy, or standing up...it didn't matter.

One day I was fully dressed in some slutty lingerie that I had bought, garter, stockings, crotchless panties...and I was riding him cowgirl. My cock and balls were rubbing on his stomach while we were fucking and out of nowhere I came all over him. I couldn't help it. I just kept shooting my big load all over his face and chest. I hadn't came in probably over three weeks and I was an 18 year old. He thought it was really hot and kept fucking my ass and came up into me. I collapsed onto him and licked my cum off of his body. I approached his mouth and it was the first time we kissed. We kissed each other forever too. And it was all with my cum in each other's mouths. So hot!

One day we were looking online and we found a lake house that was a good price and that wasn't big our flashy. It was only one bedroom one bathroom and a living room and kitchen, but it had a great deck in the upstairs that over looked a private beach. This was going to be our new home and we were excited to start our new lives together. I also had another surprise for Mikey that I thought he would certainly enjoy!

Mikey and Bobby Ch. 02



By the time Mikey and I moved into our new little home of ours, I had gained the courage to go out in public as a girl. I had changed my name to Mindy (the name of Mikey's crush). We were in a new town, nobody knew us and he we kept a low profile by moving into our little place out of the way. Mikey loved my new look so much that we would occasionally hold hands and kiss in front of the people in public. No one ever thought for a second that I was a boy. In fact, many men throughout the town stared at me lustfully to the point where several times they got dirty looks from the wives and girlfriends. Mikey and I would just giggle and he'd usually grab my ass or do something just to make them even more turned on by me.

I'd usually wear something that all of the girls were wearing that was trendy, and just a little slutty. I wore a lot of faded low-rise jeans, tank tops that showed my midriff, things like that. I wore a lot of bright colors like pink, yellow and blue. Colors that would accentuate my long blonde hair. I wore long, dangling earrings or even big silver hoops. Pink lip gloss, blue eye shadow. I was really sexy. It felt good to go out and get that attention. Sometimes it would bother Mikey some. He always tried to hide it, but I could tell that he would have liked the attention too.

Our days were amazing. We usually spent them waking up in our king sized bed with all white covers and sheets. He would be naked and he would usually be spooning me and either I would wake up first and grind my ass into him or he would wake up first and be sliding his nine inch dick into my ass. There was usually enough cum or lube or both left in my ass to get his cock in me in the morning without having to wake me up to get more from my nightstand. So after passionate love making/hard core fuck fest, we would get up and do yoga at the local gym. My tummy was looking real tight and I loved wearing revealing clothing to show it off. My ass was tighter too and Mikey would just be behind during the class trying to hide his hard cock the whole time. My dick was tucked neatly between my legs. But that doesn't mean that I didn't have to make several adjustments during the class. I think that there were several women who may have seen me adjust my dick but were too afraid to say something to me. After yoga class, we usually grabbed fresh fruit, vegetables and usually fish from the farmer's market in town. Cook up a healthy lunch and eat, shower, take a nap in the after noon, then usually watch a movie, then he'd fuck my brains out and cum all over in me and on me. It was the most perfect life.

This went on for about nine months when Mikey started to change a little. He seemed bothered, so one night we were on the couch in the living room and I asked him, "Baby, I can tell something is bothering you. Tell me what's wrong."

"I hope that you can understand where I am coming from, Mindy, because this last year has been great," Mikey said. It's just that I feel like there is something missing for me.

Oh god. My fear of him wanting to go back to our hometown was here. what would I do with my life without my boyfriend? I was trembling. "Baby, no!"

"Oh, god, no Mindy, it's not what you think. I don't want to go back there," he said. I sighed a big sigh of relief, but I was blown away by what he said next. "You are so hot. You look amazing as this beautiful girl. People stare at you all the time. You make guys lust for you and that is such a turn on for me. I see how it makes you feel. You have never been this confident in your life and I envy that. Babe...I want it too."

I stared at him. I was bug eyed. Mikey wanted to be like me? He wanted to be a sexy young woman? My mind started racing. He recognized it and quickly started talking again before he thought I would get the wrong idea. "I've been looking online about changing into a woman and there's a great hospital that does everything to help you achieve womanhood and I want to go there."

"Baby, you want to be a woman?" I asked.

"Not a woman," he explained. I want to keep my dick, just like you. I just want to be as sexy as you and get all of that attention that you do. I think that if we both felt that men lusted for us that we would be even crazier for each other."

"Baby," I told him, "what's crazy is that I still find women so attractive. I find their bodies to be so perfect and amazing like mine that I still lust for it. But your cock is big and beautiful and perfect that I am so addicted to cock that I couldn't see myself going back to being attracted to just girls. This is amazing! You, as a beautiful woman, with a big dick! Oh my god, baby, I would be in heaven!"

I smiled so big and so did he. We embrace each other and kissed each other a long, passionate, hard kiss. I immediately started to strip him down, taking his shirt off forcefully then kissing his chest as I undid his belt. I moved down to the floor off of the couch on my knees and undid his pants and tugged at them till they came moose and I removed them. His cock was half hard and flopped onto his left leg and I immediately grabbed it at the base with my hand and started giving him one of my famous earth shattering, orgasmic blow jobs. His naked body was quivering, his head was thrown back, and his hands were running over his hairless chest. He moaned in delight from my lips, mouth, tongue and perfect movement around his nine inch, rock hard, pulsating, perfect dick. I knew if he was going to blow or not, and he was on the verge so I begrudgingly stopped sucking him and grabbed his hand to lead him into our bedroom. I dimmed the light and threw him on the bed and proceeded to take shirt off, undid my jeans as quickly as I could, and began tugging at them to take them off. They were so tight on my tiny body and thin legs that it wasn't easy. As soon as they were pulled down past my waist, my seven inch, fully erect dick flopped out over the top of my black g-string. I was as hard as a rock and there was already a stream of precum from the tip of my cock to a spot on the inside of my jeans. I tore them down, finally and jumped onto the bed and quickly straddled my hot ass boyfriend.

His cock was sticking nearly straight up, and my cock laid on his. Some of my precum dripped onto his cock and I took my index finger and began rubbing the precum on the tips of our dicks. I bit my bottom lip and stared into Mikey's crystal blue eyes as I did it. He gasped as I teased the tip of his dick. His precum was oozing out of his dick and there was enough to get our dicks lubed up. I took my hand and wrapped it around both of our cocks and began stroking them together. His balls were perfectly lined up with mine and base of our cocks rubbed together, as did our shafts and just under our heads. My hips gyrated as I stroked our beautiful cocks together. I moaned like a little slut and even squealed some as he began breathing harder and rubbing my thighs as he let me stroke us.

Our cleanly shaved dicks were both throbbing so hard that I could feel them both as I stroked us off. I took mine and stuck it right underneath Mikey's balls. My hand, still wrapped around his cock, began working the underside of the base of the shaft and my index finger worked the other side just below the head. Those were his two g-spots and I saw his balls begin to tighten. His face gave it away as he closed his eyes and began moaning really loud. I continued to work his two g-spots and pointed his dick at my tummy. two massive shots of his thick, warm, delicious cum shot me right on my tummy, some in my belly button and some just above where my pubic hair should be. Five more shots splattered all over my dick, including the head and shaft and my balls. There was so much of his sexy cum all over me that I began move all of it onto my hard cock. I was stroking my dick in my boyfriend's cum. He was unaware for what was about to happen. I slid down off of his legs and lifted them into the air.

"if you really want to be a hot little bitch like me, then you're going to have to take dick like me, baby!" I said to my hot little boyfriend. He looked at me lustfully and shook his head as to agree with me. I rubbed some of his cum on his asshole, inserting of my fingers as I did it. His hole took it with ease and I began to get excited about fucking him in his cute butt. He looked down at his cock and saw what he could of me inserting my cum covered cock into his tight hole. As I pushed it in, his cock came back to life and sprang up the further my cock went into him. He didn't even moan in pain, just gave a pleasurable sound as my dick was now all the way inside of him. I wasted no time and just began fucking him. I grabbed his cock and my fucking matched the rhythm of me stroking his dick.

"Fuck yeah," I said. "Fuck yeah, baby! Fuck yeah! Fuck yeah!"

His hole, now dripping in his own cum, was making a sloshing noise with every fuck stroke of mine. It made me start to send me over the edge and without notice, I came hard into my boyfriend's ass.

"Uhhhhhhhhhhhhhhh!!! Ahhhhhhhhh!!! Uhhhhhhhhhhhhh!!!" I yelled. My yelps became whimpers as my cock shots jet streams of cum into my boyfriend and giving me the most incredible orgasms I have ever felt. During that time, Mikey came again as I fell onto him, I felt a wetness of cum on his body. I laid on him exhausted from my mind blowing orgasm, smearing the cum between our bodies. My cock still semi-hard in his ass stayed in there. We tried to kiss but we were numb from shooting our loads so hard. We fell asleep like that. It was the best sex followed with the best sleep I had ever had in my life.