ButtSluts (cd, m/m, m+/m, oral, anal)
My name is Jimmy James. When I started high school, my parents shipped me out to boarding school to teach me discipline. They were mad because I had always been a disappointment to them. I wasn't terribly manly and I liked to dress in girls clothes. The more often they caught me dressed like a girl, the madder they got.
The final straw was when they found me in the pool house wearing my sluttiest outfit. It wasn't so much what I was wearing that bothered them tho. What bothered them was that I was on my back with my legs spread. While my friend Bob was laying on top of me, fucking the ever loving shit out of me. It was quite a shock for all of us.
So off I went.
The place sounded horrible. It stressed regimented schedules and family. The housing was set up to be two person cabins to promote self reliance, blah blah blah. It wasn't so bad as I thought tho. I ended up being quartered with the perfect room mate. His name was Mike, but everybody called him Mickey.
I found out he was the perfect room mate about six weeks into the first semester. I was s'posed to go home for the weekend, but missed my train. When I got back to the cabin, there was Mickey wearing the sluttiest little school girl outfit I had ever seen. Black high heels, thigh high white stockings, tiny white thong, ultra short plaid skirt, thick black belt, see thru white top, stick on D-cup breast forms, no bra and long black wig....
He was fucking HOT!!
I could only hope that I looked that good when I dressed up. Everybody always teased him about having a big ass, but dressed like this, IT WAS PERFECT!!! The whole thing just screamed 'slutty little sex kitten'. I was sure he liked getting fucked as much as I did.
As I stared at him, I could feel my cock getting hard. That's when it dawned on me that I should have a little fun. We were both still staring at each other in shock. He quickly began to scramble to cover himself.
"Mickey?" I said disdainfully as I blocked his escape to his bedroom.
"Oh" he chirped as he tried to hide his face.
"Well aren't you pretty! I've heard about guys like you. Average guy by day, Buttslut by night." I said as I started to push him around.
"No, it's not like that! Please don't tell anybody!" he pleaded.
He was so pretty as he stood in front of me begging me not to tell anybody. I wanted to fuck him so bad, I could feel my cock throbbing. I had to wonder if my friend Bob thought the same thing when I dressed up for him. He must have, because he was constantly begging me to get dressed up so he could fuck me.
"Tell them what?! You're a buttslut! When the sun goes down, you change into a girl and go cruising for cock?!?" I said pushing him some more.
"No, I, No" he stammered.
"Really?!? Late for class at the girls school, were you!?!" I boomed while grabbing his skirt.
He stepped back with no reply. He looked so sexy as he stood there pouting.
"Or maybe you were going to do some cleaning and you put this on so your clothes didn't get dirty!" I mocked.
I slammed him face first over the back of the couch. I grabbed his hips and stood between his spread legs while he kicked, squealed and tried to get up. When I looked down, I couldn't believe how sexy he looked. His arms and legs were waving around. His skirt was pulled up. Leaving his ass wide open, with nothing but a thong strung thru the crack.
God, he was sexy!!
I quickly pulled out my hard cock and started poking it at his ass while he struggled.
"No! God No! Please Don't!" he squealed
"Fuck you! If you wanna dress like a whore, you better be ready to fuck like a whore!" I yelled as I stripped his panties to his knees.
I could see his cock was rock hard and knew he wanted it as much as I did.... He continued to struggle as I positioned my cock. When I eased my cock into him, he surrendered and relaxed. I giggled when I found his ass already lubricated and ready to go. I grabbed his hips with both hands and began to fuck him hard and fast.
"Yeah, That's it. Shut up and take it.... Buttslut!" I said patting his ass.
He just laid there and moaned. He looked and felt so good, I began fucking him harder than ever. It was so cool to know I was fucking a guy who was as big a buttslut as I was. I began to think of all the times Bob had fucked me. He got to see me like this all the time. I used to carry around girls clothes just in case he wanted to knock off a quickie.
We were only fourteen, but I had been dressing up and sucking his cock since we were nine. When we were eleven, he started fucking me. He had fucked me every way and every where that we could find. He had man handled me and fucked me just like this a million times.
I was brought back to reality when Mickey started driving his ass back to meet my thrusts. I heard him moan and felt him begin to quiver as I drove my cock in as hard as I could. I got a big smile, because I knew exactly what it meant.
"What's the matter buttslut? Too much for you? Can't take it? Had enough? What's the story?" I growled.
I heard him squeak and felt his asshole squeeze tight. I continued fucking him as hard as I could and started to laugh.
"What's that buttslut? You like it and you want me to fuck you harder?" I chuckled.
Just then, he exploded into orgasm. He started to squeal and jerk. His hips started to buck wildly. His asshole started to spasm around my cock. I was laughing, fucking him hard and slapping his ass.
"Yee Haa! Ride 'em cowboy! That's my girl! Let's go!!" I teased.
He continued to flail around and I didn't let up a bit. I was fucking him for all he was worth. It was an amazing feeling. It was no wonder Bob liked fucking me so much.
Just as he began to relax, I felt my own orgasm begin. I drove as deep as I could get and emptied my balls inside him. I groaned and panted to catch my breath. Once I caught my breath, I pulled my cock out, smiled and put it away. Then I slapped him on the ass.
"You're a good fuck. Now go get me a soda" I told him.
I looked down and smiled when I saw his cum stuck to the back of the couch and my cum drooling out of his gaping ass. Then I sat on the couch and watched as he pulled his cock back, pulled up his panties, then obediently walk off to get my soda.
"He's got such a hot ass! I wish I had an ass like that!!" I thought to myself as I watched him go.
When he got back, I had him sit next to me. The first thing I did was grab his tit. He pulled away and looked down. I laughed, grabbed both his tits, then lifted his skirt and looked at his panties just to add to the humiliation.
"You're a hot little piece of ass Mickey! Or should I call you Shelly?" I chuckled.
I watched him blush and crack a small smile.
"Please don't tell anybody. Call me whatever you want, but please don't tell anybody." he begged
"I tell you what I'm gonna do for you Shelly. I won't tell anybody. BUT! You gotta do something for me." I said seriously.
I watched as he looked up at me and tried not to smile.
"Next time we do this, I get to be the buttslut." I said with a big smile....
I watched as his expression went from expectation to total shock. His jaw hit the ground instantly. He was staring at me totally dumbfounded.
"What???" he said shaking his head in disbelief.
"You heard me! Next time I get to be the buttslut!" I giggled.
We both squealed with delight and gave each other big hugs. We started telling each other everything after that. I went and put on a slinky black dress and we sat around all night talking about the things we did, what we liked, the clothes we had. It was like we had been girlfriends forever.
Turns out we had pretty similar stories. We both had strict parents. A dominant male side and a super submissive female side. We both started quite young. Both of us were turned on by girls, but thought it was more fun to be fucked like a girl. And we both loved to swallow cum. All in all, we were two peas in a pod.
For the next two years, we were both insatiable lovers. We would roll dice or flip coins to see who got to be buttslut. Whoever won, would put on the sluttiest outfit he had and be biggest slut he could be. It was fucking great.
Quite often, we would muse about how to get other boys involved so we could be buttsluts together. How we could get a bunch of guys to fuck us both all the time. We talked about having sex parties and pulling dual trains for gang bangs.
The one I thought was most interesting, was to set up our cabin as a brothel for some of the upperclassmen. We could both get dressed up and offer ourselves up for some ridiculously low price. Something that would make sure they could afford to stop by often. Like $5 for a BJ and $10 for a fuck. Just the thought of guys paying money to give us what we wanted was a turn on.
Bob managed to stop by 5 or 6 times, and that only added fuel to the fire. We spent the whole time dressed in our sluttiest outfits and begging him to fuck us. He did too. He rocked our world and fucked us both silly every time. He was awesome!
Now Shelly and I run a small escort service from our cabin. We dress up and entertain at parties for some of the boys at school. They pay us up front and we provide any sexual service the guests might want. Turns out, I've got the perfect room mate and we both love the school.