The Exploits of Cockslut Kelly 01

Hello my fellow perverts and welcome to my very first story on Literotica (but certainly not my last. My little perverted mind has so many lovely stories and fantasies to share with you). I love this site because we can share our deepest, darkest and most depraved fantasies (and past experiences) with other likeminded individuals. My stories will most likely be from my point of view and I am a sissy, submissive little slut so all you bottoms out there can easily put yourself in my place and pretend you are the one on the receiving end. That's what I do when I read. Of course, if you are a top and love using a little sissy, then you should definitely get a thrill out of these stories as you see what I am willing to let a man with a big dick do to me. :)

I welcome all feedback, but if you are going to critique (which I am certainly ok with) do it constructively please. My fantasies may not be in line with yours, but then again some of yours may not be in line with mine. That is no reason to bash someone. This site is about the free expression of desires and if you don't like mine, move on to one of the many thousand other stories on the site and don't dwell on mine.

Play nice.

Unless your cock is in my mouth or ass, then play rough and dirty!!!

Oh, and about me. You can read my profile, but let me just sum it up here. I'm 19 and I turn 20 in January. I'm a white guy who is a small, petite ball of fun (so I've been told) as I am only 5'4" and when I'm wet or full of cum, I might tip the scales at 120 – 121 lbs. I have very little hair on my body and what I do amounts to maybe some peach fuzz. I may be small, but my body is quite firm and I have an ass that even I'd love to fuck. Much more girlish than boyish. I have a 6 inch circumcised penis, give or take, but it seems bigger on me because of my frame. I have dirty blonde hair which comes down to my shoulders. I like having the longer hair because I can pull it up into ponytails or pigtails which really look good when I cross-dress, you know, nothing too outlandish, but panties, nighties, costumes, whatever the men want. I have blue eyes and my lips are pretty full. They are soft and more than one man (and girl) has told me how much they like kissing and nibbling on them.

Oh, and I love letting men use me to fulfill their fantasies when other people are too prude to do it. I'll tell you a secret. I even like being peed on. I know, not everyone's cup of tea, but if you are truly a submissive, there is nothing more submissive then having your man unload his bladder on you. Don't worry though, since I know that is pretty extreme to some people, I will always give a warning in case that particular story includes any of me being a urinal. This story is officially certified "pissing on Kelly" free. :)

Now, let's get started, but before we do, everybody butt dance...

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Being away from home for the first time at 18 can be a frightening experience, but doing so by heading off to college has a way to counterbalance that fear with excitement. For the next four years I could do what I wanted and explore who I was without the immediate fear of being discovered by those close to me. You see, I'm a bi guy with the needle edging farther and farther towards the gay side, but my actions have been known by few and my desires have been only secretly scratched. I'm sure a lot of people have suspected me as gay, what with my small frame and somewhat girlish mannerisms, but I still tried to put the straight facade on, mainly for my straight-laced Christian parents.

That is, however, not to say I haven't already explored my gay side. I was introduced to gay sex, ironically, by two very close female friends. They were two cute girls who knew me rather well and helped me open up about my feelings and even introduced me to what would become my new obsession: cocks. It is a story for another time, but the quick summation is that these two used some strap-ons and showed me how to suck dick and they even took my anal virginity. Sigh. That was a fun weekend.

But our story picks up almost a year ago after I had left for college. I was still 18 and as soon as I got to college and met my roommate (another freshman who was nice enough to be around even if he was not much to look at. He was more of your typical socially awkward nerdy kind of guy), I immediately searched out the local adult bookstores. My hometown had none but I had read about them on sites just like this so I was dying to try them out. I frequented quite a few and it was a great way for me to explore. I took cocks through glory holes, gave up my boy pussy to several strangers bent over a couch in a viewing room or down on my hands and knees on a dirty floor and I even visited a theater a few times.

They were fun times for sure, but it was hard to really get into the submissive role for an extended period of time because most were there for a quick nut. Don't get me wrong, I loved it, but I wanted something more involved where I was completely used over and over.

I had set up a profile on another site (no, I'm not going to give them free advertising here) and flirted with a lot of men who told me their fantasies of what they would do with a hot, young thing like me. I decided to post on their forums that I was looking for a man who would like to have me for the weekend to do whatever they wanted to me. I said that I was willing to try anything that did not include any lasting damage from pain or abuse nor would I be ok with anything involving scat. My request was that they email me with pictures of themselves, their cock (an absolute must) and a description of how they wanted to use me. I posted about ten pictures of me of so that they could see what they would get to play with:

- One of me in jeans and a tight t-shirt

- One of a close up of my face where I am smiling

- One of me in little panties

- One of me standing up naked with a hard erection

- One of me on my knees, naked with my hands behind my back and my mouth open

- One of me face down, ass up on my dorm bed

- One of me holding a big fake cock in front of my face

- One of me with the big fake cock buried to the hilt in my mouth (I wanted to show off what I could do)

- One of a close up of my tight, hairless little pucker

- One of a close up of my hard, six inch cock

As you can imagine, I got A LOT of responses to my posting with many guys talking about how they wanted to fuck me or have me give them blowjobs. I got a lot of dick pictures which quickly got saved to my hard drive, but none of them seemed to be much more than just them wanting to stick their dicks in me for a quick nut. That is what I was getting from the bookstores.

I wanted more.

I did reply back to many of them that I liked but I didn't plan for the weekend.

I wanted more.

I told them that I would love to let them do what they wanted to me and even quickly took time away from my computer to go across town to meet a guy at his house where I came in, dropped to my knees in the front door and let him plow my face till he came down my throat, but this was still not the plan that I had for the upcoming weekend.

I wanted more.

When I got back to my dorm room, my roommate was there. We exchanged our normal small talk although as he is a little nerdier than I usually associate with, we really didn't have much to talk about. I quickly grabbed my laptop and moved to my bed to see if I had any more responses. Normally I sit at my desk, but with him in the room, I didn't want to take the chance that he would see what I was looking at or reading. It is one thing to be bi or gay (which he knows about and seems somewhat ok with), but it is a completely different thing to flaunt that in front of someone. I am fully aware that gay sex can make straight people a little uneasy. I do try and be respectful of that.

I fired open my email and there were three more responses since I last looked prior to my cross-town cock trek. One came from a really fat, hairy man with an almost imperceptible penis who mentioned something about wanting to sit on my face (my normally absent gag-reflex suddenly decided to stop by for a visit after reading that), another from a young man like me that wanted to know if I wanted a partner in being used (uh, no, why would I want to share???) and the third one was the payday. It was a man who looked to be in maybe his mid-40's and in really good shape. He was naked with little body hair, an athletic physique of a man who was no stranger to exercise or sports and he was sporting a large piece of meat dangling semi-engorged between his legs. He was an attractive man, a manly man and I could easily see myself submitting fully to him.

I couldn't believe how hot this man was. I knew right now I would do whatever he wanted me to do. Oh yeah, I had not even read what he wanted to do to me. I read down over his email and without giving the rest of the story away, I will say that he hit all the right buttons on what I was looking for. Humiliation, degradation, submission, group play, cross dressing, bondage and much more. I was slowly clenching my ass together and relaxing it and as I read the description, my pelvis was slowly thrusting with each clench. I was desperate to touch myself and get a release but there was no way I was going to be able to with Ryan still in the room.

I closed my laptop and told Ryan I was going to head to take a shower before bed and he laughed. "Man, I was just about to do that too. We can go together," he said.

"Fuck," I thought. The showers are semi private, but not fully private and I was really hoping to maybe be alone so that I could jerk off. Granted there was no guarantee that the showers would be completely empty, however now that he wanted to hit the showers too meant that I was guaranteed to NOT be alone. Worse is, I couldn't think of a reason to now suddenly back out so we both grabbed our stuff and walked to the shower area.

When we got to the showers I noticed that the place was completely empty. Just my luck. If Ryan had not come here too, I would have easily been able to provide myself a much needed release after sucking a cock across town and then reading about how this man planned to use me over the weekend. Ryan went to take a piss so I quickly picked one of the showers, turned on the water and placed my supplies inside the stall. I started to peel off my clothes with hope that I could be done before he got back because I was still rock-fucking-hard but as soon as I dropped my pants and underwear, Ryan turned the corner to find his own stall and saw me standing there in all my naked, erect glory. I turned beet red and quickly covered myself.

"Oh, uh, I'm sorry," he said. I was so embarrassed that my roommate had just seen me hard, but due to my love of humiliation, this only added to the fire burning inside me. "Hey, it's uh, it's ok. I get them too," he said in an attempt to make me feel better I guess. I quickly stepped inside my stall and pulled the tattered shower curtain closed and let the water cascade over my body.

I heard him shuffle down the hall and pick the shower directly across from me. I heard him turn on the water and then the air was filled with the normal sounds of someone preparing for a shower. Curtains moving, shower stuff being placed down, clothes being removed, etc. I heard him enter the shower and pull his curtain closed.

"Hey Kelly," he said after a few minutes of silence.

"Uh, yeah," I replied.

"If you need to jerk off, I am, uh, I'm ok with it. I have to do that a lot too," he said.

I had no idea what to say. How do you respond to that?

"Uh, thanks," I said.

"Hey Kelly," he said again after a few moments passed again. "Can I ask you a question? It may be a little weird, but I don't really know who else to ask."

He was a really nice guy but a little bit on the social awkward side so I had no idea what he would want to ask me after suggesting that it was ok for me to jerk off in the shower across from him.

"Ok, uh, sure," I said apprehensively.

"Ok, and this isn't the question that I want to ask, but, uh, since you, said you are, uh, gay, would you say that you have been with a lot of guys, you know, seen them naked and all?" he said, his voice shakey and unsure in his resolve to get this question out.

"Whoa, that's a bit personal, don't you think?" I said, completely taken back.

"I'm sorry, nevermind," he said, his voice trailing off. "Just forget I said anything."

I felt bad for the guy. There was something that was obviously hanging very heavy on his mind.

"No, it's ok. Yeah, I've been with quite a few guys, why do you ask," I said.

"It's ok, nevermind," he said.

"Jeez," I thought to myself, he had now moved on to full on pity mode. "Ryan, it is ok, what did you want to know?" I said.

"I just, I don't know, I was just curious to know how I compare to other guys out there, you know in real life," he said.

Ok, now this was actually starting to get a little intriguing. "Compare how?" I asked.

"You know, in size, down there," he said meekly.

He was so inexperienced. It was actually kind of cute. "You want to know how your dick compares to other guys?" I said.

"Yeah, uh, if you don't mind. If you don't want to look at it, that's ok," he said.

This was a tricky situation for me. At the time, I was at the impression that he probably had a small penis and I would then have to be very careful as to not make him feel bad, but at the same time, he seemed like the kind of guy that has been rejected for most of his life so I didn't want to just say no.

"Sure, I'll give it a look and let you know. When did you want me to do that?" I asked.

"Really? Thank you. Uh, we can do it right now if you want. There's no one else in here and we are already naked," he said.

"No time like the present," I said. "Do you just want me to come over there?"

"Sure, but I'm not hard like you were, is that ok," he asked.

"Yeah, that's fine," I said and pulled my curtain back, stepped out and pulled my curtain closed. I walked across the small walkway to his shower and pulled his curtain back. Ryan was a lanky young man, taller than me by a few inches with pale skin and a little patch of dark hair on his undefined chest. He looked like a kid who spent a lot of time doing activities in make-believe worlds like online gaming and science fiction. He had turned a little so that his dick was away from me when I pulled the shower open and he looked at me with a little bit of apprehension in his eyes. He unceremoniously gave me a once over, my head and body dripping with water, my shoulder length blonde hair wet and framing my face. I know I have a very feminine look and I am sure the wetness added to that. Well, except for the rock hard cock jutting out from my body that is.

I pulled the shower curtain closed, encasing us both together in the small steam filled room. I looked at him and I could tell he was very nervous. "Relax," I said, "it's ok. I don't bite." I smiled, trying my best to make him feel at ease.

"It is just weird," he said, "I've never been naked in front of anyone."

"Really? No one?" I asked.

"No," he said and I could see the shame start to cross his face. I felt bad so I tried to make him feel better.

"Then I feel honored to be the first," I said and smiled again. "So, let's see what you are packing."

He hesitated at first and then turned towards me. I looked down and my jaw dropped. Ryan was packing a missile. His cock was flaccid, but still hung down a good seven inches. He had a great thickness, a beautifully formed mushroom head and slight veins causing protrusions from the shaft. It was nestled in a wiry patch of dark pubic hair (this would have to change) and accented by two large balls. This cock did not belong on this kid but here it was. I couldn't stop staring. I all of a sudden wanted my nerdy roommates cock and I wanted it bad.

I am not sure how long we stood there, but I know that I never stopped looking at it. It wasn't the biggest cock I had ever seen, but it was definitely a large, impressive member and my shock truly came from the fact that I never would have suspected him to have something like this.

"Is it, uh, you know, uh, nice?" he said, my silence unintentionally messing with him.

"Ryan," I squeaked out, my voice hard to find, "you're cock is amazing. It really is very nice. I think it would easier to tell just how nice it is if you were hard, but that has to be one of the most impressive soft cocks I have ever seen."

"Really?" he asked, an appreciative smile starting to form on his face.

"Oh yeah, but for me to give you a proper review, I need to see it hard and I need to see it without all of that hair," I said, never taking my eyes off his impressive meat. I know I was possibly pushing it because this could easily weird him out, but it was worth it in case he went for it.

"Uh, ok, but how should I get it hard? And I've never shaved myself so I don't know how to do that," he said.

"Well, uh, I could shave you if you want, I mean, if that doesn't freak you out and then we can worry about the getting you hard part," I said hoping he would say yes. I knew very well that if he let me get down on my knees and shave his balls and cock that my hands and the shaving cream would be enough to make this monster rise. Please say yes, please say yes, please say yes.

He kind of shrugged his shoulders and then said, "Ok, that's fine."

I heard the Hallelujah Chorus ring out in my mind.

I looked around and saw his can of shaving cream and his Mach 5 razor so I grabbed them and before I knelt down in front of him, I looked at him and said, "You do realize that I will have to touch you to do this, right?"

"Yes, that's ok. I've never had anyone touch me before but I've always wanted someone too," he said.

I just smiled and then sank to my knees in front of my nerdy roommate with the big cock. This was going to be hard because all I want to do is have him shove that cock deep into my throat.

I reached out and grabbed Ryan's impressive dick and heard him moan a little. I looked up at him and said, "Are you ok?" I knew he was, but I still wanted to be comforting to him. I had made up my mind at that point that I was going to meld him into a very confident top. I was going to teach him how to treat someone on their knees, but it was going to be very skillfully played out. Since I was the first to touch his cock (and the first one to suck his cock, oh yeah, it will be mine), I was going to have him do to me what I like which would in turn teach him how to be dominate.

"Yeah. It feels better than I thought to have someone touch me," he said. I smiled at him and then lightly stroked his cock a bit more. His eyes fluttered a bit and I knew he was mine. I was going to taste my roommates cum.

I removed my hands and picked up the bottle of shaving cream and sprayed some in my hand. I then worked it into both of my hands and moved them to his cock. I ran my cream covered hands all over his balls and dick and immediately found it rising in my hands. This was good because a hard cock is always easier to shave than a soft one, even if the soft one is as full and rigid as his was. I continued for a bit till his cock raised completely to its full size, a good 8.5 to 9 inches of rock hard man meat.

"Haha, looks like we got the 'getting you hard' part out of the way BEFORE we shave you," I said. He just muttered back as small moans of pleasure seeped from his mouth.

I rinsed off one of my hands and picked up the razor and went to town on him. I carefully removed all of the hair from his balls, underneath his balls, his shaft and even the area above his cock. I stroked him quite a bit during the procedure and ran my fingers over and under his balls as my fingers continually searched for areas that needed more razor attention. His massive dick felt so good in my hands and I heard him moan plenty of times during the process.