Joining a Fraternity

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It all started at the beginning of my junior year in college at the University of Colorado. I spent my freshman and sophomore years at Smith College, a fine women-only institution, but I realized early in my freshman year that I was more of a Steve than a Stephanie. As a sophomore, I realized that I didn't want my resume to forever brand me as a transsexual (after all, it's hard to go stealth when you're a guy with a degree from a school that only admits women), so I decided it was time to finish my degree elsewhere.

By the time I transferred, I sported a 2.5 inch "cock" (testosterone was very kind to my clit) and a full beard... I had put on about 20 lbs. of muscle and had developed a six pack and nice treasure trail. Perhaps needless to say, I was passing 100% of the time and loving it. Though I hadn't been especially popular with the ladies at Smith, all of whom obviously knew my history, Colorado was a different story: I was lucky enough to immediately find a hot, smart girlfriend (Karen) who was cool enough with the trans thing, as long as I didn't go public about it. Though she's straight, she loves sucking my still-growing cock... and because she's straight, she also doesn't want anyone to find out about my former identity, which is just the way I like it. One of the problems I had dating lesbians was that they wanted everyone to know what was in my pants, which is BS.

Anyway, that's how I ended up pledging to a fraternity towards the beginning of my junior year and moving into the frat house. I figured what better way to learn how to really be a guy's guy than to join a frat. All of the other new pledges were freshman and, because rooms were assigned based on seniority in the frat, I wasn't lucky enough to score a single... instead, I ended up rooming with Josh, a nice kid from Ohio who rowed crew and was about as un-"bro"-ey as you can imagine. He was actually kind of cute and I enjoyed watching him put on his jockstrap in the wee hours of the morning as he got ready for rowing practice and I pretended to sleep. His cock seemed to be average in size, but with a large head and a nice foreskin, and his balls filled out the jock nicely and created quite a bulge. He would occasionally give his cock a quick jerk or two as he put his jock on - playing with himself more than really jerking off - but I appreciated the opportunity it gave me to view his fat cockhead from up close... and because I was on the bottom bunk and he thought I was asleep, it really was from up close sometimes. He would put his jock on with his cock only a couple feet from my face on some mornings.

Speaking of cock, though I only wanted to date girls, testosterone did something weird to my sex drive. Before going on T, I had never wanted anything in my pussy... in fact, I tried to pretend that it didn't exist. After a while on T though, all I could think about was taking a hard, fat cock in my pussy... I wanted to feel a cock stretch me open and leave my hole full of cum. The problem with this, of course, is that I had a girlfriend who would definitely not be cool with me having sex with anyone else, especially another guy, and who would have a hard time understanding that I could be a man, but still want to get my pussy, which she tried to pretend I didn't have, filled with cock every so often. It didn't feel like a gender thing or sexual orientation thing as much as an instinctual thing... my pussy was full of nerve endings and it just seemed like a cock was the right tool—the natural tool, even—to stimulate all of them...basically, it felt like being stretched by a cock and filled with sperm was my pussy's birthright that I was unfairly preventing it from exercising. And I knew I wasn't gay: I didn't want to date guys and honestly didn't usually find them all that attractive, I just wanted to drain their balls into my hole.

But back to the events at hand...

After having my own room the previous year at Smith, it was weird sharing a room again. I had gotten used to being able to jerk off whenever I was horny, which was all the time. Now I had to do it either when I knew Josh was going to be out of the room (thank God for early morning crew practice!) or under the covers when I thought he was asleep at night. Because crew practice happened so early in the morning, he went to sleep much earlier than is normal for a college student, especially a frat brother. One evening, a few months into the school year, I thought Josh, who had the top bunk, was asleep, so I decided to discretely jerk off under the covers, but I was having a hard time being discrete, I guess. I had retrieved my dildo, which I kept hidden in my bunk with me, and was plunging it in and out of my drenched snatch with one hand while jerking my cock with my other hand. I was pretty into it and I guess my hip-jerking was shaking the bed and woke Josh.

"Are you jerking off down there?" he whispered.

"Yeah... does that bother you?" I groaned in reply. Somehow, it made me even hornier to know that Josh knew I was masturbating, even if he didn't know exactly how I was doing it.

Josh didn't answer immediately, but I felt movement in the bed and then heard what could only be the sound of him beating his meat in the bunk above me. At some point, we got into the same rhythm and he was jerking his cock at the same pace I was pushing the dildo into my pussy. When I heard him softly moan, I knew he was shooting his load, and the mental image of his thick cum squirting out of the slit in his swollen cockhead made me cum also. I pressed my dildo as far into me as it could possibly go and held it hard against my cervix squeezing it tightly with my cunt muscles and imagining that it was a real cock shooting a load of semen into me.

It was a little awkward right after we both came. I guess neither of us really wanted to acknowledge what had happened. Almost a week went by with no mention of our joint jerking, then one night, as I was lying in bed trying to decide whether I should attempt to jerk off again, I heard Josh say something quietly.

"Are you still awake?" he asked.

"Yeah," I quietly responded.

"I'm super horny again, man... would you mind if I jerk off again? I thought college was going to be all about getting girls, but it's just like high school. My life revolves around rowing and I haven't even met any girls. Three months at college and I'm still a virgin."

This time, I didn't respond. I just began to jerk off and I noticed by the shaking of the bed that he quickly joined me. As we jerked off together, each in our own bed and unseen by the other, I began to hatch a plan. My virgin pussy wanted to experience a real fucking for the first time; his cock wanted to experience a pussy for the first time... what I needed to figure out a way to make this happen without him figuring out that I'm a transsexual and things getting weird between us. By the time we came, I had an idea.

"Josh, I think I might know a girl who can help you out with your problem."

"What do you mean?" he replied.

"Let me check in with her tomorrow and I'll get back to you," I said, realizing that I had to think this through a little more and figure out some details.

The next evening, as we were laying in bed again, Josh asked me what I meant the night before about knowing a girl who might be able to help him.

"I have a friend in one of my classes who has been talking to me about wanting to lose her virginity. She doesn't want to wait until she's in a serious relationship because she thinks her being a virgin makes things weird... the guys she dates are always freaked out about her being a virgin. They of course want to have sex with her, but don't want the responsibility of being the one to pop her cherry. So she's been trying to figure out a way to do it anonymously. I talked to her about you, and if you're willing to do a couple things, she'd be willing to have sex with you."

"What kind of things?"

I had already thought about this, so I said: "She wants the room dark and she wants you to wear a blindfold. She wants you to keep your hands completely off of her... and she doesn't want to exchange any conversation or anything that would reveal her identity. Basically, she wants to find you laying there in the dark and she'll ride you until you both cum. She said you don't have to worry about getting her pregnant... she's protected." The last part wasn't entirely true: I was taking a full dose of testosterone every two weeks, but I was not technically using any other form of protection.

Like the rest of my plan, this method of "protection" wasn't foolproof, but would probably work... and I was so horny and wanted so badly to finally feel my pussy stretched by a cock that those odds were good enough for me. I could have made it one of the conditions that he wear a condom, but I really didn't want to. I wanted to feel his cock rubbing against the slick walls of my pussy skin-on-skin... and I wanted to experience having my pussy full of semen and having sperm swimming around in my hole. I knew that taking loads in my hole without any protection other than T was a little risky, but this whole plan was a little risky... and I was a 20-year old frat boy full of testosterone and horny as hell, so who cared about a little risk?

Josh barely paused long enough to think about it before he said "that sounds good... when can she come over?"

"I'll shoot her a text to ask her," I said... and I grabbed my phone, pretending to send a text. I waited a minute and then said "she wants to know whether tomorrow night works for you."

"Sure," he said, and when I confirmed that "she" would come over at 9pm the following evening, our plans were set.

The next day passed super slowly. As my Exercise Physiology instructor talked about squats, I couldn't help but think about squatting over Josh's prone body and sinking my dripping sheath over his pre-cum glazed cock. In Advanced Human Biology, all I could think about, of course, was sperm swimming around in vaginas—particularly Josh's sperm swimming around in my vagina—and whether my ovaries could still possibly be releasing eggs after two years of testosterone. I decided such an occurrence was very unlikely.

Finally, it was almost 9pm and Josh was getting ready for the big event.

"Where should I lay?" he asked.

I hadn't thought about that. There wasn't enough room for "the girl" to ride him on either of the bunks and there wasn't really enough space in our tiny room to unbunk the beds. Besides, in order for my plan to work, Josh had to be ready by 9pm, so we wouldn't have had time. We ended up deciding to toss his mattress on the ground. At five minutes before 9, I tied a bandana tightly around his eyes and instructed him, wearing only his boxers, to lay down on the mattress...he was so excited that when he laid down, his boxers were tightly tented by his hard cock. Seeing the outline of his excited member made my pussy drip even more in my boxers. I told him he should take his boxers off when I turned the lights off and that I would let the girl in and then wait outside in the common area for Josh to come get me after the girl leaves and he's had time to clean himself up.

I turned the lights off, stepped outside our room, and waited a few minutes. Then I walked back in. "She wants you to remember not to touch her at all and that she won't say anything, even if you talk to her... I'm going to bring her in now. Are you ready?" I said to Josh. When he said yes, I opened the door just a crack—though Josh didn't know that—and whispered to the non-existent girl, loudly enough that I knew Josh could hear, "he's ready for you...I'll be outside here watching TV. Have fun." Then I walked toward the door and pretended to leave, but obviously stayed on the inside of the door as I closed it.

As my eyes adjusted to the dark, I stripped off my t-shirt, boxers, and jeans. My pussy was dripping everywhere and I felt so utterly sexy and powerful. I left my clothing in a pile near the door and walked, completely naked, over to where Josh was laying on the ground. I reached out and stroked his cock for a few seconds and then squatted over him and ran the head of his cock against my hard, engorged clit several times before placing it at my opening and dropping my hips down so that it pushed tightly against my ready hole. As I lowered myself onto his cock, he gripped the sides of the mattress tightly and thrust up his hips to meet me. I had to stop myself from groaning as his head quickly penetrated my sheath...it felt amazing finally having a hard, hot penis rooting deeply in my vagina.

Finally, my pussy lips met his groin as he bottomed out in me. I could feel his huge cockhead, which felt like it was swelling even larger inside of me, already throbbing against my ripe cervix. I was only able to raise and lower my hips a few times, enjoying the feeling of his manhood rubbing skin-on-skin against the clenching walls of my pussy, when he groaned "I can't help it... I'm cumming." I suddenly felt a strong pulsing inside of me and a warm sensation. When I ground down against him, rubbing my little cock against his pubic bone and grinding my cervix against his swollen, throbbing head, I felt an extra slickness inside me. Imagining all his sperm swimming inside me got me so close to cumming, but didn't put me over the edge just yet... I'd been waiting for this for years and we'd only been fucking for a minute. I didn't know if or when I'd get another opportunity to do this, so I wanted—needed—to make this time last.

I began riding him again, trying to take advantage of his hardness before he lost his erection, but to my delight, his erection didn't seem to be deflating. I worked my cunt up and down on him, enjoying the way his raw cock stretched my pussy and pressed against the wet walls of my unprotected hole. When he began to buck into me, I started to think about how his cock was forcing his earlier load—millions of his sperm—deeper inside my snatch and possibly helping them find the opening in my cervix leading to my unshielded womb. That thought was too much for me and I had to work hard to hold in my moans as I came, my pussy clamping down around him. I reached back and fondled his big balls in his sack... that, combined with my sheath tightening around him, was too much and he bucked up into me, emptying his balls deep in my pussy once more.

As I stood up, his deflating cock, coated in our combined cum, slipped out of me and I had to grab my pussy, which was oozing his thick loads, to stop it from dripping everywhere. With my hand between my legs cupping my pussy, I waddled over to the door and tried to put my clothing on. I finally gave up on keeping all his semen inside me and just put my clothing on...his cum was already all over the crotch of my boxers and my inner thighs by the time I closed the door and I could feel it continually dripping out of me as I sat in the TV waiting for him to clean himself up and come get me. I hadn't thought about this part of the experience and realized that if I could figure out a way to keep this going, I was going to have this problem often and that it might be time to start wearing briefs. I thought about going to the bathroom to clean myself up, but realized that doing so would probably be futile. Besides, I wanted to be in the TV room to see his face when he came out to get me.

A few minutes later he walked out of the room in only his boxers and t-shirt with a shit-eating grin on his face.

As we walked back into the room, I noticed that Josh had already tossed his mattress back in the top bunk. He wasted no time in getting into bed. I turned the light off and stripped down to my cum-coated boxer shorts and then laid down in my bunk.

"So?" I said. I could almost hear his grin in his voice as he responded.

"I don't know where you found this girl," he said, "but she was amazing... we did it twice."

As he recounted the highlights of our adventure from his perspective, I reached down and fingered my hole, feeling his thick semen running out of it. Suddenly realizing that I hadn't yet tasted or smelled his cum, I worked two fingers into myself and got them coated with his cum. I then ran them under my nose and sucked on them. I loved the slight bleachy smell and the taste of it was indescribable, but such a huge turn-on. Part of me still couldn't believe that only minutes before, the fluid that I was now tasting and that was coating the walls of my vagina had been deep inside his balls and had been squirted into my pussy by his ejaculating cock. Thinking about it got my engine revved again and I began to play with myself, eventually saying "man you gotta stop talking about it...now I need to jerk off."

"I might join you," he said, adding,"I can't stop thinking about the feel of her pussy."

As we both jerked off in our own beds, I thought about his cock in my hole as I used my dildo to push his cum even deeper inside of me. We came at almost the same time, said goodnight to each other, and finally went to sleep.

To be continued...(if there is sufficient interest)