This is going to be a little long, but it's important to understand how this happened.
During my junior year in college one of my friends and suitemates, Matt, went in drag to one of the big Halloween parties. He had a very slight build, and delicate features. The women pretty much all thought he was very cute. He'd had a couple of our female friends make him up, and the general opinion among our eight man roomgroup, was that he looked alarmingly good as a girl, which is an awkward thing to admit as a straight guy. He went with it, and pretended he was a woman the whole evening, with some pretty amusing but also unfortunate results.
At about 12:30 a.m, after only a couple of hours at the party, still early, me and Matt, my crossdressing roommate had gone back to our suite. He wanted to get out of his costume. I was basically along for security. His get-up had caused quite a stir. For one, no less than three guys (only one of whom we knew, it was an open party) thought he was a girl, and he ended up dancing with them. When one of them, very large, found out he was a guy after two whole slow dances, there was almost a fist fight. Three of us had to intervene to prevent Matt from getting ground into the dance floor. There were also a couple of guys who were friends of ours who were really disturbed by the whole drag thing, and him dancing with guys, and they both got a little nasty. Those of us who knew the deal were all pretty shocked by the lack of good humor all round, and Matt decided he didn't want his whole evening ruined by getting beaten to a pulp, or for people to start thinking he was gay. Or that he was making fun of gays. None of us were exactly sure what everyone was so upset about. It had just been a joke, but everyone seemed to be taking it so seriously.
Walking back to our rooms, I told him about how funny it had been that everyone thought he was woman. A few of our friends figured it out right away, but one guy came up and talked to us for awhile and then suddenly just blurted out 'You're a guy!' He'd thought he was talking to a woman. He, however, thought it was really funny that he'd been had. 'Damn, I was going to ask her out!' Matt then told me that one of the guys who'd he'd slow danced with, but not the one who wanted to beat the s-t out of him, had developed a hard-on. I asked him if he'd felt freaked out and he said, no, he'd actually started to dry-hump him on the dance floor! I was a little shocked but basically just thought it was really funny. I asked him couldn't the guy tell you were a guy, if he was rubbing up against you like that? He explained that he basically had tape over his panties (he was serious about this costume) pulling his penis and balls back between his legs. He and the girls thought he would give himself away pretty quick if a guy felt his 'package.' I still couldn't believe that a guy who was actually dancing that close with him couldn't tell he was a guy. I said something about him just dressing up, not actually going to the party to hook up and make out with some guy. He didn't say anything back, and I suddenly got the idea that I hadn't got the whole picture. I asked him whether he was trying to see what he could get guys to do, thinking he was a girl. That, he said, was basically the idea that he and the girls who'd put his costume together had: see how far he could get some guy to go.
This, I thought was classic. I assumed what he meant was that he would try to see what the guys would ask him to do, or try to get his phone number, something like that. So I asked him what had happened with the guy who'd got hard dancing with him. He told me what they'd done was gone upstairs to an empty room, and he'd given the guy a handjob! I was totally blown away. I asked him what the hell had ever given him that idea. Giving another guy a handjob itself wasn't really that big a deal to me. I'd never done it, just done it in front of other guys, but I knew friends who had when I was a kid. There were even some rumours that some of us 'in the know' had heard about more than one pair of friends of ours who, when roommates, had done a little of this, too. Guys got horny, it happens, I guess, but you just didn't talk about it. My friend explained that the guy had tried to kiss him a couple times, which he didn't want to do, and didn't think he could do without getting found out, and he thought he had to do something more, just to see if he could, but didn't want to blow his cover, and he thought that the guy would probably agree, to getting jerked off, and he could get away with it. I guess he was lucky that this wasn't the guy who figured out he wasn't a girl. I thought about asking him what it was like, but was afraid to.
When we got back to the room, and got our coats off, I looked at Matt. It really was amazing, he looked like a pretty good-looking girl. A bunch of us, back at the party watching him dancing with one of the guys who'd thought he was a woman, admitted that we'd want to sleep with him, if we didn't know he was a guy. I told him that we'd all said this, literally, saying something like 'man, you know, if we didn't know it was you, we all agreed we'd f... you.' I also thought that I would have let him give me a handjob, if I'd been that guy dancing with him, and hadn't known he wasn't a girl. But I didn't say anything about it. The fact was, even knowing he was a guy dressed up like a woman, with the padded bra, the wig, and the make-up looking at him then I started to get turned on thinking he was a girl and doing him.
We went down to our rooms to change and a couple of minutes later Matt knocked on my door and came in. He had taken off his skirt and was still in his sweater, stockings and panties with all the tape, which he explained and showed me kept his 'package' out of sight and feeling range. He asked me for a pair of scissors or a knife to get some of the tape off since the girls had apparently bound him up pretty well. I told him there was a pair in the bureau drawer and as I was getting changed, he managed to get his contraption off while I, curious, watched. He fumbled around a bit and ended up just cutting the whole thing, panties and all, off. He then turned to me and put his penis and balls between his legs, and then pressed his legs together, explaining that no one could have told he was a guy. At this point I was down to my boxers, and looking at him now, naked from the waist down and no penis visible, I was stunned and just stared. Matt was clean shaven, it was a swim team thing, and all that was there between his legs was smooth bare skin, that looked like a womans, or more accurately, a young girl's pubes.
'Jesus, you look just like a girl,' or something like that. I'm not sure exactly what I said, but Matt stood there for a few seconds, and I looked at him, and got a hard on that tented and then poked out of my boxers. Matt didn't say anything. I told him that I was convinced, he did indeed make a pretty hot looking woman. What the hell, I started to explain, guys are visually stimulated very easily, he was dressed up like a girl, that was what he was trying to do, and it worked. 'Do you want to f...?' Matt asked.
'My dick says so,' I said it without even thinking. I must have thought he was just asking whether I was turned on. I thought that was pretty obvious. I was wrong about the first part.
Matt walked over to my bed, saying 'Between my legs, okay?' I turned round and he lay on his back and worked his penis and balls back between his legs and then pressed them together. I knew what he was talking about. Some people call it the 'Princeton f-k.' I knew what it was, though we didn't know that name for it back then, because some friends had talked about doing it that way with other guys when I was younger, and we'd all, I'm sure, done it with our dates or girlfriends later. Almost like sex, without actually having intercourse.
At that point though, I'd never done it with a girl, and certainly not with a guy. I'd never done anything with another guy except jerking off once in the gym shower, or in the same room. But I was too turned on to think about it. I pushed my boxers down and sat down on the bed. I reached out and touched Matt's pubes, then rubbed his stomach, and then one of his thighs. He thrust his hips at me a little.
'Come on, somebody could come back,' he said. I got up on the bed and threw a leg over him and started to manouver on top of him, to line my dick up between his legs.
'You need some lube, first' he said. I stared down at him and then got off from above him and got some lotion from my dresser.
'Give me some,' Matt said. I handed him the bottle, and he squirted some in his hands and started to rub it on the insides of his thighs, and on his penis, which was now hard, it sprang out from between his thighs. I lubed up too, trying not to enjoy it too much, and watched him put his penis back down between his legs. I quickly got back on top of him and aimed my penis between his thighs and pushed it in the cleft. The feeling was great, warm and soft and slick, but the angle was wrong. I tried to pump in and out, but with his penis down between his legs, too, I kept hitting it and had trouble keeping my penis between his legs. Matt lay still for a couple of minutes while I tried to rub between him, then suggested it might work better if we were on our sides. I got off of him and lay on my side facing him. He rolled over and moved up the bed a few inches so we were basically face-to-face (I was few inches taller). This put my penis in direct line with the cleft between his thighs a few inches below his pubes. I pointed my penis between his legs with my hand and pushed between them. We still hadn't touched each other at this point, other than my penis going between his legs, and our legs touching. A couple of inches of me slid between his thighs. It felt very nice. I started to work in and out with short strokes.
'You need to get closer to me,' Matt said. He started to try snaking an arm under my side, and I was so turned on, I did the same. I got one arm under his hip and grabbing his ass, pulled him against me as I felt him hugging me, and my dick sliding all the way between his legs. 'Oh, Jesus,' I said. 'C'mon, do me.'
I didn't need any more encouragement. I started pumping my hips, driving my penis in and out between his legs. It was so intense, I groaned. Matt lifted his upper leg just slightly.
'Take it easy, or you'll cum right away,' he said. I slowed down a little and with his leg raised, it wasn't so tight, and I began to slowly rub my penis against him. I could feel his erection against mine as I pumped in and out. With his legs slightly parted it would move back and forth as my stroking pushed it back and forth between his own thighs. I realized it probably felt almost as good for him as it did for me. I held onto his ass and he had his arms wrapped around my back, which he started to caress. I started doing the same to him, moving my hands up under his sweater. Our faces were almost touching on the pillow. We looked at each other briefly, then, embarrassed, I closed my eyes. I screwed his thighs for a couple of minutes but then had to stop because I was getting too excited, and didn't want to cum right away. Matt was still sort of humping against me. I opened my eyes and saw he had his eyes closed, too. I lay still for a few seconds, then he opened his eyes. He squeezed his legs around me.
'You left the door open,' he said.
'What?' I started to pull away from him, but he held onto me.
'Keep going, just hurry up.' I didn't move for a few moments, but Matt started rubbing his thighs back and forth against me, and I started screwing him again. I was looking right into his face. With the makeup and the blond wig, it was like I was looking at a girl. Matt's eyes were closed, lips slightly parted. If he'd been a girl, I would have been kissing her while we had sex. I pulled him tighter against me, and he clutched me, both of us were pumping our hips against each other, and I could tell I was close to cumming. I gave Matt a quick, closed-mouth kiss. He kept his lips pressed against me and kissed me back, gently then harder. We both opened our mouths a little, but didn't french. It felt just like making love with a girl. I opened my eyes and saw Matt eyes closed as he kissed me. I felt myself going and kissed him frantically as I slammed my penis betweeen his legs, then looked down at where we were joined just as I started to cum.
'Oh, Jesus!' I pulled my face back from Matt's as I was cumming. I was all the way in betweeen his legs, stopped my thrusting, and just gently worked myself back and forth an inch or too savoring my orgasm. I'm not usually that selfish, but I was so carried away with the whole thing.
'Don't stop!' Matt said. He still had his eyes closed and was pulling me against him and starting to work his hips. I pushed as far between his legs as I could, my cockhead too sensitive to keep thrusting.
'Keep going' he said.
'I can't, it's too much.' I pulled out from between his legs, and his penis sprang out too, pointing straight at me. I grabbed his penis and lined it up with mine, undersides laying together, then began to pump both of us together. I wasn't sure Matt liked it but after a couple of minutes he said 'okay,' so I kept pumping. His arms were still around me and he got me in a hug again and began thrusting into my hand.
'Okay, keep going,' he said. I wasn't going to stop this time. Matt was humping my hand harder and harder, and I wanted to make him cum. A couple of minutes later, without warning, he did. I kept on pumping, assuming he'd tell me to stop if he wanted to. 'Oh, yeah.' I looked at his face as he started to cum, and felt very stange. I was holding his cock in my hand but looking at the face of a girl I'd just kissed. He spurted out onto my hand and stomach, and kept pumping into my fist until he'd finsihed.
'Okay, you can let go,' he said. I let him go and he rolled onto his back. 'Wow,' he said, 'you were into that.' I was. 'it was great.'
'It was pretty good, wasn't it?' He said. He sat up and then got off the bed. 'We'd better get out of here,' he said and walked out of my room. I knew what he meant. Any moment one or more of our roommates could walk in. I lay on my bed after he'd left. I couldn't believe I hadn't even closed the door.
We didn't talk about what happened for almost a week. The next Friday I was in the shower. I always got up much earlier than the rest of my roommates, on our side of the suite, especially on Friday, since I had an early lab. Since no one else was likely to interrupt me, I often masturbated in the shower. I heard someone come in and stopped stroking, then Matt stuck his head around the curtain.
'Ha. Want some help?' He took off his boxers and t-shirt and stepped into the shower with me. He was already hard. He stood against me and lined our cocks up then wrapped his hands around both and began to stroke us. It only took a oouple of minutes of this for me to cum, since I'd been well on my way before he came in. I held his hand still and slowly pumped into his fist, and against him, as I came. I then told him to turn round and I pressed against his back, and reached around and cupping his balls in my left hand, began to stroke his with my right. This was sort of like stroking myself and was easy to do. I masturbated him for about five minutes before he came and after he'd finished, I let go of him and he just said 'thanks' and left.
For the rest of that year, we masturbated each other a lot, usually once a week, maybe a little less. Mostly we did it in my or his bedroom between classes when the rest of our roommates weren't around. Sometimes we did it in the shower. Once we did it on the living romm couch. Sometimes one of us would masturbate the other from behind, like we had done in the shower, but laying down, the one doing the masturbating humping betweeen the other's legs. Other times, we would just give each other handjobs, in a sort of 69 position, seeing how long we could both hold out before cumming. Usually, though, we humped. We did it face-to-face. I would get on top of him and he'd have his legs up around my hips with our cocks between our stomachs and we'd get it on. Or one of us would hold our cocks together in his fists while the one on top humped into his hands like they were a girl's vagina. Unlike the first time, these sessions were just a means of sexual release. We were both horny as hell, and having for all intents and purposes made love to each other (though neither of us ever said so) that night after the party, we were comfortable with taking care of our needs with each other. Which was really what it was, rather than Matt wanting me or me wanting Matt, it was Matt can get me off, and he felt the same way about doing it with me. But there wasn't any crossdressing involved, and we never kissed again. That doesn't mean it wasn't intense. On the contrary, we usually simply humped each other like crazed animals.
Senior year we were in another room group, but both of us had girlfriends so we rarely had the opportunity, or the desire, really, to get off with each other. I think we did it maybe three or four times the whole year, humping each time, all in my bed at night when the rest of our roommates were out. After graduation, we've kept in touch for twenty years, and still see each other occasionally, but there's been no jerking off or sex since college.