As a college freshman I was perpetually horny. I roomed with a guy named Steve and we were both, admittedly, somewhat nerdy. Neither of us had any luck with girls during the year, although we each had had one sexual experience in high school (me a hand job from a friend's 13 year old slutty little sister at a graduation party that lasted all of about 30 seconds before I came, Steve being jerked off by his cousin from Wisconsin during his junior year). He and I, being college guys, often spoke about sex, and kept a large stash of porn magazines in our room. He brought most of them from home, and told me his friend was able to get him just about any kind of magazine he wanted. Almost every night before we went to sleep we would be in our beds, flipping through mags, talking about girls and getting horny (I know I was) and then jacking off before falling to sleep. We never talked about jerking off, never admitted we did it and never did it in front of each other. It was always after the lights went out or when our schedules allowed us to be in our room alone. Even though we went to great pains to be quiet when the lights went out, it was pretty obvious what we were both doing. Steve was VERY quiet, but on two occasions I distinctly heard him grunt as he was coming. There were a few times I tried to be loud on purpose to see what he would say or do, but nothing happened. One day when he was at class I looked between his bed and the wall and found about 50 used and crusted tissues; at least I had the decency to throw mine out the next morning!
The last few weeks of school we spent more time at parties and hardly any time studying. One night before we went out we hatched a plan where we would try to get our friends Peggy and Heidi (who were roommates, and also kind of nerdy) to come back to our room after a big party at a dorm across the quad. The plan was to leave our porn magazines out where they could see them and we would try to engage them in a conversation about sex and see where it led. Peggy was cute, with short brown hair and a great smile, but she had a rather large butt and wide hips but was slim. Her big backside fascinated me, and she always accented it by wearing tight black jeans. She was shy and pretty and tall, and although she had smallish breasts and I preferred large ones, I had fantasized about seeing her naked many times before. Heidi was almost the opposite of Peggy; she was short and heavyset with big breasts, close-cropped short blonde hair and she was very loud, gregarious and outgoing. Her laughs could be heard up and down the girls' dorm hallways. She was never afraid to speak her mind, and could be very funny at times (and obnoxious at others).
The party was great, and lasted until well after midnight. We hung with Peggy and Heidi most of the night, and were confident our plan was going to work. As we walked back towards our dorms, we invited them to hang out in our room for a while. Heidi was gung-ho, but Peggy begged off because she was feeling 'under the weather'. So we dropped Peggy off at her room to make sure she got in OK and then headed to Winchester Hall (our dorm). We were pretty rowdy as we went down the second floor hall, and went into our room laughing and carrying on. Steve flipped on the TV and I flopped on the bed while Heidi sat in the chair at my desk (this was a VERY small room, as most college dorm rooms for freshman are). We had 'strategically' placed various magazines around the room; a small neat stack under my chemistry book on the corner of my desk, a few underneath the nightstand between our beds, and a few on the window sill, poorly hidden by the curtain. In less than 10 seconds Heidi spotted the ones by the window and grabbed the one off the top.
'You guys are a couple of pervs!' she said, laughing. Us being pervs didn't stop her from flipping through it, pausing occasionally to mutter comments like, 'Jeez!' and 'Oh my GOD!' She was in rare form, loudly telling us we should 'go out and try to get some instead of sitting around and jerking off looking at naked women' and 'I can't even imagine what you two must look like whacking it.' Like I said, she was funny and wasn't afraid to say what was on her mind.
Our conversation was pretty light-hearted and we sparred back and forth with her, pressing her to tell us if she liked any of the pictures. She finally confessed to liking some of the 'non-standard' magazines (we had some Penthouse and Hustler, but also some that showed EVERYTHING including insertion and one that actually showed guys coming) that featured naked guys with erections. As we talked more she became flushed (she had a very light complexion, and it was pretty easy to see she was either embarrassed, or excited, or both). We began comparing notes and slowly revealing our experiences and masturbation habits. I confessed I started when I was 13, Steve told us he used to do it in the woods behind his house. Heidi was MUCH more shy, and then she blurted out that she usually did it in the shower with her hands. I talked about the hand job I had gotten, embellishing it to say that I had actually eaten out the girl while she did it to me (I had not). Steve told us how his cousin was a slut too, and she almost forced him into taking his pants off. He said while she did him she played with herself and that when he came he shot all over her leg.
Heidi told us, laughing and blustering along the way, a story of how one time when she was 14 she masturbated with a frozen hot dog and how it had broken in half right before she was about to orgasm. We asked her all kinds of questions, such as where she had done it (in her room when her parents were out), if she liked it (she said it was great except it broke because it defrosted while she was 'doing it' and got soft) and how she got it out (it wasn't stuck in too far, she told us). I was completely boned at that point, and I'm sure Steve was too. She told us she had never been with a guy expect to French-kiss and one time she felt a guy thru his pants while he played with her tits until his mom came down the stairs of the basement and that was that.
I casually picked up a magazine from next to the bed and Steve did the same. We spent a few silent moments looking at pictures and wondering what to do next. Finally Steve blurted out (which was VERY uncharacteristic of him, he was very quiet and reserved), 'Have you ever seen a guy do it?'
She said he was a dope that she just told him the most she had done was to feel a guy through his pants. She did go on to tell us that Peggy had seen a guy in her neighborhood back home do it and told her all about it, and she thought about seeing guys jerk off a lot. It seemed like we had reached a point where Steve and I were either going to 'do something' or this whole thing would just die down and she would leave and go back to her dorm.
'We'll let you watch' I somehow choked out. 'But only if we can watch you.' Steve looked at me like a deer in the headlights, like I was crazy or mad or insane. I had never done or said anything so bold in my life. I was pretty sure she was going to tell me to go screw myself and that I was a perv and that she would be really pissed, but I guess I was so horny and desperate I was willing to take the chance.
'No way,' Heidi said. 'No way I'm doing that in front of you guys. I mean I'm horny and everything, but it's not like I'm going to pull down my pants and diddle it for you.' It wasn't as bad a reaction as I expected. And she said she was horny. Wow, that was almost like hearing I had won the lottery...! But it was still a no. I was willing to let it go and save any potential embarrassment.
'Come on, please!' Steve said. I was shocked. He was practically begging. He must have been hornier than even I was. 'We'll do ANYTHING, please?'
'Nope!' was all Heidi said. We began to debate and bargain back and forth for several minutes, offering to bring her breakfast to her room for a week from the cafeteria, to clean her room for a month, to take notes in Trig III for her, everything but actually paying her to let us see her masturbate. Now keep in mind this wasn't some hot model we were pleading with; Heidi carried about 170 pounds on her small frame, but at that moment Steve and I couldn't care less. We saw her big breasts pushing out her tight tshirt and her fat ass looked like the best thing we had ever seen in our lives.
Finally Heidi said, 'The only way I'd do it would be if you guys jerked EACH OTHER off, not just yourselves. If you get naked and do it to each other, then I'll diddle for you.' I loved how she called it 'diddling'. She put it out there with the tone and attitude that said 'There's NO friggin' way these guys will do THAT.'
Steve and I looked at each other, dumbstruck. We didn't know what to say. I had NEVER thought about touching a guy's prick before, much less jerking him off. BUT, as I said I was so horny at that point I was pretty much open for anything. For a guy like me these kinds of opportunities come around, oh every 10 years or so and you have to take advantage of them. Before I could say anything Steve said, 'I'll do it if Chris will'. That's all I needed to hear. A hand on my dick and seeing a girl masturbating sounded good to me. I didn't care if it was a guy's hand doing me. I just needed to get off. (Every time I watch 'American Pie' now and the scene with the 2 hot girls promising to perform lesbian sex if the guys will kiss and jerk each other off instantly brings my experience back to mind like it was yesterday - even though it happened back in 1981).
'But if we get naked you have to get all the way naked too' Steve said. 'You can't just pull your pants down a little and do it. If we're gonna actually jerk each other, it's only fair.' To make a long story short, she immediately protested and the whole deal was almost off. But Steve masterfully persuaded her after another long 5 minutes to be naked; I was very impressed.
When the 'deal was sealed' Heidi immediately became more domineering than I had ever seen her before. She instructed us to take our desk chairs and place them next to each other facing the bed. Again, I think she was confident we weren't going to actually go through with it. She sat facing us, and told us to strip to our underwear and sit down. I was a boxer guy and Steve wore briefs. While we had seen each other like this dozens of times before, we were both nervous as we unzipped and unbuttoned and removed our pants and shirts. As we sat down my eyes drifted to his crotch and his hard on was very visible, outlined by the white cotton of his briefs. My boxers were tented. We both looked at each other a laughed nervously. Heidi was visibly taken aback, but also was checking us out. She was obviously nervous we would have the balls to actually go all the way.
'Now touch each other through your underwear'. I was scared shitless, and told Heidi that I wasn't going to do it until she was in HER underwear. No deal, she said. She wasn't taking anything off until we were naked and touching each other's dicks. I guess Steve and I forgot to iron out the 'details' of our arrangement. When she told us no deal, her voice had noticeably changed from one of confidence and dominance to a softer, more 'willing' tone. The atmosphere definitely changed when we stripped to our underpants.
Steve moved first, and put his left hand on my crotch. No grabbing, no rubbing, just put his hand over my erection. I thought I would come right there. Just feeling another hand on me kicked my horniness into a higher gear. We were close enough that our legs were touching, and I moved my right hand over to his crotch. I rested it on top of his erection, and as I did I felt him jump a bit, and his head rolled back momentarily. I was surprised I could feel the heat of his erection right thru his underwear, and the hard lump actually felt good in my hand. I was definitely turned on, and not off, by this experience. We both began to move our hands, feeling and probing, and then we looked at each other and laughed. Heidi was saying, 'Oh my GOD I can't believe you guys are doing it!!!' and she was blushing furiously at that point. Her nipples were poking thru her tshirt and it was very obvious she was aroused. I felt Steve's hand snake into the fly of my boxers and when his hand gripped my cock I was in heaven. The only thing I was worried about was shooting too soon. I worked my hand under his waistband and felt the warm skin of his cock. It was different than mine; I am small (about 5') but rather thick with a bulbous head. Steve's cock was much longer (probably about 7+') but much slimmer. It felt nice in my hand.
I lost track of Heidi's promise momentarily, and then tugged at the waistband of Steve's underwear. He read my signal immediately and whipped his underwear off in less than 2 seconds. I quickly followed. We stared at each other's cocks for a full 3 or 4 seconds then turned to Heidi and told her it was her turn. She didn't say anything, and didn't protest. I think she was in shock. I really believe she thought that there was NO WAY we were going to do what we were doing and she had had no intention of stripping naked in front of 2 nerdy guys. She was literally staring at our cocks with her mouth open (not drooling but almost). Now that we had actually stripped naked she was seemed to become 100% caught up in the moment and the horniness just like we were. She pulled her tshirt over her head (after a short struggle because it was so tight) to reveal not just large but MAMMOTH breasts encased in a pink lace bra. I began slowly stroking myself (Steve and I had not yet 're-engaged' with each other's cocks...) and as Heidi stood up, unsnapped her jeans and pulled them off she said in a husky voice, 'Hey you guys have to do it to each other, not yourselves'. In an instant Steve's hand was on my cock, and as I reached over for his I noticed he had leaned back on the chair with his legs splayed wide in front of him. His cock was jutting straight up and his balls hung off the edge of the chair. I had complete and open access to his privates, and decided it looked like a good position and did it myself. As we settled in, we quickly got the hang of jerking off another guy, and I was completely and totally aroused to touch and be touched. We were both slick with pre-cum, Steve actually more than me as it seemed to be leaking out of the tip of his cock in a small but steady stream. I, on the other hand, would every 10 or 15 seconds have a large drop appear on my cockhead and Steve would use it to lubricate me.
Heidi muttered, 'I can't believe I'm doing this' as she reached behind her and unsnapped her bra. She let it slip off her shoulders with ease, and her nipples (which were standing at attention) were in direct proportion to her breasts; her breasts were huge white mounds, somewhat saggy but as large as you would see in some of the 'Big Tits' magazines. Her areolas were massive, at least the size of a silver dollar and they were up rather high on each breast as opposed to in the middle (kind of hard to describe). Her nipples were completely erect and stood out a good half inch. She reached down and tweaked them and hugged herself with one hand as the other went between her legs and she began to masturbate through her panties. She wore large, tight briefs, pink ones that matched her bra, and as her hand worked around her privates she pressed her legs together and moaned a little, then laughed. I said she had to take them off and she only replied 'Hold on a friggin' minute'. She turned and with her back to us slipped her panties down and off. We were about 2 feet away from her large white ass as she bent over to pick them up (I think she did it on purpose) and we got a GREAT view of her pussy. She turned around and faced us and the first thing I noticed (aside from her ample belly and great tits) was that her pussy was completely shaved except for a very small patch high up her pubic area.
When she turned around Steve's began to noticeably go faster on my cock, and I followed suit. Heidi sat on the bed and said in a low voice, 'We're all a bunch of pervs' and as she did her hand went between her legs, which she had spread slightly. Her middle finger disappeared between her lips, and she sighed loudly. She leaned back on the bed slightly, supporting herself with her right hand behind her while her left hand began to rhythmically 'diddle'.
So there we were, the three of us. Steve and I jerking each other and Heidi playing with herself. We were all lost in the moment, and looking back we probably stayed in our positions for about 10 minutes (a pretty long time). A few times I had to have Steve stop for a minute because I didn't want to come yet. Heidi became increasingly vocal, and as she became more turned on her legs spread more and more until she was spread open right in front of us, her middle finger rubbing up and down her lips and occasionally dipping inside, and she spent more and more time working her clitoris which was sticking out prominently. She was very wet. Her moans grew and I knew she was close, as were Steve and I. I took a final bold step and disengaged from Steve's hand, stood up and stepped forward. Heidi looked at Steve and me with complete lust in her eyes as we stood on either side of her, and jerked ourselves to orgasm. Somehow we all came within only 10 or 15 seconds of each other with Steve shooting first, his come arching out in copious amounts all over Heidi's left tit and thigh. I was actually straddling her right leg and squatted down and began to hump the top of her knee and thigh which sent me over the edge. I also shot a lot, at least 3 liquidy streams, all over her belly and leg, and on my bed. It was fantastic.
After Heidi came down from her orgasm she said it was cool and fun and all, but she was pissed that we came on her. 'What do you think this is a porno movie, you pervs?' Steve got a towel and we offered to help clean her up but she didn't want us touching her. We dressed and she left, and when we saw her the next day she acted like nothing had happened, and nothing did happen with her after that. But over the next 2 weeks before school ended for the semester, Steve and I jerked off together almost every night, and on the last night actually gave each other head. Unfortunately he transferred to another school the next fall. BUT, I was able to hook up with a very cool girl who was quite hot (for me at least) and we lived together for the second half of my sophomore year and we had sex almost every night.