When I first met my girlfriend’s freshman year roommate, Kaitlyn, I thought she was cute but nothing overly exciting. She had an average body and a nice face, but she wasn't the type of girl that would make every guy look twice. She was also very nice and we got along pretty well. As the year progressed we got to be pretty good friends and enjoyed hanging out at the bar together with friends and whatnot. I never really thought much about having any sort of relationship with her aside from the usual thoughts about threesomes and whatnot that can pop into your head as your trying to pop one of on a lonely night.
Come sophomore year, Kaitlyn stopped living with my g/f because she wanted a single. We were still friends and I'd come over and hang out whenever I wasn't spending time with my g/f or otherwise occupied. Again, nothing seemed to ever get sexual, the only flirting we did was when we were drunk at the bar and even then she would flirt with my g/f and her other friends more than she would with me. This is why I was pretty shocked when I came to be her private sexual show.
It all started one night when I went over to her place to watch TV and help her edit one of her papers. I was sort of intrigued about it because it was a paper on foreplay and how it was shown to have some healing powers, besides just stress relief. It seemed that people who engaged in more foreplay saw decreases in several different types of ailments. Whether it was truth or not didn't matter to me, but I thought it was an interesting paper and would be fun to edit. When I arrived at her place she greeted me in her normal t-shirt and jeans attire. She rarely wore much of anything else. She offered a beer, which I gladly took and we took our normal places in the room, she on her bed and me in a comfy chair. On the TV was a random mid-week drama, nothing too exciting. We made small talk for a while then she gave me paper to edit. It was an interesting paper and she was giving me all sorts of background information as I went through it. It was kind of strange talking about an almost pornographic subject in such a mundane way. As the night wore on we had a few more beers and the TV switched to HBO. We kept talking and everything seemed like a pretty normal night. As the beer took more effect, our conversation became less formal about foreplay and much more casual, talking about what things interested us. Sexual talk wasn't all that foreign too us as it always came up in the bars after a few drinks, but it still got me a bit riled up anyway. It didn't help that HBO was started showing a small marathon of Real Sex. This really got our attention, especially when there was a segment about masturbation, and this club where everyone gets together and watches each other masturbate.
"Wow, I don't know if I could do it in front of someone. I might even be too embarrassed to watch someone do it in front of me," she said as we watched a woman on a table performing for a group of people who similarly had their hands on their genitals.
"Yeah, I think it would be kind of weird at first, but I bet you get used to it. They probably have a drink or two beforehand to loosen up."
At this point, one would have had to have been a complete moron not to notice the tension that was building in the air. Here we were, slightly drunk, talking about and watching sex, a boy and a girl, friends. The one thing stopping us from not inserting pole A into slot B was that neither of us wanted anything to do with my cheating on my girlfriend. But the subject really wasn’t sex at this point, it was masturbation. I looked over at Kaitlyn and saw that she was thinking the same thing, or at least that's what I thought. Part of me wanted to whip my cock out right there and give her a show, but if I did without her asking it would be the end of our relationship. Of course another part of me was so nervous about doing it even if she asked that I didn't know if I would be able to perform.
"What about you, could you do it?" she asked.
"I don't see why not. I mean if you've got a naked girl in front of you doing the same thing, it's not that hard."
She gave me a sly little look and I could see the next question forming whether I liked it or not.
"Could you do it in front of me?"
"Well, I think it would be pretty weird."
"Yeah. But what if I did it too. You know, we did it for each other."
"I'd probably get into it, but don't you think it might...you know...make things a little weird between us, seeing each other naked and all."
"Maybe. but we're mature adults. I think we can handle it. It would be something new and exciting and wouldn't hurt anyone. It's not like you're having sex with me. It's no worse than if you were to jerk off while watching a stripper."
I thought about it for a moment and decided she was right. There wasn't any harm in it, and I did want to see her naked although I wasn't longing for it.
"So...you want to try it now then?" I asked.
"Uh...I guess. Can't be much of a better time. We're already tipsy and in the mood. But I think we should lay a ground rule first."
"Whatever happens, we absolutely do not touch each other while naked. That would lead to bad things. Anything else that comes up...well, we'll see, but no touching."
So there we sat, me in my chair and her in her bad. We had just agreed to get naked and masturbate for each other, but neither of us knew how to make the first move. I sucked up my courage and put down my nervousness and stood up, taking off my shirt. Kaitlyn followed suit, standing in front of her bed and took off her t-shirt, revealing just a plain white bra. We were only five feet from each other and one could smell the anticipation. I worked my way down to my boxers and watched as she took off her jeans. She was wearing a set of normal panties, in sky blue. Although I wasn't totally hard, I still was stiff enough to make my boxers tent and Kaitlyn noticed because her eyes were fixed on my crotch. I was staring at her breasts and when our eyes met we gave each other a nervous smile. Kaitlyn was the first to take the really big step as she unhooked her bra and let it fall onto the bed. Her tits were a small B-cup, with half-dollar sized nipples. We both took off our last articles of clothing at the same time. Her dirty blonde hair gave her dirty blonde pubes, which, although thick, were cropped to a strip about an inch wide. The sight of her naked body had my cock standing at its 6 1/2" height and my hairy balls tingling. I had this urge to take her in my arms and run my hands over her smooth skin, sucking on her nipples, but I resisted making my cock throb with lust. My body shook with nervousness and sweat popped out on my forehead.
I sat down on the chair and watched as she sat on the bed, legs slightly spread and her feet on the floor. The mixture of weirdness and lust I felt drove me nuts. She kept staring at my cock as I flipped between her tits and pussy. I reached down with my left hand and gave my cock a long stroke from head to base, letting a pent-up gasp escape my lips. She watched intently and put on hand on her breasts, massaging it and tweaking the nipple. Thus the fun began. I slipped my other hand under my balls and she spread her lips with her fingers. We gave each other bigger smiles and relaxed a bit as pleasure overcame us. The sounds of the sex on the television motivated us and I gave my cock several more strokes, starting a rhythm that was supplemented by a good massage of my balls. Kaitlyn worked her fingers around her pussy slowly, then began to explore her hole and tease her clit with making sure the other hand paid attention to her aching nipples. Neither of us said a word, communicating only with gasps and sighs and smiles. Kaitlyn really started to get into it, moving her body, licking her lips spreading her legs wider. The sights and sounds before me drove me nuts and within 5 short minutes I could feel my cum building. I stroked faster, grunting and moaning until my cock exploded and my warm cum splattered on my chest. It had been a little while since I jerked so it was a few long streams of jizz that shot out and streaked my stomach. A surprised "oh!" came from Kaitlyn and I sat with my cum on my stomach and watched while she brought herself to the top then slowly came down, easing her pussy and tits back to a state of normalcy.
When she was done, she threw me a box of Kleenex and I wiped up. As I did, she got dressed and I followed suit. Once dressed we sat again, both beaming.
"I want to do that again," she said.
"All the time. At least once a week if not more. If you feel the urge to jerk off, call me. Well, I guess not every time...I'm sure you'd like to do it by yourself a few times."
Feeling that there wasn't much left to do, we gave each other a small hug (touching was allowed when not naked) and off I went. It was over a week before we did it again and during that time we were a little on edge with each other whenever we were together, but not so much as to be noticeable. Every time I saw her all I pictured was her legs slightly parted and a pair of hard nipples. The next time we did it, we took it a little slower and made it last longer, but nothing really changed. We were in the same positions and did pretty much the same motions. Although I came I left the room with so much sexual energy that I ravaged my g/f when I slept with her that night. Over the two months we did it a couple of times a week and I noticed that if I had sex shortly after it was amazing because of all the build up urges to do more with Kaitlyn that we would allow. As we got more used to doing it with each other, we relaxed a lot more. When we were together outside the room we no longer had any tension and I didn't constantly picture her naked. When we were naked we were now able to talk to each other while doing it, sometimes saying dirty things, other times holding perfectly mundane conversations while we pleasured ourselves for each other. Those couple of months also saw us change things up a bit. Sometimes I would jerk off standing a couple of feet in front of her. Other times she would lay on the floor and do it while I stood by, near enough to feel like I was towering over her, but not near enough to chance touching. A third position that we tried was in front of her full-length mirror. She got on all fours and spread her ass and masturbated (giving me my first good look at her puckered asshole) and watched in the mirror as I jerked off behind her. I wanted to grab her ass so bad and start fucking her doggie style that we had to limit how often we did that position for fear that lust would take over.
Two months into our relationship came the first big change. One day after I had already gotten naked and stroking, I noticed that Kaitlyn hadn't removed her panties. I gave her a look and she told me not to worry. As she watched me she rubbed herself through the material, then slipped them off and threw them at.
"I figured you’d want a whiff or a taste."
I grabbed her panties and brought them up to my face, putting the crotch against my nose. I took a deep breath and inhaled a bit of her delightful musk.
"Mmmmm...keep doing that. It's hot watching you with my panties."
Now that I had the go, I stuck my tongue out and licked at the wet spot on them. Although it was masked a bit by the taste of the fabric, I still enjoyed a hint of what Kaitlyn's wet pussy would taste if my face was locked in between her legs. For the rest of the session I kept her panties on my mouth and nose while I beat my cock furiously. I let go one of the best cumshots I'd had in a while and soaked my upper leg and lower stomach. I threw her panties back at her and watched as she put them on as I cleaned up.
"That was awesome," I said to her.
"Yeah. I know that seeing my pussy a couple times of week must be driving you nuts. I just thought I'd share."
"Thank God for that. It was great."
We managed to incorporate this new twist into our sessions pretty quickly. She wouldn't do it all the time, but when she did it was wonderful. She also started taking them off and pushing them into her pussy, covering them completely with her juices. I always made sure I washed my face and hands very well after those sessions so that no one would smell her on me. Not very long after, she had me use the panties while jerking off, wrapping them around my cock while I pumped. Then she took the natural next step and had me cum in them. It was her way of getting to taste me as she always licked my cum out of the crotch of her panties when I threw them back at her. After nine months of masturbating together I bought her a dildo and had her incorporate it. Watching her slide onto the fake cock for the first time made me cum in record time and she kept fucking herself until I got hard again and was able to blow another load. After buying her the dildo, I actually got my first chance to watch her do something with her asshole. She never really touched it at all, but with the dildo she lubed it up and slipped it right in, slowly taking every inch of it. That night was another night where I shot off two loads because it was just too damn hot. My g/f was the recipient of tons of hot sex because of all these things. Each time I did something new with Kaitlyn or had a really good session I was so wound up that I nearly tore apart my g/f during sex. I think that even if she did find out about me and Kaitlyn that she wouldn't want us to stop because the sex she was getting was so damn good.
Our masturbating had been going for well over a year and a half before we took the last advance possible, at least possible to us. We were doing the "doggie style" position with my jerking with her panties and Kaitlyn jamming the dildo furiously in and out of her pussy. There was porn on the TV and we were talking quite dirty to each other. Everything was building up to a massive orgasm for both of us. It was right then when she cried out for me to cum on her ass. I was so shocked that I almost blew my load into the air. Instead I stepped forward and she arched her ass into the air. I lost it right then and blew a huge string of cum right across her ass, some it going to far and dropping on the floor. The rest of my cum I pumped onto her ass and back as she moaned in delight. She reached back and stuck her hand right in a puddle I had made, then licked her fingers dry. It was so amazing to do and watch that I came the closest to making love to her that I had ever been. Instead I backed off and we both cleaned up. After that incident she allowed me to cum on her every once and a while. Usually it was on the ass or the tits, but occasionally I stood mere inches in front of her, pumping my cock in her face until I exploded onto her face. The tip of my cock was no more than an inch from her lips on these days. We each had incredible willpower to not let it go any further than that.
What started a couple of years ago as an innocent drunken stunt turned into a pretty good time. Things have slowed down a bit but we still see each other a couple times of month even though we both are happily hooked up with another. We've tried a few other positions (standing in front of the mirror together was interesting) and a few other places (opposite ends of a bathtub was fun) and things couldn't be better between us. Who knew that masturbation could fuel such a wonderful relationship?