[MFM] My roommate's gf (Long) | 2016

So this is a story I've wanted to share for a while, just to get it off my chest. It happened back in 2007 and I have not been able to tell the story to anyone, but now I found a place to do it! This might be a long story but I don't feel like splitting it in parts.

So a little about me that will be relevant to this story. I was a fairly athletic, decent looking guy for most of my life, but also a bit of a geek personality wise, and also a bit on the shy side, especially around the opposite sex. As far as I knew nothing was special about me, but when I was 19 I learned that apparently I did have something a bit unusual. Apparently I was lucky enough to be above average in the endowment department, especially in terms of girth. This was news to me, and learned only from one trashy girlfriend that I otherwise regret dating.

One would think this would really boost my sex life and my confidence, but it really didn't. I was still a bit too awkward to ever bring it up when it mattered (and how would I know if the woman would be the type to like that thing, or think I was a pig for bringing it up).

Well I was in college and horny all the time, and was not having much luck with women (mainly because I was still so awkward to approach them). Well I stumble across an adult dating/sex site online. I decide I have nothing to lose so I sign up. I had a little luck on there but not much. I also got a lot of attention from men even though I was listed as straight.

Well one email from a guy got me curious enough to answer. He was in a similar situation to me, even more endowed than I was but just not having much luck because he said he wasn't the most attractive guy out there. He suggested we might try to team up and attract women for a MFM threesome. Since I was not having much luck at that time I figured we could give it a try. We both were interested in doing a threesome anyway, so why not.

We met up to take some photo together (awkward as hell at first). After we finally managed to get ourselves at attention and get some photos snapped we signed up for a new account, and put the new pics in our personal ones as well. We started to hang out a bit, but always over at his place and only maybe once a week, he lived not too far from me so it wasn't too difficult. We didn't have a ton in common, so we basically just checked the joint account and watched ESPN some.

We started getting hits from our new profile and a couple from our own. Well he gets a message on his personal profile from a 21 year old girl who seemed better than what we were used to seeing on the site. She sent a lot of body pics, but didn't send any face pics, but we agreed to meet her somewhere to see how we got along. She tells us she will be wearing a green shirt we had seen in one of her pics. I knew she was red headed and something kept making me think she looked familiar, but she was adamant she didn't want to send a face picture so we didn't pressure her.

I guess at this point I should tell you a little about my roommate and his gf. The title of the story already gave it away so no need to save the surprise. My roommate was a guy I knew through high school. We went to rival schools and played a lot of sports against each other and were friends, but not super close. In college we decided to room together. He was a very cool guy, easy to make friends and always had plenty of ladies. But this one girl named Anna, a redhead who was cute but not as hot as some of his other ladies, somehow locked him down. We couldn't figure out why. They fought a lot and didn't seem to really have any kind of common ground, but they were dating for about a year at this time. She was cute, but other than a fairly nice ass wasn't too special in the looks department. I honestly didn't really care for her that much.

So flash forward to the meeting. My partner in crime, who I'll call Silo from now on (Beerfest reference there!), and myself went to the meeting place, a nearby pub on the night we were supposed to see her. At the time I was excited because my roommate was out of town on a trip with his family so I'd have the apartment free. Little did I know the significance of that before we met!

We walk into the pub and started looking around. We had sent her face pics so she knew who to look for. Then I see a girl waving at us from the corner of the bar. My first thought it "Shit, Anna is here", but then I saw her shirt and it dawned on me. I was seriously stunned for a bit, and Silo was asking me what was wrong. She walked up and gave us both a hug and I was still stunned to say the least.

Finally I just look at her and ask her "You knew the whole time?" and then "And you're sure Roommate doesn't know?". She told me yes on both accounts, and that she didn't send a face pic because she didn't want me to back out on her. I was a bit unsure as to what to do, but she grabbed both of us and pulled us over to the bar. We had some drinks and she excused herself for a minute to answer the phone. I told Silo what was up. He told me we could back out, but for some reason (desperation honestly) I said no, let's do it. Plus it was kind of hot in it's own way.

So after an hour or so we decide it's time to make things happen so we head back to my place. It's still a bit surreal but there has been enough innuendo to get me going at this point, and not thinking of the consequences. We get inside and I lock the door and before we are out of the living room Anna tells us to get naked because she want's to "See those dicks in person, right now!". That pretty much got us both turned on so we complied.

She starts to make out with us while lightly playing with our cocks using her hands. Then she gets on her knees with us still standing by the door and starts to suck one, then the other. She asks us if we will hold each other's dicks while she sucks. This is not something I would normally have said yes to, but the way she was acting and the way she said it we agreed and did so. Luckily that would be about the only awkward moment for the night save one other thing.

She then starts to try and suck both at the same time (knowing she couldn't) but she did rub them together a bit, which was both a huge turn on but also a bit awkward at the time. After this went on for a time, she stripped down and we began to work on her. We led her to the couch and she sat down, and we both sucked and licked her nipples while playing with her clit with our hands. After a bit of this I went down on her while she sucked Silo, then we traded off.

She also asked that we lick her ass (a huge fantasy of mine and the firs time I had ever done it!). Silo said he wasn't comfortable doing it, but I went ahead with it.

After a time we moved on to actual penetration. Silo went first while I let her stroke me. It took a bit of patience but he eventually was going hard, with her legs spread on the couch. Then we swapped and I did the same for a bit, but she started to suck him. Then he sat on the couch and she rode him while sucking me.

She then asked if we wanted to do anal, which I did. So we changed positions (moved the coffee table and did this on the floor) and I took her from behind while he was in front. It was a bit hard to do given where we were at but it worked out in the end.

Then she wanted to try DP but wasn't sure it would work. I sat on the couch and she rode me in her ass and Silo attempted to enter from the front. But the positioning was awkward and it just wouldn't work that well.

Finally we decide to try it a bit differently, and managed to find a workable position where she rode him on a chair and I entered from behind. It was fun, but hard to effectively do. We did it for a short while, then she decided she wanted to go back to one at a time there. We did that switching positions a few times, and next thing we know it's been about an hour and a half. Silo had come close to cumming a few times at that point, and I had at least once, so we all figured it was time to finish. She asked us where we wanted to do it, and we asked her if she would let us cum on her face. She agreed and got on her knees. She sucked Silo until he finally came, and he hit her mostly on the lips/chin. Next up was me, so she started sucking me as well, but I wasn't quite able to get off from her blowjob at that point. She ended up stroking me off and I hit mostly on her forehead, but somehow didn't get any in her hair (yay me lol).

After that point we sort of rested for a bit and she cleaned off some. It was late and Silo decided to go home, so Anna and myself stayed behind and took a shower together. At about that time it dawned on me as to what had just happened and I started to freak out a bit. She told me not to worry and that we could really enjoy the next few days without Roommate there, and that she and he were going to probably break up when he got back anyway.

That pacified me enough and that night she ended up sleeping in my bed. Silo came back the next day and we had a repeat.

Well Roommate finally came back and it was a bit awkward when they didn't break up as advertised. Silo and myself kept trying on the site, but seemed to only attract older couples rather than anyone we were really interested in. Eventually we just gave up on it altogether. Whenever Roommate went out of town Anna would try to get us all three together, and I had to admit it happened more times than I'd like to admit. She and I even had some one on one time when Roommate was at work and she had slept over.

Finally he broke up with her and got a decent girl. Anna and I saw each other a few times, but always careful not to let Roommate know. Silo in the meantime had found a steady girl himself so we no longer did our threesome adventures together. I still talk to Anna once in a blue moon, but not often. It left a bit of a mixed feeling for me. On one hand that stretch of time is the hottest, sexiest time of my life and I often think about/get off to it now. On the other hand I feel extremely guilty about it too. At the time I was so sexually frustrated and horny I ignored it, but when I finally got straightened out I couldn't help but feel bad about what I did.

So that's my story, way too long I know, but I feel better for telling it! Hope someone at least gets a bit of enjoyment from it!