My Girl[f]riend gets comfortable with my room[m]ate

My girlfriend Lauren (22/F) was hanging out at my place, drinking with me (26/M) and my roommate Sam (28/M) at the time. Lauren was(is) probably 5’2″ and 110 lbs, Filipino with a cute face but not a crowd stopper. However, she has a body that I think is just perfect, in shape with great curves for such a small woman. Since we were just staying in, and it was the summer, she was wearing just a tank top and booty shorts. I know my roommate thought she was hot, and he had a thing for asian girls, even though his girlfriend was white. Since we were long distance at the time, Lauren usually wasn’t around, so it was a treat to have her living with me for a week, and my roommate certainly did not mind. She was always friendly with him, and playful, and she knew he thought she was hot, so she would try to act really sexy around him. He was a very nice guy, and had a girlfriend, which made him the perfect target for Lauren, because she knew she could flirt heavily and he wouldn’t do anything about it.

Part of why he thought Lauren was so hot was because I had shown him private pictures of her (at her encouragement, although Sam didn’t know that), so he was well aware of how nice her body was. Lauren had a thing about showing off her body, and she got off on knowing that guys she knew were seeing her naked. It was especially exciting for her if she could play the innocence card, and act like a sweet asian college student who would NEVER share her pictures. It started out with her sending a picture of her in her posing in her underwear, and telling me to show Sam if I wanted to. I did, and she was obviously happy when I told her that he thought she was super hot. She continued to send photos when she knew we were both hanging out at the apartment, and they got progressively naughtier, from underwear and lingerie, to artful topless shots, to pictures of her completely naked, and finally, shots of her spreading her legs for the camera. The pictures were very very hot, and Sam was under the impression that I was the luckiest guy on earth.

He had also mentioned a time or two that his girlfriend had sent him dirty pictures…which was shocking, because she seemed like a total prude. He never had returned the favor though, so I hadn’t seen pictures of his girl.

Anyway, we were playing Madden and pounding beers while Lauren half watched us and screwed around on her laptop. Me and Sam are about evenly matched, so things normally get pretty heated, with close games the norm. We were also getting pretty drunk by our third game. Normally we bet house chores or beer purchases on the games, but an idea drifted into my drunken head that would get Lauren involved and call her bluff a bit. Right before we started the rubber match, I told Sam I had an interesting idea for a bet. I win, and he has to show me and Lauren a dirty picture of his girlfriend. But if he won…Lauren would show him her tits, and not a quick flash, but she would take her shirt and bra off.

Lauren gave a protest, squealing “thats not fair!!” I just said “dont you have confidence in me, baby?” and knowing that it would actually turn her on to be topless in front of my roommate, she agreed. We shook hands on it, and began to play. Lauren was off her laptop now, watching intently. The score was tied 14-14 at halftime, and all three of us were pretty tense. I also noticed that Lauren’s face was quite red, though I dont know if that was from the drinking (asian glow) or nervousness. The second half started, and Lauren decided she would help the cause by distracting him. She walked over to the tv, and leaned wayyyy over, giving Sam a deep look at her cleavage. He was focused, though, so she turned around, and asked Sam “do you ever do this with your shorts? it feels kinda good!” while she faced away and rolled up her short legs until they were wedged into her crack, showing off the majority of her butt. I could see him glance over between plays, but he REALLY wanted to win…and to be honest, I sort of wanted him to win too.

The game ended up being a bit anti-climatic, because i threw two straight interceptions (one on purpose). When it ended, Sam did a full on fist pump, then got a big ass smile on his face. Lauren looked at him and was like “you didnt seriously expect me to take my shirt off, did you?” Sam turned to me, and was like “c’mon man, pay up” but before I could say anything, Lauren said “fine fine fine” and stood in front of the tv. She pulled her tank top over her head, revealing a cutesy black pushup bra. Then, looking straight at Sam, she reached behind her and unsnapped her bra, letting it fall to the floor. Her beautiful B cup tits were finally out for my roommate to see, and they were glorious. Lauren was clearly turned on, because her nipples were fully erect.

Lauren looked so damn cute standing there in her little booty shorts and nothing else, and I knew that she fantasized about showing off for my friends in person, so this was a big moment for her. I knew the shirt wouldn’t be going back on, and it was only a matter of time before she would need to be taken care of in the bedroom. I figured I might as well push it a bit, so I declared that this event called for shots. Lauren declared her approval, and walked to the kitchen to grab a bottle of whiskey and shot glasses. I glanced over at Sam, and his eyes were unflinching, watching Lauren’s every move.

We took the shots, and it was sort of unclear what would happen next, so Lauren took charge and turned our game off and turned the TV on. Its Always Sunny was on, which was one of her favorites, so she turned off the light and sat down on the couch between us, and cuddled up with me to watch. It was sort of awkward, because she didn’t address the fact that she was topless, but I wasn’t about to say anything, and neither was Sam. We sat and watched for a few minutes, and I openly played with her tits while we sat there. However, I also really had to pee. So I removed Lauren from me, and went to the bathroom. As I was walking off, I heard Lauren say “well I guess its your turn to cuddle!” to Sam. I quickly went to the bathroom, but instead of coming back, I lingered in the hall silently, peeking around the corner.

Lauren was laying on Sam’s lap, her beautiful black hair spread on his legs. Sam’s right hand was on Lauren’s side, under her arm and maybe 4 inches to the right of her perky right boob. I knew what was coming, and yet couldn’t believe that Lauren would actually do it. But it was actually what she wanted, and I had no problem letting her.

She took a big sigh, and rotated her body, sliding her tit right into his hand. I saw his hand cup her tit, and then give it a squeeze. I saw Lauren close her eyes, showing how turned on she was by the situation. Sam continued to play with her boob, rolling her nipple with his fingers, and after a couple minutes, was openly fondling both her breasts while she quietly moaned. I also saw her turn her cheek in his lap, and I knew she was enjoying the feeling of his dick under his shorts.

At this point, I knew Lauren would be over the top horny, and sure enough, I saw her hand slide down and into her shorts to touch herself. As she fingered her clit under her shorts, I could see her writhing in his lap, and he began tweaking her nipples. I knew that she wanted Sam to touch her. Lauren and I had discussed before how far her “teasing” was allowed to go, and she was allowed to be touched, but couldn’t do anything to the guy. We had basically agreed that if she is teasing another guy, and I’m around, then she could go as far as letting the guy touch her pussy. Sure enough, I heard her say “Touch me, Sam,” before reaching her now wet fingers up towards Sam’s face and putting one in his mouth.

I knew that Sam had jacked off to pictures of my girlfriend’s pussy, and had a thing for asian girls, so this was also a dream come true for him. But to my shock, I heard him say “umm I don’t want to cheat on Amy.” Not taking no easily, I heard Lauren say “I won’t tell her if you don’t.” But Sam didn’t budge, and continued playing with her boobs (ignoring the hypocrisy, obviously). Lauren slid away from him, and she briefly saw me and made eye contact before looking back at Sam. I knew her well enough to know that she was completely gone, and thus completely focused on her own sexual gratification. Lauren stood up, and I’m sure Sam had thought his fortune had expired.
But Lauren looked right at him, and said “well you don’t consider it cheating if you watch porn, right?” Sam said no, and Lauren, in her chipper, cutesy voice, said “good!” She then reached down and slid off her shorts and panties, standing right in front of him. Her bare shaven pussy was maybe two feet in front of him, and as he stared at it, she quickly glanced back over at me. Then she turned and faced away from him, and bent over slightly, giving him a perfect view of her bare bubble butt. Sam, breaking his own self-imposed rule, stuck his hands out and grabbed her smooth butt cheeks, getting in a good squeeze and spreading the cheeks enough to get a peek at her tight little asshole. She pulled away, and quickly admonished him, jokingly. Then she sat down on the other end of the couch from Sam and swung her legs up towards him on the couch, opening them up so he had a clear view of her pussy, with her feet resting on his leg. I couldn’t see her from this angle, so I dropped the pretense and walked out and around the couch so I could see the show.

I’ll mention at this point that Lauren has told me in our after-sex pillow talk that one of her fantasies is to masturbate while a group of men watched. She said her ultimate dream would be to do something like fuck herself with a dildo at a frathouse while the frat boys all watched. Obviously, that wasn’t realistic, because it would both be unsafe and guys might videotape it and post it, but I knew that her ultimate dream was having other men watch her.

Well, she was living close to her dream there in my apartment. The room was sort of dark still, so I turned on a lamp behind the couch so we could see her better. Lauren reached down and spread her pussy lips wide for us, showing us everything. She stuck two fingers inside and began fingerfucking herself, with her pussy making sloppy sounds since she was dripping wet. The whole time, she was staring right at Sam. She graduated from fingering herself to her clit, which is how she gets herself to orgasm. It didn’t take long, maybe 45 seconds, and she was orgasming, loudly screaming out “oh godddddd” as her whole body shook.

She looked completely spent, out of breath laying there on the couch naked and spread eagle, her pussy dripping on to our couch. Sam was entranced, and he ran his hand up her leg before diving two fingers into her pussy. They easily slid in, and Lauren gasped. He slowly slid his fingers in and out, and said “fuck you are tight.” At this point, I had had enough, and badly needed to fuck her. I walked around the couch, and picked her up in my arms, announcing that it was time for her to get fucked. As I carried her to my bedroom, she looked back at and said “Thanks Sam!” Not shockingly, he was licking his fingers.

We got back to my room and she immediately attacked me, removing my pants and shirt in seconds. She was obviously well past foreplay, so she threw me down on the bed, and was riding my cock immediately. Normally we tried to stay quiet during sex, but that barrier was obviously gone, and Lauren indulged, loudly moaning and calling out my name before screaming out when she came again. That was enough to finish me, and I shot a huge load inside her.

She climbed off me, and obviously looking to show off again, walked out into the hall naked with my cum running down her leg. Sam was nowhere to be seen, with his door closed. Not too hard to figure out what he was doing…

Source: reddit.com/r/gonewildstories/comments/4si4db/my_girlfriend_gets_comfortable_with_my_roommate