Roommate Ch. 03byWhoAmI99©
Chapter 3 - Triple or Nothing
At that point, she had a total of two more weeks at the house. After a few days I ran into her in the hallway outside of my room and she grabbed my attention. She was wearing a towel because she just got out of the shower. She pulled me up against her and kissed me gently. We talked about how fun it had been having her live there, how much she was going to miss us, etc. Then she said that she wanted to play again. I complained that the other two guys were around, but she suggested that we could just play in my room. I agreed, although it seemed pretty risky that the other two guys would realize something was up, but she stuck her head into Larry's room, and soon the three of us were in my room. Sandy had changed into clothes in anticipation and she had an innocent, long sundress on.
Anyways, she got naked quickly again. She masturbated for us, this time choosing to get up on her hands and knees on the table to heat it up a bit. She made out with me very energetically, and then when she lost again she knelt in front of me to give me a blowjob. But, mid way through it, one of the roommates knocked on the door and asked me if I knew where his pan was...
Sandy jumped up and started grabbing her clothes and I heard the door start to open, so I blurted out "no, don't come in!" He paused, then pulled the door shut and walked away without another word. After he left we all laughed nervously and admitted that he must have realized that something was up with the three of us. I had lost my hardon by this point, but Sandy got it going again and sucked me off for another couple of minutes before Larry called time.
We played another couple of rounds until she lost again. She was supposed to have sex with Larry, but again she hesitated... She had just had sex with Larry like a couple of days earlier, so I wasn't sure what the problem was. She asked whether she could double or nothing again. We said that that would be fine by us, but she raised the obvious point- the other two guys would around, and she didn't feel like she could just traipse around the house in panties and hook up with the two of us on the couch and stuff when they were around... We agreed, and I said that we would waive that part, and do our best to make sure the other guys didn't realize what was up. Anyways, Larry and I each lost a couple of hands and ended up naked before she lost again.
As soon as she lost, she acted like that was impossible, and demanded another double or nothing. At first Larry and I refused, but she started touching herself and begging us in a very sexy, sweet voice, and finally we agreed. But, I said that she'd already lost a big bet, and doubling it would be a really big deal... I said that this time she would have to do a dare every day for a week, with no chance to win her way out of it in poker. And, I said that the dares might be more intense. And I said that we would take turns being the darer like last time, and that in addition to whatever we dared her to do, she would need to sleep naked in the bed of the darer each day. I paused and she looked like she was really having a hard time deciding, so I decided to make it worse. AND, she would have to wear something sexy during the day. Maybe not as revealing as before, but still sexy. AND, I added that on the seventh day we would drive up to Baltimore and stay in a hotel for the night, and the whole time we were there, instead of a single dare, that day she would need to do whatever we told her to all day. Wow. That was a lot. I figured she wouldn't possibly accept. I didn't really want her to accept because she could always win and we wouldn't have any fun at all...
Anyways, we dealt the hand, and everybody traded in their cards for new ones. She didn't trade any in. When we flipped them over, she had nothing. Nothing at all, yet she hadn't traded in any cards! She acted like she didn't realize what she'd done, but it was entirely clear that she had intentionally lost. That idea really got me incredibly excited. She enjoyed the prospect of being our sex slave for a week... I guess it made sense.. She was going to be moving back all the way over to the other side of the country in a few days. What did she have to lose? I guess this was a good chance to really go out on a limb and experiment... She pretended to be upset and went off to bed alone.
The next morning Larry, one of the other roommates and I were all sitting around the living room when she came in. She was wearing a fuzzy flannel nightgown and furry slippers. But, the nightgown was very short. I found out later that she had actually sewed it up the night before to shorten it. It covered her ass, but just barely. She walked around for a bit, pretending to be oblivious of the three of us starting at her before she curled up between Larry and I and sprawled her legs across Larry's lap. We all hung out in there for a while until I had to leave to do some errands.
That night we flipped a coin, and decided that it was Larry's night. He said that he was just going to keep her to himself, since the other two guys were home anyways and he led her off to his room. A few times I heard them fucking, and so did the other two guys. They asked me what was up, but I played like I didn't have any idea... They pretty clearly didn't believe me.
Anyways, the next morning she came out wearing a t-shirt. It went down just below her pussy, but you could see the very bottom of her panties sticking out beneath them. All day she was cuddling up with Larry and I whenever she could and sitting on our laps and whatnot. Finally at about 11 I figured that it was time for my dare. I said that I was going to do the same thing Larry did, and I led her in to my room.
As soon as we got in there, I told her that I wanted her to suck and fuck me all night to my heart's content. She obediently lifted her shirt up over her head and pulled her panties down and took a step towards me. She reached down and started rubbing my cock through my jeans while I guided her back over to the bed and pushed her down on her hands and knees on the bed. I moved around in front of her and put my cock in her mouth. She greedily sucked on it, and after a minute I told her to touch her pussy while she did that. She reached down between her legs and started touching herself. As she got heated up she started moaning and wiggling around more, which really got me excited.
Right before I came I pulled out of her mouth and laid down next to her. She laid down too and I guided her hand on to my cock and told her to go very slowly. She did, stimulating me just enough to keep me hard, but not enough to get me off. After a while I started rubbing her tits, then her ass, and finally her pussy while she massaged me. Finally, I pulled her on top of me, straddling me, but facing towards my feet. She slid down on to my cock and started fucking me until I came inside of her and she came herself at about the same time.
We spent the rest of the night cuddling together. Many times I would move her hand or her mouth to my cock, relishing the attention. Sometimes I would have her touch herself. Finally, early in the morning I rolled her over on to her stomach and fucked her from behind. Later, as I had asked her to, she woke me up by sucking on my cock again. Afterwards, she grabbed her t-shirt and panties and headed back to her room.
An hour or so later she was back in the living room all showered up. But, this time, she had apparently decided to go a bit farther... She was wearing just a white sports bra and a medium sized pair of white panties! Both of our other roommates were in the living room, and they both just stared at her speechless... She looked great. She was pretending like there wasn't anything unusual at all about her outfit. She made herself breakfast, flopped down on the other couch, watched TV, etc. She really just played it off like nothing was unusual, so eventually our other roommates started acting normal again...
That night, Larry told her his dare. He wanted to fuck her outside. He said that they were going to go to the beach and find an isolated spot and fuck. I didn't go with, but apparently they went way down past the other people and bonfires and fucked on their blanket. He said it was really exciting. Anyways, eventually they got back home and went right into his room where I could hear them fucking again in the middle of the night. That wasn't required by the rules...
The next morning she was just wearing the flannel night gown again and I wasn't around much during the day anyways. During the day I slipped off to buy her an outfit for that night. After dinner, I gave her the stuff I had bought and explained what I wanted her to do. She was pretty anxious about the idea, but went to get dressed anyways.
When she was done she came back out into the living room, and she looked incredible... She was wearing a fairly short black dress and black high heels. The trick, though, was that the dress was very transparent. Under the dress she had on the bra and panties I had bought. It was a small pair of thong panties, and a fairly sexy bra. Our roommate was once again stunned as we left to grab a cab. The cabbie kept looking Sandy up and down lecherously while she sat in the back. Larry and I each kissed her a little bit on our way over to the club.
When we got there everyone in the club was starting at her. She looked incredible, but she also looked like a total slut... The girls were all shooting her dirty looks, but the guys were all staring lustily. She danced in front of Larry and I sexily, walked around soaking up attention, and was always posing to get the most out of the look.
After a couple of hours, however, she followed the next instruction I had given her. She went in to the bathroom, and when she came back out, her bra was gone! Now this was really something to see. You could very clearly see her breasts though the dress and they looked absolutely great. She strutted around a bit, trying to look sexy rather than nervous, and the audience certainly appreciated her. Later on, she sat on each of our laps and kissed us from time to time until we decided to leave for the night.
But, as soon as we got into the cab she followed her final instruction. She reached up under her dress and slid her panties all the way off and pushed them discretely into her purse. Se looked very tempting, sitting there between Larry and I very nearly naked in this public cab, with the cabdriver checking her out, while we were driving through busy streets.
She alternated between making out with me and making out with Larry, but the whole time each of us was rubbing one of her thighs, letting our hands linger up too high. Finally, we pulled up in front of the house and got out. When she got out, she was standing outside, very nearly naked. I paid the cab driver while he stared at Sandy and we walked inside. When we opened the door, I saw one of our roommates down the hall in the living room. Sandy ran down the hallway to my room, but he must have seen that she wasn't wearing her underwear anymore. When I joined her in my room, I bent her over the arm of the couch, still wearing her dress, and fucked her right there.
The next morning she came directly out of the bathroom after her shower into the living room, so she was still wearing her towel. It was a fairly big towel, so when she sat properly it covered her completely. But, during the course of the next couple of hours it slipped down to reveal her breasts, and possibly her pussy, a couple of times. Our roommates were watching intensely and I doubt that they missed too many of those glimpses.
That afternoon, I was in the kitchen with the roommate that had both seen her coming in the night before, who was also the one to knock on my door while we were playing poker a few nights earlier. He was acting like he had something to say, so I was basically avoiding the topic. But, suddenly he just flat out came out with it and asked what the hell was going on with Larry, Sandy and I. I played dumb at first, but he made a few pretty obvious observations and I couldn't really have totally denied it...So, instead, I just said that both Larry and I had been fooling around with her from time to time. He insinuated that I was talking about a threeway, and I tried to deny it, but he pretty clearly didn't believe it. After we talked a bit, I finally just kind of gave up and admitted that we'd played strip poker a few times, and that when they were gone she kind of played around a bit with hanging out in the living room half naked and stuff... I said that it was kind of fun, but asked him not to say anything. He agreed not to, and said something about how lucky we were...
That night, Larry declared his third and final dare for her. He wanted her to give him a blowjob in the library. But, he added one catch- he wanted her to be completely naked when she did it. She argued that they'd end up getting arrested or something, but between Larry and I we convinced her that it could be done... She begrudgingly agreed, but only if I would agree to come as a lookout. She went off and put on a long, very loose, sundress that went down to her ankles and the three of us headed off to the library.
When we got there, we all looked around for a while to find a good spot. At one point, Larry declared that the spot they were at was good enough and reached over and pulled up the back of her dress to her lower back, giving me a very sexy view of her legs and ass from behind. She let out a little squeal of surprise, but let him start massaging her ass. But, just then, a guy rounded the corner that we hadn't seen coming and Larry dropped her dress and the three of us walked off embarrassed...
Finally, we ended up down in the basement archives area. Hardly anybody every went down there. So, I stood at the corner to keep my eyes open, and Larry told Sandy to take off her dress. She quickly pulled it up over her head and went to kneel in front of him and get this over with. But, he caught her wrist and pulled her up against him standing instead. He kissed her for a while, while squeezing her ass and breasts. Seeing them standing there, him fully dressed, and her entirely naked, in the library was really exciting. After a minute or two, he let her go down on him and pull his dick out. She started sucking it right away, trying to get him off as quickly as possible.
After about 15 minutes, Larry announced that he didn't' think that she'd be able to get him off that way. She stopped and looked kind of unsure about what that meant. But, he just walked around behind her and pulled her hips up to waist height and leaned her forward. He quickly pushed into her pussy from behind. Just about then I heard a quiet sound. I looked over, and realized that I saw part of someone's head through a stack of books. It looked like he was hiding there watching Larry and Sandy. I was about to say something when Larry caught my eye, and pulled his finger up over his lips in the 'shhhh' signal. I almost laughed, but didn't say anything. Larry finished fucking her like that and came inside of her pussy.
Right after he came, the guy hiding behind the shelf quietly started sneaking back to the elevator. Larry pulled Sandy up straight in front of him by the shoulders and held her up against the front of his body. She immediately saw the guy and let out another embarrassed squeal, but Larry held her still while the guy ducked away and into the stairwell. She pulled away from Larry and grabbed her dress, and asked him how long that guy had been there! Larry said that he thought he had been there since they started fucking.
She hit him and acted mad, but I noticed that she hadn't put her dress back on yet despite having been caught. Larry noticed that too and reached out and pulled her dress away from her, leaving her naked again. He took the opportunity to kiss her and run his hands all over her body again, squeezing her ass and tits, and sliding his hand over her pussy. She reacted to his hand on her pussy by squirming against it and letting out a little moan. Satisfied that he'd made his point, he stopped and gave her back her dress, which she quickly pulled on, and we went home.
On the way back to the house she complained a lot at first about how Larry shouldn't have done that, and asked why I didn't tell her and so on. But, she didn't really seem all that mad. Right before we got back, Larry said to her, "oh, come on. You thought it was a turn on, didn't you".
She didn't answer for a while, and then she finally gave a meek admission that it had been hot, and we all ended up laughing.
The next day she was hanging out in the living room when I got out there wearing a little, loose frilly pair of shorts and her white sports bra again. In the afternoon I told her that the roommate had pretty much figured out that something was up, and told her what I had told him. She was really embarrassed at first, but eventually decided that it didn't matter because she'd probably never even see him again after she moved back west in a few days.
I went out later that afternoon to buy something for her to wear that night. When I got back, at about six, I explained to Sandy what my plan was for that night's dare. Basically, I wanted her to make dinner for all four of us, and serve it to us as a French maid. I laid out all the specifics of what happened below, and she really seemed like she might refuse to do it. But, after a bit of persuading, she decided that since she would most likely not see the other two guys again after she moved, and since they'd already basically seen her naked through her see-through dress, she would do it. I gave her the bag of stuff I had picked out that afternoon and went to tell the guys about the dinner plan. I found all three of them and just said that Sandy wanted to make a special dinner for the four of us. They all agreed to be ready at 8.
So, at 8 we all gathered around the dining room table. Sandy had been preparing food in the kitchen wearing normal clothes, but she'd disappeared back in to her room about 20 minutes earlier to get ready while the food cooled off. When she came back she was wearing the French maid's outfit I had bought for her. It included a very short skirt with lots of layers of petticoats that made it flare out almost 45 degrees, but it was very short, and you could see the bottoms of her asscheeks below the hem. It was also very low cut, and had a push up wire that made her chest look great. She was wearing fishnet pantyhose and some high black heels with it as well, which made he legs look terrific. The two roommates were clearly surprised, but they were pretty clearly excited too.. They must have put two and two together and realized that they were going to get to take part in some of the exhibitionism that I'd told them that we had seen...
Anyways, I pretended to be surprised myself, and asked her what the special occasion was. She responded that she'd just had a great time living with all of us, and to give us all a very special dinner was the least she could do and gave a very cute smile. I had told her to pretend that it was entirely her own idea. Somehow that made her seem more exposed to me. She served us drinks and appetizers while we all checked her out, and she flirted with each of us whenever she could.
After the appetizers were done, she asked us all whether we liked her outfit. Of course, we all immediately assured her that we liked it very much. She said something about how she liked to do her part of keep the men of her house happy, with a big smile.
Then she said, "Well, I don't know if you would be interested, but I actually have another outfit I could show you. I think you'll like it even more."
We all heartily agreed, and when she brought out the main course she was wearing a short, loose, transparent white baby doll with a little apron in front. Underneath it she had on a small white thong. She wasn't wearing any stockings anymore. You could see her beautiful breasts clearly through the nightie. She looked amazing, and especially the two other roommates were staring at her displaying herself for us like that in amazement. She giggled as she served us.