Roommate Ch. 02

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Ariel increases the stakes.
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Part 2 of the 5 part series

Updated 10/20/2022
Created 01/06/2005
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WhoAmI99
WhoAmI99
145 Followers

Chapter 2: Double or Nothing

We asked if she wanted to keep playing, and she said that of course she did. This time, we told her that she would need to have sex with the winner. She looked a bit taken aback by the escalation, but agreed. As we played, both Larry and I lost our boxers. Both of us had raging hard-ons at the prospect of fucking this beautiful naked woman.

Sandy lost the next hand and looked scared out of her wits. Larry had won, and was just about to burst with anticipation. She started to stand up and then sat back down and looked distraught... After she hesitated for another minute, I asked her what was up. She blurted out that she didn't know if she could really go through with it... Larry objected that it was a little late for that, and she apologized. After a minute she said, "ok, well how about double or nothing?"

We asked her what she meant, and she said, "Well, it's just the three of us all this week. How about if I lose, I agree to spend all week hanging out wearing sexy outfits for you guys?"

Larry immediately exclaimed that that wasn't nearly equal to the sex he was owed, let alone double. They argued back and forth a bit, and finally I offered a compromise. In addition to what she offered, each night we would play a single hand of poker with her one on one. If she lost, she would have to complete a dare, but if she won, she wouldn't have to do anything.

She asked what kind of dares I was talking about, and whined that she didn't think she could have sex with either of us. I said that that was ok, but said that they would be things like, for example, giving one of us a blowjob, or maybe going out with us wearing a sexy outfit. She contemplated for a while, but then agreed. I asked Larry if he was ok with that. He looked grumpy, but ultimately gave in. So, we played one more hand, and Sandy lost again. She looked very much perturbed, but said, "fine. We start tomorrow." And marched off to bed.

The next morning, she came in to the living room wearing a sexy little white nightie with fuzzy trim, a little pair of white panties, and a pair of white high heels. You could see her breasts clearly through the nightie, and she looked great. We spent all day ogling her, and she was clearly enjoying the attention. Finally, after dinner, I pulled out the deck of cards and said it was time for the poker hand. We played, and she lost, and asked what her challenge was.

I said that I would start her off easy. I went into her room and rummaged through her closet. I picked out a very short silky dark dress and a very high pair of heels and brought it back out. I handed it to her and told her that we would be going out, and that she was to wear only the stuff I was handing her. She complained, but ultimately headed into her room to change. When she came back out, she had done up her make-up to the max, and looked stunning. The silky material of the dress clung to every inch of her body. Her ass and tits looked amazing, and it was obvious that she wasn't wearing any bra. It covered her ass, but was extremely short, so she was moving very carefully to avoid giving away any glimpses of her pussy. She looked nervous, but there was a glimmer of excitement in her eyes too as we headed out to the club.

At the club, she was drawing lots of attention, but played it off by sticking close to Larry and I. She sat on each of our laps for a while, and danced in front of us for a while. She looked incredible... I wanted to fuck her so badly. Finally, as the night drew to an end, we went home. At home, she grabbed each of us in the hallway and made out with us, one after another. Each of us let our hands wander down to her ass briefly, but then she went into her bedroom and said goodnight.

The next day she was wearing a short, midriff revealing, t-shirt and a sexy little pair of white panties all day driving us crazy. That night, she won the poker game and we all just rented a movie. She sprawled out across the two of us during the movie, with her head on my chest and her legs draped across Larry's lap. Larry was running his hands up and down her legs and thighs and I was running my hands over her stomach. She was clearly wiggling around to encourage us, but when the movie was over she jumped up and went off to bed.

On the third day she wore a proper outfit. It was a very short skirt and a very small, tight, halter top. She told us that she wasn't wearing anything underneath. She flirted with both of us all day, but nothing exciting came of it. That night, however, she lost the poker game. This time it was Larry's turn to come up with the dare.

He told her to strip and get up on the coffee table on her hands and knees. She complied, and then he told her to get herself off while we watched. As she worked on her pussy she got more and more excited, writhing around more and more and moaning louder and louder, until finally she came right in front of us. It was probably the most excited I had seen her, and was definitely the most excited I had been.

When she was done, she came over to the two of us and cuddled up between us still naked. We started running our hands over her naked body, but as Larry got close to her pussy she stopped him, reminding him that she had already completed her duties for the night. The three of us cuddled there for another half hour, both of us rubbing every inch of her body except her pussy and tits while she wiggled around. I was so horny that I was having a hard time keeping my hands out of the illegal areas, but eventually she leapt up and went off to her room.

On the fourth day she was wearing a bikini. She looked great in it. At one point she sat on my lap and let me run my hands over the exposed parts of her body. He ass looked incredibly tempting in the string bikini bottom. Judging by her nipples, and the slightly damp front of her bottoms, I think she was getting very much aroused by our games. That night, she lost again, and it was my turn to give her a dare.

I ordered a pizza and instructed her that she was going to meet the pizza man at the door wearing only her bikini bottoms. She argued with me at first, but when the doorbell rang she got up and untied her top and headed for the door. The pizza guy was speechless as she handed him the money and took the pizza. After she closed the door she came back in and sat on Larry's lap while we ate the pizza. Afterwards, she went off to her room to read and go to sleep.

On the fifth day, she was wearing a small, tight, white tube top and a small pair of white panties. She looked good enough to eat, and I had a hard time not grabbing her all day... Finally it was time for the poker game, but she won and we ended up just hanging out drinking. Before she went to bed she climbed up on each of our laps, straddling us, and made out for a bit. She let each of us rub her ass and her tits before she pulled away and went to bed.

On the sixth day, she got all dressed up. She was wearing a tiny bikini top, a tight, tiny skirt, thigh high fishnet stockings, and a very high pair of heels. She told us right off that she wasn't wearing anything underneath. All day she made a point of bending over facing away from us and whatnot to give us quick glances up her skirt and whatnot. Her slutty outfit seemed to be having some impact of her behavior that day. Anyways, that night she lost the game and it was Larry's turn to come up with the dare.

Larry had her stand right in front of us and strip off her skirt and top, leaving her standing there naked except for her stockings. Then he had her touch herself for a minute until she started getting excited. Then he had her lay down, face down, across both of our laps with her face in his lap. He told her to pull out his cock and suck him off. She did that, and while she was, I started running my hands over her ass and underneath her tits. As he got close to cumming I started to slide my hands between her legs and started rubbing her clit. She spread her legs and lifted herself up to give me better access, moaning around his cock. After a few minutes, she pulled off of him and he came on his stomach. She handed him a Kleenex and while he was cleaning himself up she stood up. He grabbed her hips and turned her around and laid her down again so that her face was over my cock this time. She immediately pulled me out of my pants and started sucking me off while Larry started in on her pussy. It felt amazing, and as she got more aroused by Larry's hand, I got closer as well. Finally, she came, her whole body thrashing around, and that triggered me to cum right in her mouth. She swallowed my cum as her orgasm played out. Afterwards, she slid off of us and slinked off to bed.

On the last day of our deal, Larry and I got up first. We were sitting in the living room watching TV when she came in wearing only a small red pair of panties. She immediately sprawled across our laps and cuddled up with us while we watched the game. She let us run our hands over any part of her body except her pussy while we watched, so we spent the next two hours molesting her ass, thighs, legs, stomach, back, and chest while we watched. She wiggled around encouragingly, and would periodically switch position to give us a different angle, but whenever we got too close to her pussy she would push the offending hand away. Despite that, all the touching was clearly getting her hornier and hornier.

At about 4pm I proposed we play poker early, since it was the final night, and she agreed. We played, and she lost. I told her that her assignment for the rest of the day was going to be to take off her panties, and spend all day cuddling up with us and letting us touch her however we pleased. I told her that anything beyond that was entirely at her discretion, but that she was not allowed to get herself off.

She promptly stood up and slid her panties down and stepped out of them. I laid her across our laps facing up, and Larry and I started molesting her. He was working on her breasts while I rubbed her pussy. She was writhing around under our attention, but when she sounded like she was getting close to orgasm I slowed it way down and kept her from going over the edge. Larry laughed, and I told him that I didn't want her to cum unless the two of us were coming with her, and he agreed. I kept her on the edge for another ten minutes, before stopping. For the next few hours, we kept moving her around, positioning her in different ways so that we could explore different parts.

By two in the morning we had brought her to the brink of orgasm several times, and she finally yelled out that she HAD to cum or she'd freak out. I reminded her of my rule. She had been cuddled up between us and she turned over so her mouth was above my cock again. She pulled it out and started sucking on me while Larry rubbed her pussy again. She squirmed around excitedly, pushing against his hand. She got closer to an orgasm and he slowed down again. She let out a frustrated noise around my cock. A minute later, I was on the edge of cumming in her mouth when she pulled away laughing that two can play this game! She jumped up and turned around so that she could take Larry's cock into her mouth. I started teasing her pussy, but didn't bring her to orgasm either. Larry held on for a long time. It was almost like a competition at this point.

Finally, she pulled off of him and complained that she needed to cum! Then she said, "God! How hard is it to get a good fuck here?"

I asked "really?" and she let out an affirmative grunt and went back to working on Larry's cock with her mouth. I slid out from underneath her and she lifted up on her knees, leaving her pussy suspended up in the air looking inviting.

I moved around behind her and slid my dick easily into her pussy. She responded with a loud moan of pleasure and relief, and pushed back hard against me. I fucked her doggy style like that while she sucked on Larry. She came almost right away, but sounded like she wanted more. When I came and slid out of her pussy, she immediately turned around and Larry took over fucking her while she suckled on my flaccid cock. Finally she came again and soon afterwards he shot his load inside of her and collapsed on our laps breathing heavily.

After a few minutes she said "God... what am I doing!?" and ran off to her bedroom. On her way she yelled back that the bet was done!

WhoAmI99
WhoAmI99
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