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The Bet

It began with a simple bet between my fiance, Cat, and Melissa, a friend Cat met at the massage therapy school she is currently attending. Melissa is a 5'5" voluptuous young woman with dark red hair with a few extra pounds. She also happens to be bisexual, as is Cat. While working together in class, each found out that the other was bi, and there was a mutual attraction.

Melissa was not seeing anyone at the time. She lived close by and would often hang out at our place, or pick Cat up from work when I was working. I have known Cat was bi from the time I met her, and I was fine with it and encouraged her to explore that side of herself.

Cat told Melissa that I was multi-orgasmic. Melissa did not believe her. So one night the three of us were sitting on the couch at our apartment. The conversation turned to sex and Melissa said that she wanted to see for herself that I was multi-orgasmic. Both Cat and I were up for that, so Cat showed her. As I was slowly regaining consciousness, Cat and Melissa made a bet. Cat was open to watching Melissa and I play together some. If I came first, Melissa would get to have her wicked way with Cat. If Melissa came first, Cat would get to have her wicked way with Melissa.

Once I regained consciousness, I was told of the bet and the stakes. I grinned and said OK. Now Melissa said one of the conditions was that I could not do just oral or fingering. I had to do some intercourse, kissing, oral and fingering. As Melissa put it, "I have heard from Cat how talented you are." I looked at Cat to see if this was OK. The look she gave me was one of "You know how much I love to watch you work, and how turned on it gets me". The only thing she said to me was DO NOT CUM FIRST!

Melissa and I looked at each other and laughed and nodded. As I moved over to Melissa I quietly told Cat when Melissa was not looking to go get the toys and supplies. Cat nodded and said, "First, I want to see you two kiss." I gently pulled Melissa’s palm to my lips and began to softly kiss her palm. Then I ran my tongue over her index finger. Melissa closed her eyes and shuddered. When she opened her eyes, the look she had said “What did I get myself into?” I began to kiss her neck and lick her earlobes. She began to shudder and softly moan. I moved so that I could kiss the back of her neck which reaching around and cupping her breasts with my hands. I began to fondle and squeeze her nipples through her shirt. I lowered my hands and pulled her shirt over her head. Melissa was wearing a black see-through bra. She turned around so she could wrap her arms around me and pull me closer to her. We kissed deeply and passionately. I began to work my way down to her breast. Melissa took off her bra. I played with one breast while running my tongue over her other nipple. While running my tongue over her nipple, I moved my hand down to her jeans and began to unbutton and unzip them. Melissa tossed her pants down to reveal a black thong. Melissa stepped out of her thong and positioned herself so that we could do a 69. I lowered myself down on the couch and began to give her some serious oral attention while she began to do the same to me. I began to feel her coming close to having an orgasm, so I slid out from under her and entered her now extremely wet pussy doggy-style. I began to fuck her slowly as she also rocked back and forth.

I began to play with her ass, and slowly and gently inserted a finger into her ass. She squirmed with delight. She began to rock back and forth, faster and faster, moaning. Finally unable to stand it any longer, she came in an intense and loud orgasm. While she was recovering, Cat went into the bedroom and got out the toys. When she came out, Cat told Melissa that she was at her mercy, and rolled her over to show her that I was still erect and ready to go. Melissa just shook her head in disbelief that she had lost the bet with Cat.

Cat began to have her wicked way with Melissa by simply kissing the top of her head while running her fingers through Melissa’s fine hair. She slowly worked her way down to Melissa’s mouth, and kissed her deeply while holding Melissa’s head between her hands.

She then ran her tongue gently over Melissa’s Adam’s apple and throat, back to her earlobes. Next, she ran her fingertips over Melissa’s skin until they reached Melissa’s breasts. She played with Melissa’s right breast for a while, squeezing the breast and then squeezing the nipple. Slowly, she moved her mouth over Melissa’s left breast and began to suck on it. Melissa moaned softly and wrapped her hands around Cat’s head, pressing her closer. Cat’s right hand moved its way down to Melissa’s soaked pussy, and she inserted two fingers and began to slowly finger her. Melissa by this point is moaning and breathing heavily. Melissa places her hands on Cat’s head and tries to push it down to her pussy.

Cat obliges, and begins to lick her clitoris while continuing to finger-fuck Melissa to an orgasm. While Melissa is trying to get her breathing back to normal, Cat puts on the strap-on and asks me “Which one?” I pick out a thick purple dildo and pass you a condom. You also select a thin vibrator and lube it up as well.

Gently, Cat kisses Melissa and asks, “Are you still alive? Because I am just getting warmed up!” She gently inserts two fingers into Melissa’s pussy to make sure that she is still wet and ready. Melissa moans as Cat begins to fuck her slowly. Cat kisses Melissa deeply on the lips as she continues thrusting slowly. She holds Melissa’s right breast with her right hand and begins sucking on her nipple while increasing the tempo. Melissa now has her legs wrapped tightly around Cat’s lower back, and her arms are wrapped around her upper back. She is alternating between sucking Cat’s earlobe and telling her to fuck her harder and faster. Cat moves her mouth away from her breast and begins fucking Melissa as fast as she can. She bends her head down in concentration and watches Melissa’s voluptuous breasts vigorously bouncing up and down in time to the rhythm. Melissa starts to breathe fast and squeeze Cat hard as an intense orgasm overtakes her. Cat slows down and stops. She grins at Melissa and says, “Now for the fun part!” She rolls Melissa over and begins to fuck her doggy-style. Meanwhile, she takes the lube and starts to massage Melissa’s ass. Seeing her do this, I place a condom on the vibrator and hand it to her. Gently, Cat begins to insert the vibrator into Melissa’s ass. Melissa moans very loudly and begins to rock back and forth very fast. Once the vibrator is halfway in, Cat turns it on. Melissa gasps and moans and begins to rock back and forth extremely fast, at an almost uncomfortable pace. Cat begins to feel both Melissa’s ass and pussy clench in an extremely intense orgasm, as Melissa moans loudly and nearly hyperventilates. As she starts to come down from her intense orgasm, her body relaxes as she passes out.

Cat looks over at me and asks, “So, what do you think?” I reply, “That was the hottest and most sensual thing I have ever seen!” Cat comes over to me and we cuddle. She is sweating from her exertions, and still breathing heavily. After a few minutes, Melissa regains consciousness and looks up at us. “That was the best fun I have ever had, and thank you both very much!”, she says. All of us sit and chat while the girls recover. Melissa says that was only the second time she has been fucked with a strap-on, and was by far the best. Melissa asks, “How did you get so good at fucking with a strap-on?” I reply, “By fucking me as often as she can.” Melissa’s eyes open wide in surprise that I enjoy getting fucked by a strap-on. Melissa asks us if we have ever done double penetration on another woman, and we say no. Melissa says that is the one thing she wants to try, and she would be willing to try it with us. Cat looks and me and says it is OK with her. She puts the strap-on back on. Melissa gets on top of her as she lies back on the couch. As Melissa begins to ride Cat and kiss her at the same time, I begin to lube up her ass again. I place a condom on myself, enter her, and begin to slowly and gently thrust, taking care not to hurt her. Once Melissa nods her head that she is OK, I begin to thrust faster.

Cat’s hands are wrapped around Melissa’s back. I reach up and place my hands over them, and gently squeeze them. I can feel the strap-on as it moves in Melissa’s pussy. Melissa begins to moan uncontrollably, and moves faster and faster. I can feel her muscles contract tighter and tighter in the most intense orgasm we have seen yet. Unable to hold back any longer, I cum also. All of us collapse and hold each other. Melissa says that will be the last time she loses a bet to Cat, and the next time she gets to have her wicked way with both of us.

End of Story