Losing the Bet, Being the Wager

For Leanne's birthday, my wife Debra wanted to do a dinner party at our house for Leanne, Sheri, and Jeni. The three women were all my wife's former college roommates from two years ago when they had rented an off campus apartment together for their senior year.

Perhaps I should describe these women for you so you know how lucky I was every time I visited my then fiancé at her apartment.

Starting with my wife Debra... Debra is 5'7 long legs, very nicely curved ass, she has long dark hair all the way to her sweet ass, and firm B sized breast that fit ever so perfectly in my palms, blue eyes and thick luscious lips that were truly 'cock sucking lips' if ever there were any.

Leanne was 5'5 very lean, tight little ass, curly brown hair about shoulder length, pert little A sized breasts, chocolate brown eyes, and small lips that curled into a mischievous grin easily.

Sheri was 5'3 but very athletic, muscular legs, abdomen, and ass. Her hair was red, straight and cut short; she had bright green eyes, B sized breasts that somehow always seemed larger, and a beautiful smile when she chose to, which had never been too often as she was more of the tough no nonsense type.

Jeni was the tallest at 5'9, long blond hair nearly as long as my wife's, she had C sized breasts that she always showed off in cleavage revealing outfits, shapely legs, bright blue eyes, round ass, and a ready smile always on her full lips. My wife admitted back in school that if ever there was girl she wanted it was Jeni.

Safe to say between the four of them you had nearly every type you could want if your interests were female. Also safe to say they were all out of my league, I am only 5'8 myself, medium brown hair that I wore long when they were in college, but I've had to cut short for my life as an 'adult'. I have a medium build and a goofy looking face and smile. Usually I was referred to as nice, or cute, never good-looking. But my wife seemed to find me attractive and who was I to complain.

The girls all showed up together with bottles of wine each and after talking we sat to dinner. After dinner we sat and drank and talked and drank some more. Leanne said she needed to use the bathroom so she went to the downstairs one, and then Sheri asked to go so we told her to go to the one connected to my wife's and my bedroom. Sheri noticeably stumbled going up the stairs but she finally made it up.

After Leanne had been back for several minutes I was beginning to wonder what was taking Sheri so long, I was worried she may have passed out or something. Then she came out of the bathroom and stood at the top of the stairs wearing next to nothing.

" Hey check out my dick!" She yelled.

She was wearing a strap-on I'd given my wife as a gag gift a year before. My wife always would get upset and say, 'suck my dick' and I'd say, 'you don't have one', so I had gotten her one. That was supposed to be in a locked box of toys in our bedroom.

" Sheri! Go get you clothes on and put that back!" I yelled up the stairs a little upset that such a private thing was on display.

" Why don't you make me?!" Sheri said lewdly stoking the purple cock that was the only thing she was wearing.

Figuring I'd had less to drink then her I thought I could probably catch her and get her back into her clothes, so I charged up the stairs. Sheri ran ahead of me giggling as she ran into the master bedroom.

I got to the doorway to see her jumping on the bed with her boobs and purple cock bouncing in front of her. I ran from the door towards the bed and dove to grab her. In a show of athletic ability that stunned me she bound out of the way and as I landed face first on the bed she landed on top of me.

Faster than I could believe possible she handcuffed me to the bed with cuffs she had attached to the headboard, she then reached under me unbuckled my belt, unbuttoned my pants and yanked them and my boxers down and off my body, yanking my shoes and socks with them. Then I felt and heard my shirt being cut and then torn from my body.

Here I was naked handcuffed to my bed by one of my wife's best friends. I tried to squirm free but she grabbed my left foot and cuffed it to the footboard, and then despite my struggles she did the same to my right.

" Damn it David!" I heard my wife's voice from the doorway.

" I didn't do this! She did it! Get me out of these!" I said frantically.

" I can't do that because you just lost our bet." My wife said bringing herself into my view.

" What bet?" I asked without comprehension.

" I was saying I could get any guy in bed and naked." Sheri starts.

" But then thinking of what a great guy you are, I bet she couldn't get you to."

" And I bet against her."

" I'm not willing to this." I said indignantly. " I would never cheat on my wife."

" Well to be fair nothing in our bet said you had to be willing. She got you in bed and naked and that means she wins." Debra says.

" Well what did you bet?" I ask, wondering how much money we would be out for this little bet.

" You." Leanne says with a smile.

" What do you mean?"

" That I get to have you however I want you." Sheri says with a smile.

" What?!" I ask in disbelief.

" That was the deal." My wife agreed. " Try not to break him, oh and be good to Leanne to, it is her birthday."

Leanne slowly started to strip out of her clothes and I could feel my cock get hard against the sheets.

" What are you going to do to me?" I ask.

" Something I've always wanted to try with a guy." Sheri said cryptically. " For now why don't you use the tongue Debra has told us so much about on Leanne, after all she is the birthday girl."

Leanne climbed on the bed in front of me and lowered her pussy down in front of my face. I take one last glance at my wife to see Jeni's hand on one breast, and one hand lifting up my wife's skirt. I tentatively reach my tongue out and caress Leanne's outer lips.

As I begin to let my tongue slide around another woman besides my wife's pussy for the first time since we had first begun dating I feel Sheri's lips kissing my ass cheeks. I slide my tongue along Leanne's inner folds as I feel Sheri's tongue trace the crack of my ass. Sheri's tongue inches close to my anus and then back up as my tongue circle's Leanne's hole. Then as I feel Sheri's tongue slide right over my anus I shiver and let out a surprised gasp.

" I think he liked that!" Leanne says excitedly.

" Then he'll love this." Sheri says.

Suddenly I feel her tongue push against by anus and force its way into me. I buck back into her with a need I had never felt before.

" Don't forget about me." Leanne says with a smile, and a gentle hand drawing my mouth back to her pussy.

Needing no further urging I delve my tongue back within her folds as I enjoy this new sensation of having my ass tongued. In time with Sheri's tongue fucking my ass I begin to flick my tongue across Leanne's clit. Before long my moaning into her pussy is out done by her screams of orgasm as she pulls my head hard against her and she bucks her hips in to my face.

" God he sounds good, I am going to have to try that later, but now..." Sheri says.

Sheri moves around behind me a bit before I feel something cool pour down my ass crack. Then I feel Sheri's hand massaging the oil down my ass and then her finger teasing my anus.

I continue lapping lightly at Leanne's sweet pussy as Sheri pushes her finger into my ass. I slowly lower my tongue so that I am tracing the path between Leanne's pussy and her anus. Leanne lifts her hips up to allow my tongue further access to her rear, and when Sheri adds a second finger to my ass I push my tongue into Leanne's.

Leanne starts grinding herself against my nose as my tongue works her ass, and Sheri's two fingers work my ass as I buck back into them.

Suddenly Sheri pulls her fingers out and Leanne lifts way from my face for a moment. Then Leanne slides beneath me and places the head of my cock at the entrance to her pussy. I glance again over at my wife and my cock seems to harden more as I see her in a sixty-nine position with Jeni.

My attention is re-drawn to my position as I feel something larger than a finger press against my anus. It suddenly dawned on me what was going to happen.

" Please don't." I whisper, " I'm a virgin back there."

" Well you've taken pretty well to it so far." Sheri says whispering in my ear. " I'll be gentle, you just relax and enjoy."

Suddenly I feel her pushing forward and I try to force myself to relax. Then without warning the head pops into my ass, and this forces my cock to bury itself halfway into Leanne's pussy. Leanne and Sheri both moan in unison, as I am half caught between the pain in my ass and the pleasure in my cock.

After a moment's pause Sheri begins pushing forward, which at first only succeeds in pushing my cock deeper into Leanne's pussy.

" God you are fucking huge!" Leanne exclaims with a gasp.

When I finally bottom out Leanne lets out another low moan. Now with nowhere further for me to go, Sheri begins to continue the penetration of my ass. The pain had subsided and I just relaxed allowing myself to just take it for Sheri's pleasure until just as I feel her pressing against me I feel a twinge in my ass that sends a pure pulse of pleasure right through my cock.

" Your hot ass just ate my entire cock in one try." Sheri says in a low sensual voice right at my ear as I feel her breasts pushed against my back. " How does it feel?"

For moment I nod my head, " Feels good." I admit quietly.

Sheri slowly pulls out and I just stay buried in Leanne unable to move. Then as Sheri pushes back forward I push back to meet her.

" You fucking love it don't you?" Sheri asks.

" I do." I admit.

" I want to do this to you until we both cum." Sheri says quietly.

As Sheri pulls back again I push forward into Leanne's pussy and she gasps deeply as I penetrate her. " God, you two are so fucking hot!" Leanne says excitedly. I could feel her pussy convulsing around my cock.

I begin to pull out and Sheri pushes back into me causing both of us to moan together. Then I push forward and Leanne moans a little louder. Her tight pussy was squeezing my cock tighter than I could believe, it was like she was on a continuous orgasm. I slowly push back into Sheri and we both moan again forcing my cock to twitch in Leanne's pussy.

" Tell me what you want ass slut." Sheri whispers in my ear.

" Please fuck my ass." I beg knowing how she wanted me to respond.

" Louder bitch, I want your wife to hear."

" Please fuck my ass!" I say louder.

Suddenly I hear Debra screaming her orgasm into Jeni's mouth and pussy. Slowly Leanne, Sheri, and I begin increasing our pace with me rocking between them. One moment I am filled with Sheri's rubber cock, the next I am filling Leanne with my fleshy one. I rock back and forth between them, each of them meeting me thrust for thrust and all of us rushing towards orgasm.

Suddenly Leanne lets out an ear shattering scream and starts thrashing about on the bed beneath me. Her spasming pussy walls clench my cock tightly so that my cum boils from my balls, and travels up my cock. I bury myself deep into Leanne's pussy and yell my orgasm as my seed bursts out of me deep into Leanne. As my cock is shooting its first spurt Sheri forces herself down deep inside me and lets out a scream of orgasm as she rocks her body up and down against my ass with the rubber cock buried deep inside me. Almost unnoticed I hear two more excited moans as both Jeni and my wife cum into each others mouths spurred on by the three of us on the bed.

For several minutes we lay there spent, with my cock buried in Leanne, and the strap-on buried in me. Then my wife and Jeni crawl on the bed with the three of us and Sheri slowly pulls out of my ass. Jeni, Debra, and Sheri uncuff me and I pull out of Leanne. The five of us crash together on the bed in exhausted sleep.

Good thing my wife and I got the king size bed instead of the queen we had been thinking of at the store. I only hoped we wouldn't wake-up with hangovers and regrets, but hey, that was one hell of night we would never forget. Of that I was sure as I drifted off to happy sleep with four naked beautiful women surrounding me.