The Bet

A horny story i had to share.

“I know, without a doubt, that I can suck cock better than you!” I said to Stephanie. We had been the best of friends since high school, and that hadn’t changed even though we are both married now. We still hang out at least twice a month. Sometimes with our spouses, sometimes not.

“Charley, there ain’t a man alive that can suck a dick better than a woman.” She replied.

“That sounds like a challenge to me.” The bartender sat down another round of beers in front of us with a shocked look on his face. I’m bi-sexual, so nothing embarrasses me, and I continued without missing a beat. “ I bet you $100.00 plus the tab tonight, that I can pleasure a man better than you!”

“You’re on!” Stephanie accepted and shoved me, nearly knocking me off of my stool.

“You Bitch!” I said shoving her back. “We’ve got to be fair now. This bar might be a target rich environment for you, but, we’ve got to go somewhere that I can be guaranteed some action.”

“You pussy! What do we have to do, go to a gay bar?” Stephanie chided. “No. wait a minute. I’ve got it. How about we go to one of those adult bookstores? If you can’t get laid there, you can’t get laid in a morgue!” We both laughed at that one. “Which one?” I asked “Capital or Triangle?”

Stephanie took a quarter out of her pocket. “Heads, it’s capital, Tails, triangle.” The coin flipped into the air, then came down on the bar in between us and rattled and clanked to a stop. Heads it was. So to the capital abs we went, discussing terms and conditions as we went. The rules were quite simple. Give a consensual blowjob, then switch partner for an interview.

We arrived and walked into the theater. We decided it was best to split up. Stephanie went in one theater, and I went into another. In less than ten minutes I glanced up to see Stephanie walking by towards the video booths area with a handsome john in tow. It took me a bit longer, but of course I found myself a willing participant that required little or no convincing. I decided to offer him a blowjob right there in one of the dark corner of the theater. I figured that would add to the excitement. I was right. His soldier was a full attention and throbbing before I could get it out of his pants. He was moaning with pleasure the moment it entered my wet mouth. As always, the taste of pre-cum lit a fire in me, and I gave him what I’m sure was the best oral sex he had ever experienced. I was so absorbed with the task at hand, I didn’t notice Stephanie walking up behind me with her new best friend. But, I did hear her when she gasped and said, “You fuckin’ slut!”

I didn’t miss a lick, and kept slurping on my yummy cocksicle. Having an audience must have really turned it’s owner on too. Because, his legs began to tremble and the first thick, hot shot of cum hit the back of my throat hard. I opened my mouth wide so he could watch as the next few shots splashed onto my tongue, filling my mouth full before heading south for my stomach. “Well cowboy, how was that?” Stephanie asked as she put a hand on his shoulder to steady him. With sweat pouring off of his face, his knees still shaking, and my mouth around his cock head sucking him dry, all he could manage to do was sigh and nod his head. “I came so damn hard!” He finally said.

Still on my knees, I glanced up at Stephanie’s beau. “She sucked, I came, she swallowed. It was a good night.” He smiled down at me knowingly. He apparently already knew what was going on with the bet. But, I suspect, after what he had just witnessed, he wished he could have traded places with my partner. Long story short, there was no winner, or loser. We left the theater satisfied of course, but discussed that there was truly only one way to win fairly. We were going to have to convince one man to fuck the both of us at the same time. So we decided to give it another try in a couple weeks. This time we booked us a nice hotel suite for the night, before going to the ABS to find our man. We went back to capital to see if we could be successful again. We paid our money and went to the back. We bumped into my knee knockin’ buddy from the other week. But, Stephanie said it wouldn’t be fair to use him, since he already had a biased opinion of me. I agreed, but, couldn’t resist, and went to give him a quick round of head anyway. When I came back to find Stephanie, she was leaning against a wall talking to a young athletic looking buck.

“Here she is!” She said as I approached them. I smiled sarcastically and shot Stephanie the bird. I offered the young buck my hand. “I’m Charley.” He took my hand and kissed it instead of shaking it. “Pleasure to meet you Charley. I’m Gregg.”
My heart fluttered, and I may have even blushed. “I hope the pleasure is mine.”

Stephanie tugged at my other hand, pulling me away from Gregg. “Will you excuse us girls for a moment Gregg?” Gregg nodded and leaned back against the wall. “What do you think Charley?”
“He is so…”

“HOTTT!!!” we both said. We must have looked like a couple of school girls, giggling over the senior quarterback. “You haven’t done anything with him yet have you?” I asked.

“No. Not that I haven’t wanted to. But, he’s on board for our little bet if you are ok with him.”

“Do you have to ask?” We both giggle and went back to the wall to join Gregg.

“Alright, I think the deal is almost sealed. Just one more thing.” Stephanie said to Gregg. “Charley wants to see the goods before we leave.” My jaw dropped in shock and I slapped her on the arm. All she did was laugh and looked at Gregg. “Well!!?”

Gregg pulled down his loose fitting gym shorts and took his cock in hand. He was no John Holmes, but he was a good 7 inches limp as a spaghetti noodle. From my experience, that means we’re going to end up with a nice thick 8 inches or more of throbbing love missile. Stephanie and I both walked over and massaged his penis. It felt so good to the touch. The skin on his cock still had the suppleness of youth, but, we knew he was all man. “Are you ready for us, lover boy?” I challenged Gregg.

“Let’s go for it!” he took our hands and led us to the exit and out into the parking lot, where we all piled into my car and headed for the hotel. Once we arrived to the room, Stephanie and I excused ourselves again to get freshened up. We told Gregg to make himself at home, relax, and we promised him a night he would not soon forget. Stephanie and I went into the bathroom together. We peeled out of our clothes and stripped down to nothing but our panties. While Steph touched up her make-up in the mirror, I took measures to prepare myself for anal sex ( I do hope you understand me, and I don’t have to go into detail for that). Steph followed suit, thinking she may be partaking in some anal activities herself. And I touched up my make-up. We took one last look in the mirror together. I couldn’t help but think that Stephanie had an unfair advantage over me with her natural 36 C breast. Mine are natural too, but, they are a mere 35 A/B depending on the bra. Hopefully tonight, it want be about the boobs.

We went back to the bedroom, and found Gregg stripped completely naked and lying back on the bed fondling himself and waiting patiently for our return. We crawled on the bed like a couple of horny cats. We took turns slobbering all over his ever growing manhood. Gregg just laid back and enjoyed all the attention. As I was deep throating his cock on one of my turns he reached down and tweaked my nipples and massaged my small breast. I noticed he did the same to Stephanie. After a bit, while I was still lapping at his cock and balls, Stephanie got up, took off her thong, and straddled Gregg’s chest and put her juicy cunt in his face. Gregg reached around and caressed her ass and pulled her pussy to his mouth. A little jealous at the site of Steph being ate out, but still turned on I continued to suck on Gregg’s cock like a Hover vacuum.

“I’m ready to fuck now ladies!” Gregg called the next play. Stephanie reached over to the nightstand, and rifled around in her purse, came out with a condom and handed it to Gregg. “Put it on with your mouth!” He handed it back. Steph opened the condom, popped it in her mouth, and proceeded to try to put it on with her tongue and lips with no success. After giving her ample opportunity, I asked her to let me give it a try. Frustrated, she gave me the condom, waved her hand over Gregg like he was a buffet, in a gesture for me to be her guest. I placed the condom in my mouth just right, and after two or three deep thrust we were staring at a perfectly wrapped love gun. Gregg hopped up on his knees and took me by the hand and laid me on my back gently. He slowly pulled my thong off of me. I covered my little cock with my hand, not wanting him to be turned off. But, he removed my hand and put my feet on his broad shoulders, spit into his own hand and wet the condom. I closed my eyes as the immense head of his cock pressed against my sphincter. He eased his tool into me, inch after beautiful inch, until I felt the head putting pressure against my anal valves (for those of you that don’t know, that’s the entrance to the colon). He backed out and short stroked a few times. Then as he felt my muscles relax a little he pressed hard and his cock shot past the valves and he was completely inside me. I rocked my hips and grabbed his ass as his thrust got firmer and faster. I loved the feel and the sound of his balls slapping against my ass cheeks each time he thrust deep within me. The room was filled with the sound of our sex. I had nearly forgotten about Stephanie, when Gregg pulled out of me with a pop. Then I notice that Steph was lying beside me rubbing my tits. I smiled at her. Gregg lay down behind her in the spoon position, threw her leg up and stuck his massive rod deep into her wet vagina. I returned the favor and began sucking on Stephanie’s breast while I massaged her clit with my finger. I felt it when she came on his dick and her body began to shudder. Gregg and I held her tightly as her orgasm eased. Gregg looked up at me. “I don’t like condoms, Charley.” he stated.
“I don’t either.” I smiled at him. He pulled out of Staph and took his condom off and cast it on the floor.

“I think the only way I’m going to be able to tell who the best is is to fuck you both bareback in the ass.” We were both a little shocked. But, I was ever so willing. And I couldn’t wait to feel his bare skin inside me. I got on my hands and knees, facing the head board, and put one of the king-sized pillows under my belly. Gregg saddled up behind me and easily pushed his cock back in me. There is absolutely nothing that compares to the feel of skin on skin. I could feel every one of his heartbeats as they pumped bl**d into his weapon. The next thing I felt was Stephanie straddling my back and bringing her ass down and stacking it on top of mine. I’d seen this done in the movies and knew how inviting it was for Gregg with two fine asses presented to him for his pleasure. He bent down and rimmed Staph’s ass with his cock still inside me. It was as much a turn on for me as it was for him. After a moment or two, he pulled out of me and thrust his cock into Stephanie’s asshole. She squirmed a little on top of me, but she soon got used to it. Now that I think of it, she may have been an anal virgin that night. I know Gregg was in ass heaven, because he started going back and forth between us about every third thrust. Each time he entered Steph she would squirm and moan. My ass was gaping and willing to accept him every time he’d put it to me. Then Gregg began to moan himself. “I’m gonna cum! I’m gonna cum! Lay on your backs, both of you!” he panted.

We both did as we were told and as he pulled out of me for the last time, Steph and I lay side by side on our backs with open mouths like two porn bitches begging for a meal of semen. Gregg stood over us, pumping his red hot sausage our faces. All of a sudden cum began to rain out of his cock. As he pumped and shook it at us, cum went everywhere. In our hair, in our mouths, on our tits. I believe he could of possible filled up a gallon milk jug, with all the cum he spewed. When it was over he collapsed on top of us. We were nothing more than a pile of exhausted sweaty flesh. “That was amazing ladies.” Gregg finally said. I couldn’t believe he called us ladies. We had behaved like the exact opposite. Then I fell asl**p. We all did, cuddled up in that king sized bed. When I woke up in the morning, I heard Gregg singing in the shower. I nudged Steph and woke her up, and pointed toward the bathroom with a grin. We got up went in and got in the shower with Gregg. None of us had the energy for another round of sex, but, the hot water felt good to our bodies. It felt really good to touch each other and wash one another. I couldn’t stand it anymore, I just had to know, and I hoped it wouldn’t ruin the mood.

“What’s the verdict, Gregg?”

“Well, let me just say this. That was by far, the best bout of sex I have ever had in my young life. Charley, you’ve got one hell of a talented mouth, and one of the most welcoming asses I have ever had the pleasure of fucking. Steph, you give a good blow too, and you’ve got one sweet tasting pussy. So it’s hard for me to say who was the best. If anything puts one of you over the other it’s simply this……..Charley, you are so willing to do whatever it takes to please me. Sometimes you seemed a little hesitant Stephanie. But, I love you both.”

We finished our shower and said our goodbyes. We dropped Gregg off at his car back at the ABS, and Steph and I headed home to our normal boring life. But, we both were smiling and laughing all the way home. And me all the more, because I think I won.

85% (8/1)
Categories: Hardcore
Posted by ukvoyeur3
3 years ago    Views: 574
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2 years ago

3 years ago
It was a bit all over. When I first started reading it seemed it was a Guy and Lady, then it seemed like 2 women, and near the end it seemed more like a CD/Tranny & a female. Not quite sure which is right, but other then that is was a good read.