Everybody Wins

There I was, a 35 year old 'Mrs. Robinson' sitting amidst a table full of young 20-somethings. They were all men, except for the friend who had invited me, Tabitha. We had been invited to join their table at Ernie's Pub. So, far off into the corner we trotted with our drinks.

The conversations were plentiful though uninteresting. At one end of the table, a couple of guys discussed calling their 'girls' and heading home for the night. Tabitha and CJ were sort of arguing because they both have significant others, yet find each other extremely attractive. Then across from me I hear Jay say, "Most guys who brag about their penis size really don't have it." My ears perked up. Billy, also across the table from me replies, "I got the size, man! You know it. You've seen me!"

Not being able to resist, and wanting to jump into a conversation somewhere, I quip, "Billy must not have it then... otherwise he wouldn't be bragging." I have a grin on my face.

"Oh, he has it!" exclaims Jay. "He's got at least 14 inches! Don't ask how I know. I've seen it, but don't ask!"

"My curiosity is piqued now, Jay. I want to know how you know." I smiled, not willing to let this conversation die and daring him with my voice to tell me how he knew.

"We were with the same girl at a party one night. I saw his, and he saw mine." Jay blurts this out with an almost shame about it. His cheeks pinking up from embarrassment, I'm figuring this wasn't the most 'tasteful' of encounters. I'm touched that Jay has the sensitivity about him to realize that a woman wouldn't want to hear the details of such an interlude.

I've been watching Jay since I came into the bar. He is clearly the biggest of the bunch, being both tall and of substantial girth. He has the build of a college football player, with broad shoulders and a tiny ass. His tummy is a bit on the tubby side, but in a very acceptable way. Sandy brown hair and blue eyes, he is easily the most appealing to me. And now, seeing this sensitive side of him, he takes on an even more teddy-bearish nature. I just want to hug this guy. To feel my face against his shoulders, my breasts crushed against his chest is the fantasy that's been creeping through my mind since we had joined this table of young men.

Turning back to the conversation at hand, the question of Billy's cock size had me observing the bulges in both his and Jay's jeans. I could tell that Billy was larger than average, but was he the 14 inches that was being claimed? I doubted that highly. Jay wasn't as large as Billy, but I guessed he was about average. I hoped he was at least 7 inches. Oh my! Was I contemplating actually finding out about Jay's dick, too? I knew I had to see Billy's. I had to verify or disprove his exaggerated claims of being 14 inches. But, I wanted to experience Jay's manhood in a much different and more personal manner.

"How would we measure, anyway?" Billy asked. "We don't have a ruler."

"A yard stick is more like it!" Jay bragged on Billy's behalf.

"Let's bet our next paychecks, April. If his rod is at least 14 inches, I win yours. If it's not, I lose and you can have my entire paycheck." This is the bet that issues forth from Jay's mouth. I'm not usually much of a gambler, but I was certain that this was an utter impossibility.

"Ok, Jay. You have a bet!" I bravely say, and reach across the table to shake on it. Jay takes my hand in his. We shake, making the wager official. I notice how large and rough his hand is against my much more diminutive and soft one. As we release our grip, he trails his fingers across the palm of my hand, and his eyes lock with mine for an instant, causing a jolt of sexual energy to spring through my body. It goes straight to my pussy. God, I so want to get to know this guy better!

"I have a solution," I replied, shaking off the tension that's now building in my loins. "Dollar bills are approximately 6 inches. If we lay two of them end to end against Billy's cock, we can tell if it's over or under 12 inches."

Out comes Jay's wallet and two bills. Laid end to end, they portrayed a length that was obviously super human. Seeing that length actually stretched out on the pub's varnished table, caused Jay to waver a bit on his previous statements.

"Well, he's at least 12 inches," says Jay. "Can I amend my bet to be 12 inches instead of 14?"

"Sure," I offer generously. "Those bills laid out there on the table have reminded me just how unlikely it is that he's actually that great in size."

Billy has remained mysteriously silent up to this point of the wagering. "How am I supposed to get it up to measure it?" he says. "It's not 14 inches in it's current state!"

"Hey,everyone," I begin as I rise from the table, not ignoring Billy, but rather contemplating this dilemma. "You guys want to continue this party at my house?"

Billy and Jay's eyes widen a bit, realizing that we'll soon be somewhere private enough to settle this bet. I'll bet Jay is squirming in his Levi's. He knows he's lost his paycheck! It's not that I'd hold him to that wager or anything. I mean, it's his livelihood. I couldn't deprive a man of that. I just wanted to be right. Or to be wrong and see the biggest piece of meat I'd ever had the opportunity to lay my eyes on.

"Tabitha and I are going to head over to my place," said CJ. I could see Tabitha was three sheets to the wind. She'd need a ride, and CJ would be there for her. If nothing else ever developed, CJ would always be there for her as a friend. I wasn't worried about her. I was sorry she wouldn't be there to witness the gigantic cock Billy claimed to be in possession of, though.

"Ok, sounds like a good idea, CJ," I said. "You guys going to come?" I directed my question to the other end of the table this time.

"I think we're heading home to our girlfriends," said Donnie, the more outgoing of the two men.

"Well, looks like it's just us three!" I declared to Billy and Jay. "Are you guys still game for a little more partying?" I saw no need to expose our bet to the rest of the group, but I knew Billy and Jay were aware that we would be settling that wager one way or another tonight.

"Yeah! Let's go!" Billy eagerly chirped. "I'll go pull the car around." And with that, he left the table.

Jay and I stood, and walked toward the exit. His hand reached for the middle of my back, to help me around the corner. Again, his touch sent a sexual shiver through me that ended up residing in my groin. And what's more, I could tell how wet I was growing. My pussy lips were sliding happily against one another due to the juices that had been collecting there. I loved that feeling. I don't know if it was Jay's hand resting gently on my back, or all this talk about 14 inch cocks that had me going so. I guessed it was the former, because I am not that interested in having a 14 inch cock thrust into me to it's length. I mean, it's intriguing in a 'Guinness Book' sort of way. But that's about it.

I see Billy pulling in front of the door in his midnight blue Dodge Ram, and I realize that there is no back seat. Jay opens the door and urges me to step up. "I'll give you a boost," he offers. I can feel his hands on me again, strong hands. He places one hand beneath my arm pit, letting his fingers graze my breast. His other hand is square in the middle of my ass. "Oof!" I grunt as I step up into this monster of a truck. It's not an easy feat for someone with only 5' 7" to her advantage.

I scoot over to the middle of the seat, close to Billy, but not touching him. He places one hand on my knee. "Don't worry, sweetheart," he begins, "I don't bite." His hand slowly slides up my leg, toward my crotch. As much as I despise this unwanted touch, I find my pussy tingling like crazy as he nears it. "I wonder what... "

My thoughts were interrupted by Jay sliding effortlessly onto the seat next to me. He was easily 6'2" and had no trouble pulling his body up into the cab of this truck. He was so close to me. I couldn't tell if he was sitting so close because he had to, for lack of space, or because he wanted to. With nowhere for his left arm to go, he lifted it over my head and rested it on the back of the seat. His thigh was pressed against me, the heat of which was immensely arousing.

Jay's leg began jiggling furiously. "He's nervous," I thought. My mind went back to one small bit of our conversation from earlier. "We were with the same girl at a party one night," was the line that was haunting me now. I wondered if this is what these two were thinking. I am 35 years old! I can't get myself into some sort of an orgy or threesome with a couple of 20 year olds! I wonder if that's why Jay is so fidgety. I wonder if he is anticipating another rendezvous like he and Billy had shared at least once before. I wonder....

"Let's get going, Billy," said Jay. With that, Billy ran his hand a little higher up my leg, to the place where they joined. I could feel his fingers pressing my pussy through my damp panties. Then he removed his hand and put the car into gear. The squealing of the tires was as much evidence of Billy's recklessness as it was the great power of this vehicle. I was growing a bit apprehensive about the ride to my house. Would I even make it alive? I think Jay could read my mind, as he moved his hand from the seat behind me and placed it on my shoulder, pulling me into him. It was as if to say, "I won't let anything happen to you." I was grateful for Jay's reassurance, but did it extend to the evening ahead, or just the car ride? That remained to be seen.

What felt like hours later, but was in reality only minutes, we were pulling up in front of my apartment. Billy parked the truck without ceremony, and hopped out. Jay opened the car door and climbed out. He reached up for me, holding me by the arm as I descended. How I loved his protective nature. I didn't care if Billy was the one with the 14 inch penis, Jay was the winner here. Of this, I was sure. I now just wanted to get the settling of the bet over with, and get on with the evening... drinking, and hopefully getting the chance to at least taste Jay's lips... feel the warmth of his tongue inside my mouth, pressing up against my own soft, wet tongue. As I imagined that 'first', I could feel a deluge release from my pussy. I could feel the tingling begin again, telling me that I was ready to be touched and made love to.

Into my apartment, we went. First me, then Jay, and finally Billy. Once again, I felt Jay's hand on my back, guiding me through the doorway. I couldn't tell if it was accidental, or if it was a calculated move, but Jay's hand slipped down just a hair, to my waistband, just above my ass. As he withdrew his hand, he brushed against my bottom. As I said, I wasn't sure if it was on purpose, or just a mistake on Jay's part. I paused for the slightest moment to regain my composure. I drew in a shaky breath, and continued through the entrance to my humble living room.

"Make yourselves comfortable, guys," I call, heading toward the kitchen. "I've got three ice cold ones coming right up."

As I made my way to the kitchen, the living room became eerily quiet. It was the kind of hush where you just know someone is talking about you. People have long since had that sort of intuition. I guess I expected them to talk about the bet, maybe share their fears about Billy's ability to hold up his end of the bet, and produce an erect 14 inch... wait, amendment.... 12 inch cock. However, I got the distinct impression that this conversation was more about me, than the bet. How I wished I could hear even a morsel of what they were saying! "Dammit!" I cried as I stubbed my toe on the corner of the refrigerator. My mind was lost in what they might be saying... thinking... planning... for our evening.

I quickly retrieved three bottles of my favorite beer, and returned to the living room. The looks on the faces of those two confirmed what I already knew. Billy looked like the cat that had swallowed the canary. A secret was hidden behind the smirk that was being displayed for me. Jay's I couldn't read as well. It was tense, for sure. But what else was it? I tried to shake off the feeling that was creeping into my belly... the feeling that something very unusual was going to happen tonight.

"Here," I said as I offered Billy a beer. "I'll set yours here, Jay." I set his bottle on the coffee table in front of him.

Billy had chosen the chair at the end of the table and Jay, the couch. I plopped down on the couch next to Jay. I could feel my tits bounce uncomfortably. I had worn an under wire tonight. My 40D breasts had always needed more support than your average tits. Tonight, their confinement was almost painful. My nipples were hard, for sure, and aching. My bra had a way of making that happen. Feeling the hard nubs rubbing against the seam of that contraption was more than I could take.

"I'll be right back, gentlemen," I said as I leaned forward, rising from my place on the sofa. "I'm going to change. I think I spilled something on this. You don't mind, do you?"

Jay and Billy exchanged glances. I'm sure, though they said nothing, neither minded that I was changing into something 'a little more comfortable' as the expression went. I smiled, thinking of myself in some hokey porn film. Of course, if that were true, I'd reappear in a black garter belt, with thigh-high fish net stockings, a lacy black bra and no panties. And who could forget the bright red high heeled shoes! As it were, though, I had no intention of sliding my slightly plump, milky white thighs into anything but a pair of jeans. And as for the heels... I think not. Barefoot is more my style. What I would wear on top was the most important choice though. I desperately needed to remove that under wire. And one with boobs as large as mine just doesn't go bra less. I needed to wear something that would keep my bare breasts modestly covered.

As I opened the door to my bedroom, I had that strange feeling once again. What was going on with me tonight? I kept expecting something odd to happen. And in spite of my lingering fear, I was still amazingly aroused. My pussy wet, nipples hard, and mind racing with thoughts of Jay's hands, his arm around me, and the bulge in his jeans.

I simultaneously kicked my door shut and pulled my blouse over my head. "First things first," I muttered to myself, standing in front of my mirror. I squeezed the clip in the front of the under wire together and released the clasp. Instant relief, as my pendulous breasts tumbled free. Being so quickly exposed to the room's air, my nipples became even more taut, puckering a little. I had always liked my smallish pink nipples. The areola were an even lighter shade of blush, which against my fair skin were barely perceptible. I ran my thumbs across them, grazing each nipple as I did. And as horny as I was, I couldn't resist giving each nub several gentle pinches, ending with a much stronger twist as I allowed them to drop from my hands. With a jiggle, they fell into place in front of me.

I was just reaching for my sweatshirt, when I got that odd sensation one sometimes gets. The feeling of being watched. I looked toward the door on my left, and noticed it slightly ajar. I must not have closed it all the way. I was about to push it shut the rest of the way, when Billy stepped into the room. There I stood, with my sweatshirt in my hand, naked from the waist up. Our eyes met, and I could see the desire in his. What did he see in mine? Surprise? Annoyance? Fear? Maybe a little of all.

"Get out, please," I stated firmly. "I'd like to change in peace."

"Er... I'm sorry. I was looking for the bathroom. I didn't mean to intrude," came the words from Billy's mouth. He was frozen in that spot, his gaze locked on my full, hanging globes.

"Get out, then," I repeated, becoming more perturbed.

"Hey Billy, hurry up in there," said Jay as he walked up to the now fully open door.

Well, shit! Now they've both seen me practically naked. What was I supposed to do? I could tell that Billy was somewhat taken aback, but aroused. His bulge had grown noticeably. It was possible that he actually had that monstrous cock he'd been bragging about. I decided to make use of this awkward situation. And, reaching into my sewing basket and pulled a tailor's tape measure out. "Billy, if you'll kindly drop your drawers now, we can settle this bet," I said matter of factly, still bare chested.

Billy began to unbutton his pants, and I moved to pull my sweatshirt over my head. Jay, who had appeared to be stuck for what to say or do, surprised me by coming out of his stupor and saying, "Don't. I want to look at you." He reached for my sweatshirt and for some odd reason, I acquiesced, handing it to him. His appreciation was evident, as his cock grew visibly harder inside his faded denim jeans. God, how I wanted to reach out and press my hand against his growing hardness. To feel the length of him as it expanded in his pants.

My thoughts were interrupted by Billy, who had completely removed his trousers. His partially erect penis hung clumsily between his legs. I could tell it was going to be a close one, this bet Jay and I had made. Even semi-hard, this cock was a complete monster!

"Why don't you work it up a bit more?" I suggested to Billy.

"Why don't you?" he returned.

Without saying a word, I took him by the hand, and led him to the edge of the bed, where he sat of his own accord. Kneeling between his spread legs, I took his pole in my hand for the first time. It grew in hardness even then, as I touched it. I began stroking up and down the extreme length of his cock. Slowly, and with quite a bit of pressure. After only a few seconds, I saw a drop of precum form at the slit. I bent my head to scoop that glistening droplet from his cockhead with my tongue. I took a deep breath, closed my eyes, and gently licked the sticky bubble from the opening. Billy moaned audibly, which sent a jolt straight to my cunt. I took as much of his huge cock into my mouth as I could, closed my lips around it, and sucked deeply as I drew my mouth upward along the shaft. His cock grew hundredfold at that. Just as he reached for my head, as most men are wont to do, I withdrew my mouth, looking over at Jay, who was now rubbing his own raging hard-on through the material of his pants.

"Hey! What are you doing?" queried Billy, somewhat confused.

"Time to settle the bet," I replied. Producing the tape measure and applying it to his now fully erect member, I declared proudly, "Looks like you have 11 and a half inches of hardened manhood here!" Secretly, I was unimpressed, but I didn't let on to that.

"Pay up," I said to Jay, smiling.

"I'll make good on the bet," said Jay with an odd look on his face. With that, he walked over to me, took hold of my hand, and helped me up. Pulling me to him, he kissed me hard on the mouth. I could simultaneously feel his throbbing cock against my hip, and his soft, moist tongue, caressing my lips as he withdrew his mouth from mine. Opening my mouth just a little, I resumed the kiss, this time accepting his tongue into my mouth. Our tongues danced like that, caressing each other for several minutes, before I looked over to where Billy was sitting. He was now stroking his own cock, watching Jay and I kiss like that.

I pressed myself against Jay, walking him backward toward the bed, where he sat next to Billy, who was still hard as a rock, and slick with precum, running his hand up and down his huge cock. I began to unfasten Jay's pants, and he lifted his ass to assist me in sliding both his Levi's and his BVDs down to his ankles. He pried off his shoes and removed the entire works completely. There stood his cock... it was a sight to behold. It wasn't nearly as long as Billy's but it was thicker than average, and had the most beautiful, purple cockhead I'd ever seen. Taking that into my mouth would truly be a treat. I looked up into Jay's eyes, and could see the desire there. He placed his hands gently on the sides of my head, stroking my hair. I only wanted to bring him pleasure.