Girlfriend Loses Bet, or Did She?

I met Carolyn sometime in the early 1980s, '84, I think, from memory, about 18 months after separating from my first wife.

It was a Friday night when usually, straight from work (a job that kept me in good shape), I went to my local bar.

My Friday after work routine was to hit the bar for two to three hours, playing pool and shooting the breeze with my buddies.

Then I'd go home, shower and change, join forces with a similarly single mate and go into the CBD to hit the clubs, meet girls and hopefully get laid.

But this particular night, my routine was jolted out of its rut.

Because I met Carolyn and all that changed.

Carolyn, 30 at that time, 4 years my junior, was perhaps on the plain side of pretty, but certainly not unattractive. She possessed a beautiful smile and an infectious chuckle that could cut through the rowdiest crowd: I often heard her before I could see her.

I really can't explain it, but I couldn't take my eyes off her, that night. Between her chuckle, a body made for fucking and a mouth to put Linda Lovelace to shame, she sent my head into a spin.

Did I mention her body?

Her gorgeous body: 5' 4" (160cms) and 140 Ibs (65kgs), give or take, nice and slim without being skinny, plus memorable breasts--I'd guess a bouncy 34B.

When she's on top and dragging them across my face, her generous nipples fall into my mouth and I die and go to heaven.

Along with a pleasantly freckled complexion enhancing a pert, slightly upturned nose and sensuous lips, she just looked a little sluttish, naturally. As a bonus, her public bush was neatly shaped and trimmed so short that it hid little (not that I knew that, yet).

Did I mention sluttish?

Now, I like sluts. Sluts attract my immediate attention.

My newish current partner is a slut (I pimp for her; stories to come soon) and I love her for it. It gives us both intense pleasure when she has another's cock deep in her pussy and my (or yet another guy's) cock in her mouth.

Especially when we show all the fun on live cam.

But that's still far, far in the future.

Right now, on that fateful evening, I was standing at the bar with my group of regular drinking buddies.

Carolyn was with a group we recognised as from a local business, although Carolyn herself was unknown to us. It turned out this was only her second ever visit to our pub.

And as I said, she caught my eye.

So, I checked with a young guy in her group, as he walked by, that she was single, and when he replied in the affirmative, I asked for her name. A little later, as she passed me on the way back from the rest rooms, I greeted her by name.

"Hello, Carolyn. Great to see you here tonight."

And I smiled my nicest smile.

She stopped and looked at me, quizzically, her lips forming an uncertain smile.

"Um, hi. Do I know you?"

I detected a strong British accent.

"You do now," I grinned, cheekily. "I'm Pat. Nice to meet you," saluting her with my glass.

Her demeanour remained uncertain but friendly, if you know what I mean.

"How do you know my name?"

"I asked that young guy over there."

"Oh, him. Of course he'd tell. He sings like a bloody canary."

Canaries sing? Who knew?

"Would you like a drink?" I enquired, rather hopefully, but...you never know your luck.

There was a moment's pause and our eyes locked, until she broke it by telling me (literally: it wasn't a request) to hold her handbag while she fetched her existing drink from her workmates' table (her handbag weighed a bloody ton!)

And that was that. I drove her home from the bar that night and never left, eventually giving up my flat and moving in with her in the same house (same bed) she had previously shared with her ex.

Anyway, a month or so after hooking up with Carolyn, I had to drive to my old home town for a family occasion. Carolyn was happy to accompany me, and I organised for us to stay with my younger sister and her husband, who was about my age. We arrived late Friday afternoon, the night before the big event.

After introductions, my sister, Ev (short for Evelyn), and her husband, Olly, suggested we go to their local bar for drinks and food.

"A damn fine idea," I said.

By the time we enjoyed a few drinks, then a leisurely dinner, the clientele had thinned and the pool tables were largely empty--we mainly play 8-ball in New Zealand. Olly and I both enjoyed a game, and so, I had already discovered, did Carolyn

In fact, she was pretty good, and actually had won the odd game playing against me, but I'd trust my game over hers if there was something on it. We started playing while my sister wandered off to catch up with friends.

The first hour was uneventful, with me losing to Olly, Carolyn losing to Olly, me beating Olly and Carolyn beating me (hey, I was taking it easy on her!). The next game was due to be Carolyn vs Olly, again.

Now, drinks were being consumed at an accelerating pace.

I started the fun as Olly readied the balls for his break. Yep, it was me, when I suggested they make the game more interesting. Carolyn was keen.

"I'll show my tits if he wins and he drops his gear if I win," she volunteered.

I hadn't expected that. Usually I have to wheedle and cajole, sometimes bribe, to get dates and girlfriends and wives to have a little spicy fun.

Olly grinned and agreed.

Olly duly broke and all of a sudden play became more serious, but Noel eked out a narrow win.

Without conferring with me, Carolyn said:

"I already owe you my bra. This time, I'll throw in my shirt."

Olly, with literally nothing to lose and not one to look a gift horse in the mouth, nodded so furiously his jowls wobbled.

As if to accentuate her assets, Carolyn drew herself up to full stretch, taking a deep breath, her nipples clearly outlined through her clothing, before addressing the table to break.

Sure enough, she scored off the break and sunk a couple more before missing a corner shot. The game then see sawed until Olly eased ahead. But it was close, again.

Carolyn looked at her opponent and said just one word, "Skirt." It wasn't even a request and she immediately began racking the balls for the next game.

By now, my sister had returned to us, and was not impressed with what she was hearing.

But we weren't hearing my sister.

And when Carolyn duly lost that game and insisted on one more chance, Ev flounced back to her friends, who were now watching the unfolding events with interest, having got wind of the stakes at play.

Even I quietly asked Carolyn if she was sure she wanted to go there.

"So long as he wants to play, I'll fucking play," she snapped. "Just sit back and watch the fucking show."

Well, when it comes to all things sex, I do love a dominant woman, occasionally. So I meekly resumed my seat.

In this game, her panties were at stake, so the price of failure was rising. Olly seemed a little distracted, no doubt inwardly relishing the prospect of seeing Carolyn naked, and almost lost. Almost.

Ev had returned and demanded to be taken home. Carolyn skulled her glass and said to Olly, her forefinger in his face, "One more!"

Olly replied, "But you've already lost everything!"

Carolyn whispered in his ear and he nodded his head, grinning enthusiastically. He turned to my sister and said, "One more game, and that's it."

Ev wasn't happy but Carolyn was already racking the balls, and she immediately broke. One went down, then another, and another before she accidentally snookered herself, missed her next shot, giving the table to Olly. They swapped a couple of turns before Olly was on the black, sinking that and winning the game.

Carolyn wasn't saying much, seeming quite pensive. I quietly asked Carolyn what the stakes were, this time, and she whispered, somewhat cryptically, "Full strip plus."

"Fucking hell," I thought. "Who is this girl?"

Olly returned the cues to the their rack and turned to us:

"OK," he said, "we better take this home and finish up there."

"What about your wife?" Carolyn asked Olly.

"Let me worry about that," replied Olly, puffing out his chest a little as though offended by the question.

Knowing my sister, I had my doubts, but the three of us had drunk enough to be feeling no pain, by then.

Caroline pecked my cheek and said to both Olly and me, "Lets go home and get the show started, then, shall we?"

Whispering in Carolyn's ear after we returned to the car, her and I in the back seat, my sober sister driving, I asked her if she would really go through with it. Her reply gave me little shivers of joy.

"You really don't know me very well, yet, do you?"

And she smacked her lips onto mine with a loud, wet kiss.

"We really should," she continued, in between kisses, "rectify that."

I reached under her skirt and her panties were wet, really wet. And hot. Her pussy was on fire! As was I, especially since she was rubbing me through my jeans.

"We should," I murmured into her mouth.

Back at my sister's, we gathered for a nightcap and a chat and, of course, showtime.

Time passed. Olly put music on, and we listened to a few tracks.

Then I realised we were all waiting for Ev to take her grumpy face to bed so Carolyn could fulfil the bet. But Ev seemed determined to wait us out and stare us down.

Well, I'm the older brother.

And I'm not known for my tact. I mean, to be honest, if Ev was my wife I'd be telling her to join the fun and get her gear off, too!

Instead:

"Okay, sweetheart," I said to Carolyn, "don't worry about ol' prune face over there, what music would you like?"

"I've got it!" Olly exclaimed. "Just gimme a sec," as he was already slipping another tape into the stereo.

Ev frowned. Oh boy, Olly was gonna get it later, I thought!

Carolyn stood and gently swayed on the spot as she waited for the music to start.

She was facing Olly and me, sitting in armchairs; my sister was on the couch, behind her.

Olly pressed play. The husky, sultry tones of Stevie Nicks filled the room. Carolyn began her show.

For a minute or so, Carolyn continued swaying, not removing a stitch, letting the sexual tension slowly build.

Facing the men, she slowly ran her hands over her breasts and her bum. Then, facing away (but avoiding the hostile gaze of my dear sister), she flicked her skirt up and over her bum, displaying her very shapely butt and sexy panties.

Turning to face the men again, she lifted the front of her skirt and sensuously rubbed her pubic mound, finally slipping her right hand inside her panties and teasing us by suggestively wiggling her fingers under the thin fabric.

All the time gently swaying to the beat.

My sister remained unimpressed, going by the scowl on her face.

Mentally shrugging my shoulders, while looking closely at Carolyn, I thought I could see a small wet patch appearing between her thighs.

I knew from our lovemaking that her fluids flow could be copious.

Next, Carolyn began slowly, teasingly, undoing the buttons on her blouse.

When they were fully undone, she opened it wide, smiling seductively.

Olly looked like all his Christmases had arrived at once as she dropped it to the floor and, without pause, unhooked her bra to allow her gorgeous tits to fall free as her bra joined her blouse on the floor.

My sister was making clucking noises of intense disapproval and I fervently wished Olly would send her off to bed.

Carolyn told me later my sister's open disapproval motivated her to finish the job quickly, before Ev called a halt.

So Carolyn now stood in front of us, tits out and hanging loose, then reached under her skirt to remove her panties. After giving them a quick twirl on her forefinger, she tossed them at Olly, who promptly held them up to his nose--all class, that boy.

Finally, Carolyn dropped her skirt to the floor, joining her bra and blouse. And stood directly in front of Olly, one finger in her mouth, another just flicking her clitoris peeking out from between her labia.

Thank fuck my sister couldn't see that, I thought.

But Ev had had enough, anyway.

"Oliver, we are going to bed, now!"

As the door closed behind them, Carolyn turned to me and beckoned with her head to follow her. Still naked, leaving her discarded clothes where they lay, she led the way down the stairs to our room.

As soon as we were inside, she laid back on the bed, opened her legs and said, "That was so fucking horny! Just get your cock inside me, now!"

My cock was swelling rapidly as I stripped off my clothes. I climbed between her legs and entered her very, very wet and sloppy vagina and started stroking.

Carolyn responded as enthusiastically as in any wet dream. Her regular sharp intakes of breath indicated a series of orgasms, which she could keep up forever.

The distinctive, splashing sounds of her flooded pussy as our pubic bones slapped against each other filled the room. I wondered briefly if the noise carried upstairs.

And I remember thinking the bed cover was going to have a bloody big wet patch!

I rolled off for a rest and we lay side by side, panting, sweat beading both our bodies.

Eventually, I asked her, "How far were you willing to go?"

She knew what I meant.

"How far is there to go?"

A question in reply to a question is avoiding the question, so I pressed again.

"Would you have bet a blow job?"

"Easily."

Holy shit. Is she fucking with me?

She rolled over so her face was above mine, and close enough so our lips were almost touching.

"Would you have liked to see that?"

I shivered and an acute case of goose pimples broke out all over my skin.

"Oh! You would, wouldn't you?"

And I was sprung.

She moved to be fully on top and slipped my cock into her pussy.

"And what if I had bet a fuck," she whispered into my ear as continued fucking my cock. "And I had fucked him while you watched and he filled my pussy with his sperm?"

I was breathing very heavily, by now, and I could feel the beginnings of the irreversible final march to ejaculation.

"I wanted to, you know," she continued, breathing into my ear, "I wanted to fuck him because I already know this about you, that you would love it. You would love to see a nice big cock filling up my pussy, wouldn't you?"

I guess I gave the game away by ejaculating with a loud groan. My body always freezes at this moment, my penis super sensitive as it spurts into the waiting vagina.

While I came with spurt after spurt, she put her tongue in my ear and wiggled it into my canal entrance, breathing her hot breath into my ear, and the fucking goose pimples erupted, again, too.

"So soon?" She quietly queried, smiling, lifting her head as she felt my spasms wind down.

"Was it something I said?"

When I recovered my breath, I asked, "Were you trying to lose?"

"No, Not at all. I just didn't mind losing. Such a shame your sister didn't just go to bed when we got home."

"You wouldn't fuck him with Ev in the house, surely?"

"Yes, I would. I don't care if he's married or if his wife is your sister. I know while I'm with you, I can fuck whoever I want, can't I?"

"In fact," she continued, "I'll even fuck men I don't want, if you ask nicely."

I wondered how much of all this was just the alcohol talking, but let it rest, for now.

The family function next day went off just fine, although it became obvious, from a couple of quiet remarks, that Ev had gossiped to our other two sisters about the events of the previous evening.

Oh well, I'm the divergent in the family anyway.

When we said our goodbyes to head back home, Olly approached us and said he had a work conference in our city in a fortnight, and he invited us to dinner one night at the upmarket hotel where he'll be staying.

We agreed, and on the trip back Carolyn teased me mercilessly about what she would order for desert.

But that's another story.