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Chapter 3

How do you hit on her at a casual pool day? (Or somewhere else?)

At a wine bar after work

When I knew Sherry, she was a new intern in our office. It was old Vern, the caretaker's leaving do and we had all decanted to Vixen's wine bar after work for his sendoff. Sherry was eager to make a good impression and slightly nervous. This nervousness however made Sherry consume her pinot noir at a more accelerated pace than most, so that by the time the rest of the staff were making their farewells (they all had boring family commitments), and we had even poured old Vern into a cab for the night, it was just me and a more than tipsy Sherry remaining. Of course I had my eye on her and her massive boobs from the day she walked into the office.

Sherry could talk about almost anything and I was not paying much attention.

"You look great in that dress", I said, interrupting her flow of consciousness that she was pouring forth.

"Thank you. You're nice!" she smiled and nudged me.

"The floral print really goes with your personality". I nudged her back, elbowing her in the left boob.

She ignored that.

I leaned in close to her and whispered in her ear, "and your tits look great in it".

She sat back and blinked twice attempting to focus on my face, then burst into a fit of giggles.

I meant it. The dress was short and low cut showing a prodigious amount of cleavage with her massive boobs stretching it across the front in twin vaguely conical shaped mountains trying to burst through.

"Wanna dance?" she asked as a track she liked came on. There was no dance floor, just the little snug area that the office had been using for Vern's do, which was fairly secluded. Being a weeknight the wine bar was almost dead anyway.

"Sure. Why not?" I got up and extended my left hand in a traditional waltz maneouvre.

Sherry looked at me disbelievingly, then shrugged and slipped her right hand in mine and placed her left on my shoulder.

Instead of sliding my right around her waist, I went straight for the prize and grabbed her left boob with it. In a fairly unorthodox hold, it took Sherry a few seconds to realize that I was happily groping her lovely soft boob through her dress. When she did, she looked down at the hand happily squeezing her tit, then back up to my face questioningly.

Without a word, and with an exagerratedly disappointed expression. I reluctantly took the hand from her tit and put it on her waist where she might have expected it to land.

Sherry looked annoyed, reached down, clutched my hand then brought it up determinedly to her breast and placed it once more on prime groping position.

I didn't neeed any more encouragement and lost myself in the whole song squeezing and groping her tit while we danced. Sherry leaned in for the kiss and we made out.

Sherry seemed more dazed by the time the song was finished and I could sense that my window of opportunity was narrowing if I wanted to get more out of the evening with this plump young beauty.

"I've got a nice bottle of chardonnay back at my place if you want to try that?" I said in her ear, still holding her left tit firmly in my right hand.

Sherry nodded and grunted assent, so I led her as quickly as I could to the exit.

In the cab on the way to my place we continued kissing, and I had my hand up the front of her dress, in her panties and finger banging her the whole way. She opened her legs wide ground her pussy onto my palm as two of my fingers **** their way into her over and over again. I'm sure the cabbie must have noticed, but he said nothing.

Getting out of the taxi though, I had to help her walk up the drive, and by the time I had her in my front door she had all but passed out.

Shit! Should I?

Fuck!

Well, I didn't anyway.

Maybe it was a sense of decency, or maybe it was the fact that I would have to face her again at work, but I decided not to fuck Sherry while she was ****. I'm not a monk though, so of course I stripped her and saw those lovely big titties that I had been lusting after along with the rest of her XXL awesomeness.

With a slight sense of despondency, I sat beside the naked **** Sherry and stroked one off with one hand, the other hand groping her big tits again as I did, gently tweaking her nipples and pulling them towards me.

Afterwards, I threw a blanket over her and for fun, shortened the straps on her hefty bra as much as they would go.

When Sherry emerged the next morning from the bathroom, she looked at me with a curious smile, wondering what we might have done, dressed once more as she was the night before, but with her tits almost up under her chin.

I lost track of Sherry shortly after as we both moved on from that office, but I'm sure she'll still be as much fun to be around as I remember.

What's next?

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