Many, many years ago I had a friend named Shannon. I can’t even recall how things started, but she was the ex-gf of a friend of mine and he treated her SO badly I think she just liked being around a guy that was kind to her. I was in my thirties, she was probably 23-24 at the time. She was cute, very thin, with very small breasts. But she had really nice legs and an amazing bubble butt.
In the interest of full disclosure, I was happily married at the time. I think that helped her feel “safe” somehow.
She used to come to my office after hours, often bringing something to drink like wine, beer or most memorably, the mixings for white Russians (she loved those). We’d surf porn, talk about sex and trade massages. It was pretty mild but I’m sure wifey wouldn’t have approved!
She’d swing by every so often, maybe 4-5 times a month. It was fun for us both. She knew she could torment me with her tiny boobs and gorgeous butt (my two favorite things)yet things would always remain under control.
One memorable night, we popped downtown to a pool hall for a few games. She was in her usual tight jeans and looked spectacular bending over to take her shots. We were having a blast teasing each other and before long, other guys were stopping to watch her shoot as I egged her on.
For the final game, we made a bet: Loser would have to give the winner their underwear. It wasn’t exactly a wild bet, since she had pants on, after all, but we still had a great time and eventually I persevered. I demanded my payoff and she pretended to be embarrassed and headed for the ladies room. Soon, she emerged, hiding her panties in her pocket saying something about giving them to me outside.
We left the bar and as we walked past a mailbox, she reached in her pocket and dropped her undies in there. In mock-fury, I railed about her welching on our bet but really, I didn’t care. We laughed about it and got to my car and proceeded to head back to my office. I continued to razz her for doing what she did. Then she asked what I would have done if *I* lost. I told her I would have obliged as I wasn’t very shy! Then she asked if I was serious. And I said: “Shannon, if you wanted to see my dick, I’d show you. Why not?”
She looked at me and turned very serious. Her voice lowered and she said in a voice full of lust “right here. Right now.”
Well, didn’t I just screw myself! We’re in my car, mind you. Driving in the downtown of a major city.
When we got to a light where there were no cars tall enough to look in, I threw the car in park, unbuckled my seatbelt and pants and tugged my pants to my knees.
Her eyes were wide and fixed on my crotch. I wasn’t exactly hard but I wasn’t exactly soft, either. Terrified that a cop might pull up any second I got us out of downtown and back to my office parking lot.
There I pointed out how grossly unfair the night turned out, me with my dick out and her panties in some mailbox. I declared that the ONLY fair thing was for her to drop her pants too. And in the relative safety of our empty parking lot, she agreed! Whereupon she giggled a bit and then undid her seatbelt, slid her pants off slowly and there it was… her neatly trimmed bush!
I growled approval and my cock twitched to life at what she did. I told her to turn in the seat so I could see better and she, of course, complied. I let my hand fall on my rapidly swelling penis and she let out a purr of her own. That was all the encouragement I needed! I very slowly stroked myself I told her to play with her pussy. “It’s only fair” I said.
Her fingers slipped to her damp lips and she spread herself open for me, giving me quite a view of her young womanhood. I stroked slowly as she stared at my nakedness. Eventually, without either of us climaxing, we decided it would be smarter to move inside before we got caught. Being early summer, it was still light out and we weren’t exactly secluded. Nor was it a very nice part of town.
How does this get around to the “helping hand” question? Well, there was a bit of an encore of that night. A male friend of mine came by my office and we decided to go shoot pool. I had a stroke of genius and said “hang on… let me call Shannon!” I figured the addition of a cute, unattached female could only make things better! Soon she joined us and we headed out to play some cut throat.
Well, Shannon put on another great show. Mark was as enamored by her ass as I was. She enjoyed being the attention of these two older, married men and tortured us often taking more difficult shots just to bend over. She’d brush against us “accidentally” and give us long looks down her loose fitting top. Once, when Mark went to the men’s room, she backed her butt into me and left it there telling me what a great time she was having. (Mark later made a comment of how “into” me this girl was, but I didn’t believe him. We were just having fun with a cutie around, in my book.)
Soon enough, it was time to leave. We got back to the office and Mark headed home. Shannon hung around a bit longer and suggested we surf for porn. When we got inside, she grabbed me, pulled me close and gave me a long, hard kiss.
Now I was in trouble!
Her hands went to my pants and in a blur we were both naked. I REALLY wanted to remain faithful to my wife, though and Shannon knew this. Her hands were on my raging hard on and mine all over her ass and tits. I told her I really couldn’t go all the way and she said “that’s OK. I have an idea.” She told me to lay on the floor.
She kissed me hard again. “I know you’re a good husband but you need some relief.” Her “idea” was to give me a hand job.
It was amazing. Her kneeling beside me completely naked, both hands stroking my dick. It wasn’t long before I erupted all over her hands and the carpet! We hadn’t thought to prepare for that. When she finished, we sat in my office chair, she climbed up in my lap and we cuddled. She didn’t want me to reciprocate, which probably would have left me conflicted (I know, what a hypocrite!). But somehow it was just right.
We continued to get together for our “surfing sessions” and laughs for a few months but never went quite that far again. Eventually, she moved away and lost touch, though I heard from her on Facebook recently. But there are some memories I will always be thankful for and she’ll always thank me for teaching her what an orgasm is (a whole different story that I’ll get to someday!)
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