Paid Waiter Stripper

She found me in the "Help Available" site when I was in my first year of college. My ad was accompanied with a nice picture of me in shorts and a snug fitting t-shirt. That, and my grin, was what attracted her to me. We'd made a deal that I would work as a waiter for her Ladies Party at her gated community home. She'd outfitted me with a nice tight white shirt and matching short shorts. Under that I was to wear the nice new white jock strap she'd also gotten for me. She'd had a small sign embroidered on the tail of the shirt that said, "Touching Is Fine, Even Encouraged."

At the party there were seven other women all nicely dressed and in the same age bracket as my employer. During the evening I'd had hands all over my chest and back, and a few caressed my buns and squeezed. One lady took a $10 and holding it up for me to see, slowly slid her hand down over my package and gave it a nice gentle heft. This was in plain sight of the other ladies and she made a comment for their benefit, "this feels like prime young hunk girls, you should help yourselves. You don't mind do you honey?"

Deliberately pushing my crotch into her hand "No I do not mind. It is nice. I like it." By now some of the ladies were getting ready to leave and a couple had gone. The next lady took another $10 and played with my ass for a few minutes. During that time I spread my legs a bit and she went down and felt my balls from the bottom. At that point the host lady came waving a $20 and after kissing me on the cheek and neck, gave me the bill and said softly to me "this is for down the front of your pants... is that OK with you?"

My smile told her it was a 'yes' and her hand was soon around my soft cock and balls. Two other ladies quickly followed suit and I was beginning to get aroused...for sure. At that point the host lady asked me to take off my shirt and I did. She then asked me if I had on a nice jock strap. When I acknowledged I did, she asked to see it. "Show it to all of us."

And so it was that I was walking around dressed only in a jock strap. More ladies left and it was now just me and four nice ladies. After collecting a twenty from each of them, the host lady slowly kissed me on the mouth, and slid down the jock strap. By then my dick was at full mast and it pointed right up at the ceiling. Wrapping her hands around it she commented, "this thing is beautiful girls. Since he has no place for putting money now, I'll compensate him handsomely and offer him to all of you for whatever feeling and fun you may want...as long as he agrees. And we can see he is an agreeable hunk."

Pretty soon I was being kissed by each lady who promptly got a handful of my cock and balls. One lady in particular french-kissed me and took my hand and put it on her breast. "Seems like you getting some feels too is fair." Now the other two ladies left and it was just the host and the french-kissing lady. On another pass, as the host was ushering out the remaining ladies, she took my hand and this time slid it down between her legs. "I'm staying around for dessert with the hostess...we are going to eat you up...and fuck you silly."

In short order I was in a large master bedroom with two naked middle aged but well built ladies, rolling around on the California King Bed. It was huge but was a wonderful playground for me and the naked ladies. They had been taking turns sucking me while the other was kissing me. I got plenty of titties play time, but never more than my fingers in their pussy. Whenever I tried to do some oral sex, the other one would want to kiss me and so it went.

The hostess produced a box of a dozen condoms. "We probably won't need all of these, but I do not want to run short of wearing out that wonderful cock of yours." By now I realized that the women were very bi and that was part of the reason I didn't get to do any oral sex on them...because they were into each other in that way. It was a powerful blast on my 18 year old mind to see a nice lady, my mom's age or older, having her head between the legs of another woman giving her oral sex.

My cock entered the hostess as she was eating out the other lady another time, and she stopped for just a second and moaned..."ooooo yyeeesssss". By now I had gotten to the boiling point and had passed... the stimulation of my cock being buried in her sweet pussy felt great, but I really had no urge to cum as long as I slowly stroked in and out of her which seemed just fine.

After a bit she got off the other lady, and I saw that as my signal to service that woman. I was going to change condom, but was quickly pulled onto her showing me that the same condom was just fine in her pussy too. She was definitely hotter and wanting my dick really deep. It was then I felt the hostess fooling around with my balls...and something warm and wet at my rosebud. Soon some sort of toy was sliding up in my ass as I fucked the other woman. I was getting close when it felt like lightning had went off in my ass! She'd turned on some sort of vibrator and that buried up so deep in my ass...and my dick burning up in the hot pussy, I blasted the biggest load I am sure of my life.

So that was the first sex of my hired waiter venture. She gave me 10 crisp hundreds as I left and said she wanted to have another party soon and asked if I could 'serve'. "You bet...with pleasure. Great pleasure!"