The Pool Boy Gets Some Action!

Penthouse Letter 4 Pool Boy

I live in Hollywood where I am one of the many out of work actors trying for his big break.  Work is hard to come by out here.  Without a good job, pussy is too.

One time I took a job cleaning pools.  It was a good way to keep my tan and to see how the truly wealthy lived.  Most of the time the people weren’t even home.  I doubt they swam in the damn pool either but my paycheck cashed and I had free time for auditions.

One time I was cleaning a pool in the hills and the owner was around. She was an older woman, probably in her early 40’s.  She looked pretty good for her age in a way that money helps.  It was a hot day and I wasn’t wearing a shirt while I worked.  She sat inside the house watching me.  I first noticed her looking while I was getting chlorine she was in the kitchen looking out the window.  Later when I was cleaning the bugs out of the filter I spotted her looking at me from the sun room. 

After I had finished and before I left, she asked me if I wanted something cold to drink.  I wanted something to drink alright.  I agreed.  I asked her if her husband was around.  She said she was not married.  She lived alone.  I should have known, the place was as tidy as could be.  It looked like Martha Stewart’s place. 

My host asked if a number of clients come on to me.  I told her that I had just started and that she was the first.  “I am not coming onto you!” she stammered.  She was embarrassed. 

“I am sorry, I can go” I said. 

“No, please stay.”  She continued with “I am all alone”

I began to feel bad for her.  She had obviously found success enough to afford this home yet she was still alone.  I introduced myself as Jim.  Her name was Tina. 

Tina looked like an attractive woman.  She was wearing white cotton pants, a long sleeve shirt, and white sneakers.  She was very preppy and not really my type.

“It has been a long time since I have been with a man” She said.  I didn’t know if it there had been women in the meantime or if she was trying to talk about her dry spell.  I think she was alluding to a long bout of bad luck.  I didn’t know what to say so I sat there silently. 

“Do you think I am attractive Jim?” She asked. 

“I do.  I think you look very nice in your outfit” I said.  Where the fuck did I come up with that?  Outfit?  What was I thinking?  Tina leaned over and started kissing me.  It was a little awkward like a fifth grade spin the bottle kiss.  She didn’t seem to know what she was doing.  Soon though she opened her mouth a little and we explored each other with our tongues.

As we went down the hall to the bedroom Tina again said something about not being with someone in a long time.  I didn’t know what to say so I just kept my mouth shut.  Didn’t Ben Franklin once say it is better to keep your mouth shut and to be thought an idiot than to open it and not get laid?  Either way I followed Tina to the bedroom. 

I was already shirtless so I began to take off my shoes, socks, and pants.  I was free-balling that day and I was very quickly naked.  Tina gasped at my naked body.  She was really staring at my penis. 

I moved closer to her and started to remove her top.  I tried to do this in a sensual way but it was a little clumsy.  The neck of her top got stuck on her chin and for a while she looked like the loser in a hockey fight.  While she was struggling to remove her top I noticed the wrinkled skin of her upper chest.  I had only been with younger women at this point and this excess skin did not strike me as attractive.  Soon her top was off and we were kissing again.  I removed her bra.  Fortunately, that went more smoothly.  It wasn’t an Arthur Fonzarelli one-hander but it was close.  Her breasts were small and fairly firm.  I was very excited to touch them and she reacted positively.

I bent down to remove her pants.  I gently nudged her to lay down on the bed while I wrestled her chinos off of her hips.  I grabbed her panties at the same time and off it all went.  I looked down to see what appeared to be 40 years worth of pubic hair growth.  It looked as if a man with an afro had beat me to the cunnilingus portion of today’s event.  I couldn’t believe the size of her bush.  Damn, I thought, she needs to sleep with the guy that trims the fucking hedges. 

Regardless, I figured a woman like this was used to the best so I went down.  It was a little uncomfortable with all of that hair but I managed to go under it and do my thing.  She was very appreciative.  So I guess it was worth it.  Despite all of the strange things that I was experiencing my unit was ready to go.  I slowly got on top of Tina and inserted my cock into her pussy.  She cooed and moaned that it felt so good.  It did feel good.  I did my best to make love to her in a sensual way despite the fact that I didn’t know a thing about her.  I wondered if this is how gigolos feel.  Eventually, it seemed that Tina had enough.  I thought of something erotic and got myself off. 

When I was done Tina told me “That was great” but not in a very convincing fashion.  I left the house soon afterward and drove home.  The next week the boss told me I was fired.  He said it just wasn’t working out. 


Pool boy.