Finally after three weeks of jerking off, including several times while staring at the picture in the ad it occurred to me why not do it? I could save up the money and it’s not like anyone would know. I’m sure it was something my parents would frown on, and I wouldn’t tell any friends, especially Jimmy because I would never hear the end of it.
Once I’d decided to chase my fantasy I’d looked at the ad every day hoping that whoever she was she would keep doing this. Right now all my bills were paid including the money to my parents to go in the bank. I had a hundred and sixty stashed and after the couple of jobs today would have two. Staring at the ad I wondered if I should contact her now. No, I had to get to work and…
“What are you doing, looking at hookers again?” I jumped as Jimmy came up behind me. “Shit, all the hotties we saw and you’re looking at the old lady?”
“Like you wouldn’t tap that.” I responded, pointing at her.
“I wouldn’t pay for it.” Slapping me on the shoulder he laughed, “Hey, Nick you want to bang a cougar, Miss Jennings is single!”
“Ugh.” I gave a mock shudder, “Dude, she has false teeth.”
“Then she can take them out and give you a gum job!”
I shut the computer off and got up to see Jimmy tossing a t-shirt on. “You about ready to go?”
“I have to shower.”
“Why, we’re going to get all sweaty.” He reminded me, “But really, you know if you want some desperate housewife go hit the bar over on Broadway lot of lonely ladies there.”
“How do you know?”
“Oh, well…” he looked away.
“No! You fucking dog!” I exclaimed “Have you really…?”
“I’m not proud.” He made a show of hanging his head, “But she was lonely and upset and I took one for the team and made her…”
“How old was she?” I asked.
“I don’t know, maybe thirty,” he grinned wickedly, “Old enough to know some tricks.”
“You never told me.”
“It’s none of your…”
We looked up at the sound of heels coming down the hallway.
“What’s your mom doing up before nine on a Saturday?”
“I have no…”
He stopped at a knock on the door and Wendy calling, “Hey you guys decent?”
“Yeah,” Jimmy called back as I reached down and grabbed a Red Sox shirt from my bag and started to put it on.
“I should say as decent as a two twenty year old boys can be anyway.” Wendy laughed as she entered the room.
“Morning, Wendy, I…” I stopped in mid sentence when I saw her.
Wendy was wearing a black skirt so short I doubted she could bend over in it and a pink short sleeved blouse that wouldn’t be anything special if the buttons were secured. Instead the top half was wide open exposing a red shirt beneath it that was low cut to where I could not just see the top half of her tits, but a red lace bra.
Her long blonde hair was down despite how hot it was outside and I noticed she was wearing eye shadow to accentuate her blue eyes and her lips were painted a deep red. Catching myself staring at her chest, I dropped my eyes down and was now confronted with her almost totally exposed legs. Wendy sun bathed by the pool every day and her legs were not only long and well shaped, but as tan as I was from working outside all summer.
wpDiscuz