Chapter 2

Next door lived a kindly middle-aged man, Mr Hobbs. He was divorced and lived alone. He had recently talked about getting me laid for my 14th birthday. This prospect was exciting, but at the same time terrifying. I wanted to do it but I was too afraid. I was also too embarrassed to admit that later part so I just said I would let him know. The events of this afternoon, how sexual mom’s foot massage had become, cinched it.

In the moment I was still on the hassock. Mom kept looking at the throbbing bulge in my pants but didn’t move. She kept on reclining there in front of me in her underwear, her bare feet in my lap. Jennifer, for her part, walked away laughing. I went to my room, red-faced and ashamed. I managed to squeeze out “you’re welcome” when mom thanked me for the massage.

I had stashed away in my room a copy of the previous year’s “Sports Illustrated” swimsuit issue, featuring Paulina Porizkova. I stared hard at her layout, constructing a scenario in my mind where I was there in Aruba with her.

I started with meeting her on the beach. After a minute or so we were making out and rubbing our hands on each-other’s bodies. She took me to her hotel, and barely got the door closed before I had her bathing suit off of her. We made out on the bed for several minutes before she reached to take off my trunks. She pinned me on my back, climbed on top, and proceeded to straddle my dick. This, I thought, was the best mental image. Paulina Porizkova was sitting on me, riding my dick. There was no way any thought of my mom would invade this fantasy.

I pulled out my dick to to play with it to images of Paulina, and only of Paulina. This lasted a few seconds. Just before I started to cum, she had morphed into my mom. Damn it all!

By this time Mr Hobbs was home. I cleaned myself up and went over to see him. I told him I was ready to take him up on his offer and asked how soon we could do it. He said he didn’t have any solid plans for that night and would like to do it then. So it was all set. That evening I left with Mr Hobbs.

He took me downtown to a brothel. The madam who ran the place showed me an assortment of women from whom to choose. They ranged in age from 18 to about 30, and were of various heights and body types. One really stood out.

Janis was at the upper end of the age range. She had a breathtakingly beautiful face. Her body was quite curvaceous without being overweight, tits and ass for days. She seemed a bit surprised that I had chosen her instead of one of the younger women, maybe even flattered. She was ready to get down to it.

On the other hand, Mr Hobbs was clearly dismayed at my choice. With a look of total bewilderment, he looked from her to me and then back again. “Are you sure this is the one you want?”

The madam told me not to listen to him, that it was common for young pups to be interested in older women. If I’m going to be with someone twice my age this was the time to do it.

Still in shock, he said, “Yeah, but really...” and just sort of trailed off. He looked like he wanted to say something more. Then he held up his hands, sort of nodded, and said, “It’s your choice. Have fun.”

I kissed Janis right there in front of everyone. She started to kiss me back but then pulled away. She said, “Not here. We have rooms for this.” Taking me by the hand and leading me to one such room, she added, “I have so much to show you.”

We eventually got to her naked body, which was the most amazingly beautiful thing I had ever seen. This was in the midst of “showing” me things in the form of demonstrating techniques. It was more telling, more instruction. I learned so much that night. The lesson on kissing alone blew my mind.

She started by teaching me to pucker just a little, and push my lips forward slightly, to feel the slightest hint of muscle tension around them. I wanted to aggressively go in for a fully open-mouthed kiss at first. But she had me open my mouth slightly, keeping my lips just barely parted enough that a tongue can slip between them. She had me follow her lead, and we made out just like that for several minutes. I followed Janis’ lead the best I could. She let me explore her body a bit with my hands. After moving around some on her hip and thigh, I moved higher and rubbed her back and shoulders. The longer we kissed the more natural it seemed. Then Janis changed things up a bit. Sliding her hands all over my back, she lightly brushed her lips over mine, so our lips were barely touching. I wanted this moment to last, so I resisted the urge to attack her sexually. I did squeeze her hip some and caress her thigh. Janis kept her movements slow. She proceeded to lock lips in such a way my lower lip was between her lips, lightly sweeping the tip of her tongue over my lower lip in one smooth motion. She pulled back and said, “Now you try it.” When I brushed my lips over hers, she slipped her tongue into my mouth. We explored each-other’s mouths some more.

As we explored each-other’s mouths I was aware I was already cumming in my pants. I figured it no matter, Janis could easily get me hard again. It turns out that wouldn’t even be needed. I shot a nice sized load but remained hard as a rock. This woman was so sexy, she turned me on that much.

Then I gently locked onto Janis’ bottom lip and swept it with my tongue. She pulled back, just long enough to say, “You are really good at this! Keep following my lead.” Opening her mouth wide she slowly slid her tongue into my mouth. Her tongue was touching mine from above, then she slid around the side to the bottom. I reciprocated and we were just circling for a few seconds. Then Janis pulled her tongue back, then forward again to playfully tag my tongue and retreat back again a few times. I did the same. We played this way for a minute or so, keeping it shallow and light. Then Janis broke lip contact again. She touched her forehead to mine. Hands still on each-other, we just gazed into each-other’s eyes and smiled. When we resumed kissing she breathed through her mouth a little, sharing breaths with me. I couldn’t believe how much this turned me on! She began varying the speed of her kisses. Slow, then a little faster, then slow again. She began to go deeper. She kissed me hard and forcefully probed my mouth with her tongue. This went on for the better part of a minute, with me doing my best to keep up and match her moves. Then she rubbed my teeth with her tongue, the backs and then the fronts. This tickled a little, and I loved it! As I was returning the favor, Janis pulled back just enough to lightly catch my bottom lip with her teeth and nibbled on it a little. I reciprocated this as well.