An Area of Expertise

This happened in my first year in college. I was horny all the time but also a bit shy and I didn't do too well with girls. I was reasonably good-looking, though I was slight of build and I looked quite a lot younger than my age.

I went to a bar to meet a friend (I spent my first year of college in my home town, and the bars there weren't so strict about under age at that time, but even so I was asked for ID every time I went near one, used to really piss me off because of course I was legal). Anyway, my friend wasn't there.

I felt slightly out of place in this bar, but there were hardly any other people there and I ignored it. Sipping a beer, I noticed this woman was eyeing me. She was dressed in tight-fitting clothes and although she was clearly older than me, nevertheless my penis got stiff when she sort of licked her lips while looking straight at me. As I mentioned, I was horny all the time. And not too fussy.

We were almost the only ones there and she came over and asked if I was going to buy her a beer, which I did, and she slid into my booth with me. She sat close enough that our thighs were touching and said she didn't think she'd seen me in the bar before and how nice it was to see someone new. Her skirt had ridden up her thighs, and it was inappropriately short to begin with. But it looked sexy. I couldn't have said how old she was, but she was definitely older than me, by at least ten years, probably more.

We went through whether I had a girl-friend (no), a boyfriend (I had in fact had some experiences with one or two older boys, and with an older man, but of course I didn't mention that), how surprised she was that the girls weren't all over such a nice boy as me (definitely not, unfortunately). She had put her hand on my thigh, and now she allowed the back of her hand to brush lightly against my crotch. Of course I was stiff as a bottle.

"Oh dear me!" she murmured in my ear, and she kneaded the head of my penis with the back of her hand, gently, but I was afraid I was going to ejaculate. "Is there somewhere we could go? This place will be quite crowded soon."

I gave a moment's thought to the friend I was supposed to be meeting at the bar. This was before cell phones and when someone wasn't going to show up, the only clue you got was that - they didn't show up. I decided he must have forgotten.

My parents were away at the beach house, they often were. I hesitated momentarily about taking her to our house, but her hand gently rubbing on my penis convinced me. We stood up, and I found that she was a little taller than me. I was glad it was so dark, I'd had a couple of beers but I was still thinking clearly enough to know that this wasn't the sort of visitor you wanted the neighbours to see.

I drove to my parents' place and the whole time she kept touching my crotch.

Inside the house I took her straight to the basement, partly because my parents seldom went there. My mother wasn't a detective, but from her powers of observation and deduction anyone might have though she was. The basement was relatively safe from that.

I turned on the stairwell light and there was just dim glow in the rest of the basement. The lady - her name was Pauline - kicked off her shoes and came straight over and kissed me right on the lips. Our tongues met, sending a bolt through me, and she probed quite openly in my mouth. Then she put her hand on my crotch again, and unzipped my fly. Another bolt as she carefully handled my cock, and then used both hands to work my pants and underpants down off my hips and down to my ankles. She took her mouth away from mine while I stepped out of my pants.

In another moment I was completely nude and she pulled me down on the old sofa and kissed me ravenously, sloppy and mouthy, her tongue half-way down my throat. She was handling my cock and my balls too, kneading and squeezing. I was electrified.

I ran my own hand down to her thigh and up under her skirt. She relaxed her legs slightly to let me go higher, and of course, instead of fingering a girl (which I had never done at that point) I found I was holding a stiff penis (which actually I had done before).

I could feel her wait for my reaction, but I scarcely reacted at all. I was too horny to do anything but keep going. And anyway, I'd done this before, with a man I mean, just not with one who was dressed like a woman.

After a pause, she began using her fingers to bring up spunk on my cock, then spread it around with her hand. Then, her hand still slimy, she gently squeezed my balls. She pressed her wet sticky hand on my thigh and it took me a moment to realise she wanted my legs wider apart. I complied, and a slimy finger slid down under my balls, gently stroking, and then going further down and under, and I felt a gentle prodding, slick but firm, as her finger probed my anus.

I know I gurgled and gasped and she must have decided I was going to come, because she bowed down over my cock and took me in her mouth. At the same moment she slid her greasy finger right up my anus. I arched myself - so hard that I actually later had a tender muscle in my back - and I came like a train in her mouth.

I thought I would lie in a trance forever, but in fact I had to get up straight away and take a piss. I bounded up stairs in the nude and while I was peeing I could feel my anus tingling from her finger, and by the time I went back down to the basement, with a couple of drinks, I was semi-stiff again.

We had our drinks, sitting almost in the dark, me completely nude, her now in bra and pants. We talked, mainly about sex of course, and she patted my lap to see if I was hard - I was - and after I'd finished my drink I snuggled in beside her and put my hand on her prick. I pulled her pants aside and brought up spunk, and gently masturbated her.

She asked me more questions about what I'd done and I realised she wanted me to tell her stories, so I told her about being propositioned and about this series of sessions I'd had. She listened, rapt, while I masturbated her, and then I felt her hand putting a small amount of pressure on the back of my head, and she guided my mouth down to her stiff cock, covered with a slippery coating of the liquid that oozed from the tip. Not all that big, but bigger than mine.

I set up to do her properly. I know this sounds sleazy, but I'd actually been given instruction in how to do this - how to please a man oral, I mean - by this man I'd done a few times, and I brought my expertise to bear.

I had her sit on the sofa but with an extra cushion under her so she was higher up. I positioned two chairs for her to put her feet up onto as she sat there, so her legs were up and fairly wide apart. I put another cushion on the floor in front of her and I knelt on it in the nude between her legs. If I sat back on my haunches my face was about level with her balls. If I knelt up, I could bow down over her penis and take it in my mouth.

Sitting there with her legs positioned wide apart and her stiff penis waving in front of my face, I thought she must have been quite surprised at my competence in this area. But in fact she later told me that in her experience (which was very considerable, I think) quite a few young people had been trained, as it were, in this skill.

I slobbered on her penis and then I put her fist onto her penis and had her wank herself while I mouthed her balls and licked in her crack. (I knew that a part of me would later feel shame and remorse for doing these things - I'd experienced it every time I'd done the man I mentioned earlier. But there was something deeply thrilling for me in serving someone older like this, performing such subservient acts for them, that for the duration of a session all thoughts of decency would be very far from my mind.)

I got some spunk on my finger and worked it up her anus and gently frigged her while she wanked herself, and we talked about what turned us on. When I felt her anus begin to clench on my finger I knelt up and bowed down over her slimy penis so she came in my mouth, groaning really loud and grinding her anus on my finger.

We didn't wake up until it was morning.

We got together a couple more times, but I don't think I was really her cup of tea - she wanted to be in a more submissive role, but I was more on the submissive side too.

But she introduced me to a couple of her friends, and one in particular really did me. She was much more butch, though still a lady at first glance, but she was bigger than me and she enjoyed pushing me around. Quite dominant, and I enjoyed that.

She used to get me in the nude and make me pose for her and talk to her about things I'd done, or I'd pretend I'd done, while she masturbated. She'd have me stand in front of her in the nude while she sat on the sofa, and she'd put vaseline in my anus. Then she'd get me to sit on her, facing her and straddling her so her penis was up against my bum. I would have to kiss her and slobber her on her mouth and her chest while she worked her stiff cock up me and I'd do her like that, working myself up and down and around on her until she came in my bum.

Her cock wasn't all that big, but it was big enough that it was an effort to let her sodomise me, and I used to pant and grunt while she was getting up me. There was no suggestion of our sessions being a two-way street - I was there to please her.

I was terrified someone might see us together, I was still leading a normal life, and we at some point just didn't see one another any more. We only had about five sessions, but they were some of the most intense and I ever had. I still get stiff remembering them.

At about this time I started to do better with girls, acquired a better social circle, as often happens in college, but I still did things, secret things, occasionally, for several years afterwards.

For example, I heard that one of the professors, a somewhat older man, was bi, and I couldn't shake the thought of being in the nude for him, and even though I was engaged to be married to a nice girl by then, I went and worked my way into the professor's little community (History) and found a way to have the right conversation with him, alone.

He liked games, as it turned out, and I had a series of sessions with him where I spent half the time tied up, sometimes in the nude, being sort of questioned, with 'punishments' for not being co-operative.

Bit weird, some of it, well, most of it really, but I enjoyed it all immensely.