My lady friend made me a cock-slut.

The first girlfriend I had after I finally got a place of my own was a cougar. It was her that picked ME up in a bar one night. She wanted a toy boy, she said. I was glad to oblige. Never mind that she was older, she was hot as hell and the glint in her eye told me she was very much into sex. She was the one who helped me realize how much I like to get fucked up the bum.
I’d never given it any thought. Always considered my ass was just there and not anything to do with sex.
That first night she invited herself to my apartment. I quickly realized that she could teach me a lot. We were fucking in the missionary position when she reached down and grabbed both my buttocks. Grabbed them hard and held on.
I’d had other girlfriends and had been to bed with five other girls at that point, but we were all very inexperienced. The girls mostly just lay there and I would just pound away. No finesse and no inventiveness.
And never any girl that remotely could be considered as ‘taking the lead’.
So here was this one, grabbing and pulling on my ass and pulling me into her and it was fucking hot.
She started talking to me as well:
Fuck me. Yeah, I love it. Love your cock in my cunt.
Really dirty stuff.
And the dirty woman I was fucking was making me very excited.
I loved feeling her pulling on my ass.
Feeling her stretching apart my cheeks and dragging me into her.
I came very quickly. Calling out. Shuddering.
I told her how sexy she was and how I’d had the best cum ever.
She asked me was it OK when she was so verbal and I told her it was a big turn-on.
And she asked me what else I liked, and I told her that feeling her hands on my ass was sensational.
She told me to lay down on my front and began massaging my ass.
Nobody had hardly even touched my ass before and now it was getting a real going-over.
I was quickly discovering how erotic it is to have someone touch my backside.
I lifted my ass up off the bed slightly, because my cock was getting hard again.
She took it as a sign I wanted more.
I hadn’t thought about it, but immediately discovered that I liked it when she brushed her fingertips along my crack and grazed my asshole gently.
Moaned.
She asked if it was OK. I admitted that it was.
When she stopped moving up and down the crack and settled her fingertip against the opening of my anus….. it was electrifying.
I told her it felt fantastic. She asked me if I’d like her to press inside.
I said that was maybe a step beyond normal, but she argued that everything’s normal and I shouldn’t be so inhibited.
And then she pressed her finger into my ass, anyway.
Oh man, it felt so good.
She just went in and out a little and I began to move my ass up to meet her finger… it made my hard cock rub against the sheet.
She brought me close to getting off a second time.
Then she pressed in harder and it started to hurt. I squeaked and pulled away from her finger.
She stopped and told me we needed lubrication – which I didn’t have.
She said we could try again the next time we got together, if I wanted.
I definitely wanted, and told her so.
I was so excited to be trying something completely new to me.
She was definitely enjoying being some kind of sex-guru to this naive small-town boy.
We arranged for the next night, again at my apartment and I went to a drug store the next morning and bought KY jelly.