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 three 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."
"I love your cock in my cunt."
Really dirty stuff.
And the dirty woman I was fucking was making me very excited.
I was digging the feeling of 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 asked me to lie 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 up off the bed slightly, because my cock was getting hard again.
She took it as a sign I wanted more. It hadn't been my intention, but she became more adventurous and I quickly discovered that I liked it when she brushed her fingertips along my crack and grazed my asshole gently.
It made me moan involuntarily.
She asked if it was OK. It felt a bit gay to me and I was embarrassed to confess that it was more than OK. That I was really enjoying it.
Then she stopped moving up and down the crack and settled her fingertip against the opening of my asshole. 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 me, anyway.
Oh man, it felt so good.
She just went in and out a little and I began to move my butt up to meet her finger. It made my hard cock rub against the sheet.
That, and her finger, brought me close to getting off a second time.
But she pressed in harder, briefly, 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 and 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. I went to a drug store the next morning and bought KY jelly.
Remembering how tight my ass had felt on her finger and how it was uncomfortable when she pushed into me without lube, I bought the largest size they had.
It seemed as though everyone in the store was watching me at the checkout. They were judging me, I thought. I felt like some kind of pervert.
She came to my place early and with Chinese take-out.
Said we would be staying in all evening and she would show me some things it was time I knew.
I thought it was going to be all about her fingering my ass, but first she taught me cunnilingus.
I never went down on a girl before.
Loved it.
Loved when she showed me her clitoris and talked to me as I licked it and followed her instructions.
The taste of her pussy juices were heaven.
When she was close to cumming she held my head tight and pressed my face hard onto her cunt.
I could barely breathe but kept sucking on her clit.
It was hard like a nipple and I sucked like a hungry baby.
She came, and covered my cheeks and chin with juices.
Then she pulled me up to her and we kissed.
She was taking pleasure from tasting herself on my lips.
My hard cock just naturally slipped into her soaked pussy as we kissed and I fucked her until she came again, this time from my cock.
Her hands were not on my ass this time, she used them to hold her knees and keep her legs wide apart and in the air while I rammed my hard cock up her wet cunt, over and over.
She just wanted powerful thrusts in and out of her until it brought her off.
Her position was all about getting as much cock as possible up her twat.
She told me encouraging things, how she loved my fat cock. She said that my cock was big enough to stretch her pussy and she loved to feel so well filled.
When she reached her second orgasm and I felt all the hot fluid gush out onto my cock it made me cum too. She was flooding fluids out of her pussy onto my cock and I was pumping cum out of my cock and into her sopping cunt.
When we were done cumming into and onto each other, I rolled off her and we lay side by side catching our breath. Then she put her hand on my head and gently motioned me back down to her cunt. She wanted me to eat her out again. This time with her pussy full of my cum.
It was so far beyond anything I'd done before but I was turned on by the idea. I buried my face between her sexy thighs and clamped my mouth over her wet and swollen vulva. Sucking and tonguing her glorious pussy. Tasting her juices and my cum as they dribbled out of her and into my mouth. Swallowing. Her cum and my cum. Her hands were holding my head tightly against herself again and she quickly came for a third time.
I lifted my face from her lap and climbed back up the bed to lie along side her.
Her hand moved between her thighs, and I watched as she languidly stroked her clit.
After a little while of regaining our breath we both realized we were hungry.
We nuked the take-out food and ate it sitting on the bed, watching TV.
She told me I was already a much better lover than I had been and I should never stop trying to think of exciting things to do.
I replied that I'd been thinking about the exciting thing we'd started the previous night. She arched her eyebrows at me as if to say I was a bad boy. But her smile told me that she was keen to show me more in that department.
By the time our plates were empty I had another hard-on from thinking about what she might do with me.
I took our empty plates to the kitchen and when I returned to the bed I laid on my stomach so that my ass was up in the air.
She laughed at how keen I was to be penetrated.
I was a little embarrassed, but she'd already told me that in sex everything is cool. Nothing is outrageous. She'd told me to be honest about my desires. So here I was. Face down, ass up. Ready for her to show me a thing or two.
I pointed to the big container of lube on the bedside table. She laughed and wryly told me it would probably be enough for a couple of nights, at least. Then she opened it up and covered her fingers.
I didn't want to waste time getting to the point we'd stopped at the night before, so I reached behind myself and spread my ass cheeks.
Again she expressed surprise by how keen I was to get something up my bum. I guess I was too.
But the brief sensations she'd shown me already had created a craving for more.
She sensed my urgency and put her finger against my ass and immediately started pressing.
She told me to push out and, I when I did that, I felt her finger go into me easily.
