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.
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 felt like everyone in the store was watching me at the checkout.
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. 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. 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.
I felt her cum drying on my cock and balls, cooling them.
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 seemed 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 tub of lube on the bedside table. She laughed. Told me it would be enough for a couple of nights, at least, 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.
Fuck, it felt so good.
I told her so.
Yeah baby, I know.
She knew? Well, of course. I hadn’t fucked her ass but I wan’t surprised that she knew all about it.
Her finger was going in and out of me and giving me unbelievable pleasure.
My cock was hard again. She asked me if I liked it. What a question.
I lifted my ass in time with her finger to let her know.
She asked if I wanted more and I said yes and said that she could keep doing ‘more’ until I said to stop.
She added another finger to the first and pressed into me again.
I figured out how to relax and let it be pure pleasure. That’s what it was.
Lying there, feeling nothing but these amazing sensations from my ass filling my whole body.
She could tell it was good for me. Told me I was a natural…. she’d done this with other men and they weren’t usually so receptive.
I didn’t know if I should be proud, but I was.
I told her she was giving me a fantastic feeling.
She said she had a surprise for me and pulled her fingers out of my ass. Got up and grabbed her bag. I watched as she pulled out a dildo and a leather harness.
She told me “I’m going to fuck you now” and stepped into the harness and pulled it up. There was a hole at the front and she posted the big dildo through it and then tightened it all up with buckles at the sides.
She stood at the side of the bed and I looked up and watched her rubbing lots of lube up the entire length of the sex-toy between her legs. Her hands went up and down the shaft like she was masturbating for me.
I wondered if I could take such a big dildo in my ass, but she didn’t ask me if it was OK to continue. And I didn’t tell her to stop.
She climbed up behind me and I looked back at her as she crammed more lube up my ass.
She told me to spread for her. I reached back. Grabbed my ass in my two hands and separated the cheeks so she could set the big dildo against my anus.
I felt her lower herself down onto me and the rubber cock entered my ass.
Heaven.
She kept a steady downward movement and the dildo went further and further up my ass.
Finally she was buried deep into me and she stopped there.
Leaned down and whispered in my ear.
Told me again that I was a natural.
Told me I loved it.
Told me I was a cock-slut now.
Told me she was my mistress.
And she began to fuck my ass.
In and out, fast and hard.
My cock was hard against the sheet below me and the thrusting movements of her hips as she pumped the big plastic cock into my ass over and over were causing me to rub myself off against the bed.
She lifted herself off me and pulled me to my knees by my hips.
Kept driving the dildo into me as she brought us to the new position.
Then she reached down and grabbed my stone-hard cock and started stroking it in time with her thrusts.
She told me to cum. Told me I must shoot my cum as she fucked me.
Bumping herself against my ass…
grinding her strap-on into my ass…
Squeezing and jerking my cock.
Cum for me, she ordered again.
She gripped my cock tight. So tight.
She jerked my cock faster. Pumped my ass faster.
I moaned and panted.
She was making me cum.
I was going to shoot onto the bed.
Cried out…..
Cumming. Oh, oh, cumming!
She quickly pulled us both upright. She was sitting on her heels. I was sitting on her lap. My ass was deeply impaled on her cock.
She pulled me down onto her and held on.
My ass was stretched impossibly wide.
I was loving it. It was making my orgasm intense.
She leaned me backwards slightly and my cum flew up and hit my face.
I parted my lips… catching some in my mouth.
She told me I was a dirty boy.
I was. I was her cock-slut cum-eating dirty boy.
That was the start of it.
We were together for several months until she broke up with me.
I was so into her fucking my ass that she wasn’t getting her cunt serviced properly any more, she said.
I’ve dated plenty of other girls since, but haven’t found another who will play the same games. They think it’s too freaky. I’ve learned not to ask, because I’ve missed out on too many fucks.
I have my own dildos. I fuck myself in the ass when I jerk off.
I’ve also met a nice older gentleman who appreciates my desire to take a cock in my ass.
It was weird the first time he fucked me.
A man. With his cock in my ass.
But he was so good. And so appreciative of my young ass. It’s very arousing to be complemented like that. To be told you are sexy by another man.
And being fucked by a man is better than being pegged.
When it’s a strap-on the woman doesn’t always know when it’s enough, but when you’re being fucked by a man, you both know: when his cum shoots out and fills your ass.
My man friend taught me about giving blow-jobs and swallowing his cum.
His cock is perfect. Long and straight and hard and thick.
It brings him pleasure standing over me while I kneel in front of him and suck his cock.
I love looking up at him as he shoots his cum into my willing mouth.
And he has introduced me to some of his friends. Sometimes they come to my apartment and take turns fucking me.
My neighbors have seen men entering my apartment and staying the night. Sometimes more than one at a time. I don’t care though.
I can’t get enough cock.