I was at university when I hooked up with Jenny. She was tall and thin with long blond hair. She was younger but still taught me a thing or two. I'd had two previous girlfriends, but they were nothing like her.
I remember the first time we fucked, she sat on my lap and started riding my cock. She was completely using me; she was wild. She put her fingernails in my shoulders and as she got more carried away, she dug them deeper, breaking the skin as I found out later. I remember it hurting a little, but I was so turned on with being fucked like that. She continued until she came, like she'd never before she said. Over the next few days, I had numerous healing cuts to remind me of that night.
A couple of weeks later she bought poppers so we could share the throbbing and our hearts racing when we fucked.
After a few months while chatting, she was sheepishly trying to tell me something. This wasn't really like her. It took several attempts, and I kept saying to her to just tell me, I won't mind. She finally said she wanted me to fuck her in the arse and then covered her eyes.
She'd had one previous boyfriend, older than me and from back home. He'd obviously had his wicked way with this teen's arsehole before.
It happened a few days later. We came home from a night out, both of us really horny. I think that was the time we'd seen a couple going to fuck in the toilets and we went to listen.
We weren't prepared at all and in the moment decided moisturiser was the best substitute for lube. I fucked her pussy from behind while I started to rub her anus with a thumb full from the jar. I slowly pushed the pad of my thumb opening her star. She was liking both my cock and thumb. I put more moisturiser inside her arse and pushed my thumb into it.
Her anus was tight, and I concentrated on just fucking her for a while. I started to pull on her anus trying to stretch her ring. I pushed further into her arse and moved my thumb in and out and in all directions trying to loosen her up. I was also getting and pushing more cream inside her until I could easily move my thumb in and out up as far as it could go.
It was time to give my dick a go. I pulled my foreskin back and rubbed cream over it. I pressed it against her anus, and it didn't feel like it was going to go in even after a push. I told her to bear down on my cock. She pushed back and then I could feel her anus opening. The head of my dick very slowly entered her, and we stopped when it had. We paused for a moment and I remember thinking it could really hurt me if she contracted.
I pushed inside her a little and she put a hand on my leg. I pushed two fingers inside her cunt and played with her clit with the wetness. I pushed inside with my cock a bit more and could feel it from inside her cunt on the back wall. I could move in and out now and it slowly got easier as I built a steady rhythm. I could feel her anus around my shaft and all of my dick being gripped.
I told her, “It feels so fucking tight on my cock."
She said she could feel it tight too. I was fucking her now. I'll always remember feeling my dick with my fingers from her cunt as it moved in and out. She groaned as I fucked her pushing my whole length in. I moved my fingers to her clit and started to fuck her hard. I could feel my balls slap at her pussy. She was groaning and panting. I couldn't believe I was pounding her like this. I told her, "I want to cum so far up your fucking little arse,"
She replied, "Fill me deep now." I was gone. I pushed all the way in and hard up against her and shot my load. My cock pulsed and she said she could feel it deep inside her.
Jenny and I split up after a couple of years and we lost touch but even now at fifty, I still remember this episode vividly.
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