I’ve always enjoyed a bit of anal play, and had wanted to get pegged for a while. I connected with a woman online, we met for a drink and then back to my place for some excellent but fairly vanilla sex.
After that night we kept texting, and got into our fantasies. She told me she was into receiving anal and I confessed that so was I – luckily she sounded really into the idea and even owned a strap on already.
Next time we arranged to meet she asked me if she should bring anything? I responded “wine?” and then quickly added “and your strap on…?” To which she responded with a 😈.
On the night she came over to mine, we shared that bottle of wine (a nice red), chatted a little, and then found ourselves making out on the sofa.
I suggested we move it to the bedroom and she said she’d meet me there. I assumed she just wanted to use the washroom, so I thought nothing of it and went to wait.
I was sitting on the edge of the bed when she came in, wearing a lacy black bra and panties, thigh highs, and a harness containing a realistic looking dildo!
I was a little surprised and probably looked it, but she took hold of the situation and asked me if I was going to suck it? I nodded yes and she stepped over to me, finding her dildo at just the right height for my seated mouth.
I took the dildo in my hand and started licking it, eventually wrapping my lips over it and starting to suck, shallow at first but getting deeper as she encouraged me.
Eventually I came up for air, and realized I was still dressed which felt a bit wrong. She helped me out of my clothes and then pulled off my boxers to reveal my cock, rock hard as I was so turned on from sucking hers. She knelt in front of me and took me in her mouth, her hand stroking my balls at first, then heading towards my ass. I handed her some lube and she slid a finger inside me while blowing me, which had me moaning in pleasure.
Next, she stopped sucking and really concentrated on my ass, adding more lube and another finger, then another. She asked if I was ready and I knew what was next – I said I was, and got on all fours with my ass in the air. She lined up her strap on and I felt her on the bed behind me.
She slid it into me slowly at first – just the head, then a pause, then easing into me inch by inch. It hurt a little at first but soon started to feel amazing. Once she had it all the way inside me she gripped my hips with her hands and started to fuck me – slowly at first but soon getting faster and harder.
I just buried my head in a pillow and moaned in pleasure, it felt amazing to be fucked like that. She told me later it felt super hot for her too.
After a while of this, she told me she wanted a cock inside her too. She’s pulled out, I turned over and lay on my back, and she pulled her panties to one side and got on top of me. Her pussy was soaking wet and I slid into her easily.
She was still wearing the strap on so I felt it bouncing on my stomach as she rode me. It didn’t take very long until we both had massive orgasms and lay next to each other recovering our breath.
After we’d recovered, we had a lot more fun together on that night – and others…
Source: reddit.com/r/gonewildstories/comments/p7qm4x/first_time_getting_pegged