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By (user no longer on site) OP 36 weeks ago
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I've only had a few anal experiences and my favourite was difficult to choose.
The runner up was when my ex wife used a strap on with me. It was so empowering for her and I felt so good letting go and relaxing into the experience.
It was very much planned.
The best experience was planned. It was about8 years ago when I was on here as my crossdressing alter ego. I'd met a lovely dirty sexy girl off here who was very much into wanting to explore me as a girl.
So we planned a night where she came over early and got merry d*unk and dressed me up the most feminine I've ever been.
I was buzzing on the high of red wine and feeling super sexy.
We had wonderful naughty sex and she even introduced watersports (story for a different time)
Anyway we had just finished sex and she had tidied me up so I was looking good again. She looked me in the eyes and said I think you're ready.
I was not sure what she meant but after a quick conversation we agreed that we'd invite a guy over to fuck me. She found one pretty quick on here and we invited him round.
He arrived on time. An average height man with dark hair and dressed reasonable. He smelt good and had a wicked smile. She kissed him in front of me and and then I joined in.
We got him hard and sunk to my knees. His cock was long but not too thick. His precum filled my mouth quickly. We made our way up to the bedroom.
She had me lie on the bed as he striped.
Before I knew much about it. She was lubing my smooth prepared ass.
He entered me and fuck did it feel good. I groaned in pleasure and felt his hands on my back. He pulled his full length out and went again. Again. He stopped but I wanted more... I could hear them kissing over my shoulder... obviously distracted so I thought I'd help him out...I started thrusting back into him.
He moaned and then I felt him twitch. He came hard.
I felt the pulse through the condom and he sighed deeply. He pulled out and left quite quickly...I was left really unsatisfied despite feeling great about making him cum.
I turned to my girl and said I want more.
We found another guy within about 30 mins and he took another 20 to get there. So we used that time to freshen up.
He was a shorter man with a fat cock. It was about 5 inch long but great shape.
Similar routine when he arrived but he didn't wait to go upstairs.
He actually took the lead and pushed me back to the kitchen table.
Bent me over, pulled my panties to the side and slid his cock in... Fuck it streched me. I breathed hard to relax.
He was complimenting my ass and how good I felt.
My girl was cheering is both on while massaging his back.
I squeezed my ass and he slowed. I remember giggling as he said fuck you'll make me cum if you do that.
So I did it again and again. He took slow strokes...I was close. Before I knew it I was cumming in my panties and through onto the floor.
I could feel him close. So I pushed him back and spun round to my knees. Before he knew what was happening I was sucking him without his condom on.
He buckled and fired his load in my mouth.
I remember the salty taste mixed with smudged lipgloss.... Fuck it was hot. Xx |
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