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First experience with anal...

Was back in college. My girlfriend of the time had borrowed a "Sensual Massage" book from one of her girlfriends and we were in bed watching TV and experimenting with the techniques of the book.

Both of us were covered in oil and she was lying on her stomach while I massaged her back and buttocks. I began reaching between her legs from behind, swiping up and down across her labia and up to her anus. After a while, when she had her legs spread and seemed relaxed, I slipped on oiled finger into her asshole and began to slowly pump it in and out. At first she seemed te3nse, but soon relaxed. After a few minutes of one finger I increased to two fingers and continued the in and out routine. I could feel her muscles relaxing more and after another few minutes increased the penetration to three fingers, and eventually to four fingers. She felt so totally relaxed I moved on to the next step, mounted her from behind and slipped my cock into her ass. No problems, no tensing. I began to pump into her while at the same time reaching around beneath her so i could massage he clit with my hand while fucking her ass. After some time we both had an enjoyable ending to the experiment. It wasn't something we pursued, but it was fun. The odd thing to me was the difference in feeling between vaginal and anal sex. Vaginally my cock would feel surrounded, touched all around, but anally the feeling was mostly that of the band of the sphincter tight around my cock with very little feeling anywhere else.
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Outdoorfreedom · 56-60, M
Thanks for sharing. Good memory.