My first anal experience
In my mid 20s i was getting a blow job from my girlfriend and she slid a finger in my ass. I had started watching gay porn before this, and fucking my own ass with a dildo, but this was the first time someone else played with my ass, Damn it felt good. SInce i have been rimmed and pegged many times, and have learned to cum from anal/prostate stimulation. God i love it!
Yes the first time for me was with the wife. She used her dildos on my ass. What an amazing feeling!
We never did get a strap on that would work. But she rubbed her pussy against my hole one night. We put a pillow under my hip to raise up my ass in the air. And then I reached around and pulled my cheeks apart. She mounted me and rubbed her pussy against my hole. I dont think Ive ever known her to have a bigger orgasm. She made my ass so wet. Then she rubbed her pussy juice into my hole. Still to this day its one of the best experiences I ever had with her
My anus and cheeks have been important parts of reaching an orgasm since I started to masturbate when I was 13. Between the ages of 11 and 18 I went to an all-boys school. At first, I found physical education and games an embarrassing ordeal. Our games teacher was a bully. He made us queue up naked outside the showers. 'Close up the queue' he would shout. Penises and bottoms touched. Was he demonstrating his authority or seeking sexual gratificaton? After reaching puberty, embarrassment turned into excitement. Several boys said how much they liked my big, round bum 'just like a woman's' and how much they would like to get their penises up it. Maybe, like me, they had been masturbating while looking at the nude magazines of that time, which showed a lot of ladies aged around 30-45 with ample bums and tits. I was flattered and excited by their attentions. I had already discovered that my cheeks and anus aroused me when I started to masturbate but this was the first situation where I found out that other boys were aroused too.
At the time, it appeared that he considered that shared nudity was part of a sporting activity; but surely he must have expected that developing penises pressing against classmates' bare bottoms would stimulate thoughts of sex. Often, he would watch us shower. He must have noticed our arousals. There was little opportunity for us to please ourselves after lessons in the gym, but after afternoon sports at the end of the school day, there was more time for touching and pleasing ourselves. Often I would go home with one or two friends to continue in my bedroom, or in summer, outdoors.
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