First Anal Sex experience

An older female introduced me to giving and receiving. Fingers, tongue and eventually a small bullet vibrator on my ass. Curiosity made me wonder how it would feel to take a real cock and I had a willing FWB who took my ass for the first time. I still occasionally enjoy being penetrated.
 
I had a finger in my ass a number of times, but never more than that. One day, my GF told me after I had fucked her in the ass that she wanted to fuck me with a strap on. The next meeting, she set up a camera and fucked me mercilessly. No prep, no fingers first. Just me on all fours getting it up the ass hard. It hurt so good!
 
I had a finger in my ass a number of times, but never more than that. One day, my GF told me after I had fucked her in the ass that she wanted to fuck me with a strap on. The next meeting, she set up a camera and fucked me mercilessly. No prep, no fingers first. Just me on all fours getting it up the ass hard. It hurt so good!
That had to be amazing! ❤️❤️❤️❤️
 
My wife introduced all things anal to me. Blew me away.

Her statement to me was - she was not going to have normal intercourse until marriage, that left anal. I let her know I have no experience with anal, none whatsoever. Her next proclamation scared me a bit, saying if a guy wanted her sexually in any manner, he better be willing to go through the same things she goes through. What did that even mean?

She mentioned it's best to know how to do it well from start to finish and explained her process of cleaning well and staying prepared for anal, then how to take a finger, two, more. Lube, lube, lube, so much lube. She prefers coconut oil. I wish I could get her to write it out, the way she presented everything was crazy hot. Next thing I know I am giving it a go.

Coming out of the shower after following her input, she pounced me. Who knew oral anal can get you do give into almost anything? Bent over the bathroom counter she did things to me that I had never heard of. Needless to say, I was hooked. I let that gal teach me everything she wanted.

So - Take everything one step at a time, take it slow, prepare well and go with the flow. You will know when to increase more. She taught me well and it is a very normal but still to us very kinky part of our sex life. Having orgasms in multiple succession in the same manner as her was the game changer. Why in the world settle for only one and done?
What a wife❤️❤️❤️❤️❤️
 
  • My first experience solo was at an indecent age.
  • My first with another person (other than some caressing and a little fingering):
    • Giving cock: I was 19, she was younger
    • Receiving intesive finger-fucking: I was 22, she was younger
    • Receiving a strap-on (wife): i was 35-ish
    • Receiving cock: I was 45-ish
Pretty slow starter. Marriage slowed things down, otherwise I'd have been a hardcore slut by 25 or so. God(dess) knows, I had ample opportunity before I was 20. I still don't know what I was waiting for.

Ummm, wait, what was the question?
 
I had been playing with anal toys fir a while and was really wanting to experience the real thing. I met a guy via Craigslist and swapped oral a couple times. We decided that I would go to his house and fuck. He lived way out in the sticks and I was nervous because no one knew where I was and I was envisioning an ax murderer...lol

After I got there we chatted a bit which made me relaxe and we got down to business. I'll skip the foreplay description except that his cock was about 5" and wedge shipped. It was at least twice as thick at the base as the head and the head was nothing to scoff at.

I got on all fours at the edge if his bed so he could stand behind me. By the time he was all the way balls deep I was stretched wide and loving it. He was only able to pound me for a few minutes before he delivered his load where it belonged.

I wished he had lasted longer but it was still satisfying. This was about 15 years ago and I've been fucked many many times since!
Sounds like great experience. I found the comment about his cock being wedge shaped quite interesting. My wife had an ongoing affair with a work colleague. She mentioned one of the reasons she liked getting fucked by him, his cock is VERY wedge shaped. It really spread her pussy wide open and stimulated her clit. His cock is about the same length as mine, with a head like mine, but the base was twice as wide as the head. She rarely orgasms when I penetrate her, he made her cum nearly every time they fucked. They met up many times for about two years, I approved of this message…lol.
 
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