What was your first time receiving anal like?

Over the long weekend I enjoyed a whole new experience. I wasnt very certain the fantasy would become a reality or if it did whether it would live up to the imagined experience. I have been totally motivated by the potential sph thrill of this brand new exploration but a bit trepidacious at the same time. Without going into broader detail here I very much enjoyed an unexpected foursome with my visiting female kink pal, a bisexual acquaintance and his girlfriend. The major new experience for me was doing anal for the first time and I was the bottom ( note I have never interacted with another guy except as a cuck voyeur since I was much younger and that amounted to the other guy back then rubbing his cock against my tiny penis while I was wearing a girls bikini bottoms)
In this foursome beyond any previous multiple players action I have engaged in I was fucked by another guy. The absolute thrill for me however was that two women watched me being dominated in this manner by a much better endowed guy. My penis is tiny but it never felt so small as it jiggled about. The sph kick was so massive I came without anyone touching my little dick.

 

that sounds like it was one hot scene

 

That was quite the experience! I wish I had a friend like that! My wife has an Handsome gay friend. He could have me anytime, But unfortunately, he is a friend of my wife’s, and Is in a committed relationship.
my wife knows about my hs/college SB from decades ago,. When I first confessed, she was somewhat surprised. Overtime she would ask questions, and we started watching some bi/gay porn. it really turned her on. we started having anal, which she loved. Turn about his fair play, so she started pegging me. We loved it! The role reversal was amazing. She walked out of the bathroom wearing her strap on she took control. She’d walk right up to me and shove it in my face and tell me to suck it. Then she would bend me over, lube me up, and push inside of me. All the time she kept saying I bet a real cock would feel better! All I could do was groan. Sometimes she was more gentle, and other times she just f*cked me. Whether I was stroking myself, or she was doing a wrap around, when I was getting close, she would say she was coming in me. That always set me off!
BTW…… did you ever tell your wife? Have you had a repeat?

 

I am still wanking over it and definitely,want to do something similar in the very near future. I have already suggested to the couple who were involved that I am up for a threesome and I dont even need to fuck the girl involved but just watching them and then her watching him fucking me again would hit the spot. ( I want to put it past them that it would be great if they found another guy, girl or couple to be involved but that might be a bit too ambitious) I want to try the sucking a cock thing but I promised my sex play buddy Carolyn that I would wait until she is involved)

 

The wife doesn't know. But she knows I like watching gay porn and I've admitted to liking to watch men masturbating and shooting their load on X Videos etc. Like you, I love my wife to peg me using a strap on and really big dildos. We have a huge selection of sex toys including vibes, dildos and male masturbation toys. She loves to watch me masturbating and she seems to know when I'm on the verge of cumming because she put my cock into her mouth and let me cum. She always swallows the lot. I've just masturbated after reading your story. I love to see videos of women pegging a guy. Many years ago I had several male friends and we'd sometimes end up masturbatingvtogether and sometimes we'd suck each others cocks. I always swallowed their cum. Recently though, I have to do with swallowing my own.

 

My neighbour said it was the first time for her in a park keepers shed in the park I pulled down her panties bent her over a bench rubbed her clit with the head of my cock and then I penetrated her ass. She said it felt thick inside her I stretched her andher parents went away for the weekend and I slept with her and holding her blonde hair while doggy fucking her ass was a wonderful feeling she said

 

The first time I fucked my wife's ass, I pretty much let her control the speed as I penetrated her. In a short while, I was able to work up speed until I came in her. After that, anal sex became a regular thing for us. For my first time receiving, it was a little awkward and hurt at first, but was fantastic overall. I was hooked on bottoming.

 

I dated a good looking Indian girl we went to see a movie there wasn't many people watching we sat at the back and she put her across both our laps and undone the zip feeling for my cock. I began to get a hard on it was a waste of time watching the movie so we went back to her basement flat. Her sofa was too small so ended up on her bed she said be gentle with me because your very big she was enjoying me fucking her until I started to doggy fuck her ass but she was screaming. I of course i stopped she said it was the first time that she was fucked in the ass. I dated her a couple of times more and I lubed up it was better but she never felt comfortable having a huge cock in her ass

 

A week later I got a text from her sister we met at our local bar she was curious to find our big my cock is. I said come back to my pad and you can judge for yourself, she was wearing shorts same as me. We got back to my pad I dropped down my shorts she was amazed and said you are so big I said you can make it bigger. I duly gave her huge fucking

 

Prison?

 

No.

 

Sorry to hear that happened to you!