What was your first time receiving anal like?

Not tense,right conditions, it could ease right in. Not her ass, mine. I had to show her how great it felt before she was ready to graduate. Doing it wrong could be the end of it.
Patience and Practice = enjoyable penetation , incredible feelings and mind blowing orgams.For Both Partners

 

It hurt a little at first, but after pain was gone, I had the most mind blowing orgasm I had had to that point. I also produced the most cum I had to that point. The overall feeling was so good. I felt it was more sensual, natural than sex with my ex-wife. In short, I felt more like a real man.

 

I love the theory of it, but the reality can be unpleasant.
First time I tried it was as apart of a group of schoolfriends, too young to know what we were doing. My mate had a huge cock and tried to put it in dry, but it hurt too much. Mine was smaller and I got it into him all the way but he wouldn't let me ride him or cum in him. First time as an adult I was 40, met a guy off the Net and went to his flat, he screwed me, came in me and I never felt a thing. He must have been good at the foreplay. I've done it with men since and some are good, some are too rough and very painful, but only once have I had what I'd call pleasure, when I almost came. The rest of the time, after the initial pain of entry, there was just thumping off my buttocks and no real feeling inside me.
I've done it with girlfriends and other men, but it's different whe you're the one putting it in.

 

I've been playing with my butt since I started masturbating just a finger or two.
so the first time my wife tried randomly slipping her finger in, she was surprised at how little resistance there was.
after realizing she didn't have a problem playing with manhole the toy collection started,
butt plugs,
anal beads,
strap-ons,
and she would pegg me a couple of times a year over time it became more frequent,
and for the last 5 years, I have been the only one on the receiving end of penetration.
I just wish it was more often. I would love to be taking it a few times a week.

 

It hurt a little at first, but afterwards it felt really good. Before that, he fingered me properly, it felt good as he stretched my muscles and I felt him penetrate.

 

My first time hurt like hell, i was only 12 years old and i use to fool around with the kid down the street and one time he asked if he could stick it in my butt, i said sure. With both of us being inexperienced he jammed it in dry and his dick was thick. I can still remember the pain to this day. He just stood there laughing.

 

My first time was just a little awkward. He dident really know what he was doing and just went for it. It wasent exactly painful but felt weird. And he dident last more than about 30 seconds so I never got to relax and actually enjoy it

 

:-( well he miss out!!

 

It felt awkward and faintly good, but then I got the hang of it.

 

My first time was painful he was 12 inches long and 3 inches around but after a few pumps it felt so good and even better when he shoot his load inside of my ass . And he didn’t stope he filled my ass up real good it took all night but he did it and my ass was hurting for a few day’s after then we did it again it hurt so good

 

It wasamazing, he wasn't to big and I was really into the moment, once he eased through the second sphincter wow, then knowing he blew inside me was amazing. Later year taking a long thick cock was next level amazing.

 

I love the feeling of a cock inside my ass . And I love the feeling when he shoots his load inside of my ass.

 

Attempted it for the very first time with a female ( kinkbuddy) who is visting from overseas. She has always wanted to fuck a guy with a strap on but never found any volunteers ( she confessed she hadnt really tried that hard because she (like myself) likes to keep her more kinky sexual fantasies and practices generally private.
She had no inhibitions about bringing it up with me and because we have been sharing our little sex secrets with each other for a while now she was pretty certain I was a possible candidate to aid and abet fulfilling her fantasy.
She absolutely knows about my tiny penis and rampant sph fetish and I had confessed myself that I had often fantasized about this particular type of activity as well as being fucked by a guy in front of a girl. ( kind of a bit bi by default because of the sph kicks it gives me)
On Saturday afternoon she went shopping for the necessary implement and as I had expressed no reservations about how big it was ( actually I did suggest rather largish to further enhance my sph thing)
However when it got down to actually getting into it on Saturday night I got a bit of the jitters about it as it looked frighteningly big ( even though it was about average size) We tried loosening up my hole with fingers and plenty of lube but I kind of couldnt go through with it. Disappointing but we decided on Monday we would go to a sex shop togethef and find something more suited for a beginner and maybe work up to the strap. We shall see. ( believe it or not I have actually never been in a sex shop before so that has given me a bit of stage fright but the potential sex kicks will get me past my timidity. ) I have to say though I am hoping the shop assistant is a sexy maneater type whom I coukd get some veiled sph like kicks from ( fantasy only but I have thought of wearing a pair of thin track pants with no underwear so if I get an erection while in the shop my tiny cock will be somewhat apparent - better yet lycra ones which do not leave much to the imagination when it comes to the size of your junk - dont have ny anyway - but this is just a fantasy scenario anyway even though the thought of being 'embarrassingly' exposed in this manner is very arousing right now.

 

Very enjoyable.

 

My only experience is with my wife doing me with a strapon and I loved it! Very addictive lol

 

Same here and the wife loves taking total control while wearing it.

 

I used plenty of lube and the guy was very gentle. It did hurt a little at first but I got extremely excited and the pleasure overcame any pain.