A few days back I was asked if I ever pegged a man and if it was fun. My answer was quite short with just two words:
Sure, awesome!
So now I got the request to write about it because some of you might like the story behind it.
The story
Once in Amsterdam I met a guy at a workshop we both joined. We talked a lot and had fun – nothing sexual – about 3 days. One night out in Amsterdam we both had some Tequila shots and cocktails and wine, so we ended up in my hotel room. Drunk, horny and later nude on the carpet doing nasty things. The next morning we looked at each other and smiled – we enjoyed it very much and decided to do this for the rest of the time being in Amsterdam.
Two days later we both met in my hotel room again and after some glasses of wine I wanted to surprise him with a nice outfit (stockings and such) but even before putting the things on a strap-on I bought in Amsterdam was falling out of my bag (still in its plastic box and never used). He looked at it and asked me things about it – is it yours?, do have lesbian sex?, and questions like that.
I told him about my relationship with a woman, the fun we have with strap-ons and the more I told him about the strap-on things the more interested he became in trying it. He was a normal guy, loving women, fucking women, staring at women – so totally normal.
I opened the box, put it on and played with it as if it was my cock. His eyes became bigger and bigger. By the count of three he was sitting nude on the bed, playing with his big cock and balls. By the moment I came closer to him he lay down on his back, he pulled his legs up and tried to show me his backdoor.
It was quite interesting for me to see a straight guy waiting for a cock up his butt. I used lots of lube as always, used up to three fingers to open him and then I started to use the strap-on. I took me 5 minutes to open him with the big black toy and another 5 minutes to put it all the way in – 24cm (9.4inch).
I was suprised. He was surprised. I enjoyed it. He enjoyed it.
30 minutes of fun for him with my strap-on up his butt until his relaxed(!) cock started to jerk off. A very HUGE load of his white manmilk came out of his cock – first fast and later slow. It was the biggest load of cum I saw until that time. About three or four times more than I knew it from any other man before.
It took about 10 minutes until his cock stopped jerking off – he slowly started to talk again and tried to describe the feeling of his penetration. I removed the strap-on while he was talking and enjoyed the look of his opened butt-hole and the amount of cum on his stomach and my bed.
I gave him about 30 minutes more to come back to reality, took a shower with him and ended on the coach talking with him about his first anal experience. Talking about it made us both really horny and we had fun the regular way – well the normal and anal way for me and in a second round anal for him again.
There are X things I learned that night for the rest of my life:
- never peg a man if you are hungry for cock
- always peg him after you enjoyed a good ride
- male butt-hole are more robust than female butt-holes
- happy-end-blowjobs after a nice pegging session are for girls that don’t like cum in their mouth – the guys are empty after that!
So, this was the story behind my first pegging session – with a man.
Thank you for your questions and feedback in advance.
I’m a straight man and never had a woman peg me with a strap on, but one used a smaller toy on me, and I also do this to myself sometimes. Gosh. Can’t wait to have this done to me. Go for it dudes, the orgasm is quite different from the “normal” orgasm, much longer, and somewhat more intense too. And if you think this hurts your manhood… just don’t read me, don’t read this blog, just go away. Too many women think so though :’(
Hi Sylvain,
thank you for sharing your thoughts and experience about this topic. Glad to see a straight man giving a pro on enjoying anal action. I wish you meet a girl in the future with a strap-on in her toy box for you.
May I ask you if your orgasms are like the one described in my post? Do you ejaculate a huge load, too and is your cock hard while enjoying a toy up your butt?
I’m so interested in this topic but not that many man allow me to “test” them. The men I pegged turned into cum machines and the most interesting part was that their cocks were not hard at all. Such a weird moment when a soft cock ejaculates.
Gabi.
Hi Gabi
Yes, my orgasm are quite as you describe, with some differences though: I do ejaculate a bigger load, but not that bigger, clearly not 10 minutes. I’m not as hard as I usually am but still quite hard. And I can confirm that it wasn’t too difficult to get the toy entirely in my butt. At least I think it was far easier for me than it seems to have been for my female partners on their first times. I do think toys are more enjoyable than fingers (I guess they stimulate the prostate better). But the toy I used was smaller than a strap on, maybe it explain things.
Don’t worry, I’m sure I’ll have the opportunity to be pegged pretty soon
cheers,
S.
So horny Gabi, I’ve yet to try this with my wife, one day I hope she’ll fuck me…
Have you asked her already? Or is it still an unspoken dream you have?
Hello, are you going to be posting any more english-language stuff?
Thanks
@Harold: Yes, of course. Starting again in 2012.
Hello, i thought i would reply to your colum here. i love being pegged by a woman. it only really happened one time, but it was great.. i can only imagine it feels like that for a woman to be slammed into over & over. the orgasm was long coming but i was on edge for a long time.. and i am hard at first, then it slacks off.. but she touches my penis or if i do, i get rock solid instantly.& when i cum, it was a guge load, then lots of smaller loads follow if she continues to minipulate me while jacking or sucking me while penitrating me with a toy. unfortinatly it didn’t happen often, and now not at all.. she has moved on.. but i will say that when toys are used on me i get a thurst for more & more depth & size. ,, .. also there was nothing like the feeling of being pegged my my wife & feeling her body on mine & seeing her & her huge boobs displayed for me to enjoy while she pounded me.. i only hope i can find another who is open & enjoys the pleasure time! thanks, Jeff