Taking the plunge. Got Pegged.

[storypost603]

After talking with my wife for a while about what turned me on. I told her last night was the night that I was getting pegged. She had told me she would do it and we got everything ready last night. After a very nice bubble bath for us with lots of caressing on both parts we got out and dressed for the evening. I really wanted to be dressed as a sissy so I put on a black bra, black panties, and black fishnet stockings. my wife has no problems with me dressing so we got the strap on adjusted to her and she used a wand massager on her self as I rubbed on her big cock sticking out. she told me to suck her cock and i started to take it in my mouth. after a little while she told me to take it deeper and I deep throated that big cock all the way to its balls. She then asked if I was ready to take it up my ass and i was more that ready. I lubed that big cock up and also lubed my bottom and got on all fours. She eased it in and was soon pumping away which felt great. I could not believe how good it felt even after reading all the posts on here and in the stories. I asked her to berry it balls deep to which she did. I could feel every thrust in my dick I guess it was hitting my prostrate but it felt so good. I rolled on my back and we fucked in that position for a little while but i liked it much better with my on all fours. We switched back to that position and that is when the fun really started. Once she was in again I told her to tear it up as I now had confidence that there was no pain even though I do like a little pain during sex like nipple pinch and biting. she started to slam in to me and I was pounding back to meet her thrust. Finally I could not go anymore as I was getting wore out. The night ended with me jerking off on her pussy and cleaning her pussy up with my tongue. Now that I have done it I really cant wait to do it again. I also have a lot of interest in a guy pounding my ass and cumming inside that has to be mind blowing. I see how guys want to be bottoms and think I would love to be a bottom i would have never thought that before last night.

 

[Escierto]

After talking with my wife for a while about what turned me on. I told her last night was the night that I was getting pegged. She had told me she would do it and we got everything ready last night. After a very nice bubble bath for us with lots of caressing on both parts we got out and dressed for the evening. I really wanted to be dressed as a sissy so I put on a black bra, black panties, and black fishnet stockings. my wife has no problems with me dressing so we got the strap on adjusted to her and she used a wand massager on her self as I rubbed on her big cock sticking out. she told me to suck her cock and i started to take it in my mouth. after a little while she told me to take it deeper and I deep throated that big cock all the way to its balls. She then asked if I was ready to take it up my ass and i was more that ready. I lubed that big cock up and also lubed my bottom and got on all fours. She eased it in and was soon pumping away which felt great. I could not believe how good it felt even after reading all the posts on here and in the stories. I asked her to berry it balls deep to which she did. I could feel every thrust in my dick I guess it was hitting my prostrate but it felt so good. I rolled on my back and we fucked in that position for a little while but i liked it much better with my on all fours. We switched back to that position and that is when the fun really started. Once she was in again I told her to tear it up as I now had confidence that there was no pain even though I do like a little pain during sex like nipple pinch and biting. she started to slam in to me and I was pounding back to meet her thrust. Finally I could not go anymore as I was getting wore out. The night ended with me jerking off on her pussy and cleaning her pussy up with my tongue. Now that I have done it I really cant wait to do it again. I also have a lot of interest in a guy pounding my ass and cumming inside that has to be mind blowing. I see how guys want to be bottoms and think I would love to be a bottom i would have never thought that before last night.

Yes, indeed. After my first fucking with a trans woman, I knew that I was a confirmed bottom after that. I never would have thought that I would be satisfied just being fucked and sucking my girlfriend’s big cock.

 

[OlderBtm4U]

Happy for you storypost.

 

[Crios]

After talking with my wife for a while about what turned me on. I told her last night was the night that I was getting pegged. She had told me she would do it and we got everything ready last night. After a very nice bubble bath for us with lots of caressing on both parts we got out and dressed for the evening. I really wanted to be dressed as a sissy so I put on a black bra, black panties, and black fishnet stockings. my wife has no problems with me dressing so we got the strap on adjusted to her and she used a wand massager on her self as I rubbed on her big cock sticking out. she told me to suck her cock and i started to take it in my mouth. after a little while she told me to take it deeper and I deep throated that big cock all the way to its balls. She then asked if I was ready to take it up my ass and i was more that ready. I lubed that big cock up and also lubed my bottom and got on all fours. She eased it in and was soon pumping away which felt great. I could not believe how good it felt even after reading all the posts on here and in the stories. I asked her to berry it balls deep to which she did. I could feel every thrust in my dick I guess it was hitting my prostrate but it felt so good. I rolled on my back and we fucked in that position for a little while but i liked it much better with my on all fours. We switched back to that position and that is when the fun really started. Once she was in again I told her to tear it up as I now had confidence that there was no pain even though I do like a little pain during sex like nipple pinch and biting. she started to slam in to me and I was pounding back to meet her thrust. Finally I could not go anymore as I was getting wore out. The night ended with me jerking off on her pussy and cleaning her pussy up with my tongue. Now that I have done it I really cant wait to do it again. I also have a lot of interest in a guy pounding my ass and cumming inside that has to be mind blowing. I see how guys want to be bottoms and think I would love to be a bottom i would have never thought that before last night.

There's nothing like that first time being pegged! My wife's knees only allow her minimal movement so we usually do it while I'm bent over the bed and she's standing behind me. For my first time, however, we tried that position for a bit until she got tired. I had her lay down on the bed and I mounted her cowgirl (or is it cowgurl? LOL!). I started to ride her while stroking my cock. I think she was surprised that I was moaning and whining like a girl. Even tho my cock didn't get hard, the cock in my boi pussy and my stroking caused me to cum with a force I'd never had before. Shot over her head and got some in her hair. I was screaming!

I'm older too so can't keep up that position for long so we don't do it much. My favorite position is to have one knee on the edge of the bed and the other foot on the floor at the end of the bed. She fucks me from behind. She gets great penetration that way.

If I'm on my back on the edge of the bed, she'll stroke me. She knows I love having my nipples pinched (and bit) so sometimes she'll rake a fingernail across one nipple while stroking me. Cum pretty hard that way!

 

[Flyover3]

After talking with my wife for a while about what turned me on. I told her last night was the night that I was getting pegged. She had told me she would do it and we got everything ready last night. After a very nice bubble bath for us with lots of caressing on both parts we got out and dressed for the evening. I really wanted to be dressed as a sissy so I put on a black bra, black panties, and black fishnet stockings. my wife has no problems with me dressing so we got the strap on adjusted to her and she used a wand massager on her self as I rubbed on her big cock sticking out. she told me to suck her cock and i started to take it in my mouth. after a little while she told me to take it deeper and I deep throated that big cock all the way to its balls. She then asked if I was ready to take it up my ass and i was more that ready. I lubed that big cock up and also lubed my bottom and got on all fours. She eased it in and was soon pumping away which felt great. I could not believe how good it felt even after reading all the posts on here and in the stories. I asked her to berry it balls deep to which she did. I could feel every thrust in my dick I guess it was hitting my prostrate but it felt so good. I rolled on my back and we fucked in that position for a little while but i liked it much better with my on all fours. We switched back to that position and that is when the fun really started. Once she was in again I told her to tear it up as I now had confidence that there was no pain even though I do like a little pain during sex like nipple pinch and biting. she started to slam in to me and I was pounding back to meet her thrust. Finally I could not go anymore as I was getting wore out. The night ended with me jerking off on her pussy and cleaning her pussy up with my tongue. Now that I have done it I really cant wait to do it again. I also have a lot of interest in a guy pounding my ass and cumming inside that has to be mind blowing. I see how guys want to be bottoms and think I would love to be a bottom i would have never thought that before last night.

Did you feel feminine with her cock inside you ? Did she fuck you again? We need more details.

 

[Escierto]

Did you feel feminine with her cock inside you ? Did she fuck you again? We need more details.

Lol, it is difficult not to feel a little feminine when you have a cock in your ass, especially when it’s a real cock! It’s probably the only time my girlfriend feels masculine as well.

 

[saintcero]

Lol, it is difficult not to feel a little feminine when you have a cock in your ass, especially when it’s a real cock! It’s probably the only time my girlfriend feels masculine as well.

Feminine and submissive do get enter-twined and then the words “breed me” slip out of your mouth

 

[Escierto]

Feminine and submissive do get enter-twined and then the words “breed me” slip out of your mouth

Unknown to each of us, we both fantasized that she was making me pregnant with her sperm as she cums. It wasn’t until I confessed that she admitted that she had the same fantasy

 

[saintcero]

Unknown to each of us, we both fantasized that she was making me pregnant with her sperm as she cums. It wasn’t until I confessed that she admitted that she had the same fantasy

Does she plug you afterwards to retain sperm or will her seed run down your leg

 

[Escierto]

Does she plug you afterwards to retain sperm or will her seed run down your leg

It seems strange but she gets her cum so deep inside that I never see any evidence of it leaking out. She does have a big cock and apparently the colon can absorb liquid so maybe I am absorbing her cum. I like to think so anyway

 

[storypost603]

Did you feel feminine with her cock inside you ? Did she fuck you again? We need more details.

well it has not happened again as of yet. I am not surprised as she seems to only get in the mood about every 3 months. I was caught in the moment and was just enjoying the feeling of what was happening and it was everything I hoped it would be. I do want it to happen again but only time will tell if she does it again. Now if I could find a man to do it that would be even better.

 

[Uncut1969]

Had a tongue and finger in my ass at I enjoyed a lot . I would love to experience a nice pegging !

 

[cdstefi]

Even tho my cock didn't get hard, the cock in my boi pussy and my stroking caused me to cum with a force I'd never had before. Shot over her head and got some in her hair.

I couldn't get hard the first couple of times and didn't cum either, in fact the first time I think I was in subspace and could barely stand afterward.

I did get the hang of relaxing and enjoying it fairly quickly, and became able to maintain an erection and masturbate or have her wank me to a full on orgasm, and like you, riding cowgirl and ejaculating all over her while having my ass fucked is just stupendously erotic.

 

[Male4Strapon]

Congrats on your first of hopefully many peggings.
It really is something every man should try at least once in their life. If done right, it will be the most mind blowing orgasm(s) of your life. I put the s in parentheses because you can have multiple orgasms. Three is my record but i have only been able to do it when I am riding, probably because i am in complete control of the speed, depth and exact spot the dildo hits me. It's incredible and her reaction is exciting.

 

[kccasey]

well it has not happened again as of yet. I am not surprised as she seems to only get in the mood about every 3 months. I was caught in the moment and was just enjoying the feeling of what was happening and it was everything I hoped it would be. I do want it to happen again but only time will tell if she does it again. Now if I could find a man to do it that would be even better.

I have the same problem. She does not want to do me often enough for me. I need to find a male lover, who is horny all the time like me

 

[Male4Strapon]

well it has not happened again as of yet. I am not surprised as she seems to only get in the mood about every 3 months. I was caught in the moment and was just enjoying the feeling of what was happening and it was everything I hoped it would be. I do want it to happen again but only time will tell if she does it again. Now if I could find a man to do it that would be even better.

Be careful not to be too enthusiastic for repeats.
My wife has told me part of the reason she won't peg me any more is that I was becoming obsessed with it which had her questioning my sexual preferences.
It's too long of a story but I think it's a bullshit excuse however she is right that I am obsessed, but the lack of it is what has made me obsessed. I think about it all the time because of the very fact that we don't partake in pegging any more.

But my point is..... logical or not, don't give her reason to believe this.

 

[storypost603]

Be careful not to be too enthusiastic for repeats.
My wife has told me part of the reason she won't peg me any more is that I was becoming obsessed with it which had her questioning my sexual preferences.
It's too long of a story but I think it's a bullshit excuse however she is right that I am obsessed, but the lack of it is what has made me obsessed. I think about it all the time because of the very fact that we don't partake in pegging any more.

But my point is..... logical or not, don't give her reason to believe this.

I understand but I also want to feel what is like with a guy at least once.

 

[TallOne]

There's nothing like that first time being pegged! My wife's knees only allow her minimal movement so we usually do it while I'm bent over the bed and she's standing behind me. For my first time, however, we tried that position for a bit until she got tired. I had her lay down on the bed and I mounted her cowgirl (or is it cowgurl? LOL!). I started to ride her while stroking my cock. I think she was surprised that I was moaning and whining like a girl. Even tho my cock didn't get hard, the cock in my boi pussy and my stroking caused me to cum with a force I'd never had before. Shot over her head and got some in her hair. I was screaming!

I'm older too so can't keep up that position for long so we don't do it much. My favorite position is to have one knee on the edge of the bed and the other foot on the floor at the end of the bed. She fucks me from behind. She gets great penetration that way.

If I'm on my back on the edge of the bed, she'll stroke me. She knows I love having my nipples pinched (and bit) so sometimes she'll rake a fingernail across one nipple while stroking me. Cum pretty hard that way!

Wife and I have a big height differential which makes a lot of positions challenging/tiring. The sex swing we got has been one of our best purchases. Can adjust for either her or I to be in the swing and the fucker can actually just stand there and rock the swing.

 

[Crios]

Wife and I have a big height differential which makes a lot of positions challenging/tiring. The sex swing we got has been one of our best purchases. Can adjust for either her or I to be in the swing and the fucker can actually just stand there and rock the swing.

That'd be awesome! I've tried to talk the wife into getting a swing but no luck there.

 

[ILikeIt]

The first time we did it she used a long dildo and squeezed one end between her legs. We both liked it so I bought her a strap-on. We've done it in many positions but she has a favourite. She lays on her back I straddle her with my back toward her and sit on her cock. I'll lean forward with my hands on the bed between her legs supporting my body wieght. I'll rock back and forth and ride the full length of her cock. She likes this position because she has a great view of her cock sliding in and out of me. She told me she likes seeing my pink ring flex back and forth as her cock pushes it in then pulls it out.

 

[Spongo]

I wanted to be pegged but dared instead to get the real thing….

 

[Escierto]

I wanted to be pegged but dared instead to get the real thing….

Ain’t nothing like the real thing.