Strap-on experiences

[randyspinster]

Being a switch, I love having roles reversed. I think taking turns being penetrated is hot and can be insanely intimate.

 

[Goldenfinger]

I think everyone should try it a few times. I think it has brought me and my wife closer and it has given me a different perspective.

 

[eroticspank]

A woman pegging you is a special event and its different from a tranny fucking you because you can see the woman’s excitement. She elated to have your ass and have the roles reversed

I think it is different for everyone. Some women are not turned on by it and worry about losing their partner to a man. If it is something new for your lady it is important that she understands your interest in it and how it can be pleasurable for her as well.

ES

 

[RickyBobby571]

Fantasy

This is my ultimate fantasy, I wish I could find a willing partner

 

[Wonderer67]

My wife and I have been building up to a pegging session for a couple of weeks. Our schedules have been tough and all sorts of things have come up. So we aimed for today.

We talked about it last night, and sort of planned our scene.

Miss Conduct (my wife) dressed me up in a garter and fishnets which I really love wearing. I don’t wear them too often so it really turned me on. Then she had me insert an aneros Maximus prostate massager. Then she had me prepare her favorite meal for dinner, Sheppards Pie. I was short two ingredients (poor planning) but she suggested I go to the grocery store with my pants over my buttplug, garter and stockings. It really turned me on!

Came back and finished up and it was time for fun. We scrolled through a few favorite threads here on the literotica forum, then switched to Pornhub and watched a bunch of hot pegging, prostate massage and femdom videos. She donned her strapon, a large 8.5”, thick dildo which is my favorite. She lay in bed and I sucked her “cock” for about 10 minutes. Then she ordered me to my knees and face fucked me. So hot!!

Then it was time for a prostate massage. Miss Conduct had me remove my prostate massager, then tied me down tight so I couldn’t move, face-down to really nice bench that we turned into a handy piece of bondage furniture (added in several eye bolts). I was basically spread Eagle face down. She gave me a fantastic prostate massage for about 10-15 minutes. I’ve been without an orgasm for about 3 weeks so I was hoping she would trigger a prostate ejaculation, but no luck. If felt great!

Then she was ready to bang me, she was doing a good job of dirty talking (not really her thing, but she’s a good sport). She got behind me and slowly, almost completely painlessly started to enter my ass. As she was going gingerly, I pushed my body back on the bench into her cock. Eventually we found a really good rhythm with her hovering behind me and me moving my body back and forth on the bench to get that cock into my asshole. I sped up till I was getting pounded quite hard. It felt great and I was having many prostate orgasms but no ejaculation. We fucked that way for about 20 minutes. I almost didn’t want it to end. It felt amazing!

We decided to change positions. She untied me and Uncuffed me. She sat on the end of the bench, while I straddled her huge cock. I got it in me and started riding it. It was so hot - I felt so close to her and we started kissing while i rode her cock. She was absolutely ramming her tongue down my throat which made me feel even more feminine and submissive. I had a string of strong prostate orgasms. After about five minutes of that, she lay down on the bench with her cock still in me, and i started riding her hard, looking at myself in the mirror taking her huge cock right in my ass.

And then it happened, I felt a prostate orgasm building and then I felt a little like I had to pee. I knew it was happening and I was so excited. I told Miss Conduct I was going to cum and to look up. A big wad of cum came out of my cock all over her stomach. It sort of shot but also oozed out at the same time. I finally had a hands free prostate cum! I kept riding since it felt so good and I hadn’t lost my mojo. About a minute later I had ANOTHER ejaculating hands free cum. More cum oozed and shot out all over Miss Conduct’s stomach. This time it was more like a traditional cum. I stayed on and rode for another few minutes hoping a third one would happen but it didn’t. I was totally spent.

Miss conduct had me luck my cum off her stomach and then clean her up and remove her strapon. I was in a daze I was so fucking happy and sexually satiated I could barely think.

Sorry for rambling on, but it was such an amazing experience- I got a hard ass pounding like I wanted, it was awesome anal and I’d had that elusive hands free cum I’d been trying to have again for years.

 

[Iwant2havefun]

My wife and I have been building up to a pegging session for a couple of weeks. Our schedules have been tough and all sorts of things have come up. So we aimed for today.

We talked about it last night, and sort of planned our scene.

Miss Conduct (my wife) dressed me up in a garter and fishnets which I really love wearing. I don’t wear them too often so it really turned me on. Then she had me insert an aneros Maximus prostate massager. Then she had me prepare her favorite meal for dinner, Sheppards Pie. I was short two ingredients (poor planning) but she suggested I go to the grocery store with my pants over my buttplug, garter and stockings. It really turned me on!

Came back and finished up and it was time for fun. We scrolled through a few favorite threads here on the literotica forum, then switched to Pornhub and watched a bunch of hot pegging, prostate massage and femdom videos. She donned her strapon, a large 8.5”, thick dildo which is my favorite. She lay in bed and I sucked her “cock” for about 10 minutes. Then she ordered me to my knees and face fucked me. So hot!!

Then it was time for a prostate massage. Miss Conduct had me remove my prostate massager, then tied me down tight so I couldn’t move, face-down to really nice bench that we turned into a handy piece of bondage furniture (added in several eye bolts). I was basically spread Eagle face down. She gave me a fantastic prostate massage for about 10-15 minutes. I’ve been without an orgasm for about 3 weeks so I was hoping she would trigger a prostate ejaculation, but no luck. If felt great!

Then she was ready to bang me, she was doing a good job of dirty talking (not really her thing, but she’s a good sport). She got behind me and slowly, almost completely painlessly started to enter my ass. As she was going gingerly, I pushed my body back on the bench into her cock. Eventually we found a really good rhythm with her hovering behind me and me moving my body back and forth on the bench to get that cock into my asshole. I sped up till I was getting pounded quite hard. It felt great and I was having many prostate orgasms but no ejaculation. We fucked that way for about 20 minutes. I almost didn’t want it to end. It felt amazing!

We decided to change positions. She untied me and Uncuffed me. She sat on the end of the bench, while I straddled her huge cock. I got it in me and started riding it. It was so hot - I felt so close to her and we started kissing while i rode her cock. She was absolutely ramming her tongue down my throat which made me feel even more feminine and submissive. I had a string of strong prostate orgasms. After about five minutes of that, she lay down on the bench with her cock still in me, and i started riding her hard, looking at myself in the mirror taking her huge cock right in my ass.

And then it happened, I felt a prostate orgasm building and then I felt a little like I had to pee. I knew it was happening and I was so excited. I told Miss Conduct I was going to cum and to look up. A big wad of cum came out of my cock all over her stomach. It sort of shot but also oozed out at the same time. I finally had a hands free prostate cum! I kept riding since it felt so good and I hadn’t lost my mojo. About a minute later I had ANOTHER ejaculating hands free cum. More cum oozed and shot out all over Miss Conduct’s stomach. This time it was more like a traditional cum. I stayed on and rode for another few minutes hoping a third one would happen but it didn’t. I was totally spent.

Miss conduct had me luck my cum off her stomach and then clean her up and remove her strapon. I was in a daze I was so fucking happy and sexually satiated I could barely think.

Sorry for rambling on, but it was such an amazing experience- I got a hard ass pounding like I wanted, it was awesome anal and I’d had that elusive hands free cum I’d been trying to have again for years.

an amazing story....so sensual and sexually satisfying.....i like "Miss Conduct" a lot!

 

[eroticspank]

an amazing story....so sensual and sexually satisfying.....i like "Miss Conduct" a lot!

Yes, I agree. That was a great story. That is what this thread is about, experiences.

ES

 

[tonyreid]

first time

My first strap on experience was astounding ! But even better was buying it . my then g/f now wife and I were in Brighton before we cam back to states , Went to a sex shop cant remember name but it was 3 story building . Any way we were up on 2 nd floor I think it was g/f was trying on strap on shouted for me to come in to changing room see what I thought Gets in there ant the girl helping her is on her knees stroking the strap on and when she see me she gave me a wink and licked the head of the strap on . She was very sexy and was wearing what looked like a 50s style dress stockings etc . Wish I could say more happened but unfortunately I was never that lucky ! Still sticks in my mind though

 

[eroticspank]

My first strap on experience was astounding ! But even better was buying it . my then g/f now wife and I were in Brighton before we cam back to states , Went to a sex shop cant remember name but it was 3 story building . Any way we were up on 2 nd floor I think it was g/f was trying on strap on shouted for me to come in to changing room see what I thought Gets in there ant the girl helping her is on her knees stroking the strap on and when she see me she gave me a wink and licked the head of the strap on . She was very sexy and was wearing what looked like a 50s style dress stockings etc . Wish I could say more happened but unfortunately I was never that lucky ! Still sticks in my mind though

Nice! So did your wife have you get on your knees in front of her when she put on the strapon at home? Or was the memory of the visit to the store a big part of your foreplay?

ES

 

[Crios]

We'd been doing butt play (fingers, plugs, etc.) for a couple of years. When shopping on LoveHoney for some new toys for her, I came out and just asked her: would she be willing to fuck me with a strap-on? She said "I don't know.." (which is her response to just about everything where she has to make a decision). So, I suggested we order something. Got one with a 5 3/4 inch cock and one 8 1/2. The 8 1/2" one could be used as a penis extender also but we've never used it for anything but.

First time was heaven! Used a butt plug to loosen up. We have matching metal plugs with heart shaped "jewels" in the ends. Mine's larger .
I bent over the bed and she just slipped in me. Didn't cum from the fucking but sure was hot.

Since then we've done "missionary," cowgirl and one where I have one knee on the end of the bed and the other foot on the floor.

The cowgirl was awesome as I came while stroking myself even though I wasn't hard.

 

[Wonderer67]

We'd been doing butt play (fingers, plugs, etc.) for a couple of years. When shopping on LoveHoney for some new toys for her, I came out and just asked her: would she be willing to fuck me with a strap-on? She said "I don't know.." (which is her response to just about everything where she has to make a decision). So, I suggested we order something. Got one with a 5 3/4 inch cock and one 8 1/2. The 8 1/2" one could be used as a penis extender also but we've never used it for anything but.

First time was heaven! Used a butt plug to loosen up. We have matching metal plugs with heart shaped "jewels" in the ends. Mine's larger .
I bent over the bed and she just slipped in me. Didn't cum from the fucking but sure was hot.

Since then we've done "missionary," cowgirl and one where I have one knee on the end of the bed and the other foot on the floor.

The cowgirl was awesome as I came while stroking myself even though I wasn't hard.

That’s awesome. Pegging can be a great experience. Glad you have been enjoying it!

 

[hisplaceof]

It's an interesting thing

It's quite interesting with my wife. She loves playing anally, both ways, loves toy play, fingers, even mouths, gets off when we use dildos & strap ons attached to most everything, except when she wears like it is designed to be worn. She will do it, but it is not something she is into. She says she doesn't like looking like a guy or doing it like a guy but she will to make others happy when needed. She enjoys it when we do it on her thigh and as I mentioned on all sorts of furniture, mirrors, tables, walls, etc. She loves it when I wear one and dp her. Actually she goes completely ape.

As for me I can take it or leave it, when she has done me with a strap on. To me there is very little difference in it than a machine, a wall or suction toy, or strap on attached somewhere else. We both like to be where we can best see what is happening to one another and feel it as it takes place in them. When all is said and done she swears by the real thing when done with trusted people who can go without a condoms and fill you up. We have had a few times when we were both side by side with strap ons doing us and that was fun. We like doing things together.

 

[Bianca_Bitch69]

She has used a strapon on me and while it may not be as good as a real penis it is still very enjoyable.
She knows what I like and loves to take control and enjoys being the dominate one
She has a massive orgasm every time she does me
Mine doesn't work anymore so I will also wear the strapon and fuck her, of course I am wearing a dress when I do and she loves the idea of a female fucking her

 

[eroticspank]

She has used a strapon on me and while it may not be as good as a real penis it is still very enjoyable.
She knows what I like and loves to take control and enjoys being the dominate one
She has a massive orgasm every time she does me
Mine doesn't work anymore so I will also wear the strapon and fuck her, of course I am wearing a dress when I do and she loves the idea of a female fucking her

I have read about this a few times, a guy wearing a strapon for his lover. I think it is a great idea for her pleasure. I just wonder if some guys feel bad they need to use a dildo to satisfy the wife?
ES

 

[eroticspank]

I wear one for my wife and don’t feel bad at all as we like to switch it up with size and girth. It is also very arousing for me and i can cum inside the holllow strap on just from the experience.

Great! Thanks for sharing and I think it is great for you both. Having a hollow strapon is even better! I tried one on once at an adult store but never used one.
ES

 

[Crios]

This past weekend...
I was bent over the bed slightly. She was behind me, pounding me pretty good. I was shaking like a leaf. She reached around and started playing with my nipples. I screamed. Didn't cum but was shaking so much we eventually had to stop. Glorious!

 

[Crios]

She has used a strapon on me and while it may not be as good as a real penis it is still very enjoyable.
She knows what I like and loves to take control and enjoys being the dominate one
She has a massive orgasm every time she does me
Mine doesn't work anymore so I will also wear the strapon and fuck her, of course I am wearing a dress when I do and she loves the idea of a female fucking her

I'd love to find out what a real cock feels like but that's not likely to happen.
My biggest regret about getting pegged is that she can't really feel anything. Unlike the rest of our lovemaking where we get enjoyment out of each other, I'm the only one who gets actual feeling out of being pegged. . Maybe we'll have to get a strap on that vibrates against her pussy.
And you are soooo lucky that she lets you wear a dress!

 

[eroticspank]

I'd love to find out what a real cock feels like but that's not likely to happen.
My biggest regret about getting pegged is that she can't really feel anything. Unlike the rest of our lovemaking where we get enjoyment out of each other, I'm the only one who gets actual feeling out of being pegged. . Maybe we'll have to get a strap on that vibrates against her pussy.
And you are soooo lucky that she lets you wear a dress!

I think a lot of women get pleasure out of pegging. Like Bianca mentioned his wife has a massive orgasm. Sure you can get a strapon with a vibe attached, that may help. I think it also depends on the strapon she selects--make sure she selects it and feels comfortable with it--and how it sits on her crotch.

I think another part that is very important is attitude. It is not easy to describe but it has to be an event or scene for her pleasure, not yours. If she takes it on and something for her and her fun, she will relax more, concentrate on her pleasure, and find it easier to orgasm. That might include you dressing differently, doing a position she likes vs one you enjoy, etc.
ES

 

[Bianca_Bitch69]

I have read about this a few times, a guy wearing a strapon for his lover. I think it is a great idea for her pleasure. I just wonder if some guys feel bad they need to use a dildo to satisfy the wife?
ES

The other thing she really likes is when I insert a butt plug and then fuck her doggy style pushing against the butt plug gives her the sense of double penetration and that really sends her over the edge.

 

[eroticspank]

The other thing she really likes is when I insert a butt plug and then fuck her doggy style pushing against the butt plug gives her the sense of double penetration and that really sends her over the edge.

Wow, that sounds great!
ES

 

[Subsy]

For myself : A strap on cock worn by anyone represents a loving attitude.

 

[emme8]

I cum so hard from from anal play. I like the occasions I allow Bob to have my ass. I don't do that frequently for many reasons, but when it happens .

I enjoy pegging Bob. It is mostly for him. If he hated it I would rarely do it. I cum by his submission getting off that way.

 

[Goldenfinger]

So a long time ago when my wife was covering vacation time at the hospital she worked in urology. They were talking about men cumming during prostate exams. It wasn’t all the time but it happens. Of course she ask why and they explained it.

she could not wait to share with me and expressed wanting to try this. Well I wasn’t sold on the idea but I looked into it and turns out what she said was true and there was a whole section of porn devoted to it.

so I agreed to let her have her way. The first time was a finger during a bj, the 2 fingers. Then we tried her long slim vibrator which made me nervous cause I didn’t want anything getting lost and having to go to the hospital (We saw that on the internet as well).

There we graduated to a strap on cock. So all this didn’t take years but maybe a couple months. We tried different shapes and sizes and different positions. We both really like it and it is a regular part of our sex life. I wasn’t sold right away it felt good but not amazing it was like infrequent pings of pleasure. After my first anal orgasm, I’m sold.

 

[OlderBtm4U]

So a long time ago when my wife was covering vacation time at the hospital she worked in urology. They were talking about men cumming during prostate exams. It wasn’t all the time but it happens. Of course she ask why and they explained it.

she could not wait to share with me and expressed wanting to try this. Well I wasn’t sold on the idea but I looked into it and turns out what she said was true and there was a whole section of porn devoted to it.

so I agreed to let her have her way. The first time was a finger during a bj, the 2 fingers. Then we tried her long slim vibrator which made me nervous cause I didn’t want anything getting lost and having to go to the hospital (We saw that on the internet as well).

There we graduated to a strap on cock. So all this didn’t take years but maybe a couple months. We tried different shapes and sizes and different positions. We both really like it and it is a regular part of our sex life. I wasn’t sold right away it felt good but not amazing it was like infrequent pings of pleasure. After my first anal orgasm, I’m sold.

What a lucky guy.

 

[eroticspank]

So a long time ago when my wife was covering vacation time at the hospital she worked in urology. They were talking about men cumming during prostate exams. It wasn’t all the time but it happens. Of course she ask why and they explained it.

she could not wait to share with me and expressed wanting to try this. Well I wasn’t sold on the idea but I looked into it and turns out what she said was true and there was a whole section of porn devoted to it.

so I agreed to let her have her way. The first time was a finger during a bj, the 2 fingers. Then we tried her long slim vibrator which made me nervous cause I didn’t want anything getting lost and having to go to the hospital (We saw that on the internet as well).

There we graduated to a strap on cock. So all this didn’t take years but maybe a couple months. We tried different shapes and sizes and different positions. We both really like it and it is a regular part of our sex life. I wasn’t sold right away it felt good but not amazing it was like infrequent pings of pleasure. After my first anal orgasm, I’m sold.

If you don't mind, describe your first anal orgasm. I am sure most people on here would like to know. Was it something that happened by accident? Or maybe you had this feeling and told your wife about it, not sure what was going to happen next but told her not to stop?
ES