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guys...has a girl ever dressed you in lingerie and fucked you with a strapon?

My ex-wife put me in a snug fitting sweater dress and stockings, made me get on my knees and lick her 10" cock before she fucked me in every position and made me cum several times. The most intense orgasms I've ever had still to this day. I do miss some things about her. I wish we could do it again..
 
Always dressed in garterbelt, nylons make-up and wig when pegged. SO has also had some of her gf's over and take part. Birthday coming up, she is planning weekend party for me and me being dreeses
 
islandguy2011 said:
Always dressed in garterbelt, nylons make-up and wig when pegged. SO has also had some of her gf's over and take part. Birthday coming up, she is planning weekend party for me and me being dreeses
Click to expand...

So VERY VERY hot. I'd love to be the center of that party!
 
Need this soon

Need to find a woman to do this with me soon. Love being pegged and love dressing.
 
Here's My Story

Here's how it happened for me:

I never had the nerve [I won't say balls] to tell my girl I crossdress on occasion. In bed one night she used a finger on me and I moaned, so she went further. After sex I told her I enjoyed that.

Next time, she used her finger and then pressed her dildo against my ass. When I got into it she used the dildo to probe and eventually when she met no resistance the dildo went all the way in and when she saw how much I loved it we talked about buying a strap on.

The strap on discussion led to jokes "Wait till you find out what it's like to get fucked" she said. "Oh, don't worry I'll be your girl honey" I said. We joked about role reversal and having a "date" at home one night, one thing led to another and we agreed to buy a strap on, The plan was for her to dress as a guy, me as a girl and for her to wear the strap on under her male clothes.

I got dressed, so convincingly it was obvious I had done so before, that led to a chat about my crossdressing. A wild night of sex ensued.

After that, we took a few drives with me dressed as a gal. We went to a costume party dressed in the opposite roles. We went to bed as a guy and gal maybe 20 times and we talked about a threesome with a man while I was dressed but it didn't happen-- we eventually broke up but God those were good times!
 
Thigh highs thong

And yes. Pegged. Lovely on my back with knees pulled back begging for it! Best of times
 
my two cents

I guess because I'm more attracted to "different" men (and women), I've run into many men who enjoy this kind of play. Besides it really being fun, there's something gratifying about connecting with someone who can't generally share their desires.There has to be that trust to discuss and try stuff which is out of the ordinary or accepted. I guess I've always been drawn to naughty and dirty.
 
BettyPoop said:
I guess because I'm more attracted to "different" men (and women), I've run into many men who enjoy this kind of play. Besides it really being fun, there's something gratifying about connecting with someone who can't generally share their desires.There has to be that trust to discuss and try stuff which is out of the ordinary or accepted. I guess I've always been drawn to naughty and dirty.
Click to expand...

Thanks for expressing that. I lived that way for a long time. My partner didn't know my proclivities and i had to find other outlets, to explore my kinks, this thread being one of many fantasies. I now have a friend that knows me better than anyone ever has. A friend that i can explore with not having to fear being rejected. I can even ask for this if i want it. Mmmm
 
BiTodd said:
Thanks for expressing that. I lived that way for a long time. My partner didn't know my proclivities and i had to find other outlets, to explore my kinks, this thread being one of many fantasies. I now have a friend that knows me better than anyone ever has. A friend that i can explore with not having to fear being rejected. I can even ask for this if i want it. Mmmm
Click to expand...

I think a lot partners just don't have much imagination when it comes to sex. It's definitely rough being different. I'm not married, and for a lot of reasons I don't want to be and I don't have to be, but to find a life partner who can be everything one needs or expects has to be very, very difficult.
 
I don't dress but I've been pegged several times. I have my own strap on. I'd like to find a Domme to have an exclusively pegging relationship as part of training me to be a gay bottom.
 
Been close: One of my ex-GF's found my meninpanties link on my favorites. She started following it and I found notes she had taken about guys that I had commented on. Then one night, she asked me if I would wear her silky panties almost half joking. I agreed and this turned her on like crazy. She was never so wet...I have a glass dildo with a smaller head on one side and a bigger head on the other. I was fucking her with the bigger side and she had me lay down with my ass facing her pussy and she slipped the lubed smaller end into my ass. She pumped it back and forth and came like crazy. Fun night!
 
rbtwill said:
Here's how it happened for me:

I never had the nerve [I won't say balls] to tell my girl I crossdress on occasion. In bed one night she used a finger on me and I moaned, so she went further. After sex I told her I enjoyed that.

Next time, she used her finger and then pressed her dildo against my ass. When I got into it she used the dildo to probe and eventually when she met no resistance the dildo went all the way in and when she saw how much I loved it we talked about buying a strap on.

The strap on discussion led to jokes "Wait till you find out what it's like to get fucked" she said. "Oh, don't worry I'll be your girl honey" I said. We joked about role reversal and having a "date" at home one night, one thing led to another and we agreed to buy a strap on, The plan was for her to dress as a guy, me as a girl and for her to wear the strap on under her male clothes.

I got dressed, so convincingly it was obvious I had done so before, that led to a chat about my crossdressing. A wild night of sex ensued.

After that, we took a few drives with me dressed as a gal. We went to a costume party dressed in the opposite roles. We went to bed as a guy and gal maybe 20 times and we talked about a threesome with a man while I was dressed but it didn't happen-- we eventually broke up but God those were good times!
Click to expand...

wow sounds great. bet you are glad you enjoyed that while you had the chance
 
My wife and I were drinking one night....we joked about it. When we got up to the room she undressed me then dressed me in her stockings. There were no words, she just did it. It was uncomfortable, emasculating, and amazing.
 
GF dressed me in a baby doll nighty, thigh highs, wig and full makeup. I looked so much better than I thought I would. We made love and she filled my boi pussy with a dildo and made me feel so slutty. I loved every minute of it.
 
I had few girls dress me up as slutty as they could and fuck my brains out. It was very hot
 
hfernandez1983 said:
Hi,

This question is for the men. Has a woman ever dressed you in lingerie and fucked your ass with a strapon? If yes tell us about it :)
Click to expand...

My wife will be soon. Going to order some panties for me. The thought gets us both really horny, can't wait for the real thing.
 
Unfortunately I have not my wife keeps threatening me that she will get one and use it on me one day :(
 
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