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How would you react if your boyfriend wanted to cross dress during sex?

Jealous of the intersex thing. Definitely on my bucket list... although, I could do without the needles and the homeless shelter.

As for cross-dressing guys, I don't see what the big deal is. People are so repressed. Clothing doesn't make you gay. It's just clothing. I've worn: panties, bra, garter belt and stockings. My wife seemed to enjoy it, but we both had a chuckle.

It depends on what the guy looks like. I was skinny at the time and am pretty hairless, so I can pull it off. Big hairy guys look silly, but the whole thing is silly.

Experimenting is healthy and (however cliched) can keep the spark alive. If you've been with someone for 20 years and they say they want to do something different... just go with it. You never know.

I'm tempted to post a NSFW pic of myself in some lingerie, but I won't. @dalpat077 might have a heart attack if he stumbles upon this thread and sees how sexy I am.
Dude. My questions alone would result in a public outcry! :ROFLMAO:

Whatever. Hope all that stuff you're putting on, at least, doesn't have holes in it! 👠 Unless fishnet of course (but I think you get my drift)! :ROFLMAO:

Nope. Not looking for answers either (as he frantically fumbles about for an Alprazolam and the "Unwatch" button)! 🤪
 
Me — I’m non-binary and dress in all kinds of clothes. It started as a (once shameful) kink but I realized eventually that it gave me a lot of comfort. My ex-wife, who I still sleep with on occasion, is cool with it. You really should give it a go, in private/solo, just to see how it feels. I once had a prom dress I thrifted, just to see how that felt. It was hot! Open to answering any questions. I realize this thread is old but wanted to chime in.
Marck

How long did it take for you to explore being non-binary? I feel like I am currently moving towards that with how I have been dressing in the past year or so but a little sheepish about applying labels to myself or whatever. What has your experience been?
 
I’ve always wanted to go to bed with a woman and both of us wearing stockings like this. I think I’d be role-playing being an 18th century Parisian lesbian with her. Can’t really see that anything is stopping me doing it. Although I’d have to pay for the willing French speaking partner at this point in my life.

 
I wanna wear a nice, fancy dress. Like a Chinese dress. Or preferably something very soft and silk, and then give it to a girl. This is would be weird, because I'd have to shave my beard. I'd also need a nice wig and makeup.

This was my favorite part 😂 😭
 
How long did it take for you to explore being non-binary? I feel like I am currently moving towards that with how I have been dressing in the past year or so but a little sheepish about applying labels to myself or whatever. What has your experience been?
Send me a message we can talk about it.
 
Anyone ever wanted to try be strap on fucked and humiliated or try the whole sissy thing?

I would like to get those expensive silicone breast things u can strap on like a bra, a decent wig, some nice sexy clothes and get someone to help me with make up after completely shaving legs and all. Then walk around a city I'm not known. And get fucked up ass afterwards obviously!!

Would like to see what it is like to be a woman/tranny for a day

Happy being a man. Would like to try submissive role in bdsm. Not sure if it's for me but ya never know.

One thing I am planning on getting is lip fillers. At least a full ml. More of the female style than the male one. Dont care if I look stupid or people laugh I like girls and transexuals with cocks I'm comfortable with my sexuality.

The idea of big sexy female duck lips really turns me on.
 
Oh wow this thread again. I remember it from 5 years back when it was new.

Eh, this certainly wouldn't be my thing, I kinda like my guys to be, well, guys. :p

But I guess if I loved him he wanted to try it I'd give it a shot.
 
Tryptamite said:
One thing I am planning on getting is lip fillers. At least a full ml. More of the female style than the male one. Dont care if I look stupid or people laugh I like girls and transexuals with cocks I'm comfortable with my sexuality.

The idea of big sexy female duck lips really turns me on.

I was gonna make a thread about this the other day to find out if any guys actually like lip fillers. Whenever I see women with duck lips, I'm just like WTF. It looks crazy to me. I liked the rest of your post though. I've always wanted to go full drag too. I've looked up wigs online but never bought one. I should do it before I get too old.

JessFR said:
I kinda like my guys to be, well, guys.

Doesn't make a man less a man to wear female clothes any more than it makes a woman less a woman to wear a hoody and jeans.
 
Doesn't make a man less a man to wear female clothes any more than it makes a woman less a woman to wear a hoody and jeans.

That's true. But we're talking about something that goes a bit beyond that here.

Now granted, I wouldn't say that having this fantasy in itself means you're less of a man either.

But, the original question of the thread is how I (or anyone else as the partner of the man in this hypothetical) would react, and I'm saying that while I'd be willing to go along with it, it's not really my thing.

And the reason it's not really my thing, well, while having this fantasy doesn't make you not a guy, it does mean you're not really taking on the role of a guy in bed, no?

I mean, if the whole point of the fantasy is for the guy to dress up and fantasize of themselves as a woman or something, well, I'm not really into women, so I don't think it should be surprising that I'm not really into the fantasy either.

That's probably a better way to describe what I'm getting at here.

But eh, provided it's just a fantasy they wanna engage in from time to time, that's not that big a deal.
 
I've worn my wife's lingerie during stim fuelled fuckfests and it was a massive turn on for both of us. She fantasises about sex with another woman and I fantasise about watching - it hasn't happened yet so this is the closest we've got. But that stuff just feels so nice on your skin and automatically makes you feel sexy. Christ, if I was a woman and wore that stuff on a daily basis, I'd be constantly dripping wet ..
 
@JessFR

If it's not your thing, that's cool... but, I don't think dressing up in lace/stockings is inherently female. It's nice to just wear sexy stuff in the same way women like wearing casual "menswear". Women in their natural state have hairy legs and don't wear make up. Long hair (ie. wigs) isn't inherently female either. The only part of female attire that doesn't make sense for men to wear is bras. It is no coincidence that this is my least favourite part of the outfit. I like men to be men too. Wearing stockings doesn't make you less of a man. I think (a lot of the time) people go on about trans stuff, it's mostly what is socially acceptable in terms of fashion.

I get what you're saying. I haven't read the OP recently, but (if I remember correctly) the thread was more about crossdressing... which isn't necessarily about being a woman. I've never been remotely interested in being a woman, but I do like dressing up sometimes for the same reason women do. See the comment from @F.U.B.A.R. above.
 
@JessFR

If it's not your thing, that's cool... but, I don't think dressing up in lace/stockings is inherently female. It's nice to just wear sexy stuff in the same way women like wearing casual "menswear". Women in their natural state have hairy legs and don't wear make up. Long hair (ie. wigs) isn't inherently female either. The only part of female attire that doesn't make sense for men to wear is bras. It is no coincidence that this is my least favourite part of the outfit. I like men to be men too. Wearing stockings doesn't make you less of a man. I think (a lot of the time) people go on about trans stuff, it's mostly what is socially acceptable in terms of fashion.

I get what you're saying. I haven't read the OP recently, but (if I remember correctly) the thread was more about crossdressing... which isn't necessarily about being a woman. I've never been remotely interested in being a woman, but I do like dressing up sometimes for the same reason women do. See the comment from @F.U.B.A.R. above.

That's so true. Wearing a bra doesn't interest me at all and would just look silly. But silk panties, lacy thongs, stockings and tights just feel lush on your skin. Especially if you've depilated beforehand.
 
Anyone ever wanted to try be strap on fucked and humiliated or try the whole sissy thing?
Sure. Once I had to get one hooker to ream me from behind with a silicone dildo while I ploughed her colleague from above. After 5 meth-fuelled hours it was a last ditch effort to get me over the line. To be honest though, as that line was crossed it felt very manly and not very sissy at all. Even with the hooker yelling “yeah! Bring it home bitch! Bring it home!’ As she slapped me repeatedly on the ass.
 
My fiancé?? Firstly, he is very masculine, there is nothing effeminate about him. So it's difficult to even imagine him in women's underwear, lingerie, clothing, heels, make-up, anything at all, without it being for humorous purposes like for a Rocky Horror or Halloween costume party. So doing it for sexy time?? I don't think I could take him seriously.....If he wanted to do it, I would have absolutely NO problem with it whatsoever!! I will forever support anything he wants to do. But I can't imagine that he would want to. And I have known him for a very, very long time :)

However I DO find it very sexy when effeminate men crossdress, or wear one or just a few items of women's clothing and wear make-up just on casual occasions. I have several male friends who do this, and it's seriously sexy!! If I were to ever have sex with a guy like that, and they wore women's lingerie, HOT DAYUM yes that would turn me on!!

Happy being a man. Would like to try submissive role in bdsm. Not sure if it's for me but ya never know.
You never know until you try it huh!! :)
Are you straight, gay, bi, somewhere in amongst all of that?? Just curious :)
I LOVE LOVE LOVE how open and comfortable you are about the topic of this thread <3
 
The closest I got with my ex-boyfriend is black eyeliner + black nails. And it was great effort to make the nail polish perfect (getting him not to use his hands for awhile).
 
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