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

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!!


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

So ima ask, I assume you're... Bi?

My assumption has changed a few times as my puny hetero normative brain has searched for an overly simplistic label. :D
 
First I would ask myself what am I doing with a boyfriend, as far as I know I’m straight. But fuck it, I’ve come this far, I’m in a committed relationship with another man I might as well roll with it.
I would ask to him to hurry up and put on a dress and wig because it’s the only way I’ll be able to get hard. And we’re only doing it doggy style.
 
So ima ask, I assume you're... Bi?

My assumption has changed a few times as my puny hetero normative brain has searched for an overly simplistic label. :D
Hehehe yes my love, I have identified as bisexual since I was a young teenager. That was of course a long time ago, wayyy before all these other labels existed. In modern terms I would probably be more pansexual? I just love who I love and I'm attracted to the person, not the downstairs bits. HOWEVER I tend to be MUCH much more sexually attracted to vaginas, exclusively watch lesbian porn (on the rare occasions that I do actually watch porn), and fuck I love eating pussy. I just so happen to be marrying a man :)
 
Brand new been poking around about a month.
When I was about 11-12 my hormones started kicking in. A neighbor boy about the same age used to spend the night. Things started off a just curious experimentation watching each other masturbate. That later gave way to us playing with each other until we came.
I've never had any other experiences until I went through a divorce, spent a couple of years alone, and then got involved with a game playing woman who used me pretty badly.

I ended up moving in with my sister, and BIL, and the next thing you know on heavy into MA for about a year.
There was lots of experimentation during that time. From taking my sometimes fuck buddy girlfriend to strip clubs in Atlanta, and turning her loose, to a guy who came over, and I got high with regularly. That started innocently with us just watching porn, and watching each other jack off. That then led to mutual masturbation, and finally one day while laying there with a raging hard on after doing a big dose he put panties, and stockings on me.
I didn't resist, and we had some very kinky moments over the next 8 months, or so. We did a MMF, with his wife, and my sometimes girlfriend.
I still consider myself very masculine. The feeling of silky panties, stockings, and an ultra increased libido gets me hard just thinking about it.

I never get into that mindset unless I'm doing dope, or talking about the experience.
Been married 18 years, and still am today. I LOVE women, but I miss my kinky fun times sometimes also.

Just because you like the feeling of silky panties rubbing on your crotch doesn't mean that you want to be a woman.
 
On that note, If ever I come across people who are openly and vehemently being homophobic or even boasting that they have "gay-dar", I carry around cards with the crisis hotline, hand them out and suggest they refer themselves to a psychiatrist immediately.
 
On that note, If ever I come across people who are openly and vehemently being homophobic or even boasting that they have "gay-dar", I carry around cards with the crisis hotline, hand them out and suggest they refer themselves to a psychiatrist immediately.
Beautiful!
 
Love this. Thank you.
Yeah, well the other day you were wearing the very male attire that I completely melt for. Army clothes, i.e., camo, army green clothing, etc.
I told you that you looked cute and you smiled and got embarrassed. That fact was even funnier!
I seriously would likely date any guy that walked up and asked me out dressed in that army wear. I’m not really into Army Officer’s clothing. But the camo and green wear just oozes yummy manhood.
 
I'm by all means cisgendered. This is nothing more than a fetish.
Now, this is my creepiest fetish probably... you know besides the whole lolicon thing. I sometimes have sexual fantasies about being female.

I want to wear a dress and bang a girl. I dont' know why. I might have to do with my fetish for lesbians, but I've always... well not always, this is a relatively new fetish for me. 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.
I dont know... for some reason the idea of having sex with a girl while looking like one turns me on. Especailly if it's taped... I would totally sell a sex tape of that, as long as the outfit is good enough to where you can't tell my identity. I wouldn't want anyone I know seeing that.
Another thing is that if there's any BDSM, I'd have to be the dominant. I wouldn't mind being a submissive, but not while crossdressing. If I'm gonna do BDSM and wear a dress, I'm gonna be dominating her. I also would stay silent. Because if I'm fantasizing about being female, I wouldn't wanna talk. My voice is low and it would shatter the illusion.
I'd buy my own dress, if I used a girls dress I think she'd be mad about the "stains" I'd put on.. Cause I'd beat off right into the dress. I've always fantasized about masturbating while wearing a dress and wrapping the silk fabric across my dick and well... probably ruining the dress.

Out of curiousity, are there any girls who would be okay with doing that with a guy? And if so, does that make you bisexual? Could a straight girl be turned on by a male
I think it’s a very hot thing to do. I’m bi but that’s one of my first “bi fantasy”. People are more woke every day. This is a tame fantasy compared to most!
 
I'm old fashioned and if my guy wanted to wear a dress that would be the end of it. Some women may not care but it's personal taste, i like manly men not effeminate ones
 
I'm old fashioned and if my guy wanted to wear a dress that would be the end of it. Some women may not care but it's personal taste, i like manly men not effeminate ones
Fair enough. I don't really care if I'm just hooking up and thats the cat that comes out of the bag. Thats minor compared to some shit I've found out. I don't mind at all socially.

But honestly in a partnership I do prefer someone more masculine myself. I also dress and act pretty "normally" in person. Sometimes people do not guess that I'm gay at all. Depends.
 
I'm old fashioned and if my guy wanted to wear a dress that would be the end of it. Some women may not care but it's personal taste, i like manly men not effeminate ones

In that case, I expect you wouldn't object to tottering around in 6 inch heels, black fishnets and far too tight skirts and blouses. I'm old fashioned too... 😜
 
I'm a guy and i find this shit hot af. iv'e been on a Femboy binge lately and i just cant get enough of them. and most of the time i like it in a wholesome way, most of the time i'm fantasizing about doing cute shit with a Femboy or twink bf, shit like going to the movies or hand holding (most of the time).

if i had to explain it i would say that the dick just makes toping them better. idk i got a craving for bussy atm.
 
Wow, ooookay. Don’t listen to the people replying with the prostitute as any type of option.

You just have to be with the right person who is super open minded and isn't judgemental etc etc.

I was with somebody for a year and he’s a crossdresser. It didn’t bother me at all (I’m all about embracing yourself and self expressions etc etc)
Never went out in public dressed, only in private and during sex sometimes. Which I thought was pretty hott.
I felt like I was hooking up with a girl, which I’m always down for lol.
He was super nervous when he shared with me what his interests are and was super shocked with how supporting and accepting I was. Apparently, in his history of dating, it was super rare to find someone (me) who doesn’t judge crossdressing and how so many girlfriends “disapprove” or is a deal breaker for them… since every single one who he had opened up to it about, took off and said peace. (Their loss!)

And yes, he is a 100% straight man and is only attracted to women. So yes, straight men who crossdress do exists:]
BTW side note: I am a straight female. Girls are hott, but I could never date one. Lol if that makes sense. I have definitely hooked up with some though lol

Anyways, I did try to motivate him for us to go out with him dressed and us looking hot and be able to have a girls night… but never happened.
People are so judge judge judge and so closed minded. It makes me sad. You can’t control what you are into or what turns you on.
Do what makes you happy, and whoever can’t accept your interests; that’s on them!
 
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I'm a guy and i find this shit hot af. iv'e been on a Femboy binge lately and i just cant get enough of them. and most of the time i like it in a wholesome way, most of the time i'm fantasizing about doing cute shit with a Femboy or twink bf, shit like going to the movies or hand holding (most of the time).

if i had to explain it i would say that the dick just makes toping them better. idk i got a craving for bussy atm.
fuck man i was thursty af in august.
 
I'm a guy and i find this shit hot af. iv'e been on a Femboy binge lately and i just cant get enough of them. and most of the time i like it in a wholesome way, most of the time i'm fantasizing about doing cute shit with a Femboy or twink bf, shit like going to the movies or hand holding (most of the time).

if i had to explain it i would say that the dick just makes toping them better. idk i got a craving for bussy atm.
Conceptually I’m fairly sure I could date someone with a penis if I was really attracted to them as a person and felt an emotional connection. But I’m 100 % sure they’d also have to have breasts, preferably hormone produced rather than silicon. If so, I would not consider myself gay (which I don’t anyway). Clearly there is a major category diffference in my head between “Femboy” and “Transgirl”.

It’s a taste thing not a judgement thing. Even when I was as high as fuck powering through Pornhub for hours in search of the best trans video ever made I would instantly skip any where the actor turned out to be just a “sissy” or “femboy” or any offer the dozen other names for that kind of thing.
 
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