Fantasy: What Are Your Crossdressing Fantasies?

(Photo Credits: Sasha Kargaltsev from New York, US [CC BY 2.0])

Hey, guys! Have you ever fantasized about having sex with men while crossdressing? 

We are asking because we read a lot about how some guys get sexually aroused from crossdressing. Some men shared that they love to wear a dress and masturbate while wearing that dress whereas others confessed how they fantasize all the time about having sex with a crossdresser who happens to be either gay, or bisexual, and yes, even with a straight guy. 

Yes, these online confessions included straight men who sleep with crossdressing men, ones who they find are “completely feminine, have little to no body hair, and are ‘passable.'” Passable is, according to this article we are quoting, “a term used when said crossdressing guys look like cisgender females.” 

But that’s not all because we’ve also read confessions of straight men who fantasize often about wearing women’s clothes and having sex with other men but only when they are crossdressing. Or how they love to cross-dress and would fantasize about having sex with another cross-dresser. We say straight because these men have sex with women, have even been in a relationship with them, and only ever fall in love with women so you can imagine their confusion about their sexuality. Often, they would ask themselves why they would fantasize about having sex with other men while crossdressing?

Some gay men on the other hand, feel ashamed about it—perhaps due to fear of judgment—so they try to hide the fact that they cross-dress from their boyfriends or practically from everyone else, really. The same reason holds other gay men back from even trying or acting out on their crossdressing fantasies because they feared that doing so would make them “feel greatly emasculated.” 

Whatever a person’s circumstance or fear is, one thing’s for sure and that’s crossdressing is a common fantasy according to a study conducted by sex researcher Justin Lehmille as cited by Anna Pulley. In fact, it is so common that crossdressing made it to the top seven most common fantasies “specifically homoeroticism and gender-bending.” 

Further, the study revealed that:

  • a fourth of the respondents, men and women alike, had fantasized about cross-dressing
  • almost a third “had fantasized about trading bodies with someone of the other sex”
  • and that “one in four men and one in six women had fantasized about sex with a crossdresser”

Pulley explained that Lehmille surveyed over 4,000 Americans of all genders and sexual orientations and published his findings on a book called “Tell Me What You Want.” Read the entire article here.

That being said, what do you think about having sex while crossdressing, guys? Is it something you’ve already tried? Maybe fantasized about? If so, we’d love to hear your stories and crossdressing fantasies in the comments section below!

There are 40 comments

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  1. Hunter0500

    Having sex while crossdressing or with a guy who does is just not a place I personally can get. I’m attracted to men. Guys who look like, act like, dress like, behave like the usual, standard, traditional, everyday version of men. Same goes for role playing and lingerie. For me, they’re all a distraction as opposed to an addition. For guys into any or all of the many options available, great! Enjoy! There is something for everyone.

    • Dave

      Doesn’t make them less men because they wear stockings or heels. I’m muscular and a man, and it happened few times that I dressed up for bi men who were into dressed up guys, and I had a blast. It’s true that it takes a open mind, which some don’t necessarily have.

      • Hunter0500

        As I said, “For guys into any or all of the many options available, great! Enjoy! There is something for everyone.”

      • Edgar

        I think gay people are crazy. Or at least we play well being crazy. Some times we label us as straight who have sex with man. What’s is that’s supposed to be? what about saying crossdressing straight man who fantasies about gay sex. Never act on it. Hes married with children and 60yo and we have to believe that.? All seems stupid to me. Gay are gay. For experts. Gay is when you fall in love with a same sex person. Means . You dont need to have intimacy with. Just love. Bu sexual is when a one gender identity has sex with another gender people. That’s bi. I dont believe on some of this stuff. I my ex was “TOP”. Until I found out he had a top lover. So was he a TOP? To me es relatively. I tend not to label. But once I see is not for me. I move away from it.

    • Nathan


      A commentary by a ‘real’ man!

      Nathan is proud-of-you!

      You let no fly in the gloss; no run in the stocking; no tear of the dress; no caking of the foundation; no globs of nail-polish or drop of the clutch!

      You stand tall; however,

      a flowered, Tent Dress, replete with hair up swept, held in place by a can of extra hold, lacquer, Aqua-Net hairspray; Putanna earrings… and a nice pair of Marilyn-Monroe, backless heels, might be something we all might try, once, on Halloween?

      Just a passing thought…?

  2. Nathan

    Nathan, Cross Dressing?

    I beg to differ!

    He has a Master Bedroom Suite, replete with a dressing room, dual toilets, dual sinks and a shower with quad shower heads.

    The only time Nathan cross dresses is when he travels from one closet to the other closet.

    The aforementioned is Nathan’s definition of cross dressing.

    He is proud of his ample penis and covers it with a fine example of masculine attire…where all-of-humanity-can witness God’s generosity!

    Size does matter, and hiding it under a pair of fish-net stockings undue the eye candy; not to mention, a slip; camisole; skirt; blouse and a matching clutch-bag.

    Nathan, hangs freely and clearly!

  3. Kirt28202

    Seems this is the new “cool/craze”, but count me out. I like a man that looks, dresses and smells like a Real Man.

    That was easy……….

  4. Evan Eudy

    Just my personal “always wanted to”..Like the pic of the guy a guy, actually the same stockings..or “thigh highs” with nothing else, or maybe a black jockstrap…possibly even lipstick (red) of course…stockings maybe torn…

  5. Alan

    I always dress up when I take cock and I LOVE IT !! It really helps become submissive and enjoy the encounters that much more.

    My fantasy has always been to have 5 men gang bang while I wear my sexiest panties, stockings, garter and nightie

    • Lee

      Alan, i too have the same fantasy, I love wearing a garter belt, stockings, skirt, heels, etc. I feel so hot & horny and submissive, and the men usually are extra horny seeing me dressed like a slut. So far I’ve only had two guys at once, but would love a few more.

  6. Matt

    Not even remotely interested in cross dressing or being with a cross dresser. I like my men butch and not a chick with a dick.

  7. REP

    Nope, nope and nope. Dressing in womens clothes, reminds me of women. I dont want to be with women. Its imagery. How you present yourself to the world is important. I would also not cross dress simply to hook up with a guy cause thats the only way he would be with me. Little more self respect than that here. Fantasies are a waste of mental energy anyway. Fantasy rarely lives up to reality.
    To say wearing womens clothes doesnt make you less masculine is very contradictory considering lingerie and dresses, etc, are the very representation of femininity. Stop rationalizing cause its not working. Do what you want but be honest about it.

  8. Bill

    It’s just not my thing. sorry, I have had several guys ask me to dress but I always declined…once I had a guy ask me to wear a jock strap… even that was a turn off… but I thought what the hell.. I put on a jock strap.. thought I looked kind of stupid.. but it did turn on the guy I was with…he pulled off his pants and his cock was hanging half way to his knees…that’s when I got turned on…

  9. Anewcd

    I’m naturally effeminate [personality & looks] and was very hesitant about cross dressing in the beginning. But after a couple times I began to enjoy the excitement on the [straight, bi, gay, doesn’t matter they all like it] man’s face as he seen me in all dolled up or in some panties and stockings and heels. They make me feel sexy and desired as they lick their lips, look me up and down and grab my ass in whatever I have on.

    For those who want to try it, I say do it. They say don’t knock it till you try it. I did and turned out to be a lot of fun and add something extra to the bedroom.

  10. Blk4white23

    To each it’s own but send the femboys, passable and cisgender females my way. I’ve had fun in bed with these types then a reg masc guy I’m just saying lol

  11. Peter D

    I am married to a woman and consider myself bisexual. My physical attraction and feelings of love are, and always have been, overwhelmingly towards women. I’m not attracted to men in that way, and my sexual encounters with men are for my love of cock….I love having sex with hung men, being submissive for “domish” guys and servicing/worshipping their cocks and making them feel good, but I’m not into kissing or cuddling with them. I’m otherwise outwardly masculine, but as part of servicing mens’ sexual needs I get off on crossdressing. I haven’t worn women’s street clothes as yet, but I’m very into panties, stockings, lingerie, and heels. It makes me feel slutty when I’m sucking a hard cock while wearing those things. I know many guys like other guys who CD. For me, it’s all about what makes me and my partners feel hot, then ultimately satisfied sexually.

    • Rooster

      Peter, couldn’t have said it better myself. Although I’m single but consider myself bisexual as well. Enjoy wearing stockings and heels occasionally and fantasize about doing it for a guy who gets off on it. Even shaved my legs for the first time this winter. I especially enjoy wearing chastity as it brings out my submissive and slutty side.

  12. Hardvict15

    I find myself to be more attracted to transgender folks.. the femine aspect with a little extra. I have had a few guy guy encounters, and watch gay porn. …but find myself returning to trans individuals. I am still open to continue exploring my bi side with feminine men or masculine men. I just like having fun with versatile folks.

  13. john patrick

    Don’t have any fantasies about cross dressers, in fact, something about that entire genre of human behavior and relationships repels me in such a visceral way. The crossdressers that are considered passable (by whose standards?), especially the few that go that extra mile with glamor makeup and sexy dresses or lingerie are actually creepy to me. And I apologize for my honesty. And I just don’t get how some straight guys could be openly attracted to that, knowing the full truth. It’s like they’re trying to fool themselves about being (at least) bisexual.

  14. BiGuy

    I’m physically and emotionally attracted to women, but with men I’m just into their cocks. I can’t envision myself developing a crush on a man, falling in love, or kissing/cuddling one. I love women, every inch of their bodies turns me on. I just have a thing for sucking cock and getting fucked by one. And I love to cross dress while doing it.

  15. Okzebra

    I’ve never seen a cross dresser look as fine in stockings as that man poised if front of the water tower in your pic. Most are OAFs (obese and fem) that I’m not that into. I’d tear that bottom up!!

  16. Wibilover

    I love dressing in bra and panties along with stockings. I love the feel of them. I have served several guys while dressed…it was great. I have also been fucked while dressed…….having my panties puled off and then being bent over and fucked was awesome…i tend to be more of the submissive type and being dressed adds to the submissive feeling

  17. Lamar

    I’m definitely kinky, but not this, nothing to do with looking/dressing in any way, shape or form like a female, too much like drag. However, to each, his own, I’m pretty broad-minded.

  18. Louie the 314th

    Your attitude repels me, sorry. I love how gay men march every year to protest being told their actions were disgusting yet have trouble extending the notion of tolerance and acceptance onto others even more marginalized. The brain is complex and sexuality is thankfully opening to allow people to express themselves safely… well, almost, seems we still have a long way to go.

    To be clear, women’s clothes and makeup are contrived ….they do not magically appear on the female body, people have to chose to accept pink is girly and blue is manly… HA, pink used to be the color of boys 100 yrs ago. Men invented the high heel to ride horses (and Louie the 14th thought they looked cool, added red to his soles and created the fashionable high heel we know today). British aristocratic men wore wigs, not women. Cross dressing has been around for thousands of years and even appears in some religious texts including Hinduism – almost all examples are men… oh wait, there’s Catherine of Medici who, after seeing men in heels, wore them to make herself appear taller for her wedding – this “gender-bending” act started a trend that lives today…

    Your narrow view and understanding of history and life is simply being used to reinforce your gayness…. and why are gay guys so obsessed with labels?? Bi, gay, straight…you’re always trying to call people out that don’t just fuck other men as being confused or fooling themselves… we are simply different but we all know what being different means ….someone will be challenged to think outside of their little box and when they can’t get out, they smash away.

  19. Walter

    Sorry but I like men not men who want to pretend to be women. If god wanted me to like women he would had made me str8 & I would had been born str8. Men can be sexy without all this crossdressing and pretending to a woman. Each their own, but for me it is a turn off.

  20. Hunter4B

    I dated women the majority of my life, have never had the desire to wear women’s clothes or act as a woman. Most of women’s fashion seem torturous to me, and not in the least appealing. It is funny that as a little boy, I recall a story of my putting on my sister’s dance tutu – I was probably two years old, and it did not go over well, (and was told by siblings, that it was considered to be a sign of gay tendencies by our mom), so while I remember the laughs and my mothers anger in that moment, I absolutely recall that I liked the stretchy quality of the material and was in no way trying to illicit a sexual response (nor would I have had one at age two). I like that men’s clothing tend to be rugged, and women’s tend to be silky, and see little of the dichotomous issues others have stated in the blog. From my understanding in college, it is usually men identifying as “straight” who derive sexual pleasure from transvestism and now, even that term makes me laugh, as only men can be accused of transvestism, because when a woman wears a man’s suit or clothing, it is then referred to as the “unisex look!” (I looked up the term, and TODAY it reads a person dressing as the opposite sex, but I wrote a paper in the metrosexual 90s and it’s denotation THEN was specifically male – how far we’ve come?) I must say, I appreciate how many readers shared an academic knowledge of color, fashion, etc., and realize most of this discussion as the social construct that it is.

  21. Jaypretzel

    My boyfriend who is100% gay asked me to put a skirt, panties and thigh highs on and then fucked me in an adult book store while a crowd of guys watched and pleasured themselves. It was his fantasy and it turned him on and that turned me on. It was naughty, submissive and some of the hottest sex we have ever had. Was I passable? Hell no . When I put the g string on it felt good:the thigh highs gave me a rock hard boner and when I bent over in my skimpy skirt, he had full access to my ass. It had nothing to do with being a woman. We dont do it all the time.It is just a different thing we added to our sex life to keep it interesting. To each is own. Some gay men get really offended by cross dressingh and I thinks it’s because of outdated homosexual stereotypes.

  22. Greg

    A married fuck buddy I have likes me to wear a thong. It exposes my ass, which he is interested in, while covering my cock, which he is not interested in. I don’t like thongs, because they seem too feminine, whereas I do like jock straps, which have a masculine association from sports, the gym, etc. In general, I am not interested in looking or acting effeminate, so women’s clothing, accessories, or behavior are not my style. Men’s underwear, however, is a big turn-on, for me and the fuck buddy, as is men’s athletic clothing, so there is plenty of stuff to wear for sex.

  23. Kirk Jackson

    I wear bras, panties, stockings and camisoles and my husband is neutral but wants me to be pleased. I have no desire to be trans and that is his main concern. I wear mostly undercover and uncovered at night when sleeping.

  24. Bert3512

    I like a few above have no desire to fall in love with a man, I am not into kissing him either, what I crave is his cock and cum, I learned at a young age that I love the texture of and taste of cum. I consider my self as bisexual, and answer the gender question as female, if they ask for sex it is male. I love the feminine body and love to give oral pleasure in fact I would rather do that then fuck. When I see a pretty girl my thoughts are always I wonder how she tastes. When I see a man and his member is showing I look and wish I could suck it. Oh I have cross dressed several times in the 90’s at “The Be All” convention, the thrill I had the first time leaving the hotel room was epic in that I had to try several times before I actually made it out to the elevator. The other people in the hotel were very nice and commented to me that my out fit was very pretty, so the hard worked paid off. Wish I had the money to attend again if they are still having the conventions!

  25. Mike

    Some of the most intense sex I have ever had is with a guy who is smooth and dresses up. He’s a total sub and I love it. After it’s over he’s a cute regular type of guy who loves baseball, fishing and the outdoors.

  26. Geena

    Hi im geena.
    Well thats my gurl name im actually a male. I love to cross dress whenever i can for men. And love to have sex dressed there are men that really love for me to be dressed for them. They like to play daddy and daughter while we have sex. Then there are others that only want me in male clothes. But i tell them that i only wear women panties and bras some are ok with it some aren’t. But there is someone for someone out there. We all have the same fantasy’s some just act them out and others don’t.

  27. Lee

    I’m a long time closet crossdresser, and i started out trying on panties, skirts, heels, etc. Eventually i dressed up fully, garter belts, stockings, skirt, heels, wig, makeup, etc. I’ve never gone out fully dressed, but now & then i get a motel next to this truck stop and adult book store. The book store has private viewing booths too. I will go in the book store as myself (not dressed up yet) and try and find a straight or bi guy that would like to see me totally dressed up and come to my room for some fun. If i would find someone, i would give them my room # and tell them to give me a little time to get dressed. Typically i would wear a skirt, heels, garter belt, black stockings, etc. and i would look hot. I would do what turned them on. I never showed my cock, that way i would be totally feminine. I had several encounters over the last few years. Usually i would give a blowjob to completion and sometimes get fucked. This one guy was about 65 or so, and had a nice big cock, 9″ and huge balls too. He loved my lingerie and said he was real horny. I went down on him and teased him with my tongue for a few minutes then finally i took his big cock into my mouth, then sucked on his huge balls as he moaned and moaned. Then i took his entire cock all the way in my warm mouth, deep throating his thick cock. After a while he said he wanted to fuck me, and i said please fuck me. I was clean as i gave myself an enema earlier. I straddled his cock and lowered my wet pussy down onto his rock hard dick and slowly to it in all the way, he was moaning as i rode up & down on his cock. About 5 minutes later he said he was getting close and asked me where i wanted him shoot his load, i said cum in my mouth!! I begged him over & over to shoot his load in my mouth, then he said ok baby, I’m gonna cum, and i got off his and turned around and took his tool into my mouth, a few seconds later he moaned loud and squirted about 7 or 8 thick jets of cum filling my mouth up to the point it overflowed out of my mouth, it must have been a cup full. He asked me if he could come back later that night for another round, and i said sure. I said if he wanted he could bring another guy with him, and he said ok. He showed up with one of his trucker buddies, and they gave it to me good, mmmm!!

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