Why do men cross dress?

Why do men crossdress?

Girl friends and wives want to know.

Why do men cross dress?

Why does my husband cross dress?

How can I make him stop cross dressing?

The unfortunate truth, is that there is no simple, one line answer to these questions. If there were, you probably wouldn’t be reading this article, and the debates on this topic would be silent.

In my personal experience, the fascination with woman’s clothes started when I was very young. I must have been about four years old, and I remember going to great lengths to procure and then wear my mom’s nightie. My most vivid memory is as a teenager, nervously buying a pair of pantyhose from a local supermarket and then wearing them home under my pants.

I felt (and still feel) a need to wear woman’s clothes, and I can’t quite explain where it comes from. The media like to think of cross dressing as a sexual perversion, and so naturally they see the desire to cross dress and purely for sexual gratification. The problem with this theory is that when I (and many others) first felt the desire to cross dress I didn’t know what sex was.

Many cross dressers I’ve asked describe the need as ‘feeling more comfortable wearing woman’s clothes’. This is sometimes (but not always) coupled with the desire to be seen as a woman. To not just dress like a woman, but behave like one as well, to wear make-up and otherwise pass as a woman. There are others who cross dress for sexual excitement. The need to cross dress is indeed a spectrum.

That still doesn’t answer the question why do men cross dress?

Marcy proposes a few interesting answers to this questions.

One argument is that transvestism of cross-dressing is a way of offering a challenge to society’s preconceptions about gender. Some men cross-dress because they are unhappy at being men. Others didn’t mind the male state, but also like to put on women’s clothes occasionally. Some men cross-dress simply to make a passing social or fashion statement, and some because they have emotional needs that can only be met by the comfort that wearing women’s clothes gives them.

Yet the true reason why men cross dress remains somewhat of a mystery. It is intensely personal, often confusing and sometimes guilt ridden. I’m hopeful that as society grows more tolerant of diverse gender expression we will see more cross dressers and transgendered stepping forward to share their stories. Without the need to justify their behavior, and no longer shamed by society perhaps we will be better able to answer this baffling question.

Comment and let me know, I would love to hear- why do you cross dress?

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1,011 Comments
  1. Profile photo of Tammy
    Tammy 1 min ago

    In my opinion, there’s a larger issue that needs to be raised to the world. Why shouldn’t people experiment with gender? In modern society, are there any “good” reasons for traditional gender roles? The arguments would fill a book, but that’s no reason to avoid the discussion. In the meantime, the easiest answer to the title question is because we like to. That might not be much of an answer, but it’s no different than asking someone why they eat chocolate.

  2. Profile photo of Monika Sweet
    Monika Sweet 1 month ago

    why Men Cross dress… my pick, we are hard wired like that. We are born with the traits of both sexes to different degrees. Some has this balance, others are skewed to extreme ends… who are bent more towards being male stay males and never feel that urge to Crossdress while the ones who are on the other extreme go for extreme measures to transform themselves to be the woman they believe they are. The others who are in between these two extremes become Crossdressers with some or little inclination to transition.

    Why are we hardwired like that… that’s a question yet to be answered like numerous other mysteries about the human mind and how it works.

  3. Profile photo of Dianne Baldwin
    Dianne Baldwin 1 month ago

    I love the feel of silky panties , bra and forms and I’m a lot more confident as a female.

  4. Profile photo of Alyce Victoria
    Alyce Victoria 2 months ago

    I cross dress because I never felt comfortable being a man and at points I flat out don’t like being a man

  5. Kitty Cox 3 months ago

    My desire to start crossdressing began when I was still wearing diapers. I feel lucky because I have very clear memories of key events that led me to believe that (for me) it started as a fetish as all other fetishes do. They begin with a focal point (an object, an experience, situation, or emotion and a variety of other things defined only by the person that has the fetish) coupled with sexual stimulation. occurring normally at a very early age sets and defines the fetish.
    Anyone that tries to tell you that you do not experience sexual things from infancy to death is flat out in denial. If you do not at least remember receiving good feelings from your sexual organ by the age of five then you have just repressed these memories for reasons that only you can explain.
    Although many people think of sexual development as a process that begins in adolescence, it actually starts at birth and continues through the life span. Baby boys may have erections immediately after birth while girls can experience vaginal lubrication and clitoral erections as early as the first 24 hours of life. Both infant boys and girls may discover unintended genital stimulation during diaper changes or bath time. Any observant caretaker may observe that babies and very young children have learned to stimulate their own genitals, this usually occurs earliest in boys around 6-7 months of age while girls follow at around 10-11 months of age. It is important to realize that infant and childhood self-stimulation of the genitals is not goal-directed toward orgasm. Rather, it is more of a self-comforting, “feel good” activity (all age ranges are averages and some fall outside of range like all sexual development studies will) Ref. Miracle, Miracle, & Baumeister
    A hypothetical
    Early morning, a young male child still in diapers, is enjoying a pleasurable feeling from the area of his genitals and the child’s parent is wearing, (let us say a leather coat). The parent scoops-up the child close and snuggles with the little one, telling the child that they love them and kisses the child before returning the child to the comfort of their crib. The child associates the warmth, love, safety, and comfort of their parent along with the smell, sounds, and feel of the leather, along with the stimuli of the “feel good” from the erection and you have the beginnings of a leather fetish; if the parent repeats this day after day, well it is just that simple. It is important to understand that it is all dependent on how the child formulates this experience as to rather they develop a fetish or not but this is a very plausible consensus. This is not to say to parents that they better not wear leather jackets around there sexually stimulated children but please do not make the mistake of believing that your very young children are not sexual beings and will not be effected by things that you do around them. This is also not for the blaming of anyone, (from those loving and forgiving words) for we know not what it is that we do.
    Here are some memories that I know lit the fire for my eventual love affair with female clothing and contributed to my initial crossdressing fetish with (Panties) just the word makes me feel feminine and sets off my desire to crossdress.
    My mother always wanted me within eyesight of her at all times and because of this, she would have me play on the floor while she dressed. My mother had me when she was 39 so she was still in the habit of dressing in the full fashion under garments and frilly feminine foundation wear. The ritual was quit time consuming and I watched the ritual day in and day out. There were the bras, full fashion nylons with the seam up the back, fashion frilly garter-belts, nylon-camisoles, nylon lace embellished half-slip, petticoats at times, and both plain and lace embellished nylon panties, all as she sat in front of a makeup vanity doing her hair and makeup I could see in the mirror every angle. Knowing what I know now, I realize that I fully deployed my favorite pastime and that was self-stimulation for that “feel good” self-comfort. I know that this bonded me to this as a very pleasurable thing. The fixation was not on my mother but on the lingerie and all of its lace and frills, and the pulling and manipulation of the fabric that had me mesmerized.
    Another vivid memory was of a night when my parents had a friendly gathering; my mother wisped me into the back bedroom to change me. I remember having an erection at the time and she was about to undress me, but she had closed the door and while it was a little embarrassing it was okay because of the privacy; but while laying all splayed out on the bed with my little hard-on, two of my mother’s female friends came bursting in the room. While I laid there naked, the two female friends looked on me as they casually bantered back and forth. The shame and embarrassment started to take its toll. Like many mothers and fathers do, my mother tried to make routine things a kind of entertainment (so as to deter a baby from crying). She had the habit of holding up each item of clothing and showing it to me, acting like it was the most exciting thing in the world, then she would put the garment on me. She also had the habit of calling the plastic-pants by the word panties. This time as she held the plastic-pants/panties up in front of the two on lookers, she told them that soon I would not need my little panties any longer. I remember a disjointed feeling of my mother calling them panties, the female friends looking at my naked body with an erection, along with the arousal. The feeling of being unhappy about mother hinting about taking away my panties. This embarrassing event played into my earliest fantasies about forced crossdressing. Me being forced to wear panties and having to lay across each of my mother’s female friends laps, and have my little panties spanked for desiring to wear girls panties. From time to time one of my babysitters used these very words (do I have to spank your little panties). This further sealed my fate for the desire to crossdress.
    Another well-remembered night happened again when I was still in diapers. In one of the bedroom were two single beds and one crib. I had a brother that was 18 months older than I was and I remember that he was in the crib because I had nightmares when I slept in the crib and he did not. I was in one of the single beds and my mother and father were in the other single bed. My parents were fooling around in the other bed. I had no idea what fooling around entailed at that young age. I was only able to theorize about that when I knew of adult things later in life; all I know is that I thought they were busy and that was my que that I was free to play quietly under the covers and in the dark. I started playing with the only things that I had. let me assure you that the primary driving force was the desire to fully enjoy the feelings that I was experiencing from a growing erection. the other things in the bed with me was my teddy bear, my cloth diaper and the plastic-pants/panties or should I say the only thing that I had that looked something like the lingerie that my mother got to play with in that very room every morning. I got in the zone of arousal and decided to take off my Plastic-pants/Panties and my diaper and get naked then I had the idea to dress my little teddy bear in my plastic-pants/panties. In my mind, I remember like it was yesterday was that I thought it would be exciting to dress my little teddy bear up in my panties. The next thing I knew the lights were on my covers were flung off of me, I was exposed, naked, with a stiff member, and my little teddy bear dressed in my very own panties. My mother gasped! Then said look what he is doing! and told my father to spank me. My father gave me a feeble swat (he was always more excepting about such things) then my mother threw both of us out of the bedroom exiling both me and my dad to the 2nd bedroom. I remember it like it was yesterday I was all excited about putting my little panties on my teddy bear. my little stiff cock was felling really good and I thought I was doing something risky but the desire was in charge and I was loving it. This also played into my fantasies, in a quirky thrill of being exposed with shameful desire for wearing and dressing others in girl’s undergarments. This further sealed my fate for the desire to crossdress.
    Around the age of four or five, I was playing house with two girls down in there parent’s first floor apartment. I was having so much fun; my goal was to see if the dolls had panties and if they had female genitals because I desperately wanted to see what that looked like. I already found that girls were just the most beautiful things in all the world and they rightfully had the privilege of wearing the prettiest clothes, especially the prettiest garment of them all, panties. I theorized that if they wore the prettiest garment over their genitals then it had to be something wonderful to behold, especially sense girls guarded this privileged reveal to nearly no one. Therefore, I thought the dolls could help me with both desires. I wanted to dress the dolls and of course, the panties go on first, I was upset when the little girl told me that the dolls did not have underwear and I could see that the dolls both Ken and Barbie had nothing between their legs. I asked both of the girls to show me theirs and exposed myself first to get things started. I was rock hard when I did the big reveal. Now remember I was 4 or 5 years of age at this point so please do not tell me that children are not sexual beings from birth. I got the little friend that lived below me to show me hers but I did not think she had shown me anything because it was very quick and I did not know that the little hairless skin fold that I did see was really the thing that they had down there. I got the little girlfriend of mine to crawl under the bed with me and asked her to pull down her pants so that I could see her cute little bottom and I asked her to pull down just her pants and let me see her bottom in her underwear first. She said if I would, she would! Therefore, I agreed, and then I got her to pull down her panties to. I loved how smooth and soft her skin was and never had been as aroused as I was at the roundness of her bottom. I told her she had a pretty bottom, she returned the compliment and said I had a pretty one two. We played and played so much that I did not want to stop and pee and eventually I wet myself. Ann Marie ran and got her mother. Needless to say her mother was very mad. Her mother put me up on top of some furniture and striped me naked right there in front of Ann Marie. She then told her daughter to get a pair of her underwear for me to wear as she wiped me down with a washcloth. She took the panties from her daughter, and spread open the elastic waistband of the panties for me to step into the panties. I hesitated for a second and got a stinging swat on my backside for it. She again spread open the elastic waistband and I stepped directly into the first pair of real girls’ panties for the first time in my life. Her mother pulled the panties up my slender legs and I received my first thrill of slipping a pair of panties up my legs and having the elastic waistband and leg bands used to pull the fabric around so that the thin material draped properly on my little thin body. Then she lifted me up, placed me on the floor, and told me to go home. As soon as my feet hit the floor, I ran through the apartment, out the door, up the stairs, through our apartment and into the back bedroom, pulled the panties off, and threw them under the bed. I have this treasured memory that was so defining to draw on and has shaped countless fantasies. Once again this experience further sealed my fate for the desire to crossdress. Each occurrence further entrenched the desire and expanded the variety in witch to express the desire.
    I remember going into my mother’s dresser, looking for a pair of her panties. Picture a small boy trying to wear a drape as a pair of panties. This did not deter me I asked the girl down stairs if I could wear a pair of her panties. Not thinking of the mechanics of it, I discovered that I could not take the chance of being found naked by her mother I still wanted to put them on so bad that I pulled them up on top of my pants before I gave up and chickened out.
    As I grew older, my desire for female attire has only expanded, first to all kinds of lingerie. To sexy proactive, reviling clothing and now I can get a thrill from a pretty floral pattern on a woman’s shirt to the blousing of a pretty feminine top, as it gathers at the waste, when tucked into a skirt, shorts or slacks.
    Why do I crossdress? It is because I am looking to repeat the innocent thrill of that first time experience full of the vitality of youth; the freedom of just experiencing it without all of the baggage that society burdens us all with, and I allow myself that pleasure. It is said that as we indulge in any habit we are just chasing that first time. The first cocaine high, that first love, that first crush that hurt so bad. And so on and so on.

  6. Profile photo of Ashley
    Ashley 3 months ago

    My reason for dressing is because I love to feel, look, and act like a woman. I want to know fully what it is like to be a woman in every respect, to feel sexy and adored by men, to feel the eyes of the room on my delicate body adorned with pretty clothing, and to feel all the sexual energy I do choosing what I want and who I want as a woman. It just feels so powerful and sexy when I dress. I think the best way to sum it up is that I adore women so much that I want to be just like them, and become more and more girly every day.

    • Profile photo of Grace
      Grace 2 months ago

      I’m with you girl, I just love the feeling dress d, the sexery, the better

    • Profile photo of connie
      connie 2 months ago

      exactly how i feel when i’m dressed

  7. Profile photo of Carol Taylor
    Carol Taylor 3 months ago

    I cross dress because I enjoy it. I love wearing women’s clothes – or, my clothes as I prefer to think of them. I love how they make me feel, and for me it’s something really positive. I can understand and believe that for some who cross dress, they are making a statement about fashion or gender norms, but I think that for most of us, it’s who we are, who we want to be, or even who we hope to have the courage to be – one day

  8. Profile photo of Patricia Marie Allen
    Patricia Marie Allen 3 months ago

    Why do I cross-dress… Short answer — it’s who I am.

    Having discovered my feminine side at the tender age of 8 or 9, I’ve gone through several stages. In the beginning it was simply the fascination of looking like a girl. Later, in my early teens, an erotic element developed as I developed an interest in girls.

    As an aside: a dirty little secret. I used to dress up from the skin out, being sure to securely tuck the male equipment, then stand in front of a full length mirror and lift my skirt to see my panties. Part of that was erotic, part of it was seeing illusion of being female in the extreme. But that aspect lasted only a year or so.

    I lived in the mistaken idea that this was just something I did because I was bored. A hobby of sorts. I knew for sure that once I was grown, once I was married, I’d leave it all behind as an adolescent/teen memory. Even after got married and discovered I hadn’t left, or was the couldn’t leave, it behind, I stubbornly kept it as a separate part of my life, driving a wedge between the feminine expression and my male persona. I knew guys who were self-conscious about their hair and use what I termed as “beauty products” like shampoo and conditioner on their hair and I prided myself that I wasn’t wimpy like that. I washed my hair with Ivory soap in a “manly” fashion, not like those wusses who used that girly stuff.

    It wasn’t until my wife caught me dressed that I finally researched and made an attempt to reconcile myself with my feminine expression. It took years before I could unify my feminine expression with my male persona and just be me without any separation.

    I now refer to myself as a feminine male. My male body has served me well and I have no real issues with it. OK, so if my wife wouldn’t freak about it I’d have modest breast implants. But I’m happy with my role as husband, father and grandfather and I wouldn’t give up one aspect of that for a moment.

    Still I don’t own any men’s underwear, wear a bra w/breast forms 24/7 and I only have one pair of men’s pants and two men’s shirts and no men’s shoes, yet my closet is bulging with clothes, a small portion of which allows me to masquerade as a typical male, even though they came off the women’s rack. A sad commentary that women are allowed to be as masculine as they want, but men can’t even take a baby step toward feminine.

    Why all this for a man who can’t even imagine transitioning? As I said, I cross-dress because it’s who I am.

  9. Profile photo of Sheila Tampa
    Sheila Tampa 3 months ago

    Hi Girls,

    Like many of the previous commenters, I really don’t know EXACTLY why I crossdress. Like many others, I started trying on my mother’s clothes sometime between age 7 and 9. I especially loved panties and slips (and still do at age 71). My crossdressing at home was limited to the few occasions when I would be the only one at home and I knew the others would be out for at least a couple of hours or more. I occasionally would try on my mother’s high heel pumps and a dress. I did not try makeup, and I did not have access to a wig.

    When I moved into my own apartment, I started buying women’s clothing from catalogs. I didn’t buy a wig and makeup until I decided to join a Tri-Ess chapter. I felt guilty at times, and like so many others, purged my entire feminine collection completely at least 2 times. But, around age 40, I started a new collection, including quality breast forms for the first time, and just accepted that I loved dressing as a woman and acting as a woman when dressed.

    I never felt like a “woman trapped in a male body”, and was OK being a guy most of the time. Now, at age 71, I am very happy to be a crossdresser. I regularly attend the meetings and dinners of a TG social and support group. I have also attended 6 Southern Comfort Conferences (SCC) and will be attending this September’s SCC. SCC is probably the most well-known TG gathering in the USA (and maybe the world). I attended one Keystone Conference, which is another popular TG conference. I occasionally go out (but not very often) completely dressed as a woman.

    Back to the topic’s question … why do I crossdress? I’m guessing the following points all play a part:
    1) from the very first time I tried it right up to the present, I just found it to be exciting and very pleasurable;
    2) I have always been a bit of a non-conformist, and I think the fact that crossdressing was (and still is to a lesser degree) a “social taboo” makes it even more exciting;
    3) I’m very liberal and open-minded, and with that mindset, I feel there’s nothing wrong with crossdressing and why not do it if I like it;
    4) and, finally, maybe the simplest reason … crossdressing is just flat out FUN!

    I often kid my fellow crossdressers and say … “I know crossdressing is not exactly a hobby (it’s more than that), but if it were counted as a hobby, it sure beats bowling or stamp collecting! (Sorry, bowlers and stamp collectors … no offense intended).

    Love,

    Sheila.

  10. Profile photo of Jennifergordon
    Jennifergordon 3 months ago

    Panties forever!

  11. Profile photo of Jaye Dee Bowman
    Jaye Dee Bowman 3 months ago

    Why do I crossdress???? I do it because it makes me feel more at ease with myself. I also have a “need” to feel the snugness of my bra(w/forms), the silky feeling that my panties give me when I’m wearing them, the joy of stockings or pantyhose on my legs, the sound of my heels on a floor, the rustle of my skirt when I walk, the feel of my blouse or my dress on my skin, the length of my hair tickling my neck, the joy of applying my make-up.
    This is how I become the girl that lives inside of me and this is how I let her out. If I could, I would transition totally and never look back to the male part of me that always felt guilt and ashamed. THAT IS WHY I CROSSDRESS

  12. Profile photo of Jennifergordon
    Jennifergordon 3 months ago

    I love my panties, nylons and dresses. Not giving them up! Jennifer.

  13. Profile photo of jamey Trusty
    jamey Trusty 3 months ago

    I have been crossdressing since I was a child don’t know what really started it. I almost feel like a split personality when I dress male am all male and when I dress woman its the same. I have tried going out in public but like the knowledge and grace to fully pull it off i honestly fell like that man in drag. Recently with you help and a newly purchase you a cheap down under I really feel more like a woman. I am saving my money for a better down under but this is the first time I really feel complete. I have tried all the taping and was miserable and confined. I am trying to learn more and more on how to blend in. I also want to add i have been married for 22 years and she is very supportive. I also have 2 grown daughters who know my female half and also are supportive.i am 59 years old and retired military also totally work in a mans world. My stepson is the only other male who knows i exist. I try to keep my secret from my grandsons and don’t want them to misunderstand. I do most of my dressing after work and behind close doors and if I do go out it is way out of town so there is very little chance of being recognized by one of my coworkers or friends. I tried once in town and a no longer so call friend spilled his guts to my then coworkers. I worked real hard to discredit him saying you know me guys you honestly believe I Crossdresser. I am real country so I was able to convince them. Little do they know so I stay out of town or state if I decide to go out in public but haven’t had the best luck in pulling it off. Looking forward to learning more ways to blend in so I can enjoy my feminine freedom.

  14. Profile photo of LingerieLouise
    LingerieLouise 4 months ago

    When I was going to high school my mates dared me to go to the annual dance dressed as a girl. It was the local boys and girls high school social get together. I knew a girl who went to that school and she lent me a uniform and gave me basic instruction to pull off my stunt. All I purchased was a wig from the local party supply shop. My female impersonation was meant to be a joke and I was to announce myself by taking off my hairpiece while dancing. I was astonished to discover no one at the dance saw through my disguise and I enjoyed what I was doing like I could not believe. There I was performing what I could best describe as a female acting roll. I was fascinated to see how long I could continue with this masquerade until I revealed myself. People were saying things like, ‘now you have to dance with the boys tonight’ and ‘the boys want to meet you’ I was truly being accepted as a girl when all the while that was not really my intention. Of course, I saw my mates that made the dare on the other side of the hall when I spontaneously decided, because of my success as passing as a girl, not to disclose my identity. That night no one knew I was a guy. I decided to leave early when the first girls left, because I felt I had achieved something special and didn’t want to take anymore chances. The ironic thing was that when back in school with my mates they all said that I did not go to the dance, that I chickened out. I could not convince them that the tallish smiling blonde they laid their eyes more than once was actually me. My mates simply did not believe me and I felt it was something special indeed to be a boy who could pass as a girl in the close company of so many people at a dance.

  15. Profile photo of Cecily
    Cecily 4 months ago

    Hi I’m Cecily
    I am new here I am more curious at this point then anything I have had these feelings more then likely for a while but have just started coming out lately I am married so it’s hard to figure things out but I am trying to work on it not quite sure of what my style is but hopefully I can work through this and figure out how I want to do this

  16. Profile photo of Rosaliy Lynne
    Rosaliy Lynne 4 months ago

    Why do I crossdress? I never really came up with an acceptable reason for it. As a child I was always different but no one, not even I, understood why. In grade school, I did not relate well with other boys and never really got into boy activities. Oh I shot hoops, jumped rope, climbed the bars at the park, played cowboys and indians and other kid games but I just never really fit in.

    In high school, one day it just hit me, I had to dress as a girl. Believe me when I say I spent a lot of time trying to figure out why. I enjoyed the change of clothing but that did not seem reason enough after all, boys were taught not to wear girl clothes. Actually, I believe it was part of religious education that boys did not dress as girls and vice versa.

    So I decided to acquire some girl clothes. If the things I got fit I kept them to wear secretly and the rest I threw out. There was an element of sexual erotica too at first but that didn’t explain the need either and that was short lived anyway.

    I have always had a good eye for what to wear so it wasn’t a fashion statement. At first I enjoyed being the girl some times and then switching back to the guy.

    Guilt, fear of getting caught dressed that way, being teased or called names, those thins also figured in the mix and made in necessary to hide that part.

    The only thing I decided made any sense was that the girl side was part of who I am and since that was the case it could not be wrong. Not that simple though. It took years before I accepted that and embraced this other side of me. Eventually I realized that this is who I am and so here I am today, this lovely woman who still does not know why I started crossdressing but who now also realizes it doesn’t matter. I am who I am and that is good enough for me.

  17. Jennifer Elise 5 months ago

    Like you, I started dressing from an early age. 4 or 5 maybe. Truth be told, I can’t remember a time where I didn’t wear women’s clothes. Even when I was in the Army, I found a way. It certainly didn’t start out as sexual. At 4 I didn’t understand what sex was. It just felt right. It was the only time I felt like me. Thus is still the reason. It’s not that I don’t like men’s clothes, I just feel more comfortable in women’s clothes. I wish it were accepted. I hate that it’s even called crossdressing. Ellen isn’t called a crossdresser because she wears what are traditionally men’s clothes. I just want to be me, and I only feel that way in a skirt or dress.

    • Profile photo of Ricki
      Ricki 3 months ago

      I do agree we have a double standard when it comes to dressing .women dress in pants and shirts and lately in their pjs and it is acceptable however when a guy wears a dress the name calling begins . I love a dress and the freedom it provides far more than jeans or pants I guess if women are giving up dresses the we should do it for them lol
      Ricki

    • Profile photo of Tracey Rose
      Tracey Rose 3 months ago

      very true!

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