An overview on how hard it can be for men who like crossdressing.

Since I began working in the adult industry online and offline nothing surprises me anymore. This first article on Crossdressers will show you how hard it can be for me who like crossdressing. In future articles I will explain more about Crossdressing and also cover guys who crossdress on a full time basis.

I was first approached to see a guy who was keen to allow his fantasy and his reality creep into one by coming to see me just so that he could allow the woman inside him to come out.

No he wasn’t gay. He had always wanted to dress as a woman, right down to wearing a wig to hide his short dark hair, he wanted me to help him with his makeup and of course there was the need for him to feel ok doing this too.

I certainly was not going to deny him the need to change into his women persona for a few hours and if he had wanted to go out for coffee I would have gone with him also. For many men they have a problem being able to express themselves unless they have a partner who understands or a good friend. However in a lot of cases the crossdresser can not express himself freely because he doesn’t have the support from family and friends. A lot of men tend to dress up at times when they are alone.

Who is there to help them enjoy it?

Let me tell you about a couple of guys, not just this one that I was talking about but others. I’ll call the first guy Bob because we do need to protect his privacy in all this. Bob is a guy who loves to dress up. The only problem is his partner gets totally pissed off with him because he likes to try on her panties, bra and sometimes her clothes. A few years ago before he came to see me was home alone on his day off when he thought he would try on her new teddy that he had purchased for her.

It was white and lacy and felt wonderful against his body. It was then that he thought he’d try her makeup also just to add to the moment and he found himself in front of his partner’s makeup mirror carefully applying a little lip stick. It was a colour that wouldn’t be too noticeable. With his back to the door he was lost in his own little world… that was until he looked again in the mirror to find his partner standing behind him with a look on her face that told him she was not a happy camper.

Bob stopped in mid application and turned to face her. Her face was as red as his and when she turned and walked out the door without saying a word his heart skipped a beat. For some reason he should have been embarrassed by her walking in and catching him but he wasn’t. His cock had become erect and yet deep down he knew that his partner was not impressed.

He then decided that the best time to try on women’s clothing was not in his home but somewhere else. The problem was he didn’t know where else he could go so he packed away his fantasy and his love for women’s clothing. But deep down he knew what he wanted to do and often found himself, looking and touching the sexy lingerie at the adult shops and other places wherever and whenever he could.

That was how he found out that I was open to most things and he could talk to me. First up a good friend of his, Pete, called me and told me about Bob. Pete was not a guy in Bob’s circle of close friends and family but he knew him and he obviously felt comfortable talking about it and it was decided that Pete would call me.

We had an interesting phone call because I needed to know all the particulars about Bob before I said yes to what he wanted to do. I found that Pete had helped supply him with some clothes, a couple of wigs, makeup, nylons and heels to help get him started. Having only tried on his partner’s clothes before he had none of his own… so he had to start from scratch…

With an appointment made Bob came to see me. At first he appeared somewhat nervous but once I showed him that I was ok with what he wanted to do, he relaxed… To cut a long story short, I allowed him to be open with what he wanted to do. Dressing up as a female is not an illness it is something that is quite open to some people. Just because he loved dressing up in sexy lingerie wearing a little makeup he wasn’t going out hurting people.

I believe that some people look at Crossdressers as being the work of the devil. Well guess what folks; it’s time you lightened up a little. These men are normal men with fantasies that they like to see become reality and some do achieve these fantasies while other guys with other legal fantasies leave them bottled up and never live them.

With many crossdressers in the world Bob is only one of them. He likes to wear the wigs and really dress up, however he hasn’t ventured out into the real world yet in his attire. I feel that he decided to keep his secret locked away because of his partner finding him. She has never discussed that day which makes it harder for a person who has such a fantasy.

From Bob, I’ll take you to a guy I call Gregory. Gregory is a hell of a lot different to Bob, because his partner knows that he likes to dress in women’s clothing and lets him do it too. She even goes out of her way to help him find some lovely lingerie and other goodies for him to wear.

He is yet to wear his new attire on the outside though because he is still not comfortable with the ‘world’ knowing what he is wearing. More often then not, this kinky guy who is also into the BDSM scene will wear nylons and lace panties under his work clothes.

He will wear them to work, to his family gatherings and on special outings with his wife. To me nothing is strange any more and I quite enjoy helping men live their fantasies, allowing them to be open with me and having a damn good time.

I’ll tell you about a truck driver guy I know who also loves to wear women’s clothing next time. I have to admit that I found him to be pretty cool. I also found that it amazing that he is also into the BDSM scene and I have been known to use my riding crop and paddle on his cute lace covered ass.

When it all boils down to it, some men find it harder than others to enjoy crossdressing because they do not have the support that other men have.

Support and trust is very important for a lot of crossdressers…

Leave a Reply