My Mom and Dad split up when I was 7-8yo. My Mom got some money but my Mom had to get another income to help. She decided she would go back to hair styling and nails, I guess she had done that when she was first out of High School.

Anyway my Mom used to use me for practicing applying makeup and nails since she hadn't done it in a long time. I was not happy to help her but my Mom bribed me enough to make it worth my while.

So several times a week in the evening we would go to her bedroom where she had a table and lighting to do the nails or makeup. For a kid I must have had the best looking nails of any one around. I remember I would try and mess them up outside in the dirt just to make them look like other kids.

Now the makeup was truly a "mind fuck" experience, sorry it's the only way I know how to put it in simple terms. The first few times my Mom worked on me was rather so-so but since it had been years it would take a few more times for it to all come back to her.

So I'm sitting there thinking one night when she is doing my face how much I really hated helping her. My Mom didn't have any family around and she didn't make a lot of friends after they split up, but why should I have to do this?

My Mom suddenly stopped and put her brushes down and looked at me with a smile. She seemed so happy and told me to look into the mirror. I was in total shock when I saw myself in the mirror. I looked like a girl somewhat, having short hair killed the total affect but none the less I could have passed as a girl looking at my face only. The final insult came when my Mom had to practice applying fake eyelashes. I never knew something like that even existed and we would get into fights as she applied those stupid things. I would blink or move, Mom would get pissed and then I would run to my bedroom and lock my door. My Mom would beg and plead with me to come out so she could finish, then she would take it all off. Well I had to give in because I couldn't get all that makeup off by myself. I had to go through that a few more times until my Mom felt she could do it on customers without any problems.

Finally it was all over and my Mom got her job at a Salon not long after. In fact she was so good she would have a few women come to the house, she didn't have to pay a percentage to the Salon. My life would go on, but there was another "mind fuck" waiting for me down the road.

Twelve years of marriage, two kids, and divorce. Was on my own for about a year when I met a gal one night at a party at a friends house. Her name was Lilly and she was recently divorced as well. She was trying to start over after her separation, she didn't have to work because her husband wanted her to stay home and take care of the kids. When I asked what she wanted to do as a profession, she said she wanted to get into cosmetology, she had done some of that back in her school days.

Not making this up I swear!

Well Lilly and I moved in together about Six months after dating. She was going to School for Cosmetology and had a very part time job, I worked a lot of hours so our time together was squeezed in at times. The sex was off the hook, just not enough of it with our schedules.

One day Lilly wanted to ask me something, I could tell something was on her mind but she didn't want to come out with it. Finally I wore her down and she told me. She wanted to put makeup on me as a practice for an upcoming Exam. The laugh came out of nowhere and I guess it was over the top laughter. No! I NEVER told Lilly or anyone about being the guinea pig for my Mom when I was a kid. Lilly just walked away, my laughter had hurt her feelings I know. So at that point I had to break down and tell Lilly why I reacted that way when she asked me.

Well of course Lilly thought that was so sweet of me to help my Mom and sure enough I sat there and let Lilly do the same thing all over again, right down to the fake eyelashes. Now new techniques came along and Lilly knew how to blend colors and when she was done I was once again a girl. Now just like before my short hair didn't give the complete effect but Lilly had a fix for that. She went to the bedroom and brought out a wig. Well I should have just said no and been done with it. I did my part, what the hell was the wig for? Nope, I sat there and let Lilly put the wig on and fix it to her liking.

Still not making this up!

She had me look in the mirror, very crazy to see your face totally different. Did I look like a girl, yes I suppose I did. Being in my 30's my face was still smooth and I looked okay I guess. Okay so lets move on to the next "mind fuck" session. Lilly is looking at me and all I want is to get everything off and put this behind me. The next thing I know Lilly is leading me to the bedroom, she's digging into her closet and then brings out this satin robe. I have no idea what I was thinking at this point. I'm standing there looking at myself in the mirror with Lilly beside me and she is smiling from ear to ear, of course I'm wearing her robe now.

Take into account I'm about 5'8" and weighed at that time 150lbs. Lilly's reaction is what really mind fucked me. I was more than willing to get the wig, makeup, and the robe off and go do my thing. I helped her, made Lilly happy, okay I should be done right?

So I'm basically standing there in what is known today as "full Drag" other than the fact I'm basically wearing my underwear under Lilly's robe. The next thing I know Lilly and I are standing there making out, her hand is working my cock and it's responding very quickly!

Soon we are on the bed with me on top of Lilly. I have a raging hard on like I haven't felt in years and I pull back the robe and enter her. Lilly is soaking wet and my hard cock slides into her base deep on the first thrust. I cannot even describe the fuck session we had at that moment. Lilly eyes are wide open looking into my made up eyes with mascara and eye liner

Lilly digs her nails into my back through the robe I'm wearing and I can still feel the pain of them pressing into my skin. I'm fucking Lilly hard and fast, something I never did until I was ready to cum. She wraps her legs around my waist as I pound her almost savagely.

Suddenly I'm ready to cum, this is something so over the top I can't control myself from cumming so soon. I tell Lilly I'm close and she puts her hands to my chest and pushes me back hard. My cock pops out of her and she spins around on her fours, taking hold of my throbbing cock. She puts the head into her hot mouth and jerks me at the same time. I explode almost at once, my cock pulsates as my cum shoots into Lilly's mouth. I look down to see Lilly trying to take my load, she swallows quickly but some runs out of the corner of her mouth. Lilly has never let me cum into her mouth until this moment. She looks up into my well defined made up eyes as I ejaculate into her mouth. She finally swallows my cum, I don't think she really wanted to, but it was like it was something she felt she needed to do.

We collapsed on the bed totally spent, at least I was for sure. I thought I had experienced many pleasurable moments in bed with women, this was another level of pleasure all together for sure. I lay there in bed with Lilly's robe still on in some fashion. Lilly came and lay her head on my chest and we crashed right out.

This would be the start of me cross dressing, at least for sex with Lilly. She went out and bought more things to wear for bed, that was her idea not mine. Stockings, bodysuits, and she even bought me high heels and boots to wear. I didn't refuse to wear any of it, I enjoyed the makeup she applied and the clothing she had me wear for sex.

At some point after all the "mind fuck" situations in my life, my brain just told me it was okay to want this. Lilly was the willing partner in this, she had taken me to another level of sexual pleasure. I couldn't deny I didn't like it or that I didn't want it now.

We went our separate ways about Five years later. We dabbled in role play and some mild bdsm along the way. It was truly a storybook novel that I would have a very hard time walking away from at the end. The only time we didn't fight was in the bedroom, but sometimes I think we took our anger out on each other there at times. Lilly would carve my back up with her nails and sometimes I would use the riding crop to her behind a little bit too hard.

Two years later I got married. A very nice woman and there was nothing wild to speak about from the sexual aspect. We made love and that was pretty much it. Ten years later we went our separate ways, our jobs kept us busy and she traveled a lot. Our divorce was over without one single argument, we still talk today after all these years apart.

Three years later I met a CD online. I had dated many women after my divorce and none of them were going to understand my sexual needs and fetishes I had acquired. Michelle was a very passable CD and "she" was more than willing to go along with my kink. Since I was now getting older, the days of the makeup wasn't working anymore, I just pictured "Mrs. Doubtfire" every time I looked into the mirror. My body hadn't changed much since high school and I was almost the same weight I had always been. I could still wear the sexy outfits along with the high heels, boots, stockings. Michelle and I would go shopping and bring home things specifically for the bedroom. The biggest adjustment I had to make was the fact that Michelle had a dick regardless of what we did and how good it was.

Michelle reminded me a little of Lilly, "she" always had an idea of trying to take the sex and little further and a little darker. Michelle loved the riding crop, I was more than willing to use it on her. Then one day Michelle told me she wanted me the same way I had been inside of her. In my mind I had to decide what I was willing to do to allow me to satisfy my kink with Michelle. It took a while but finally Michelle and I were taking turns fucking each other along with the kink.

We got into a little bit of Cosplay, Michelle's idea. I wasn't a big fan so I steered her into Latex, which she absolutely loved. We had Latex hoods and bodysuits, we even had Latex sheaths for our cocks. We got a video camera and posted our kinky sex videos to a few Online Porn sites. We would play our previous sex video while we sucked and fucked and whipped each other under the cloak of Latex.

That lasted for Five years. I came home from work one evening, Michelle and "her" things were gone. No note, no nothing, just gone! Of course I tried calling Michelle a few hundred times I'm sure, without any response.

I moved out of State and met a woman named Cheryl. She was 55yo with the mind of a 30yo. To be honest I wasn't expecting anything much in the bedroom besides lovemaking. Usually by her age any ideas of kink would be totally out of the question. How wrong I would be. I had to tell her about my fetishes one night when we had a few too many drinks. I told her I liked a woman to dress up a bit for sex, outfits, heels, etc. I also told her that "sometimes" I liked to dress up as well. I could tell she wasn't really sure what I meant, but she said she was willing to find out.

Our first night together was a shock for Cheryl when I came out in this black Lycra bodysuit and knee boots. But it wasn't a horrified shock, it was like a surprised shock in a positive way. Cheryl and I had a great night of sex, it was so nice to put my cock into a woman again with a vagina. Her breasts were large and I made up for lost time not having them to enjoy.

Still telling the truth............

After a few months Cheryl came over one night and surprised me with "several things!" She opened her bag and there in her hand was a wig. Along with the wig she had her makeup case and she sat me down and went to work on me until the fake eyelashes were on to her licking.

Now I NEVER told Cheryl about the makeup part! I told her I liked wearing the sexy things and was partial to a bit of bondage, I didn't dare tell her I was into bdsm. Cheryl wouldn't have understood that and would have ended things between us right then.

I'm not going to say I looked good with the wig and makeup on. I was smart enough to know that time had come and gone years ago. However, Cheryl was so turned on by making me up we barely made it to bed, sometimes we didn't!

The sex was fucking incredible, Cheryl could cum multiple times over. I have never been with a woman that was as wet as she was once she was worked up. I began to shop online for us, to buy sexy outfits and a few pairs of boots for both of us to wear. The woman that thought I was a bit crazy wearing heels in boots in bed, was now shopping on her own to buy them as well. She would sometimes call me from the store so excited at the high heels or the boots that she had bought.

The relationship ended about a year later. For all the great things about Cheryl, the one big negative was the fact she was insanely jealous and insecure. If "any" woman spoke to me or looked at me out in public, Cheryl was convinced that woman and I were going to have sex at some point. We began to fight more than we fucked, I tried explaining I wasn't going to fuck a total stranger or vice versa. Cheryl just got it in her head it was going to happen and it got too much for me. I ended the relationship.

So now I'm single and have all this fetish wear. Sometimes I will put some of the things on and satisfy myself with a bdsm movie. Obviously not the same. I thought about going back to Craigslist and finding someone, but I know I can't do that anymore. I don't know why, but I just know I would back out if I were to meet someone.

The last thing. The other day my Ex Wife called me and was wondering if maybe we could talk about getting back together. Since we will be both retired, maybe we can enjoy each other this time around. I won't be working double shifts and she won't be going out of town on anymore business meetings.

Today I took the box of boots and outfits and donated them to Goodwill. Boy is someone going to be surprised when they open that box. I never started out with this fetish, so maybe it's time to move on and enjoy other things now.

Thanks to all of you that stuck it out and read my Story, I hope you enjoyed reading it as much as I did taking a erotic trip down Memory Lane.............