It's no wonder I grew up weird. A set of older triplet sisters, a pilot father who was away more often than he was home and a mother who seemed to resent most males. My earliest memories are of my sisters dressing me as if I was one of their dolls. By the time I was 16 my sisters had moved out to attend college, my father was home even less as he was piloting international flights to pay for three daughters at college and it was just Mom and I. She mostly left me alone but when she said jump I waited for the order to come down, she was not a woman to cross.

I have pretty fair complexion and I have to say it but my face does have a girly look. My arms are thin and my fingers long and slim. I play some tennis and golf so I'm not bulked up with muscle. I hadn't even shaved yet as I had very little body hair and what I did have is very pale to match my blond hair. I know from my days of being made over by my sisters that it did not take much work make up wise to transform me into a passable girl and I even remember them taking me out once dressed up as their little sister.

Like most young guys discovering sex I started with cheap porn mags with pictures of cheap women then moved on to better books with better pictures of better looking women. Being left at home alone gave me the chance to move up to videos and I spent many an afternoon jerking off to my favourite vid sex. I don't know how you acquire a fetish but I found my jerking off sessions were more intense if I had some of my sisters underwear with me at the time. Eventually I was wearing their panties when I masturbated or sleeping while wearing a pair of pantyhose. I didn't actually think of them when I was doing it but they had so many different styles and materials and the feel of the fabrics on my cock was so much different to my basic cotton underpants it just seemed to add to my enjoyment of jerkin' off.

My sisters had not taken even half their clothes when they moved out using the house as a free storage locker. This was fine by me as I had access to all of their stuff and I was careful to wash anything that got stained and ironed and put back. Then came that day. I had got a new vid and was anxious to check it out. The girl on the cover was wearing a skirt and blouse combo that were a close match to some clothes of my sisters so I was going to dress up in the same outfit while I watched it. Mom yelled at me that she was going out and would be back later so as soon as the car left the drive I was in my sisters room getting my outfit together.

I put on a crisp white blouse and a short red and black checked, pleat skirt. I could see some of her red panties in the cover pics so I found a pair that looked the same and I then added some thigh high stockings but as I'm not that tall I pulled them nearly all the way to the top of my legs. I went to the TV and popped in the vid and sat back to enjoy the afternoon. Wow, it was amazing how close I had got the outfit. One thing I never was into was bra's so while the woman in the vid had tits busting from a bright red bra that stretched the fabric of her blouse I stayed flat.

I was so into watching this woman do a slow strip pole dance that I didn't hear my Mom come back in. I don't how long she watched me watching the vid but suddenly she was between me and the television and she looked set to explode. She called me everything from sicko, to pervert, to creep and I dashed out of her way as she made a grab at me and headed for my room. I slammed the door closed and sat an the floor with my back against it to stop her pushing in.

Mom was rather subdued when she talked to me through the door explaining that she just wanted a quiet chat about sex and that maybe we should have had that talk earlier. It fooled me because I expected her to rant and rave all afternoon and try to kick the door in. I cautiously opened the door and Mom pushed her way in glaring at me with a look to kill. Her breating was deep and loud as she tried to hold her feelings in check. Amazingly we did talk in a mostly civilised way for about ten minutes until she asked about why I felt the need to dress like one of my sisters. I was mumbling some answer when suddenly Mom grabbed my arm and dragged me into her room and sat me down at her make up table.

Next thing is I'm in the middle of a whirlwind of activity as my Mom applies makeup to me and works at my hair. Then she rushed from the room and was back seconds later with a small lacy bra that had the cups filled with padding and told me to put it on then she was gone again and I could hear her in the girls room rummaging in the wardrobe. I put on the bra and replaced the blouse as Mom came back with an assortment of shoes and boots for me to try on. I tried walking in several pairs until Mom settled on a pair of white boots that came to just under my knee. They also had a chuncky cube heel that made it easier to walk. Finally she gave me a small purse to sling from my shoulder to complete the outfit. As I turned to face her the repeated flash from her camera nearly blinded me. I felt calm and relaxed as Mom gave me the once over and a slight nod.

She took one more thing from my sisters room and then took me out to the car. I got in while trying to see if any neighbours were looking but it was all clear. As we drove Mom told me that I was to do whatever I was told to do when we got to our destination and not to let on that I was a guy as it might not be exactly safe. My calm face was now a worried one and as we pulled into the carpark of a bar I was scared. Mom handed me a pair of glasses to put on. They had belonged to one of my sisters who had wanted to look smart so wore them even though they were not perscription.

The bar was dark with small down lights in the ceiling providing illumination. The room had about fifty people in it mostly guys, but some women, everyone looked like they were on a break from an office for lunch. Music played in the background and a few people were dancing. Along one wall almost in complete darkness were a row of booths. Mom ordered some drinks and found a table. She told me that if I wanted to be like my sisters then this was the place to start. No sooner did she finish talking when I guy came to our table and asked if anyone wanted to dance. Mom explained that we were here for some "lunch" and we had to be back at the office in an hour so we could only do some "regular" dancing. The guy nodded as if he understood and then reached for my arm. I looked at Mom but she just grinned as he led me away.

He was a head taller than me and from his shirt it seems his name was Mike and he worked for a construction company. We arrived on the dance floor as a slow number started and he held me in tight and just swayed to the beat. One hand held me in the middle of the back while his other hand drifted lower and slipped under my skirt grabbing a big handful of my arse. He moved his hand over the material of my panties and ran a finger along my butt crack. I squirmed a bit which he took to mean I was enjoying it. Now his other hand slid down to join the other and holding a butt cheek each he lifted me level with his face and planted a sloppy kiss on me forcing his tongue in and swirling it around my mouth. Gross.