First Time

I'll start with a description. I'm 46 years old 6' tall and fairly thin. Oh and I'm a cross-dresser that when dressed goes by Lisa. I have been for years. Don't know why other than it pleases me. I love the feel of stockings and garters and for a few years now have gotten to where I enjoy having a nice thick dildo in my rear. I've fantasized of the real thing for years but haven't tried it yet. Until now.

I placed an ad on a web site for a likely candidate. Many men expressed interest, some agreed to meet and after many, many attempts not one man showed up. I wish they knew the effort and work that we go through.

I ended up chatting with two other cross-dressers and they had experienced the same problem. We decided to rent a hotel room and each invite two other men as dates. If none of our dates showed up, we "girls" would entertain ourselves.

As our date night approached I used hair removal cream and a razor to remove all body hair and oiled myself for several days to make my skin silky smooth. On Saturday morning Jan one of the girls and I met in the room and cleaned each other numerous times, inside and out. We applied makeup to each other, on the light and subtle side but enough to show that we had definite feminine features.

Robin, the other cross-dresser that was to meet us called saying she was unable to make it. She also said she'd been unable to reach her dates and that they may show up. Jan and I decided to go on as planned. We began dress in our outfits. Jan wore a heavily boned white corset with shear white lace top stockings and 4" slip on heels with a shoulder length, flirty reddish blonde wig.

I wore a black waist cinching corset that Jan had to help me cinch and she pulled it extremely tight. It had a shear, sleeveless top that had a tight collar around my neck. I had D-cup breast inserts in a clear poly bra under the shear top of my corset. My breasts had prominent nipples and where actually a squishy rubbery exterior with a heavy fluid filled interior cavity giving them major bounce and wiggle. The shear top gave them a subtle yet shiny appearance.