Met and started casually dating Linda one summer. We met through mutual friends. She was tall, shapely and blonde. We did the usual dating things - dinner, movies, parties etc and had a decent sex life which for some reason was never as passionate as it should have been - but we kept trying! We fit together well, looked great together and that seemed enough for us. I didn't date anyone else.
As we got closer to Halloween, we started talking about parties and costumes and I mentioned I'd crossdressed for Halloween before. 9 out of 10 women I'd met were definitely not interested, but she became very excited and suggested we cross dress. Literally.
Went shopping for a used mans suit for her and had it tailored. She was 6' tall in low heels so without makeup, her hair pulled back and her breasts covered with an ace bandage she was like 90%+ passable. Even had black business shoes and got her an overcoat. She was more excited than I'd ever seen her.
Even though I had my own clothes, she wanted to control everything. She bought me a couple outfits: two dresses, a cute cotton blouse, denim skirt. My low low heel pumps were OK. She "approved" my bra and breast forms but vetoed my padded girdle for plain panties. I wanted to wear black tights but she bought some textured nylons and some fishnets.
A few days before the first party, she invited me over to work on my makeup and nails. She put together a little kit for makeup and picked out nail polish. She also restyled my wig, which was long and blonde.
My instructions were to come to her house Friday night all dressed up. I had zero confidence applying the makeup and nail polish, so I begged two gg friends to help. Showered and shaved and headed over there. They
applied the makeup (including beard cover, which they weren't familiar with) and did a great job. They applied the nail polish, and added some hoop earrings and a string of fake pearls. And loaned me a scarf and handbag!
Went home and finished getting ready. Low heel pumps, textured nylons, mid thigh denim skirt and a pretty white blouse. Had a long, loose cardigan sweater/jacket to cover it.
Left the house just as it got dark and headed 30 minutes to her house. Brought a bag of boy clothes to wear home the next morning.
The plan was to go out fairly early in Boston. Linda drove, of course, and we headed down to the club district in Boston. Halloween was Sunday so some people were in costume but many were not.
Dressed fairly conservatively, and about the same height, most people took no notice of us. She took my arm, which was nice. But the lace hose were just sexy enough to make people look, and I heard "Is that a guy?" a number of times. This was a little humiliating, but Linda ate it up.
. Very few people had read her. She was holding doors for me, paying for drinks, talking to the hostesses: totally in charge. Being the sissy girl was kind of intoxicating as well: I was the pretty pampered - and protected - bird. I had drinks at a few clubs while she drank Cokes. I was very relaxed and happy - and a little drunk - when we headed home.
When we got back to her place she helped me take off my jacket. Then she brought me to her bedroom to take some pictures.
Don't remember exactly what happened next but we started making out. She pushed me back on the pillow and she unbuttoned my blouse. I took it off, leaving the lace bra in place.
She unbuckled my belt and I wiggled my hips as she pulled the skirt off. She got up, went over to her closet and started taking off her suit, carefully hanging everything up. When she was down to her boys briefs, she came back to the bed. She pulled off the stockings and then my panties. I'd been semi hard for hours and dripping precum.
She pulled off her briefs and slid on top of me. She was already wet as her hips rode mine. She pushed my arms back in the bed and leaned over and kissed me hard. It was amazing. I pulled my arms free and grabbed her hips and slid into her. She started riding me hard, her lovely breasts bouncing as she rode .
I started moaning like a girl, and she rode me even harder. I held back until she started to cum. It was the most intense orgasm ever.
We cuddled for a while. I thought I would be staying, but she had other ideas. She told me to "clean up, get dressed and go home." And she vetoed the idea of wearing boy clothes home: I put my clothes back on and left.
We went out again the next night to a big Halloween party (even better). She started calling and texting more often and sent me my pictures.
We went out like this every few weeks for months: movies, dinners, some dance clubs and a couple private parties with some of her friends, who were quite accepting if they didn't really know what to make of me. They generally seemed to assume I was gay and we were just friends. It was funny to be in the kitchen cleaning up with the girls while she was hsnging out with the dudes. I started doing aerobics to lose weight, tried growing out my hair, kept my eyebrows trimmed and my nails as long as I could for work.
She didn't wear the suit often, but dressed more butch/male: no makeup, sports bra hair pulled back. Each time, she told me when and where we were going, what I should wear, and to show up fully dressed. After our dates we went back to her apartment, and her seduction became more elaborate and the sex even more mind blowing. I would go down on her and she loved it. She always took charge, and we even got into a little light bondage when she tied my hands to the bedpost with ties.
We never went out on a regular date again. She started dating another guy, and I remained her side girl only. But I loved every second of it!