This chapter may better fit in the cross dressing category, but I'm keeping it in Gay, as past and future chapters are gay stories. And this chapter does involve some hot gay sex. I recommend you read previous chapters first, if you haven't already, to understand the characters.
——————————————————
Tuesday at the office was awkward, to say the least. I avoided Diane and stayed in my office, scared of what she may say or do. Has she gossiped about my pictures in makeup and lingerie? My purple lace panties? that I couldn't get it up?
Late in the afternoon she came in and said "Rick, I've always been attracted to you and liked you. Friday night will be an opportunity to find out if there is any possibility for us to have an intimate relationship, or if your interests lie elsewhere. I expect you to show up in full makeup and dressed, at 8:00, OK?, and I may have a surprise for you."
I got home and popped a beer. As soon as I took a swallow there was a knock at the door. I opened it to find Sue who rushed past me carrying a package and saying "follow me, come see what I got you" and she ran back to my bedroom.
Sue was all excited as she pulled a wig out of the box. "This wig is a copy of Marie Osmond's hair from her diet commercials, let's put it on and see how you look."
She helped me put it on and it did look like Marie's hairdo, long, wavy brown hair. "You don't look happy. I thought you would love it. What's the matter?
"Sue, thanks. I know you you mean well, but I think I'm happy being a man. The fact that I've come to love sex with men doesn't mean I want to be a woman. The worst part is I've been discovered by Diane, my secretary." I told Sue about what happened with her yesterday and how she expects me to come over Friday night in drag and I've decided that will be the last time I dress up, and how I've decided to take next week off and get away alone.
"Rick, what will you wear? You have all the lingerie you need, but you don't have a dress. You are too muscular to wear any of my clothes. Would you like me to get you a dress?
I told her yes, and she agreed to come over Friday evening and help me get ready.
The week flew by with me putting in long hours getting work done in advance in preparation for taking next week off. I did find time to book my flights and make reservations near a quiet, desolate Florida beach.
Friday evening arrived and I showered, shaved my body, and rubbed lotion all over, enjoying my smoothness. Sue came in and said "you look good enough to fuck!"
I noticed my cock start to harden and said "I would rather stay here and spend the night with you." I put on my black lacy panties, pulled on my stockings, loving the way they felt on my smooth legs, fastened them to my garter belt, and then put on my bra and falsies. Sue applied my makeup. I was amazed at how pretty, and sexy my eyes looked. She brought out a black dress and I put on a dress for the first time. It was really short, showing off my shapely legs, low cut highlighting my created cleavage, hugged my figure, accenting my ass, and had loose long sleeves hiding my muscular arms. I put on my 4-inch heels and the wig to complete the look. Looking in the mirror I almost didn't recognize myself.
Sue said "you look beautiful!"and started taking pictures of me with her phone and my phone, "if you are never going to dress up again you need a few pics to remind yourself of how sexy you look."
I was thankful that my windows were tinted dark as I drove to Diane's. She lived in a high rise condo downtown, which meant I would have to navigate the lobby and elevators. I parked in the visitors spot and walked into and across the lobby to the elevators. My high heels were loud on the marble floors. I ignored the stares I was getting from the security guard at the desk, and got on the elevator and pushed '7'. I made it to Diane's condo without running into any residents, and knocked on her door.
She opened the door, letting me in, saying "you look even more beautiful in person. I love your hair! Come in and let me get you a drink. What would you like?"
She told me to have a seat in the living room and went to get me a glass of wine. She had soft, symphony type music playing, which I never listen to. It did create an interesting atmosphere, and, after all, I was dressed for it. I sat on the sofa, and found sitting for the first time in a dress, crossing my legs like women do, a little awkward.
She came in and handed me my wine, sat next to me, turned towards me putting her arm on the top of the sofa and said, "tell me Rick, when did you start dressing like a woman? Is it a long time desire? Do you wish you were a woman? Do you have sex with men?"
We drank wine and talked, probably way too much, but when you are dressed like a woman, everything is pretty much out in the open. We were half way through the second bottle of wine when the doorbell rang. She said "don't get up" and jumped up, answered the door and let Danny in. I wasn't expecting anyone else to join us.
He said "Rick, I'm shocked, but you look absolutely fabulous!" He sat down on my other side and Sue got him a glass of wine and we continued to talk. It wasn't long and Danny had his hand on my thigh. I should have pushed it off, but I didn't. Maybe it was the wine, maybe it was because it felt good and I welcomed his advance. He turned towards me, putting one arm on the top of the sofa, around my shoulders, and the other hand was now rubbing my thigh more aggressively, arousing me. His touch felt sensual through the thin fabric of my dress. Sue got up to get more wine and as she left the room Danny pulled me towards him and kissed me full on the lips. I welcomed his kiss and we kissed deeply as he move his hand up under my dress, finding my raging hard on. The scent of his cologne and his kisses had me very aroused. I thought of all the times I had made these same moves on women in the past, only this time I have a man making the moves on me, the 'woman.' He was in control, making the moves, and I found myself being submissive, allowing him to have access to me. He pulled my panties down, releasing my cock from my panties, and started stroking it, saying "you've got a great cock."
