How it Started...

I have been dressing since the age of 11. I sort of had the body for it. 5'7", 170 my whole adult life. The dressing started with my mother's shoes and evolved from there. I fit in most of her clothes, but eventually had to start my own shoe collection. My whole life I have been in the closet about it and never told anyone. Since I got married, it was became even more difficult to dress. Now, my only chance is when I go away on business or if the wife goes to visit family.

Upon graduation from college, I got a job at Morgan Stanley. I was new and energetic to learn and a gentleman named Steve took me under

his wing. Steve was 15 years my elder. He was a very nice guy, married with two kids and very successful at what he does. He climbed the company ladder year after year. I have been friends with Steve since the beginning. He was married when I started, so our hanging out was after work getting a beer. Years later, when I got married, we started hanging out as couples and later as families. We even went away on vacations together.

Morgan Stanley was always a fun office, despite the seriousness of what we do. Every year we had plenty of parties. My favorite was always Halloween dress up day. I loved seeing everyone wear their costumes and having fun. After a few years at the company, I thought that I would get in on the fun. It was the perfect opportunity for me to venture out as Patricia. I was 28 and single at the time. I was pretty good at dressing, even though I had never been seen by anybody that I knew. The time to take the plunge was now!!. I was not going to do be stupid in how I dressed to the party, instead I would dress nice. I had the outfit planned in my head and couldn't wait for the time to come.

The morning came, and I woke up super early. I showered and started to get ready. I painted my toenails hot pink. I sat down at the mirror and did my best "work" makeup that I could. Smokey eye, blush, light lipstick, mascara, eyeliner, and all. I glued on my medium length french manicure nails. I put on a pink lace thong and matching bra, with nude thigh highs. I wore my regular men's suit with a womens blouse on top. Large hoop earrings and all of my rings, bracelets and necklaces were on. I wore my shoulder length blonde curly wig. 5 inch black, platform, patent pumps finished the look. I thought I looked professional yet was having fun, like everyone else.

I got to work and plenty of people were shocked. They said that I looked great and couldn't believe the transformation. I said it's all fun. The day went by, I loved it. After work we went for drinks, and again I was in heaven. Next day at work, I got the you looked great from the ladies and that was about it.

Years later, my wife and I were in Vegas with Steve and his wife. The women were getting a massage and Steve and I were having a drink. There were people everywhere, and a couple of crossdressers had walked by our table moments earlier. I looked, of course. Both were good looking but obvious. I didn't say anything but I did notice that Steve was checking them out as they passed by. Moments later, "I have to ask you something," he says. "In confidence."

"Sure"

"Remember that time years ago when you came to work dressed as a woman?"

I froze. Of course I remembered. But why was he bringing this up now? "When? I don't remember." I said.

"It was Halloween"

I didn't know how to respond. "Ahhhh. Now I know what you are talking about. It was fun."

"Have you dressed like that since? What I am saying is that you looked pretty good. I doubt that it was your first time doing makeup, unless somebody had helped you with it. Do you dress like a woman often?"

I didn't know where this was going. I told him that I had dressed a few times in college for fun. That a girlfriend back then had taught me how to do makeup. He told me that I was graceful walking in those ultra high heels. I still did not have an answer. At the same time, I had never felt turned on by a man until right now. All his compliments and his interest in the female me was getting to me.

"Why are you asking? Did you like what you saw?" and I burst out in laughter to make it look like I was joking. But I really wanted to see what the answer was going to be.

"I did. You looked good. Honestly, I'd like to see you dressed like that again. Maybe show off those girly legs of yours this time." He was laughing but I knew he was serious.

"I'll tell you what," I said, "we have a trip coming up soon to Miami. Change the date a few weeks earlier to around Halloween and I will. No pictures and you do not tell anyone. Not the wives. Nobody. Jessica (my wife) will freak if she finds out!!"

"Deal," he says. "It will be our little secret"

I had about a month to plan. I had all the clothes but needed to decide what to wear and what to bring. We had our own rooms, so this was going to be a few days of dressing for me. I was going to take advantage of this chance. I would always dress on trips, but would only bring a couple things as I did not want him to wonder why I had two suitcases.

The day for the trip finally came. We were on separate flights. I landed in Miami and went to the hotel and checked in. I left my bags and went to the lobby bar that Steve said that he was at. I walked in, and he says to me "This is what you're wearing?"

"What am I supposed to wear?"

"You told me you were dressing for Halloween."

"Now? We're not at a party"

"Did you bring girly clothes?"

"I did"

"Meet me in the lobby at 7:30 dressed up. I am taking you to dinner."

I was nervous and excited at the same time. We finished our drinks and I went upstairs to get ready. I wasn't sure what was going on, but I was going with it. What was he thinking? Why was he so insistent on me dressing for him? I din't know but this was a chance to be sexy and I loved to be sexy and that's what I had the chance to do tonight.

I decided that my outfit was going to be more classy than slutty. I wore a knee length floral print dress, black tights to hide the little hair that I had on my legs, and black pumps. I did my makeup, styled my wig, and was ready. I was super nervous but excited at the same time. I was telling myself that this was not a date and that we were just having fun. I did not know what Steve was thinking.

I got to the lobby and was hoping that I looked presentable. He saw me and told me that I looked great, and that he had made reservations at the Capital Grille. Fancy, I thought to myself. We got there and ate and talked for hours. He never said anything about how I was dressed and never gave me a vibe that he was a pervert. I was enjoying the conversation, dinner was excellent and the general vibe in the place and from Steve was great. The waiter was even calling me maam. I was super turned on. Again, never into guys, but right now I was questioning my sexuality. After hours of sitting there, we finally left.

We went outside and waited for our uber. He took me by the arm and helped me into the car, as if I were his date. My mind was in overload. He told the driver where we were going and then opened his legs a little and his leg rubbed against mine. Without thinking at all, I put my hand on his leg and rubbed it a little. He got quiet and did not say anything. I was rubbing and he was looking at me. My hand went closer to his crotch which was as erect as it could possibly be. While I was starting to rub the area, I noticed that his pants had a wet stain. I leaned in and gave him a peck on the cheek. When he turned towards me, I planted my lips on his. We kissed for a few seconds and then he asked me to stop. I told him that I was sorry. He told me that he wanted me to know that he was not gay.

We got out of the uber, and I explained to him that I was not gay either. I occasionally liked to crossdress but had never been with a man, or on a date with a man. I told him that tonight was great and that I was just caught up in the moment. I knew that we were both married and what I did was stupid.

Steve looked at me long and hard. Gathering his thoughts, he finally spoke. "I am not gonna lie, I kind of liked being with you tonight. It's been a long time since the wife and I have had sex and it was nice that you were showing interest in me. You look great and it was a fun time tonight. I hope that you are not mad that I asked to see you dressed up"

I knew that Steve was as confused right now as I was. I could also tell that he was as turned on as I was, but was feeling guilty and afraid and scared all at the same time. I was also all of those things. "You are one sexy man," I said. "How about we go up to my room, have a drink and unwind? See where the nights goes."

"Sounds good," he said.

We went upstairs and I poured us a drink. We sat on the couch together and chatted for a long time. I finally kicked off my heels and put my feet up on the couch. I leaned back on the armrest and put my foot on Steve's crotch and started to rub his growing penis. I did not know where I was going with this. What I did know is that I wanted him, here and now.

Out of nowhere he leans over and we lip lock for what felt like 10 minutes. We kissed and kissed and exchanged plenty of tongue. I was unsure of what to do next. I started rubbing his cock through his pants again, while looking him in the eyes, I said "Take it out".

He undid his zipper and took off his pants and underwear. He must have been about 6 inches. I was stroking it slowly, trying to be sexy at the same time. This was all new to me, and I was learning on the fly. There was a good amount of precum on the head of his cock that I took on my finger. Looking at him, I put my finger in my mouth and sucked the precum off, provocatively. At that point, I got on my knees in front of him, and continued to stroke. I looked at his beautiful, shaved cock and decided that I was going to suck it. I put it in my mouth and he let out the largest moan ever. It was all the encouragement that I needed. I know that I was kind of awkward with my first blowjob, but he seemed to be enjoying it. It was not long before I could tell that he was going to cum. He did not say anything, but I could feel it. He was breathing heavier and heavier, and finally I felt the first spurt in my mouth and pulled his cock out of my mouth, but quickly put it back in not knowing where he should be shooting his load. It was spurting in my mouth and going right down my throat. The taste of cum was better than I had expected. I had tried to eat my own plenty of times, but never got up the courage to follow through! At this moment, I wish I had!!

I got off the floor and went to the bathroom and put myself together. I went back and sat down on the couch next to him. I gave him a peck on the cheek, he gave me a long, wet kiss. "How about we get to bed and talk about tonight in the morning?" he asked. I agreed. "Do you mind if I stay in your room?", he asks.

"I was hoping you would," I said. I changed into a red mini lace chemise with a red lace thong and off to bed we went.

I woke up the next morning feeling his cock rubbing my butt hole. I wasn't ready to be fucked yet. I had never even played with toys. I turned around and kissed him and jacked him off. That was all he was getting!! We got ready and went to our meetings with three clients. Later that night we returned to the hotel. Steve asked me if he could take me to dinner again. I told him that I would love that. It was the same as last night. Dinner, chatting, blowjob, cuddling in bed. We did this for three more days and then it was time to get back to reality.

Reality was setting in and on Monday morning I was back in the office. Steve and I went to lunch and chatted about what had happened. He told me that he was not interested in me if I was not dressed. I told him that I would not kiss him or suck his cock unless I was dressed. He laughed.

"So, do you want to go steady?" I asked.

He laughed again.

"I am asking you to be my boyfriend", I said.

"I already have a wife, so a girlfriend would be great".

So that is how my relationship with Steve began. It has been going on now for five years, and nobody has gotten wind of it. We are at the point where we tell each other "I love you". Business trips are more frequent, longer, and much more pleasurable. We go away with the wives, out to dinner and they have never figured out that we are in a relationship. I found true love where I was not looking for it. I didn't even know that I was gay. Who knows what's next. We will all find out soon enough.

To be continued.....