Dreaming to Be Michelle -- The Early Years
I am not going to bore anyone with the first 25 years of my life; it is much like everyone who has ever had a desire to dress as a member of the opposite sex. I too would try on my sister's panties, high heels and panty hose. On occasion I even bought my own panty hose. Instead I want to begin my story at the age of 25.
I was single, a college graduate, and living in a relatively large mid-west town. There was a night club I frequented way too much. However, I was single and had a good income, so it wasn't really a problem. This particular club had a good university student crowd, but also a good mix of local town's people. They still had a live band 5 nights a week, and there was always a lot happening. One particular night the owner, Bob asked me if I would go to another bar in the area and borrow a couple of bottles of Vodka. They had an unexpected group come in that was drinking a lot of Vodka, and they had not gotten their liquor order that day. He said he had already called and made arrangements, so of course I agreed.
Bob gave me directions and told me who to ask for. Even though I had already consumed a couple of drinks, I headed out. As I got to the club, I noticed there were no signs and even though I had been by the place dozens of times during the day I never knew it was a club. I went to the door, and informed the man checking the memberships who I was and what I was doing there. He said OK and told me to go on in. As I waited for the other owner of this new club to get me the Vodka I noticed there were plenty of folks there, but not many females. As I looked closer at the few who were there, I noticed that they were guys dressed as females. It was then that I realized I was in a gay club. Let me assure you as soon as I got the liquor I was out of there. Me in a gay club, never in a million years.
Well, when I got back to my regular hangout one of the bartenders who were openly gay asked me how I enjoyed my trip. I simply responded that it wasn't exactly what I expected. He said, not to worry, it wasn't contagious. Over the next couple of weeks the bartender, Jim and I had a few conversations about this other club, called "The Purple Onion." Then one day, Jim, who I likedliked, invited me to join him at "The Onion" as he called it. He said, there would be no problem, and he would make sure no one did anything. For some strange reason I agreed to go with him.
The following Tuesday, Jim and I met outside "The Onion" and went in. We just sat and talked like two guys at any other bar. I was very nervous, but I handled it pretty well. One young gal, who was actually a guy, sat and talked with us some. Her name was Tina. We talked about her dressing and why she did it and how strange it felt for her. She explained that she would often go out in public as Tina and she had never had a problem. As the night began to draw to a close Tina gave me her telephone number and said if I ever wanted to come back again to give her a call, she enjoyed being with a date once in awhile. I said OK, knowing I would never go back there.
A few days later I was on the way home from work, and had to stop in a drug store for something, and for some reason I bought a pair of panty hose. When I got home, I got undressed as usual, and decided to try the panty hose on. As soon as I was in them, I got this huge erection, I was shocked. I spent most of the evening in those panty hose, and only took them off when it was time to go out for the night. But throughout the evening, I couldn't stop thinking about the panty hose and Tina.
The next evening I decided to give Tina a call to see what she was doing. We agreed to meet the next evening and we would go to "The Onion" for a drink or two. I agreed to pick Tina up at her place, or is it his place?. Whichever, I drove and got out of my car and walked to the front door. I rang the doorbell and the door opened. There in front of me stood a rather handsome guy, named Tim, who also happened to be Tina. I could not believe the difference. Tim explained he thought it best if he went as Tim. As it was, we decided to go to another club in town. While there we did a lot of taking. I was shocked at how aroused I got. The night ended and I dropped Tim off and went home.
A couple of days later I got home from work and opened my mail. In the mail was a gift certificate for a local store, for $100. Now this was 1980, so $100 was a nice amount of money. It was to a local ladies boutique. In with the gift certificate was a little note that read:
"I think you might want to use this some day. When you go to the store, just ask for Roberta, she will be happy to take care of you."
Tina
I didn't know what to think. Me, a straight male going to a ladies store, no way. Well, about a week later I was in the area of this boutique, it was 2:00 pm in the afternoon, so I decided to stop and see what this place was like. When I walked in, there were two employees in the store and a couple of customers. The older woman, in her 40s came up to me and asked if she could help me. I said, "I don't know, I was looking for Roberta who had something I was to pick-up." This woman then told me to wait a minute. In a second, the other sales gal came over and introduced herself as Roberta. Now Roberta was about 5' 4", with thinck auburn hair, and HUGE breasts. She asked how she could help me.
I handed her the gift certificate and said Tina had recommended that I visit her. I had no sooner spoken these words when she got a little twinkle in her eye. She said, Oh, your are Michael, Tina said you might be coming by, I am so glad you did. She then took me by the hand and led me into a back room. On the way she apologized, she explained not everyone was as understanding as she was.
Once in the backroom, she asked what I was looking for, I explained I had no idea; I had never done this before. Roberta then chuckled, Oh a virgin, I like virgins. She then asked that I step into a little dressing area and get undressed all the way to my underwear and she would be right back. She seemed to be gone an eternity.
It wasn't long before she came back and asked if I was ready to try on some new clothes, I kind of muttered and said I guess.
She then slid one little item under the curtain after another and told me to put them on. The items came in this sequence:
- panties 2. bra 3. breastforms 4. pantyhose 5. skirt 6. blouse 7. wig 8. shoes
Once I had everything on she asked me to step out. I nervously stepped out from behind the curtain. Roberta put her hands over her mouth and let out a little sequel, WOW, you make a great gal. She then led me to a full length mirror, and I do mean she led me, she had me in 2" heels, I couldn't believe how tough they were to walk in.
Roberta then said to wait there were a couple of other outfits she wanted me to try on. Well over the next 30 minutes or so I tried on about three different outfits. Finally, Roberta said she thought for my first outfit I should take the black leather pants, a long haired white Angora sweater, the 3 ½" black pumps, a long light brown wig, and of course the panties, bra, and breastforms. After the gift certificate, I still needed to come-up with some money. I agreed especially since Roberta had been so nice. I knew I would never wear it though.
I got home that evening and just put everything in my closet. Over the next week I looked at the stuff in my closet, and on one occasion actually put the shoes on and walked around my house in them. Perhaps a more accurate statement would be I stumbled around my house. Finally one evening, I decided to try everything on. I got it on, looked in the mirror and got a huge erection, at least it was huge for me. The next day I did something I never thought I would do. I called Tina and explained everything, and asked if she would mind coming over and help me get dressed and perhaps we could sit and chat.
Well, Tina agreed. In about an hour, my doorbell rang, as I opened the door there stood Tim. I said hi, I was expecting Tina. Tim responded, "Well I think it would be better if Tim was here tonight."
Before long Tim was doing my make-up and then helping me dress. He then had me stand in front of the mirror; I could not believe my eyes. I actually looked like a woman. Tim then said, let's go have a drink.
I said, "Are you kidding me, I can't go out in public like this."
Tim responded, "Sure you can, no one will ever suspect you are anything but an attractive young lady."
Hesitantly I agreed, thinking we were going to "The Onion."
To my amazement, he took me to a hotel not to far from where I lived that had a little jazz band playing, and said we could have a drink and talk, and the music would shield our conversation. I couldn't believe I was about to be in a hotel, dressed as a woman, sharing a drink with a guy. As Tim parked the car, we realized we were going to have to walk a bit, and I had just a little experience walking in heels this high. Tim watched me walk, and said, not to worry, I looked great, walked fine, and everyone would be checking me out. I probably should now explain that I am 5' 11' tall, and at that time only weighed about 15045#, with bright blue eyes, so I did look pretty good.
We walked into the club, and took a seat. The waitress came up and asked what we would be drinking. I was about to speak up when Tim answered, "I'll have a beer, and my girl will have a Tequila Sunrise."
"OK", said the waitress. "I'll be right back."
Tim then looked at me and said, I hope you didn't mind my ordering like that. I said, "Not at all."
We had a few drinks and chatted and finally Tim said, he thought we should get going to "The Onion" now that I had a little confidence.
I agreed. I also knew it was about a 15 minute ride and I needed to visit the bathroom, when it suddenly hit me, I was about to be going to the ladies room, which I had never done before. I told Tim of my dilemma, and he laughed. He said he knew that would scare the hell out of me, he then explained how I should handle the situation.
Well, after my trip to the ladies room, we headed to "The Onion" where during the course of the evening I drank some more, actually danced in my heels.,
I also met a goy named Ron while I was there. He was about 6' 6" tall, and weighed 240# or so. He was in great shape and rather handsome. and met a guy named Ron.
I guess we will have to wait till later to hear about Ron.Ron and I danced and talked, and had a great time together. Toward the end of the evening Ron said he hoped he would see me again as he had a great time. I simply responded that he might, as I seemed to be getting out more.
As you will find out later, Ron and his family will play a major part in my evolution.
Ron gave me a little kiss on the cheek and said good night. With that Tim asked if I was ready to leave. I responded, "I guessed so." We started walking to the car, it was then I realized how much I had had to drink and how long I had been in heels, which was way too long.
As we headed to the car, Tim said it was alright if I leaned on him, which I did. It was a very strange feeling to be walking in a parking lot as Michelle, in heels, leaning against another guy. We made it to the car and Tim drove me home and dropped me off without an incident. I made it into my apartment and got undressed and fell asleep, when I awoke the next morning, I knew something had changed in me, but I wasn't sure what.
A week or so went by and I knew I wanted to go out as Michelle again, but I sure didn't want to go out in the same outfit. With that in mind, I thought I would go shopping on my own for some "girl" clothes for Michelle, all by myself. I got dressed in my most male clothes and headed to a local mall. As I got there I began to think about everything I would need, another pair of slacks, top, and that was about all. I walked into one of the major department stores and begin looking for something for my "girlfriend". I found a sales clerk, a woman in her mid-30s. I told her I was buying an outfit for my girlfriend for our one-year anniversary of dating, and we were going to a nice dinner and I wanted to get her something really nice and sensual for her, not trashy for me. She asked what size she wore, and I said I wasn't sure. She asked how tall she was and how much she weighed.
I then paused for a moment and said she was a couple of inches shorter than me, and about 140#. She showed me a nice suit with a skirt, and I said she didn't often wear skirts. She then showed me a really nice tan three piece suit with pants and a long jacket. It was light weight, but since it was now early spring, it would be OK.
She then asked if she needed anything else to go with it. I said I wasn't sure, but perhaps a pair of shoes to match. She then said she was sure she could find something to match. Even though this was a major department store they prided themselves on total customer service so we headed off to the ladies shoe department. As we walked she asked what size shoe my girlfriend wore. I thought for a moment, as I had no idea what size to buy. Now I have small feet, as most of my features are. I wear a men's 8 narrow, so I thought for a second and said, probably a 9 ½ or a 10. The clerk, named Barbara, waited for a second before saying anything. She then said, "OK, I think we can find something for your friend."
In a few moments she came out of the back room, and said to me, "Michael, can you come here a second, I laid out some shoes and rather than carry them out, you can look at them here." Without thinking I walked toward her.
She then led me into the back room where the shoes are stored and said something I was not prepared for. Barbara said, "I have a feeling these shoes and outfit are not for your girlfriend, if that is so would you like to try the outfit on so we can make sure it really fits." I am certain my coloring changed, as I said nothing.
Barbara then said, "Its OK, you would be amazed at how often this happens, I have been doing this a long time and can read people pretty well."
I said, "Thanks, but what if someone saw me." She assured me it would be fine.
With that I stepped into a private dressing room and put on the outfit. As I was finishing dressing Barbara said I should step out where there were more full length mirrors and she would make sure everything fit OK.
I stepped out, and there were a couple of surprises awaiting me. First, there were three full length mirrors that I hadn't noticed earlier. This let me get a good look at myself, and considering I had no make-up on, my hair wasn't fixed and I had no breasts in place in looked pretty good. Barbara however recommended that I let the store lengthen the pants about 2" and take them in in the butt region, all at no cost. She said they never charged for alterations on new purchases.
The biggest shock however was that there was another lady there, an older woman in her late 40s, who was from the cosmetic area. This lady, Dorothy, was there to make sure I was using the right make-up to complete my look. I must admit I was very embarrassed, but when she was done, I felt pretty good. She matched my make-up to my complexion and gave me some tips for making my skin look as good as possible, all at no expense.
When Dorothy was finished, Barbara said I should change back into my normal male clothing. Once I had changed we walked back into the main part of the store. I paid for my clothing, shoes and make-up, and Barbara told me when I could pick-up my outfit. Since this was a Tuesday, she said it would be ready Friday afternoon. She handed me a card with her name and store telephone number on it, and said good-bye.
As I walked out of the store, I am sure others could see a new warm smile on my face, perhaps even a glow.
As Friday arrived, I arranged my work schedule to make sure I could get by the store in the afternoon. I called Barbara to make sure my outfit was finished. She assured me that it was. I arrived at the store about 5:00 PM, and walked to the ladies department. When I got there she had my outfit waiting. She handed me the outfit and said she hoped my "girlfriend" enjoyed the outfit. I said I was sure she would.
Barbara then said, "If you ever are looking for another outfit to be sure and call her as she enjoyed giving the best possible service."
She then asked where my girlfriend would be wearing the outfit.
I responded. "The Purple Onion, tomorrow night."
Barbara said, "Well, I hope she enjoys the outfit, why don't you bring your girlfriend by here before you go out, I would love to see how she looks in the outfit, and perhaps we could find something else for her."
I paused and finally said, "Are you sure that would be OK, don't you think someone will notice?"
Barbara said, "I am sure it will be fine, just come find me and I will take care of everything."
Needless to say this is all I could think of for the next 24 hours. I awoke on Saturday morning and took care of my usual chores and errands. You know the things you have to do when you are single, grocery shopping, laundry, clean the house, etc. Since it was now around May 1st, it was still to cold to go to the pool and swim, so I decided to drive out to a local lake since it was a little warm. I put on some shorts and a t-shirt and drove out to the lake with a six-pack in the car. As I got to the lake, there were a few people around, so I got out and found a nice sunny spot, sat down and opened a beer. I stayed there for about 2 hours and soaked up some sun and a couple of brews. All I could think of the whole time was Michelle; remember that is me, getting ready for the evening. About 4:00 PM, I decided to head back to my apartment.
On the way home, I stopped in one of the big name discount stores and walked toward their cosmetic area. It was there that I bought some long artificial finger nails, already painted a deep red.
I continued my drive home, and arrived there about 5:30 PM. I decided to apply the nails now, so I would not have to be in a rush and the glue could set before I started using my hands. As I applied the nails, I realized one thing; it is a lot harder to put them on than I thought. However, after a bit, I had them all in place. I then sat on the sofa to watch a little TV while the glue set.
The combination of sun and beer made me tired and I fell asleep and awoke at 8 o'clock. I knew then I had to get moving if Michelle was going out. I thought I would eat something before I got dressed. I then found out my second big surprise about long nails. It is a lot harder to do "normal" things with nails than without. I did manage to get something to eat, and then off to the shower.
After showering, I dressed in a pair of white panties with a matching bra, the breast forms of course, a pair of nude pantyhose, and then I did my make-up. I took my time doing my make-up, and with my new foundation I looked better than ever. I then stepped into my new slacks and top, and put my long light brown wig on. I was just about all set to go; all I needed was my shoes. I opened the shoe box and inside was my brand new shoes, 4" heels. I stepped into my new shoes and felt a strain on my calf muscles I had not noticed at the store. I grabbed the purse Barbara had sold me to coordinate the outfit and began to walk to the door. I then found out the addition of 1" to the height of the heel made a huge difference in the way I walked.
I also now realized I was in a bit of a predicament, my car was parked about 10 spaces away from my apartment as some fool had parked in my normal spot. So I began walking toward my car, and fortunately I made it there without incident. I backed out of my parking spot and drove toward "The Onion."
When I arrived at The Onion, it was later than I had planned so the parking lot was full and I had to park about 100 yards away. I was scared to death as I had never walked down a street by myself as Michelle. Of course since it was later than I planned I never made it to the store to let Barbara see me. As I got to the door, the individual checking memberships told me I was going to have to join the club, which I did for a modest fee. The fee was really to enable it to operate at all times and to keep certain folks who might not be friendly to the gay cliental out. As he filled out my membership card, he asked me what name I would be using in the club; it was then that I said it would be Michelle. In order to comply with state law, he said he also needed my mailing address. As soon as I gave him the required information he gave me my membership card, opened the door and said, "Thanks and have a nice evening Ma'am."
I walked into the club and saw it was pretty crowded, and there were relatively few seats. I walked toward the bar, and ordered a drink. As I waited for my drink, the guy sitting on the bar stool beside me stood up, and told me to have a seat. He then introduced himself and we chatted for a bit. The evening went on and I had a couple of drinks, danced some with a number of guys and was feeling pretty good. After one particular dance I returned to my seat, and the guy who had offered me his seat earlier was standing there and we were chatting when he suddenly placed his arm around me and gave me a gentle squeeze. I was terrified, and aroused, I didn't know what to do. My first thought was to excuse myself and I headed to the ladies room. When I came back, he was still there. We chatted some more and he was a complete gentleman. Finally, a favorite song of mine began to play, "Stairway to Heaven", and he asked me to dance. I agreed. As we danced, anyone who knows this song knows it has both slow and fast parts. As the last slow part started to play he pulled me close to him and let his left hand dropped down on my ass where he gave it a gentle squeeze. I left out a soft groan and he told me how I turned him on. I just moaned some more. When the song was over, they played another slow song and we continued to dance. By the end of this song I was tight against him with both of his hands gently massaging my cheeks.
As this song ended, I felt myself beginning to have a little pre-cum dripping from my little erect penis. I became terrified and explained I needed to get going. He asked if he could call me, and I said, let's just meet here again. By the way his name was Randy. He said OK, when will that be?
I responded, "I don't know."
He then said, "Let's meet Thursday, that is always a good night here. They have some great functions on Thursday so all the single guys can come here and then go out with their genetic girlfriends on the weekend."
I agreed to meet him on Thursday, which meant I was going to have to do some more shopping before then. I guess we will have to do that in another story.