Dreaming to Be Michelle

By Michael Worthy

Published on Jun 4, 2005

Transgender

As you recall, Yvonne, my neighbor and I had just been to the movies and a club where she had me change out of guy briefs and into a little pair of pink panties, and we were going to the car to go home.

As we crawled into the car, Yvonne put her seat belt on and then turned sideways. As I began to back out of the parking space, she took her right hand and reached over to my crotch and began to gently massage the area. It took all of about 2 seconds before I was aroused. It was then that Yvonne said, "Wow, that was quick, we will have to slow that down if you are going to make me happy."

She then pulled away, knowing there wasn't too much I could do right now since I was driving. We chatted on the way home about a lot of things, some of which was a bit on the naughty side. As we talked on our 20 minute ride home, every once in awhile Yvonne would reach over and gently rub my male tool, just to keep me on the edge. As we pulled into the parking spot by our apartments I walked around and opened the door for Yvonne, just being the perfect gentleman.

Yvonne then kind of shocked me when she said, "Well, since it is pretty obvious you want to be my little lesbian lover, you need to go to your apartment and get your high heels, and make them your tan pumps. She then grabbed me in her arms and pulled me close and while sticking her tongue half-way down my throat, she grabbed my crotch and squeezed firmly. As she pulled away, she added, "Be at my apartment door in 15 minutes." She then turned and walked toward her apartment.

As I walked into my apartment, I was as excited as I could remember being in a long time, and I had no idea what was about to happen. The 15 minutes I waited seemed like the longest 15 minutes of my life. This seems like a pretty good place to tell you that at this point in my life I was very naïve about most sexual things. The only thing I was not naïve about it seemed was being both Michael and Michelle.

As the 15 minute mark approached, I headed out of my door toward Yvonne's apartment. As I got to her door, I saw a little note hanging on the door. I opened the note and it read:

"Dear Michael:

Come on in, there are instructions taped on the wall inside the door."

I wasn't sure what was happening, but as I walked in I saw another note taped on the wall, just as I had been told. This note read:

"Michael:

I have been thinking about this night for a long time, ever since I first saw you as Michelle, perhaps even longer in some ways. I want you to be my lesbian lover tonight. Go into my bathroom where I have an outfit and make-up for you to transform yourself into Michelle. Don't worry; you will be glad you did. I have also placed a glass of wine in there for you, so make sure you drink it, just to help you relax. When you are done, come join me on the sofa. There is no need to rush, I will be awaiting your arrival and I will give you an experience you will not forget for a long time.

Your Mistress,

Yvonne"

Well, one thing is for sure, the memory has stayed with me for a long time, and I am remembering it 25 years later.

Not really knowing what to expect, but knowing I could handle Yvonne if anything bad happened, I went to her bathroom. It was pretty clear to me as I walked toward the bathroom that she had been planning this evening, as there were candles burning and soft music playing. I walked into the bathroom and closed the door. There awaiting me was everything I needed to become Michelle. On the counter by the sink was all the make-up needed for Michelle, and on the toilet seat was a set of breast forms, pink garter belt, pink bra, stockings and a little pink teddy that matched my panties.

There was also a box about the size of a shoe box, with a note that read, "Open only after completely dressed and you have your make-up on."

I must admit, I didn't really follow the instructions exactly. I went ahead and opened the box. Inside was a long black curly wig. I could tell just by looking at it, it was going to go well below my shoulders.

As I stood there looking at all of my "new equipment" I once again became very excited.

I went about my task of transforming myself into Michelle as quickly as I could. When I finished I looked at myself in the mirror and was pretty impressed. I knew it was now time to see what awaited me. I opened the bathroom door and stepped into the hallway, and walked toward the living room. As I walked into the living room, Yvonne, told me stop! She then grabbed her camera and took a bunch of photos of me standing there in my teddy, stockings, and 4" tan pumps. When she was finished, I finally noticed Yvonne.

Yvonne was dressed in a black corset with garters, black stockings, and a pair of stiletto heels. She looked amazing. Yvonne then invited me to come and sit beside her. She handed me another drink and we began to have a little fun. Before long Yvonne invited me into her bedroom. I entered her bedroom for the first time. As we crawled into bed Yvonne told me to kiss her, as I moved toward her lips, she said, "No, I want you to kiss my feet."

I responded, "What do mean kiss your feet?"

Yvonne said in a soft seductive, but yet stern voice, "I want you to kiss my feet. I love having my feet kissed, it makes me get very excited."

Considering the situation, I immediately turned around and removed her shoes and began to kiss her feet. As I did this, Yvonne was gently massaging my ass through my pink panties. Finally Yvonne told me to place her shoes back on her feet turn around where I could kiss her breasts. Needless to say I complied.

I could tell Yvonne was getting excited as she stopped talking and was squirming around in the bed like a hyperactive snake. Yvonne then invited me to turn so I could kiss her private area and she could massage my now throbbing penis. I quickly complied.

As I turned I began to kiss her every so gently. I started slow and before long she was screaming for more. Meanwhile, Yvonne had taken my stiff penis into her mouth. She was treating it gently as if she did not want to injure or damage it. We continued in this manner for what in some ways seemed like an eternity, and in others just moments. I continued to get closer and closer to exploding in her when she suddenly pushed me away and asked me to get between her legs looking up toward her face. I quickly moved into my new position still not having relieved myself.

I continued pleasuring her with my tongue when I felt the pressure of her spiked heels press against my back. As she got more and more aroused the pressure from her shoes increased until I could hardly stand the pain. As Yvonne was about to climax she put her legs around my head and squeezed with all of her might, as her juices flowed out of her.

Meanwhile, my erection continued to stay hard, when Yvonne moved and began to massage me with her hand until I exploded with my cum flowing over her hand. Yvonne then took her hand and brought it to my lips and telling me to lick her clean. Here I was dressed as Michelle eating the juices of Michael, how ironic.

As I finished we both lay on her bed and held each other in our arms. Before long Yvonne said I needed to go home as I couldn't spend the night, I asked why.

Yvonne responded because we both needed to get some sleep as she had some special plans for her and Michael for the next day.

As I headed toward the bathroom to change, Yvonne said, "Why don't you just walk next door like you are, no one will see it 1 o'clock in the morning." Reluctantly I agreed.

I went to my apartment and crawled in the bed and fell fast asleep. About 9:00 AM my telephone rang. It was Yvonne.

She asked how I was doing, and I said I was doing great. She then explained that she wanted Michael to take her to the local county fair and then we would go to the lake. Just to keep you in place time wise, this was the Sunday before Memorial Day. So in another six days we would be having a long holiday weekend.

I agreed to go. She said we should leave about 11:30 if we wanted to get there, so why didn't I get dressed and come down to her place for breakfast in about an hour. Of course I agreed to that as well.

I showered and shaved and went over to her apartment right on time. I knocked on the door, and I heard Yvonne yell, "Come on in."

I opened the door and walked in. There stood Yvonne in just high heels and nothing else. Yvonne then commented, "Come here, I want you to get me as excited as last night, but this time you can't use your hands, so get undressed now."

Far be it for me to refuse an offer like that. I was pulling my shirt over my head when I heard her say, "Now, turn around and put your hands behind your back."

I paused for a bit and then I heard Yvonne say again, in a much sterner voice, "Turn around and put your hands behind your back."

I did as I was told, and in just a moment I felt something being placed on my wrists. It ended up to be a pair of handcuffs. There I stood naked as could be with my hands behind my back. Yvonne then ordered me into her bedroom where she assumed a spread eagle position and she instructed me to begin licking her sweet spot. As I began to get her aroused she once again began to dig her heels into my shoulders and back, causing me to moan in pain. After what seemed like an eternity of licking she finally let loose her juices, and told me to lick her clean. I continued, after all I didn't have a lot of choice. When I had completed my task, she unlocked my handcuffs and told me to do whatever I wanted and then join her in the kitchen for breakfast. As she began to get off the bed she leaned forward and once again gave me deep passionate kiss. As she left the room she closed her door.

I laid there on the bed for a moment not knowing what to do. I then got up and slipped on my briefs and shorts and walked into the kitchen, took Yvonne in my arms and gave her a big kiss.

Yvonne turned toward me and hugged me and said "Thanks."

She finished preparing a light breakfast and after we had finished eating said we needed to take a shower and get going. I said, "OK."

Yvonne took me by the hand and led me to the bathroom and said, "I think we should shower together."

I agreed, it was a great idea.

As we stepped into the shower, I caressed Yvonne and knowing how much she liked oral sex; I dropped to my knees and began to kiss her once again. She quickly began to shake and in just a few moments she let out a giant quiver and shot her load.

It was great to have this going on. Yvonne then remarked, "That was an unexpected surprise."

I said, "The last week seems to have been full of those." Yvonne just laughed.

We finished out shower and got dressed. Me in my shorts, and Yvonne put on some tight SHORT shorts, a little tube top, and a pair of platform wedge heels. We made a great couple.

We went to the county fair where nothing eventful happened and then on to the lake where we laid out in the son and got some much needed sun after a long winter. After all, we needed to get a good tan going for later in the summer.

The rest of the day was uneventful, and we both went to bed early that night alone. Why, I do not know.

The week progressed as normal until Thursday when I once again made my trip to "The Onion." I went in just some plain slacks and a T-top, whit some 3"heels. I spent the evening having a great time and being with people I had come to know. Ron was there, remember he was 6' 6" tall, and we had a great time. We talked about the past week, and all that happened. Ron talked about his family and that he had a wife and a 19 year old daughter. Ron's wife was only 36, so obviously they had their daughter at an early age. He also told me that his wife knew completely about his Thursday outings and that she was fine with it. He said she would rather he be with guys than with another woman. What really shocked me was that his daughter also knew, and she was OK with it as well. He went on to explain that his wife also had a set of friends that she would go out with on Thursday evenings. This information will be of value later.

As the evening ended I headed home. As I got to my apartment, I noticed a note on the door. I opened it and read:

"Michelle, why don't you come visit me for a drink.

Yvonne"

Needless to say I headed right next door. As I got there and knocked on the door I heard the lock being unlocked, and Yvonne opening the door. There she stood in her black corset and heels, nothing else.

We headed straight to the bedroom where once again I was able to bring her to climax without entering her or using my hands. Yvonne however did use her hands and mouth on me and got me to the point of release when she pulled away and used just her hands to "get me off."

Yvonne then invited me to spend the night, and of course I willingly agreed. I thought I had died and gone to heaven until the next morning when I suddenly realized I needed to get to work and I was going to have to walk to my apartment during the busiest time of day dressed as Michelle.

I quickly dressed as Michelle and headed to my apartment and got in without running into anyone I knew. I quickly undressed, showered and dressed for work. I headed to my car and was about to get into the car when I noticed a note on my car window. I grabbed the paper and opened it. Inside was a note from Yvonne. The note read:

"This is Memorial Day weekend and I know neither you nor I have any special plans. My parents' cabin on the lake is vacant this weekend and I would love for the three of us (Me, Michael and Michelle) to go there for the weekend. I will drive and all. We can leave this evening whenever you get finished packing, probably around 7:00 PM. I would prefer to ride with Michael. Mark yes or no and slip the note under my wiper blades on my car."

I knew my answer without thinking. I checked yes, folded the paper and slipped it under Yvonne's wiper blades just as I had been asked. I jumped in my car and headed to work, wondering what the long holiday weekend would be like. I also decided to pick up a couple of new items for Michelle to wear this weekend, a swim suit and some nice femme jeans.

I worked the day, but left a bit early and went and bought my new items, then went home and packed. About 6:45 the phone rang. I picked up the phone and heard Yvonne ask if I was about ready.

I replied, "I am ready for a great weekend and I have a couple of surprises."

Yvonne replied, "Well I am ready too, and I have one or two surprises for you as well, so come on let's go."

With that we loaded up the car and headed out on the two hour ride to a cabin on the lake I had never seen, both awaiting a weekend full of surprises.

Of course you will have to wait to hear more about those in the next piece.

Next: Chapter 4


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