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My Life as Michelle
My Life as Michelle—True Story.
Like so many others I have been cross-dressing since I was a young child. My mother used to store her clothes in my closet so I always had easy access to what ever outfit I wanted. More than that, I had a sister who was a few years older who always had the latest fashions so occasionally I would sneak some of her outfits as well. I used to sneak panties and bras from the laundry and occasionally would sneak out at night dressed and with makeup. As I grew up I began doing it less and less but still on occasion would dress in panties and a bra when I had the opportunity.
Over the last year my job had given me an opportunity to work in another state from where I live. I rent a lovely condo near the beach and now spend most of my week there and usually weekends at home with the family. As the weeks wore on I began to get the urge to dress again. I now had a golden opportunity to take it to the next level. I went online and ordered everything I would need from beautiful lingerie to makeup to breast forms. I was ready. Each day the delivery man came to the house there was a new surprise and it was wonderful. I started coming home each day and getting the heels from the closet inside the door and that would transform my mind into Michelle. I would go upstairs and without looking in the mirror toss my ugly man clothes and put on a wig. Once the wig was in place I would put on a bra and panties and then go to the bathroom to put on my makeup. I practiced shaping my voice and my feminine gait so I could be the best Michelle I could be.
I began to venture out for drives and then walks to a few local shops as the area I live in is very liberal and friendly to cross-dressers. As I got better at the look I began taking photographs and started a MySpace page. I even chose the best one and sent it off to Rene’s Prettiest of the Pretty site. I was chosen to be on the site and my photograph was placed on the site where it linked your photograph to your web page and your email. This is where things got interesting…
A few days after my photo was posted I received an email from a man named Phil. First I must state that I am not much into men although I have been curious. I guess I am a cross-dressing lesbian! Phil stated in his email that he thought I was very beautiful and that he lived near me. He was so eager to meet but I just thanked him and emailed back that I was not interested. The next day he emailed me again, this time with a photo of himself. Phil is a very handsome man! I again replied no. A few days passed and in those days as I dressed I would think about Phil. Each night as I would undress for bed I would lay down still in my lingerie and masturbate thinking about him and what would happen if I agreed to meet him. I closed my eyes and imagined him holding me. I dreamed about meeting him at the door and embracing. I dreamed of his strong arms around me as we hugged and I kissed him tenderly on the cheek as he came inside. All of the sudden I decided I wanted to meet this man.
So after about a week I received another email from Phil. This time he sent another photograph of himself holding flowers and wrote under it, “For You.” I gathered my nerve and slowly wrote back to him.
“Dear Phil, I think you might just be the sweetest man alive. I find myself thinking about you often and wondering what you would be like in person. I am thinking I like the fantasy of who I want you to be and what I want you to be like so I am afraid to ruin that for myself. Tell me you are as sweet in person as you are online.”
He wrote back to me and said, “Dearest Michelle, I think of you often too and I too am a bit afraid of ruining my dream of who you are and how you would be in person. I do think it would be fun to meet and find out for real. I will be at the coffee shop on Cookman Avenue tomorrow at 7PM. Please come see me.”
I shook as I read the email. I know I am not gay and I have never been even in the slightest way with a man before, but as I become Michelle each day I change how I think. I think about men and how beautiful they are. I think about my fragility and how nice it would be to have a strong man to protect me when I am out. I think how nice it would be to have a man come home each night eager to see me and to share my life with. I realized as I change to Michelle and don the attire and makeup that I really change and begin to think like a woman.
I decided I would do it. I called into the office and took the next day off so I could prepare. I laid out five different outfits and finally decided I would simply go in some very nice jeans and a sweater as it was the middle of October in New Jersey and I did not want to attract a huge amount of attention. I took a long bath and shaved every inch of my body and started getting ready for my meeting with Phil. I took extra care with my makeup and at about 6PM I finally decided I was ready to get dressed.
I guess I should describe myself. I stand a statuesque 6 feet tall with a swimmers build. My legs are long and strong and I actually have a very nice round butt! I wear a size 38C bra and usually wear a large size panty. I choose not to wear any shape wear so I look like an athletic woman I wear a few different wigs but my favorite is a layered ash blonde medium length wig. I apply makeup to make me look like a classy, stylish woman. Not the usual tranny bright blue eyes and bright pink cheeks for me.
So, I put on my favorite pair of lace boy short panties and matching push up bra. I have several shapes of breast forms and I chose the pair the allowed me to show the most cleavage, which was my goal for the evening. I gave up some size but the padding in the bras would take that up. I put on my semi-tight Claiborne jeans and a V-neck tank top which I covered with a lovely light pink cardigan sweater. I finished with a pair of black trouser socks and a pair of black 4” heel leather ankle boots. As I looked in the mirror a feeling of anxiety I could not describe came over me. I was looking at a beautiful woman in the mirror but I was terrified of going to meet Phil. Will he like me? Will he think I am pretty in person?
I looked at the clock and it was 6:45. Now or never. I grabbed my black Coach bag, threw in some makeup for touch up, grabbed my keys and ran out the door. I was on my way. I decided it might be easier for me if I knew Phil was already there. I did not have his number but I was hoping I could drive by and see him in the window. As I drove by slowly I did not see him and again I began the nervousness. I parked a few spots down the street where I would have a view of all who entered the shop. I did not have to wait long…
There he was. Phil walked across the street and I got my first in person look at this beautiful hunk of a man. Phil stood about 6 feet 4 inches and was built like an athlete. He had incredible salt and pepper hair that was gently wavy and done to perfection. He was wearing a very handsome leather coat and a fine fitting pair of Levis. His ass was tight and his walk was confident. The clock showed 7:02—time for me to go inside.
I took a long, deep breath and got out of my car. It took a few steps to get my walking rhythm down but I soon found a natural step and slowly made my way into the coffee shop. Phil had already been helped and was sitting at a table just inside the door. As I walked in he stood up extended his arms and said to me, “I am so glad you came to meet me.” I nervously approached and accepted his hug.
It was my first hug as Michelle. It was everything I had hoped it would be and more. I felt as though my breasts were part of me and the feeling as he pressed his chest into mine was incredible. I almost melted as he gave me a gentle squeeze. As we parted I followed his arms down to his hands and pulled back while grasping his hands. He said to me, “You are even more beautiful in person.”
All my fears and anxiety disappeared. I thanked him in my best Michelle voice as I sat to join him. He even helped me with my chair. As we talked my mind was completely oblivious to everything around me. I stared into his sparkling green eyes trying to see his soul. I found a wonderfully articulate and wonderfully sensitive man. Oh, forgot to mention how incredibly gorgeous he was too! He playfully touched my hand on occasion although he never really held it. I would have let him if he had.
I could not believe it. There I was, a normally straight guy with a normal life transformed into a beautiful woman and craving the attention of this gorgeous man sitting one seat to my right.
The hours ran away from us as we talked about everything from pets to world politics. I looked at my watch and realized it was midnight! I did have to work the next day so I told Phil it was time to for me to go. He stood and helped me again with my chair as I got up. Phil then opened the door for me and asked to walk me to my car, which I readily agreed to. I felt like a school girl as he offered me his arm to walk me to my car. We walked in silence. Thank goodness because I was in turmoil again. What if he tried to kiss me goodnight? What if he does not want to see me again? My answers came very soon.
I stopped on the sidewalk next to my car and said, “This is me.” He walked over and opened my door for me and kind of blocked me from getting in. He reached again for a hug which I so much wanted from him and as we pulled away he kind of grabbed me by my arms for a second to see what I would do. I reached down and grabbed his hands. He looked at me and said, “We should do this again soon.” I nodded approval, leaned over and kissed him on the cheek and thanked him for a lovely evening. His smile was priceless.
I got in the car and drove the few miles home all the while wondering if I would hear from Phil again. When I arrived home I went straight to the computer to thank Phil for the evening and to leave him my phone number. I could not wait to see him again. I turned off the computer and undressed for bed. This time I did not have to dream so much about Phil as I masturbated. I simply closed my eyes and saw and felt him for real. I only lasted a few minutes but I had the most intense orgasm I may have ever had. I collapsed in the bed and next thing I knew it was morning.
I awoke with a mess of a face and still dressed as Michelle. I never did that before but it kind of felt good. Of course the wig was a rat’s nest! I quickly changed and got in my drab clothes and headed off to work. I could not concentrate at all. For the first time dressed as a man I was thinking about a man. I could not stop thinking about his smile and his friendly demeanor. I had a full on crush.
Phil called that evening as I was cleaning the house. We talked again for about three hours. Not sure about what, but the time went by so fast. When I told him it was time to go, he asked to see me again. I told him, “Why don’t you come by tomorrow night at 7:00 and I will cook you a dinner you will never forget.” Phil eagerly agreed and I hung up.
“Oh No,” was all I could think. I just agreed to host a second date at my home on a Friday when I was supposed to be at my real home. The next morning I came up with a plan and called home. I told my wife I would have to stay to do some interviews of new employees on Saturday AM. I told her I would get home for dinner and stay home an extra day next week. She was fine with it and I went about making my dinner plans.
I skipped out of the office a few hours early that day and went home. I went instantly into Michelle mode and got ready for Phil. He was coming in just 4 hours! I got myself most of the way ready and went to the kitchen to get dinner started. I decided to make a filet with crabmeat, a brown rice side and fresh steamed vegetables. I made a quick salad and prepared everything for cooking. I did not think desert would be necessary.
I went back upstairs and tried to figure out what to wear. Second date. Really hot guy. Slutty or soccer mom? Maybe slutty soccer mom. So that’s what I did. I did my makeup a little bit hotter than when we first met and made my hair a bit wilder. I changed my underwear and put on a really hot pair of pink lace panties with a pink pushup bra and the same inserts I used before. I paid special attention to making sure I could show a little cleavage and not my inserts. I wanted him to see me a little bit hotter tonight. I touched up my makeup and added a little more glamour with some white and pink highlights. I then put on black thigh high stockings, a black skirt with a lace trim that was just above the thigh with a light pink button down shirt fitted for a woman. I put on a fun little black belt and I looked in the mirror. I unbuttoned one more button to show some bra and cleavage and decided I had done it. Slutty soccer mom! I put on some pretty pearl earrings and necklace, finished off with a shade of lipstick that perfectly matched my bra and panties, put on a pair of 3” heel black pumps and went down stairs to wait for Phil to arrive. As I waited for Phil to arrive I downed a glass of wine and tried to relax. I made up my mind that tonight was time for Michelle to come out of her shell…
Right at 7:00 the doorbell rang and I sprang out of the kitchen to meet Phil at the door. I opened the door and invited Phil inside. He again looked so handsome. He was wearing a nice camel colored blazer and black slacks with a flawlessly pressed white shirt. As he came in I gave him a nice hug and I think I surprised him by a quick peck on the lips just as we broke the hug.
He followed me to the kitchen where he handed me a bottle of wine he had brought with him. I poured him a glass and pushed him playfully out of the kitchen to the living room to wait for me. I brought some fruit and cheese out to him to snack on before dinner and sat down across from him to chat for a while. We polished off the first bottle of wine and were both starting to get a little loose. We could not take our eyes off each other. He was staring at my legs and as I leaned in to grab some fruit he would look down my shirt. I was noticing his chest too and took a few glances at his crotch noticing a slight bulge on the left side of his groin.
We flirted back and forth for a while and I finally jumped up to finish dinner. As I walked past him I took a quick look back over my shoulder and caught Phil turning and looking at my ass. I just smiled at him and kept going. Phil followed me to the kitchen and asked if I needed any help. I told him I had it under control but told him he could stay and watch. I had the meal plated and ready in record time and we sat by candlelight in the dining room to eat. As Phil opened the second bottle of wine my mind began to race. I hardly remember eating dinner as I was in a trance. This man had my blood pumping and my mind in a fog. We soon found ourselves back in the living room on the couch as we finished the second bottle of wine.
As I kicked off my shoes I kind of leaned back and stretched showing off my breasts. That is when Phil made his move. He leaned in front of and locked me in a stare. His right arm was around my back and his left found its way to my waist. I brought my arms down and with my left hand I pulled his head toward me as I rested my right hand on his arm. We locked into a full on kiss. I opened my mouth and his tongue found mine. It was so tender yet so firm. As Phil caressed my side I turned slightly to press myself against him. I was tingling all over. We broke the kiss and looked deeply into each others eyes again. I pushed him back and stood up. I moved in front of him and bent down to help him up. As he came up I pulled him toward me and we locked in a hard embrace and passionate kiss.
I could feel his cock pressing against my belly and mine straining against the fabric holding it between my legs and out of sight. I reached up and removed Phil’s jacket and tossed it away. I did not take my eyes off of his as I slowly knelt down and undid his belt. He carefully caressed my head so as not to disturb my wig as I proceeded to release his slacks. They dropped to the floor followed quickly by his boxers as I got my first look at this gorgeous man’s cock. Phil’s cock was so pretty. Yes, Phil’s cock was pretty. It was perfectly balanced and sized. It was about 7 inches and nicely thick. I stood back up and as I unbuttoned Phil’s shirt his magical fingers made quick work of my belt and shirt. I turned my back to him and he undid my skirt and let it fall to the ground. Phil reached around me a grabbed a handful of breast and my waist and pulled me back to him. I could feel his cock against the bottom of my back and my upper ass crack and I gently pressed into him.
I broke from the embrace spun around and pushed Phil to the couch. I leaned forward kissing him on the forehead. I continued to kiss his face, mouth, neck and chest and worked my way past his hard stomach. I looked up at his face and the look was incredible his green eyes were pleading for me to continue and I did. I placed my hand around my first strange cock and slowly began to stroke it. I took a deep breath and looked once more at Phil and locked my lips around his pretty cock. Phil moaned with pleasure as I continued to slowly lick, suck and massage his cock and balls as he slowly pumped his cock in and out of my mouth and hands. While this was my first blowjob as a giver, I had received many so I knew what felt good. He said to me, “Oh yes baby. Keep sucking my cock.” Did he call me baby? I loved that. It made me feel so pretty and girly.
It seemed like an hour had passed and Phil started breathing differently. I knew he was ready to cum and I wanted to suck every drop from him. I could not believe I was about to taste my first cum. Phil stopped pumping my mouth, laid back and in a nanosecond exploded his luscious juice into my mouth. I took his entire cock in my mouth and sucked and swallowed and kept going until every last drop was gone. Phil threw his head back in a show of relief and I crawled up onto his chest and put my head on his shoulder as I hugged him tight. He gently put his hand under my chin and pulled my face to his and gave me an incredible kiss. I knew the night was just beginning but if this was the last thing I had ever done I would die a happy girl.
After a few moments of kissing, hugging and fondling I stood up and took his hand in mine. I lead him upstairs to my bedroom which I had already setup with candles and a nice fire in the fireplace. Gas logs are awesome. I directed him to the bed and told him I wanted to freshen up a bit. I went to the bathroom and took a good look in the mirror. My makeup and hair were a little off so I touched up a little and went back to him. When I returned Phil was sitting on the edge of the bed. He stood up and I wasted no time getting to him. I decided to be the aggressor and grabbed a handful of his cock which quickly hardened in my grasp. I pushed him back onto the bed and began kissing him all over. I stopped briefly to suck and gentle bite each of his nipples which judging by the moaning of approval he enjoyed greatly. I was ready for him to take me.
I broke our embrace to get into the nightstand to retrieve a condom and some lube. I opened the condom and placed it on his cock. Phil knew what to do next. He flipped me over and gently removed my panties and tossed them aside. He grabbed the lube and gently began to lube his covered cock. Then he took his hand and placed it between my legs and found my “pussy”. As he massaged it the feelings I had were incredible. He slowly inserted a finger and then two.
I had never been with a man before and all I had ever had in my ass was a butt plug and the occasional small dildo. I was so nervous but I found myself able to relax as his touch was so gentle and so adept.
We kissed often as he slowly worked his fingers into me and I began to pump back and forth helping him. He removed his fingers and looked longingly into my eyes. I nodded approval and said to him, “I am a virgin so please be gentle.” He looked at me and gave me one more incredible kiss and then positioned his cock at my opening. Slowly he began to apply pressure and in an instant he was inside. I felt a little pain and a little burning and a tear formed in my eye which Phil quickly wiped away. Phil took his time and soon was completely inside me.
I so often wondered how it would feel to be treated as a woman and to have sex like a woman and how it must feel to have someone inside you and to feel that pressure and the weight of a man on top of you. It was incredible! I found myself in a state of pleasure that was indescribable.
Phil slowly began to make love to me. A slow in and out and I returned the favor by moving with him. I decided it was time to make this better. I looked at him and said, “Fuck me hard baby, I want you to fuck me hard now.”
Phil increased his speed and force and soon was pounding me like whore. I matched every move he made and as my ass expanded was truly feeling such pleasure as I never had before. Phil stopped for a second and rolled me over. I got on my knees, forearms on the bed and gave my ass back to him. He popped right back inside me and grabbing my shoulder began pumping my ass like a jackhammer. I reciprocated and kept talking dirty to him.
“Yes, Phil that’s it big boy Fuck my ass. Fuck my dirty little ass.” He seemed to like this and in just a few more minutes his body convulsed and he came hard for the second time in the night. As he was fucking me I had been stroking my own cock and just as he finished I came into my hand. As he pulled out of me, I rolled over and looked at him as I licked every drop of cum off my hands. He pulled me toward him and gave me another deep kiss sharing the taste of my cum. We laid there holding each other, kissing and touching in absolute silence for a long while.
I woke up and looked at the clock. It was 2:12 AM and there was Phil sleeping tenderly behind me in a spoon like way. My wig was in tatters and barely on. I sneaked out of bed and to the bathroom to see how bad it was. I quickly fixed my hair and actually removed my makeup. I did a quick shave of my face since it was getting a little shadow and went back to bed. Phil never really moved and soon I was in dreamland again.
I awoke to the sun shining through the window and Phil was beginning to show signs of life. I went to the restroom again and did a little to my face so he would not see the worst of me, fixed my breast forms, put on a short silk robe and returned. Phil had woken up and was sitting on the edge of the bed. He stood up and told me I was the most beautiful person he had ever been with and that he was absolutely head over heels in lust with me. I smiled and told him I felt the same. I leaned in and kissed him feeling his rough beard on my freshly shaved face.
I could not control myself with this man. As we embraced I again felt his cock hardening between us. I had to have more of this incredible cock. I pushed him back down onto the bed and quickly kissed his cock back to full attention. Ready for action again I sucked his balls and cock for a good 20 minutes before he was ready to cum again. I decided I wanted this cum on my face and just as he was ready to blow I pulled my mouth off and jacked his splendid dick until he came all over my face and chest. I used my fingers to wipe it off and licked up all I could. Then Phil bent over and licked off the rest of his own cum from every part of me. What a feeling to have his warm tongue licking and sucking every inch of my face, neck and exposed chest.
Knowing I had to get moving, I told Phil he needed to go. He reluctantly got up and retrieved his clothes from the living room and as he got dressed I watched every muscle and every inch of this man. He moved so deftly and as I pushed him toward the door he turned and gave me one last delicious kiss. I told him I would be back in town Tuesday and that he should make a plan to see me then.
As he walked out the door I felt a longing that I had never felt before. I am not sure if it is love or lust or just complete satisfaction but whatever it was made me want to spend every minute I could with him. I hoped Tuesday would come soon because I could not wait to see what he had planned for me.