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My crossdressing transvestite dream girls! I had nowhere to put them. All the time, I was still one of the lads, I had many girlfriends and I kept my crossdressing transvestite secret hidden.

I suppressed it for a while. I got married and have a wonderful wife and a couple of great kids. I love them dearly, but I still have the same inner feelings!

I now know so much more of this crossdressing transvestite world. Could she help get rid of the guilty feelings and give me the feminine outlet for which I craved?

I put it off a few times and then plucked up the courage to call. I booked a day off work, but planned to travel overnight, allowing myself the luxury of going straight to a hotel after my visit.

I knocked at the door, and when it opened I met my JJ for the first time. She was gentle, supportive, understanding … and so completely sexy and appealing to all the senses: true sensuality with a wonderful clear-headed intelligence and fun-loving personality to match.

This was the start of my crossdressing transvestite dream becoming a reality. I stripped from my male clothes, and stepped into the crossdressing transvestite unknown.

I was guided to the bathroom, a bathroom with candles, feminine scents, perfumes, and cleansing lotions and face masks, I was about to start my journey, the crossdressing transvestite journey to find out who I am, who Cassie is.

After cleansing my face, JJ had run me a luxurious bubble bath. Finally, my Mistress brings me my dress. But it becomes very clear as she starts putting it on me.

I can only move my forearms. Feeling more helpless than ever, I moan submissively in my gag. As I do so, I am lost in dismay.

Her name is Jessica. On the contrary, I tend to prefer younger women. I leave my house and after a little while, I arrive at her sorority house. Please come in and follow me.

I walk towards the chair to have a closer look. I am completely blown away! My mind races to try and find a logical explanation to this nonsense.

I got a scared feeling and wondered if mom had grown tired of my little hobby. She smiled at me, Honey you know I love you, both David and Rachel.

I felt better after she said that. Mom smiled again, I need to talk to you both, David and Rachel.

You see dear I have to go to LA for the summer to help with the new office my company is opening. I will be there for two months the whole summer.

They have a condo that they are letting me use. Now you have a choice to make. We can continue as we are with David during the week and Rachel on the weekend but it may be really hard on you.

You can also be just David while we are down there. I looked at mom. I know it would be hard I said as I could see where this was going.

There is one other choice; you could be Rachel for the whole time. I was about to say something when mom stopped me.

Just wait dear she said, before you make up your mind if you do choose to be just Rachel for the summer I can help you but it will not be as easy as being Rachel on the weekend.

I thought about it and I really liked the idea. I really want to. Mom gave me a big hug. I want you to know it will not be all fun and there will be some problems but I will help.

If you are willing it should be fun. Then she gave me a kiss I will enjoy having a daughter all the time during the summer. I smiled at her. Mom I do want to be Rachel all summer thank you for letting me.

Mom told me she would make all the arrangements for the summer. The next few weeks all I could think about was being Rachel all the time. Wearing makeup every day and pretty dresses my life was perfect.

My last day of school was Thursday and it was only a half day. When I got home mom was waiting for me. Are you ready dear to be my daughter?

Yes mom I said with great enthusiasm. If we proceed from here on in you will be Rachel my daughter till we come back home. That means I will treat you like my daughter and you must act all the time as a girl.

Are you ready for that? My love of makeup took over as all I could think about was all the makeup I would be able to wear.

Mom smiled at me but it was a smile I had not seen before as she took me upstairs to start my transformation. In my room were several boxes. When I looked in the first one it had a pair of very realistic breasts.

Mom had me lay down and she glued the breasts on my chest. The feeling was strange as I stood up without a bra on. She gave me a kiss on the cheek and smiled from now on you will be my daughter.

Tagged with daughter , help , makeup , mom. Two Girlfriends. My name is mike and I am 17 years old.

I have never had much luck with girls as I am rather small for my age. I have found most girls like guys who are tall so when I met Mary at the start of my junior year and she liked me I was so happy, my first girlfriend.

Mary is beautiful with long blonde hair, long nails and the same height as me. Everything was great till Thanksgiving.

She was going out of town to spend it with her grandma while I stayed home and spent it with my mom and sister Jill. They do all the girl things together including getting their nails done.

The Friday after Thanksgiving I went to the mall to look around. As I was leaving the mall I noticed a girl standing by her car crying.

I let her use my cell phone to call her dad and he said he would be there in about thirty minutes. Turns out she is also 17 and a junior at Grant High across town.

I liked her and could feel an attraction to her which made me feel a little guilt when I thought about Mary. Her dad thanked me for my help and I left.

Hi Mike this is Susie, the girl you helped today. I was caught off guard but managed to say hi. I want to thank you so much for helping me today.

She said she would pick me up at 5 and thanked me again. As I hung up the phone I saw mom and Jill looking at me and all I heard was mom say, did you forget about your girlfriend?

I suddenly realized what I had just done but played it down. She just wants to thank me as friend. Mom just gave me that look.

Saturday night Susie picked me up, she was wearing a very tight red dress and heels, her hair and makeup were perfectly done and she had on this incredible perfume.

As we were leaving I saw mom look at me and whisper, just friends? I knew what she was thinking. At dinner Susie would touch my hand or arm whenever she could and every time I got a little chill.

I had such a great time I forgot about Mary. When we got back to my house I thought she would just drop me off but she parked and got out of the car.

We stood in my drive for a few minutes talking then she closed her eyes and leaned towards me. As our lips met she wrapped her arms around me and gave me such a kiss.

After about five minutes she got back in her car smiled, I had a great time Mike I will call you tomorrow.

I walked into the house and mom and Jill were standing there just looking at me. I knew what they were thinking but told them we were just friends.

Jill smiled at me; I wish I had a friend that kissed me like that she said. Mom just smiled so you are going to tell Mary about her.

I told her no there was no reason for Mary to find out and made them both promise not to say anything. Well as time went on I found I had two girlfriends and it was not that hard to manage.

As Christmas came around I bought Mary the same perfume that Susie wore so they would not get suspicious, I saw that in a movie.

I told Susie I had to work late you know making deliveries and we would go out the next night and do something special. I thought I should spend it with Mary as we had been going out longer.

We went out for a nice dinner and then took a drive up by the lake. Well one thing led to another and soon we had our clothes off and well you can figure out what happened.

It was so incredible and afterwards Mary told me she loved me and I said the same to her which I do love her well we got dressed and I took her home.

The next night I took Susie out and sense the night before went so well after dinner I took her up to the lake too. Well things went the same way and again clothes were on the floor of the car.

It was almost the same thing over. We made love and she told me how much she loved me and I felt the same and told her.

We sat there and talked and I found it hard to believe I was in love with two women. As we got dressed Susie suddenly got a strange almost mad look on her face.

She held up her hands and was holding up two pairs of pink panties. Hers ones and the pink ones Mary had on last night. She screamed at me what the hell are these mike, are you cheating on me?

You are the only girl I love. I was searching for words and as if out of nowhere I heard my voice say, they are mine.

Susie looked at me, yours? I just smiled and looked at her and she seemed calmer. Yes dear I know how it looks.

I felt really embarrassed but nodded my head yes. She thought for a moment, I thought you were cheating on me.

I said no I would never do that. She smiled; you better not because if you do you will not like what I do to you.

She gave me a little kiss, so do you like the look or the feel of the panties. Her question caught me off guard and unable to pick I said both.

She handed them to me and said, put them on for me so I can see. Unable to think I did as she said. She looked at me sitting there next to her in the hot pink panties.

You do look cute dear, promise me you will always wear them and she gave me a big kiss and slipped her tongue into my mouth. When we broke I smiled.

Sure you can nobody will see them under your pants; I will even buy you some new pretty ones. I smiled no they are mine and if you think I can get away with it I would love to wear them more and once again things were great.

I drove her home and kissed her good night. She smiled, come by my house in the morning before work I have a surprise for you and be sure to have your panties on.

She met me at the door and gave me a big kiss. She asked to see my panties so I pulled my pants down just far enough for her to see.

She smiled they look even better in the light. She then took out a tape measure and measured my waist.

I looked at her and she just smiled, I want to get you some pretty new panties and needed your size. She kissed me goodbye and said I better go before I was late.

Mary let me in and I asked her what she wanted to do today as it was Saturday. She smiled and said my parents are gone for the day as we sat on the couch.

We can do anything you like. We started to kiss and things got hot. I started to touch her breasts when she slid her hands down my pants.

I was feeling really good when she pulled her hand out and looked at me. I suddenly realized I had on the panties. Before I could say anything she asked me what you are wearing.

All I could think to say was shorts. She looked at me again can I see them? She let out a laugh and I turned red. She smiled I wondered where my panties went.

What made you put them on? I looked for what to say and all I could hear was Susie last night and said; I like the way they look and feel.

She smiled; do they remind you of me she asked? She smiled really big, how sweet Mike. You can keep them I will even give you a few more of mine so you can wear them all the time under your pants.

Mary took me by the hand and we went up to her bedroom. She went to her dresser and opened the drawer. She looked at me I have a couple panty sets that I just bought you can have if you like as she pulled out a bag.

I said thank you that would be great. She handed them to me and then said oh I guess you will need this to and handed me a pink bra.

I looked at her with a strange look. I looked at the two pairs she had given me and sure enough there was a black panty and bra and a white panty and bra.

I did as she said and she slipped the bra and fastened it behind my back. She took off her clothes and stood next to me in just her bra and panties.

The bra felt funny to wear but there was something about it that made me feel nice. We spent the day together and had a great time and when I left I was wearing the bra and panty under my clothes.

When I got home mom was just putting dinner on the table. I sat down and Jill, mom and I ate. Jill smiled or worse, if my boyfriend did that to me I would do everything I could to make him pay.

I know what you mean I said and they both just looked at me. When it was time to go to bed mom gave Jill a hug and a kiss then she turned to me and kissed me on the cheek and gave me a hug.

I felt her hand start to pull away and then she slid it down my back. I wondered if she had felt the bra.

Mom looked at me; Mike is there something you want to tell me. Jill was half way up the stairs when she heard mom and stopped to look.

I smiled no why I asked? Mom again said I was wondering what you were wearing under your shirt dear?

They both looked real close at my shirt as if they were trying to see through it when Jill reached over and touched my chest.

She let out a yell; it feels like a bra mom. I knew I was turning red as I stammered for what to say. Mom just smiled again, Mike please take off your shirt.

The look in her eyes told me a better do as she said so I slowly removed my shirt revealing the pink bra. Jill let out a laugh and mom just asked again, is there something you want to say?

We sat back down and I explained about what had happened with the panties and how they both thought it was cute and wanted me to wear them. And then how Mary said the bras went with the panties and wanted me to wear a bra too.

Jill smiled, how are you going to explain the bra to Susie she asked? I had not thought about that. Mom just smiled, I guess this is one of those things that pop up when you miss lead people.

You need to tell them the truth dear. Well dear then you are going to be wearing a bra and panty from now till you tell them.

Tell them the truth or wear this stuff. You mean but before I could finish she said, yes you will wear these all the time till you tell them.

Jill got a smile on her face but mom looked at her, Jill you will not say anything about this to anyone or tease your brother or I will find a punishment for you.

Jill just nodded. I went upstairs and went to bed. Susie let me in and said I have your present upstairs. I thought to myself I have one for you too as I felt the bra strap dig into my shoulder.

As we walked upstairs I thought how I could tell her. She looked at me and handed me a box wrapped up with a bow.

She smiled would you rather buy them, I can go with you. I smiled as she started to open my pants and saw the black panties.

Wow dear you have a new pair did you go shopping. I thought that it and smiled yes I stopped last night and bought them. She gave me a kiss, you have great taste in panties they look great on you all you would need is a matching bra.

I got a panic look on my face and looked down. She smiled do you want a bra too honey as she smiled. I just said nothing.

I quietly said yes and took off my shirt. She gave me a big hug; you look adorable sweetie I made the right choice.

I looked at her as she said open your box. As I opened it there inside were matching bra and panty sets. I thought to myself between the two of them I now had more then I could wear in a week.

Things went well for a couple weeks and I had gotten use to wearing the bra and panty every day. Her parents went away for the day and left us alone.

I asked her what she wanted to do. It sounded like a great idea so I said I would run home and get my swim suit.

She handed me a hot pink bikini and said this should fit you and she went into the other room to put her bikini.

When she came back she looked hot. She was also wearing a hot pink bikini. Sweetie, it is no different than your bra and panty. Please for me you will be so cute and nobody will see you in the back yard.

She kissed me full on the mouth so I went ahead and put it on. We spent the day swimming in the pool and lying in the sun. When it was time to go Susie helped me put my bra back on for some reason she liked helping me.

I kissed her good buy and went home. Mom asked me how my day went and I told her we had gone swimming. I told her no Susie let me borrow and I paused one of her suits.

Jill spoke up, was it a bikini I bet you would look great in one? I suddenly realized how stupid it sounded. I shook my head no. Mom told me to stand up and take off my shirt.

I did as they have both seen me in the bra. Mom reached up and pulled on the cup of the bra and let out a little gasp. I was puzzled as she asked me to remove my bra which I did and noticed them staring at me.

Mom had me look in the mirror; I was scared because I had the start of a really nice tan except where the bikini top was. Panic struck me as I thought how I can explain this to Mary.

Even without the bikini to get a tan like this would have taken hours out in the sun with just the bra on. That night I had a hard time sleeping as tomorrow I would see Mary.

We were home alone and Mary asked what I wanted to do. As I thought she spoke up, it will be hot today so we should stay inside unless you want to go swimming?

She gave me a kiss Mike I am sure I can find something for you to wear. I looked at her well I would have to see what you have first. She gave me a smile, you have been wearing panties and a bra for weeks and you are worried about my swimsuit, I will give you your choice.

She pulled out two bikinis, one red and the other pink and asked which I liked. The red one was almost the same as the one I wore yesterday so I took it and went into the bathroom and changed.

We spent the day outside. When we got back inside I looked down and smiled, I think I may have got a little too much sun as I took the top off.

Mary gave me a big hug, what lovely tan lines you have. I had pulled it off. A couple nights later I took Susie out for dinner and then back up to the lake.

We had not had sex sense that first night at Valentines and I was hoping we could recreate that night. I was right and things went great.

As I dropped Susie off at her home I went around to help her out and she dropped her purse and it spilled on the floor board of my car and the ground.

I helped her pick it up and walked her to her door. We had a very passionate kiss and I was on cloud nine as I got back into my car and drove home.

The next day I decided to try with Mary so I took her out to dinner and then suggested we take a ride up to the lake. Mary surprised me and said no.

I looked at her as she said her parents were gone for the night and we could go back to her house. As we drove home she kept looking at the floor.

When we got to her house she took her purse and picked something up off the floor board. I asked what it was and she just said nothing. When we got inside she put her keys back into her purse and then I saw her staring in it and then she looked at me.

Mike can you explain this as she held something up. I looked and said what is it? I thought it had fallen out of my purse but it is a supper size I use regular.

She walked over to me; did you take this from your mom she asked? Let me see what I can do for you. I wondered what she meant as we went upstairs.

We went into her bedroom and she told me to strip down to my bra and panties as she went into the bathroom. She came out wearing just this little pink night gown that you could see through.

I was excited as this would be our first time in a bed. I went over and she gave me a big kiss. She smiled turn around and bed over sweetie.

I did as she said and I felt her pull my panties down. She kissed my butt cheek and then said that supper size tampon is just too big for such a sweet little hole but I have a regular that will be just right.

I had no choice and said yes. She inserted the tampon in and then pushed it all the way in. There we are my sweetie how does that feel. I stood up and said it felt really strange we should take it out.

Sweetie she said it takes time to get use to this, just leave it in for a while and she kissed me. I think we should do this a few more time before you decide if you like it or not but we will wait a week till we do it again.

She was rubbing my grown and I was feeling good so I said yes. We got into bed and made love. It was so special and I even forgot about the tampon.

It was almost 10 when she said I had to go so I got dressed and went home. The next morning I got up and was feeling a little nauseous.

I sat on the edge of the bed and we talked as she did her makeup. For some reason I found it fascinating to watch her as she applied her makeup.

The next couple day when by and the sick feeling I had went away. At school I would watch the girls to see how they had done their makeup.

I got up Wednesday morning and as I was getting ready for school my chest looked different, almost like the skin the bra was holding was now staying up even without the bra.

I went back into my room and put my bra and panties on and then my pants but I noticed my pants were tight and I had a hard time getting them over my hips.

I thought to myself I must be putting on some weight. I put on a sweat shirt and left for school. When I got to her house she greeted me with a kiss, sweetie she said I have a surprise for you.

I looked at her and asked what? My parents are out for the night and she took my hand and led me upstairs.

On the way she asked me what was bothering me and I told her I was gaining weight. She went to her dresser and brought me a bottle of pills, just take one of these every afternoon before dinner and you will lose the weight.

I thanked her and went into the bathroom and took one of the pills. When I came back to her bedroom she was sitting on her bed wearing just her bra and panties.

I took my close off and walked over to her. She smiled my you look beautiful honey. I sat next to her and we started to kiss and then I got a little light headed.

She had me lie down on the bed. After about ten minutes I felt better and we started to kiss again.

She pulled down my panty and started to play with me but nothing happened. She smiled; sweaty it looks like you are not in the mood.

Soon she was moaning as I stood there and watched. I watched for about twenty minutes as she did herself and finally she let out a scream and collapsed on the bed.

After a few minutes she sat up and smiled, wow that was good. She gave me a big kiss and slid her tongue into my mouth. Do you want me to do you honey she said.

She told me to close my eyes as she had a big surprise for me. I did as she said and I could hear her doing something but she told me not to peek so I kept my eyes closed.

She came over to me and told me to open my eyes as she kissed me. I looked at her. She smiled we are going to play a game where I am the master and you are my slave and you will do what I say.

For some reason this excited me, not enough to help me get hard but still there was something about her telling me what to do.

Get down on your knees sweaty she said as she put her hand on my shoulder and pushed me down. She pushed it right in my face and told me to kiss it which I did.

I could taste her on it and I liked it so when she told me to suck on it I did. Soon she was pushing it in and out of my mouth and I was gagging.

After a while I stopped gagging and even enjoyed it. She finally stopped and said sweaty what a good girl you have been now turn around and bend over.

I did as she said and felt her pull my panties down. She stood behind me and put a cream on my butt hole and then put her hands on either side of my hips.

As I wondered what she was doing I felt her push the long object against my butt. The pressure mounted and then I felt it slid in. As she drew it back out slowly it felt better but then in it went again.

She pushed in and out and the speed and force increased till soon she was pounding away on my poor little hole. This went on for about fifteen minutes and then she pulled all the way out and I collapsed on the bed my heart was pounding.

She came over and laid down beside me and kissed me, I loved that she said. Then she smiled, you did enjoy it as much as I did she asked. She kissed me again and smiled, we will have to do it again.

After I got dressed I saw her in the bathroom standing in front of the mirror, she was doing her makeup. I walked in sand started talking the whole time watching her as she did her face.

Yes I said again. She smiled and it feels so nice, would you like to see how it feels sweaty? And without thinking I said yes.

She smiled and gave me a wink. Okay dear but just a little. I stood there as she gently took her brush and put a powder in it. She tapped it off and then started to brush it all over my face.

After a few moments she smiled what a wonderful glow you have. Next she had me shut my eyes and she put the lightest of eye shadow on my lids, this is peach dear it will brighten your eyes.

Then she took out a lipstick and put some on. There we are sweaty a beautiful natural look. I looked in the mirror and Susie said you like it right.

I nodded and said yes. She smiled and gave me the makeup powder, eye shadow and lipstick. You can have this that way you can wear it every day you want to wear it right.

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