My Road To Cross-dressing (part 2) free porn video

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I had dressed up since I was a teenager but it was only occasionally. Usually, it was just lingerie and it was always for me and just for masturbation. It was about ten years ago that I decided I wanted to go further and start using makeup and breast forms and wigs etcetera.

Quite by chance one day, I rang an old friend just for a chat. I found out that he had rented his house out while he was travelling. The person on the other end of the line was a woman, or so I thought. We got talking and I discovered that it was another old friend who had gone through a full sex change. I had no idea at all that he had done this as it had been kept private. 

She had renamed herself, Sarah. She asked me if I would still talk to her now that I knew. I said yes, of course I would and that I didn't have a problem with it. Secretly I had another motive.

I remember thinking about it incessantly over the next few days. The secret, lonely life I had was fun but was still frustrating. Here was someone who had had the same issues and desires. By far the biggest fear I had at that time was that someone might find out, disapprove and tell everyone.

I did feel shame because of the way society viewed cross-dressers and transvestites. There were also many ramifications with this being common knowledge, my business, my children, and violent bigots etcetera. If only it was possible to talk openly about such a lifestyle. I didn't want a sex change but love dressing up.

I realised that this was the first time I had actually talked with a trans person and was desperate to tell her my secret and the frustration I was experiencing. Inside I had this burning desire to tell someone about it. This seemed to be my chance knowing that she would understand. 

I nervously approached the subject and asked if she had started with cross-dressing. She had. The conversation went on for a little while and I was trying to act as if I was just curious. Sarah told me that I was very accepting and it was refreshing to find someone who didn’t judge or rebuke her for being what she wanted to be. This was the moment when I knew that I could tell her, but still, I resisted. She was obviously aware that something was a bit untoward but refrained from commenting. 

As I went on I approached the fact that it must be difficult to admit that one was a crossdresser and to tell anyone. Sarah assured me that if such a revelation was going to be admitted, it was far better to talk to someone who had gone through the same experiences. Bang! this was my chance.

For a few seconds, I stayed silent as my mind panicked. All sorts of emotions percolated every cell in my head, ‘tell her, admit it, own up, say you crossdress and have done so for years and you love it, and try not to get too emotional and cry, but do it, do it do it!’

Well, I did. 

“Sarah. I am a crossdresser. I have done it for years and no one knows. It’s been my lonely secret. Can we talk about it?”

Sarah was wonderful and very understanding. She told me that she did suspect as the conversation was very revealing. She knew how hard it was to come out and say it. 

“Be proud that not only do you dress but that you have admitted it to me,” Sarah said supportively. “It’s ok, really it is. You are not alone. There are many people who do the same.” 

She told me that I had to pick a girly name for myself as that was what ‘we’ do. I started thinking about it and then decided that I liked the name ‘Lucy Lou.’ We also talked about certain aspects of the whole cross-dressing thing. How and when I started, what I wore, and was there ever any sexual element to it. It was uplifting and I felt so relieved. We decided that we would talk in a day or so after I had got my head around the fact that I was no longer alone. 

I put the phone down and sat there dazed for about five minutes. I actually felt really turned on that my dressing had gone up a stage. I immediately went to my bedroom and opened my case with my clothes in it and started to dress. All I had at that time was a wet look basque, a pair of panties and fishnet stockings but it still felt invigorating. 

Sarah told me that there were websites for cross-dressers and trans people and I should go to one of them and create an account. The first one I went to was a site called Tvchix.com. I logged on and started the process. I didn't stay on the site for very long as it turned out to be just about sex and masturbating, which wasn’t really what I needed at that time. 

I was determined and started searching the net for something that was more serious and where I could talk about my issues. I found a site called crossdressers.com and enrolled. It was much better and was a  revelation when I realised that I was not suffering alone and that there were thousands of guys/girls just like me. It wasn’t about sex or dating but a place where there were forums where sensible, intelligent discussions took place. This was really what I so desperately desired.  

It helped a great deal because I sorted out some important points, almost immediately. The most important point was that of something called purging, i.e. throwing all my clothes out and saying to myself that I was wrong to be doing this and that I would never go back. But after a few months, I would feel the desire and need to dress again. So would start again, feeling so sad that I had lost so many lovely things. 

I found out that this was also a normal thing for crossdressers. Every time I had purged I regretted it. Some very kind and understanding girls helped me deal with it and told me that if that was my mindset that I should just put everything in a case and stick it in the loft or garage or somewhere out of site. When the desire came back I could just pick up where I left off, without having to go back out and buy a load of new stuff.

They also made me realise that this was a part of me that was never going to go away so I should just accept it, embrace it and most of all enjoy it. I did feel somewhat liberated. 

Two days later I called Sarah back and told her all about my findings. She was very encouraging and we discussed what else I needed to get. I had no picture on the site but it would be much better if I did. 

The journey began with new vigour and the desire to get myself looking feminine was paramount. I found places online where I could get some wigs and dresses. I had already found a place to buy lingerie but needed so much more if I was going to do it properly.

Shoes were a problem because I wanted stiletto heels but no shops would stock them in my size. I did find a place in Spain that had all styles of heels and women’s shoes in all sizes, even mine. Every time I ordered something I felt excited and couldn’t wait for them to arrive. It was an exciting time. I also found a place to get breast forms and decided that 38D would be right for me.

Then there was the whole issue of makeup. What would I need? Foundation, blusher, powder, eyeshadow, mascara, eye pencil, lipstick, and perfume, (which would only be for me as no picture could be smelt.) Then I had to get some jewellery. Earrings, necklaces, rings and bangles. 

As this process continued I realised that it was quite expensive making myself look like a woman. Really expensive. Hundreds and hundreds of Euros but I was committed and just made it happen. 

The other aspect was that I had to learn how to put my makeup on and the more I did it the better it got. I took pictures of myself and practised. I accepted the fact that I needed to improve but found a look that I liked and posted some pictures on my profile page, found an avatar face picture and then suddenly it dawned on me that I had done it.

There were some very lovely complimentary comments made by other dressers and this made me feel good about myself. I could be a cross-dresser and show pictures of myself, talk to likeminded girls and just embrace the whole experience. 

This whole wonderful experience also made my self-stimulation so much more for filling. Being dressed turned me on and seeing myself dressed like a woman has made it better than I could have imagined it would. 

I have had such a ball and love being Lucy Lou. 

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I would assume that for most men, interest in women’s clothing started at a young age. For me, this occurred when I was 11 looking through the Littlewoods, Gratton and Freeman catalogues that my mother used to have.At the time, I lived with my mother Jane, who was divorced, my brother Anthony and sister Sharon, who were five and three years older than me. It was quite easy to sneak one of the catalogues up to my room and thumb through them. If one of them had bothered to look at the catalogue,...

1 year ago
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Cross Dressing for Ann Again

About a week after my first amazing session with Ann, the neighbour from downstairs who blackmailed me into modelling her lingerie, I was again accosted by her on the stairs.“Hi,” she said, coming out of her front door as I was passing. “I’m glad I bumped into you” (I knew she was lying in wait behind the door watching out through the spyhole) “are you doing anything on Wednesday night?”I said I wasn’t and she said that as John and Ian (her husband and son) were going to Aberdeen to watch the...

2 years ago
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my first cross dressing play time

i sucked my first cock the other day. i posted a ad on craigs saying i like to cross dress and would like to find somebody to dress up with and take turns being sluts to each other and then i posted a few pics of me from my xhamster profile and actually got alot of replies. it took a few weeks but i finaly found somebody that like to dress up and he came over during the day and we started watching porn and i pulled out all my slut clothes and we picked out things that we wanted the other person...

4 years ago
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Cross dressing gay fantasy

I would wear black stockings and no other clothes. My whole body would be shaved. I put on cream that makes my skin look even whiter and blemish free. I want my skin to look as feminine as possible. I would wear a jet black wig like a messy bob. One were I can pull the hair over to partially cover my face. I would wear oversized black sunglasses with dark red lip stick and maybe some temporary acrylic nails. I sit on top of the kitchen work top with my knees up at my chest and feet crossed...

4 years ago
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All day crossdressing twosome

This experience was a twosome with my closest tranny friend.We got together one Sunday morning and transformed ourselves fully into hot sexy sluts. We were both wearing well stuffed bras, suspender belts, crotchless panties, stockings and high heels.We lay on the bed together kissing and stoking each other. We had made sure we had full balls for each other, so we were very horny.I got a pair of handcuffs and we closed them tight around our genitals, joining us closely. The twist was that the...

1 year ago
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Bi MMF FemDom Cross Dressing Cuck Part 3 Oh M

All dressed up super sexy, I was setting out for my erotic date with my new lovers, former friends. I felt so desirable and sexy as I drove to my erotic destination. I couldn't help but have a boner the whole time I was driving. I kept feeling myself while I drove. Feeling my exposed thighs, my smooth legs, my silicone tits, my sexy cock.... I was insanely turned on. I also kept looking down at my fuck me pumps. I'm addicted to heels more than anything else so just the sight of my sexy...

3 years ago
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First Cross Dressing Experience

Let me start the story and sorry if I make any mistake because I am excited to share my fun time with you people so I am an engineering student from Mumbai 20 years old. My name is raj (name changed) and used to have a big fantasy of dressing like a girl and wearing all those ladies cloths. I would like to make it clear that I am not a gay but when I dress like a girl. I feel like a girl and make me comfortable with a guy; at that time I get a girlish feeling which makes me horny and takes me...

3 years ago
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Cross dressing first time out

Now I had been seeing mike for a few months now and the relationship was going well. He had introduced me to paul he work friend for a three some which was amazing and the dressing up was getting more and more kinky!!! He hadn't never pushed the boundaries with me kept it simple and sweet, until now!! I always did as as he asked to a point, never anything abusive or nasty he knew what I was into. So when he asked me to dress up and go to a night club i was shaken and a bit scared!! I had never...

3 years ago
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First Time Cross Dressing

Lisa Smith was always a bit spoiled. She was a sexy and teasing little minx. She was 22 years old with a smoking hot body. She loved to tease and be treated like a princess. She acted all sweet and pretty but she had a wild side. She loved to control men. She loved to make her buy her stuff. She loved to cock tease. She made a lot of money on it. She loved the power and intimidating them. She prided on getting a man to anything just by using seduction. One thing she wanted to do but never got a...

Fetish
1 year ago
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My Crossdressing Urge

Having previously enjoyed my lustful dalliance with my first cross-dresser, the thought of him clad in beautiful lingerie was an image in my mind that I could not shake for weeks. I had discovered my liking for women's underwear in my teens when I used to visit my grandmother, and she always had beautiful stockings in her hosiery drawer. I would slip them on when I would stop overnight, delighting in their feel, the smell of the smooth nylon as it encased my teenage legs. Sometimes, I would...

4 years ago
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Wife indulges her husband8217s crossdressing fetish

When my wife Jane asked if I would be a volunteer worker at her company’s western night, I said sure, why not? She told me she would fill me in on the details as the time drew nearer. A couple of weeks before the event, Jane started making a satin saloon girl outfit. I teased her and told her to be sure to make it extra frilly and sexy, and she said I could be sure of it. It wasn’t until two days before the party that I got the rest of the story. When our costumes were ready, my...

3 years ago
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cross dressing fantasy i didnt know that i had

went on a stag holiday to ibiza with about 20 of my mates a couple of years ago.the holiday mostly consisted d**g taking copius amounts of drink and sl**ping with llots of women. the main stag night was fancy dress,and id already planned before i came away id already decided that i was gonna wear i toga and my girlfriends flat gladiator sandals and go as troy.a few of us got quite pally with the girls in the appartment opposite and the daytime before the main nite out one of them commented that...

3 years ago
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cross dressing fantasy i didnt know that i had

went on a stag holiday to ibiza with about 20 of my mates a couple of years ago.the holiday mostly consisted d**g taking copius amounts of drink and sleeping with llots of women. the main stag night was fancy dress,and id already planned before i came away id already decided that i was gonna wear i toga and my girlfriends flat gladiator sandals and go as troy.a few of us got quite pally with the girls in the appartment opposite and the daytime before the main nite out one of them commented that...

4 years ago
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Xena Versus The Spartans

It was a time of horrible raids by terrible marrauding hordes, which caused untold misery, fear and poverty in all of Pelopones. It was a time when Xena and Gabrielle were needed by all the towns, before it is too late, but she was nowhere to be found. The century before had been a good time for all, under the Cooperation Accord of Olympia, there was piece between all the polises, and Xena could concentrate on petty crime and feuding Gods. But now Xena had been on a mission in Asia for years,...

1 year ago
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Cross dressing

Hello is my story. This happened. It was the mid 80’s and I just turned 17 so I thought I would go to the mall near my home town on Long Island and go shopping with my birthday money. I was looking for clothes with and I need to use the rest room. I walked into the bathroom, and the floors were wet so when I made a turn, I slipped. I put my hand against the door of a stall that was closed as not to fall, and the door it flung open because it was not locked properly. I looked inside and a man...

3 years ago
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The Cross She Bore

Memories are sometimes not to be trusted. In looking back on the past, what one believes to be a memory is in actuality what one prefers to think the past was like. We do this unintentionally -- whether as a defensive mechanism or the result of the layering of visions of the past, one on top of another, until the distant past is obscured. For Rebecca her fascination with the cross and with the practice of crucifixion seemed in retrospect to have been acquired at an early age. Now as a single...

2 years ago
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Road Trip Jim Mellons Erotic Journey Across AmericaChapter 26 Montana

After seeing Yellowstone National Park, I knew that I wanted to come back in warmer weather. A few of the side roads through the park that looked interesting were closed to traffic. I headed for Livingston, Montana for an overnight stop before getting on Interstate 90 and heading west to Coeur d'Alene where I had an ex-Army friend. The day had started sunny, and according to the forecast, clouds would roll into the region before a small front swooped through with a chance of light snow...

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