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Cross-Dresser Loves being used

"How I became hooked on cross dressing"

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Author's Notes

"I just love to cross dress and play"

I have cross dressed for almost fifty years. It started in the UK when I was eighteen, I had often read the various catalogs for mail order purchases and used to look at the women's lingerie pages where the ladies were wearing garter belts, girdles, panties, stockings etc., and I used to get hard and play with myself and jack off to the pictures.

I was always fascinated at my older sister who used to wear stockings, garter belt, etc. and it excited me. One day when nobody was home, I went to my sister’s bedroom and looked in her drawers and found a black garter belt, a pair of black stockings and black silky lace panties. I was feeling very horny and decided to put them on. First the garter belt, then the black nylon stockings and then the panties.

My cock was rock hard by the time I had everything on and I stroked my cock through the panties and ran my hands up and down the silky-smooth black nylons on my legs and it felt incredible. I liked it so much that I jacked myself off in her lingerie. It was such a great feeling that I couldn't wait to do it again.

It became a regular thing and I would long for my parents and my sister to be out of the house so I could dress in her stockings, garter belt and panties etc. I very quickly became hooked on this and loved the sexy feeling of her lingerie on my body, it felt so sexy and I would get so turned on that when I jacked off I would shoot really big loads of cum each time.

Later my sister got married and moved of our house and I didn't have access to her lingerie any more. So I started to go to some of the second hand clothing stores and they had some called Oxfam and Salvation Army just like the Goodwill etc. here in America. These stores would have women's clothing as well as lingerie like garter belts, bras, panties and sometimes if I was lucky even stockings too. By this time in my life I was looking to get an apartment of my own and did six months after my sister moved out .

Once in my own place I could do whatever I wanted and would often go on a search mission to the second hand stores to buy myself some lingerie. I was able to find some quite nice lingerie, my favorite color was black and I quickly found a few black four strap and six strap silky and lace garter belts, some matching black panties and bras as well as several pairs of black nylon stockings as well as a few black nylon or satin knee length slips.

I took them all back to my apartment and washed everything and the next day started to dress up in them. I was so excited and the thrill I got from wearing them was incredible. I would come home from work every day and take a shower and get dressed up in my own lingerie and jack off.

As time went by, I was so much into the cross dressing that I wanted to see if I could go out wearing my lingerie under my regular clothes. I did get up the courage one evening and put on my black six strap garter belt, black panties, black stockings, black bra and slip and then put on my jeans and a lightweight jacket and shoes. I went and walked in a park close to where I lived. It was dark and there was also a public restroom in the park which I saw several men hanging around the outside. I did not know at that time they were just horny and, in some cases, older men looking to play with another person.

I needed to pee, so I went inside the men's restroom and there was a long trough as a urinal with several guys standing at it, and three stalls. Two of the stalls were occupied and the one in the middle was empty so I went in the middle stall and locked the door, I opened my jeans and got my cock out and had a pee. As I was doing so, I noticed the walls on both sides of my stall had very large holes in them and even in the dim lighting in there I could see someone on the other side looking through the hole.

One of the guys spoke to me and said can I see you cock; I was shocked at first then the guy on the other side said come on show us your cock. I was feeling a bit horny by now and did not know what to do. The first guy who asked to see my cock put his hand through the hole and reached for my cock, I backed up against the other side wall and then I felt two hands come through the hole and reach around me and touch my cock which was rock hard by now due to me wearing my lingerie.

The guy in the other stall saw this and put both his hands and arms through the hole and was also touching my cock too. Then he said drop your jeans and let us see more of you. I said no I don't want to, but the guy behind me held me by my hands against the wall to his side as the guy on the other side in front of me undid my belt, unzipped my jeans and pulled them down. He let out a gasp and pulled me forward and told the other guy through the hole what I was wearing.

They said you are very sexy dressed in the lingerie and have made us get very hard. They asked if they could put their cocks through the and if I would jack them off? I told them I was afraid and had never done anything like that before. They said I was dressed so sexy and had made them so hard and horny they needed to get off. I thought what harm can it do so I agreed and they told me to first take my jeans off and let them feel my stocking clad legs up to get them even more horny.

I took my jeans off and hung them up on the door and stood in the middle between the two walls and they both put their hands through the holes and was feeling up and down my stockinged legs and that made me feel very excited and horny. Then one guy stood up and put his cock through the hole, I gasped when I saw how big it was, he had least seven inches sticking through the three inch thick wall and it was very thick, I could not get my hand around it.

I said wow, that is the biggest cock I have ever seen. He asked me to stroke it and I reached and touched it and started to stroke it back and forth. The other guy stood up and put his cock through the hole on the other side and it was least an inch longer and even thicker than the first guys cock. He told me to stroke his cock too and I did as I was told. The guys were loving it and moaning as I stroked their cocks.

Both guys pulled their cocks back through the holes and one guy told me to kneel down with my head close to the hole on his side. I knelt down and he said you stroke cock really good, but with you dressed so sexy and slutty, he asked if I had ever sucked a cock before. I said no I have never stroked a cock before until tonight, and never sucked one either. He asked if I would like to try it, I said I was afraid and he said, "It’s okay, just take it slowly and see if you like it and if you don’t, we can just stop."

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I was standing there in black stockings, garter belt, panties, bra and a slip and feeling very very excited. I said yes I will try it, so he stood up and put his very big thick cock back through the hole and I took it in my hands and licked the end, he said open your mouth wide and slide your lips and mouth over and down my cock. I did as he told and his cock was so thick it almost split the corners of my mouth.

I built up some saliva and rolled it around my mouth and lips and it helped to let more of his massive cock slide deeper inside my mouth. I must say it felt very nice and sexy and I started to slide my mouth back and forth on his gorgeous cock. After about 5 minutes he pulled out and back though the hole and asked if he could cum in my mouth. I said I have never done that and was afraid. He said don’t be frightened you will like it after I have cum in your mouth. He told me that his wife had not let him have sex for about six months and she would never suck his cock, he also told me that I was sucking him so good that he really needed to cum.

I said I would try it and he put his cock back through the hole and I started to suck it again, he put his hands through the hole and held my head on either side as he slid his cock in and of my mouth. He started to go faster and deeper with each thrust and started to moan and groan, then he said he was going to cum and he pulled my head towards the wall and held it there so his cock was all the way in my mouth and his cock head was at the entrance to my throat.

Then I felt his cock shaft pulsating and throbbing and his cock shaft and cock head grew harder and thicker as he started to shoot his cum in my mouth, his first three wads of went straight down my throat and he pulled back a bit and shot at least seven to eight more big wads of thick creamy in my mouth. He shot so much I could hardly contain it in my mouth, but he held my head there and said just swallow it all down like a good slut.

I had no choice other than to swallow all of his cum and then he let go of my head and pulled his cock back through the hole and said, "Thanks very much I definitely want to meet you again."

The guy on the other side asked if I would suck him off too and I said I don't think I can take another load like that on my first night. He said he understood, but asked if he could jack his cock off and shoot his cum all over my black stockings. I said that would be okay, so he asked if we could go outside behind the building so he could do it and make sure he shot and splattered his cum all over my black stockings. I asked him if it is safe to do that, he said, "Yes, its very safe everyone here knows what goes on around here and nobody will interfere or disturb us unless you say it’s okay."

So, I pulled my jeans on and we went out with him to the back of the building, it was quite dark except for a dim light on the corner of the wall which gave enough light for anyone to see what I was wearing when I take of my jeans and jacket. There were several other guys hanging around the front and sides of the building and they looked as we walked past them to the back. Once we got to the back area there it was a little secluded with walls and bushes all around.

There was a wall about three feet high where we stopped and he told to take my jeans and jacket off. I nervously did as he told and was standing there just wearing my black six strap garter belt, black nylon stockings, black lacy panties and a body slip knee length. He pulled up my slip and tucked it into the top of my panties and told to sit on the wall so he could feel me up and down my stockinged legs.

He stood up again and told me to lean over the wall so he could feel me up over my legs and pantie covered ass cheeks. I was nervous but did as he asked and his hands were were roaming all over me, he took his cock which was rock hard and was rubbing it all over my stockinged legs and panties, he slid it between my legs at the tops of my stockings and close to my panties, like he was humping me. He was leaking some pre-cum and I felt it was getting quite wet, this was like a lubricant so it made his cock slide nicely between my stocking clad thighs.

Then he asked me to stand up and he wanted to put his cock inside my panties and slide it back and forth and then shoot his load inside the crotch of my black panties. I was so excited by this time I agreed to let him do that to me. He pulled the front of my panties down and slid his hard- cock between my thighs, and he told to squeeze my thighs together as he slides his cock in and out. I did as I was told and I could feel his pre-cum making his cock and my panties and between my legs very wet, and slippery so his cock would slide back and forth.

Then he went faster and faster, moaned and groaned and told he was going to cum. He pushed in a few more times and then I felt a spasm of his cock and a big splattering of his shooting cum between my legs inside my panties, he shot so much cum that I felt it oozing out of my panties and running down my black stockinged legs. It felt very warm and slimy and slippery but I liked it very much.

I noticed several more guys had joined in to watch what was going on and they all had their cocks out and were stroking them and saying great show, but they wished they also shoot their cum all over my black stockings too. The guy who had just shot his cum in my panties asked if I was willing to let these guys jack off and shoot their cum all over my black stockings. I said yes but that is all they can do. So, seven guys took turns to stand in front of me as I sat on the wall and they all jacked off and shot massive loads of thick white cum all over my black nylons.

This was my first time and I was so turned on by it that I knew it would happen again.

To be continued...

Published 
Written by stockingsluva1
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