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My Own Story

"A story about how I started crossdressing with a bit of a fantasy encounter"

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I have been into pantyhose for as long as I remember. I am not sure why I love them so much, but I can't seem to get enough, especially how beautiful women's legs look when they are wearing them.

When I was sixteen I remember playing around my mothers nylon covered legs when she came home from work. She would always wear very sheer hose and had wonderful legs.

During the summers when she and my father would be working I would try on her knee highs and would love the way they felt and looked. As I got more and more daring I would try on her worn pantyhose that were in the laundry and would even venture into the special drawer and try on her special, very sheer hose, they were very delicate and shiny. I could only do this for short period, because I had an older sister who was in the house usually at the same time. As I got more and more excited, I progressed to trying on her shoes (usually heels) with her pantyhose.

I used to wear the "Candies" slip on heels that were in style at the time, but would also put on her fancy high heels as well. One day when I had some time totally alone, I went the whole way and put on one of her dresses, a red matching two piece that had a nice short skirt and added a pair of black heels that matched well. I was hooked and loved the way I looked and felt and I would just prance around and try to look pretty and feminine. I did not have much hair on my legs and was not athletic so my legs looked very girly and I spent much of the time stroking and touching them. I continued these "sessions" for the next year and really loved being pretty and girly. When no one was home I would pick out the most feminine clothes to wear and pretend I was a pretty lady. This usually ended with me masturbating three or four times a night.

I will never forget when I had my first encounter. My parents were out of town and my older sister had a steady boyfriend, so she was not at home much at all.  I had practically the whole house to myself for the weekend. I took a nice bath with bath salts added to make my skin smooth and silky. I did not have much leg hair but decided to shave anyways to make sure I was smooth and it made me feel more feminine. When I finished I decided to paint my toes nails. I had never done this before but I loved the way it made girls feet look so pretty and wanted to do the same to my girly feet. I painted my toes nails a nice pink color and then put on a top coat of clear polish and let them dry. I then began to put on makeup, remembering how my mom would do it when I would watch her getting dressed. This took lots of time since I messed up often, but after an hour or so I thought I looked pretty good.

Next, I picked out a beautiful off-white dress that was cut about four inches above the knee. It was made of very soft silky fabric and was sleeveless with wide straps that came over the shoulders. It had a tight bodice that then flared out from the waist. The hem had a little curl to it which gave the dress a very pretty & feminine look. Next came some off-white pantyhose that were very sheer, almost translucent, and very shiny. I was amazed at how the hose felt with my freshly shaven legs, very tingily and my legs looked really smooth and pretty. I just loved putting them on and would take a long time gathering them up and gliding them up my legs.

I didn't wear panties either so I could get the full effect of the nylons rubbing on my legs and body. I also put on a sexy off-white bra and stuffed it with some more hose, added a short silky slip and got ready for the dress. Unzipping the back of the dress I slipped my stocking covered legs into the dress and pulled it up. My arms glided through and I pulled the dress up over my shoulders. I drew the zipper up and felt the soft material engulf me in femininity. The skirt played over my hose as I swished around and around. I felt so feminine in the dress and dreamed of being able to do this everyday.

I found my favorite pair of heels my mom owned and slipped them on very sexily. They were off-white sandals with a thin four-inch heel and thin straps around the ankle and toes. My painted toes which were visible with the sandals added a cute sexy look that I really loved. My hair was not totally feminine, but since it was the 70's it was long, almost shoulder length, so I styled it using a curling iron, to match the styles I had seen in the Vogue magazines my mother had. With my hair finished, I got some of my moms lipstick, a soft pink color and carefully painted my lips. Looking in the mirror I saw a very pretty girl looking out, I loved it and wished I could be like this all the time.

After prancing around the house and admiring myself in the mirror I built up the courage to go outside and feel the cool air and wind caress me. Not having done this before I took till 9pm to get up the nerve to finally venture out. I slipped out the back door and walked around the neighborhood. It was the greatest thrill, and I felt so pretty dancing along as a girl. My skirt was bouncing over my pretty nylons and I was feeling very sexy.

Not paying too much attention to my surrounding, I almost panicked when I saw a couple walking toward me. I thought about running but my heels and outfit would have prevented me from running very far, and they were too close. I decided to act natural and just walk on by. As they got closer I looked up and realized that I knew the couple from school. I was terrified and tried to slip by quickly, but the look in their eyes told me the knew who I was. I was dead. It would be all over school and I would be ruined.

The guy, Jere, said "Chris is that you, why are you dressed like that?" I was speechless and mortified.

Then Sheri spoke up. "Jere, he looks as good as you do when you dress like a girl."

He got the same panicked look that I know I just had and he snapped at Sheri, "Why did you tell him that?"

Then she whispered in his ear and they both smiled. Sheri then asked if I wanted to go back to my house and show them where I would get dressed. I agreed, because I had no choice.

When we got back Jere quickly stripped and began looking thru my mothers wardrobe and picked out outfits for both him and Sheri. Sheri helped get Jere ready starting with nylons and a bra. I sat with my legs crossed and watched Jere's actions, especially him putting the hose on, it looked very sexy and I noticed he was growing in excitement. He had smooth shaved legs and the sheer black hose made his legs look even sexier.

Next came the dress it was a mini black slip dress that gave him a very feminine figure and showed off his lovely legs. I was amazed (and pleased) at the quick transformation. Sheri started the makeup and then did his hair which was in a pony tail. She removed the pony tail and styled his long hair into a feminine form which completed his change into a pretty girl. Jere made a very cute girl, with his long blond hair, green eyes and makeup he looked very girlish. He slipped into some strappy high heeled sandals that made his legs even sexier and he was done.

Then Sheri started getting herself dressed. I had not seen a girl my age up close before and was transfixed at how soft and pretty she was. She put on nylons in a manner that I only dreamed I could, confident and aware of their beauty, but not nervous or shy about the femininess of the material. Her breasts were small but shapely and the sheer bra she was wearing made them even prettier, I was envious of them instantly. Sheri put on a pretty maroon silky dress that had a flared skirt and showed off her beautifully feminine legs which were encased in off-white hose and then some pretty black heels that had a very hot ankle strap.

She helped fix my makeup as well and we all looked like a group of girlfriends. It was lots of fun seeing them get dressed especially watching a girl get dressed. Sheri made a big fuss over making us look natural and even complemented me on my appearance, I naturally blushed and curtsied when she said this.

We all went and sat on the couch and Sheri told us to cross our legs and look like ladies, I was having the time of my life. Sheri then suggested we play spin the bottle, I agreed but asked what were the rules. She said she would right down a list of "tasks" that we would have to do and the person selected by the bottle would have to perform the task to the spinner. I was very nervous at the thought of this but my excitement caused me to agree.

She put all the tasks onto little pieces of paper and put them in a hat. She went first, she spun the bottle and it landed on Jere, she picked a task, KISS. Jere gave her a kiss. It was very nice to see two pretty girls dressed as they were kissing, but I knew this could be trouble and was excited.

I spun next and the bottle pointed to Sheri then selected a task, FRENCH KISS. Sheri jumped up and came over to me and gently kissed me gliding her tongue between my painted lips. I responded and was lost in the feeling of our lips and tongues intertwined.

As we kissed Sheri ran her hand up my leg and was caressing my nylons. I loved this feeling, especially from a girl, as I have never had anyone touch me while I was dressed as I was.

Jere spun next and the bottle pointed to me. He selected a task, BLOWJOB. It had been a fantasy of mine to do this but I never thought it would happen. Sheri squealed, as she was hoping she could see this. Jere was a bit nervous himself, but said we all agreed to play by the rules. I have never been with a guy prior to this moment, but I have fantasized about performing this task on countless occasions. I didn't know if I could do this to a guy, but Jere didn't look like a guy at all, he was very feminine and pretty with smooth sexy legs and was wearing a gorgeous little black dress. I knew this was an opportunity of a lifetime and the erection growing in my nylons dictated what my choice would be.

As we were sitting on the floor, Jeri got up went to the couch, then smoothed his skirt as he sat down, just like a girl. It was apparent he had spent much time dressed. I mirrored his actions and sat next to him while crossing my legs allowing my skirt to move higher and exposing more of my nylons.

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I reached out and touched his nylon covered leg which immediately twitched with excitement. Sheri was sitting on the floor in front of us captivated by the site. I caressed his legs all over feeling the softness and smoothness of the hose. I continued and then let my leg cross over his while I turned to face him. I was so turned on by his feminine appearance and felt that I was operating without thinking.

Sheri got up and sat on a chair across from us, and put her hand down her hose and was moaning and panting at the site in front of her. I straddled Jere on the couch and sat on his knees and then looking him in the eyes moved forward and kissed him softly. He responded and our lipstick covered lips touched as our tongues danced. Sheri was squirming on the chair and groaned encouragement to us to continue and fulfill the task.

Slipping off his knees I knelt in front of him and kissed the top of each knee. I spread his knees apart and ran my hands up his inner thighs until I reached his cock. Without my knowing it he had cut a hole in the front of the hose, but his cock remained inside hard and swollen.

I reached out and began rubbing him through the sheer material, he was beginning to get really excited and pre-cum was forming at the tip. I continued stroking his growing tool and then reached thru the hole and pulled out his now hardened six-Inch member. It was similar in size to mine and very smooth and shiny, more pre-cum was already oozing from the tip as I stroked it up and down several times.

Sheri realized that I had never done this before and instructed me to gently grab it with my hand and kiss the tip and slowly lick before I began to suck it. I bent over and had my lips inches from the head when a flash of panic hit me.

My mind raced through thoughts, I was about give a blowjob, I was a guy, this was one of my fantasy not to be realized, I was dressed as a girl, I felt like a girl, I loved how I felt, I wanted to suck him, what would my parents say. With an excited pant I pushed these thoughts aside (except the girly feelings) and gently kissed and licked the head.

I could taste the sweet pre-cum and licked it off the tip with my tongue. I was loving the taste and smell of the clear fluid and cleaned off all that had formed at the tip of his cock. I pumped him gently with my hand and brought forth more pre-cum which I quickly licked and swallowed (I loved doing this).

Sheri came down right next to me now and instructed me to run my lips and tongue up and down the sides, which I eagerly did. I never felt so girlish and was getting very excited. I could feel myself falling into a feminine state and I sensed the nylons, heels, dress, and makeup I was wearing pulling me into that state more and more. Jere was looking down at me and I could feel was as excited as I was, his breath shortened and member hardened even more. I felt the control I had over him at that moment and began to understand the power of women, the power I was starting to have as a pretty girl.

With his cock well lubricated I gave the head a nice kiss, leaving a very pretty lipstick mark. I then took a deep breath, parted my lips, and took him lovingly into my mouth, pausing at the head and then bringing it as far in as I could without choking.

Jere moaned with pleasure as did Sheri who was inches away and transfixed with my performance. It felt perfect and wonderfully satisfying, it was so soft and warm, yet firm and hard underneath. I slowly worked my head up and down rythmically savoring all the tastes and smells.

Jere was in heaven, he kept moving and bucking as I took him in time after time. As I was sucking him, I would caress his nylon encased legs which I knew was driving him crazy. I was in complete control of Jere and felt very feminine knowing that he would do anything for me as long as I continued to give him a blow job.

I asked Jere to standup, and had him stand in front of me while I sat on the couch. I ran my hands up and down his girly legs and finally reached the skirt of his dress and pulled it up to give me access to continue working on his beautiful cock. In this position I could look at his pretty face as I serviced him.

I was really getting into giving him a blow job, and was getting better at taking it deep within my throat. Little by little I could take it in more and more until I hit the base with his balls slapping gently on my chin. Jere would go crazy every time I took him in deeply and I encouraged him by moaning and looking up into his eyes as I took him deep.

He wasn't going to last much longer and I had a decision to make about whether I wanted to take his cum in my mouth and complete my fantasy. As I was pondering the choice I felt someone tear a hole into the crotch of my nylons and pull out my rigid tool. Sheri was on her knees beside me on the couch and began to go down on me like she was extremely horny.

This was too much for me, my total fantasy was being fulfilled at this moment. I lost track of my senses and was just enjoying all the amazing feelings and sites I was experiencing. Sheri was loving my cock with her beautiful lips and was rubbing the inner part of my smooth thighs. This caused me to really let loose on Jere's cock as I deep throated him more and more.

I pulled his nylon covered ass into me allowing his cock to fully enter my throat and then I felt Jere's penis grow larger and hotter, while his breathing grew faster.

I pulled his cock out from my throat a little and felt the first spasm, my choice had been made. I looked up at his face as he began to fill my wanting mouth with wad after wad of cum. After the initial jolt I just kept at it and actually loved the feeling of milking this "boy".

After at least six or seven shots, Jere calmed down as I continued to take the last spasms from his cock. With Sheri still working on me, I felt a deep feeling of orgasm building inside me, and I knew I was loosing control and was about to release my own load.

I let Jere's now soft member slip from my lips, and as I looked up at his girly face, swallowed his seed down my throat. I used my finger to scoop the bit of cream that was on my chin and licked my finger clean. Sheri hands were around my legs, caressing my hose, with my cock in her mouth as she moaned and moaned with each stroke of her lips.

As Jere's slippery cum went down my throat I lost control and Sheri felt my hot explosion. I squealled as I pumped load after load into her hungry mouth.

The orgasm I felt was much different from others I have had in that it was not just concentrated at my cock, but much more a whole body experience like a girl would have. She continued sucking me and stroking my legs as I experienced the first orgasm of my feminine life, it seamed to last as lot longer than a "normal" one.

As I came down from the amazing experience, Sheri got up and straddled me with a mouthful of my cum and kissed me fully on the lips. Our tongues swam in a pool of cream as we shared my wad together.

All three of sat on the couch after the erotic session we just concluded and recovered by kissing and rubbing each other until we came to our senses once again. Sheri then said, "I don't think we need to play spin the bottle anymore to decide what to do next." All three of us laughed and then began to kiss and fondle each other again looking like a group of hot lesbians getting ready for fun.

Sheri laid on the couch and Jere and I began a long session of servicing her as only girls can. As we licked and lapped at Sheri and we would stop and kiss each other deeply which Sheri enjoyed watching. After Sheri had several orgasms, she was content to watch the kissing and petting between Jere and I. We were both very excited and ready for the next step. I whispered to him that I needed him inside me as I stroked his beautiful cock in my hands.

He sat on the couch and lifted his dress to his waist exposing the pretty nylons covered legs I loved so much. I had managed to provide access to my back side by carefully cutting a hole in the pantyhose. With a little KY that I had on hand I lubricated Jere's tool up well.

I had never done this act before, but was feeling so feminine that I knew it was going to feel right. Lifting my hem up, I backed up and straddled Jere's legs targeting his cock into my ass. Sheri realized what we were going to do and jumped up to help me along. As I slowly worked in Jere's head which caused a little pain but also a lot of pleasure, Shere was kissing me and easying me down.

As I took more and more of Jere in, I began to feel fulfilled and more feminine then I ever had before. I groaned loudly as I came all the way down with Jere now as deep inside me as was possible.

Sheri was now kneeling in front of us and began licking and sucking my throbbing member. I began to pump up and down on Jere and was enjoying the pleasure of him inside me. After a few minutes his hot tool pulsed and expanded sending his warm cum deep into me. This triggered me as well, as Sheri, hearing my moans began milking me for a second time.

This time my orgasm lasted much longer and it took a full minute for me to come back to earth. When I recovered I was overcome with emotions at what had just occurred.

I believe I was happy, but also a little scared as to what I would do next and what direction my life would take. Jere and Sheri sensed some apprehension on my part and calmed me down a lot. Jere was living a nice life with his secret and I could as well, Sheri explained. She also suggested we all go out together including one of her girlfriends (real girl) who had been turned on when she found out about Jere's dressing habit.

We made plan to go shopping the next day in a nearby town and get some pretty clothes for me and Jere. And since no one was home at my house we would come back and have a fashion show. I agreed and felt much better and a little excited over the prospect of getting some clothes of my own.

To be continued.....if you all leave review for me.

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Written by Picone
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