My Real Life Crossdressing Experience

I have dressed in lingerie since the age of six. For as long as I can remember I have been fascinated with the idea of being a girl, and many times I wished I was one. As I grew older and moved out on my own I began to buy my own lingerie and learn how to apply makeup. I have had my makeup professionally applied and when I looked in the mirror with my wig on I was shocked at how pretty I looked. I naturally have the look of a biological female without much effort. My shoulders are rounded and I have a natural woman's hip and behind. I fill out my panties and am honestly more comfortable wearing a bra and panties than I am any male clothing. I have next to no natural body hair and the first time I shaved my entire body clean, the small amount of body hair I did have took several months to grow back. When it did it was much lighter and most of it did not return. I have shaved my body clean three times over the years and currently, if I shave it once more, I'm pretty sure almost all of it will not grow back. My penis is abnormally small and when it gets fully hard it measures only 1.5 inches. (Yes, I have measured.) It's almost like it was put there by mistake. I own a complete wardrobe of dresses, wigs, and makeup and I transform fully into a woman as often as I can. It has been very easy for me to pass in public for years.

I am an only child and never had any brothers or sisters to ask about sex so I never learned much about it. It wasn't until I was almost 25 years old that I had my first ejaculation, and even then it was when my cock was completely flaccid and very tiny. I thought I had wet my pants. When I got to the bathroom and pulled down my briefs I saw a soft mound of white cream and I was shocked at what had happened and it took me a couple of minutes to realize I was looking at semen. I was under the impression it would not be possible to orgasm since I had never done it before. Shortly after this event I started to teach myself to masturbate by pulling on my tiny cock. I was able to bring myself to climax using just two fingers to pull on myself because that's all I had to pull. I have since seen men use their entire hand when stroking their penis. I can never do that as I am way too small. The older I get the more convinced I am truly a girl. I tried to have intercourse three times with biological women, but I was not able to penetrate their vagina with my tiny "erect" penis. After the third failed embarrassing attempt I did not seek out females for sexual experiences.

When I was in my thirties I finally I built up enough courage to go on a date with a biological male. As I waited in my hotel suite for him to arrive my heart was pounding in my chest. I had spent most of the day perfecting my look and I must say I looked very, very pretty. I was wearing a dress and under it I had a satin and lace half slip and camisole. Under that I had a satin and lace bra and large nylon and lace panties. Under my panties I had a white satin & lace garter belt holding up my white lace top stockings. I had on a shoulder length red/brown wig and my fingernails and toenails were painted a very feminine shade of pink. My tiny penis had shrunk back into my body to the point the tiny head was not even visible. I was for all intents and purposes a total female.

When there was a knock at the door I slowly got up and answered it and a very nice looking gentlemen was standing there in slack pants and a casual shirt. When he identified himself as the man I had been expecting I opened the door wider to let him in. He had a bottle of champagne and some strawberries with him and one of the first things he said to me was "you are very beautiful." When he said that I thanked him for the compliment and felt myself completely relax. We shared champagne and strawberries and sat together on the sofa and I found myself very attracted to him in what felt like the most natural of ways. I shared several of pictures I had of myself in all sorts of poses as a woman. He was very kind and considerate.

His first move toward me on the sofa was to put his hand up behind my earrings and stroke my neck. This was followed by him sliding his hand up my leg under my dress on my stockings and gently brushing the front of my panties. He then leaned in to kiss me and as natural as can be my lips parted and so did his as we began a session of deep tongue kissing that I literally wanted to last forever. I think we deep kissed for at least twenty minutes with him running his hands all over me, and me, without any hesitation, stroking the crotch of his pants and feeling what to me was the biggest penis ever. I could feel it throbbing through his pants and he was becoming very excited. I felt totally turned on inside my body. I was thrilled that my tiny penis was still soft and still hiding inside my body. I felt completely female inside and out for the first time and all I wanted to do was to climb into bed with this beautiful male partner.

He stood up and took me by the hand and led me into the bedroom. The front of his pants was bulging way out. At the foot of the bed he stopped and took off his shoes and then asked me to turn around while he unzipped my dress. It fell to the floor and I was standing at the foot of the bed in my half slip and camisole. I turned back around and we began to deep kiss again and again. He gently lowered me onto the bed and climbed on top of me. We were still deep kissing on the bed when I think he noticed the wrist restraints that I had tied to the headboard. I was so into kissing him and feeling his huge cock in this pants rubbing on my leg I did not notice him gently raising my arms and putting me into the restraints. When we took a breath from kissing I noticed I was tied by my wrists to the bed. My tiny penis was still flaccid and small in my panties but inside I was boiling into a sexual feeling I had never experienced.

At this point he got up off the bed and had me watch him take his pants and boxers off. When he did I saw his thick, hard erection and I was shocked at how big it was. At least 7 inches long and sticking straight out! I think he saw my look of surprise as he climbed back onto the bed and he lowered the head of his erection to my lips and asked me to kiss it. I did this without hesitation, even adding a playful lick to it as he pulled it away. At that moment he pulled up my half slip and pulled down my panties to expose my tiny misplaced cock that I completely despised having between my legs. He began to pull at it as I begged him not to stimulate it. He did not stop. I kept begging him to stop as I thought this little organ was filthy and disgusting and as a girl I hated having it on my body. He did not stop and soon the tiny head popped out of my body and in no time was a full 1.5 hard inches. At this moment I began to cry. I was softly saying "no, no, no" as he still continued to manipulate my little nub. Before I knew it, my back arched up, I gasped for breath, and a stream of cum shot out of my little organ at least three feet into the air. I had never had an orgasm that intense when masturbating and the way it happened even surprised my partner. He gave me a big smile and dried my tears and told me not to cry but to relax and take his huge erection into my mouth. I did this quickly as he lowered it to me and with three long deep strokes I felt him tense up and in an instant shoot a full load of cum into my mouth which I swallowed almost instantly and began sucking on his rapidly shrinking member as if I was wanting to get every possible drop of what he had. It was wonderful!

Since that night we have seen each other on dates several times and we have begun to talk about moving in together as a couple. I would be able to fulfill a lifelong dream of wearing female clothing 24/7 and he has said he would love to climb into bed with a partner like me every night. We'll see what happens.

Just in case, I have started shopping on line for a satin and lace wedding gown as I would like to experience a wedding in front of a group of people with me being the bride and my new found love being the groom.