My First Time Dressing

My First Time Dressing
Story Synopsis: My cousin opens up my female side.
When I was about 18, I would spend my summer vacations, from school, at my uncle’s house. My cousin and I would sleep in one bedroom, with two beds. He was three years older than me and always knew what we could do, to have fun. I looked up to him and wanted to be like him. We had no secrets between us, and we shared everything.
One afternoon I came home early, from a friend’s house and found my cousin standing in front of a full-length mirror, dressed in a blond wig, black nylons, yellow panties, a bra, and a yellow summer dress. I could see he was stroking himself under the dress. At first, he was so into seeing himself, he didn’t know I was there. Standing in the hall, I got very excited and hard watching him! He made a very comely girl. I had to stare to see if it really was him. I was shocked at how turned on it made me, to stand there, watching him.
After a few minutes, he must have heard me, because he turned around and smiled. I knew I was busted, so I walked in.
He slowly walked over, reached out, and stroked the front of my pants. He said, “You must have liked what you saw”. I was so shocked; all I could do was stand there and nod. Then he asked me if I’d like to feel what he felt like. I wasn’t sure I knew what he was asking, but again, all I could do was nod.
He took my hand and placed it under his dress and over his bulge. I couldn’t believe how hot it felt. I could feel his penis getting bigger under the soft panties he wore.
I started stroking him, through the material. He closed his eyes and told me it felt so good. After a few minutes, again he asked me if I’d like to know what it felt like. I told him, yes and without a word, I started undressing.
He had an old suitcase he kept his woman’s clothes in and after picking out some clothes, which he laid out on his bed, he showed me how to put them on. First the garter belt, then nylons, panties, bra, and a dress. To top it off he gave me a black wig and showed me how to put it on. He only had one pair of high heels, so I went without.
After we were dressed, it felt so strange but sexy and I was excited all the time. I loved the feel of nylons on my legs, the breeze blowing up my dress, and everything you don’t get in pants. I knew I didn’t look like a woman, but I could feel what a woman felt.
After that, we’d spend hours walking around the house, trying on different outfits. We’d walk around the house, calling each other “faggot boy” and “sissy boy”. It was fun, but when he put his hands on me, it was even better. He had a light touch, never rushing or harsh. Even when I wanted him to rush, he took his time. We stroked each other and I got so hard, it almost hurt. I looked forward to the feel of his hands on my thigh, sliding up to my panties.
One day, while sitting on his bed, he kissed me on the cheek, and he told me to stand up. Standing in front of him, he slowly pulled down my panties. My hard penis stuck out and pointed right at him. Then he went to his knees and I almost fainted, as he started sucking on my hard cock. It didn’t take long before I exploded in the strongest climax I’d ever had. After I climaxed and he swallowed, he told me he’d wanted to do that for a long time. Because of the smile on his face, I knew it was only the first of many times he’d do that.
Then, a few nights later, with my uncle home, I woke up to find my cousin in my bed, stroking me. Once I got hard, I felt his warm mouth as he sucked on me. He took his time and slowly built me up to climaxing and swallowing every drop. It was so hard to be quiet while shooting load after load, but somehow, I didn’t make a sound.
After I’d climaxed, he went back to his bed, like it was all a dream. From then on, when we’d be alone, we’d dress up and “play sex games”. When my uncle was home, he’d visit me in bed that night and suck me off. He never asked me to do anything for him, seeming to get as much pleasure out of sucking me, as I got.
I looked forward to being awakened, with his mouth sucking my small cock hard until I exploded with pleasure. All too soon it was time to go home and back to school again. That school year was a long one, being away from him and his willing mouth.
The next time we were together, I wanted to try it and see what it was like to have a hard cock in my mouth. I now knew what it felt like to be sucked, by someone who wanted it all the time, but I wanted to know what he found so pleasurable.
I waited until we were alone and dressed. I told him I wanted to be shown how to suck as he did. He had me get on my knees and slowly stroke his legs, working my way up. He told me he’d tell me before he climaxed, in case I didn’t want to swallow his cum.
When I got to his panties I couldn’t stop, I had to taste him. I shut my eyes and put him in my mouth. Slowly, I worked him in and out, deeper and faster. I became lost in the feelings and when he said he was going to climax, I couldn’t stop sucking and swallowing when I felt the hot cum shoot into my mouth.
The taste was salty, but like nothing, I’d ever tasted before. I kept licking and sucking on him until he was hard again. He looked down and told me I was a “good cock sucker” and it sent a thrill through me. After that, I knew how it felt to get pleasure from giving someone else pleasure.
This went on for three more years until my cousin left to go into the Army. I tried to go back to my “male life” and hid my feelings but couldn’t get that feeling out of my head. I’d relive it over and over when I’d masturbate. Even when I had my first girl, I’d think how wonderful it would be, to have his cock to suck on, as I pounded into her pussy. This went on until I went to college.
While there, I met and befriended another crossdresser and it all came back again. While with him, I met my future wife.