It Was Inevitable

It started like many crossdressers borrowing my clothes from mom. I was commuting to college at that time and sadly had no social life. My parents liked to go out on Saturday night. which gave me the opportunity to explore my fetish.

I had a huge nylon curiosity loving looking at girls in skirts and stockings. One night I went looking for mom's girdle and stockings in the laundry. Even putting the girdle on started giving me a hard on. When I put on the stockings my cock was as hard as a rock.

Walking around dressed like this for the first time was an unbelievable feeling. It felt like this was how I was meant to dress. I knew I did not have much time before parents got home so I found a spot to sit down and jerk off. As I was rubbing my cock I was also moving my nylon covered legs together and the feeling was glorious. I came shortly after I started. Fortunately I had tissues handy so I didn't stain the girdle or the stockings.

I knew already that I was hooked forever and my desire for anything nylon only increased as I got older. The next couple of years saw me expanding to "borrow" from my neighbors. One day I saw a dress hanging from a clothesline at the house to our left. Naturally that night I snuck over and took the dress to our basement. It was a little damp but that didn't stop my cock from getting super hard. I loved the feeling of the dress on my thighs and wished I had more time. I was starting to get nervous and reluctantly took it off and jerked off. I rushed back to the clothesline and hung it up. I am sure that it wasn't close to how they had it but I was panicking and in a hurry.

I was so relieved that I didn't get caught that I stopped everything for a couple of weeks. I was getting hornier by the day and keeping an eye on my neighbor to our right.

I knew where they kept a key and I just needed a night when they weren't home.

Finally on Saturday night my parents and neighbors were both out. I snuck over and got the key from their hiding place and carefully opened the back door. Lucky for me they had left a lamp in the living room on so it wasn't pitch black. The reason I wanted to be there was their two daughters and I wanted to try on their clothes. When I got to their room I noticed that the curtains were closed so I risked turning on a light,

I went immediately to one of the dressers and began opening drawers. It had to be the older sister's dresser because the size was closer to my size. Younger sister was very small. I quickly undressed and put on a pair of her panties followed by a full slip. Talk about instant hardons! This did the trick and I was in heaven. I also knew that I couldn't stay dressed like this for long risking cumming in her panties. How I wanted to steal them but couldn't take a chance. I was frustrated not being able to cum but also increasingly nervous about getting caught. As I was leaving and hiding the key a light came on at the house next door and somebody yelled who's there.

I dropped to the ground and snuck back to my yard. Then I ran straight to the basement, my heart pounding in my chest.

I sat for a while catching my breath thinking what the fuck was I doing. Risking get caught for breaking and entering just to try on panties and a slip.

The next few years in college flew by with a few changes. I continued raiding the laundry even adding a slip and a dress of mom's to my outfit. I was scared shitless one night when my parents came home early. Luckily I saw the headlights of the car in the driveway and ran upstairs to my room. Too close a call and I backed off wearing her clothes for a long time.

I graduated from college and started my summer job, saving money for grad schooI was looking forward to heading out to be on my own and hopefully finally get laid.

Then the biggest shock of my life hit like a ton of bricks.

My parents were hit by a tour bus going the wrong way on the highway. It was a head on collision and they were both killed instantly. After the initial shock wore off one of my aunts got me a lawyer. The bus company quickly settled not wishing to go to trial. My share was plenty, enough to pay off the house, buy a new car and have a nice amount in a savings account. I postponed grad school and tried to put my life in order. I knew it wouldn't be easy but I needed to try.

Time is a good healer and I got to the point where life goes on. Part of that began with the discovery of catalog shopping. I went in full force happy that I didn't have to face any saleswomen wondering why I was buying pantyhose and other things. But buy I did, pantyhose, stockings, garter belts, slips and dresses. Lots of pretty lingerie, all nylon of course. I even bought a pair of high heels which took me a while to get used to. Once I did I loved walking around them dressed fully heels clicking on the floor. So exciting!

I will end my first story with another first in my life.

Around the same time of the catalog shopping I discovered the joys of New York City especially Grenwich Village.

It was around this time that I started wearing pantyhose under my pants to work. I loved the feeling of my legs walking in them, not as sexy as walking around the house in a dress but still good.

I finally got the guts to head to the village and took a train into New York. I walked around and finally decided to go into a bar. I figured I needed a bit of liquid courage.

I was finishing my first drink when a guy sat down next to me. He asked if he could buy me another one. I was shocked but quickly said yes. He was very good looking and much bigger than me. We talked for a while and had another drink. All of a sudden I felt his hand on my thigh. I was surprised but excited and let him rub my pants. He smiled and asked if I was wearing stockings. I sort of giggled and said pantyhose. He said this is too good to be true, you have to come with me. Before I had time to think he grabbed my hand and led me out of the bar.

Fortunately it was a short walk to his apartment so I had no time to chicken out.

As soon as we got inside he grabbed me and put his lips to mine, quickly followed by his tongue in my mouth. I had made out with a few women and enjoyed it but none of those times compared to this. I was loving every minute of it and was in no rush to stop. After an incredible few minutes he pulled away and told me to take my pants off because he had to see my legs. I took my shoes, socks and pants off as fast as possible and was standing in just my shirt and pantyhose. He stood up and started rubbing my legs up and down including

my hard cock just a little. We started kissing again and he grabbed my ass, squeezing and sticking his finger into my hole. I moaned and he said that's for another day. No get down on your knees and take care of your man. Without thinking, I obeyed and took his beautiful cock in my hand. First time I had touched anything but my own. All the blowjob porn I had watched came in handy. I started by licking his head, down the shaft to his balls and below. Back up again as he started to moan. I was only partially surprised how much I liked it, thinking I had always wanted this. I started sucking and taking more of his cock in my mouth. He was moaning so I knew I was doing something right. I didn't think I could take all of his cock in my mouth but it didn't matter. He yelled he was cumming and his sissy slut better swallow it all. Of course I did what he wanted, loving the fact that he was the boss. I even liked the taste of his cum and swallowed it all. He then began stroking my cock through the pantyhose and I was so turned on I came immediately.

He said you're sleeping over and taking care of your man tomorrow morning.

I just smiled and said yes sir.