Admitting My Desires

I've finally been able to admit to myself who and what I am. This is my first story here and it's a....... how I got here story. All are true and nobody is under 18 in any of the time frames.

It all started with........ a couple of my friends and I got some dirty magazines after finally being old enough. We started looking at them together. We progressed to stroking in the same room together. It then went from stroking to stroking each other. Of course, I know that I ended up going further to 1:1 with each of them. This included oral sex.

At home my hormones were going crazy - I was a late bloomer. I started realizing that stroking with KY Jelly was so much better than dry. I also found that my mother and sister's panties were exciting. I migrated from rubbing my cock with them to smelling and tasting them and yes, wearing them.

Slowly over time I came to realize that wearing them made me feel submissive and girly - and I really liked it. Anytime I could find time alone in my house I started dressing in mommy's things. I really hoped she'd catch me sometime.

Being that she was a single mother and space in the house was limited I often would sleep in mommy's bed if she was out - multiple kids and she had the only other TV in the house - even if over 18 it was still exciting being in mommys bed. When she came home, she wouldn't wake me to go in my own room.

I remember my last night in bed with Mommy. She came home and I was asleep. I woke after she was asleep and realized that I'd been rubbing against mommy and had a wet dream. I'd cum all over her satiny long nightgown and myself. Mommy woke up and had a look of shock. She told me everything was ok and that im now too old to be sleeping in mommys bed. she said that I needed to go put dry pajamas on and get in my bed.

Although that was my last night in bed with mommy my desires grew from there. If i wore her things I would often act like she was in them, and I was grinding on her. Such amazing orgasms.

After I went to college I found Adult Bookstores. When I first went in, I browsed the store. After that I started going into booths, watching straight, gay, tranny, cross dressing and incest movies. I slowly learned what a finger through the Gloryhole meant. The first times I just peeked through the holes after the finger was poked in. Over time I decided to poke my finger in. Immediately a cock was pushed through into my booth. I'd love to tell you I grabbed it and got on my knees to suck it - I actually panicked and left.

I thought about that for the entire evening. I went back the next day after my classes. This time when that cock came through after my finger I started stroking it. I stroked that cock for a few minutes and the cock withdrew. Then a finger came through. I figured why not get stroked by someone else. I then put my cock in the hole. I was shocked when I felt my cock get engulfed by a warm and wet mouth. I was now hooked. I also now knew what that man/cock had been expecting. After I came, I again panicked and left.

My next and subsequent visits I would always suck cock before letting them suck my cock. I started borrowing my mom's panties and wearing them to the Gloryholes. I really enjoyed sitting there in just panties and having men look at me through the gloryholes. I really liked when they would talk to me and call me names. That was the first time I was called a Sissy Cocksucker.

I ended up meeting a girl at school who admitted she sometimes went to the ABS as well to look at toys, magazines and videos. I told her there were video booths with porn playing. She had no idea - I didn't tell her about the holes.

One weekend night we were in our dorm, and she asked if we could go together. I couldn't believe she brought up what I'd been thinking about for weeks. I agreed and off we went.

Once inside she grabbed my hand and said show me...... my reply was simply - The Booths? She nodded and smirked so off we went. When we made it out back there were 10 booths and easily 5 to 6 men hanging in the hall. The booths were half full. when we entered the booth, I put my money in, and she started changing the channels. After our eyes adjusted and she picked a movie she pointed to the wall and giggled. I acted shocked to see a finger poking around the hole. we whispered to each other about it.

She asked if I knew what it meant, and I told her I didn't notice the holes before. We each started peaking in a hole on each side. Come to find out we were both watching a man stroke his cock live. we swapped sides for a few minutes. It was at that point that she grabbed me. Her guy had stuck his cock through. I wasn't prepared to show or explain my desires, so I simply said, stroke it.

She giggled but grabbed that cock. he clearly wasn't fully hard yet as I swear, he grew 3 more inches to about 8+ in total.

After a bit I said, "why don't you suck that big cock" She was excited and got down on her knees and started licking and sucking that cock. I couldn't believe she just did it. I was jealous for sure. I couldn't wait to go back alone so I could be the one on my knees.

From that point on I realized for sure that I enjoyed this side of me more than I ever expected. As a young adult I had the more traditional relationships. I can tell now I was going through the motions. I was conforming to the norm. What wasn't the norm is that those relationships (including marriage) allowed me to have a live in supply of panties. This became my new vice. When the internet really got ramped up, I started finding chat rooms. These allowed me to talk to other men that had the same desires or even better men that liked men like me....... Sissy's In Panties.

I explored this as much as time allowed and found my way to a few ABS still on occasion. I was able to meet a few men for meet ups. They had mixed results. There is one older man that invited me to his home for dinner. If I have a regret, it's that I didn't take my chance that night to explore more with him. I was a nervous late twenty's guy. I enjoyed the dinner and conversation, and he was handsome. I wish I opened up more and explored.

Later in life after divorce I met a woman that was as kinky and open as I always wanted to be. We met off Craigslist of all things. She was offering erotic massage and I just really felt like I needed something different. Different I sure got. She was a very genuine and kind sole.

Her massage was amazing and quite sensual. I trusted her immediately. She was the first person I was ever able to share my thoughts of Mommy and Dressing. She just brought it out of me.

Eventually we became a couple, she convinced me to let her dress me fully. Having been an entertainer and in theatre she had a lot of clothes, wigs, shoes and such. I was amazed at what she was able to do. She eventually started taking pics of me which I loved. We moved on from that to driving around and even me pumping gas or going in a random convenience store late at night. It came to a point where we discussed her and I having a threesome with another man.

She had a "client" that always wanted to do more than she had been willing to before. She asked him if he would consider joining us. Suffice to say he was ecstatic. She didn't tell me what they discussed us doing but by was I surprised the night of the get together. I came home and she said - GO SHOWER. I expect you to shave fully from the neck down and your face.

After nearly an hour in the bathroom getting smooth, I came out. She sat me down at the make-up table and started transforming me into Sissy Ashlee as she called me. I kept asking me what her client would think. She finally said relax...... he knows and is very excited for you to prepare him to fuck me. That is exactly what happened. He showed up and I was waiting in the bedroom. I heard them out in the hallway when he walked in. I could tell they were making out. It turned me on to know she was on the other side of the wall with another man. She said later that what turned her on was knowing she was making out with a man while her Sissy GURLfriend was dressed and ready to enjoy cock with her.

When he came in the room he came right over and hugged me. This was his chance to feel me up. I took the opportunity to do the same. I then knelt down and started to undress this man. I got him naked and sat him on the bed. He then instructed me to be a good Sissy Faggot and suck his cock till he was rock hard for my lady. I wasted no time licking and sucking this hard cock presented to me. He had to stop me from making him cum. At that point he instructed me to step back. My girlfriend then got on the bed and started making out with him. She had stripped completely while I was servicing his cock, so they were both naked now. Eventually it was time for me to see her taken by another cock.

She said, Sissy get over here and but this man cock inside me - now. That was still to this day one of the sexiest memories I have. I took hold of his cock and started to guide it into her wet folds. She was moaning like I never heard before. I couldn't stop from getting behind him so I could watch her get satisfied by a real man. This went on and on for almost thirty minutes. She was begging him to breed her pussy. She pleaded for him to knock her up so her "sissy" could care for their baby. He certainly couldn't hold back with all that dirty talk and filled that pussy with more cum than I have ever seen in a pussy. When he got off her all I could see was her sweet, engorged, creamy pussy with cum all over it.

What happened next was unexpected for me. I was instructed that if I ever wanted that pussy or this night to happen again it was time for me to clean up. She saw that I wasn't sure what she meant so she made it clear - get over here and eat that cum from my pussy - don't leave a drop there.

The whole time I was doing as instructed she was degrading me and telling me that she needed real cock more often and I would be her fluffer and clean up sissy. This went on for a few years. I wish it never ended to be honest.

After many years and many life's experiences later I'm exploring more and more.

If there is a desire for "Chapter 2" I will write it. There is so many more years of fun and stories.