That is an EXCELLENT question and I am glad you asked! It is a really simple answer to be quite honest. Wearing a cage and a plug is the next step in my sexual evolution. I enjoy dressing and presenting as female, acting as a female during sex, but I am not truly experiencing sex as a female. The reason for that is that I still have my “male” parts aka my cock and my balls. I plan on keeping them, but I need to reprogram my body and mind to react as female. I still masturbate my cock, but now I do it as a girl would, rubbing it with 2 fingers under the head as if it were a clit. I also can… Read more

Early on, I kept my desires separated. Dressing up was only done at home and usually on the weekends. If I did go out, I would go to adult bookstores and enjoy sucking unknown cocks at the gloryhole booths. The booths were almost as filthy as the images on the screen, but hey, it’s practice, right? Finally I had gotten up the courage to let somebody see me and suck cock as a woman. For safety reasons I decided to underdress and bring some makeup and a wig and breasts in a backpack. My satin panties and bra felt soothing under my fall clothes as I took the Ashland Ave. bus to th… Read more

Vegas showgirl hair. Check. blood red lips and nails. Check. Sultry smoky eye. Check. Tight miniskirt to show off my ass. Check. Fishnets and 5 inch fuck me pumps. Check. The look was nothing new to me; it was my usual slutty whore look. I would wear it out to the adult bookstore to have fun at the gloryholes, watching the guys eye fuck me as I sauntered to a booth to take on all cummers. I had had plenty of cocks and was an excellent cock tease, but this was a special occasion: I was going to be spit roasted for the first time in my life. I was up late in a chatroom,… Read more

I had hit the neighborhood d**gstore for makeup, went shopping for sexy lingerie and club clothes at the local boutiques, had a killer pair of fuck me pumps, and had a ravishing Ann Margaret wig. I was ready to take the big plunge that every “gurl” like me dreams about. A club down the street from me hosted a shemale night once a week and instead of picking up a gurl, I wanted to be the one picked up. I wanted to look stunning and be treated like a little whore. I showered and shaved my legs silky smooth, my nails were done earlier in the day at a cute little spa, I had my sexy… Read more

I decided to use Halloween as a way to come out to my wife as a cross dresser. I had grown sick and tired of hiding my clothes and only having play time in my panties when she was not home. She was going as a sexy cop and asked me what I wanted to be. I suggested, in a joking way, that I go as a trashy hooker that she arrested. Her face lit up at the idea, so I decided to run with this limited opportunity that I had. I went out and bought more clothes and make up (always an excuse to shop!), grabbed a few items from my stash, and was dressed before she got home. Her response was bet… Read more

I usually didn't call any of the guys I'd meet on Craigslist before I had sex with them. Many men would put their phone numbers in the emails, but I never bothered, I just told them to come on over knowing they would get a blowjob from me and leave. I was usually so horny for cock that I didn't set up advance dates. If you weren't ready for me when I wanted to suck cock, you weren't getting me, end of story. But one day I got an email that was different and really got me hot. This man was married. Nothing new about that, I had lots of married men that wanted to fool around wi… Read more

I was really young when I got the urge to cross dress. It started at age six in summer camp. There was a trunk of clothes for the k**s to play dress up with. The men's jackets and suits were really boring, so I started putting on dresses and skirts instead and liked it! I enjoyed the sway of the skirts and would shake my hips like a hula dancer to see it wave. It progressed from there. From age 8 and into my high school years I would raid my mom's or sister's closets if I was home from school and sick. I loved the feel of the satin panties on my young body, and it was fun pr… Read more

When I was 18, I had a copy of Variations magazine. I knew all the letters in it were bullshit, but there was one that really got me hard. It was about a college k** who met another man in his dorm and was "initiated" into college by being forced to get his cock sucked and get fucked by his male roommate. The idea was planted into my mind that I wanted to see what it was like to suck a cock. I got my chance just a few months later. I went to a party in the city, a party with a bunch of art students. Somebody told me about a man to watch out for. They said that he fucks anyth… Read more