Blackmailed Sissy Falls In Love

My biggest secret has always been that I love to crossdress. Nothing is more exciting or makes me feel happier than dressing up as a girl. Nobody knows I constantly crave crossdressing and that I secretly do it whenever I get the chance.

Gradually, a desire to have sex with men began to emerge whenever I would crossdress, but I was always too scared to do it and embarrassed that I had desires like that. I lied to myself that I didn't really want it, but the feelings just kept getting stronger.

One weekend when I was in my early 20s, my girlfriend Lori traveled back to see her family and I had our apartment entirely to myself for a whole week. I had never had so much time to explore my secret desires.

My girlfriend was the same size as me and I spent every evening getting totally dressed up in her sexy clothes, lingerie, make-up, and lipstick and cumming so hard to the fantasy of a big man totally dominating me. I wanted to go outside so badly and walk the streets and get picked up but I was way too scared to do it.

It was the fifth night, I will never forget it, when someone started knocking on the door. I was totally dressed up and close to cumming and my heart started racing! There was no way I could answer the door so I figured I would just ignore it and they would go away, but whoever it was kept knocking, as if they knew I was there and we're not going to go away until I opened the door.

I began to get really scared and so I crept out of the bedroom and went to the door and softly said, "Who it it"? A deep voice responded with a stern "This is Reggie from next-door. You need to let me in right now. I'm not leaving until you do."

I couldn't believe what I was hearing! Reggie was this big mean looking black guy that was always playing music really loud and was very intimidating. I always got really nervous whenever I ran into him in the hallway. This was my worst nightmare come true. I tried to say I was really busy but he kept insisting so I said hold on and ran to the bedroom and threw on whatever I could find over my nylons, panties and negligee and went back to the door, cracked it open, and asked what he wanted.

He said, "I like your lipstick, bitch". I had totally forgotten about the makeup and lipstick and felt that rush of heat through my body knowing I was totally busted.

Before I knew what was happening he pushed his way through the door, locked it and put the chain on, grabbed me by the hair, roughly led me to the bedroom, and threw me on the bed. I started crying and begging him to please not hurt me but all he did was laugh.

He immediately unbuckled his belt and pants and pulled out this enormous uncut black cock and said he was going to teach me a lesson I would never forget for being a closet sissy bitch tease. I was absolutely appalled and begged him not to do anything to me, but all he did was grab my hair and force my mouth onto his cock.

I felt it getting bigger and harder in my mouth and I kept crying because I knew I would have to face the fact for the rest of my life that I had sucked a cock. How could I ever look at my girlfriend again or any girl for that matter? All he did was take out his phone and start recording everything and saying "Shut the fuck up, bitch".

I begged him to stop but it was obvious he wasn't going to. He kept calling me all kinds of names and that he was going to teach me how to be a good girl. He kept fucking my mouth and moaning. I could taste his cum and kept gagging but he wouldn't stop.

Finally, he pulled his cock out of my mouth and then leaned over and forced me to kiss him, shoving his tongue deep in my mouth and keeping it there. All I could think about was how I was going to face my girlfriend when she came back. What scared me the most though was that a little part of me actually liked what was happening. I couldn't help but think that it had been just a matter of time before something like this would happen. I had been playing with fire.

Reggie said he had looked around his balcony and seen me through the window a few times and had also heard me moaning when I came. He told me next time I should close the curtains and windows when I feel like being a sissy bitch.

Next thing I knew, he grabbed me by the hair and forced me onto my hands and knees and began spanking me mercilessly. He kept saying he was going to break me and turn me into a black cock whore. I begged him to stop but he didn't until my ass was absolutely burning and I knew it would hurt for days.

He threw me back on my back and grabbed some of my ties and tied my wrists and ankles to the bedposts. He then proceeded to shove his cock back into my mouth and feel my body very roughly and squeeze my tits really hard. I knew I was going to have bruises and be sore for days.

He kept filming everything with his phone and telling me that he would show it to my girlfriend and family if I ever said anything. I begged him to stop and told him that I would never say a word to anyone, ever! But he just kept going. He was insatiable!

My absolute biggest fear was that he was going to stick that big cock in my ass! He seemed to sense what I was thinking and said that he was not going to fuck me in the ass yet because he was going to train me to be able to take it properly. He said I was going to become his whore.

I could tell that he was about to cum and suddenly he pulled his cock out of my mouth and shot a massive load all over my face and tits. He moaned so loudly I was certain other neighbors would hear.

All he did was put his clothes back on after he shot his load, said "you like that shit, don't you bitch", and got ready to leave. He told me to give him my phone number and that when he wanted me again he would text me and that I better show up or else.

He untied me and left me on the bed laying there completely spent with his thick cum slowly drying on my face and body. I had such an overwhelming mix of feelings I didn't know what to do! I was mostly thankful that he had not fucked me with that huge cock as I was certain it would've put me in the hospital with a torn hole. I also felt so much shame and humiliation I couldn't believe it. And I knew that it was going to destroy my relationship with my girlfriend. I wondered how I could possibly go back to my former life, which seemed so distant now.

The next morning I felt a little better thinking that I could keep the whole thing secret and that one time wasn't such a big deal. I kept trying to convince myself that I was still straight, but every time I sat down or touched my tits they were totally sore and reminded me of the whole thing, and I couldn't deny that it kind of excited me to remember what had happened.

A few more days passed, my girlfriend Lori returned, and in a way things started to get back to normal but all I could think about was what had happened and if he was going to text me. The more time passed the more the memories excited me. I actually started to hope that he would text me, but at the same time I totally didn't want him to because I was really scared about all the mixture of feelings I was having.

After about a month, after I had almost stopped thinking about it every single second of the day, the text came. He told me that I was going to follow every single thing he commanded me to do and if I didn't my girlfriend and family would immediately get the video.

For the next year, Reggie took complete control of my life and turned me into a black cock whore just as he had said he would. Within a month Lori was gone because I would vanish for hours and she knew I was lying about where I had been. I also totally stopped having sex with her. She was certain I was having an affair with another woman and would never have dreamed what I was really doing.

Reggie bought me all kinds of outfits and lingerie and put me through all kinds of wild fantasies and sexual situations. He kept my sissy clit in really tight chastity for weeks at a time so I could never cum and remained absolutely cock crazy all the time. Every once in a while he would finally let me make my sissy clit squirt and I would be so thankful.

He feminized me as much as he could and broke me down to the point where I was his sex slave. He gradually trained my ass to be able to take him, making me wear increasingly larger but plugs for extended periods of time. After about 3 months, he finally inserted his beautiful cock into my sissy pussy.

He was very patient about it because he knew what was going to happen to me if he trained me properly to take it. The first time he put his cock in me he only pushed it in about an inch and then pumped a load into me. After a few more weeks I was able to take most of it and I fell in love with him. I would dreamily French kiss him for hours and suck on his tongue. His cock deep inside of me was the most amazing feeling I've ever had and ever will have! And when he pumped his load deep inside of me I could not have felt happier. I wanted him to put a ring on my finger, be a sissy bride, and be impregnated by him.

After about six months he started bringing some of his friends in and I was broken in to being gangbanged regularly. He also started taking me out to clubs and whoring me out for money. He turned me into a complete popper and coke whore. He had numerous tattoos put all over my body, "sissy bitch" on my ass, "black cock whore" on my chest, all kinds of slutty things.

After about two years of this incredible life, which I had initially dreaded but grew to love and accept, Reggie was killed in a bar fight and I was suddenly left completely on my own. It was incredibly hard at first, but many of his friends who had gangbanged me, stepped in and took control. Mostly they use me but occasionally they prostitute me out to businessmen. I live completely as a female now and have not been with a woman since Lori and probably never will be again, especially with all these tattoos all over my body that make it crystal clear what I am. I miss Reggie every day. He turned me into what I now know I was born to be, and I will always love him.