My Journey to Sissy Heaven

My Journey to Sissy Heaven

Posted on November 14, 2015

How did I end up here? I couldn't believe what just happened! I was in a daze from what I just did. I was neither sickened or disgusted by it, I was just surprised that I had come so far.

Here I was, on my knees with cum drizzling down my face. Something that I have fantasized about for years, but was never able to gather enough bravery to step out and try it. I was so very happy that I finally got my first taste! Why did I wait so long to do this?

I can almost remember the first time I had seen a porn with a transsexual in it. I was caught so unawares, but could not stop watching. She was so gorgeous! It was a lesbian porn that I had thought I was watching at first. Lesbian porn was the only porn that turned me on anymore, so I would search and search for any new videos that I could find. It got to the point that I even started imagining that I was a girl and was coerced into lesbian sex by some sexy looking woman. So when this transsexual first took off her panties and her cock came out, I was pleasantly surprised that such a good looking girl could have such a big cock. I always knew they were around and I had even gone to school with one, but I never thought it possible that I would be attracted to any. 

I ended up having the best orgasm I had had in a very long time! I knew now that things would never be the same. I was possessed with lust and desire that took over my every thought! I started looking at women that I walked past to see if they had a bulge hidden in their pants. 

This went on for a few more years.

Then one day, while I was watching one of these videos, I thought that I should try sticking a finger in my bum while masturbating. It hurt the first few times that I did it, but I kept on until it became so addicting that I needed something more than a finger. The next time I went to the supermarket I bought some small cucumbers with the intent of using at least one of them on myself. That changed everything I had ever said about being gay or anal in the past. I had the most amazing orgasm with that cucumber up my ass! I now knew how guys could become addicted to cock and liked being fucked. I eventually worked up the nerve, after three months of cucumbers, to go to the local sex shop and buy myself a dildo.

As soon as I made it home I washed the dildo and made sure I was properly lubed up. I started as slow as I could to work it in. The head was massive! It hurt like hell! But I knew how good it would feel in a short while, so I kept at it until I finally had the whole thing in. My dick was harder than it had ever been in the past. 

I out on my favourite shemale porno and played with ass until I came. I didn't even have to touch my dick. This was first of many anal orgasms over the next two years. My desire for a transsexual to take me from behind grew and grew. But I could never bring myself to go and do anything about it. 

That is until I decided to move to the city.

I had been living in Vancouver for two months now and had met this girl that gave me a new sexual passion. She knew how to make a man cum! She worked out over time that I liked my ass being played with, so whenever she would give me a blowjob she also would finger me. I was in heaven! I thought now I can put this tranny thing behind me! Boy, was I ever wrong! This only made my lust for cock even greater! I needed to know what one felt like other than my own. 

I was staying at her house for a few days while I was looking for a new place to live and I was introduced to a whole new life! She was off at work for the day. I knew where she kept her dildos and knew that she owned one that was eight inches long by about two inches thick. I had sat and stared at it forever, wondering how it would feel to ride. I had never had anything so big in me before. My dildo, that I had hidden away from her, was only five inches long and just an inch thick. I had plenty of time to play around and figure it out. So that is what I did.

I stripped myself naked and washed up. I had already been shaving my bum and my cock since I started dating her, so I didn't have to get rid of any unwanted hairs or anything. I started rubbing some of her lotion on my opening and fingering myself in preparation. After a few minutes of this, I thought I should be ready for the Monster dildo. I grabbed it and slowly started to ride it. getting it further and further in with each thrust.

I put on some shemale porn and was scrolling through the website when I saw some crossdresser video. I decided to put it on as it was a tranny fucking a crossdresser. The crossdresser looked like he was in heaven. I then stopped what I was doing and rifled through my girlfriend's closet. She was a bigger girl, so I knew that I shouldn't have a problem fitting into her clothes. If I was going to be fucking myself with such a big dildo, I figured I should dress the part too. I found a black thong and put it on as best as I could. I then found a matching black bra and tried ever so hard to put it on until I figured out that I could put it on backwards and then slide it around. I then found some tights that I slid up my legs. She had quite a few dresses to choose from. It took me forever to decide which one to put on. I finally went with a knee length black and white polka dotted sundress. She had some wigs that I attempted to put on. I grabbed her lipstick and very poorly put it on. I looked a mess! But I didn't care. I was so turned on and knew that I needed to fuck this monster dildo until I came. I had it stuck onto the wall so I could back up onto it with the least amount of effort.

I was there for more than an hour riding that cock in as many different positions as I could think of! I didn't want to touch my cock, I needed to cum by anal only! I knew how good it felt and didn't want to speed up the process at all. I finally came with the dildo on the floor and me riding on it up and down as fast and as hard as I could go. I came everywhere! I realized that I might be in trouble if she saw any cum stains on her dress! I quickly whipped it off and cleaned it as best I could and stuck right back where I got it from.

I never did any of this again. Even though I dreamt about it every night after. We ended up breaking up five months later and never seeing each other again. I was now free to do as I pleased! I started buying my own clothes. Slowly at first. But then it became an addiction. Every time I went to the mall I would look in the lingerie stores and seeing what was out there. I started shaving my legs and underarms and chest. I would dress up any chance I could! I would turn down going out with friends so I could dress up and fuck myself. I started watching tutorials on how to apply makeup. I even went as far as to go to the mall and purchase a dress.

I went online and found chat sites that catered to crossdressers and transsexuals. I gave myself a female name. I then started to wonder if I should even get a man to fuck me instead of trying to find a tranny to do the job. After many online searches, I made a profile on a tranny dating site. I made my search broad. Not only was I looking for a transsexaul, but I was now also looking for any willing men that would like to take me too. I did some webcams with a few men and some trannys. Never once was that enough. I needed the real thing! Not just online play. So I made a craigslist ad.

I had countless replies. So many men that wanted to be my first. I picked carefully, trying to make sure that I would be safe and not beaten up and robbed. I drove to meet someone to give him a blowjob in his truck. I sat and waited for an hour before I realized he didn't intend to show. I was devastated! It took me a few more weeks before I made another ad. This time I replied back to everyone. Finally I was able to get a guy to commit to meeting me. 

I sat and practised my makeup countless times in preparation of meeting this guy. I would never be as hot or as convincing as I would like. But that didn't stop me from trying. 

He wanted me to show up at his house fully dressed. That was the longest drive I have ever had to do. Even though it was night time, it felt like everyone I passed knew what I was up to. I pulled up to his house and sat there for a good twenty minutes working up the courage to go knock on the door. I was just about to drive off when I saw his front door open and him running over to my car to see if I was alright. It was too late. I couldn't back out now, could I? I didn't think so. He was so friendly and caring. He opened my door and I stepped out. I know I didn't look very girly and hot, but he whispered in my ear and told me how much he wanted me. 

I was putty in his hands now. We slowly walked up his driveway and into his house. I was now committed. He asked if I would like a glass of wine. Of course I said yes! I needed some liquid courage. I was so nervous! I have never sucked on a cock or even touched one other then my own. And here I was, in some stranger's house getting ready to suck him off and let him fuck me. I wasn't even attracted to men, I just needed to taste some cock for myself. 

After six glasses of wine, I was as ready as I would ever be. So I told him we should go to his room where we could get a little more comfortable. We got to his room and he turned around and kissed me square on the lips. Caught me fully by surprise. I didn't know what to do at first. I finally decided what was the problem with kissing him? Here you are in his room, dressed in drag, getting ready to give him a blowjob. Might as well enjoy the kiss. 

He backed me up till my legs hit his bed and he forced me to lie on my back. He crawled on top of me and started fondling my chest. At this point in time, I dearly wished I had some breasts. I would have loved to know what it felt like to be felt up. I could feel his crotch on my leg, slowly thrusting back and forth. Up and down my leg. making himself harder and harder. He then suddenly stood up at the edge of the bed and told me to undo his belt. I sat up and did as he asked. I pulled his pants down until the reached hi ankles. His cock was bulging through his boxers. I suddenly forgot who I was and kissed the tip through his boxers. Tasting him ever so slightly. I had no inhibitions now! I needed that cock in my mouth! My inner lust took over and I grabbed his waste and started kissing him all around his crotch.

I then slid his underwear down and let his cock escape. OH MY!! It was a thing of beauty! I looked and admired it for a a little bit before I started to lick the tip. I slowly kissed his cock from the head down the shaft. Taking his balls, one at a time, into my mouth. I then worked my way back up the shaft and took the head in my mouth. Working my tongue over the tip. Playing with it. Making him as hard as I could. I couldn't help myself, I needed this cock so bad! It was everything I had been working towards for the last four years. 

I let him take control form that point on. I needed to know what it felt like to be the girl. The one being fucked like a slut! I knew from this day on that I would be a cock slut! A cum whore! I needed to be treated like the sissy slut I had finally become! 

Now if only I was more feminine. I knew what I needed to do.

Story by: Corina84