The Path to Happiness Pt. 05

Today was the day, I will be leaving this town today forever. I now identify myself as a girl, this town is a reminder I was born as a boy. After today I can finally walk free without fear of being outed buy some idiot who knows my past.

I had an early alarm call at 6.30am, I showered and shaved and dressed in my underwear, school blouse, and skirt. Next I fitted my wig and glued down the lace front and applied some light makeup.

After a lite breakfast, I put on my tie and pullover. I loaded the last of my stuff into my backpack. I sat down and finished my coffee, whilst reflecting the last five weeks. Five weeks ago, I was an 18-year-old boy discovering his homosexuality. Four weeks ago, I was a male prostitute, then 3 weeks I had become a tranny prostitute. And now I'm living fulltime as a woman, about to start university.

I noticed the clock read 7.15, time to get to school. I pulled on my blazer and slung my backpack over my shoulder. I left my set of keys on the kitchen counter with a short note thanking Becky for letting me stay. With that I closed the door and headed to the bus stop.

Half hour later I walked through the school gates and I could see my old class mates gathering. Off to the side a TV crew was setting up their equipment. I saw Tom and we shared a distant smile. I reported in to the teacher in charge, I took her aside and explained the situation. I showed her my new ID so she could see I was not making a joke. She was perplexed but said OK, she asked me if I wanted my results separately away from the camera, I said I am not hiding from anyone, this was who I was. She gave me a genuine smile and told me good for me.

I reintroduced myself to my class mates, I was surprised they accepted me with open arms. A couple of the girls even hugged me. I could tell a couple of the boys were not happy about it, but they just kept their distance. I headed to toilet before my big moment on breakfast TV. I had a text from Becky wishing my luck and told me she and Chris were watching TV in bed waiting for me to come on. As I came out of the loo, I saw Tom walking down the corridor. He stopped and chatted, he told me he was proud of me and that I was the most beautiful girl here today. I blushed, and then had a wicked thought. I grabbed his hand and headed up the stairs to the top floor of the building.

I pulled him into one of the toilets and my mouth was on his, our tongues meet and danced. I rubbed his cock through is grey school trousers, I could feel it grow. I undid his trousers and let them fall to the floor. I used the soap dispenser above the sink to coat his cock with soap to make it slick. Flipping up my skirt I pulled my panties down whilst leaning over the sink, this was all the invitation he needed as he pushed his cock into me. My own cock was rock hard, and I looked at myself in the mirror as Tom slowly fucked me. As the soap transferred to my pussy walls the resistance was gone and he started to fuck me harder.

Tom reached under my skirt and found my cock and started to stroke it in time with his thrust. He leaned in and kissed the back of my neck as he increased his pace. I was moaning and panting as he was fucking me hard. With a cry he unloaded into me, this set me off as I came all over the floor. Tom pulled out and turned me around gave me a long kiss. With a regretful smile he wished we had hooked up earlier and what a lost opportunity it was.

I told him if he was ever in London, he could take me out on a proper date. He smiled but said nothing. In an awkward silence he pulled some paper towel from the wall unit and passed some to me. I wiped the cum from my arse as he cleaned his cock. We both redressed, and I had to straighten my tie and fix my lipstick.

As he was leaving, he stopped, kissed me behind my ear and told me it was a date, i smiled. After he was gone, I wiped my cum off the floor and checked myself in the mirror once again. When I was happy with my appearance, I headed downstairs for my TV debut.

I joined my fellow class mates and received our results, I was also interviewed on the TV, they did not suspect a thing. After the film crew left, we shared a few hugs and some laughs. The group started to break up and I gathered up my backpack and prepared to leave.

I put my headphones on and pressed play on my Walkman, I had a song cued up ready for this moment. The opening bars Forget about me by Simple Minds played into my ears. As I strolled out of the school gates that last time, I punched my hand into the air mirroring Judd Nelson from the Breakfast Club.

I caught the bus into town, brought a ticket in the train station for London. I had a light lunch in the station café and at the right time I boarded my train and left this town and my old life behind.

After an hour of traveling, I pushed my key in to my new front door. I flipped the light on loosened my tie and opened my collar, home at last. I had a bath and settled in for the night.

Over the next few days I organised my flat, visited a few charity shops to buy some much needed furniture.

I also managed to get a job as a waitress in a local restaurant, I had to wear a uniform, which I had to supply myself. This was not too much of an issue as is was a white shirt and black skirt, which I already had with a black tie.

I had my first appointment at the gender clinic, I was started on a medium strength hormone. I was given my surgery options; I would have to live as a woman fulltime for 12-months until I could qualify for a gender reassignment on the NHS. I could have other cosmetic work done as soon as I could afford it. For face and breast cosmetic surgery I would need to find £3000 to go private. I was earning £200 a week from my waitress job, I was reluctant to return to being a prostitute but my options were limited.

As I was on the tube heading home, I was flicking through the free paper and at the back I read through the classifieds. One ad caught my eye, it was for Escorts. The bulk of the add a was offering escorts, but at the bottom it listed that they had vacancies. I pulled out my mobile and dialled the number, I had a brief chat with the girl at the agency; they did cater for trans-girls. I setup an appointment the next day.

After I knocked off from my shift at the restaurant, I headed to the agency. I meet the owner; he was a little creepy. He had my take my coat off and stand in his office whilst he walked around me. I was still in my work clothes, white shirt, black skirt and black tie; tied in a perfect Winsor knot. As we chatted, he had his assistant take my measurements with a tape measure. Each client would pay £200 for my company for an evening, this was just to go on a date. I would get £75 of the fee after tax. He stressed that they were not here to pimp me out and if I came to an arrangement with the client for extra services, they did not want to know about it and I should consider it a tip.

The had me remove my tie and open my shirt, and pull out my ponytail and told to look sexy. After a couple of polaroid's, I signed an application form and that was it I was a registered tranny escort.

I went back to my life, and two day had passed before I received a call from the agency. I guy of 45 had requested my company for the evening. I got off work at the end of my shift and headed home. An hour later I was showered and in my little black dress with 3" heels. A short cab ride later I arrived at the meet spot. My client Simon was already there, he said my picture did not do my justice and that I was 100% passable.

We had our "date" and he was the perfect gentleman. As we left the restaurant and stood outside, there was an awkward where I felt he wanted to ask for more. He was an attractive man, but I was tired so it was up to him to ask. Just as I was about to say goodnight, my 3 hours was up. Simon final chirped up, he asked me if I could spend some extra time with him. He asked me how much for some extra private time. If he wanted the full girlfriend experience would cost him £200 for a couple of hours or £500 for the night. He went for the £200 option.

I thought we would be going back to his place, but it turns out he lives with his mother. So, here we were parked up in a dark industrial estate in the back of his car. He was clearly nervous, so I took the lead and kissed him. He started to relax, so I rubbed his cock through his slacks. He started to moan into my mouth as I stroked his cock. I was a little worried he was going to blow right there. I broke the kiss and opened his trousers, fishing out his cock. I bent over and took his small cock into my mouth. His reaction was clear that he did not have too much sexual experience, I suspected this could even be his first time.

I teased him for about 15 minutes bringing him to the brink and then backing off. I then brought him home and he fired into my mouth. He was sweet after thinking we were done and apologising for cumming so soon. I kissed him and told him we were not finished. I stroked his cock and balls, after a few minutes he started to harden again. When he was full hard again, I reached in to my clutch purse and retrieved my small tube of lube. I greased him and lifted my dress and pulled my panties to the side. I climbed over him and lowered myself onto his cock.

His cock was not that big, but it had been nearly a week since I was fucked in the bathroom at school. I rode him hard as I needed to get off. His face was like a deer in headlights as I rode him. I loosened his tie and opened his shirt. I knew I was going to fire my load over his chest. Lifting the form of my dress and pulled my cock out of my knickers. I was actual bigger than Simon and I was now fully erect.

As I pumped myself on his pole, I wanked myself off at the same time. When I came, I grunted and my arse clamped around his cock and Simon unloaded into me. I climb off of him and adjusted my clothes. Simon just sat there is stunned silence with my jism all over his belly, I asked him if he was OK; he turned and told me that was the best sex he had had.

Simon cleaned up and took me back to our meeting spot. He gave me my tip and when I got home, I stuffed my earnings from this evening into a jar. I wrote on the front of the jar "Tit fund".

I went back to the day job and my "date" with Simon quickly faded to the back of my memory. As I had my break, I checked my phone and had a text to call the agency.

I was asked if I would be free this evening for a stripper job, it paid £150 cash, I said I would be available. I was told I had to wear a particular outfit and the agency would sell me it for £60, but I could keep the outfit for future bookings. I reluctantly agreed and was told to show up at the office at 6pm.

After work I rushed home showered and put on some sexy undies and threw on a tracksuit over the top. When I got to the office, I was shown into the boss's room and he explained that I was to perform for a birthday party. He introduced me to a larger man in black jacket, his name was Phil and he was my security just in case things got out of hand. Phil smiled and told me I'll take care of you love. Candi the assistant took me off to a side office to get me kitted out.

10 minutes later I was dress in an authentic police uniform, black skirt, with white shirt, a checked cravat clipped to my collar and black tunic over the top. My hair was tied up into a bun and black policewoman's hat perched atop my head. I was surprised this was 100% real and not some fancy-dress outfit. Candi explained it was a surplus uniform, and they were actually cheaper than the fantasy outfits. She handed me a truncheon and a pair of handcuffs with the key. I put them in the long pockets of the skirt and headed back into the main office.

The boss took a couple of pics and told me I looked good in a uniform. I told him I also had a school and nurse uniform as well. He said if I brought them in he would take a few pics and add them to my profile.

Due to strict rules about impersonating a police officer I took off the hat, tunic and cravat, opening my collar and put my tracksuit top over my shirt. The boss slipped my £90 and told me to have fun.

I jumped into a white van with Phil and we droved to a pub about 15 minutes away. As we drove, we chatted and he told me that some girls can strip several times a night, not bad money.

Once we were are the pub, Phil popped inside to make sure they were ready. I put back on the rest of the uniform and waited. He came back after a few minutes and told me they were ready for me. He picked up a bag and opened it, inside was a blindfold, ropes and some whipped cream in a squirt can. He told me where the "victim" was sat, I was suddenly hit with nerves but Phil put a hand on my arm and told me it will be fine and just enjoy it. He gave me a quick briefing of what I needed to do and he would tell me if forgot something. I was to walk in and arrest the client. Once handcuffed, I was to strip search him. Then I was to dance for him whist I strip down to my underwear, they had not paid for a nude show. After I stripped, I was to release the client and let him squirt cream onto my and lick it off. I had 15 minutes to do all this.

I got out of the van and smoothed my skirt and tugged down on my tunic. Here goes nothing I said to myself and walked towards the pub.

As I entered the bar all eyes turned to me, there was a table to the left where some of the guys were struggling to conceal the surprise they arranged for their friend. I walked up to the client trying to look formal and official.

Are you Steve Wilson I asked him, the client had a look of fear on his face, I guess I look like a proper policewoman? He said he was so I had him stand and turn around as I "arrested" him, I'm not sure I read him his rights properly as I tried to remember back to watching episodes of The Bill. I accused him of having a concealed weapon and that I would have to strip search him.

His mates all burst out laughing and the game was given away. I stripped off his clothes leaving him in just his boxers, I got the ropes from Phil and tied the clients'chest and legs the chair. I looked to Phil, he nodded with a reassuring smile that I was doing alright. Phil pulled a small boombox from the bag and hit play. The sound of the Pretenders, I touch myself started to play, this was my cue to strip.

I started to dance whilst the first verse played, as the chorus approached, I put my hat on the client's head and released my hair letting it cascade down. I then slowly opened my tunic, I held it open as I rubbed my breasts into the client's face smothering him. I released him and slipped off my tunic. I got more sensual with my dance as I rubbed my hands over my tight shirt. I could a glimpse of Phil and he was making a wind it up signal.

I leaned into the client once more a put my cravat into his mouth, with a quick pull it snapped free from my collar. I quickly lost my skirt and as the song was coming to an end, I had my shirt open and I sat on the clients' lap. His mates all cheered, and I gave him a peck on the cheek and asked if he was OK, he nodded yes and the hard cock pushing into the gusset of my panties told me he enjoyed it. I gave my arse a little wiggle as I climbed off of him.

I release the client from the handcuffsand ropes, then i took the cream from Phil. I was now totally relaxed at this point and gave the cream to the client and told him he can spray this anywhere on my body and lick it off. He sprayed it across my chest and I grabbed his head and shoved it into my chest. He licked me clean and I lift his arm in victory and asked the pub to give him a round of applause for being a good sport. The roar with appreciation.

I gave him a hug and I picked up my clothes. The guy who booked the show had a quick whip round with his friends and they gave me a £60 tip.

I was led into a back room so I could redress. I just put my shirt and skirt back on.

Outside the pub the client was waiting there, he said he really enjoyed my show and wondered if he could hire me for a private performance. Phil was about to step in when I put an arm on Simon's shoulder and told him as was a T-girl, he said he did not care. I told him I was available as an escort through the agency, if he want to see me again he should make a booking and ask for Brenda, Phil handed him a card. And with that I got into the van and Phil drove me home. Phil said I was a natural.

Once in my flat and hit the shower, I had to have a wanked to relief my tension, Stripping was fun, but it leaves you horny.

I stuffed cash into my Tit fund and went to bed.

If you would like a pt 6 please comment and let me know.