The Path to Happiness Pt. 06

A few weeks passed since I moved to London, I had a few weeks before university. I had been kept busy with my waitress job, and the escort and stripping job was boosting my cosmetic surgery fund. The escort work, had led to a couple of shags, but for the most part my sex life had trailed right off.

One night I was working busting tables at the restaurant, there was a guy in an expensive looking 3-piece suit. He was dining alone, and was staying at the hotel next door. At the end of the evening he was the only one left and I brought him the Brandy he ordered. I was busy clearing and setting the tables for the next day, I could feel his eyes burning into me. He asked for the bill and he totalled up his meal and handed it to him. He paid cash, the handed me a £10 note, for my exceptional service. When my boss was not looking, he leaned into me and whispered there was another £90 if I fancied joining him in his room. He handed me a business card and, on the back, had written a room number on the back. With that he left.

I slipped the card into my breast pocket and finished up my duties as we closed the restaurant. I grabbed my coat and said my goodnights. I started to walk home, but I paused outside the hotel entrance. £100 will complete my fund, and I was horny, so I went in. I found the room number and knocked on the door. The door open and the guy let me in. He had removed his jacket, but still had the rest of his suit on. I was straight forward and told him that I was a T-girl. He said as long as I left here with a load of his cum in me, he did not care.

With that he opened his trousers and let them drop to the floor. I reached up to my tie, but he told me to leave it on. I sunk to my knees and swallowed him whole. I started to work his fairly sized cock; I had missed this feeling of a cock in my mouth. He moaning was so clearly enjoying, he called me a sissy bitch. He grabbed the side of my head and started to skull fuck me. He was getting a little rough and was letting me know he was in charge.

He pulled out of my mouth and reached down and grabbed my tie and used it to pull me to my feet. Using my tie as a lead he led me to the bed and pushed me down atop of it. He lifted my skirt and ripped my tights open. Grabbing the flimsy material of my panties he torn them open the back me exposing my arse. He started to finger my hole and use his spit to lube my hole. He was not wasting any time getting more fingers into me. My own cock had hardened fully, I really did need this fucking.

He pulled his hand out of me and replaced it with cock head. Like the blowjob he was after a quick fuck. He started slow, but was pounding me hard within a minute, and I was loving every minute of it. He slapped my arse calling me a tranny whore and fucked me faster. I turned around and told him to fuck the sissy whore harder spurred him on. I knew I was close and I did cum in the remains of my panties. He grunted and emptied his balls into my bowls. He pulled out of me and collapsed on the bed next to me. I laid next to him smoothing my skirt down, loosened my tie and opening my collar. He told me I was a good fuck but he was done with me.

I stood up and started to gather my things, he got up and took some money out of his wallet. He gave me £100, he told me the extra £10 was for the underwear he wrecked. As I was about to leave, he asked if I was free tomorrow night at 10pm, I said I might be. He told me to come back tomorrow night and wear something sexy. The walk home was interesting as there was a breeze up my skirt and chilling my stretched hole as the mans cum dripped down.

Back in my flat I stripped off; my tie knot was a little tricky as it was pulled impossibly tight. I hit the shower and went to bed.

The next day was a Saturday, so I had a lay in and enjoying the fact I now lived alone. My slumber was broken with my mobile ringing, it was the agency. If I was free, they had 4 stripper jobs lined up if I wanted. Two were as a policewoman and the other two were for outfits I did not have; nun and WRN (Woman Royal Navy). As usual they would generously sell me the outfits. They were late afternoon and early evening jobs so I could still meet my mystery man.

I got up and showered, ate breakfast and gathered my police uniform together into my stripping bag. I caught a bus over to the agency, picked up my money and new outfits. Phil was going to be my driver again and he would pick me up at 4pm to start the tour of jobs. First was the police uniform, then Nun, back to police and finish as a WRN. I had since my first job purchased myself a long overcoat to hide my outfit from prying eyes.

Back home I put on my sexy underwear and tried on the nun and WRN outfits, both fit perfectly. I then put on the police uniform, and they had lunch. I had a knock at the door and I answered it, it was a parcel of school books for my course. I did not really think when I open the door. The poor guy looked nervous as he handed the box to the policewoman. It was only after closing the door did, I realise what I just did, I just had to laugh.

4pm the door knocked again, it was Phil. I gathered up my outfits and we headed out. As we drove Phil briefed me on the client's requirements.

The first event was a stag do and it was a re-run of my first job. After that I put the habit over my undies and we headed off again. This was an interesting gig, no pretence just acting as a slutty nun. Back to the police uniform again and rehash of that routine.

The WRN uniform was not dissimilar to the police uniform, black skirt with a double-breasted tunic, on each cuff were gold stripes that I was told made me a lieutenant. White shirt and a black tie that was not a clip-on. I liked the tricorn hat that completed the outfit. I got a few wolf whistles as I walked back through the pub heading for the van.

Phil told this job was for a stag do but they were all sailors, it was bound to get boisterous.

Phil was right, they were very drunk and I had my arse pinched by more than one randy sailor. I felt sorry for the client, his cock was rock hard when I sat in his lap at the end. His mate slipped me £50 to show his friend a good time. Phil smiled and turned away. I quickly redressed back into my uniform, all to the cheers of crowd. I then took him by the hand and led him in to the gent's toilets. Once inside I sunk to me knees and pulled his boxers down. I licked my lips and devoured him into my mouth.

Bless him he was really horny, he did not last 30 seconds before he unloaded into my mouth. His legs went week at the knees, so I had to grabbed his buttocks to steady to steady him. I let him slip out of my mouth and stood up. I gave him a peak on the cheek as I pulled his boxers back up.

When we went back into the bar, I lifted his hand in victory and declared him "a very able seaman". Phil was waiting by the door, and we left together. In the van I slipped him £10 from my "tip" for turning the other way. I asked if he could drop me off at a hotel but to swing by my home first.

At home I stripped out of my navy uniform and put on my police uniform, without the cravat and hat. I slipped my over coat over the top and put the hat and cravat into a bag and went and jumped into the van with Phil.

He dropped me off and left. I headed up to the guys room, but in the lift I took off my coat, closed my collar and clipped on my cravat. In the mirror, I perched my hat on my head and stuffed my coat into my bag.

I stood outside his door knocked 3 times, as I waited I smoothed my skirt. He opened the door and was surprised to see a policewoman standing there. I told him he was under arrest for soliciting a rent boy. He did not recognise me until after I cuffed him and closed the door. It was when I pulled his trousers down he then put two and two together. He was helpless in the handcuffs so I forced him onto his back on the floor. I was feeling a little naughty and dominate, so I lifted my skirt and pulled my panties to the side and sat on his face draping balls into his mouth and told him to suck.

At first he squirmed, but after I pinched his nipples hard he opened his mouth and licked my balls. After several minutes I was rock hard, so I slipped my balls from his mouth and probed my cock head over his lips. Again he was reluctant to obey me, so I leaned over his body and sucked his cock into my mouth, as he moaned his mouth opened and I guided my cock passed his lips.

I blew him as I face fucked him, his resistance had disappeared. I took a bold step and let his cock out of my mouth and the pushed my tongue into his butt hole. As I ate him he was clearly enjoying the rimming. When he was wet I pushed fingers into his butt and started to stretch him, I made the decision that this guy was going to be fucked by this tranny policewoman.

When I felt he was ready I pulled my slick cock from his mouth. Still acting the tough bitch I rolled him over and using the cuffs forced him to his feet, I frog marched him into the bedroom and pushed over the bed. He tried to stand as I kicked his legs apart, he knew what was coming as tried to protest. I lifted my skirt and pushed my cock into him, he let out a yelp and I entered him.

I slow entered him until I bottomed out, he was squirming more than before. I slowly started to fucked him, and his half-hearted protested were not convincing me of his discomfort. I increased my pace, and his protests turned to a desire and he begged me to fuck him, so I did.

I fucked him for a good 5 minutes before I unloaded into him, I gave him 3 thick ropes of cum into his arse. I regained my composure and pulled out of him, and then released his handcuffed hands. I was a little fearful he would hit me, but he turned and flipped my hat off and kissed my deeply. I slowly stroked his cock, and whispered he had been a good boy and time for his reward.

I undid my skirt and let it fall to the floor, I climbed onto the bed rolled onto my back, and presented him my arse. He climb between my legs and penetrated me. He tenderly fucked me as he kissed me, he was making love to me, I had broken his dominate streak and he treated me as an equal.

I unbuttoned my tunic and opened my blouse leaving my cravat in place. We made love for a good 15 minutes before he filled me with his seed.

We cuddled for a while then I got out of the bed and cleaned myself up. I took off my cravat and tunic and put on my skirt and coat. The client counted out the money with a little bonus, he said he had never been dominated before and loved it. He was headed home tomorrow, but he was defiantly going to get fucked again.

I gave him a lingering kiss and told him so call me if he was ever back in town.

I caught a cab home and took a shower and hit the sack.

I had a lazy morning catching up on my sleep after couple of late nights. Around 11am my phone rang, it was the agency. They had a strange request for an escort. A guy wanted a private dinner with a young looking guy, he wanted the guy dressed in school uniform. I was about to decline when they told me it was £500 cash. I thought for a minute and accepted the assignment.

I found out my most masculine looking trousers and pair of black running shoes. I removed my beast forms and carefully peeled the lace front of my wig off. I tried to avoid seeing myself like this, it was a reminder of the life I left behind.

I hit the shower and put on a pair of white French cut panties, the closest thing I have to boy pants. Put on my blouse and black trousers. I had lunch and then put my tie, pullover and blazer. I hope the client would not notice the buttons were all on the girl's side.

I took a cab over to the address and knocked on the door. The door was opened by a guy not much older than me, he too was dressed as a school boy. He introduced himself as David, I told him my name was Simon; Brian never existed as far as I'm concerned. He led me into the living room and for the next hour we played video games and acted like a couple of ordinary boys.

Out of the blue he put his hand on my knee, he looked at me, I could see the nerves showing in his face. He smiled and said he liked me, I told him I liked him too.

He leaned over and kissed me, he quickly pulled away and turned his face away. I smiled and lifted my hand to his chin and turned his face toward towards mine and kissed. He melted into my arms as we embraced.

I stood and put my hand out and he took it. I led him to his bedroom, it was clear he was into scifi and comics as his bedroom was a geeks wet dream. We sat on the bed and kissed again, falling back onto the bed. I rubbed his crotch through his grey trousers and felt him grow. I broke the kiss and asked him if this was his first time, he would not meet my gaze and said yes. I slipped my hand into his blazer and cupped his flat breast and found his nipple. Nibbling his ear I asked his he was a top or bottom. He said he did not know, and wanted to try both. He said he had a thing for school uniforms and had fantasied of having sex with the boys he had been to school with, He assure me he was over 18. He also wanted us to stay as dressed as possible, It was him money so I agreed.

I opened his trousers and pulled out his cock, he was cut like me. Kissing the head it was heavily leaking precum. Deep throating him I sniffed his pubes, this was how I had imagined my first time being before we were busted by my dad.

By now I was an expert cock sucker and knew how to keep a guy from busting his nut too quickly, but this guy was a real struggle from cumming to soon. I sucked on his balls and licked his arsehole, he was clearly into it and any illusion he may have had about not being gay was gone.

I pulled off of him and told him it was his turn, he started at me blankly so I grabbed his hand and put it on my dick. He snapped out of his daze and he opened my slacks and pulled out my cock. He stroked it for a bit before licking my head. I laughed and told his it did not bite.

He certainly did bite so I told him to go easy with his teeth on my dick. He soon got the hang of it and was giving me a half decent blow job. I pulled him off me and arranged us in a 69 position and told him to do what I did. I went back to blowing him and alternated by sucking his balls. He was a quick learning.

Pushing him, I started to rim his arse and he was attempting to do the same to me. He had a nice cock but I was starting to think David was defiantly a submissive bottom.

This was confirmed when he asked me to fuck him, I was defiantly a sissy bottom myself, but if fucking his arse pays for my breast surgery then lube up son I'm coming in. He squirmed as I pushed passed his rectum, and kept pushing until I was all the way in. He had tears in his eyes so I kissed the back of his neck and called him a sexy schoolboy and he arse was ripe for cock. I was getting good at pleasing my clients.

When he had relaxed enough I started to pump in and out of him. He screamed like a girl as I was taking his cherry. Screams of delight, and I was at the point where I wanted to cum. Disregarding his comfort I fucked him mercilessly, he did not seem to mind though and pushed back to meet my strokes.

After a couple of minutes I grunted and unloaded into him. I reached around and stroked his rock hard cock until he came too.

We collapsed onto the bed exhausted. We lay there for a while and chatted.

He was a closet gay, and always too scared to act on his feelings. He was in his second year of university and had won £500 on a scratch card so ordered and escort to play with.

I filled him in on my story, he was surprised I was actually a transgender woman.

I could see his cock was stirring so I kissed him and told it was his turn to fuck me.

I had him rim me for a couple of minutes to get me ready, then fed me his cock. I laid on my back so he could see me as he fucked me. Since he had cum already he lasted a good 20 minutes before he came in me.

I asked him if I could use his shower, he said yes. I told him to join me, we peeled each other's clothes off as we kissed.

In the shower we kissed and he gave me another blowjob, he loved the taste of cum. He confirmed that he preferred to be the one fucked rather than the one doing the fucking.

I dressed and he gave me my fee. We exchanged numbers, I told him that we would only be friends and I was happy to support him finding a boyfriend. The next time we would meet I told him he would be meeting Brenda.

We hugged and I left.

Once home I stripped and put my breasts and wig back, and choose a silk nightie. My tit fund was complete and I had plenty of spare cash left over.