The Path to Happiness Pt. 04

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My future was as a woman was coming together.
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Part 4 of the 13 part series

Updated 06/09/2023
Created 08/27/2019
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After couple of days I had settled in to Roger's spare room. I cleaned and cooked for my room and board, not that I was a great cook, but I could warm up food without burning it.

I was living full time as Brenda now. My last outing as Brian came when I went to my Store job and quit. I had only worked there a few weeks but the manager wished me well when I told her I was leaving town. On my way home I stopped off and got my ears pierced, it hurt like hell, but at least it would help my female appearance.

I picked up a form from the townhall, to formally change my name. When I got home, I changed into Brenda and started dinner. Roger came home and I handed him a glass of wine as we sat down to dinner. After dinner Roger, changed into Becky and we sat watching TV for the rest of the evening.

Becky signed my depool form to changed my name legally, I choose Brenda Georgina Chaplin as my new name. Around 10.30pm we adjourned to our separate rooms and called it a night.

The next day I introduced Brenda to my brother John, he was a little taken back but was cool with having a little sister. That afternoon I went back to the townhall and walked out with a new birth certificate in my new name. This felt like the first major step to leaving my old life behind. The next step would be to get my gender status changed.

I stopped by the bank and formally changed my bank account details to my new name. The older lady who served me held little back with the disgust in her face about my life choice, she held a veil professional curtesy.

At 6pm I was to meet Doug at his doctor's office. The receptionist let me in as she left and walk down the corridor and paused outside the door with his name on. I gave it a knock and he invited me in. Doug was in his mid-50's, bald with a ring of white hair encircling his head. He was dressed in his doctor's coat, with a pale blue shirt and yellow tie with red poker dots.

I sat and we went over the letter, it was perfect, it had my official diagnosis as a transgender woman. He had already sent a copy to the university administration, and gave me two copies. I told him I could never repay him, he winked and said the agreed fee was awaiting me in the examination room, he told me to go through and get ready and he would join me in a few minutes.

Stepped through the dividing door in to the examination room. Laid out on the bed was a nurse's uniform. I stripped down to bra and panties and slipped the white stocking up each leg. The dress was white as well with dark blue trim around the collar and short sleeves. I click all the poppers up and passed the blue belt around my waist and fastened it. The white 6-inch stilettos were clearly not regulation but they fit perfectly. I pulled my hair into a bun and placed the white nurse's cap on my atop my head.

I perched myself on the edge of the bed, crossed my legs lifting the dress to show a little stocking top. I leaned back on the bed trying to strike a sexy pose.

Doug entered; he was still in his doctor's coat but I noticed his legs were naked. "Nurse Chaplin, I've heard you have been giving the patience a little extra service", he said. I put a coy look on my face, "what, me Doctor?" I replied trying to look innocent. He placed a hand on my knee, "Do you extent this extra care to doctors"?

I reached out and rubbed his cock through his coat, I could tell he had on no underwear either. I slipped of the bed and onto my knees, I reached up and opened the bottom four buttons of his coat and as I parted it, I was greeted with the sight of his semi hard cock. I took him in hand and smiled at him, of course Doctor, as I sunk his cock into my mouth.

I stoked his balls as I work his cock with my mouth, he purred with pleasure. I did not want him to blow so early so I let his cock flop out of my mouth and stood up. "Doctor I have this pain, can you please check it out", I said as I climbed onto the bed presenting my arse to Doug. Doug lifted my dress and pulled my panties down. He squirted some lube on his finger and slipped it into my hole. Doug found my prostate and messaged it. My own cock stain so hard I though it would explode. He worked several more fingers into me before he pulled out. "Now I need to take your temperature", he said.

Doug slipped his cock into me slapping my arse as he went in. He waisted no time fucking me, he was clearly not up for a long sensual love making. The last time we met he had me in my schoolboy uniform and he was rough and quick then as well. He was rough, and called me a sissy whore, slapped my arse and he pounded me. He was a bit of a sadist, and had no interested in my pleasure. I was just a play thing to him, and he treated me as such. With a grunt he fired into my boy pussy.

He wiped his cock on my arse cheek, as he pulled out of me. I was a little sore but nothing I could not handle. He helped me to my feet, and was friendly again.

He told me I could keep the outfit, and left to go back to his office. I decided to just pull up my panties and stuff my other clothes into my backpack.

We said our goodbyes and I headed back to the apartment. Becky was already waiting for me when I got home. She was amused at my attire. I took a shower and jerked off, and then dressed in my night clothes. Becky and I settled in for the evening.

The next couple of weeks flew by, Becky and I became very close friends. She had gone out with Chris a couple of times, she even stayed over one weekend. She was starting to get bolder in public and started to come and go from her flat as Becky. Roger only came out when she went to work.

Work wise I had a steady stream of clients, and my bank balance was looking pretty healthy. I paid my tuition fees upfront for my law course. I had also started to look for a flat in London, I quickly came to the conclusion that I was only a few thousand pounds shy of being able to buy a small flat. This seemed to make more sense than renting.

I took a few trips to London and I found a flat that was a fair size for a single lady, though it would need my personal touch. I also made an important business decision and brought myself a pay as you go mobile phone.

After I emptied my bank account (I had a couple of thousand left) and signed for my flat; Becky and I went out on the town to celebrate. We were dancing to the latest tunes on the dancefloor when I noticed across the club a familiar face. It was Tom, the guy I was blowing when my journey began.

When he was alone at the bar, I decided to stand beside him, we made eye contact and shared a smile. I laughed inside; he did not recognise me. I took the bold step and told him that he knew me. He looked puzzled.

We grab a drink and headed in to the corridor the led to the toilets so we could talk. I re-introduced myself as Brenda, but he knew me as Brian. The penny dropped, and he looked at my again and he finally had a look of recognition on his face, with a little shock.

I could not help but laugh, he apologised for running away when we were caught; I told him it was no problem he had actually done me a favour. He told me he could not believe I was a guy under the sexy girl standing before him. We started to flirt a bit and even went back to the dancefloor for a dance.

When Tom went to get me a drink, I explained to Becky who Tom was. Becky could tell I liked Tom, she told me that I was free to take him back to her flat if I wanted to.

The DJ started to play the slow dance music, and Tom moved in and held me. We swayed to the music and Tom leaned in and kissed me. I melted in his arms. My mind was made up, I leaned into his ear and told him we should go back to my place and finish what we started. He smiled and we left the dancefloor, Becky gave me an assured nod as we gathered my stuff to leave. Becky had made friends with a couple of other girls so she was fine.

We grabbed a cab back the flat, and once inside we were all over each other. Within minutes we were naked in my bed, and his cock in my mouth. I was deeply enjoying his cock back in my mouth, this time we had all night to fuck. I had by this time had a few cocks in my mouth, but this was the first I had taken one for passion. I savoured the taste as I took it into the back of throat. Tom had a hand on my head as I deep throated him. Let his cock drop from my mouth as I took his balls into my mouth.

My hand worked his shaft as I alternated between his bollocks. I even licked his arse which made him squill like a girl. He pulled me up to face him as he kissed me with a passion I had never experienced before. I whispered into his ear that I needed him in me. He kissed down my back until he reached my butt, he parted my cheeks as kissed my hole. After a few minutes he rolled me onto my back and lifted my legs over his shoulders. He gently pushed his head into me. I purred with delight, I had waited months to have Tom's cock in me and it was finally happening. He started slow and sensual as he made love to me, he bent over and kissed as a lover; not a whore.

As Tom pumped in and out of me, I felt complete, He was my man and I his sissy girl. He was in no rush as he made love to me, but I felt my climax build as I fired my load between us. Tom increased his pace and with a couple of hard thrusts unloaded into me. He slowly withdrew from my and spoon cuddled me as we drifted off to sleep.

Tom woke me later and told me he had to leave, He told me that last night was special; but we could never be together properly as a couple. I kissed him and rest assured him that I liked him, but I was not sticking around long enough to get into a relationship. With a glint in my eye I took him into my mouth and sucked him hard and fast. Within seconds he was fully hard, I pulled off of him a pushed him onto the bed and straddled him. Slowly I impaled myself on his rod and started to ride him. He did not complain as I fucked myself on, his cock. I was not slow or sensual, I wanted his cum in me. He did not last as he grunted and dumped another load into me.

I climbed off of him and stuffed his cock back into his trousers. I scribbled my mobile number on a scrap bit of paper, and told him if he was ever in London to look me up. He gave me a long hard kiss and was gone. I crawled back under my covers and went back to sleep.

I had a lazy day and stayed in my night gown; Becky was home, she had met some nice girls who had accepted her for being not 100% a woman. It was good to know Becky would not descend back into the closet when I left.

I meet up with my brother the following day, again he had my post saved before my father could destroy it. There was a letter from my school, it was an invite to pick up my exam results. It would be on Friday at 8am, it requested us to wear our uniforms as there would be a television crew there to report on our results. Great, I'd have to buy another one, Becky had left my old one at Chris's.

During the week I serviced some clients but mainly I made my preparations for my departure. I also visited my flat and most of my stuff was now there, I did not have much stuff; but with the exception of the clothes I would need to see the week out everything was in my flat.

I purchased a new school uniform on the Wednesday, this time I brought the full girl's uniform. I giggled inside at the thought of the controversy I was about to cause when I picked up my exam results. When I got home, Becky was home and had made dinner. I showed her what I had in my bags and she got an evil glint in her eye. She told me that she was going to Chris's flat tomorrow for some schoolgirl fun. She asked me if I fancied joining them for one last time. I figured how good Becky and Chris had been to my I figured why not.

I had a lazy morning the next day, and Roger came home at lunchtime. He went off to his room as I made lunch. 20 minutes later Becky joined me for lunch. Becky told me that she had not told Chris that I was joining them and it will be a surprise.

I told her that after I picked up my results in the morning, I would be going straight to the station and leaving town for good. After lunch I dressed in a tank top and skirt and grabbed my uniform, and then we headed off to Chris's.

Chris had given Becky a key, so we let ourselves in. Chris would not be here for an hour, so we took our time to get ready. I hit the shower and gave myself a good wash, Chris had a douche in the shower which I made good use off.

As I left the bathroom Becky was in her school skirt, blouse and her tie was tied but her top button was open so it hung low. She handed me a glass of wine and I sipped it as I did my makeup. I dressed in my uniform, and tied my tie into a full Winsor knot.

Becky had also closed her closed her collar, straightened her tie and added her pullover and blazer; we were ready for Chris.

We were sat drinking another glass of wine when Chris arrived, he was pleasantly surprised to see two sissy schoolgirls awaiting him. "Hello sir", Becky said, "Miss Granger sent us to see you". "Did she now, why?" Chris replied.

Becky placed a hand on my knee and smiled, "she caught us fooling around". "I think you had better show me" Chris said with a glint in his eye. Becky turned to me and lean in for a kiss. Our mouths opened and out tongues danced with each other. Her had slipped up my thigh and under my skirt.

Chris ordered us to stop and stand. Playing along we obeyed and looked to the floor as a pair of forlorn schoolgirls. Chris had us follow him into his bedroom, and stand at the bottom of the bed. He scowled us saying this gay behaviour was unacceptable, and he would put us back on the straight and narrow. He ordered us to strip him, Becky started with his belt as I broke his tie and opening his shirt. In less than a minute he was naked and sporting a semi.

I joined Becky on her knees taking Chris's cock in to her hand. She looked up and smiled, "We love cock too sir", and with that she swallowed his cock all the way to the back of her throat. I took his balls into my mouth and rolled them around with my tongue.

Chris closed his eyes and moaned. Becky and I had decided earlier that we would take control of this game. We pulled off of Chris and crawled onto the bed.

Again, we embraced and made out, after a minute or so I turned around and we lifted each other grey skirts. I pulled her panties down and licked her limp clit into my mouth, she did the same to me. I grew in his mouth, where she stayed limp, I kissed my way passed his balls and to his arse; again, Becky mirrored me. Chris stood there stroking is cock watching the two prim and proper sissy schoolgirls eating each other's arses. We worked our fingers into each other stretching our holes ready for Chris.

I climbed off of Becky, and I laid on my back and lifted my legs inviting Chris to enter me. Without a word he was between my thighs and feeding his cock into me. I turned to Becky and sucked her tongue into my mouth. Chris was a man possessed as he pounded me, he was grunting as he worked his cock in my sissy pussy. Becky pined that she needs to be fucked too. Chris pulled out of me and mounted her.

Chris alternated between Becky and I, as we stayed in character. Chris was deep within me when his cock went off and he flooded me with his seed. We collapsed onto the bed and had a good laugh.

Chris threw a robe on and we adjourned to the living room and Becky opened a bottle of wine. Chris invited me to stay for dinner, but I declined as I had an early start in the morning. We chatted like old friends, even though two of us were dressed as schoolgirls and one in a robe. Becky was planning on staying the night so we said our goodbyes before I grabbed a cab back to Becky's flat. There were a few tears as Becky and I embraced as I left with promises to stay in touch.

The cab driver gave me a strange look as a schoolgirl with smeared makeup climb into the back of the car. At this point I really did not care, in 24 hours I would be long gone from this town.

Once inside the flat I stripped off and had a long soak in the bath. I dressed in my night gown and had a light dinner. Before bed I packed the a last of my stuff into my backpack and turned in for the night.

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