The Path to Happiness Pt. 02

Chris picked up his car keys and lead me out the door with my arm in his. He was taking me out for dinner.

I felt like Julia Roberts from Pretty Woman.

Chris to took me out for a lovely dinner at a 5-star restaurant, no one paid me any attention other than a few men eyeing me up. We drank Champaign, ate Michelin star food.

He drove back us back to his apartment and poured us some brandy’s. As we sat on a sofa, he placed a hand on my stockinged knee. He looked me in the eyes and told me I was beautiful, he leaned in and kissed me. He broke our kiss and reached behind the sofa and pulled out a white box. I lifted the lid and pulled back the crate paper to reveal a black pure silk nightgown. He asked me to wear, so I stood and took the box into the bathroom.

I removed my dress, stockings and underwear. The breast forms remained stuck to my chest securely. I took the night gown and slipped it over my head and let it cascade down my body, it fit me like a glove. I really love the fill of silk on my body. I fluffed out my hair.

I opened the bathroom door, and stood in the doorway. Chris was stripped off and, in the bed, I smiled and walked seductively towards him. He pulled the sheet back, and I slipped in next to him. As he pulled the sheet over me, he took me into his arm and kissed me. The kisses grew in passion as his hands roamed my body, I was getting very turned on. I broke the embrace and slid down the bed and took his cock into my mouth. He was half hard but soon hardened within my hot mouth. Chris was moaning with pleasure as I bobbed up and down on his cock greedily licking the pre-cum from the end.

I pulled off his cock and turned around on my hands and knees presenting my arse to Chris. He took the invite as he crawled up behind me and flipped the nighty up exposing my boy pussy. He leaned forward and dove his tongue deep into my hole an ate me out. The feeling was magical as he rubbed my balls as his mouth explored my rosebud. He started to add fingers with his tongue to my hole, opening my up. I turned back to him and told him in my most girlie voice to fuck me already. Chris slapped my arse cheek, which after our earlier fun was still very sore stung like hell.

I was soon distracted from my sore cheek as Chris’s cock entered me. I loved the feeling as it filled me up, I knew I was a cock whore. He started thrust in and out of me, Chris was grunting with each thrust. I caught a glimpse of myself in a mirror, I looked like a real woman being pounded from behind. The woman staring back at me called to me, I knew from this night on I would embrace her.

Chris was working up a good sweat as he fucked me, it felt great but all too soon his shot his load into me. He pulled out and fell on the bed beside me panting, I was worried he would have a heart attack. He soon regained his composure and slipped a hand under my night gown and started to rub my cock. He pumped my boy clit fast and hard; I knew I would not last long. Chris pulled up my gown exposing my cock, balls and chest. With a scream I exploded over my chest.

As I came down from my orgasm, Chris grabbed a tissue and wiped my cum off my chest and tossed it a side. We crawled back under the sheets and we spooned as we fell to sleep.

I awoke in the morning and I was alone in bed, Chris was nowhere to be seen. I sat up in bed as Chris walked in fully dressed in a suit carrying a cup of coffee. He handed me the coffee and told me he really enjoyed last night. I told him I enjoyed it too and hoped we could do it again sometime, he winked and asked for a discount next time. I laughed and said that could be arranged. Chris told me I could keep all the extra stuff he gave me from last night, I was a little disappointed when I learned the jewellery, he gave me was only costume jewellery.

I took a shower, but afterwards I was not ready to go back to being Brian just yet; so I put the breast forms, gaff and wig back on and made up my face. I slipped on a t-shirt and school skirt, I laughed and thought I really need to expand my feminine wardrobe.

Chris had made me some breakfast, and then drove me back to where he picked me up. As soon as we pulled up and I started gathering my new belongings, he slipped me an envelope with cash in it. He told me he slipped a small bonus into it. I leaned over and kissed him on the cheek and thanked him. I got out of the car and Chris was gone.

I walked back to my squat, and counted my money. Chris gave £10,500, I took £500 out of the pile and put it in my wallet. I headed into town and deposited the £10,000 into my account, then went on a shopping spree with the £500. A few hours later I was back home and put my new purchases away, I had a full wardrobe of female clothing. I also splashed out on a Walkman and a selection of my favourite albums. I chilled out for the rest of the day and changed back into my nightie at bedtime.

I dressed in my boy clothes the next morning and met my older brother for lunch. I told him I was working but spared him the details. He told me that my younger brother was dating an Asian girl from school, my bigot of a father nearly had a heart attack. Even though he disapproved, my dad had not thrown him out yet thought he was only 15 years old. John also gave me my post, he manged to intercept it before my folks did.

I had a coffee at a local café near my squat and read my mail, I had been accepted into St Marys college in London to study law. Tuition would cost me £45,000 for the 2-year course, so I knew my £13,000 would not be enough.

My luck was in as Chris had several like-minded friends and over the next two weeks I went on several “dates” with these older gentlemen. Mostly it was dinner and fuck, a couple had me dress as a schoolgirl and one had me dressed as a schoolboy. I had to admit I was preferring sex more as Brenda than Brian. My college fund had grown and I now had more than enough for my future education, I was not planning on being a T-girl hooker all my life even if the money was good.

Just over two weeks after my night with Chris I was waiting at my phone box waiting see if anyone call for my services. The phone rang and there was a new voice on the phone. He said he name was Roger and he needed a date for wedding, he got my name from Chris and wanted to audition me first if I was available for dinner that night. I agreed to the “date” and arranged to meet at the restaurant.

I took a cold shower and started to doll myself up for Roger. I wore my Greek style dress, virgin white with gold trim. I topped in off with 4” white heels. I stuffed some cash into my clutch purse and head to the meet. I called a cab form my call box and was dropped off outside the restaurant. The maître d, showed me to the table and Roger was sat waiting for me.

Roger surprised me; he was in his late 30’s much younger than Chris’s other friends. He wore an immaculate 3-piece suit, I could tell it was tailored from the cut as he stood to greet me. He kissed me on each cheek before we sat. We had a pleasant dinner and we talked about our lives and interests, he really felt like a date. As we drank coffee Roger told me I had passed the audition and if I was willing to accompany him to a friend’s wedding the coming weekend. I was to pose as his girlfriend and he would pay me £20,000 for the 3 day we would be away. He also explained that a childhood accident had left him impotent so he would not be fucking me, to say I was a little disappointed inside was an understatement. He did have sexual tastes and he would use my body to satisfy his needs.

He then paid the bill and slipped me an envelope with some cash and background to learn of the history of our “relationship”.

After I got home, I felt uptight. I had expected my audition to include a good fuck. I changed into my night clothes and wanked myself off dreaming of a cock up my arse. I thought I needed to buy so toys for my solo play time.

The next day dressed in my boy clothes I informed work I would not be in that weekend; I then brought a suitcase with my staff discount. As I strolled back to my room, I stopped off at a phone box and called St Marys college. I did not give my name and asked them about their transgender policy. The lady said they are an all-inclusive college and if I wanted to be admitted as a trans person I would need to be interviewed. I took a plunge and arrange a meeting the following day. They asked me my name and I said Brenda Chaplin, I decided I wanted nothing to do with my parents so I took a new surname to go with the new me.

The next day I dressed as formal as I could in a black pencil skirt, my school blouse and a tan blazer. I could a train to London and tube to the college. I was nerves as I was led into the admissions office. The head of admissions and the director of public affairs grilled me for an hour about my transgender status. I lied and said I should have been born in a girl’s body and I felt I could no longer live as a man. They were a little put off that I had not started any legal proceedings to have my gender changed. I explained that due to my situation at home was difficult since my parents disowned me, who would have thought I could cry on command. I told them that I would be changing my name prior to the start of the college year and would be living full time.

They told me I would be accepted as a female student if I had a doctor’s letter declaring my transgender status. I had no idea how I would get one, but I agreed to their demand.

I had lunch locally and headed back home. On the train home I hatched a plan, Douglas, or Doug; one of my clients was a doctor. I would ask him to write me a referral and I would give him a freebie.

When I got off the train, I hit the nearest phone box and called his private line. He was happy to help, but did ask me to dress up as a nurse; it was the least I could do. He would also refer me to the transgender clinic in Hammersmith, London. We arranged to meet up the Tuesday after my weekend away with Roger.

I brought a frock for the wedding and had my nails done, I just loved how girls are pampered. In the later afternoon Roger picked me up in his two-seater sports car.

We chatted casually on the one, I mentioned that I was going to live full time as a woman. Roger was very supportive; he was a therapist by trade and he gave me a mini therapy session right there in the car.

We arrived at a lovely country manor hotel, and we checked in and shown to our room. There was a large king-size four poster bed. We dressed for dinner, and we had a glass of wine whilst he quizzed me on our past.

Arm in arm we headed down to the dinning room, and I was introduced to his friends. I was surprised to see Chris there, I had to pretend to meet him for the first time even though he had been balls deep in me. He was accompanied by an elegant lady would was introduced as Silvia, his wife. I was supposed to me playing a 25-year-old, and I was working as a PA in the backing sector. Roger chose this occupation for me as none of his friends worked in Banking so they would not be able to grill me to deeply.

I was equally surprised to learn the bride was Chris’s daughter Alison. We had a pleasant dinner and after drinks we retired to our rooms. Roger congratulated me on my performance. He let me use the bathroom first, and I slipped into a slinky nightie. I was just getting comfortable in the bed when Roger came out of the bathroom. He was wearing a short silk nightie with black stockings. He had breast forms and a wig on, with some light makeup. He flipped off the main light and slipped into the bed next to me. He told me that when dressed like this she was called Becky.

I was still stunned as Becky rubbed a hand up my arm and leaned into kiss me. We fell into an embrace, as we explored each other’s mouths. She broke the kiss and told me she was a sissy lesbian, and only slept with other T-girls. I told her this was a new one for me but I’m up for some sissy lesbian fun. She smiled and kissed me again, she reached under nightie and stroked my cock. This was magnificent as my boy clit rub the inside of my silk nightgown, I moaned into her mouth. Beck broke the kiss and flipped me over and lifted mu butt off the bed.

She lifted my gown and leaned in and licked my pussy. She pushed her tongue into me and ate me, I purred into the pillow. She slipped a finger past her tongue and found my prostate. She increased pace and brought me to the bring of orgasm and then stopped. She stood up and told me to stay still. I could not see her as she disappeared in to the shadows of the room.

A moment later she climbed back onto the bed and I felt something hard rubbing my butt crack. The object pushed past my sphincter, and slow slid into me. I felt a surge of pain as I never had anything with such girth up my pussy today. Becky let out a little moan, as I looked over my shoulder. She was balls deep in my and I noticed some leather straps around her thighs. She slowly started to fuck me with abundance, and was clearly enjoying the feeling of fucking me. I had to admit once my arse stretched to accommodate the thick invader, I too was in ecstasy. She fucked me for a good 10 minutes, until I shot my load.

Becky pulled out of me and I could see she had a rubber cage over her cock. She explained that she was unable to get hard and the cage helped her fuck her girlfriends. I cleaned up my load as Becky removed her cage, she was leaking pre-cum. She told me that though it felt great she still could not cum as she fucked. She then flipped over and presented me with her arse, another first for me but I had come this far. I took up my position behind her and licked her hole, I closed my eyes and pushed my tongue into her. From her moans I was doing something right.

After a minute or so she told me to use my fingers, so one at a time I slipped three fingers into her. I thought she was about to lose her shit as I finger fucked her. She reached between her legs and grabbed my cock through my gown and started to stroke it back to life. After a few moments I had grown to full mast and Becky told me to fuck her. I had a moments hesitation, after all I was clearly a bottom. But Becky reminded me she was paying me well, fair point. I lifted my gown and lined up with Becky’s boy pussy and pushed. There was some resistance at first but all to soon her arse opened up to invite me in.

I slid into her until I bottomed out, I have a modest 5 and half inches and clearly enough to satisfy Becky. I started to fuck her slowly, and it did feel good. Becky ordered me to fuck her harder, her wish was my command. It dawned on me that she made me cum first so I would last longer when I fucked her. Well that worked as I fucked her for a good 8 minutes until I shot my load into her.

I pulled out and took my place beside her in bed. I’m not going to lie; I did enjoy fucking Becky; but I preferred to be the one being who was fucked.

She told me I was great, kissed me and turned over to sleep. I laid a wake for a little long think about what else the weekend had instore.