The Path to Happiness Pt. 09

A couple of months passed since my weekend away on the film shoot. I wish I could say Chris and I become an item, but sadly I discovered he was already in a relationship with a girl and she was expecting his baby. My life already had too many complications without becoming the "other woman".

On a positive note David had started a relationship with Adam, and they made a cute couple. I had dinner with then a few times, but I was mostly concentrating on my law classes, waitress job and enjoying the quieter pace of life since I became Brenda.

The only downside is 3 weeks ago Sylvia, Chris my first client's wife had lost her battle with Cancer, so I had to attend her funeral. It was heat breaking to see Chris, a clearly broken man weep over his wife's grave. Becky attended as Roger and I escorted him and we remained in the background. Becky and Chris had become very close, and now Sylvia had passed away, they were free to take their relationship to the next level. Both Sylvia and their daughter Alison had given their approval for the couple to become more official after her passing. We shared a nice moment at the wake where Alison actually comforted Roger, and assured her that Becky would be welcomed into the family if and when she was ready.

Whilst I was back in my home town I caught up with my brother and mother, my dad was easing off his hatred of my lifestyle choices and was pleased that I had come through being forced out of the family home and was making something of my life. Mum joked that at this rate he might accept his new daughter in 10 to 20 years.

I also met up with Tom, he was now engaged to the daughter of his Father's friend. This was setup for him by his family and his future was assure as long as he stayed the dutiful trophy doctor husband. He actual had feelings for his bride to be, and said the sex was not so bad, but not as good as it was with me. We did sleep together but alas this would be our last time together since Tom moved away shortly after he was wed.

I still kept up my appointments at the gender clinic, the hormones were doing their job and I was now 7 months way from qualifying for a full gender reassignment. A week after Sylvia's funeral Becky booked herself in for the first phase surgeries.

Between buying a flat, paying my tuition for my classes and the surgery I had already done, my savings were depleted. My outgoings were small and my waitress job kept me afloat, but I felt I needed some more money in the bank for a rainy day.

I called Tony at the studio and asked if there were any tranny movies in the works. He told me he had no live action films in the works, but had a request from a photographer who saw my first film and asked if I would pose for some photos for a tranny website. Why not I needed the money so I accepted and told Tony to pass on my number.

That night at work I saw the business man I had fucked a couple of time was in for dinner. He was not sat in my section and I could tell he was flirting with Cindy the other waitress. Oh well guess I will not be earning an extra tip tonight. He left around 10 and Cindy told me he had propositioned her, and showed me his card. I noted the room number before she ripped it up. I finished my shift and left work, I paused outside the hotel and thought if I should go in. I headed in and called the lift.

Once inside the lift I removed my tie, and opened my shirt to show my cleavage off. I knocked on his door and struck a sexy pose. The door opened and for a second, he looked at me confused. I said that Cindy could not make it, so I came in her place. I pushed passed him. It was clear he did not recognise me since my surgery, and my feminised face. I grabbed his tie and pulled him to me and whispered in his ear, that £50 for a blowjob and £100 for my arse. I rubbed his hardening cock through his suit trousers, and I could see in his eye he was mine.

He picked me up and threw me forcibly onto his bed, and then said with recognition that I was the tranny bitch that fucked him. I licked my lips and told him I was, as he approached the bed slowly stripping. I removed my skirt and unbuttoned my shirt revealing my tits. He squirted so lube on his finger and worked it into my arse. He said he approved of my improvements and started to lick my nipples. Soon he had three fingers in me and my nipples were rock hard.

He replaced his fingers with his cock and roughly forced his way in until he was balls deep. As he started to hump me, he placed a hand around my throat and gently squeezed, hard but I could still breath. I was disappointed as I knew he would not last too long and within 2 minutes he was grunting as he unloaded within me. He pulled out of me and slumped onto the bed next to me, my own cock was stand high and proud desperate for release.

When he caught his breath, he saw my cock and to my surprise wrapped his lips around it and started to blow me. As he worked my cock with his mouth, he started finger fuck my pussy. I played with my tits as he started to get my cock into the back of his throat. Spurred on by the sight of the big powerful business man sucking my sissy cock, I stared to call him a big sissy and to work that tranny cock. He was clearly still a cock sucking novice, but he was doing a great job.

I felt the tightening of my balls as I thrust my hips into his face as I unloaded into his mouth. After 3 spurts of cum I was spent, as the man dropped my cock from his mouth. He opened his mouth and showed me he had swallowed my load. I stripped of the reset of my clothes and jumped into his shower and cleaned his cum out of my arse. I re-entered his bedroom and the business man was sat on his bed wearing a robe. I started to dress as he pulled out £150 from his wallet and handed it to me.

He told me in a couple of weeks he had to go to New York for a few days for a series of meetings, would I be interested in going with him as his PA. It would be a 3-day trip and I would get £1500 for my time. He took out his card and told me to call him within 3 days if I was willing to go.

I headed home and went to bed.

After classes the next day, I headed to the passport office and looked at how to get my passport changed to my new name. 2 hours and £200 later, and I walked out with my new passport. On the bus home I called Richard, the business man and accepted his offer of the trip to New York. I texted him my passport details.

That evening I had a long chat with Becky, she was planning on moving in with Chris. We planned a girly night out before her first phase surgery. The reset of the week was quiet with classes and waitressing. Richard emailed me the literary for New York, so I arranged the time off work.

A few days later I received a call from a photographer called Sally, she got my number from Tony. She wanted to do an erotic photoshoot of me in my schoolgirl uniform, we chatted a bit and I agreed on £300 fee, for 3 hours work. We checked our schedules and I manged to fit her in before I left for New York.

Friday came around and I caught a train back to my hometown. Becky met me at the station, and drove me back to her flat. After settling into my room, I joined Becky for a glass of wine and a catch up. Her flat was up for sale, and she was moving in with Chris. On the Saturday after a lazy morning, we hit the town and did some shopping. I grabbed a couple of business outfits, and other travel essentials.

After a late lunch we went back to Becky's flat and got our glad rags on for our night out. We grabbed cab and started to hit the bars.

We drank and danced the night away, and had to rebuff more than one male suiter.

I awoke on Sunday with pounding head, we defiantly partied hard the previous night. I dragged myself out of bed to find Becky crashed out on the sofa nursing a coffee and sporting dark glasses. I made myself a coffee and crashed down on an armchair.

For the next couple of hours, we chatted about our upcoming life events. I would miss Becky's surgery as it had been rescheduled, and I would be in New York. I felt guilty not being there for her, but she assured me she would be in good hands. Alison, Chris's daughter was going to take her and look after her after the op.

Around 4pm I felt well enough to get the train home. After a long soak in the bath I had an early night.

The next morning, I still feeling a little jaded from my weekends drinking. I still managed to drag my body out of bed and hit the shower. I dressed in a grey pencil skirt, cream camo top and matching grey jacket. Light makeup and my hair tied into a tight bun, I looked like a proper lawyer, well in appearance anyway.

In my classes I generally kept myself to myself, but I had noticed a guy name Stephen was always sitting close to me. I'm sure I caught him stealing glances of me! I made no secret that I was a Transgender girl, some people accepted, whereas some did not hide their distain. This was the early 90's and the acceptance of the LBGT was still several years away. During our last lecture, the teacher told us to pair up as we needed to debate the pros and cons of a historic case. Stephen practically jump to my side asking if I wanted to pair up, I did not put much thought into it and accepted.

The case was a question of ethics, a lawyer taking a case of a child molester and they knew he was guilty but got him off with a legal technicality. The debate was if you knew the client was guilt, would you still defend him? We had to argue both sides, so I started with for argument for defending him, Stephen argued against. I have to admit that now he had started to talk to me the debate was flowing freely.

We debate both sides of the argument and the teacher called time on the class. Stephen asked if I was free for a drink after class, Alas I had a shift at the restaurant tonight, and I would be busy the rest of the week. I offered a rain check, but I could see he was disappointed. But I assured him with a coy smile that I was not a brushing him off, and asked if he was free for lunch tomorrow? He accepted my offer, and I rushed to catch my bus home as I had to get to work.

At home I stripped of my jacket, skirt and blouse, and slipped on my waitress uniform of black pencil, white collared shirt and black tie, perfectly tied in a Windsor knot. I packed my handbag with my stuff and headed out for the evening.

The next day I was up early, dressed and packed my school uniform to my school bag and headed off to uni.

Stephen again sat next me in class, and we made some small talk. And at lunch he escorted me to his car and drove us to a steakhouse off campus. He opened the door for me and was acting as a real gentleman. We ordered food and drinks. I asked why he was interested in a tranny, he replied I was the most beautiful girl in class and that I was not as stuck up as the others in class.

I wanted to be honest with him and told his I was pre-op, and that I did some extra jobs he might not approve off to earn extra cash. He asked what I had done, so I mentioned the stripping and porn films. I laughed and said I had a photoshoot this evening after classes. He explained he was actually bisexual, so I was the best of both worlds.

Dinner went well, and he did not seem put off as he offered me his arm as we walked back to the car. Again, in class he was attentive, and the day felt like all day date. As the class broke up at the end of the day. Stephen offered to give me a lift to my photoshoot. I thanked him, but politely declined his offer. We exchanged phone numbers and I left to get my bus.

40 minutes later I arrived at Sally's photographic studio and she buzzed me in. She made me a coffee and said I looked better in the flesh than the screen of VHS tape Tony lent her. Sally was in her early 20's, slim and blonde. She asked me what I was prepared to do, and I agreed for do some anal masturbation with a dildo for £50 more. Sally showed me to the dressing area, a table and old-style modesty screen.

I stripped put of my clothes and put on some sexy lingerie and my school uniform. I shouted to Sally and asked how she wanted my hair; she requested a high pony tail. When I was happy with my look, I touched up my lipstick and headed over to Sally.

She had setup a backdrop that looked like a classroom, in the foreground was an old-style school desk and chair. She complimented me on my appearance, and had me take up position in front of the camera and started to take some lighting measurements and focal distance. She was chatting to me all the time making small talk and generally putting me at ease. When she was ready, she asked me to perch my bum on the edge of the desk and strike a pose. She started snapping away After 5 minutes of guidance from Sally I started to get the knack of posing. She asked me to start off trying look innocent but slowly look naughty as I opened my legs showing a glimpse of my panties.

Sally gave me a lollypop and told me to play with it sensually. I unwrapped and popped it in my mouth, and for the next few minutes I sucked it like a cock. Sally asked my me to unbutton my blazer, again several shots of my rubbing my breast, whilst trying to look sexy. I slipped my blazer off and more shots of breast rubbing and panty flashing. Several more shots of me taking off my pullover, and Sally called a break. I was surprised to hear we had been going for 30 minutes.

We had another cup of coffee, and a bathroom break. Sally was asking me so more personal questions, I guess she was trying to figure out if I was a true tranny or a gay guy in a dress. She brought me a selection of dildos and vibrators, and asked me to choose one to use on myself later. I picked a clear plastic dildo that looked like a marble inside. Sally winked and said good choice.

Back on set a started off sucking my new play friend. After a few minutes of deep throating the fake phallus, Sally asked me to start to open my shirt and show off my tits. I playfully pulled on the tie, enough to loosen it but break the knot. One by one I unbuttoned my shirt revealing my bra and breasts. I took the dildo and started to rub it over the front of my panties. I pulled my tits out of my bra and tweaked my nipple.

Sally called another break, she asked me to remove my bra but put my shirt back on. She also advised me to go an loosen up my arse ready to take the dildo. I sat on set and removed my panties, I lubed my fingers and soon had 3 fingers deep in my arse. I started to get lost in the moment that I did not notice Sally was taking pictures again.

I climbed onto the desk and squatted down and lining the dildo up with my boy pussy. It slipped easily into me and I bit my lip. I rolled onto my back, given Sally a great view of the fake cock up my butt. I slowly started to fuck myself with it, my cock grew rock hard and I played with my nipples as I pounded myself. Sally was encouraging me to go for it. I edged myself a couple of times to prevent myself from cumming.

After a good 20 minutes of fucking myself I really needed to cum. Sally asked if I could shoot my load over my breast. I winked and said I'd give it a go. Sally climbed a small ladder and lined up her shot looking down on me on the desk. I started to wank the dildo into my hole, a minute later without even touching my cock I let rip four long ropes of spunk over my breast and even my face. I licked my lips seductively picking up the cum around my mouth and swallowed it and smiled.

Sally called a wrap, and I removed the dildo from my butt. I needed a few moments to recover from my orgasm.

Sally showed me where the shower was, I break the knot of my tie and stripped off my clothes and had a long soak in the shower.

After the shower, I walked back in to the studio wearing just a towel. Sally was perched on the edge of the desk; her skirt was hiked up and her panties were around her ankles. She was thrusting the dildo I had just used on myself in her pussy.

She noticed me and smiled and said I had a beautiful cock and it was a shame I was into guys. I have to admit the sight did turn me on and blood rushed to my cock. Sally notice my towel start to tent, so she pulled out the dildo and invited me to fuck her. At this point in my life I had no interest in having sex with a girl, but I was caught up in the moment and dropped my towel. Sally bit her lower lip and walked towards her.

I slid into her soaked pussy with easy and I did enjoy the feeling of her labia around my cock. Our mouths met as our tongues danced between her mouths as I thrust into her. She pushed me off of her as she peeled off her t-shirt and bra. As our mouths met again out breasts rubbed against each other. The feeling was amazing as we made love, since I had only come 15 minutes earlier, I held on for a long time before my bulls tightened and I fired my load into the first natural pussy I had fucked. Sally rode through 3 orgasms whilst I had fucked.

Spent I dismantled Sally and I were both dripped in sweat so we took another shower together, I even manged to fire another load into her pussy. Perhaps I was bisexual.

I collected up my uniform and stuffed it into my back and redressed in my street clothes. And Sally dressed in only a robe handed me an envelope with my photoshoot pay. She told me I was a natural and promised me more work in the future. She had some non-erotic modelling work for women's clothes I would be perfect for if I would be interested. I accepted her offer and I headed home.