Handyman Pt. 05

I arrived at my hotel and got checked in. There was a bar downstairs in the hotel, so I thought it might be nice to have a drink before I went to bed. I had brought my Rachel clothes with me, at least, my lingerie and make up. I didn't really have a dress, but I had bought a shirt that definitely looked a bit girly, and with a pair of jeans, and my hair done up with my much-improved make-up technique, I gave thought to going downstairs as Rachel. I couldn't believe how excited that thought made me.

I went to my room, had a hot bubble bath and got myself dressed up. I was downstairs by 7 and ordered a glass of wine and appetizer for my dinner at the bar. I was still a bit nervous, so I sat in a quiet corner, where I could see the other patrons. A few couples, a table of guys watching the NFL night game, and a couple of single guys floating around as well. Nobody seemed to notice a guy in drag sitting sipping wine, so I felt a bit more confident. I was going to finish my glass of wine and call it a night, when the bartender came to remove my appetizer plate. He dropped another glass of wine in front of me, saying "That gentleman at the bar sent this over to you." I got sort of a sinking feeling as I looked over. A fellow with salt and pepper hair, probably mid-50's was smiling and holding his drink up to signal 'cheers'. I smiled awkwardly, and mouthed 'thank you' and gulped the last of my first drink down.

With that, he picked up his drink and began walking straight for me. Oh well, I guess I'm having a drink with this guy.

"May I?" he asked, sitting down before I could reply.

"of course, yes" I said, as he smiled.

"My name is Barry. I'm in town on business. I thought it would be nice to have some company." "I'm Rachel." I replied.

We made small talk for a bit. Barry was a sales rep for some auto parts chain. He was 58, married, and his kids were grown and married. He was from just outside Akron, Ohio. He started to play the 'my wife doesn't understand me' card and said they slept in separate rooms due to his snoring.

I just made up some stuff on the fly, saying I was in town for a corporate training seminar, but tried to be as vague as possible. As my glass of wine got to about half full, I mentioned I'd have to wrap things up pretty quickly, as I had a big week ahead of me. I was tired from my flight and lack of sleep the night before, and feeling a bit tipsy as well.

Barry asked if we could have dinner tomorrow night. I said that would be great.

"Nothing too fancy, but nicer than here." He said as we walked to the elevator. I was on the 9th floor, he was on the 12th. As the doors to the elevator closed, he put his hand on my back, rubbing my lower back until his hand was on my ass. I felt a bit of a tingle, plus incredibly nervous. I took a step forward to prepare to get out of the elevator as it headed up. He stepped up behind me, pulling my hips back against him. I could feel a hard cock on my back.

"Sure you can't stay up a while longer? I have some drinks in my room." Before I could answer the doors opened to the 9th floor. He was now kissing my neck. I had about 3 seconds before the doors closed so I had to decide quickly. Too late. The doors began to close.

"Great" Barry said, as the elevator whisked us to the 12th floor. My heart was racing, an equal balance of fear and excitement gripped me. The doors opened and he grabbed my hand and we walked about 3 doors down, and he popped his key card in. Green light. Here we go.

The bed was a king size. Desk with a wooden chair, and a single leather chair by the window.

"I've got vodka and rum." He said. "Which would you prefer?"

"Vodka, please" I replied seeing a bottle of orange juice on the desk. "with some OJ?"

I walked over and looked out the window to check the view. The lights of the city glistened, and the view was way nicer than from my room. I looked off into the distance, thinking about Tony, Gina, and my home life in tatters.

"Here you go, Rachel." Barry said giving me the glass. We clinked them together, then each took a sip. With that, Barry took my glass, and put both on the table. He grabbed me and pulled me close. He was about 6' tall and pressed his mouth against mine. I had tucked my cock, as Tony had taught me, but I could feel me getting excited. Barry's cock was pushing against me as his tongue explored my mouth, rather aggressively. He moaned and said how beautiful I was. His whiskers were a bit scratchy, but I liked the fact he found me beautiful.

His hands were busy; rubbing my lacy bra. I figured I'd better try and steer this ship, so I decided to give him a blowjob. I put my hands on his cock, and he moaned his approval. I began to drop in front of him and began to unbuckle his belt as my knees hit the floor. It only took a few seconds, but his pants were at his ankles and I was reaching inside his boxers to release his dick. Very hard and red, about 7 inches, cut. He was oozing pre-cum like crazy. Before I could even take a breath, he had his hands on my head, pushing the full length of his cock into my mouth. Thankfully, Tony's cock had prepared me to take this one without gagging and I went to work on it. In less than 5 minutes he exploded, and I had eagerly swallowed his load. He was shaking and shivering as I let him go soft in my mouth.

"That was amazing" he said is a sort of whisper.

"Yes, it was" I replied. "but I need to get going." I got up from the floor as he sat backwards into the chair.

"I'll meet you downstairs tomorrow night for dinner." I said walking toward the door.

"Good night" I smiled and opened the door.

"Good night, and thanks again Rachel." Barry replied as the door closed beside me.

Day one of my training was interesting. I got to the head office about 8 for our 8:30 meeting. I found my way to the training department and got my seat. There were 10 "specialists" from all across America, including myself, and we all got up and introduced ourselves. There was a couple of ice-breaker types of games where we teamed up and got to know each other. I was the only guy with a pony-tail, but one other guy also had longish hair. It was interesting learning a bit about how other people did their job. Later in the morning, a person from our Human Resources dept. spoke to give us more information about our medical & dental benefits as well as other corporate information. There was a brief video from the CEO officially welcoming us.

One thing that shocked me a bit was the announcement that our company was very supportive of transgendered persons. One of the employees in HQ was TG and she also had a short video expressing her thanks to the company for being so supportive and progressive. I hadn't given any thought to what I was, but drawn to Fay, the woman in the video. She looked to be Asian. I thought that if I saw her this week, I'd say hi, and maybe chat a bit about Rachel.

The guys in our group were a variety. All between 22 and 50, a mixture of white, black, Hispanic and from all across the country. Some older guys had other careers previously and some of the new guys were straight out of College. They all seemed nice enough and wanted to go for beers each night after class. Then dinner, then out for a few more drinks. I said I could join for some of the sessions. After work I went out of the HQ building and noticed a thrift store across the street. I figured I would see if I could find a dress for tonight. It was a great store and I found 3 outfits that looked like they would fit well. They also had some lacy items that caught my eye. I found some stay up stockings, and a few lingerie bits, and some sexy dresses. I didn't dare try them on at the store but being a thrift store, I got all the items for under $50. I headed back to the hotel to try on my stuff and prepare for dinner with Barry.

I was sitting in the bar drinking a glass of wine when Barry walked in just before 7. I had left a message under his door telling him where I would be and when. I wore a lacy black dress, that had some stretch to it, so it clung to my body. I had a padded bra to give me some shape and with the stay up stockings I wore, I looked quite good! I'd found some classy looking sandals too. I hadn't figured out walking in heels yet.

He complimented me on my looks. I blushed and thanked him. He said he wasn't that hungry, but was excited about spending time together. I translated that to mean he was horny.

We crossed the street to an Italian restaurant and had a bite to eat and he ordered a bottle of wine.

As we chatted, I mentioned that I was married, trying to figure out if I should forewarn him that I wasn't actually a girl. I didn't want him to freak out and possibly go nuts. I've heard tales of such situations happening. We clinked glasses together with him saying here's to unhappy marriages.

"So when did things start to go bad for you?" He asked.

I gulped, then figured I'd best give him the goods. I explained that Tony had come into our lives and how I had transitioned, with his guidance and pressure. I then mentioned that I actually felt more comfortable dressed like I was tonight. I saw him searching my face to see if I was kidding, or maybe he was looking for male characteristics that I was trying to hide.

There was a long pause. Barry took a sip of his wine, then just tipped the glass back to finish it.

"So?" I floated that word out there, unsure of what he was thinking.

He looked at me straight in the eyes.

"Well I can't imagine you as a guy. You make such a sexy woman." He put his hand on mine. "Sexy." He repeated.

I was relieved, and also a bit nervous now. That didn't even appear to be a speed bump on this evening's road.

We were pretty much finished our meal and he paid. We walked back across to our hotel and to the elevator. As the doors closed, I pushed the 12th floor. He pulled me close and kissed me passionately. I responded with the same passion. I think it was my way of saying thank you; that he accepted me as Rachel.

We got to the room and he had a bottle of white wine in an ice bucket. I excused myself to use the washroom.

I stripped down to my padded bra, lacy panties and stay up stockings - all black. I made sure my cock was still tucked as best I could.

He was standing by the window holding 2 glasses of white wine when I came around the corner. I could see the outline of his cock which seemed to be ready for me. He had also put music on which made the mood. We sipped the wine and this time I took both glasses and set them down. I undid his pants and let them fall to the ground. He already had a wet spot of precum on his boxers. I pulled them down and began to lovingly suck him. He was standing with his back to the bed, so he took a half step back and sat down on the bed. He was moaning his approval for my great oral skills. He stopped me after a few minutes, saying he wanted this to last for a while. He pulled me onto the bed on top of him and I lay on him feeling his hard cock between us as we continued kissing. My jacket was on the bed and in the pocket, there was a small bottle of lube, which I took out and applied to his throbbing cock with one hand, while secretly lubing my ass with my other hand.

I pulled the narrow fabric aside and slowly sat down onto him. He moaned as I rode him, slowly at first, then began to pick up the pace. He rolled me onto my back with him now on top. My legs were between his chest and mine and he thrust deeply into my ass. I was now moaning uncontrollably, and that seemed to turn him on more. He let out a growl as he filled my ass with his load. He bucked and twitched as he collapsed on top of me. At the same time, I realized my cock was rock hard and I was now sticking out of my lacy panties, and I shot a few seconds behind him. I was kissing his neck as he was breathing loudly.

"That was amazing, Rachel." Barry said, as he caught his breath. We lay there for a while and his dick finally softened enough to slip out of me. I was tired but also energized after such a hot session.

We fell asleep beside each other for about a half hour. I thought I should have a shower, so I tiptoed into the bathroom and turned the hot water on. It felt so good to have the hot water on my hairless body, and I felt like I was in a dream world. I was brought back to reality with the shower curtain opening behind me and Barry stepping in. We kissed again; and began to wash each other. He held my cock as he washed it. I began to get hard again, as we stroked each other. He turned me around and pushed his hard, soapy dick into my ass again. With the steam it felt as if I was flying in the clouds and he came again after a few minutes. As we dried off, and I got dressed, he told me he was checking out the next day, but wanted to keep in touch as he thought he may be able to visit me, or we could plan another getaway. I told him my work took me out of town a few nights a month and perhaps we could meet there. We exchanged emails.

I went off to our training the next day, and at lunch, I noticed Fay sitting with someone having lunch. I walked over to her table and said hi. I told her I was impressed by her video. She asked if I would like to join her, and her workmate, Karen. I said sure and sat down. I instantly connected with Fay, and Karen was quite nice as well. I wasn't planning on saying anything about my situation, but I felt incredibly comfortable around them both. I asked them to keep it to themselves, as I was still unsure how I was planning to live. Transitioning to Rachel ended up being rather effortless so far, however I wasn't sure how far I was prepared to go on a full-time basis. I certainly knew that being Rachel all the time was something I wasn't quite ready for. Fay asked me if I would like to come to her place for dinner on Thursday night. I said it was my training teams last night, and I did need to hang with the guys a bit early on. She said she could pick me up at the hotel after the event with the guys. She also suggested I come to dinner as Rachel, if that was okay. I said that would be fine, and I could make an excuse to the guys to make it an early night.

The team dinner went from 6 to 7:30, but I excused myself just past 7 and went upstairs to transition and to tell Fay I'd be ready about 7:45. She picked me up out front of the hotel. Interesting, as when I got off the elevator I could see into the bar and the guys were busy whooping it up. As I walked by, I heard one of them yelling at me.

"Hey, come in here and have some fun." I laughed to myself, thinking, if he only knew.

I hopped into Fay's car and we hugged. We ended up at her place, an apartment about 15 minutes away from the hotel. It was decorated nicely, and I felt right at home. She lit some candles, had soft music playing and put out some appetizers, and we had some wine and chatted about everything. I confided in her about Tony, Gina, and my dilemma. She was very understanding and after we finished the bottle of wine, Fay suggested I should stay Friday night instead of flying home mid-afternoon after class finished. She said she could rebook my flight and I could stay Friday night at her place. I was all in! Fay was like my new best friend, and she accepted Rachel which was reassuring.

I took a cab back to the hotel about 11 and was excited for my last day of Corporate Training. The day was wonderful, and I was excited about spending the evening with Fay. The guys were all great, and I was thrilled to make a few friends during the week. We agreed we would stay in touch, but as what usually happens, people seldom follow up with those types of plans, especially since we are strewn around the country.

I had a couple of hours after training ended, to when Fay was off work, so I brought my suitcase to her desk, and decided to do some shopping. Fay gave me a couple of names of stores to check out. She was right on, as her choices were perfect for my style. I bought a couple of new outfits, plus a few more lacy undergarments. I was thinking that I might have to throw a few items out of my bag, in order to get Rachel's new clothes in. I was trying to wear more

androgynous garments, when I wasn't going full Rachel, so I figured that Gina wasn't the only one who had made some huge wardrobe changes.

That made me think of Gina, and that I should let her know I was going to be coming back Saturday instead of Friday. I texted her, and her reply was "No problem. When you come back, please go directly to Tony's suite. There's something new you need to see as soon as you get home." So I asked if everything is alright. She said yes, not to worry. I decided not to read too much into the situation, especially given the fact I was 90 minutes away by air, so there wasn't much to be done until Saturday.

Fay met me in the lobby and we headed back to her place where I got freshened up. She said we were going to meet her doctor for drinks. His name was Brad, and he was also a close friend. He was the one who got her started on female hormones, which really started her transformation on the inside. She had begun to grow breasts, and had changed her appearance quite a bit. I said that I might be interested in doing something similar, but hadn't completely made my mind up yet.

We drove to a bistro, where Brad and a few other friends were waiting for us. It was a fun time and I felt completely comfortable discussing Rachel with Brad and his friends. About 10, Brad asked Fay and I if we would like to come back to his place with his friend Rob. Rob had been chatting with Fay most of the night and they seemed to be hitting it off. I looked at Fay and she nodded yes. I drove with Brad and Rob went with Fay. We ended up in a very posh neighborhood called Kenwood.

The house was magnificent, and after a brief tour we ended up in the living room with the fireplace on. The room was dark so the only light was from the fire. Brad sat beside me and ran his hand up and down my back. I was a bit tipsy after the earlier drinks and my full glass of wine would have to wait. I put my hand on Brad's leg, which felt quite muscular through his pants. The next thing I knew, we were making out like teenagers. I briefly glanced over at Fay and they were already partially naked. Rob was sucking on Fay's cock and she was moaning quietly. I was super horny as well and I dropped my dress, leaving my lacy bra, thong and stay up stockings. Brad didn't hesitate and got naked quickly. His cock wasn't long, but it was thick, so I was able to get all of him in my mouth without any problem. He got hard really fast and decided to turn me around and started to rub his erection between my cheeks. He reached for some lube which had been in the coffee table drawer. He slowly pushed his way into me, and I pushed backwards, as he filled me up. I moaned loudly.

Brad was totally into fucking me and instantly began to pound me hard. I looked over at Fay and Rob was giving her the same treatment on the other sofa. Fay's cries were very high pitched; almost squealing. She started to yell she was coming, and I watched as sperm shot from her small, semi-floppy cock. Rob pulled out and after a minute came over to where I was being slammed. He walked around the back of the sofa and stuffed his hard cock into my mouth to complete the spit roast. It was a pretty hot scene, and both Rob and Brad came within about 30 seconds of each other. Rob was first and I could taste his juice mixed with being inside Fay, which was really hot. As Brad slowed down in his gyrations, I noticed Fay had slid underneath me and was sucking me. With all that had happened in the last few minutes I also came, and Fay lovingly swallowed every drop. We all crumbled into a panting, sweaty pile of bodies.

After a few minutes we were all invited into a huge shower in Brad's ensuite bathroom. We rinsed off and as we started to towel ourselves dry, Brad opened the sliding glass door off his bedroom to show a sunken hot tub. The lighting was amazing, and Brad suggested we get our drinks refreshed and slip into the tub. Fay and I ended up making out naked in the hot tub as Rob and Brad cheered us on with comments like "so hot" and "fuck ya". Fay's tits were small and perky, and I was actually jealous as I had a flat, boy's chest. She enjoyed me sucking on them and we ended up rolling out of the hot tub and 69ing for the guys. We only got about 5 minutes into it before the guys decided they were horny enough to fuck us again. We all ended up in Brad's king size bed. Being fucked beside Fay was incredibly sexy and we all came again. Before we left (about 4am) we ended up sucking off Brad and Rob. We got back to Fay's about 4:30 and showered, then went to bed for about 6 hours. I had to be at the airport by noon for my early afternoon flight. I was tired, but buzzing from all the fun. Brad had said he would stay in touch, and also said he would write me a prescription for female growth hormones, like Fay was taking. I said I wasn't 100% sure yet, but was probably going to decide soon, and I was getting a lot more into being a gurl.