Handyman

[Disco-cuck]

The last duties of the day was Tony installing a lock on the door from upstairs to downstairs. We officially had a suite downstairs. I gave Tony a key for the side entrance, coming in off the garage,(to shared laundry room) and the door from the garage into his suite. “I will be back tomorrow with my stuff.

Tony arrived at 1230 on Saturday with 2 friends, Desmond, and Marcus. Both these guys were solid, fit guys. Desmond was maybe 30, and Marcus probably mid 40’s. They were all looking like NFL guys. Big, black and each of them looked like they could bench press 500 lbs. I was busy upstairs and just went down to officially say welcome, and tell Tony if there was anything he needed, not to hesitate to ask.

He seemed to immediately get his music going. I could hear them coming in and out of the house, talking and laughing. I couldn’t really hear what they were saying, but I wasn’t listening that hard. Gina was sitting on our back deck reading a book. She was sunning herself; bikini top and her mom shorts. I was sitting there with her not really doing anything. I heard Tony’s voice coming from around the side of the house. Desmond and Marcus walked into the back yard with Tony. They were admiring the back yard, small garden, and standing beside the covered deck. Gina put her book down, leaning over the deck to say hi. Her bikini top straps had been hanging by her side, so her arm was across her bosom, which definitely pushed her tits up. A bit of small talk, and she said “nice to meet you.” She disappeared into the house. She reappeared a few minutes later, having changed her outfit. “I just realized how messy that garden looks down there. I’m going to do some gardening.” She had put on some spandex yoga shorts and a thin, almost see through t-shirt, as well as a baseball hat.

Holy shit, I thought. The shorts were so small, and tight. I could almost see her pussy lips. There was no way she was wearing underwear beneath them. She tied the t-shirt just under her tits. I was shocked that she didn’t seem to care how revealing her outfit was. Or was I just feeling insecure?

She walked down the stairs to the small garden and began to pull weeds on her knees. The guys had continued to move Tony’s items in, but through a window downstairs or coming into the side entrance, they’d see Gina. From my vantage point on the deck, I could see her round ass, in the pale grey shorts. They seemed see through with the sun beating down. Suddenly Marcus came around the corner carrying some folding chairs, and putting them down under the covered deck. I could see him stop and check out Gina for a few seconds. He finally left, then Tony and Desmond came around the corner and walked over to Gina. I couldn’t hear what Tony asked her, but Gina responded “Sure. I will bring them down to you.” As she started to get up in went into the house, so it wouldn’t appear to be eavesdropping.

I pretended to be in the other room and walked into the kitchen. Gina was filling a plastic bowl with ice cubes. “Tony asked if they could get some ice for their drinks.” Her face was flushed and her nipples were rock hard. I’m pretty sure it wasn’t from getting the ice. She closed the freezer door and I heard her going back down the outside steps. I went into our bedroom, the closest window to his door. “Knock, knock” I heard Gina say as she must have walked into Tony’s place. I could hear some faint talking through his music, and some laughter. I started to feel jealous. I wasn’t sure if it was jealousy over Gina or Tony. I was so confused.

 

[sissymika]

?

 

[chelseacd]

No one wants to fuck Gina

 

[sissymika]

I guess disco-cuck petered out..no pun intended!

 

[chelseacd]

LO L ya I was waiting for him to come back home from out of town work and find Tony fucking the shit out of Gina . And his stuff moved into the extra room

 

[SquirmingSub]

any more to this story line?

 

[chelseacd]

It was getting good then he stopped

 

[Disco-cuck]

Hi folks, I'm sorry I've been slow to continue the story as life has been a bit crazy of late. I've been encouraged by your positive comments and requests for the rest of the story. Hang in there, and I will give you more tidbits in the next few days.

 

[AliasBilly]

Hi folks, I'm sorry I've been slow to continue the story as life has been a bit crazy of late. I've been encouraged by your positive comments and requests for the rest of the story. Hang in there, and I will give you more tidbits in the next few days.

I love bi-cuck stories and am anxiously awaiting more from you. Also, please send me your address. I want some of Marcus, too, as soon as he's finished with your wife!

 

[Disco-cuck]

I started my new job and was ****** to focus my attention on learning a new field, with a strong understanding of chemicals, working around food, thorough site inspections, paperwork, etc. As much as I wanted to focus on Tony, Gina, our home, and the new living arrangements, I also didn’t want to mess this up. I knew Tony had put a good word in for me, and I also didn’t wish to give Gina the impression I wasn’t a hard-working, smart and adaptable guy.

My first few weeks on the job were busy. I stayed longer, never complaining about extra work, and Russ appeared to be impressed by my work ethic. I had already been away for my first overnighter with my mentor/trainer Chuck. That went well, and I knew I could find my way back to each location and continue on the work we had started.
I was thrilled to be able to show my independence to Russ, Tony and Gina. I had a lot of people I was trying to impress.

My secret life was on hold. I observed Tony’s daily routine. He would be working Monday to Friday, and sometimes on weekends, but often went straight to the gym from work, so would arrive home about 5 in his workout gear, make dinner, then go out for a run 3 or 4 nights a week and get back about 7:30. He’d often do his cool down and stretches on the back lawn when it was sunny, and under the covered deck when it was rainy. Of course, I wasn’t the only one to notice his schedule. Gina almost immediately made changes to her wardrobe. All her bras and underwear changed from her ‘comfy, maximum coverage’ goods to sexy, lacy and barely there. I was impressed by her taking better care of herself and wanting to dress sexy. I never said much, but as I’d often get home first and still handled the laundry duties, I could see her transition. I also noticed her showing more cleavage, and wearing more clingy clothes, at work, and of course around the house. Gina had transformed from a woman that didn’t seem to care about what she wore or how she carried herself, to updating all her undergarments. She began eating better, joined a gym and had dropped a bit of weight as well. She was getting incredibly toned, tanned and sexy. That didn’t do much for me, mind you. I wasn’t getting much of a sniff of anything sexual upstairs.

I had less opportunity to dress as Rachel, and I was kind of missing it. I barely saw Tony either.

Back at my job, Russ told me he was going to fast track my Corporate training week. He’d usually wait and have someone go after passing their 6 month probation, but he wasn’t sure what his boss would say about it. It didn’t really matter to me as I had only wanted to know that I was doing well. It was now September and I had been on 3 overnight trips, both for 2 nights. Of course, while I was away, I wondered what was going on at home.

I did manage to have a bit of fun downstairs, when Gina stayed late at work, then went straight to a gym class. She’d get home about 8, and I was able to get my daughter picked up from school by my in-laws, saying I also had to work late. I actually didn’t usually have to work past 4, so I’d get home, change into something Gina had left hanging on the bathroom door, and when Tony got home, I’d come down to ‘do the laundry’ making enough noise that he’d hear me. I’d get invited in, and we’d have a couple of hours of me being Tony’s girl. I’d always suck his dick, and he would always give me a good, rough pounding. The weeks I was away, I really missed our meetings, but I’d have my laptop with me, and I would dress up in my hotel and Skype with Tony. He’d get me to do some various things for his enjoyment. One day he had me laying on my back, flipping my legs over my head and shoot into my own mouth. I managed to get about 75% accuracy, with a partial facial. That became a regular ritual.

He made me swallow, which wasn’t a big deal, but he really encouraged It. One night, he had some buddies over for a boy’s night, and I ended up putting on a show for them all. It was on a laptop, so it was sort of surreal. I felt incredibly sexy showing off for everyone.

In late September I ended up having to adjust my work schedule to provide service out of town over a weekend. It was a warm weekend and almost felt like summer. The reason I’m providing this information is that when I got back from my trip Sunday afternoon, Gina was acting a bit differently. I couldn’t figure out what was different. She wasn’t mad, or sad or any other emotion I could think of. I asked, of course and she said everything was okay. Later on, when my daughter was in asleep and we were just getting settled in bed she dropped the bombshell. “So Tony and I got together while you were away.” she blurted out in the dark. I guess she didn’t want to see the look on my face. I was sort of surprised, but I knew it was only a matter of time. I broke the awkward silence with “Oh………..so what happened?”

She said she had gone out Friday night with some of her girlfriends for dinner and drinks. Her friends were baiting her a bit with comments about the hunky guy living downstairs. The drinks continued and she took a cab home about 10 pm. She said she had spilled red wine on her dress, so she got home, stripped off her dress, put on a robe and took her dress to the laundry room to get the stain out before it set. She said she had one of her friends (Dana) on speakerphone and was obviously speaking loud, and laughing in the laundry room. She then said she realized her underwear also had wine on them, so she removed them and was now in just a robe. Tony opened the door to see what the noise was all about and Gina jumped, dropping her phone, which slipped down between the washer and dryer. He was wearing only some loose-fitting shorts. That made her giggle nervously, as Tony stood there assessing the situation. Gina was tipsy, but tried to pretend she wasn’t. She said she crouched down to try and get her phone and her robe was almost completely open showing Tony her tanned, bare breasts and possibly her pussy too. Tony stood there watching her, then finally reached in and pulled her phone out for her. She said she invited Tony upstairs on the deck for a nightcap to thank him for rescuing her phone. He said he’d be up in 5 minutes.

She went upstairs, brought a bottle of wine and 2 glasses out to the deck. She lit the 4 candle set in the middle of the patio table.

He suddenly appeared, and she was again a bit startled. They sat across from each other and even though her robe had been tightened and secured when she left the laundry room, it had again loosened, and the warm summer breeze felt good on her naked skin. They were both sitting back from the table so Gina said she couldn’t help but see Tony’s growing cock pushing against the fabric. Their conversations were always flirtatious, and this was no exception. She said that Tony had been the topic of discussion with her and her friends that evening. That seemed to add fuel to the ever-growing fire. Tony asked what was said, and Gina just said that her friends were wondering why they hadn’t got together yet. At that point, Tony said “So why haven’t we?” and they both just stared at each other, not saying a word.

“Stand up, Gina.” Tony finally broke the silence. Gina said she put down her wine glass, and obediently stood up. At that moment, a gust of wind caught her gaping robe and it opened completely. Gina said she instinctually went to cover up with her hands, but Tony said “don’t move” so she dropped her hands and her naked body was completely *******, her robe blowing like a cape behind her. She said it was like a dream. Tony took her hand and pulled her toward him. She ended up straddling him, face to face, sitting on his lap and they kissed passionately. She said things just went from there. “How so?” I asked, wanting to hear more details. She said she could feel his hard cock underneath her as he kissed her mouth, neck and breasts. She said her body was completely electric and all she could think of was having Tony take her, in any way he wanted.

I guess she was so wet that his shorts were wet from her. There was no resistance as he slipped into her and she said it was an experience she’d only dreamed was possible. She said she wasn’t sure how much time passed but by the time the dust settled, they had both come (he pulled out) and they went off to bed separately.

She said Saturday morning she woke up, felt quite hung over, and a bit sore from their fucking. She said she showered, got dressed and went downstairs about noon, to apologize for her behavior the previous evening. She had also felt pangs of guilt and wanted to tell him that Friday night was a ‘one time’ transgression. They would put it all behind them, and act professional and adult from this point forward. She knocked on the door about noon and Tony answered, just freshly showered. As usual he was nicely dressed and polite. He invited her in, and she sat across from him. They apparently both felt remorseful and apologetic. She said as she stood up to thank him, she gave him a hug. I guess that shattered everything they had just discussed.

She said they spent the whole day sucking, fucking and exploring each other. She said they must have fucked 9 or 10 times, falling asleep in the wee hours of the morning. Sunday morning they fucked again, and she went upstairs, got cleaned up and went to pick up our daughter who had stayed at her grandparents for the weekend.

Of course, I had arrived home only a few hours later, and she was still trying to process all that had transpired over the weekend.

I just said “wow” and we just lay there in silence. I thanked her for her honesty, and said we could chat more about things, and could most certainly work things out. Of course, I really had my doubts if we could work things out, but my mind was also trying to process the possibility of losing Gina, losing Tony, and possibly losing my mind.

 

[Disco-cuck]

I got the news that I would be attending my companies corporate training in Minnesota in mid-October. I was excited to go and gain further knowledge. I was also wondering how my situation would unfold, given the fact that Gina and Tony were now in a sexual relationship. Gina confided in me that during their Saturday fuck-fest, Tony had shown her a video he had posted on a porn website. It was me; long hair, and sexy, lacy lingerie, sucking myself off and swallowing my own cum. She was very pragmatic about it. She said that given the fact that I was no longer interested in women, and becoming a girl to pleasure men, that she didn’t really feel that badly about her and Tony. I didn’t really have any excuse or defence about my actions. I just sat there quietly cringing and wondering how I’d even give an excuse for my behaviour.

The next day I confronted Tony and asked him how he could betray what we had by showing my video to Gina. Fuck, I didn’t even realize he was recording it. And why the fuck did he post it on a porn site? Rather than be apologetic, Tony flipped the script and said I should be thanking him. Tony said he had helped me become what I was truly destined to be, and that I had no idea how to satisfy a woman like Gina, but only was beginning to figure out how to be the perfect sissy slut to dominant men. I kind of looked down at my shoes as he took me down a notch or two. I was dressed in my work clothes as I had just decided to discuss this man to man. By the time I was done, he had reduced me to a whimpering sissy. I ended up apologizing to him. He said he would have to think about if he would or could forgive me. I got a bit of a panic attack, thinking I might lose him. I almost begged him to give me another chance, to which he said “Get Rachel back down here in 15 minutes and I will see if we can overlook this.” I thanked him and raced upstairs to get dressed.

I was back downstairs 12 minutes later, dressed as slutty as I could, hair done, make up done, and a large butt plug in place.

Tony really took out his frustrations on me. It was by far the roughest he had been with me. He slammed his cock down my throat, and I blinked tears away trying not to gag. Once he was tired of that, he spun me around, had me hold my ass open and he attacked my ass deeply and forcefully. It went on for at least 20 minutes. He then had me get into position for me to cum into my own mouth. He positioned himself to ass fuck me downward as I was doing an almost handstand, except my neck was bent to await my drops of cum. The heavy pounding of my ass in this position was incredibly hot, and I shot my hot spunk all over my face as I moaned in satisfaction. Tony pulled out about a minute later and shot his thick load onto my awaiting tongue that had been trying to lap up my own cum.

Tony stood over me and told me that anytime he wanted to fuck me or share my sissy body or videos around that he would do it.

He also said that Gina had completely surrendered herself to him without any urging from him. She told Tony that she would be happy to give him any and every pleasure he desired from that moment forward. That didn’t really sound like the Gina I had known, but the landscape had changed so quickly, and I no longer questioned what was going on.

I didn’t really have too long to sort things out anyways as the following week I had my out of town visit on the Wednesday and Thursday nights, back on Friday, then was leaving for Minneapolis/St. Paul on the Sunday to be ready for Monday morning Corporate Training.

While I was on my bi-weekly service trip, Tony once again had me play as Rachel, and had me finish the evening by eating my own cum. As I finished, I could hear Tony talking and Gina’s laughter, so I figured out she had been watching this, too. It really didn’t matter anymore as things were well past spiralling out of control. I returned home on the Friday night to find a note from Gina saying she had taken a cab to Dana’s house and was staying the night. Our daughter was at her grand-parents house. I thought about going downstairs to see Tony and as I got to the laundry room, I could hear music playing in his suite. I stopped and listened carefully and could hear Gina inside, obviously being fucked rather well. I stood there listening and stroking my cock as they became rather vocal. I shot cum in the laundry room against the wall, as I heard them finish up, then she came running into the shower, with him in hot pursuit. The peep hole/glory hole was partially filled in so I couldn’t see much, but he seemed to pin her in the bathroom and I heard her say that her ass was still quite sore and to go slow. Anal sex was something she had only allowed me to try once, on our second wedding anniversary. She didn’t have much of a reaction and it never was repeated, so I was stunned when I heard her speaking as if it was a regular menu item. Her loud moaning got me hard again and I jerked off and shot another load on the first one.

I went upstairs and got ready for bed. I lay there for quite a while before drifting off to sleep.

Saturday was pretty much a blur for me. I was packing my bag for my week away about 3, when Gina arrived with our daughter. We both just pretended it was business as usual, not knowing where to even begin a conversation. We had dinner, watched a family movie and went to bed about 10. The awkward silence eventually became sleep, and I had very bizarre dreams, which caused me to toss and turn. I had to leave for the airport by 11, so I was up and organized early. As I was putting my stuff in my vehicle, Gina came out to the curb and wished me good luck. I said thanks, then said “I guess we have to sort a few things out when I get back?” She just nodded yes and said she was sure we could get things sorted out, and find a rational outcome.

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.

 

[SquirmingSub]

Amazing story line...

 

[AliasBilly]

I love this story!

 

[donaldelliott11]

One of my favorite stories! Thanks.

 

[SquirmingSub]

Looking forward to the next chapter.

 

[Disco-cuck]

Lots more to tell. Just have to find the time with all that's going on in my life. Thanks for your patience

 

[Disco-cuck]

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. Me 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.”

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

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 and said “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.

 

[chelseacd]

Very nice

 

[sissymika]

I really enjoyed the continued story and eagerly look forward to more.

 

[Disco-cuck]

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, “Hey, come in here and have some fun.” It seemed to be directed to me, and 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 neighbourhood 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.

The flight home was uneventful, and I snoozed a bit, but it was a 90 minute flight so I was back home in no time at all. I had left my vehicle in the airport parkade, and 25 minutes later I was pulling up in front of my home. I recall Gina’s text saying to go to Tony’s suite as soon as I got home. I went in the side door and there was an envelope on the door that said Ray/Rachel on it. I opened the envelope and a key fell out onto the floor.

The note read:
Welcome back home. When you were gone, Tony moved his things upstairs and your things are now downstairs. Given the way our lives were going, it just made sense to make this move. We’ve redecorated a bit, so we hope that Rachel will like her new home. Don’t forget that rent is due on the first, $500.00 per month. We hope you adapt quickly to your new place. We left a few food items in the fridge for you.
Love,

Gina & Tony