The Transition Ch. 03: Aftermath

Greetings and thanks again for reading my story. This is the third part of the story, so go back and read the other chapters if you want the whole story. As always I really appreciate any feedback you leave in the comment section down below. Be sure to follow me if you like the story so you don't miss any future chapters.

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I woke up in the middle of the night to find Jamie in the bathroom down the hall wearing his boy clothes and washing off the last bits of makeup from his face.

"I didn't hear you get out of bed, are you leaving already?" I asked a bit concerned that he was running off in the middle of the night.

"Yeah, I have work in the morning and I just figured I would get out of here and get a little sleep before work." Jamie said with a hurried tone in his voice. He was clearly trying to give me the slip and get out of here as fast as possible. What had gone wrong, the evening was incredible the transformation into a woman was better than I could ever have hoped for, and the little bitch had fucked me like her ass was on fire so what was with the escape act.

"look .. it was a crazy night , but I just need to get home is all." Jamie rushed his words as he was clearly bothered.

Before he left, I caught him at the door and assured him that I had an amazing time a the sex was incredible. I said I needed to see my girl again sometime and stuffed a pair of frilly blue panties into her hand before showing her out.

I didn't hear from Jamie the next day or the day after, I began to fear I had been too aggressive and had lost my chance. Well at least that night was fucking incredible and it would be a long time before I forgot about that sex. I assumed Jamie just needed some time to work things out in her head. Sissy regret apparently happens sometimes when a crossdresser or sissy gives in to her urges and then feels ashamed of having done so after the fact. I kept picturing Jamie in my head all dolled up and on her knees sucking on my cock. I knew Jamie could be that sexy girl again, and with a little work could become a woman for me, He just needed to work it all out for himself and understand what I knew already, that he was never going to be a man and could be happier as a sissy or a woman.

The following day my phone buzzed in my pocket. "Sorry about running out like that, I guess I just freaked out a bit." Jamie said.

"No worries, It was a wild night, I can see how you may have been overwhelmed by everything. I was getting worried that you didn't want to see me again or something."

"Nothing like that, I just need some time to think things over I guess."

"No problem babe, I don't want to make you feel weird about anything, figure things out and get back to me, I'd like to have some fun again sometime." I tried to sound comforting.

"Thanks Mark, I did have fun... I'm just not sure I should do it again."

"Well let me ask you this... have you worn the panties I gave you the other day?"

"Well... yes." Jamie admitted reluctantly.

"Then I think you know what you really want to do, but take your time, I'm not going anywhere."

With that Jamie said goodbye and hung up. I could tell he was a little freaked out about our dress up time the other night. I knew he hadn't taken the panties off since he left the other night and was going the be back. I had shown him how fun it could be to let go and become someone else, and I had seen the enjoyment experienced. I would have to play my cards right, but Jamie was going to make a fine girlfriend someday, I was sure of it.

The next part of my plan was to have Jamie associate spending time with me as spending time as a woman. I would have to insist that whenever we were together that he would be expected to wear panties upon arrival and change when he got here. I would have to stop referring to her as a man and try my best to only use female pronouns to reinforce that I only looked at Jamie as a woman and would treat her as such. The thought was that over time these conditions would slowly help Jamie start to feel like more of a woman and crave to be at my place, as my house would represent a safe haven for her female tendencies. This might seem like some kind of brainwashing or something, but I saw the woman inside light up when she looked at herself in the mirror the first time. I saw the change sweep over Jamie in the bedroom as she embraced her role for the night. the connection was there and she felt it too.

Another week went bye, and Jamie kept in touch sporadically. I think she was still a little freaked out by all that had happened. I However was in an incredible mood, I bet I jerked off every day thinking about making Jamie my little cock sucker, Damn that was an intense night, and I couldn't keep my mind off it. I remember sitting in my office pretending to get some work done, while listening intently wondering if Jamie was actually going to dress up like my whore so I could fuck her ass. When she stepped out and I first saw her, I could feel my cock pulsing in my pants. I had better take my mind off of that night or I wasn't going to get any work done, and I had a few things to on the agenda before I could see Jamie again.

"Hey Mark what are you doing this weekend?" Jamie text.

I knew the day would come when my girl got horny and lonely and wanted to come over for some fun, but I was still really excited that she had come to grips with all this.

"I'm free all weekend baby girl, why you wanna have some fun again?" I texted back already knowing the answer.

"Baby girl?"

"Well you want to come over and be my girl this weekend don't you?"

"I thought we could have some fun again, so... yes, I suppose I want to be your girl this weekend." I bet Jamie hated himself for admitting he wanted to be my girl.

"Well baby, then come over about six o'clock Friday and you better be wearing the panties I gave you."

"Ok I'll see you then, and I will wear the panties under my clothes for you."

Friday arrived and I waited impatiently to hear Jamie's shit box car pull up the drive. I was honey as fuck and couldn't wait to see my girl all dolled up again. At Six fifteen, I heard the loud ass exhaust come to rest in my driveway, and saw Jamie walking up to the door. I waited a suitable amount of time to maintain my cool exterior and make Jamie think I was busy and wasn't excitably waiting for her to arrive.

"Welcome back baby girl, good to see had a good time last time and wanted another taste."

"I guess I did, I had a hard time not thinking about our last time together to be honest." Jamie admitted in a weak voice.

"Well good babe, I'm glad to hear... this is supposed to be a good time, or we are doing it wrong I suppose." I chuckled a bit. "Ok.. now you have to promise to just go along with tonight and allow yourself to just have some fun and go with the flow.

"Ok... I will try to just loosen up and have some fun."

"Excellent, now take off your ugly boy clothes and hand them to me." I demanded.

Jamie hesitated for just a second before stripping down right there in the foyer. Standing there wearing just the delicate blue panties I had given him the last time, Jamie looked so delicious. Passing through the kitchen on route to the bedroom, I grabbed us a couple bottles of wine and some glasses. Jamie followed behind me in her panties looking so vulnerable. When we reached the bedroom, I opened up the wine and poured out two full glasses and raised my glass to make a toast.

"To all the fun we are about to have exploring the road before us." Our glasses clinked together and we both drank deeply.

Now it was time to push Jamie's boundaries just a bit more from last time. I told Jamie how happy I was that she had worn the panties since we had last seen each other and had worn them over to the house, but girls don't walk around with hairy legs. I ordered Jamie to go into the master bath and remove any hair below her eyebrows, and try not to miss a hair. Jamie's eyes grew three sizes and she looked shocked. I directed Jamie to start with the trimmer and then use the razor I had left on the sink. It was a test to see if Jamie would take a step toward femininity that couldn't be washed off when we were done playing. I was elated when Jamie said ok and started to file off toward the bathroom. I playfully slapped her on the ass as she walked away and told her to be quick, we were going to have a busy night.

About 30 minuets later I heard the shower turn off and Jamie emerged from the bathroom as hairless as the day she was born and cock standing at attention. I lead Jamie to the bed and told her to bend over at the waist so I could inspect her work. Eager to comply, Jamie put her elbows on the bed and stuck her pert little ass up in the air for me to view. I worked my hand up and down over her hairless legs as she let out a small moan in appreciation of my attention to her body.

"You did well baby, I like you smooth like this... do you think you will be able to stay smooth like this for me from now on?"

"I suppose so... yes I will try." Jamie stammered.

"You suppose? You will try?" I questioned. "I'm sorry baby that's not good enough, beautiful women don't walk around with hairy legs, if you want to continue this, then from now on you will be smooth." I insisted.

"Ok yes... I will stay shaved for you."

I viewed being hairless as an essential demand in Jamie's path to becoming a woman. I needed to strip away as many masculine things from Jamie's mind and replace them with feminine thoughts and routines. Jamie needed to establish a routine of feminine activities into her normal day to day life, and shaving away her manliness on a regular basis was going to be just the start.

Jamie was still bent over the bed presenting her eager ass to me for inspection when I reached into the top nightstand drawer and procured the medium sized pink buttplug I had bought for this occasion. Jamie's body went tense when the cold lube dripped onto her pink little hole. The plug was a little bigger then a penis in diameter so I was pretty sure she could handle it up her ass. Jamie didn't protest and instead arched her back a bit in an acknowledgement that she welcomed the attention being paid to her backdoor. I slowly worked the lube into the hole with my thumb making slow circles around her pink ring as she started to moan a bit more. when the thumb was sliding in and out freely, I replaced it with two fingers and began fucking her slutty ass with my fingers before proceeding with the plug. My own cock was nearly as hard as Jamie's when the plug started to slowly disappear inside her. precum was leaking from her member as I started to work the plug in and out. I would work the toy into her hole until her hole was at the widest part and hold it there for a few seconds before slowly withdrawing it and starting again. I could tell Jamie was enjoying the stretching her hole was receiving, a dribble of precum attached her erect cock to the bed. When I let the plug settle into her hole and come to rest inside her backside, Jamie looked disappointed that the session was over.

"Good girl, now leave that where it is and go get dressed appropriately while I make us some dinner. I got you some more clothing since your last visit, find something you like and meet me in the kitchen." I ordered as I walked out of the room.

"Oh and I'm looking forward to seeing how you do with your makeup." I called out as I walked away.

By the time I got to the kitchen, my cock was an iron bar in my pants and I was nearly breathless with excitement thinking about Jamie in there, transforming into a sexy woman for me. My mind raced as I wondered what outfit she would choose. I had ordered a respectable new wardrobe for her since our last meeting.Dresses, skirts, shoes, everything a young girl might want. I had to take my mind off Jamie in the other room and started working on dinner.

I was just putting the finishing touches on a nice shrimp pasta primavera when I heard the sound of heels clicking down the hallway making their way toward the kitchen. I knew Jamie was in there preparing herself for dinner but the sound still made my heart race a beat or two. In the door to the kitchen Jamie stood, dressed completely and waited for inspection. She had choose a short black skirt that just covered the tops of her black stockings, a tight purple satin and lace top that strained to conceal the heavy bra within. Her makeup was still a bit rough, but you could tell a lot of effort was made and the eyes were actually very well done. the long blond wig framed her face perfectly and honestly you would never been able to detect any masculinity standing there balanced on four inch stilettoed heels. Jamie had passed the test perfectly and had gone for a slutty secretary look that made my cock hard all over again.

"God darling, you look amazing." The words spilled out of my mouth. "Are you hungry, dinner is just about ready."

Jamie smiled with satisfaction at my approval and I plated dinner for both of us and we made our way to the table. Jamie picked at dinner as we chatted about various topics and made a bottle of wine disappear. finally I had to turn the conversation to more pressing matters.

"So tell me, how does it feel to be dressed like that and look so beautiful, be honest with me."

"Well honestly... it is really exciting and kind of fun. The stockings on my shaved legs is a really trippy feeling , I think I like it."

"I'm so glad to hear that, I like seeing you like this, I hoped you would look good dressed up but I never would have thought you would pick it up so fast and look so good. Any man would be happy to have a girlfriend that looks like you babe." I said with all honesty.

"Is that what I am? Am I your girlfriend now? Jamie wondered aloud.

"Would you like to be? Would you like this to be more then just a come over and get fucked kind of thing?"

A moment passed as I saw Jamie think about what his answer might mean, and how the response might change things. I could see the doubt and insecurity's fighting inside her mind.

"I don't know, its all a little scary... I have a lot of weird feelings at the moment. I find all of this to be so exciting but at the same time it feels weird and I'm afraid what people would say if they ever found out."

"Who are you afraid would find out? I'm sitting three feet from you and I would never guess you were a man. You never had a lot of masculinity to start with and its all gone when you are dressed like this." I said bluntly.

"I suppose you are right, I was never much of a man, but it feels like a giant leap going from a wimpy man to a woman."

"Look baby, I know you have been fighting these thoughts since the last time we got together, but I saw the change in you when we fucked. Your mind switched and you never felt so empowered as when you accepted that you were a sexy bitch and wanted to get fucked like one. Admit it, It felt incredibly right getting fucked as a woman and that's why you have been so ashamed.

"Yes... it felt good to take control and let go of everything and just enjoy the moment, but then I felt ashamed of myself afterward."

"Well, I'm offering you an opportunity to let go of that shame. Let me guide you and take control. If you allow me to be the one in control then the shame isn't on you since you are just experimenting and trying something new and fun."

"I guess it is ok for someone my age to experiment a little and try new things. Nobody could hold a little harmless sexual experimentation against me I guess."

I could see Jamie's mind working things out and creating a cover story where it would be ok to do the things I was going to ask of him and not feel ashamed of letting go of his masculinity. It would all be some experiment and trying new thing except we both knew there wasn't going to be any going back to the way things were at the end of this experiment.

Feeling a rush of power of Jamie, got my erection locked into place and I had to fuck this sexy little secretary slut. I told Jamie to stand up and come over to me. wobbling a bit from the wine and the unfamiliar heels, Jamie made her way around the table.

"Bend over the table." I ordered.

Jamie eagerly complied and her short skirt slid up her smooth thighs and exposed the tops of her sheer stocking to me. The metal garter belt clips slightly pulled the tops of the stockings and framed the picture perfectly. With my left hand I found the base of the butt plug still seated perfectly inside her lubed hole and started messaging it. Purple panties that coordinated nicely with the purple top tightly held the plug in place. It was all too much and I had to fuck her right there at the dining room table.

I hiked up the short skirt into a band around her waist and pulled the panties down to her ankles so she could step out of them and spread her legs further apart. The butt plug looked so inviting holding her ass open for me like that, but it would have to go so my engorged cock could take its place. Carefully I removed the plug and her hole stayed open for just a second from being held open so long. My cock was an oak tree and her open inviting hole was too much, I buried my cock inside her ass and pinned her to the dinning room table. Jamie's hands reached out for something to hold onto and knocked over the empty wine bottle in the process. I started trusting in and out at a torrid pace and Jamie held onto the table and endured my onslaught as best she could. The dishes were moving around the table as the glasses tipped over and rolled unto the floor, breaking as they hit the wooden floor beneath.

This wasn't romance, this was me fucking whatever manhood still existed in Jamie right out of her. With each thrust, I could see Jamie's lust giving way a bit more. She wanted to be fucked hard like this, to feel my manhood inside her bowels as her own manhood disappeared, to be used as a woman by a real man. Her grunts told me that she wanted to feel me explode inside her and in a few moments I was emptying a load into her willing asshole. Jamie let out a loud groan of pleasure as my hot cum filled her asshole.

"Straighten yourself up and clean off my cock baby girl." I ordered.

Jamie pulled her skirt back down and straightened it up before dropping to her knees and gently cleaning cum and her ass juice off my shaft. Cum flooded from her fucked hole and pooled under her as she finished her work of cleaning me.

That was the beginning of something, Jamie had the next three days off of work and agreed to spend the whole time dressed for me. Morning noon and night Jamie was my girlfriend and did her best to make sure there wasn't any cum left in my balls. I could tell a switch had been flipped and wondered where things would go from here. It felt like my plans and fantasies were coming true.