tagTransgender & CrossdressersVacation Transformation

Vacation Transformation


Of course, this is a work of fiction and those knowledgeable in things transgendered will find many flaws in the details of this story. Let them go. It's erotic fiction, not a medical treatise. Although I enjoy BDSM there is none here except that the idea of having one's body transformed in some permanent way seems to me to be the ultimate bondage scenario. Oh yes, and a little bit of hypnotism just for fun.

It was billed as the vacation of a lifetime. One month in Thailand. Bangkok, the beaches, the jungle, even an elephant sanctuary. It was to be the first real vacation I would get since graduation 5 years ago. Since none of my friends could get away for that much time, I had decided to travel alone and bring back a huge photographic record of my trip to make them jealous. But as it turned out, none of that was going to happen.

It was near the end of the first week, when our bus blew a tire and ran off the road, turning on its side as it left the roadway. Luckily, nobody was killed, but several of us were hospitalized with relatively minor injuries. On the morning of my second day in hospital, a nurse entered my room and asked me if I was ready to go. Thinking that I was about to be released, I told her that I couldn't wait to get on with it. Instead of helping me up as I expected, she produced a needle, gave me shot and as I faded into unconsciousness, told me that my dream would soon become reality.

I awoke with an IV in my arm, bandaged from mid-thigh to waist, with a severe pain in my groin. I was totally confused. When the doctor entered my room and looked at my face, he stopped dead in his tracks and the colour drained from his face. He began rapidly shouting in Thai, and when the nurse entered my room, he became even more animated. He shouted something to her which caused her to look at me, clasp her hands over her mouth and run from the room. The doctor rapidly followed her. Not speaking a word of Thai, I was completely confused by the scene playing out before me, but I just couldn't keep my eyes open and drifted off to sleep.

When I woke next, the doctor was standing beside my bed.

"I so very sorry. Nothing like this ever happen here before." he said. "That foolish nurse. She come wrong room. Bring wrong patient. I no see face when surgery. You see?"

"What are you sorry about? What has happened to me?" I asked as a chill of fear gripped me. "I thought I was leaving today."

He started in again "Sorry no. You no leave 'till operation all heal. SRS big surgery, you need big heal time"

SRS. What is SRS? My brain was still in an anesthetic haze. Oh God! SRS. Sexual Reassignment Surgery? Suddenly the pain in my groin made sense and I started screaming like a madman. Nurses quickly ran into the room and sedated me. I never stopped screaming until I lost consciousness.

Coming to, I thought I'd had a terrible dream, but quickly realized that it was all true. I was on some very strong pain medications which made me groggy, so I spent the rest of the next couple days alternating between crying and sleeping. Whenever the doctor or nurses changed my dressings, I stared at the ceiling not wanting to see what had actually been done to me. What I felt when they were working on me was totally different than anything I had previously experienced. Eventually I had to deal with it as I was taught the care and maintenance of my new internal plumbing.

Three weeks after being admitted, I was given a large quantity of pills to "aid my recovery" and was released to take my scheduled flight home. Dressed in my street clothes for the first time I experienced a strange vacant feeling in my boxers and slacks as I walked to my taxi for the trip home. Shelly, my girlfriend, was waiting for me at the arrival gate, and ran to kiss me hello. As soon as she fell into my arms I broke down sobbing uncontrollably. Confused, she asked me to tell her what was wrong and I said we had to go somewhere quiet to talk. Her place was closest, so she said we should get back there.

Not knowing how to begin, I simply blurted it out. The look of shock and horror on her face made it clear that I should have been more considerate of her feelings. When she had recovered somewhat, we had a long talk about my future, and our future. Shelly made it very clear that although she had experimented with other women in college, she was decidedly heterosexual. She liked cock. She also made it clear that she loved me and she would stay with me on a trial basis to see how things worked out.

That night when we went to bed, we cuddled under the covers for a while until Shelly turned toward me and kissed me.

"Oh Chris. I've missed you. Can we just try a little kissing and cuddling?"

I was nervous and scared but I agreed and soon we were embracing and kissing each other. My nipples were a bit swollen and felt quite tender when she rubbed them. Of course I couldn't get an erection, but I did feel a bit of stiffening between my legs. When I told Shelly about this she suggested that we investigate. Before I knew it I was undressed, and Shelly and I were looking at my crotch. Shelly was very complimentary about the appearance of my new sex, saying she thought it would be "cute" once all the swelling finally subsided. She gently probed and stroked it as she talked and in spite of myself, I started becoming increasingly aroused by the new feelings she was causing. Pretty soon I was moaning and squirming around. Shelly stopped and looked up.

"Have you had anything inside you yet?" she asked.

"Yes, they had to insert a series of plugs, they called them dilators, into me every day to make sure I would heal properly" I said. "It was quite unpleasant."

"I have an idea of something we can try if you are willing." Shelly said as she continued to lightly stroke me and press at my entrance.

When I didn't object, she gently pushed me so that I was laying on my back, then opened her bedside drawer and pulled out a penis shaped vibrator and a tube of lubricant. Although it was significantly smaller than my penis had been, it was still a shock for me to see this and realize what she intended to do. A rush of panic went through me and I remembered being told that I had to continue with the dilators and work my way from small to large each time to avoid injury. I told her that and Shelly went to get them. One by one she worked them into me smallest to largest. Finally she had pushed the largest one home.

"Are you OK?" she asked as she started to lube up the toy.

When she was satisfied, she gently started to rub the end up and down my slit transferring the lube onto the inside of my lips. Every few strokes, she squirted a bit more lube onto the end and pressed a bit harder into my sex. It didn't take long before she had slid the toy completely inside me. My previous experience being penetrated had been clinical and quite unpleasant. This was different. I was already aroused by our foreplay, and the thin vibrator stroked gently by my girlfriend actually felt good and added to my excitement. And then she turned it on.

"OH MY GOD Shelly" I moaned. As the vibrations stimulated my sex."That's incredible".

"Really? I'm glad you like it." she replied as she began to slowly stroke the toy in and out of my body.

It didn't take long before the stimulation of the little sensitive nub the doctor had left at my entrance added to the feeling of penetration sent me over the edge into a wild orgasm.

"Don't stop!" I cried. "Oh Shelly. Fuck meeeeee!" I squealed.

When I finally came down off my high, I looked up at Shelly who was smiling down at me. Suddenly I felt ashamed of what we had just done. Of what I had allowed her to do to me. I felt tears well up in my eyes, and I began to cry. Shelly leaned down and embraced me and tried to console me.

"There there Chris. It's OK" She said. "Did I hurt you? Are you hurt?"

"Oh Shelly. You just made me come like a girl." I sobbed. "I'm so ashamed. What am I going to do?"

"Chris" she soothed,, "You used to want sex at least once a day. You can't go the rest of your life without it, can you? This is OK. You had an orgasm. You will be OK."

As her words sank in and her stroking hands soothed me, I started to calm down and realized that she was right. This really was a good thing. No reason to be ashamed. It was the only way I was going to be able to have a sex life going forward. It really was going to be OK.

"Thanks" I said. "Thanks a lot. Now. What can we do for you?"

I have always been an enthusiastic pussy eater, and I was happy to oblige when Shelly asked if I would bring her to a climax that way. With both of us satisfied, we fell asleep in each other's arms and slept deeply until morning.

The next day I told Shelly about my discomfort with my clothing, and asked if she would help me shop for some new underwear to fit my altered anatomy. She happily agreed and let me try on several of her panties to see what style I liked. I tried on several types of her preferred thong styles, but felt worse than I did in boxers. When she gave me a pair of boy short panties. They felt great to me and So that is what we bought. When we got home, I put them on and immediately felt better. But when I looked at Shelly she had a frown on her face.

"Those are cute on you, but those hairy legs really have to go." she announced.

So began my odyessy into shaving my legs. Shelly helped me get everything wet and soapy and then put a new blade in the razor. I had never been particularly hirsute, and my leg hair was quickly removed and rinsed down the drain. Shelly gave me some lotion to keep my skin from drying out, and it felt quite sensual as I spread it on my smooth soft legs. When I put my new panties on and slid into my jeans, I was surprised at how different they felt.

That night, Shelly surprised me with a bigger vibrator. I told her that it looked way too big, but she just laughed.

"It is almost the same size as you were, and you know how many times I took that in me." she said.

To prove her point, she held it pointing out from my groin and told me to look down. Sure enough it looked about right.

"See?"she said, "They always look bigger when you see them from a girl's perspective."

I was still concerned, but that night Shelly made me a believer. I came twice as she worked me over with that toy, and finally collapsed, exhausted, into sleep. Things went on like that for a few weeks, and I was happy with our little arrangement, but apparently Shelly wanted more.

One night after we had enjoyed a fine meal and a little too much wine, we were both feeling quite horny, and retired to bed for some fun. When the lights were out, Shelly stepped out to the bathroom. When she hopped into bed, I felt something poking me from between her legs.

"What's that?" I asked. "What have you got there"

Just another toy, only a little different. That's all" she replied.

Suddenly she was on top of me kissing me and massaging my nipples. I felt something poking at my crotch and when I looked down, I saw that Shelly had a penis. Not a real penis like I once had, but a strap on one like women would use on each other, and it was bigger still that anything I had taken inside me before. I started to protest, but Shelly quickly pressed the head into my hole and before I knew what was happening, she was between my spread legs pumping her "cock" into me. I was stretched tight like never before, and my sensitive nub was being dragged back and forth with each of Shelly's strokes. The kissing, the nipples, the stroking. She kept it all up and soon I was aroused beyond anything I had experienced before. Much to my surprise, I began to enjoy the feeling of being the submissive partner. The "fuckee" as I had always referred to it when I had been a man. Soon I was coming over and over again as Shelly continued to pump into me. Then she groaned, tensed up and had her own orgasm, and collapsed onto me, both of us panting for breath.

"How did you like that?" she asked when we'd had a chance to catch our breath. "I really enjoyed myself."

"Actually, it was great." I replied.

And so it was that as the weeks and months passed. I became increasingly submissive in bed, with Shelly wearing the strap-on and fucking me almost every night. During this time too, I noticed that my body was changing. Without the flood of testosterone, my muscles had atrophied, and my skin and hair were softer. I noticed some swelling and jiggling on my chest and my nipples were becoming larger, darker, and more sensitive. It seems ridiculous that I never realized that some of the drugs I was taking must be female hormones until then. Shelly convinced me to continue on the drugs, and to wear a training bra to control my small budding breasts and hide my nipples. My hips and butt expanded too, and I had to change to women's style jeans and slacks. My hair had become quite long and one day she suggested I have it styled at her salon. When we got home, I was shocked when I looked in the mirror and realized how feminine I now looked. I broke down completely and threw myself down on the bed, crying hysterically.

"Come on Chris" Shelly soothed "There's nothing you can do to change this. Just calm down and come have some wine with me."

Realizing that she was right, and that crying wasn't going to change anything, I decided to follow her to the kitchen where she poured me a glass of red wine. We hadn't had dinner yet so the wine went right to my head, and by the time Shelly poured me my third glass, the bottle was empty and I was in a much better mood.

"Tell you what" she said. "Why don't we dress up and go out for dinner?"

"Dress up?"

"Yeah. I have a great little shift that would look good on you." She said.

And in my somewhat inebriated condition I agreed. Before I knew it, I was dressed in Shelly's knee length shift with only my bra and panties underneath. I had a bit of trouble mastering the 2" heels she gave me and I protested a bit as she did my face with blusher, mascara and eye liner, but soon we were in the car heading to a new restaurant. As luck would have it, the place was packed with a line up at the door. The wine was starting to wear off, and I was just going to suggest leaving, when Shelly's friend Dan and another man I didn't know, walked up to us.

"Shelly! Chris??" he said "Chris. I haven't seen you since you got back. I heard about your accident, but it looks like you are recovering well. You look good. "

I was speechless, but Shelly jumped right in.

"Yes. he's doing much better. This is Chris' first time out in a dress and he's a bit nervous." She replied. I think we need to find a quieter restaurant."

"This is Dennis from our Denver branch. We were just going to catch a bite but now that we met up with you guys, why don't we all just go back to my place and throw some steaks on the grill?"

Shelly immediately accepted the invitation and within minutes, we were in Dan's condo with another large glass of wine. I was so nervous that I gulped mine right down, but being a good host, Dan filled my glass back up again. Shelly and Dennis took their drinks out to the patio, where she filled him in about my accident. Dan and I went to the kitchen to start dinner. Dan started the grill and I searched the fridge for salad. As I was bent over looking in the crisper, Dan moved behind me and reached into the upper shelves for the steaks. As he reached over me, he placed his hand on my hip to steady himself, and as he moved back, his hand slid down over my ass. When I looked up at him, he just smiled.

"Pretty nice view from back here"

I should have stood up and decked him, but instead I felt a rush and started blushing like crazy. I took the salad to the island and gulped the rest of my second glass of wine which Dan immediately refilled. Since the salad was ready, I followed Dan to the grill. Shelly and Dennis were in deep conversation on the far side of the patio and as the steaks sizzled, Dan and I chatted about my new life.

"God Chris. I can't believe this is your first time dressed. You seem to be adjusting well." He said "I just can't get over how good you look." he continued.

The alcohol was really taking effect now, and I became a bit bolder.

"You did more than just look over by the fridge" I scolded. "How did I feel?" I asked blushing wildly.

"Really good" he replied "I'm sorry, I just couldn't help myself. You were showing a lot of leg, and I forgot who you were for a second"

"You're forgiven, just don't make a habit of it" I said wagging my finger at him.

The steaks were done and we all moved inside to eat. Dennis and Shelly sat opposite, with Dan next to Shelly I sat next to Dennis. Dennis asked a few questions about my condition and as I answered, I noticed that Dan was paying very close attention. He was also being a particularly attentive host, making sure that my wine glass never got too empty.

When the meal was over, Dennis and Shelly cleared the plates and headed for the kitchen. Dan suggested we would be more comfortable in the living room. I had lost track of how much wine I had consumed until I stood up and almost fell over. Dan grabbed me by the waist to support me as I stumbled up against him.

"Damn heels" I blurted.

"It's OK"he said "why don't you just slip them off?"

When I stepped out of my heels I realized just how tall Dan really was. I now fit easily under his arm as he wrapped it around me and guided me barefoot to the sofa. I almost fell onto the sofa when I went to sit and didn't notice when my dress pulled up to mid thigh. Dan noticed though, and his eyes locked onto my exposed flesh.

"I better not have any more wine" I said as a rush of excitement passed through me. "I'm getting pretty drunk"

"Don't be silly" Dan replied "Relax, have fun. You deserve some fun after all you've been through" and he filled my glass again.

As we sat and talked, Dan asked some questions about Shelly and I. He wanted to know what our relationship was now and if we were having sex. In my drunken state I told him more than I should have. My dress was still thigh high and as we talked, Dan moved his hand onto my leg and started caressing my thigh. I didn't really notice at first, until he moved to my inner thigh and squeezed.

"Dan. Please stop" I moaned "I don't think I'm ready for this."

Shelly and Dennis returned from their prolonged absence and I noticed that Shelly's make-up was messed and her dress was twisted. Had she been making out with Dennis?

"Can we use the hot tub?" She asked

"Sure" Dan said. "I have a selection of ladies bathing suits in the spare room for just such emergencies."

Shelly grabbed my hand and led me down the hall and into the room. She quickly picked out a two piece suit with thong bottom for herself and a tight Spandex one piece cut high on the hip for me.

"I can't wear this" I objected "It shows everything, and your entire ass is exposed in that thong"

"Don't be silly. Your suit doesn't show anything. It covers you completely." She scolded "and my suit is my business. Now stop being such a party pooper and let's get out there."

The guys had already changed and handed us large brandies as we headed out to the tub. When I pulled my towel off, I thought Dan's eyes were going to pop out of his head. Dennis was also taking great interest in my attire, until Shelly dropped her towel. Dennis and Shelly climbed into one side which left Dan and I together on the other side. Once again, I felt the need to take a big drink to calm my nerves. I noticed Shelly was squirming around quite a bit. Both of Dennis' hands were underwater, and he was smiling widely at Dan. By the time I had finished my drink, the heat, and alcohol had combined to make me almost comatose. I lay my head back and drifted away.

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byArtyGee© 6 comments/ 128254 views/ 71 favorites

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