tagTranssexuals & CrossdressersA Surprise Relationship

A Surprise Relationship


This is a fictional story, although it is based on people I did know. "Tony" and his twin sister "Kim" are based on a set of twins I knew, who were almost identical. I did have a relationship with "Kim" for almost two years, however, the relationship with "Tony" is pure fantasy.

WARNING!!! This story starts with a chapter that describes violence against one of the main characters. Although this story is fictional, I want it to be honest and realistic. Unfortunately, assaults are too common in the LGBT community. Real life isn't a sugar coated fairy tale where crossdressers and transgenders are accepted with open arms, as I see depicted in many of the stories here. I wrote this part to give a background and to set up the beginning of how the relationship between the main characters developed.

If this upsets you, please either skip to chapter 2, or go to another story.


Chapter 1

The annoying sound of my phone penetrated my sleep. I glanced at the clock as I picked it up to answer. 2:48 am. 'This better be a fucking emergency' I thought as I answered it.

"Mr. Lawrence?" The voice was familiar, but it was hard to tell. It sounded like the person was choking and crying as they tried to speak. "I'm sorry. I didn't know who else to call. I really need your help."

"Who is this? Do you realize what time it is?" I asked.

"I'm sorry sir. It's Tony James. I need help. Please, sir."

My still half asleep brain finally clicked in. Tony had been one of my Cadets a few years before, when I had been an instructor.

"Tony! My God! What happened? Where are you?" I asked as I twisted my body out of my bed and grabbed my jeans off of the floor.

He told me that he had been beat up, and was at the hospital, and that the hospital wouldn't release him unless he had someone come pick him up. I told him I would be there in about 20 minutes and hung up.

I quickly removed my breastforms from my bra before removing my nighty and bra (I've been a closet crossdresser since I was about 9), and threw on a t-shirt and socks before pulling my jeans on over my panties.

I arrived at the hospital 20 minutes later, and was told to wait, as the police were still questioning him about the assault.

Tony was in pretty bad shape when I was finally let in to see him. He had bruises, cuts, and scrapes covering his face, his left eye was swollen almost shut, and his neck had bruises as well. It looked like someone had tried to choke him. He had been a very good looking guy when he was younger, with a smaller body and soft, almost feminine, features. He and his twin sister, Kim, were about as identical as fraternal twins could be. But now, he looked like he had been the loser in a 15 round prize fight.

"I'm sorry to call you, sir. But I don't know anyone else in Calgary, and I remembered that I had your phone number," he told me as he looked up and recognized me.

"It's ok Tony," I told him. "But my name is Terry, not 'Sir'. We're not with Cadets anymore.

"What the hell happened?"

"Oh. Hello. Are you Tony's .... friend?" The doctor asked as he came in and saw me.

'Kinda strange how he asked that' I thought before I answered him. "Yes. I'm Terry. I used to be Tony's Cadet instructor. I've known Tony since he was around 12 or 13."

"Oh. OK. There are some special care instructions that Tony will need. My greatest concerns right now are a possible concussion, and internal bleeding. He was beaten pretty badly. I'm also very worried about..." he trailed off, then turned to Tony and asked him "Have you told him what happened?"

"No," Tony quietly whispered, with his head down. This was a lot different than the confident leader Tony had been in Cadets.

"Do you want a few minutes, or should I tell him?" the doctor asked.

"I can't," Tony again whispered as he tried to fight back the tears forming in his eyes.

The doctor turned back to me and continued. "Tony was not only severely beaten, but he was also brutally raped. He has several tears in his anal walls, which have been bleeding. We have treated him as best we can, but he will need to apply an ointment several times a day. We have also given him pain killers, and a stool softener. However, he will need to be very careful taking bowel movements for the next week or so. There will be some blood, but if it is excessive, he will need to come back to Emergency immediately.

"He is to rest as much as possible for the next few days, and should only get out of bed to use the washroom or bathe.

"We've done as much as we can for now. I would prefer to keep him here for a day or two, but he is OK to go whenever he is ready."

"Thanks Doc," I said as I shook his hand. I then turned to Tony and asked "Are you ready to go? Where are your clothes?"

"Oh shit! I don't have any! The police took what I was wearing as evidence."

I ran back out to my Jeep and returned a few minutes later with a pair of sweat pants, a fleece jacket, and hiking boots that I usually leave in there.

"Sorry. Not the greatest, but still better than a hospital gown" I tried to joke with him.

He was very quiet on the drive to my place, other than the occasional moan or gasp of pain. He would only tell me that he was on his way to Vancouver and stopped in Calgary for a couple of days. He had gone out to a club, and when he left, 3 guys jumped him. He passed out from the beating, and when he came to, one of them was raping him. He passed out again, and didn't wake again until EMS was treating him.

He didn't give many details, such as what club he was at, and seemed kind of elusive, but I put it off as shock and embarrassment.

I had him lay on my couch as I went to my bedroom and changed the bed sheets, as well as quickly hid my breastforms and some female clothing I had out. I helped him to the bedroom, and grabbed a t-shirt and a pair of shorts for him to wear. He started to remove the jacket, then stopped and looked at me. I thought he was embarrassed because of what happened and I left the room so he could get changed.

I returned a few minutes later to find him already under the covers. We talked about this and that for about half an hour, until he was starting to fall asleep. He had said about needing his stuff from his hotel, and I told him that if he was feeling ok, I would go to his hotel later to pick up his stuff and check him out.

I slept on my couch, waking a few hours later. I checked on Tony and he was still dead asleep. I made some coffee for myself and played on Facebook for a while before he woke and asked me for help to get to the bathroom. As I helped him, I thought his chest looked a little fleshier than it used to be, almost as if he had small breasts, but it was hard to be sure because of the looseness of my t-shirt he wore.

By afternoon, Tony was feeling ok enough for me to go to his hotel. He still had another night left on his booking, but he needed his clothes and belongings. He wanted to go with me to get his belongings, and tried to insist that he go to his room, alone, to get them. I did bring him with me, but I made sure he stayed in my truck when I went in.

There was a sweet perfume smell in the room as I opened the door and walked in, and I stopped in my tracks as I noticed a bra and panty set on the bed. At first, I thought he hadn't mentioned that he was travelling with a girlfriend, but, as I packed up his belongings, I began to wonder if Tony was also a crossdresser. As I went through his things, I found more female clothes, a well-stocked make up kit, breast enhancers and forms, and two wigs, as well as a few toys. I was now sure he was a crossdresser, and began to wonder if this had anything to do with his being attacked. I was trying to think of how to ask him about it as I put his bags in the back of my Jeep, then went to pay his bill. I thought that he knows what I found in his room, so maybe I'll wait until he's ready to say something.

Tony was quiet on the drive back to my place. I helped him to my couch, and then brought his bags to the bedroom. I was going to help him back to bed, but he said he was hungry, and wanted to stay in the livingroom. I made us some lunch and we ate quietly, until he turned to me and spoke.

"Sir? Sorry. Terry?" he corrected himself. "I need to tell you a few things about my life, and about last night. You're probably going to be disgusted and want to throw me out, but I know you saw my stuff, and I need to tell you about me."

"Tony. Yes, I saw your clothes and other things. I don't care about any of that. And I will NOT throw you out! You are welcome to stay here as long as you need to. The only thing you need to worry about is getting better."

Tony then continued telling me about his life. From the time they were little, he and Kim would try fooling people by dressing as each other. Up until Kim started developing, they looked so much alike that the only way most people could tell them apart was by the way they were dressed. Even after her body developed, they continued to trade places, after Kim bought some silicon breast enhancers, which were almost the same size as her real breasts, for Tony to wear. Because of his short hair, it had been difficult for them to dress as each other while they were in Cadets, until Kim decided to cut her hair short as well. After that, it was easier, and they had even come to Cadets a few times dressed as each other.

He then told me that after Kim had been killed by a drunk driver two years ago, he felt like a big part of his life was missing, and he started dressing as her even more, to the point where he was living mostly as Kim. The only time he was dressed as Tony was when he was at work, and even then he only wore male outer clothing. But, he continued, he had recently quit his job, hoping to start a new life for himself as Kim. He even had all of her ID, including birth certificate and driver's license, and had started taking hormones, which had already given him little 'AA' cup breasts.

Tony went on to say that he knew Kim had been living with me shortly before she had been killed, and that was why he hadn't wanted to try contacting me when he arrived in Calgary. He was going to continue on to Vancouver and try to start his new life there, where no one knew him or Kim. He said that he wasn't gay, but was maybe bi. He never wanted to do anything with a guy when he was dressed as Tony, but he became Kim fully when he dressed as her.

After stopping in Calgary, he had heard about an "alternative bar" and decided to go there. It turned out to be more of a metal bar, and not a gay bar. A couple of guys tried to hit on him while he was there, and before he could leave, they started to grope and grab at him, and one of them discovered the truth about him. He tried to leave, but they followed him out and that was when they attacked him.

He was scared to call me when he was at the hospital, but he said he had no other option. That was when he started to cry.

My heart was torn seeing him cry. I was thinking about my time with Kim, and Tony, even with the bruises and cuts, still looked so much like her. When she was 20, Kim had wanted to try something different and had decided to look for a job in Banff. When she found me on Facebook and realized that I lived in Calgary, she asked if I could help her when she got here. Even though she was 6 years younger than me, I had always thought she was beautiful, sweet, and just a wonderful person (yes, I admit it. I had a bit of a crush on her). Of course I told her yes. As we got to know each other better, she admitted that she had had a huge crush on me when she was in Cadets. Our closeness grew, and she ended up staying in Calgary and moved in with me. She had been with me for almost two years when she was killed by the drunk driver while she was driving home from work one night.

Looking at Tony crying, I was seeing Kim, and I automatically went to him and hugged him, telling him that I was there, and I would make sure everything was ok. I was about to kiss him, and stopped myself, thinking 'NO!! This isn't Kim!'.

The next few weeks were spent mostly together, as I had asked for some time off work. Since the only clothes he had were Kim's, that was how he dressed. I admitted to him that I was a closeted crossdresser, and that Kim had known, and accepted it. We became closer, and it became harder for me, as I saw Kim every time I looked at him.

After the visible scars healed, we would go out with him dressed as Kim. Watching his recovery, and seeing him becoming Kim more every day, I found that my feelings were getting stronger and my attraction growing. Not for Kim, but for the Kim version of Tony. They were so much alike. The looks, the personality, even the little gestures and movements I remembered Kim making. Other than his body, Tony was Kim as much as he could be. It was so hard for me at times, as I was constantly fighting my feelings. It was confusing to me as I found myself falling in love with Tony as Kim, and I had to keep reminding myself that this was not my Kim.


Chapter 2

It was now late May, and two months had passed since the night I had received that phone call from Tony. The scars had heeled so they were almost no longer visible, and a little bit of make-up hid them completely. He had an appointment for a full check-up, but he needed to go to it as Tony. We found some of his male clothes that still fit him (he had lost almost 20 pounds), but he needed to buy male underwear, as he hadn't worn any for several years. We managed to find some red nylon boxer briefs, which he said were almost the same as boyshorts, and felt almost as good as his panties, except for the fit of them. Because of the different medications he was taking after his assault, the doctor had recommended that he stop taking the hormones, as they could have caused adverse reactions. As a result, his budding breasts had not only stopped growing, but had completely shrunk back to a normal male chest. He also needed to shave and remove his body hair more often.

The doctor gave him a complete examination, including anal and prostate exams, and also gave him the results of the STD and AIDS tests they had given him. All of the tests had come back negative, and he was given a clean bill of health. He was told that, other than a few small scars, he was completely recovered. He also said that Tony could resume taking the hormones, if he wanted to. Of course Tony immediately said that he did want to, and the doctor wrote him a prescription, as well as set up a series of appointments for hormone shots.

We decided to celebrate his recovery, and I made reservations for dinner Saturday night at a very nice restaurant. Tony was very excited, as this would be his first opportunity to be all dressed up since the assault, but he needed to go shopping for something nice enough to wear. Whenever we had gone out with him dressed as Kim, he had been dressed casually in jeans or a denim skirt. He had been letting his hair grow, and it was now down below his shoulder blades. He said he needed to go to a salon for a haircut, as well as a manicure, as his nails had also gotten longer.

Saturday morning, I dropped him off at the mall, in his usual casual Kim clothing, and surprised him by handing him my credit card, telling him to buy whatever Kim needed. I also let him know that I had made an appointment for Kim at the salon in the mall at 2pm, and that it was for "the works", and they already had my credit card number to charge it to. He was so excited that he surprised me by leaning over and kissing me on my cheek before jumping out of my Jeep and hurrying into the mall.

Tony called me just after 4, asking if I could pick him up at the mall on the way to dinner, rather than taking him home before heading to the restaurant. He said he had found the perfect outfit to wear, and he wanted the salon to do his hair and make-up to be a perfect match to it. I agreed, and then called the Town Car service I had booked to see about rescheduling my pick up time so we would have enough time to stop at the mall before going to the restaurant.

I phoned him as we were on our way to the mall and let him know which entrance to meet the car at, as there was a drop off and pick up zone there. We were there several minutes before I saw a woman carrying several bags come out, followed by another woman carrying several more bags. I stared at her for a few seconds before realizing that this gorgeous woman was Tony! As I got out of the car and the driver popped the trunk open, I couldn't believe the makeover that Tony had had to turn him into an even more beautiful woman than Kim had been. This vision of beauty before me had no signs of being Tony anymore. This was the most beautiful woman I ever remembered seeing.

My eyes travelled up her 5'7" body, from the strappy 4" heeled sandals, over the shiny black Cuban heeled seamed stockings covering her calves, to her knee length black halter dress. The dress was form fitting, showing off curves that I never would have believed Tony could possibly possess. Feminine hips narrowed to a small waist, leading up to the cleavage of perfect 'B' cup breasts, which was very nicely shown off by the V cut front of the dress. Her makeup was a perfect look for an evening out, with smoky dark lavender eyeshadow, and matching lipstick, as well as matching polish on her toenails and fingernails. Her light brown hair had been layered and trimmed to just below her shoulders, and had a slight soft curl to it, and she wore dangling earrings that framed her face perfectly.

The driver and I quickly took the bags from her and the other woman (an employee of the salon, who had offered to help Kim with her bags) and placed them in the trunk before I turned to her and looked at her again. She did a slow 360 turn, showing off her outfit and body to me, and everyone else nearby, before stepping gracefully over to me. She took my hands in hers, looked softly into my eyes, and asked if I liked how she looked.

I was speechless as I again looked at her from head to toe, and then back up. Staring into her smoky hazel coloured eyes, I no longer saw Tony or Kim, but a beautiful woman before me and my answer was to pull her against me as my lips met hers. I felt her arms go around me, and she sighed as we shared a kiss in front of all these people. I broke the kiss as the thought that this was Tony went through my head, although my eyes told me different.

I helped her into the car, and we talked on the way to dinner. She had decided that it would be best if I didn't call her Kim, but instead use Kim's middle name, Anne. The restaurant was an old farm house that had been restored, and we each had several glasses of wine with our excellent meals. The town car was waiting outside when we exited, and the driver helped us take Anne's bags to my door from the trunk when we arrived home. We left all the bags on the floor, and Anne sat on the couch as I poured us each another glass of wine before I sat next to her.

She removed her shoes and started to rub her feet, saying they were sore from all the walking around the mall, as well as her not being used to wearing heels anymore. She then twisted around and placed her feet on my lap, asking me if I could give her a foot massage. I slowly rubbed her feet through the delicate stockings for a while, before my hands started massaging her ankles and lower calves. Her eyes were closed, and she softly sighed and moaned as she whispered how good it felt as my hands made their way up her calves to her knees, then slowly back down to her toes. My eyes were locked on her face, and I only saw this gorgeous woman before me. She opened her eyes to reach for her glass of wine, and saw me staring at her. She took a sip of wine and placed her glass back onto the table before she leaned towards me and returned my stare. I couldn't help myself, and I leaned towards her, kissing her soft lips as my hands moved up her legs, over the top of her stockings and felt the bare skin of her thighs. Her arms went around my neck and she pulled me tighter against her as her lips opened, allowing our tongues to touch and tease each other.

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