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Travel is involved in the work that I do. I don't mind the travel, the work is rewarding but it does have an impact on my personal life. At 32 years old I am still single and haven't dated all that much. It's really hard to meet someone and build a relationship when I am gone so often. Yes I do have friends but most have started to settle down and as I've grown to realize that single people and married people don't spend as much time together as you did when you were all single. That's life. People come into your life and leave it, sometimes not in a noticeable way. Often you don't realize that the last time you saw someone was going to be the last time you'd see them. Then something would happen and you'd realize that person had left your life and cases you had no idea what happened to them. This is one of those cases. On a recent trip to another state I had finished up at a customer's site and had the rest of the day off, I was traveling back home the following day (Friday). As I was driving back to the city I noticed I was getting hungry and looking at the time decided I needed a place to stop and eat. Taking the next exit I found a little local place that looked appealing and pulled in. Now going to a restaurant alone used to bug me, since you typically see people eating in groups but I've gotten over that a while back and besides I had my iPad along and could at least read the news. Walking inside I asked for a table for one and was lead to a seat by the windows. After sitting down my waitress came by to ask if I would like something to drink while I looked over the menu. Looking up I asked for a diet coke. For a moment I thought I recognized the waitress, and for some reason I thought she had a moment where she felt the same. Looking at her name tag I saw that her name was Cindy. I thought hard but just couldn't remember knowing a woman named Cindy. Cindy brought me my drink and I ordered my lunch. I pulled out my iPad and started to read the news but kept on looking up for Cindy trying to think where I knew her from. Several times I caught her looking at me but when I looked at her she quickly looked away. Now I knew that something was up and even though I couldn't place her I felt that she knew me somehow as well. As I finished up Cindy brought over the bill. I pulled a card out to pay for it and noticed that she took a long look at my card, and likely my name. As she walked away to process the bill I once again caught her looking my way and then looking away, now with a more concerned look on her face. When she came back with the receipt I finally told her that she looked familiar to me but I couldn't place where we might have met before. She stared downward and then told me that she had felt the same but then knew for sure once I had given her my card. I asked her from where we knew each other. Her reply was that she would prefer not talking about it here at work. A little perplexed and wanting to quench my curiosity I asked her if we could meet once she was done at work. Nervously she agreed and said she was off in an hour and could I give her some time to go home to change and freshen up. I had no problem with that but asked how would we meet up? She asked if I had a cell phone, which I did and then gave her my number. Upon leaving I called my travel agency to change my travel plans. Rather than driving all the way back to the city I asked that they find me a place to stay in the town I was in and also to change my flight back home to Sunday evening. With the changes made I entered the address into my GPS for the hotel, drove there and checked in. Since I had some spare time on my hands I also took time to shower and freshen up a bit. About 4 my cell phone rang and it was Cindy. She asked if I was ready and I said that I was. Still in the back of my mind it was driving me crazy not knowing where I knew her from. She asked that I stop by her place to pick her up and we could go someplace private to talk. Arriving at her apartment building she came out and got in my car. I told her that since I didn't know this town she'd have to direct me to where ever it was that we were going. She directed me to a park with a great view of the river. We parked and Cindy got out, I did as well. We started to walk and then sat down on a bench facing the river. Cindy then told me that yes we did know each other years ago, but I still couldn't place her. She then kept talking and said that we had gone to high school together. Still nothing. Then she said that her name changed since high school. I dummy me asked if she had gotten married and changed her last name, then it hit me, I still didn't know Cindy's last name. I think she could see me trying to process out what was all being said then it hit me, like a ton of bricks, Cindy was a classmate of mine named Dave. But Dave was a jock, a man's man. He wasn't an ass like so many of the jocks but still he was a jock, a Mr. Sportsman through and through. But now here before me was a woman named Cindy telling me who she was and I was stunned. Staring down at the ground Cindy then started to cry and I didn't know what to do. I mean I've never had something like this happen to me before and never in my wildest dreams ever thought out ahead of time what I would say in a situation like this. Not knowing if this was the right thing to do I put my arm around her should and let her lean into me and told her it was alright. She must have cried for 20 minutes. I told her not to worry about me, that she didn't have anything to fear from me. We walked silently some more then found another place to sit again. Cindy then told me that she had been away from everyone she ever knew that she almost felt like she was dead to the world. Seeing me back in the restaurant made her first fearful. She then realizing who I was and at least remembering in school the type of person I was she then felt the need to be able to finally talk to someone. Cindy told me that after high school she had gotten a baseball scholarship at a college in this state. Her first two years were great. She did well in school and on the field. She thought she had the world at her feet. Then she met a lady named Christina, who was 10 years older than she was but a real classy lady. As they got to know each other more Cindy found that Christina had a real kinky side to her and was actually into being the dominant one in the relationship, wanting her to be the submissive one. She thought that she was game for a little sexual play. As time went on Christina started to play dress up with her new toy, and Cindy just got sucked into it more and more. First Christina wanted Cindy to be less hairy as she put it and was scheduled into a salon for a full body waxing. Since baseball season was over Cindy felt that she could always grow out her body hair before she had to hit the showers again with the boys. Later on Christina then asked Cindy if she really wanted an experience to remember. Cindy was by now very open to Christina and agreed. She then said rather than going home for the summer that she should stay and have fun being her girlfriend all of the time. At first the sexual experience was great but then Christina pushed it up a level and introduced her to her strap-on. Cindy at first admitted it was painful but eventually found it pleasing and even started to achieve orgasms with it. Christina once again took it up another notch. She asked Cindy if she really wanted to experience something wild. By now Cindy told me that she was very vulnerable and agreeable to almost anything at that time. Christina then dropped a big one on Cindy and asked her if she had ever heard of Depo-Provera. She replied that it was a female contraceptive. Christina then said it was some much more than that, especially when used by a genetic male. Cindy admitted to me that deep down she knew she should have left then and there but was too far gone. Christina told Cindy that she was going to make an appointment with her doctor for a physical, consultation, and perhaps a shot or two. Christina told Cindy that she needed to go dressed as a woman, that her doctor already "knew" she was a transgendered. Christina told her to just say that when they went. After the physical, and a clean bill of health came up, Cindy's new doctor left the room for a while coming back in with a tray and some papers. She sat in front of Cindy with the papers explaining what they were for. Once was a consent form to allow administering of Depo-Provera, the others were basically state that she had consented to and knew full well all of the effects that he drug could or would have on her, as long as she took it. Cindy said that she signed each without really reading them. The doctor then had her stand up, and lean over the examining table. She lifted her skirt up, pulled her panties down exposing her cheeks then turned to the tray she brought in. She dabbed a cotton swab on some alcohol and wiped an area. The doctor then picked up a vile with a milky liquid inside and taking a needle withdrew an amount, turned, and stuck it in Cindy's one cheek. As the doctor pressed it in, Cindy told me that she started to feel an almost low burning feeling in her body. The doctor told her to have a seat again, pulling up her panties. Before Cindy knew it she had started chemical castration regiment. Christina was thrilled with Cindy as they left. Cindy told me that she was very emotional for remainder of the day and for the week had problems with crying spells as well as mild headaches. By the time the week was out Cindy told me that she no longer was able to get an erection. By the end of the summer she also said that her balls had started to shrink as did her penis. Her muscle tone also went away, she gained about ten pounds but not all over, it was mostly in her hips and butt. Baseball season was starting up and Cindy told Christina that she had to start dressing once again as a boy. Christina reluctantly allowed her to. When Cindy went for the first day of practice she told me that she found more than one team member looking at her oddly. Cindy told me that "Dave" was a pitcher. When "Dave" went to the mound, wound up and pitched a fastball to the plate, it fell short, really short, about ten feet short. Someone yelled hey "Dave" you threw like a girl. Now try pitching a real fastball this time. "Dave" tried and no matter how much he tried he couldn't get it to the plate. The coach was furious and had "Dave" follow him to his office. He asked "Dave" outright what was going on. Was he on some illegal drugs? "Dave" of course said he wasn't. That's when the cup came out of the Coaches desk and was given to "Dave". "Dave" went to the coach's bathroom. He locked the door, unzipped himself and pulled out his penis, or really what was no left of it. As "Dave" held his penis with two fingers he filled up the cup, put the cap on, and before putting himself back in looked ahead at the mirror in front of him and saw that his penis was now tiny compared to what it should be. Leaving the bathroom, he gave the sample to the coach who then told him he was suspended from the team until the tests came back. The test did come back and it did have a positive result, not for anything illegal. It did find that he tested positive for a birth control drug, a female drug. The coach asked him about it and "Dave" admitted to taking it but tried to tell him it was prescribed by his doctor. The coach told him that by the rules of his scholarship he was to immediately inform the program and any legal drugs he was taking and that if they did affect his ability that the school could and likely would withdraw their scholarship from him. That's exactly what the school did. Since "Dave" had no means to pay his own way through college he found himself out of school, and likely now never having the opportunity to play pro-ball. "Dave" (Cindy) went back to Christina's house, since he/she lived there now. Christina consoled her and said that she should take a shower and wash away her day's sorrows. When "Dave" (Cindy) came out Christina was there and walked her back to the bedroom. She got "Cindy's" clothing out, putting "Dave's" stuff away. Helping Cindy dress she then took her hand and led her to the car. Christina drove not paying attention to where they were going. They go there and Christina came around and helped Cindy out of the car, they were at a solon. Once inside Cindy was lead to a chair and given the works. Her hair, and nails were done but this time they also gave her a facial and proceeded to shape (pluck) her eyebrows. Cindy told me that she looked positively "girly". Dave was gone and she knew it somehow at that moment. After words they drove to the doctor who had Cindy sign some more papers and gave her more injections. Cindy told me that she now was taken off of Depo-Provera but was now on strong female hormones. She remained impotent, her testicles still seemed to be shrinking but at least her penis stopped short of disappearing. Within a few months Cindy told me that her chest started getting puffy and that her breasts started to sprout. I asked Cindy why didn't she just leave and go home once she lost her scholarship. She said she couldn't go home like this. By now she said that her emotions were no longer in check as they should be as a man. He also started acting less masculine after the summer with Christina. In January the year after she was out of college Cindy told me that she started to have pain in her groin area. Her doctor told her it was her testicles. Upon further examination was told that they would have to be removed. Cindy was devastated. Cindy also told me that Christina was thrilled. The next morning Christina drove Cindy in for her bilateral orchiectomy (actual physical removal of her testicles). Cindy told me that she surprisingly was almost relieved that the pain was gone, but so were her testicles. She was no longer was a "he". Christina seemed to relish in her new girlfriend, and when they got home Cindy realized that Christina had thrown away all of her male clothing. Not a pair of slacks in her closet, not ever women's slacks. Several months later Christina brought up another topic. She told Cindy that she wished her breasts were bigger. Cindy thought they were large enough, but knew that what Christina wanted, Christina got or rather this time Cindy got. What she got were 700 ml breast implants. Trust me here I am sitting listening to Cindy telling me about how she got from being a high school jock to now living as a castrated male with breast implants and all I could think of was in a way how sorry I was for her. Cindy told me that as time went on she really missed being back home and missed her friends but now felt it impossible to go home. Two years later Cindy told me that Christina was diagnosed with cancer. She put up a good fight but eventually lost her battle. The mounting medical bills forced the liquidation of Christina's assets (mainly her house) and essentially died penniless. Cindy told me that all she could find for employment was the job as a waitress. That at least put a roof over her head and food on her table but not much more. I told Cindy that is was just by chance that I stopped in the restaurant and that I was here in business. I too no longer lived out hometown, but lived several states away in Florida. I asked Cindy had she ever thought about going back to college to get a degree. She did but no longer had the means to do it. That's when I said something that even surprised me. I asked her if she could use a change and a chance for a way out of this town. Cindy said sure but that's never going to happen. That's when I suggested if she wanted she could fly back with me and starts over in a new place, that I would help her by her sharing my house for a while. Cindy said it's tempting. We got back in my car, drove into town and I took Cindy out to supper. I dropped her off, she actually kissed me on my cheek then realizing what she did apologized. I told her that I was as surprised about the kiss as she was and not to worry. We met again on Saturday and spent the whole day together. She asked me again if I knew what I was getting myself into. I said that I did. But Cindy was insistent that I follow her inside her apartment. When we got up inside she then said that before she would drop this life and fly back with me she needed to know it would be alright living with someone like her. I started to talk and she placed a finger over my mouth and said she needed to know for sure if I could really live with her, the real her. And with that she said for me to sit, and she went into her room. A few minutes later she came out in a robe and sat down next to me. She told me that she had undressed because if we were going together (even though it's a platonic relationship) that the chance existed where I would see her naked (and she see me). Since she said she's seen me naked before (we did have senior gym class together) she pretty much had seen it all before. But it was important to know that I would be ok should I see her and asked if it were ok to disrobe in front of me. I know I choked out an answer. Cindy got up and undid her robe, setting it on the couch next to me. There she was standing in front of my, all the curves where they should be, firm breasts, and then I stared at her penis. Or better yet what was left of it. Her penis was now very short, about two inches, not big in diameter anymore, and then her ball sack below was now soft, hairless and most certainly empty of the testicles she was born with. My god I never thought back in high school that one of my classmates from gym class would be standing here in front of me looking like this. I then noticed I had gotten a hard-on, like nothing I had ever had before. Cindy noticed it too. I wasn't expecting this to be my reaction. It didn't subside either. Cindy asked if I'd like her to take care of it. I didn't know what to say. Cindy proceeded to unzip my pants and take my penis out. She started to rub it up and down and while doing so started to ask me why I got so hard. I just said I found her attractive, really attractive. She asked what I found attractive, I said everything. She said that I knew that deep down that under it all she was born a male. I understood but still said I found her attractive. Cindy then proceeded to lower her head down and took me inside her mouth. She gave me the most explosive orgasm I ever had. It was the best blow job I ever had; actually it was the only one I ever had. I then asked if she were able to orgasm. She said yes but hadn't in a long time. I quite honestly asked her if she couldn't get hard anymore how she could achieve an orgasm. Cindy replied that Christina had trained her to orgasm through anal stimulation with her strap-on, which she used often. Cindy said she was curious if she could orgasm with a real cock but had never tried it. She said to remember that she didn't seek out this life but now that she was in it, with no turning back, she had opened herself up to possibilities she once thought were wrong. I admitted to her that I found the thought of bringing her to climax attractive but that would happen for a while since she just sucked me dry and it would take a while till I could get it up again. She joked that she wished she could say the same thing. We both started to laugh. Cindy turned on the television and we watched something for about an hour. She sat next to me and against me, still naked. I found my arm around her shoulder and down the other side. I found my hand start to wander a bit and found myself rubbing her right breast. When I caught myself doing it I started to apologize and she said it was ok. She then started to play with my penis that was back inside my pants. I found it once again growing inside. Cindy had a smile on her face and she then said that is something she really misses being able to do herself. Rather than putting a dampener of things she got up and asked me to follow her into her bedroom. Inside she started to undress me and had me lie down on the bed. I told her I had never done it this way, she said neither had she but we'll figure it out. The one thing that Cindy told me was that if I wanted to go through this that I had to use lubrication and that she had some. She opened her nightstand drawer and pulled out a tube of KY jelly. I spied a dildo also inside the drawer. She pre-lubed my penis and we started to make out. Things were getting hot when Cindy told me that she could take it one to two ways, either on her back or on her hands and knees. She said she'd rather be on her back. Let's just say that Cindy had a powerful orgasm and thanked me profusely. She said she wasn't able to ever bring herself to having one and since Christina's passing hadn't had any sex with anyone else. I also was her first man. I admitted to her that I had never been with anyone ever so man or woman she was my first anything, a night of firsts. Sunday morning I called into my boss asking if I could take a few days off, and she agreed. I told her I'd be back on Wednesday. Cindy and I talked again about her moving away with me and we both agreed it would be the right thing for her to do and me as well. She stopped in the restaurant and told them that she was moving immediately to Florida, she had met someone from her past and wanted to be together again (not quite the accurate truth but close enough for their sake). Monday morning I helped her pack her things, also a piece of luggage for her to take a few changes of clothing along till her stuff showed up. A moving company had one of those drop-off type boxes that you could put your stuff in and they'd move it to your new location. Putting a lock on the box, Cindy turned in her keys to the super and we left for Florida. When we got to the airport and went up to purchase her ticket is when I realized that I didn't know about her ID. I asked her about it and she said that she had legally changed her name to Cindy so there was no worry about that, but that her sex was still listed as male. We walked up to the counter to purchase her ticket. The ticket lady asked for ID, which Cindy gave her, she then typed in the information and printed out a ticket and tag for her back, no questions or comments. We were told to take our bags to the TSA people and preceded to our gate. Security was my next concern. As a frequent traveler myself I know what to expect but with Cindy I didn't know what was going to happen. I told her not to lie about anything. There's no law that states what she's doing is illegal. The screening officer took our tickets and ID and told which line to go down. Off with my shoes, I told Cindy she needed to do the same. I walked through the body scanner, no problem. Cindy was next, no problem. We collected our things, I put my shoes back on and Cindy put her high heels back on. We proceeded to out gate and waited till boarding. Since I had upgraded my ticket to first class and bought Cindy a first class ticket as well we had seats together. The flight lasted two hours, and I (we) were home. I showed Cindy a room that she could have all to herself, and showed her mine. While I call my house a house it really is part of a sprawling condo complex in a gated community. Not a well to do mansion but quite a comfortable place to live in. I told her that I bought this one because of my frequent traveling I could never keep up with yard work. Over the next month Cindy's things showed up and she unpacked. I traveled a few more times, but no really long trips. Cindy found work at a FedEx sorting facility that allowed her to make a living but important for her allowed her to have health insurance. Since Cindy's hours were in the middle of the night, she was home during the daytime. She told me that she wanted to have a visit with a doctor to discuss her health. Not being from the area she asked if I had any suggestions on who to go see. I told her my doctor's name and gave her his number. She called and made an appointment for a visit. Cindy told me that before she visited she requested a phone conference with the doctor to fill him in on some of her details. Her visit actually went well though she told me that the doctor told her that she would never be able to function as a male again not because of her testicles being removed but rather her penis had atrophied to such an extent it could never recover. He did ask her about taking things the other way, as in going for a full sex change. She told him that she would give it some thought. I found that Cindy and I talked a lot of her having SRS. She told me that before she met Christina she never had any thoughts of being a woman but now without any testosterone flowing in her, and her on female hormones for so long she really thought that this at least would allow her to be a whole person rather than two halves. I told her it was her life and she needed to think it through first before making that choice. Two months later I drove Cindy to the hospital. Normally I guess one has to live in their desired gender for at least a year. Cindy had been living and working as a woman since leaving college. With the documented proof, there was no one year waiting necessary. Cindy's surgery went well, she was a little sore for a while but she was a real trooper. I can't imagine what she's gone through to get to where she is today. Recently I got a call from back home from one of my cousins. We were talking about everything in general. She told me that a friend of my aunt had her husband pass away a month ago. She said I might remember him... it turned out it was Cindy's father. My cousin said it such a tearful funeral. Their only child, their son, had disappeared years ago and she was all alone. I didn't want to concentrate too much on this subject but asked a few more things, telling my cousin I remember him from high school. I then asked how the rest of the family was doing. I stayed up late that night. Cindy of course was back to work but didn't get home till 3 in the morning. When she came in she was surprised to see me still up. I asked her to sit down I had some news. I told her of my conversation with my cousin and the news about Cindy's father. She cried, saying how she missed her parents so much but could never do this to them. I told her that you know your parents are your parents. They love you no matter what. Now that your father is gone perhaps it is time for you to contact your mother. Give it some thought. Two days later Cindy called her mother up and had a long conversation. I didn't snoop in on her conversation but it lasted at least two hours. When Cindy came back in the living room I could tell she had been crying since her eyes looked puffy. I asked her how it went. There was a long paused and she then said it went surprisingly well. Her head went from a bent position to straight up at me with a smile (not an ear to ear grin but a smile). Cindy looked relieved though she also looked drained. Cindy and her mother talked several more times together. Cindy asked how I would feel if her mother would come for a visit. I told her it was fine with me, we had plenty of room. A little over a week later both Cindy and I went to the airport to pick up her mother. I could tell Cindy was nervous, I was nervous for her as well. As the people passed out of the secured area Cindy spotted her mother and broke down crying. Her mother spotting Cindy (and me) ran up to her and started hugging and crying as well. Heck even I started to tear up. I carried her carry-on bag as we walked to get the rest of her luggage. Once she had everything walk to the car and drove home. Cindy's mother knew who I was, from high school days even though "Dave" and I weren't really "friends" in high school. She thanked me more than once for being there for her. She knew we were just friends now. Neither Cindy or I ever told her that we ever had any sexual relationship between us (even though it was only the one time when we first met). Cindy and I had a closeness that I think we both feared could be lost if we got close sexually again. Cindy did go back to college and got her degree in computer technology. After getting her degree she applied for a more appropriate job (to her degree) as FedEx and got it. That allowed her to work normal daytime hours. Around that time I also left my traveling position for one in management that allowed me to stay home more. As time went on we stayed very close and it almost seemed as though we were about to part ways again. Cindy asked if she could take me out for dinner one night. She drove to a really nice restaurant and we were seated. She started our long conversation that night. It began at our beginning and lead to us sitting where we were. She then said that she really loved having me in her life, I said the same. She admitted to me that she had felt a sexual attraction since we met but didn't want to screw things up. She also said she never knew where it could go given her past. I took her hand and looked in her eyes and said that since we first met she had changed my life too. I was thankful to there for her when she needed me and that I didn't want to mess things up with her. I valued friendship her too much screw things up. She leaned over and gave me a kiss. She looked very beautiful that night and I found that I didn't want her to leave me ever and told her. I then said something that I know deep down I had felt for some time I asked her if she'd marry me. Oh did I get a big hug. It was only after six on a weekday and I asked her if she'd come with me. We flagged our waiter down for our bill. Once back at the car I asked Cindy for her keys. I drove us downtown to a jewelry store I had bought a necklace for Cindy when she graduated. Inside I asked to see their wedding rings. We looked and found a beautiful setting. I asked to see their un-mounted diamonds. I found a really nice flawless 1.5 carat diamond. Our jeweler said he could have it ready in an hour. It looked stunning on Cindy's finger. That night Cindy and I slept together for the first time since we first met. It also was the first time we had sex together as a man and a woman. After we had our fun Cindy told me that I was her first man ever as a woman. I told her the she was the first woman I have ever been with. Cindy made a lovely bride; her mother was there of course as were some of our families. They all knew enough about things but not all the details. Today Cindy and I are extremely happy I was hungry on a trip and recused her. She's told me that she never thought her life would end up this way being married to a man, wearing dresses and high heels but that she's glad things worked out this way. I can say that I agree with her.