at the crossroads

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Status: In Progress  |  Genre: Non-Fiction  |  House: Booksie Classic

this is the story of who i am and how i got to where i am today

The story you are about to read is true. Names have been left out to protect the innocent.

My life feels like it is at a crossroads. I am married to a woman I have known and loved on a level most would not understand since we were 10 years old. We always loved each other but it wasn’t until 30 years later we got together romantically. Oddly enough, it was about this time I began crossdressing. Even before I put on my first pair of panties, I always felt somehow I was different. All of my friends were always girls. I never played with GI Joe or trucks. I also didn’t play with Barbie.

It all started around 8 years old. There were times after school I would be watched by my mother’s cousin. She seemed normal enough although she was always kind of the black sheep of her family. The first few times I stayed with her were fine but it may have been about 6 months in that things started to happen. I always had a sandwich after school and one day she brought out my snack but she was dressed in just a robe. I figured she was going to shower or change or something.  She sat down next to me while I ate and she had loosened the robe and her breasts were clearly visible. Of course I looked. I was a boy and even at that age I knew what boobs were and was fascinated.

After I ate, she asked me to go with her and I followed her to her room. It was there she removed the robe and got on the bed and asked me to join her. I was nervous but I went. I remember her talking to me but really, all I could do was look at a naked lady in front of me. She said she wanted to play a game and undressed me from the waist down. She told me this had to be a secret and not to tell anyone. I kind of knew that this was wrong but again, I was an 8-year-old boy and curious.  I won’t go into graphic detail but as you can imagine, I was introduced to a woman in the most intimate, if not disgusting way.

The summer was almost there and I only went there one more time and nothing happened but she asked me if I was keeping our secret and I said I was. I had turned 9 and over that summer I noticed as I would explore myself that I was getting hard down there when I did. To me, this was a new toy and I explored it often. I pretty much forgot about what had happened and started back to school that fall.

I was told that I would be going back to my mom’s cousin every other week and said ok. The first time I went after school, she was in a robe again. After my sandwich, I pretty well knew where we were going and followed along. This time was different though. The first time it was about me doing things to her. This time when we were naked, she started touching me and I got stiff right away. She played with me for a while then asked me to do the things I did last time, reminding me of our secret. It didn’t really bother me that much but I knew it was wrong because I had to keep it a secret. After I got home, I would go about my normal activities but at night I would always pleasure myself until I got that good feeling again.

It may have been about a month into the school year when I went to her house and she was not alone. Her boyfriend was there too. She told me that he would be joining us and not to worry about it and that it was very important to never tell anyone about him.

That time I did not enjoy things. He did things to me that I never knew were possible. I didn’t really like what he did but, I was a good boy and did as I was told and never said a word. I felt dirty and I knew enough about sex that it was supposed to be a man and a woman. I didn’t know anything about homosexuality at that age.

The next time I was alone at her house with her, I told her that I didn’t like it when he was there and I told her that it made me feel bad and sex is supposed to be a man and a woman and she told me she had a way to help me feel better about it. We didn’t do anything but watch cartoons that day.

A couple of weeks later, he was there again. She told me to follow her into her room. I went in her room and she closed the door and sat me down on the bed. She told me that she could help me not worry about things and brought out a girl’s outfit complete with socks and panties. She told me that I would wear them and everything would be ok. I did as I was told and let her dress me as a girl and let him in the room. Secretly, I loved her dressing me like that as I had always wanted to dress as a girl.

Even though I was wearing these things, I was not a girl and didn’t like doing what he wanted but this time, he did things that made me feel good and was more focused on making me feel good than he did last time. I feel disgusting even to this day about it, but I actually enjoyed the way things felt.

After January of the next year, my stays at her house afterschool stopped for a long while. My grandmother lived next door and she was getting over her medical issues and was able to take care of me.

It was probably close to 2 years before I went back there after school. I was older, and knew more about sex and was finally having real orgasms at 12 years old. Even though I felt old enough, I had to go back to her house after school. I had a little sister and she needed too much attention from my gram to have me around on the days we would be home alone.

The sex started again as well as dressing me as a girl and being older, I was all in. I may have been 12 but I had the mind of a 20-year-old. I knew so much about sex. Every opportunity I had, I took to learn about it, I took advantage of. There were adult books hidden in the bathroom closet that I read cover to cover many times, absorbing every bit of sexual act possible. I remember feeling sexy and pretty when she would dress me up and above all else, I loved that feeling.

The molesting never bothered me mentally but to this day, I have nightmares about it. Usually, the nightmares are worse than the actual memories. Am I blocking some things out? It’s possible but the subconscious mind never forgets. I always knew it was not my fault and there was very little I could do about it. I probably could have said something about what she had done but when he got involved. I was too embarrassed to say anything but inside my head, I never let go of being dressed as a girl.

I finally stopped going there at the end of my 12th year. I was happy my parents allowed me to be home alone after school being almost 13. I was happy to not have to go to her house anymore. I was overall happy the molesting was over but a little part of me missed all of the good feelings I had.

When I was 15, I dressed fully as a girl for the first time by myself and I felt.  I had on a wig I had found, panties, a dress and did my own makeup, not very well but I did get better over time.

I still talked to my friend every day. We would try to see each other when we could. We went ice skating one day across the street from her house. It was cold but we loved to skate and we were having fun. My dirty mind was wishing I had the nerve to ask her to go up to her room but as was always the case, I valued my friend more than anything and did not want to risk losing a friendship I cherished. We skated around and slowly, she came up to me, grabbed the collars of my coat and kissed me. I was on cloud 9. I was in love with her but I had a girlfriend. At that moment, I didn’t care. After the kissed she skated back a bit, I grabbed her collar and drew her in for another kiss. My toes curled when we kissed. That was where it ended. We never spoke of it again until many years later.

After graduating, I dressed more often on my own but still never ventured out of my room. This was a secret that I could not tell anyone. Sure, my girlfriend knew and thought it was weird but didn’t think much of it.

I moved into my own apartment when I was 20 and I was engaged but finally had the freedom to dress as often as I wished. My fiancée at the time knew I liked to dress up and was OK with it, but would not participate. We eventually married and moved into our first home. I had my own closet full of my girl clothes. I may have had 10 or 12 outfits, several pairs of shoes, a wig, my own makeup and under clothes.

About this time, I got online for the first time, this was about 1996. AOL was new and was an eye opener for me. I met and talked to a lot of other crossdressers in my area. It was amazing to talk to so many others who were like me and lived nearby. I group of us would have our own chatroom and just talk. There was a big crossdresser event coming up at a local club and we all made plans to go. I was excited and nervous but was going to finally go out as a girl.

The big day arrived and around 4PM, I went into the shower and shaved everything from the neck down. I covered my freshly shaved body in lotion and set about getting ready. I got out a really sexy black pin striped mini skirt and a silver top. Black stockings and heels completed the outfit. I sat at the mirror and spent over an hour doing my makeup, getting everything just right. I put my wig on and made sure it was straight and then got dressed. I went down stairs where my wife was and she was shocked. She had seen me dressed before but never like this. She was amazed and I always felt, a little jealous. She knew I was going out and gave me a purse and wallet to use for the night. I was touched and thanked her. I went to kiss her goodbye but she backed away. I wasn’t worried. I told her that there would be drinking going on and I would probably stay at the hotel that night where the event was being held if I felt I couldn’t drive home.

About an hour later, I arrived at the hotel and sat in my car nervous as I had ever been. I saw others going in and knew it was now or never. I got out of the car and walked in the door. Immediately, I was asked for my ID. Oh God. He is going to know I’m a guy. I needed to get out of there. Nervously, I reached into my purse and pulled out my license showing a man and presented it. He looked at it, looked at me and said “have a nice night, miss.” What was that? He called me Miss!!! I was ecstatic.

I could hear the music from the lobby and walked in. Right away, I saw a few girls I had chatted with online and introduced myself as Rebecca. Totally spur of the moment decision and it worked. There were 10 of us all together and we had a great time. It was so amazing being with these people who have been dressing in public a lot longer than I had ever imagined and I was relaxed. We danced, we drank, we laughed as girls. The drinks were flowing pretty heavily that night and several of us did spend the night at the hotel. No, nothing sexual happened. I think we were all too tired and too drunk to even think about it.

Waking up the next morning and staggering back to my car, I looked in the mirror and there was no way my wife was going to believe I didn’t get up to any mischief. I straightened myself up as best I could and made my way home. She greeted me in the kitchen and we sat and had coffee together and talked about the night before. She seemed genuinely happy I had a nice time. I went off to shower and put my things into the laundry and took a little nap. I was hooked though and I knew this was not a phase. I knew I was a transvestite and I was happy for the first time that I could remember.

Life went on for us. I got a job working the night shift and on Sunday’s, I would stay up around the clock so that I could sleep all day Monday to go to work the next day. Once it was dark, I would get dressed and sit at my computer and be Rebecca. I would talk to other girls, some real women and a few men. Heck, it was AOL and it was all about exploring your kinky side for the most part. I would stay up smoking pot, dressed as Rebecca and learning more about this new world I was entering. I made so many friends that I wish I still had today but as was often the case, online friends rarely stayed in your life for long.

My wife and I never talked about it. I never really knew how she felt about it but always guessed that if it was a problem she would tell me. Wrong. More on that later. Another outing with the “girls” was planned and I couldn’t wait to get out again. I bought a little white leather mini dress with matching jacket and looked hot. This time we were going to a club called Jacques in Boston. It is a gay club that was very trans friendly and they had drag queens performing. I paid my cover and went in and sat down and ordered a drink waiting for my friends to arrive. One drink turned to two and then three. It was about an hour and a half and my friends were nowhere to be seen. This was the days before texting and cell phones. I was starting to get nervous. I stopped drinking and waiting for them. I gave it another 30 minutes and saw they weren’t coming and decided to get out of there. As I stood to leave, I saw out of the corner of my eye a man got up to leave right after me. I paid no attention to him and went outside. A few steps out the door I was enjoying the night air and hearing my heels click on the pavement. As I got closer to my car, I could hear a voice calling “excuse me.” Panic set in. Was he some nut who preyed on women? Did he think I was a woman? He saw me come out of that club and I guess saw me inside. I pretended not to hear anything and walked, a bit faster. “Hey you…wait up” Panic turned to terror. I could hear his footsteps get louder and in heels on a cobblestone street, I could not go too fast without ending up sprawled out on the ground. I was in deep shit.

He finally caught up to me and said “excuse me, you left before I could buy you a drink.” I was flabbergasted. I was stammering like a fool. I told him that my friends didn’t show and I had to get going. He asked me if I would like to go back in for a drink and to talk. I told him I was sorry but I was married and not interested in men (little white lie). He said that was ok, he just wanted to talk and get to know me. I looked at the time and it was only 8:30 on a Saturday night. I told him one drink and we went in and sat in the back and talked. To this day, I can’t remember his name but we did have a nice chat. He asked me about my dressing and wanted to know all about me. I sipped my diet coke as he had a couple of martinis and around 10:00 I told him I had a nice time but it was time for me to head home. He walked me to my car and said thanks for talking. I told him I had a nice time. He moved in to kiss me goodnight but I backed away and said it was time for me to go.

The entire ride home was a blur. I somehow ended up off the highway and drove through a really scummy city. It was about 11:30 and the streets were pretty empty other than the clubs and a few working girls I saw.  It was still warm and I had the windows down and I heard random men, mostly drunk, commenting on me, wishing I would stop for them. I laughed saying “If they only knew”. I finally got home and my wife was asleep. I slipped into a nightie and crawled into bed with my wig still on. The next morning, I found out just how unsupportive my wife actually was. She lost her mind when she saw me. She told me that she never wants me near her like that again and if I want to sleep in a nightie, I can do it on the couch in the basement. I was crushed. I knew she would never take part in my dressing but to have her be so cruel was devastating.

I kept my dressing to Sunday nights and enjoyed talking to others but something was missing. I wasn’t sure what it was but again felt out of sorts and that there was something that was just out of reach but couldn’t put my finger on what it was. There were not many events for crossdressers in the winter so I just talked with my group of friends and once a month we would all get together at one of their houses for a girl’s night. Some of them brought their wives’ who were very accepting and open about their husbands dressing. I would ask them how I could get my wife to accept this and they all said either she will or she won’t, that there was no middle of the road but as long as she allowed me to be myself and I respected her wishes, it could work. I was having fun being Rebecca but the desire was there for more. I knew I did not want to transition to full time but I also didn’t know what it was I wanted. I knew deep inside, I wanted my wife to accept me and take part in Rebecca but knew that wasn’t going to change.

Winter turned to spring and there was a weekend getaway in Provincetown on Cape Cod for crossdressers. This was it. I wanted to spend an entire weekend as Rebecca. Two other girls I knew were going and we all got adjoining rooms. The hotel we were at was central to all of the activities and walking distance to everything. This was my big chance to spend extended time as Rebecca in a place I could feel comfortable.

The day before the big weekend, I packed my bag and loaded into the car. I had a long talk with my wife and I asked her why she had such a problem with this part of me. I explained that despite what she saw on the outside, I was still the same tender, loving person on the inside. She told me that it was just unnatural and she really didn’t like it but considering I didn’t do it every day she was ok with it as long as I didn’t involve her.

The next morning, I got dressed in a little sundress and a pair of shoes and a cute sunhat and made my way to the cape. I met up with the girls, checked into our rooms and we had a great time. Sightseeing by day, drinking and partying at night. To spend an extended amount of time as Rebecca was liberating. I felt free and for the first time, I felt complete. I made a lot of friends that weekend and we all stayed in touch for a while but as usual, we eventually lost touch.

About a month later, my wife and I received some great news. She was pregnant with our second child. We had a daughter a few years prior to this and she was and still is the absolute joy of my wife. We are extremely close to this day. I didn’t mention her earlier and will not mention my children after this part of the story because I feel they are not relevant in any of this. To this day, neither of them know about their dad although I am sure they would not have a problem as I raised them to be accepting of others no matter what.

We found out we were having a boy and I couldn’t be happier. My wife on the other hand was happy but miserable at the same time. She had been battling severe depression off and on for years and was not able to handle being off of her medications while she was pregnant. At one point in her pregnancy, I came home from work to find Department of Social Services workers in my home. I asked what was going on and they said my wife had contacted them because she felt she was not fit to be a mother. While part of me agreed, I kindly escorted them out of my house. I was furious. They told me there had been no evidence to either of us being unfit and were not aware why they were called. I explained to them my wife was going through a depression and my mother had been staying home from work to help her. I assured them that she would be fine once our son was born and she could get back on her medication. All was not fine though. Our marriage was beginning to suffer. She as erratic and out of control at most times. Our 4-year-old daughter was looking after her mother and this bothered me. We finally made it to the delivery though and she had actually been doing ok.

We arrived home with our son and things seemed ok. She was back on her medication and feeling stronger. I didn’t dress for a couple of months because life was just too busy with a new baby in the house.

I had noticed her moods changing. She was bitter a lot. She was a very good mother but something was just off. I couldn’t figure out what it was. We didn’t talk much. We began experimenting with couple swapping. We met another couple and got together a few times. The guy would take her to a hotel and I would stay at our house with his wife. We only got together a couple of times but I did introduce her to Rebecca and she loved it. We had sex with me as a woman and it was amazing.

After getting together with them a few times, my wife decided this wasn’t for her and she put an end to it in a rather rude way. One night they were over our house just hanging out and she started yawning in an exaggerated way saying how tired she was and at 7pm, she got up and announced she was going to bed. I apologized to our friends and saw them out. I went up to the bedroom to make sure she as alright and she asked if they were gone. I said that they were and she got up and went downstairs as if nothing had happened. I wasn’t mad that the swapping was over, I was mad at how she handled things. She never spoke to me about how she felt beforehand and I was just as shocked as they were when this went down. I decided that my marriage, such as it was at his point, was more important.

A few weeks later, I went off to work like any other day, but this was unlike any other day. It was a Thursday and as was usually the case, I would pick out what Rebecca was going to wear that weekend and get things washed. I opened up my closet and it was completely empty. I knew everything was there that morning, I saw it. I called down and asked her to come upstairs and she asked what was up. I asked her where were my things. She asked if I heard that sound, and I had. It was the garbage men taking the trash and at that moment I knew. She looked me right in the eye and said “I just killed Rebecca.” I was devastated. I couldn’t stop crying. Not for the loss of my things but at the act of betrayal I felt. I asked how she could do that and she said it was easy. From that moment on, our marriage began to fall apart. Gone was the respect we had for each. Gone were all the good times we had and gone was what I wanted to be. However, I was a father to two amazing children that were my world and I decided not to run. I stuck it out. Big mistake.

A few months later, her depression started to return. My mother had passed away and was not able to help like she had in the past so we had to rely on her mother, who I had hated and hated me for years. The tension in the house was so thick it was palpable. I was miserable, my kids were not happy and my wife was now in a psychiatric hospital for the 4th time in 10 years. I couldn’t do it anymore. My kids and I deserved better.

With all of the issues we had been having, I started to think about my old friend and wonder how she was. I missed her terribly. Her husband and my wife did not approve of us being friends and forced us to stop talking to each other. I always felt they knew that we truly loved each other on a level neither of them could ever understand. I knew where she lived but had no idea how to go about contacting her or if she even would want to hear from me.

One day, I remember it was April 2001. I came home from work and my wife was still in the hospital. My in-laws were there watching the kids and I sat down at the kitchen table and we talked about the situation. I told them I didn’t know how much more I could talk and that my kids were still young. They looked at me like I was the biggest asshole in the world and said “what are you going to do, divorce her?” I said honestly I am thinking about it but I just don’t know. They were so angry they just up and left. Good riddance to you. It was always a tense relationship between us. She was their only child and no matter what, could do no wrong. Again, all I was able to think about was my friend and I missed her more and more every day.

She eventually came home from the hospital but would be going to a day treatment facility for about two months. I was at a new job in a new field and relied on her to take care of the kids. By the summer, she was doing ok and things were just…..there. There was no sex. There was no communication. There was basically nothing but a man and a woman living together raising their kids.

My best friend had just gotten divorced and had fallen on hard times. We had an in-law apartment at my house that was empty and we let him move in. I never thought anything of it as he was like a brother to me and trusted him completely. Big mistake.

Soon after that, the events of 9/11 happened. I was at work and after the Pentagon was hit, we were all sent home. I remember watching the events on TV with my friend and my wife and she was crying and she turned and put her head on his shoulder. I didn’t think anything of it. I had felt that my marriage was over by that point and my mind was occupied on how to end things and not hurt my kids. Little did I know, at the same time, my oldest and best friend that I missed was having marital issues of her own. I wish we had been in touch all those years. We could have been there for each other and our love would have blossomed to what it is now much sooner, but, thanks to our spouses, we were apart.

Soon after, we had grown so far apart, I started sleeping in a separate room every night. I would come home from work, have dinner with the family and clean up. After that, I would usually go up to my office to watch TV, my kids would go off to their rooms and my wife would be in the living room. The kids would come and hang out with me then go back to their rooms and do their thing. When it was bed time for them, I would go into my office, close the door and go to sleep and repeat the same thing night after night for a few years.

Later on, I would notice strange things. I would come home and see tire tracks in the snow of a car pulling in and leaving. Odd. I would ask who was at the house, thinking maybe it was her parents or someone but was told that nobody had been there and that I was crazy. One day, I came home and the bathroom mirror was foggy as if someone had recently showered and the toilet seat was up, yet her hair was dry and obviously she didn’t just shower, nor did she pee standing up. I knew something was up

We tried doing things as a family together to see if we could recreate some spark but nothing every came of it. One night, we went to the drive-in to see a movie. It was about 2 hours away. We spent the afternoon at a zoo in the same town then watched the movie and went home.

When we arrived home, there as another car in the driveway. Our friend had a date over. He had seen this woman off and on and my wife never liked her. I thought she as ok and she made my friend happy. My wife lost her mind. She barged into his apartment like a lunatic screaming her head off. This woman was twice her size and I was kind of waiting for her to strike back but she took the high road and left. At that moment, it clicked for both of us. She was screwing around with him. Naturally, they both denied it. You don’t have to be Columbo to figure out what was going on.

Part of me was relieved and part of me was enraged. My best friend, the man I thought of as my brother betrayed me. He knew we were having problems and he took advantage of it. I blame them both. To do this under the roof I provided for both of them made me sick.

I let things cool down for a while. I knew not to do anything in haste. I thought it over for months. I had nobody to talk to about it. Finally, I decided that it was over.

It was October 2004 and the Boston Red Sox had just won the World Series for the first time in 86 years, 12 years ago this day as a matter of fact. That is why I can remember exactly when it was. After dinner one night, the kids went to their rooms and I told her that it was over and I wanted a divorce. The response I got was not what I expected. Tears began to flow and I felt like an asshole. I just hurt this person I had loved for a long time. We talked. We yelled. We argued. I thought it would be best to go to separate corners and think about things.

Like a fool, I started to change my mind. Maybe we can save this. Maybe we haven’t gone too far. I sat her down and said maybe I was too quick to ask for a divorce. Let’s try and work on things. Again, I was surprised when she said no, it is over and she was filing for divorce. Now I was the one who wasn’t taking it well. I accepted her decision as I knew it was for the best. I went to my office and cried for the first time in I don’t know how long. For two days, I stayed in there, only leaving the room to see my kids and eat. I talked to them and told them what was going, reassuring them it was not their fault and trying to comfort them. As a credit to the people they were then and are today, they took it very well. They knew we were not happy together. My kids are the most amazing people I know and I like to take an ounce of credit for helping them to be they people they are.

We discussed things for months. Neither of us could afford to live anyplace else so we stayed under the same roof, her in her part of the house and me in mine. We were cordial to one another. The fighting and bickering was over. We just had to get through this next chapter in our lives. We had no idea how long of a process this was going to take.

August 2005, she told me she was going down to file for divorce. I only asked one things, that she doesn’t have me served on my birthday or in public. I would go to the office and get the papers. She agreed for the most part. On my birthday, she filed for divorce. Looking back on it, it was the best gift I ever received. At least she didn’t have me served in public.

The next step was to sell our house. October 2005, our house that had been in my family for over 60 years went on the market. The market was just starting to crash around this time. We owned 20 acres and had a house that was half new and half old. We had no money to fix up what was needed. I thought it would be a quick sell. Boy was I wrong. The house sat on the market for over 3 years. The judge would not grant is a divorce until one of us moved out. I was frustrated beyond belief. I was eager to start my new life and get past this chapter. I had plans and wanted to get started.

As the divorce was underway, I started to miss my dressing. I had it all planned out. I was going to get my own place once our house sold and live my life the way I wanted. Not really sure what way that was at that point but I knew I would figure it out and I knew dressing up again would be a part of it. I had picked up a couple of things and kept them hidden. Mostly a couple of nighties and some panties. I was comfortable with that for now. I knew I would have the opportunity to explore it more once I was on my own. I knew though that I would never be married again. Was I ever wrong about that.

March 2008, fate stepped in and everything changed. We had a court date scheduled for April 1. I tried not to think about it on this day as it was my daughter’s birthday and as was the custom, we were going out to dinner as a family to celebrate. That would be the last thing the 4 of us would ever do together again.

When we got home, I went up to my computer and checked my email. My eyes just about shot from my head. My heart was racing and I felt a rush of emotion that I cannot describe. I had an email from a name I recognized. It was my old friend that I had missed so much. I can’t believe she found me. Then it hit me. She was looking for me. She must have missed her friend. I opened the email and started to read and my hand to God, all the love I had ever felt for her came rushing back to me in a heartbeat. I read her email and I was crying. I replied back to her telling her I was in the middle of a divorce and that I was so happy to hear from her and how much I had missed her and thought about her over the years. One email turned into two. Then three. From there it was a steady stream of emails back and forth. She had to be careful though. Her husband was a jealous man and if he knew she was talking to a guy, would be mad. If he knew it was THIS guy, he would have lost his mind and made her life hell. She kept it quiet from him but I told my soon to be ex. They had known each other through me. My wife had thought of her as a friend but in reality, my friend was friendly to her simply because she was with me. My wife said she felt betrayed and I laughed at her. She accused me of seeing her behind her back for years. I assured her that I had not been, for if I had, we would have been divorced years earlier.

After a few days of emails, my friend had reached out to me in pain. She found naked pictures of another woman on his phone. She was hurt but more importantly, she was DONE with him. She knew he had cheated in the past but this was it for her. I’d like to think that part of what played into her decision to end things with him was because of me and I truly believe part of it was. We talked and decided we would meet for a drink to see each other again and get caught up. Six days after the first email and 28 years after we met, we had our first date. I remember pulling up and seeing her in the mall entrance.  My heart was racing. I parked the car and walked in and we hugged. There were tears in both of our eyes. I missed my friend so much, but this was different. We went inside and sat down and ordered a drink. I’ll never forget, she said “let’s get this out of the way first” and for the second time in our lives, she leaned across the table and kissed me. Just like the last time, my toes curled when we kissed. At that moment, I knew I was in love with her and she felt the same for me. In my heart, I knew we would be married one day.

We went to our homes that night but we knew it would not be the last time we saw each other. We made a date two nights later. She got a hotel room for us. This was it. The night I had dreamed about most of my life. We were going to make love. I got an email she was there and I showered and made my way there. I was so excited and nervous. I hadn’t been with many women. Two actually. Was I going to be good enough? Was I going to let her down? Turns out, that wasn’t an issue. I made her feel things that night she had never felt. Ten times to be exact. It took me a long time though. I was on a medication that was slowing things down in that area. Fortunately, I was almost done with them and that wouldn’t be an issue again. It was an amazing night though. Physically and emotionally. We felt things we never dreamed were possible.  A few hours later we parted and went to our homes. We knew it though. We were in love and our future was together. We would see each other at every opportunity until we could make things work out for us.

Still though, I had an issue at home. We were trying to get a divorce but until our house sold, we were stuck. She was living with her husband still and I was stuck in my house but I was motivated and thought I found a way out.

My dad and his new wife had a lake house not far away. It was actually the half way point between her house and mine. I explained the situation to my dad and seeing they never used the lake house, I could stay there as long as I needed. I could stay as long as I took care of the place and didn’t have to pay rent until my house sold. No problem. The next weekend, I loaded up my car and moved in to the new place. It was still March and winter was winding down. It was bitterly cold and there was no heat there but I made do. It was only cold at night but with enough blankets, I was fine.

April 1 was finally here. I went to court and seeing we no longer lived together, the judge pronounced us ex-husband and wife. I walked out of the courthouse and stood on the front steps. Like Mel Gibson at the end of Braveheart I yelled “FREEEEDDDDOMMMMMMMMMM. My now ex walked out at that moment and was less than impressed but I didn’t care. I was free of her and my new life was ahead of me.

I jumped in my car and drove up to my now girlfriends job and hugged and kissed her with so much love, it was visible to others. Our love has always been like that. On two separate occasions, we were eating out at Ruby Tuesdays, romantic, I know. Both times, the wait staff commented on how sweet it was the way we looked at each other and how much love they could see. She may not know it, but more than 8 years later, I still look at her the same way and feel the same love.

She had finally reached a point where she told him he wanted a divorce. He was not all for it but he knew they too were done and accepted it. Until he found out who she was now seeing. Once he learned it was me, he was dragging his feet and fighting the divorce. As much as he said he didn’t want it, he knew it was over.

It was now May and the weather was nicer. I don’t really remember how we made it happen but we were finally going to spend our first night together. I was so excited. When she arrived, it finally felt real. Like we were really a couple now. I cooked her dinner for the first time and we hung out with some of my neighbors and had a fun night. Later, we went to bed and made love to each other. It was the first night sleeping together and the it got cold. We stayed up late laughing and talking. We got to laughing so hard talking about the Wendy’s girl and damnit, to this day, we have no idea why or what was so funny about it, but that night, it was the funniest thing going.

I would take a day off from work here and there to spend her day off together. Every day making love to each other. It was always amazing and still is whenever we make love. But as the months went on, another hurdle would be through in our way. She lost her job as store manager as the chain she was working for was going out of business. It was 2008 and the economy was crashing faster than we could blink an eye. A few days later, her husband lost his job. This was a huge deal. We had no way of seeing each other now. She couldn’t get out much because she didn’t want to cause problems at home. They were over but much like I had to, they had to stay living together.

The summer passed by and fall was here. She found a new job and soon after so did he. Things were turning around. The holidays came and went and it would be the last year we would not spend them together.  It was tough, but we knew what was waiting for us on the other side.

February 2009, her husband moved out. Her parents had an empty house they would rent to us. They now knew about us and remembered me from our childhood and they were genuinely happy for us. To this day, her parents have been a huge help to us.

In late March, I moved her out of her house and into the new place. It would still be a few months before I moved in with her. Not long after, finally, my house sold. The last link to the past. I had grown up in that house and was not the least bit sad to see it go. I had started a new life and was happy. So far, this new life made me happy and nothing was missing for me. Not even dressing up.

In July of 2009, I moved into that house with her and we had a great life together. We were happy for the first time that we could remember. And the sex we had was unbelievable. Every night for months we were at each other.  Again, I will not go into graphic detail but let’s just say that what one would read or see in porn movies was nothing compared to us. One day, I summed it up when I said our love is born of our friendship and set on fire by passion and that’s what we were like.

That year, she had hurt her back at work and was laid up for a few weeks. She got stronger but was always in pain. Eventually, it got to a point she couldn’t even walk. We made an appointment with a specialist and found out she needed spinal surgery. We got through that and I took care of her every day. The day of the surgery was rough for her. I kissed on her way in and fought back the tears. I knew she was in good hands and would be find but this was the woman I loved and I was worried. When the doctor came out and told me everything was fine and I was able to see her. She was still pretty groggy but when she looked up at me and said she felt no pain I was crying I was so happy; kind of like I am now writing this.

She soon was back to her old self but once again, life happens. I hurt what I thought was my shoulder at work. I saw a doctor and they told me it was my shoulder, what else would I think. The pain never went away and I went for further x-rays a few months later. When they were doing the scan of my shoulder, the tech asked me what happened and I told her. She said she was going to take an x-ray of my neck just to be safe. Good thing she did. Turns out, I had 2 herniated disks in my neck that were pressing on my spinal cord causing me pain in my shoulder. It’s nice to know an x-ray technician thought of this and not the Doctor I had seen.

For the second time in 11 months, we were back at the hospital for spinal surgery only this time, I was the one going under. When I came out of the anesthesia, she was the first person I saw. I guess I wasn’t doing too well as there were some issues with my heart and she started to panic. After a few moments, I was fine. I will always feel bad for scaring her like that even though I had no control over it.

She nursed me back to health and life carried on for us. Our love making intensified and was more frequent, if that were even possible. The kink level started to increase as well. We were broadening our horizons sexually and incorporating more into it. We used toys together, on both of us. We role played together and it was always amazing together. We also had nights where we just made love to each other and that too was incredible. We didn’t need all the extras but we enjoyed them.

A couple of years passed and finally, we decided to get married. It was a simple ceremony with our kids and her immediate family. The wedding was at her sister’s house and it was beautiful. We both cried saying our vows. After 33 years, I finally married my best friend and I was happier than I ever thought possible.

For our honeymoon, we went on our first cruise together and had the time of our lives. We were newlyweds and for both of us it was new experience. This was the first grown up vacation that I had ever taken without kids. It certainly would not be out last. We fell in love with cruising and we love sharing it with each other. Seeing beautiful beaches and exotic places we never thought we would see has made memories to last a life time.

Summer was and that meant her work season was about to start. She now managed Halloween stores and each year in July, all employees went to the company’s headquarters for annual training. This was the first time I would be home alone in years.

She drove down to New Jersey and I stayed home. The first night, I was bored out of my mind. I was puttering around the house and saw an old French maid costume she had got the year before and a wig. My mind started turning right away. The next thing you knew, there I was. In a wig and makeup, dressed as a maid. I spent the night like that and felt great. I put everything back exactly like it was so she would not find out but I had the memories and a couple of pictures to look at now and then.

That fall, our sex life took a new turn. Mostly it was new for her. I have no idea what made it happen but she sent me off to a Halloween store. There I bought a sexy red wig and a pirate wench costume. She did my makeup for me and I felt great. For the first time, I was dressed as a girl and was sharing it with a woman that I loved. I had such high hopes. We ended up having sex where I was her submissive slut and I had hoped she liked it as much as I did.

When the sex was over, I showered and changed back into guy clothes but was hopeful it would happen again. She had me pick out something online and I ordered a sexy black dress. She did my hair and makeup again and this time, I was her dominant lesbian lover, a role I had always dreamed of. I knew she was really into it and the sex as always was great. Again though, once it was over, I had to change back into guy mode.

That December, an event happened that shook our world. Something I had never thought would happen to me, happened. I had just taken the dog out and went back in the house. As I turned to close the door, I saw a police car pulling in. I turned to my wife and said “hey hun, there is a cop in our driveway.” I turned back to the door and suddenly my yard was filled with cars. They came to the door with a warrant and said they were looking for me. I was shocked to say the least. What the hell had I done to cause this. I asked what this was about and one cop who reeked of arrogance said “You know what you did.” My house was filled with local police, Homeland Security, FBI and Immigration agents. What the hell was going on. Then they said the warrant was to seize and search any electronic device. Still, I did not know why and I asked. Office Arrogance said “this is a CPI. Do you know what that is?” No I said. They said I was being investigated for child pornography. At the same time, I was relieved and enraged. I knew I had never downloaded or sent that, much less ever even seeing it. They separated us and questioned us both, each of us adamantly denying this. As they were searching the house, the stumbled across a box under my bed. That was where I kept a small bag of pot. I was cuffed and put in the backseat of a cruiser and driven to jail. The took our computers, modem, cell phones and router.

I was charged with possession of marijuana, put into a cell for a few hours and released to my wife. They had given her a ticket to appear in court for the pot as well. We went home and were devastated. Every noise we heard made us jump. Terrified doesn’t even begin to describe it. We knew I had done nothing wrong but this was just crazy.

The investigation lasted about 9 days when we received a call that we can pick up our things and that nothing was found. I knew that I would be exonerated but the whole thing took its toll on us.  We got everything back and a few days after the new year we left on another cruise and got our mind off of things.

When we returned, we had to go to court for the pot charges. The district attorney sat us down and said that if one of us would plead guilty, he would drop the charges for the other. Without hesitation I said no problem, I will take the wrap. Technically, I could have pushed the issue where the search warrant did not cover the pot and that it was found in a manner that the warrant would have excluded it. I let it go and plead guilty. The D.A. was kind enough to drop the charges to disorderly conduct and I got a fine and 2 years’ probation.

Now that this was behind us, we started to put out lives back together. We started making love again but it was a long time before we would engage in anything beyond that. During the investigation, they laid every sex toy out on the bed and took pictures of it. My wife felt dirty and violated and it took us a long time to get back to being ourselves.

We never played dress up again after that even though we had talked about it and said we would. I felt like I was missing it and any chance I had to be home alone for a few hours, which was extremely rare, I would take advantage and get dressed. She never found out, thankfully. I kept everything hidden. I felt like I was doing something wrong when I really wasn’t. I understood it was hard for her to see her husband like this but this is who I am inside. I am a crossdresser. She is supportive of others who do this but not me. I wish she could find a way to allow it and be ok with it. I hate hiding things from her.

We found out we were moving to a bigger house. We had accumulated a lot of junk over the years and went through a huge clean up, throwing away a lot. Sadly, the wigs and any costumes or clothes that we had for me to have fun with were gone. She tossed them all into bags for Goodwill as if it were nothing but to me, a part of who I am was being stuffed into those bags. It looks like that part of me is almost dead. It hurts inside to know this but I love my wife and will do anything I can to keep us happy together.

We just found out she has to go away for a week for work. The desire to dress started to return big time, but I had nothing to wear, no wig to make me look feminine. Nothing. Then I realized, I can order things and have them sent to the old address. The house is mostly empty now and I can go by there to pick up my orders and hide them when I have a chance.

I ordered a dress, a new wig and some lingerie to wear to bed. I am looking forward to being a girl again, even if it is for a few days. I don’t think I will ever see the day when I can dress when I want but I will always hold out a glimmer of hope that she will change her mind and let it happen again.

Until then, life goes on while I stand at the crossroads.





Submitted: October 27, 2016

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