Chapter 2

My name used to be Sandy Clayborne. I was married for 19 years to my wife Karen and raised two children (twins), Tom and Jessica. They were now going to attend college and live away from home. For many years I felt that there was something wrong with me. That everything wasn’t right. I always had a hard time liking myself, and if you look in the family photo album, you will rarely see a photo of me, and if you do, you will notice I was never smiling, more like scowling at the camera.

These mental issues seemed to worsen for me as I got older. When I hit 40, I enlisted a psychiatrist’s help to determine why I felt the way I did. It was a secret I kept from my wife and family, and I couldn’t allow them to know what was going on in my life personally.

After a year of therapy with her, I insisted that she finally talk to me about her findings.

“OK, this isn’t usually the way we work, but I will humor you. First off, there is nothing wrong with you. You don’t have any psychosis of any kind, but you seem to be questioning your gender. The way you have answered the tests I gave you led me to believe that you may not be comfortable being a man. Quite simply, you may have the self-image that you are a woman in your mind, and your issues could stem from feelings of gender incongruency. The feelings of anguish and the negative opinion you have of yourself could all stem from this issue.”

“Wait, what? Are you sure? I don’t feel like I am a woman.”

“It’s not important what I think, and it’s how you feel about yourself that counts,” she told me, “As a psychiatrist, we usually lead our patients and let themselves discover who they are in life.”

“So who am I, Doctor? I honestly don’t know at this point.”

“Just think back on all the things you have told me over the last year.”

I sat back on the couch and wondered why she would say this to me. I remembered all the girlfriends I had when I was younger and never really played with the boys. I played with my sister’s barbie dolls too, and I loved dressing them up, but I had already realized I couldn’t tell anyone and did it secretly. I remembered being jealous watching my sister be so girly and wear all her frilly clothes, wondering how I would look wearing them, and trying them on when no one else was around. Not to mention I loved using her EZ-bake oven and making cakes with my mom, even wearing an apron, but I found I could get away doing this with Mom.

I remember my childhood was mostly happy, but things turned awful for me when I started changing into a man during puberty. I hated going to the gym since I didn’t want big ugly muscles. I hated that I started growing so much body hair, and my voice got so much lower. I hated how tall I became and how masculine I looked. I especially hated what was hanging between my legs. Jesus! It bothered me that I was becoming a man, now that I thought about it.

“Wow, do you think I want to be a woman? That would make me transgender.”

“Again, it’s not about what I think, Sandy. How do you feel about this?”

“I don’t know, but these thoughts have me questioning myself to the core.”

“I have an assignment for you, and I was hoping you could check out these links. I will email you. When I see you again, I would like to know your opinion on them.”

The doctor sent me an email with several links online and gave me a book to read. My mind was in a blur when I left her office. Transgender? Me? Was I a woman trapped in a man’s body as she suggested? Sure, I was never the most masculine guy out there; I was always thin, never muscular, and I didn’t play team sports since I didn’t have the body for it.
Being tall and thin, I liked to swim, and I enjoyed running since they fit my physique. I got home and looked into the mirror, and immediately scowled at my reflection. Why did I always do that?

No one was home, so I tried an experiment. I went over to my wife’s dresser. I went over to her closet, took a dress, and put it on myself. I pulled out a bra and put it on after a lot of fumbling with the catches. I stuffed it with pantyhose and filled it out. I took the rubber band out of my ponytail, for I had always worn my hair long, grabbed a brush, parted my hair in the middle, and let it run down over my shoulders.

I went over and looked into the mirror, and a girl looked at me. Then, I smiled back at her! Maybe the shrink was right? I enjoyed looking like a girl! I walked over to my wife’s vanity, put on some powder, used an eyebrow pencil on my brows, put some mascara on my eyelashes, and finished it with pink lipstick. I walked back to the mirror and enjoyed my reflection even more. My knees suddenly got weak, and I almost fell. My god, she was right! Part of me wants to look like this and loves looking like this.

How was I going to tell my wife this news? I had no idea. I thought it was best to put everything back and talk to the shrink to see my next step.

One thing was sure in my mind. A part of me enjoyed looking like a woman, and I had smiled at my reflection for maybe the first time in my life.

I called up my psychiatrist’s office. Dr. Knudsen picked up the phone, and I told her what had happened and I needed to discuss what I should do next. She said she could fit me in tomorrow morning, and I told her that I would be there.

I remembered all the web links she had emailed me. I decided I had better start reading up on this topic. I didn’t know how I would handle this, so the more information I had, the better decision I could make about this.

I sat down and started reading. I went through several websites and lengthy articles about Transgender care. One thing kept coming back to my mind. It looked like the only way I could get through this was to become a woman and live as one, and there seemed to be no better solution.

How could I tell my wife and kids that their father would become a woman for the rest of her life? But as I read, things got even more complicated. I was able to change the appearance of my body with hormones and testosterone blockers. I could grow natural breasts, and my fat distribution would change to give me bigger hips, butt, and a more feminine face. One website gave a whole list of things that could happen to me on hormones. There were also operations that I could have performed to feminize my face and get breast implants if hormones didn’t give me large enough breasts. And then there was the big one, Sexual or Gender Reassignment surgery. I would give up my penis to construct a female vagina. How far did I want to take this? Taking on a female identity was a long way from where I presently resided. What would I call myself? That took me all of two seconds as the name Sandra popped into my head. I closed my laptop and took a deep breath, and let it out. If I went through with this, it would completely change my life. I might lose my family over this too.

I didn’t want to say anything to my wife yet, since I didn’t know what to say. Maybe I will have a better idea after tomorrow.
The next day, I was in Dr. Knudsen’s office, and I told her about my experiment and how it made me feel. There is something in this transgender idea, but I have no idea what I should tell my wife. The thought scares me. What if she wants a divorce from me? What if my children no longer wish to have anything to do with me?

Gail suggested that my wife come into her office, and we attend a couple’s session to see how things go. You will have to tell her sooner or later, and I can’t predict how she will react, but we won’t know until you tell her, and maybe I can help soften the blow.

Well, we came in together for the couple’s session. I told Karen what I was going through, and we had concluded that I was transgender. I then explained the only way I could get through this was to become a woman.

Karen replied, “I am not a lesbian, and I married a man, not a woman.”

She sat there fuming at me for even suggesting that I would want to become a woman.

“If you go ahead with this insanity, our marriage is over, and I want no part of it.”

Gail tried to talk to her, but she just became angry, and she stood up and stomped out of the office.

I looked at Gail and said, “That went well. What should I do now?”

She looked at me and said, “This is the hardest decision you will ever make in your life. Ask yourself if you are happy with the way things are at present. You realize that you are depressed, and this condition will only worsen. You may start thinking that suicide is a way out of this dilemma. Unfortunately, your wife has forced you to choose between living as a woman or staying the way you are. It’s up to you now.”

Well, to make a long story short, I chose to live my life as a woman. Karen immediately divorced me, but when I told my kids what had happened, they stood with me, telling me they had transgender friends and I was one of the bravest people they knew for doing this. If Mom couldn’t handle this, she never really loved you in the first place.

Dr. Knudsen got me in touch with an endocrinologist, and I immediately started hormone replacement therapy. My wife had left, but my children supported me, so it was bitter-sweet.

We settled our divorce. Since Karen made as much money at her job as I did, we just split our assets. We set up an education fund for our kids as part of the divorce agreement. We sold our massive house in the suburbs. She took the furniture she wanted, and I took what I wanted and found a cute townhome downtown. I placed an offer on it and was able to move in quickly. It had three bedrooms, so I put the kids’ bedroom sets into the other two bedrooms and bought a new master bedroom set since my ex-wife took the master set from the house. Now my kids both had a place to stay when they visited. I used the furniture and TV from our family room and took the dining room set and kitchen table with me, as Karen didn’t want either of them.

Karen wrote off our kids as well, simply because they had supported me. She gave them the same type of decision to make, her or me, and all it did was drive a wedge between them.

I went to dinner with my children, and they told me what Karen had done. I kissed them both and said it didn’t have to end like this had she been more reasonable. I told them not to lose hope in her; maybe she would change her mind one day. I had not yet started wearing woman’s clothing yet, and I didn’t have any. I asked Jessica, my daughter, to go clothes shopping with me. I laughed with my son, Tom, and said, you don’t have to come. I doubt you would be interested in this. He just laughed and told us to have a good time shopping. I told both I had room for them at my new townhome if they ever wanted to visit and stay overnight.

That weekend Jessica accompanied me to the outlet mall, and we spent the day buying everything a woman could need in the way of new clothes. Oh, and the shoes! There were three outlets there selling shoes, and I went a little overboard, and I must have bought 30 pairs of every kind of shoe I needed and runners and new golf shoes. There was also a discount beauty store there, and we went in and picked out everything she thought I could need. Jessica told me, don’t worry, Dad, I will help you learn how to put all of this on, and you will be the best Mom a girl could want. I started to dress up when I was at home and began to feel more comfortable with my new self.

After a year on hormones, I finally got the courage to dress as a woman at work. My first stop was HR, where I informed them that I would be changing my name to Sandra and would now be presenting as a woman at work starting next week. On Monday, I socially presented as a woman and went into my office dressed as one. The people at work were quite accepting and respectful of me. If anyone made any jokes at my expense, I never witnessed them.

Well, almost three years had now passed. After starting hormones, I never really got large breasts. So, after two years on HRT, I traveled to Thailand for implants and facial feminization to soften my masculine looks, and I also had my prominent Adam’s apple shaved. Six months later, I decided to return and get the SRS operation performed, and I now felt that I was a complete woman. My ID displayed Sandra Clayborne and my new photo with an F for sex.

The strangest or maybe not so odd part was how my sexuality evolved. I never considered myself gay, and when I was a man, I preferred women. But somewhere along the way, my attitude towards men changed, and they started to look attractive to me. I still looked at women, but now there didn’t seem to be a sexual desire; I was more interested in how they dressed and looked. The first time I had sex with a man, I was very nervous, but since I already knew my way around their equipment, it was delightful for me. I don’t know if this was due to the female hormones, or maybe my feminine side helped me change.

It was three years since my divorce that I celebrated after my SRS and officially became a female with my children, and they were overjoyed to see how happy I had become. They both called me Mom, and I loved it.

Jessica asked me, “Mom have you thought about dating anyone yet?”

“Yes, but I wasn’t sure that I was ready to date until now. I have now transitioned entirely into a woman. Everyone at work calls me Sandra, and they have all accepted me there. I gave away all my old male clothing to charity, and I am a woman from here on out.”

Tom thought I should try going out as well. They both wished me luck at finding a boyfriend, though I wasn’t sure how things would work out for me.

I started dating, and several guys later, they were gone as soon as I told them I was transgender. Most of them couldn’t handle that I was once a man. Before telling them, I tried having sex first, and they would still blow me off. I thought to myself, why tell them at all? I sincerely doubted I would find anyone I wanted to marry, and I wasn’t looking for a long-term relationship anyways. I changed my dating strategy and went into stealth mode. As far as my dates were concerned, I was a woman. But if any of them asked me if I was trans, I would tell them the truth. I wasn’t going to lie about it.

So last Friday was the night I first met Robert. I had already been dating for almost a year by then, and when he first walked up beside me, and I kept looking up and up to see his face when he spoke to me, I felt this was a man I could be interested in dating.

Robert sat down beside me and nervously sipped his beer. He seemed lost in his thoughts, so I nudged him and asked, “A Penny for Your Thoughts?”

He gave me a warm smile and replied, “It’s that obvious?”

I just smiled back and said, “Let me guess, you are freshly single, and this is the first time you have been by yourself in a bar for a very long time.”

His mouth dropped, and he said, “Wow, you are intuitive. My wife of over 20 years divorced me three months ago, and I am still trying to pick up the pieces of my life.”

I smiled and said, “It’s a small world. My marriage ended over three years ago, and irreconcilable differences were the reason given. So here I am looking for someone, anyone really, to sit down beside me and help cheer me up.”
It was like a dam burst. Robert opened himself to me and told me all about his recent divorce. I smiled, thinking how my wife cut me loose when I told her I was transgender and wanted to become a woman. He didn’t have to know that part about me yet. I did tell him my name was Sandra and what I did for a living. Robert’s wife sounded like she found someone else who probably made more money than she did; I bet it was a doctor. So, she decided it was time to move Robert out of the picture. I don’t understand why some women don’t marry for love, they marry for security, and when they find a better deal, they move on. I didn’t go into many specifics from my divorce, as I didn’t want to shoot myself in the foot just yet.

Lucky me, I thought Robert was a great catch, though I am just looking for a boyfriend, nothing long-term, right?
Many guys would realize I was trans as soon as they saw how tall I was and how big my hands and feet were. I am sure that Robert had noticed that, but he didn’t seem to mind for now.

I was amazed at how many interests we shared. I was a guy for most of my life, and he was probably amazed right now that a woman would be interested in some of these things. I still liked cars, football, and golf. Becoming a woman won’t stop that, and why should it?

We talked politics for over an hour. We talked about all kinds of things and found we shared similar political views. Robert was an intelligent man, I could see that, but when he looked at me, all he saw was a woman, he didn’t even try to clock me, and I was grateful for that.

We ended up talking at a nearby café, and Robert just kept checking all my boxes. He seemed so compatible with me, and I couldn’t find anything wrong with this guy. That his ex-wife divorced made me seriously question her sanity. Robert reached into his jacket and pulled out a business card; he wrote his cell number on the back and asked me to call him as he would love to see me again. He told me that I was an amazing woman. That made me blush; Robert thought of me as an amazing woman. I accepted his card and told him I would probably give him a call. We left the café, and I called for an Uber to take me home. He waited with me on the sidewalk until the Uber arrived. We made small talk waiting. Robert told me he lived in a condo up the street, and he enjoyed my company and had a great time. I thought he would move in and kiss me, but he stopped himself. I smiled internally at that. We said our goodnights, and he closed the door after helping me get into the cab.

I told the driver my destination. She smiled at me in the mirror and said, was that your date? I said yes, he was. How did it go? I replied, it was great; if I wanted to get married again, he could be the one, but I would like to know him better.
The following day, I had made myself coffee and breakfast, and after I ate, I decided to give Robert a call. He answered on the first ring, and I said hi to him. I told him I enjoyed his company last night, and if he wasn’t busy today, there was a new art exhibit at the art museum, and I wondered if he wanted to go with me there. He thought it was a great idea. I told him of a nearby café to have lunch before visiting the museum. He told me he would meet me for lunch, and we ended the call.
I went over to the café a little early. It was a lovely day, and I sat outside on their patio. I saw Robert walking up the street and waved at him. He was soon seated beside me, and we continued our conversation from last night. We enjoyed lunch together and learned many things about each other’s likes and dislikes on a wide variety of topics. We finished lunch, and I told Robert we would split the bill. He objected and wanted to pay for lunch, but I insisted, so he gave in and let me pay my share of the bill. We left the café and walked over to the nearby museum.

It was an exhibit of Dutch old master’s Renaissance paintings, and we spent all afternoon looking at them and the other displays in the museum. I loved them as they were so realistically painted, with incredible detail and craftsmanship.
Robert wanted to continue our date and asked me if I had a favorite restaurant. Trattoria Il Forno immediately popped into my head, and I felt it was the best Italian restaurant in the city. I had been there many times and was sure Robert would enjoy it too. He looked the place up and made reservations for two over his phone. We walked down the street to where Robert’s car parked. It was a late model BMW M3 coupe with optional wheels and low-profile tires. I said that’s a nice M3, and it impressed him too. I guess Robert never met many women who were into cars. Wait until he saw my little Porsche 911 Carrera Cabriolet.

Robert helped me into his car, and when he started it up, the radio was on the same station to which I usually listened. I told him not to turn off the radio when he reached for it, so he just turned down the volume so we could talk. I told him that I liked that song; it was one of my favorites. We had another chat about music, and we found it no surprise that we had the same taste in music.

We arrived at the restaurant, and we were seated almost immediately. He had the Veal Osso Buco, and I had a Penne Arrabiata. We shared a bottle of Italian red and started with Caesar salads. That we enjoyed each other’s company was an understatement. I was being mesmerized by this man. He had so much depth to his character and intelligence. I kept stealing glances at him, and when he caught me, I would blush. We chatted for so long that we closed the place. I looked around and noticed all the staff was watching us, and we were the only two patrons left. Robert thought it was time for us to go, and I saw him walk over to the head waiter and hand him some cash for their inconvenience. The waiter smiled and told us we were welcome back any time. I was impressed by his gesture.

Robert helped put on my jacket, and we left the restaurant. We walked over to his car, and he told me, “I don’t know what it is about you, Sandra; I have never been more attracted to a person than I am to you.”

“I don’t understand it either, Robert, but I feel the same way about you. It’s like I have been waiting my whole life to meet someone like you, and here you are.”

He opened the door, helped me inside the car, and then got on the driver’s side. I was leaning towards Robert a little as I found the seatbelt; he took the opportunity and kissed me. The feeling was electric; we both moved back in amazement.

“Wow, did you feel that too?”

“There was something there when we kissed each other, so we must study this further.” Robert smiled and said, “I think we will have to try again to be sure,” so we kissed again, this time much longer. We then made out like a couple of high school kids, and it was a lot of fun.

I was breathing heavily and said, “We had better stop before I am unable to contain myself.”

Robert laughed and said, “OK. Where to, Sandra?”

I gave him directions back to my place. After he parked the car, he walked me over to the front door of my townhouse. I smiled and asked Robert if he wanted to come in and have a coffee with me, and he readily agreed and followed me inside.
I turned on the lights, and he followed me into the kitchen. I set up the coffee maker and placed a few cookies out on a plate. We sat down beside each other at the table and just looked at each other, waiting for the coffee.

I smiled at him and said, “You are a great guy, Robert. If I didn’t know any better, I would say we are two people falling in love.”

Robert held my hand and replied, “I felt the same attraction towards you. The last time I felt this way about someone, I ended up marrying her. I want to continue this relationship we have and see where it ends up.”

I just blushed and gave him a big smile. I leaned over and kissed him again.

The coffee maker made its usual noises and puffed a couple of times, telling me the coffee was ready. I got up, poured the coffee into a couple of mugs, and set them on the table.

“Do you like cream only in your coffee?”

He said, “Yes, please.”

I brought a little creamer out of the fridge. I also set the plate of cookies on the table and sat back down, and we both sipped the coffee silently before I looked at Robert and spoke again.

“I don’t want you to think I am rushing things, but I wondered if you would like to stay the night with me?”

I could tell that he was excited, and I tried to remain calm; he smiled and said that would be great.

I leaned in and gave him another kiss. We continued to drink our coffee and had a couple of cookies. I asked him, “Let me give you a tour of my place.”

My home was a three-story townhome on a city lot. The first floor had the kitchen in front; we shared the coffee on a high café table that looked out on the street. Behind the kitchen, I showed him my dining room with the living room beyond. I had a fireplace in the corner, and there was a sliding glass patio door that went out to my deck.

“Downstairs is a family room with another fireplace, a small bathroom and laundry room, and a small office under the kitchen. There is a door at the back leading out to parking space under the deck.”

He followed me upstairs, and I told him this level had carpeted floors, a master bedroom, and an ensuite bathroom. I showed him my little sitting area and a balcony railing that overlooked an open space above the living room.

I didn’t take him up to the third floor but told him it had a pair of bedrooms and a bathroom that I wasn’t presently using. We walked towards the double doors leading into my bedroom and showed him my classic dark cherry French provincial bedroom set. I walked through my closet to the bathroom and showed it to him.

I found a robe that would fit him and handed it to him as we walked out of the bathroom. Excuse me, I must freshen up, and you can get changed in the bedroom. I placed some lube into my vagina, changed into my black teddy, and entered the bedroom. I walked over to the bed and pulled the covers down. I then walked over to Robert and put my arms around him as he got up to meet me. He also put his arms around me, and we just started to French kiss each other. I was so glad he didn’t smoke.

While we were kissing, I slowly led him over to the bed, and we both laid down beside each other. We continued to kiss for a long time, not being able to stop. Eventually, I opened his robe, and his erect manhood sprang out. I smiled, as it was impressive. I couldn’t help myself, but I took hold of it and began to give him a blowjob. I swallowed it down my throat, all the way to his balls. His cock had a wonderful musky smell that excited me even more. In no time, I was pumping him up and down with my lips, and I could feel him starting to tense up. He warned me that he was close to coming, but I kept going. He ejaculated his load down my throat, and I swallowed every drop. As he became soft, I continued to slowly suck on his shaft until I let him fall from my mouth.

“That was great, Robert; you must be at least seven inches.”

He smiled and said, “Eight.”

Then it was Robert’s turn. He moved down on my sex, slowly working his tongue around my folds, exploring as he went. As he worked his tongue down below, he also managed to bring his fingers on my boobs and slowly tweaked my nipples. The feeling in my breasts was electric and made me moan louder and louder as he continued to use his tongue to probe me deeper. His tongue worked over my clitoris and sent me over. The orgasm wave crashed over me, and I began to convulse. He didn’t stop and continued with his incredible-feeling tongue going deeper into my vagina, and the orgasm wave was building. I began to shake again and orgasmed a second time.

I needed a bit of relief at that point and placed my hand on his head and said, “Please kiss me.”

Robert worked his way up my body, and we started passionately kissing once more. Robert had stamina; as he kissed me, I could feel his manhood become stiff again, and he entered my vagina as we kissed, slowly probing deeper into me. Robert began to pump me a little faster, and I kissed him with even more passion. He was a master with my nipples, and I tried to scream while we were kissing. I convulsed again as the wave crashed over me. Robert responded by pumping even harder, and I felt him begin to tense up, and he came inside me, just as another orgasm wave crashed upon me for the fourth time.

He slowly pulled out and smiled, “How was that?”

I was breathing heavily, grabbed him around the neck with my arms, and kissed him further, as passionately as I could.

I was lying there in my orgasm afterglow. Robert had put me into shock and awe. I turned my head to look at him. “Where on earth did you learn to do that to a woman? I have never had any man do that to me.”

“Well, my wife wasn’t a big fan of my dick, and she rarely let me have sex with her that way. I eventually learned how to please her in other ways with my tongue and hands. What you did with Mr. Happy was terrific as well; she would have never done that for me.”

I laughed and said, “It wasn’t hard to sexually please a man; you only had to be willing to do so.”

We both slowly fell asleep as we embraced each other.