Accidental descent into femininity

Chapter 1 Background and Recap

I have decided to write a diary, to document what is happening to me. I will have to recap from when it all started, but I am thinking of potentially publishing it anonymously on a TG site. I am hoping in writing this, that others will benefit from my weird life. Anyway, lets start with the recap and probably best to include a bit of background info.

I can't say too much about myself or I won't be anonymous. I was born clearly male, and I do not think I had ever been mistaken for female. Growing up I realised that I was different to the other boys around me, I didn't like what they did, understand their attempts at one-upmanship or communicate on anything other than a superficial level. I kept to myself and read a lot. Fortunately or unfortunately, depending on how you look at it, I always carried extra weight, enough to be heavy, not enough to be the fattest in the class. So although I got teased a bit, bullying was pretty rare. Sexual orientation was clear cut for me, I fancied women, the problem was, almost every woman I met, I got on with, but they immediately put me in the friend category, not boyfriend material. They would cry on my shoulder, telling me what idiots (and worse names) men were, ignoring, or not being attracted to me or other nice guys. I refused to become a bastard to try and attract women, and lets be honest, I didn't look all that manly. I'm 5”7, I look stocky, but most of that is fat, I have small hands, small feet, no visible Adam’s apple, the only obvious manly feature is my facial hair. I shave once a day and have a 5 O’clock shadow before lunchtime. I didn't dress very well either, looking back, I realise that I never liked my appearance. I particularly didn't like the hair everywhere. I could have done something about it, but it cost a lot and was never a priority. I met my wife on a dating site, married 2 years later and had two beautiful kids. Enough background to get started, I will add more later if I feel my unusual story needs it. Now the recap.

6 months ago, I was walking quietly on the beach. The beach was mostly deserted, just a few people walking their dog or pushing a pram. There was one man fishing. He was sitting some way back from the water, his pole was quite high, with a line presumably dropping as it got closer to the water. I say presumably because, although I knew it was there, I could not see it.

I was about 200m away when the accident happened. A young mother was jogging pushing a big 3 wheel pram, her focus on the child in front of her. From my distance it looked like she stopped suddenly, possibly even thrown back, and dropped to the floor clutching her neck, the pram continuing on for a few metres before stopping too. I rushed towards her, but a couple walking their dog and the fisherman got there before me. The fishing line had cut deeply into her neck and there was blood everywhere. The man was on his phone calling an ambulance, his partner had released the dogs and was trying to put pressure on her neck. There was nothing more I could do, so I wondered over to the pram. Inside was a beautiful baby girl, who couldn't have been more that a week old. She had woken up and was clearly getting ready to cry. I pulled her out of the pram, put her on my shoulder and started to try to sooth her.

Shortly the paramedics arrived and with real urgency rushed the lady off. Everyone but me seemed to have forgotten about the baby, or perhaps, seeing someone taking charge of the child, either thought she was mine or I knew her. She had fallen asleep on my shoulder and seemed content. I found out which hospital the woman was taken too. I decided I needed to follow and find out who should be taking care of the baby.

I phoned my wife, explained what had happened, suggested she pick me up. We didn't have any baby seats any more as our kids were seven and eight. Fortunately, my wife, Sarah, phoned a friend, Wendy, who had one, and agreed to pick me up instead. By the time I had got to the hospital, pram, baby and all, Sarah was already there and she had sad news. The lady had died en route. We explained our situation to the reception staff. I believe they called the police or child services. It wasn't long before a police lady approached us and told us that the partner of the deceased was identifying the body and would be back shortly and could we look after the child a bit longer. Sarah had to leave to pick up the kids from school. We arranged for me to call when ready and they would all come and pick me up.

I ended up going to the maternity ward, borrowing some supplies and trying to convince a very reluctant baby to go from breast to bottle. In the end, I doubt we managed to get more than a few dribbles in, but it seemed to satisfy her, at least temporarily, and she settled back to sleep. I noticed, when I placed her back in her pram, an older gentleman had been watching me. I had been so focussed on the child, I have no idea how long he had been watching, but when he saw me acknowledge him he came over.

“Hi, I'm John, and you are?”
“Kelly, pleased to meet you.” I replied.
“You seem very good handling babies.”
I smiled a bit awkwardly, I know it is unusual for blokes to be as comfortable as I am. Once you are over 40, you care less about appearances. “I love babies. I am a father of two and would have loved to have more, but my wife really struggled with the pregnancies.”
“Interesting.” he said with a thoughtful look on his face. “Look, we will need to have a chat in a few minutes. I just need to make a few phone calls.”
“OK.” I said a bit confused. I did not know why we needed to have a conversation, and considering he looked about 60, I certainly didn't realise he was the father until he came back 15 minutes later.

“We need to discuss what is best for my daughter.”
“Oh, right.”
“I have a proposal for you. I probably need to explain a bit first.” He pulled a chair round so he could sit comfortably facing me. “I suppose I am somewhat the opposite to you regarding children. I have zero interest, and definitely didn't want any. In my first marriage, we had three, and I discovered just how bad a father I am. I pretended as much as I could, but I had no real connection. To be frank, all they did was irritate me and give me less time with my wife, which further irritated me and ultimately led to my divorce. This time round, Elaine” he paused to gather himself, I could tell he swallowed an emotional response, “she gave me an ultimatum, no sex with contraception. Maybe that is too much information, nonetheless, I explained to her, my previous experience, and she promised that any children would be totally her responsibility emotionally. All I had to provide was financial support. She also said she was willing to use nannies so she would still be there for me. She was an orphan and I think emotionally wanted to give a child all the love that she had never received. Anyway, here we are, I have sole responsibility for a child that I have no desire for, no connection to and no ability to deal with. So, as I said, I have a proposal.” He looked at me, waiting for a response.

I just nodded my head for him to continue. I didn't see where he was going with this.

“I want to hire you, no that's not quite right. The baby was born in this very hospital, we have not sent off the paperwork yet, so we have an opportunity. For a price, I'm thinking $200,000 a year, guaranteed for 20 years, I want you to be on the birth certificate as the father, her name has not been decided yet, so you can choose it. You will have full responsibility. I will not have the opportunity to muck up someone else's life. I will never contact you, You will never contact me.”

It took some time to gather my wits. Looking back on it now, I probably would have agreed without any incentive, Emma, as we decided to call her, already had me wrapped around her little finger. Of course I had to include my wife in the discussion. She negotiated an increased income to $250,000 a year, he countered by insisting that I give up work and we also ended up with Elaine's new car, a red Tesla with baby seat already fitted. The funny thing is my wife is a strong believer in 'The Secret', and had been visualising and doing affirmations asking for $250,000 a year passive income and a, you guessed it, red Tesla.

All we had to do was maintain the fiction that Emma was my child, telling everyone, we had helped out a single woman with a sperm donation and the mother had an unfortunate accident. We could claim there was an insurance policy. A lawyer came round the next day, lots of signing later, we were the proud parents of a beautiful baby girl. Later that same day lots of boxes arrived which contained not only everything a rich family would buy for a new arrival but all of Elaine's stuff. We left all of Elaine's boxes in storage and prepared our house for our new child.

As any new parent knows, babies may be beautiful but they can also be hard work. Emma was no different, and her trouble was with going from breast to bottle feeding. She started becoming upset before we even got back from the hospital. I could tell she was hungry and I was trying every trick I could think of to get some milk in her. We tried all the different brands of newborn teats, various different brands of milk formulation and holding her in different ways. As the night wore on, with little success, I was getting more and more agitated, feeling overtired and concerned. My wife was asleep in bed and I was downstairs doing my best. In desperation, I came up with a slightly crazy idea. As I mentioned before, I was somewhat overweight, maybe more than somewhat, anyway the result of that is I have noticeable man boobs. My plan was to prepare the milk, allow the baby to suckle on my man boobs and use a dropper to add milk by sliding in between me and her mouth. Laborious, I know, but as I said I was getting desperate.

First off, I have to say, respect to all women who breast feed, the suction Emma could create felt like industrial power. My nips, I am guessing are not as sensitive as a woman's, but still they felt uncomfortable almost immediately and were sore in minutes. As I said earlier, I have already watched my wife go through the process with my two children and knew, one session could typically take up to an hour. Success. The milk was definitely going in, but slowly, I had to dribble it rather than squirt it and manoeuvre the dropper so that I did not break suction, both putting it in and taking it out. Within 10 minutes I had to change sides, as it was just too painful, and my hairy chest did not help either. She was clearly still hungry after another 10 minutes, so I had to switch back again. OMG, sore nips being suckled again after only a 10 minute break, well let me say, respect. I didn't last another 10 minutes, maybe 8, before switching again, with a successful burping intermission. Finally, she didn't seem to want any more, but she still kept sucking, I think just for comfort. I was struggling with the pain involved, but managed to gently pry her loose and rest her on my chest. I was exhausted, grabbed a blanket to cover us and was out like a light. What felt like moments later I was awakened by a sharp pain on my chest. Three hours had passed, Emma was hungry again, had managed to find my man boob and the industrial hoover was back. I had to get up anyway to make more formula, so I changed her nappy and tried the bottle again. No way hozeh, Emma would only take it one way.

Thus started the two most uncomfortable weeks of my life. I pleaded with my wife to take a turn, just to give me a bit of relief. She laughed at me, which I thought was a bit harsh, but said she had already had two turns and this one was mine. Apparently, I needed to man up, maybe she meant woman up. At the end of two weeks I was coping much better, Emma was putting on weight, although my nipples and whole man boobs, actually, stayed swollen, puffy, itchy and slightly red.

When I realised I was going to be doing this for a while, I knew I would have to do something about my chest hair. I tried shaving it, but it grew back fast. My main alternatives were to wax or laser. Waxing would be painful, and to be honest, considering the pain I was enduring at the time the thought of more pain anywhere near that area, made me quickly dismiss that idea. Laser sounded less painful but obviously could be a permanent result. I discussed it with Sarah for her opinion, and she surprised me by saying she liked the hair free chest look, in fact, touching my smooth soft chest was a bit of a turn on for her. She considered hair to be a bit unclean and the only place she personally liked it was on her head which did reflect her personal grooming. She particularly didn't like kissing me with scratchy stubble, or getting hairs in her mouth if she was kissing me elsewhere, which I figured, explained why she almost never kissed me elsewhere. This made me seriously consider having other areas done at the same time. To understand how seriously we are talking about, and without getting into too much detail, since our second child was born, the difference in my sex drive and Sarah's was substantial. Anything that would encourage more intimacy was always going to be a priority for me.

I was anxious when I went for my first appointment because I wanted to discuss hair removal on other areas and I was getting embarrassed about even the idea. Funnily enough the lady who I met for my first appointment, Sharon, made it really easy for me, but also even more embarrassing. Having seen the redness and irritation around my nipples and a shaved chest, she assumed I was taking female hormones and wearing breast forms. I was left with the option of explaining that I was allowing a baby to suckle my moobs, or let her believe that I was in transition. I don't know why I felt so embarrassed, I mean, I wasn't doing it for my sake, but I just couldn't bring myself to admit what was happening. Then once you go along with a lie, you can't easily back out. I had to sort of pretend that I was wanting to look more feminine. I sort of felt bullied, admittedly by someone who was only trying to be helpful and whose heart was in the right place, into agreeing to have pretty much all my body hair and face treated. My arm and leg hair had never really bothered me, but since I am dark haired with relatively light skin, it does stand out, so how do you say no, I don't want it removed? No one transitioning would want my hairy body, and to be honest I wasn't that bothered if it went, so I just went with the flow. The process was also embarrassing so I also knew, I wouldn't have the courage to go elsewhere and start again. Oh well, hairlessness, here we come.

Chapter 2 Week 3

I went to the GP this week, not for the baby this time, but for me. I started noticing wetness around my nipples, even when Emma wasn't involved and I think my nipples are bigger, possibly even my breasts are too. According to the GP I am lactating. Apparently men can also produce milk and suckling can stimulate them to do so. A hormone is released during suckling that encourages it. The milk is the same as what a woman would produce, and is better for the baby than formula, so I have been strongly encouraged to continue, but discontinue the formula. At least it is not painful any more, in fact, I feel an enjoyable emotional connection when I am doing it. She also suggested I might be more comfortable if I started wearing a bra, a maternity one obviously, as if. Good news, when Emma stops suckling, the milk stops, yeh. At least, I don't have to faff about with the dropper any more. I also am losing weight. I reckon that's related to producing milk. I know when Sarah breast fed she lost the baby weight quickly.

I went for another hair removal session and I guess I am not imagining it, Sharon commented on my increased breast and nipple size. I was a bit frightened of leakage and then having to explain, but Emma completely drained me so no problem there. I am not sure I can get any more embarrassed in front of Sharon, this time when she was working around my nipples, my downstairs got a bit excited. I very deliberately avoided any eye contact and she ignored it. Thank God she is a professional. Only 2 more weekly appointments then it is only 1 per month.

Week 4

I am getting a bit worried now. I seemed to have lost 10kg. That sounds great, and I don't want to be ungrateful but losing weight, really makes my increased breast size stand out and I am sure it is bigger again. Sarah reckons I am approaching C cup and really should be wearing a bra. I am trying to avoid it but leaking into T-shirts looks crazy wrong. My nipples are way more sensitive now and wearing anything not soft enough drives me crackers. I am using my losing weight as a reason to not buy anything yet, but I know she is right, very shortly, I am going to be a bloke in a bra. I am already a bloke that breast feeds. Nobody outside the wife and kids, the doctor and Sharon know about any of this. You can't get a 7 and 8 yr old to keep this type of secret. Even if they did I would have to become a hermit and never leave the house. Actually that sounds quite attractive at the moment.

To make matters worse, my junk is shrinking. It was never that big to begin with. It's fortunate that I am good with my hands. Sarah isn't interested in sex very often these days, but I think she is fascinated with my changes, hopefully in a good way. She definitely loves the loss in weight as, although she has never mentioned anything about my excess, she is praising like crazy this reduced version. She started caressing me in bed. For the first time ever, my wink was not responding. Strangely, I did not mind, as what she was doing felt great and I used my hands, tongue and a vibrator to make sure she had a great time. I also felt more emotionally connected afterwards, which I don't understand.

As I mentioned before, my sex drive has always been quite high compared to my wife's, so I was compensating by relieving pressure myself, so to speak. Almost without realising it, that has almost completely stopped. Even trying is not getting me very far. I also, just don't feel the need. On the plus side, soaping my breasts in the shower, has given me such joy that I don't really mind. I was cleaning them, and was surprised by how good it felt, so I went past the excuse that they needed more handling and admitted they just felt great to touch. I imagined I was touching and kissing my wife and that it was her hands caressing, squeezing and even gently pinching my nipples. The sensation just built and built and then suddenly I felt this explosion of pleasure that came in waves. I literally cried with delight, which has never happened to me before. I would call it an orgasm but it lasted longer than any orgasm I have had previously, my little fella was only half interested and nothing came out of it.

Although it was a bit embarrassing I talked it out with Sarah, I figured I shouldn't keep anything from her and any decisions we made, should be made together. I wondered if the right thing to do was stop breast feeding so that some of my changes would reverse. She first concentrated on what happened in the shower. Instead of a one or two sentence mention, she wanted a full and complete description. I may have misread the signs, but it looked to me like she was getting turned on, so I tried to be as descriptive as possible. She was smiling big time at the end of it. She wistfully admitted that she didn't react that way to her breasts, but she knew one of her girlfriends that did. Then she got a serious look on and got me to write down all the positives and all the negatives, including what she called a mind blowing female orgasm. She suggested that I add to it over the next week and then we discuss it.

Positives: Great pleasure from breasts. Feeding Emma the best food available. Losing weight. Bonding time with Emma.

Negatives: Looking half way between male and female. What people would think. Shrinking genitals and inability to use them with Sarah.

Week 5

The weight is still falling off. My breasts are still growing, but a bit less quickly. Sarah is a C cup, and I am pretty sure I am a bit bigger than her. I am not sure how I feel about it all. First off, walking without support at that size is just not comfortable. I know I am going to need to start wearing bras and I know the best way is to go to a shop and get measured properly, but I am struggling to generate the courage. I can't keep complaining about it, Sarah has stopped saying anything, she just gives me the look. I have surreptitiously tried one of hers but they are too small.

Secondly, I am getting rather attached to them. They are majorly messing with my life, because they are just getting so obvious, but I can't help liking the look of them. They look great. There, I admit it. They look great, and when I see my breasts, they make me smile. When I look down and see Emma feeding, I feel such love. Now I am worried about my chat with Sarah going over positives and negatives. I don't want to give them up and if she suggests that, I'm worried that I will burst into tears, I am feeling so emotional about it all. If I can just get over the embarrassment side of things.

Sarah surprised me today. Maya and Bex our 7 and 8 year old beauties, had great fun playing with Emma who is staying awake for longer periods now, I had a shower in our ensuite after a posetting accident. I think I produce too much milk and Emma likes to suck for comfort and ends up being overfed, so regurgitates the extra. This time the bib had shifted so I ended up covered in it. Anyway, I started having a shower and Sarah joined me. She wanted to make my fantasy a reality. OMG. When she started caressing me, my knees literally went weak. I thought that was just fiction, but no, we ended up sitting in the shower as my legs could not support me. I tried to touch her as well, but she said this was all about me, and if I moved my hands towards her core, she gently moved them away. Touching her while she played with my breasts and kissed me, blew my mind. I have never had anything like that before. When I hit that peak again, my legs were shaking and I was gasping. OMG. Again wink was mildly interested and there was no fluid. Weird but oh so satisfying. You couldn't get the smile off my face and although Sarah obviously didn't get to the same place, she was smiling almost as much.

That night Sarah approached me for a talk. The reason why she wanted to leave it a week with the positive and negative thing was she wanted to see my female orgasm as she called it before we had our discussion.

She started by looking deep into my eyes with a very serious look in hers. “Kelly, what is happening to you and what you decide to do, could have serious consequences for our family, possibly, for a very long time. I need you to be completely honest, don't hold anything back. Don't worry about what I might think, or about hurting me. You are not me, and making guesses about what I feel could have disastrous end results.” She took both my hands in hers and gave them a squeeze. “Please tell me the truth.”
“OK” I knew what she meant, if I was embarrassed or worried how she might react, my tendency was to soften what I was going to say.
“Lets go through your positives and negatives.”
I had come prepared and on the table next to us was my small list. I released one hand and picked it up. “Well, which would you like first?”
“The positives look great, lets go through the negatives, alright.” she said, maintaining this intensity.
“Um, well, er, I am getting scared of looking like a freak. I mean if I look both male and female, everybody is going to be judging me and staring at me and making me uncomfortable.”
“First of all, I don't think you look like a freak. Do you care what other people think? I mean I have had to nag you to put better clothes on, so you didn't look like a homeless person. You have never really cared before.”
“I usually don't care. OK. Brutal honesty, I think everyone cares at least a bit. I tend to care less than most people, although what you think really matters to me. Gender is such a strong issue, people have so much bias, the idea of going out looking clearly like a feminised male is scaring me.”
“We'll come back to that, I have some ideas that might help, depending on....” She paused deciding on going to start a different conversation. “Lets shelve that for a sec and move onto the last item. Leave me out of the equation regarding me having fun with them and tell me how you feel that your privates are getting smaller.”
“I don't know if I can leave you out of it.” I had to hold up my hand to stop her from interrupting. “Look, I know I have never been very big in that department, but I feel less manly when they were not involved in our lovemaking. And maybe worried that you see me as less.”
“I think it might be time for brutal honesty from my side.” she said. “Actually, before I start that, I just want to say the last two lovings have been the best I think I have ever had.”
“The last two?” I was trying to think back, as we had only made love once recently.
“Yes, I am including the shower today.”
“Oh.”
“I know, the male view is it is all about the orgasm, but for me, the emotional connection and how I feel afterwards, is what I care about.” She paused, keeping eye contact. “Be honest, how would you rate them?”
I felt the urge to look down, but forced myself to keep looking into her caring eyes, She was looking a bit vulnerable. “Awesome.” I said in a small voice.
Her smile lit up her face. “Great, now we are getting somewhere. Forget how you think I should feel about it. My brutal honesty, I don't care how big your wink is, or even if you have one. If you look back, I have never had an orgasm from penetration alone. What you can do to me with your hands, rocks my world, baby. I am never going to think less of you for the size of your penis. My previous experience suggested the reverse. The men I met with big willies were so selfish and just presumed I would have a great time if they could just fuck me. Emotionally it left me feeling less, whereas with you, I feel loved, cared for, more. I was worried how you felt about it, but after our shower experience, I'm not anymore. The reason why I am asking for truth, is because I know society has certain opinions, and I thought you would hesitate to give me anything outside of that. I know you read transgender books and I know most men would be completely freaking out in your situation. I love you for you, male, female, other. I want you to be happy regardless of what others think.”
I took a few moments to really think about what she had said. I knew I had to be honest, really truthful. “I don't want to stop. I don't know why but I like my breasts and you're right, I know intellectually I should be terrified of what is happening to my stuff. Really, I'm just, not. What does frighten me is everybody else seeing me. I want to not care, but I am scared.” I started tearing up, managing to hold it mostly together until Sarah hugged me which kicked off full on sobs. She sat there stroking my hair, cuddling and murmuring soothing nothings as I gradually calmed down. For some reason, I felt much better.

“As I said, I have some ideas. I need you to trust me. Are you worried about strangers or people we know?”
“Both”
“OK, lets start with people we know. Is it my friends, your friends or family?”
“I'm not worried about my family, it will be awkward and embarrassing, but they love me and will accept me.”
“Again, I'm not trying to hurt you. What friends of yours are you talking about?”
I had to think about that for a second, I really didn't have a lot of friends. We had moved away from home and when I stopped making an effort to keep up with my supposed friends, they didn't bother contacting me. “The guys I play squash with.”
“Are they really friends? I mean do you know their wives names, their children, even what jobs they do?”
She was right. We call anybody not an enemy a friend, but there is a scale, and nobody I knew was a close friend. She didn't wait for me to answer before dropping a shocker. “My friends already know.”
“What!”
“I'm sorry. I am so proud of you and what you are doing and you know we girls talk about everything. I couldn't help myself. You get on with all of them and they like you. This hasn't really changed how they look at you. They are all accepting, in fact they want to help.”
“Help me how?”
“They have offered to help, I haven't suggested anything yet, but they have offered.”
“They just want to see what I look like.”
“Don't be like that. I am sure they are curious. Not nasty curious. I think their offer was from a place of love. I haven't invited them round as I didn't think you were ready for that yet.”
“I'm not.”
“You are going to have to face some of your fears. Maybe they are a good first step. If you can face them, it might lessen your other worries. You can't bury your face in the sand, forever. Something else you need to face. Darling, you desperately need to start wearing a bra. I know you are still changing shape and you are scared of going to the shops. How about I measure you, and try and find something suitable, until your body has settled and your mind is calmer and we can do it properly.”
She rushed off and came back with a tape measure. Without explaining, she measured me everywhere. By the next day I had my own, fairly well fitting, maternity bra with pads you could place to soak up any accidental milk leakage. Obviously a bra is designed to support, by doing that, my breasts were even more emphasized.

Chapter 3 Week 6

I feel like I am turning into a recluse. I need to get out of the house. I have made an appointment with my GP later in the week. I have gone from 100kg to 65kg in only a few short weeks. None of my clothes fit me anymore. My tops are like tents with two poles sticking out. My waist is what has shrunk the most and my belts have run out of holes, so I am stuck in track suit pants. I look in the mirror and I see a man's head on a woman's body shape. I have even got the in and out curves suggesting hour glass shape. So, man's head, women's body and really bad fitting clothes. Sarah has suggested going out for various reasons and I keep on making excuses. I am thinking of cancelling my GP appointment, despite knowing I need some investigation, just because the thought of sitting in the waiting room looking like I do makes me feel terrible. I haven't done it because I intellectually know that is not a good enough reason. Sarah can see me struggling and has offered me all the love in the world, which helps. I just wish it would take my fear away. She has told me when she gets back from dropping the kids off and Emma settles for a sleep we will have another talk. On the Emma front, I have to say, she is a dream baby. She only really cries when she is hungry and at night I am getting almost 6 hours in one stretch now. I am pretty hairless now, and my next appointment with Sharon is not for 4 weeks. She was really impressed with my changes, but suggested I start dressing better. She was nice about it, but it still made me feel bad.

Sarah started our conversation in a direction I was not expecting. Again she positioned herself so that she was facing me, keeping eye contact and holding my hands.
“I am going to ask you some difficult questions. Before I do, I thought I would tell you something about myself that I find difficult to share.” She broke eye contact briefly. “I've never told anyone this.” I squeezed her hands in support. “When I was a young teenager, I seriously thought I might be gay. I had a crush on this girly girl in my class, Stephanie. She always dressed so cute, was always smiling and developed early with great assets. I had lots of sexual fantasies, lots of self-doubt and guilty feelings. I never approached her, I was so scared of being rejected. She clearly liked boys and was always crushing on one or another. As I got older I started being interested in boys. I have never lost my attraction for girls. Even though I was attracted to both, I knew it would be easier to stick with what society prefers. Most of my experiences with dating men have not been good ones. Before I met you I was seriously thinking of trying the other side. You were so different to any of my other relationships. I love you so much. Now your turn. You started reading transgender books, I know, I know, they have some great stories. Most people will enjoy books more if they relate to them. Do you think you could be transgender?” She squeezed my hands and stared earnestly into my eyes.
I closed my eyes for a second saying to myself, honesty, brutal honesty. I opened them and smiled slightly. She accepted me for who I am, whatever that might be. “Maybe. I wondered about it. Some things fit and some things just don't.” She nodded her head gently, encouraging me to continue. “In the stories most transgender individuals know what they are from a young age, I have never had that. They also talk about this compulsion to dress and look like a girl. Again, I don't have that desire. I sort of dismissed it at that point, but still wanted to read more stories. Then I came across a story by Karin Bishop. The main character had no clue that he was really a she until a friend forced or encouraged her to see herself in a different light and then her whole world shifted. Up until that moment her life was very similar to mine, you know, not really getting on with guys, sort of getting on with girls, reading a lot. I wondered if that meant I could be the same.” I took a deep breath, repeating to myself, total truth. “There are some online tests you can take that can are supposed to tell you if you are emotionally male or female.”
“And?” Her look was still supportive and loving.
“It suggested I was emotionally female with the suggestion that I try dressing as a woman.” I paused again after what felt like a huge revelation, but was at the same time anticlimactic. Sarah now had a big smile, which really helped. “I considered it, but again had no desire to try your clothes on, plus, in the stories the protagonist when dressed and made up looked beautiful and no one could tell that she had ever been male. Real life here.” I pointed to my face. “I would be clocked with one look.”
“Thank you darling, I know that was hard, but I don't entirely agree with you. Before you removed your facial hair, maybe, but now, I don't think so. Look, everyone is their own worst critic. Tell me, from your reading, what features generally give the game away?”
I thought about it. “Well, large hands and feet.”
“Which you don't have.”
“True, ah, visible Adam's apple.”
“I can't see yours.”
I brought my hand to my throat. My Adam's apple has never been very obvious, but I thought that was because of the excess fat. Now most of that was gone, I expected to find it, but I couldn't. “OK, ok, facial features, male pattern hair loss, pitch of your voice, er, how you walk, move, hold yourself.”
“Lets talk about you specifically, so facial features.” She took my hand and pulled me to a mirror. “What about your features do you think suggest you are male? When you see yourself, you naturally identify yourself as male, but that is habit more than reality, so I know this is hard, but imagine you are looking at somebody else, what features?”
Looking at myself critically, I thought my eyes looked a bit small, but that is to do with beauty not male or female. I didn't have a particularly male jaw. “My nose is too big, my hair recedes too much, especially in two places that is a male pattern.”
“I think that is sort of true.” I turned to face her, thinking, now who is not being truthful.
“Come on, honey, I am being as honest as I can. I am not wrong.”
“Yes and no. First of all, all women have features that they like and some they don't. That is where make up comes in. Skilfully applied it emphasizes and downplays features. Your nose is not large, amongst my friends, Karen has a nose at least as big as yours. Society considers a smaller nose more feminine, which is why so many women have nose jobs, but we are not all born with pretty noses. Your nose might make you look less pretty, but it does not identify you as male.”
I considered what she said, trying to find fault.
“As far as the hair is concerned, your hair style could completely hide the receding hair line. Lots of women also have that issue. I don't have any friends to point to, but I have seen it in magazines and ways of minimising it.” We went back to the sofa. This time she cuddled me. “As far as I can see, your fear is looking neither male nor female. Well, lets be honest, you can no longer pull off the all male look, so I think we need to try the all woman look. Just think about it and we'll talk more tomorrow.” We stayed cuddling for a while in a comfortable silence.

The next day knowing that we were going to be talking about something I found so embarrassing, my anxiety levels were sky high. Probably because of that it took me a bit longer to settle Emma for her morning sleep, but eventually she dropped off and I ended up back on our serious conversation couch with a broadly smiling Sarah.
“OK.” she stretched her hand to rub my thigh. “Stop stressing, this is going to be fun!”
I didn't say anything but my eyes were saying 'easy for you to say'.
“Lets start with a bit of philosophy. You know I have studied lots of self-help books. Most of them agree on some principles. What you think affects the world around you. Essentially you attract to you what you think about most or most strongly.”
“Are you saying this has happened to me because I wanted it to happen?”
“No, its not about what you want, its about what you think or what you have been thinking. Of course the idea is, if you can control your thoughts, you get to decide what you attract. Or as I like to think of it, be happy, think happy thoughts and happy things will happen. What I really wanted to say was, LIVE YOUR TRUTH. If something makes you happy, don't let somebody dictate what you should or shouldn't be doing. That includes me. Now if you haven't tried something how can you tell if it will make you happy or not? I want you to trust me. I am going to take you on a journey and if at the end of it you can honestly say it is not for you, fine, I won't push or coerce you. I do want your co-operation, so, no talking, no complaining, no saying what will other people think. Can you do that?”
I was wondering if that was a trick question so I mimed zipping my lips and locking them. She took my hands and led me to our bedroom. The mirror on her vanity was covered over. On the bed was a set of clothes, female clothes, but nothing ultra feminine. “Strip and get changed. I'll help.” While I undressed she held up a pair of panties, just plain cotton panties, I guess she did not want to overwhelm me. I was already wearing my maternity bra, so I left that on. There was a white blouse, very similar to many shirts that I have previously worn, but buttons on the opposite side and shaped to accommodate my enhanced front. It was also a perfect fit despite my weight loss. When she measured me for my bra, she did a lot of other measurements obviously with this in plan. Next was a pair of jeans and a belt. The jeans had purple stitching on the pockets to give it a hint of girlishness. They fit very snug and stretchy, very different to any I had worn previously. They were quite tight at the front and if my junk hadn't shrunk I think they would be uncomfortable. It was strange, I was wearing very similar clothes to what I would normally wear but the cut was totally changed and now felt like it fit me properly. Even if I was allowed to talk, I don't think I would have objected to anything. Next I was sitting at her vanity while she worked on me. I have never had make up on before, not that I can remember anyway, so it was a very surreal experience. She did not say anything while she worked on me but there was a look of concentration. I didn't really like the feel of make up on my face but I loved the intimacy with her working on me so closely. Then she came back with a wig with very dark brown hair, very similar to my natural hair colour. She attached it very firmly and then brushed it out to her satisfaction. I thought she was finished, but she was looking with a frown on her face.
“I am sorry, babe, but I think we need to do your eyebrows, they are too bushy and uncared for. Is that OK?”
I figured, in for a penny, in for a pound, so I nodded my permission. She used a trimmer and a comb to reduce the bushyness and then plucked a bit.
“I'm not going crazy with this, if you like the look we will go to a salon and get them done properly. Do you want me to do your nails?”
I shook my head.
“Turn around, I'm going to uncover the mirror.”
I stood up and turned around. I have to admit, I was expecting to see a clown so when I turned under her guidance to see myself, I felt a shock all the way to my core. The person in the mirror was clearly female. Not the most beautiful, but there was nothing male that I could see. I had to sit down. I felt this emotion rushing up like an electrical storm, I had difficulty breathing, but it wasn't a bad emotion. I started smiling, I couldn't seem to help myself and as I did, my face lit up and there was a kind of beauty there.
“I think, honey, this is your truth.” And I couldn't disagree.
The rest of that day went by in a haze and every chance I could, I looked into the mirror and stared at myself.