Briana, The Sissy
“Do you know why Nancy’s boyfriends call you a sissy, or a faggot, or a panty boy? It’s because you are one. You are a little feminized sissy”
It was Friday morning and I was sitting in the doctor’s surgery waiting to be administered my weekly dose of estrogen and my three-month shot of Depo-Provera, which is the drug which chemically castrates me. I have been on Depo-Provera for the last three years and I could tell the last dose was wearing off as my mind was increasingly focused on submissive sexual fantasies. Nevertheless, Friday is my favorite day because I have begun to view the estrogen shot as my weekly fix which leaves me in a dazed, confused but fairly pleasant state for the following few days. The hormonal rushes are always strongest on Saturday morning and I often wake up covered with sweat because of the hot flashes. I enjoy them immensely and they are accompanied with waves of feminine thoughts. My nipples are always on fire for a few days after my shot but the swelling makes me want to touch them continuously. I can’t keep my fingers off them and have often been caught playing with them over my top in public. Now my breasts were growing and it was impossible to hide that.
I was deep into a fashion article when the receptionist approached me and directed me into one of the examination rooms addressing me along the way by new feminine name, Briana. When I followed her in she told me to undress completely and wait for the doctor. She left and locked the door behind her. Since I have started the hormone treatment I have become very body-conscious and feel completely humiliated without my clothes on. Even my wife, Nancy, hasn’t seen me undressed for three years or more. It had been well over a year since, Helen, my doctor and my wife’s closest confidante, had examined me and I was a bit confused as to why she wanted to inspect me today but I did what I was told and kicked off my flats, took off my leggings, rolled down my knee-highs, slipped off my elastic panties and lifted off my velour top. I was standing in the room nude, not knowing where to sit, when the door unlocked and the receptionist entered, holding a hospital gown. She looked startled to see me nude and I could see her glance pointedly down to my penis and balls and could see a smirk growing on her face as she thoroughly examined what three years of estrogen treatment does to a man’s equipment. She could barely stifle a laugh as she handed me the gown and turned to leave the examining room. Naturally, the gown was a shade of pink far lighter than the deep red color my blushing face was.
After I put on the gown I looked around the room and saw my medical file on the desk. I noticed that my registered name on the NHS roles had been changed to Briana and under the sex of the patient no box had been ticked but a notation had been written under saying ‘sexuality is a work in progress’. I was just about to open the file when the door clicked behind me and I quickly took a seat next to the desk. This time it was actually Helen, who was dressed in a customary white doctor’s jacket over a tweed knee-length skirt and a purple silk top. She was in her customary heels which gave her the height advantage over me. I am often struck by how attractive and sexual Helen is. To get a sense of what she looks like, the best comparison would be a blonde version of the Hollywood actress Angie Harmon. When I rose to greet her, Helen gave me an air kiss on both cheeks and told me to sit, naturally addressing me as Briana. Except on the occasions when I call in my bank’s customer service line to inquire about my account, nobody has called me by my birth name in years. I find it shocking when I receive an invoice in the mail or a council tax bill addressed to my original name. As soon as I began my hormone treatment my wife started calling me Briana and everyone else has followed suit.
To be honest, it would be disingenuous of Nancy to describe me as her husband, which would imply that I was still 100% male and there was some sort of sexuality in our relationship. Nor would it be appropriate for her to say I am her wife. Given that our sex life only lasted a few months subsequent to our marriage and, during that time, it was fairly infrequent given that she had other lovers who could provide her with far more pleasure than I could, it would be appropriate to say our marriage, in the traditional sense, was over long ago. Now Nancy just calls me Briana and no longer refers to me as her spouse although she will admit to marrying me some five years ago. Regardless, she still expects me to take care of her, the house, the bills and provide her with the funds to live the life she wants to live.
When Helen took the chair behind her desk and opened my folder she studied it for a moment with a thoughtful expression before she addressed me. I brushed my shoulder-length blonde hair back from my face while I waited for her to speak.
“You must be wondering why I told the reception to tell you to disrobe today,” she said, barely glancing up at me. “I have your completed blood work from your last examination and your hormone levels are rising but not at the progress I would like, so I would like to increase the dosage we give you each Friday and put you on a daily dose to keep levels stable during the week. You will experience more of the hot flashes and body rushes but they are just symptomatic of the gender reassignment you are undergoing and they will continue indefinitely. I also have to make a confession to you. The last Depo-Provera shot I gave you was just a placebo; actually a simple saline solution. I wanted to examine you today to see if we can finally take you off that treatment. I personally think that it is redundant. The original intent was to nullify any jealousy or inadequacy you might have felt from trying to compete with your wife’s lovers but I think the hormone treatment you have been undergoing is more than adequate for that.”
Helen paused for a second and looked up at me for a few seconds before she rattled off some questions.
“Have you noticed any changes in yourself in the past few months?” she asked. “Do you resent your wife for having lovers or feel you have to compete with them? And, finally, how do you feel about the lack of sex of any kind in your life and, if so, what do you think can be done about that? You are only 25 years old so there must be some remnants of sexuality in you, even after the hormones.”
I was initially taken aback by the blunt questions and tried to formulate a reply. The questions did hit a chord with me but I had to be somewhat circumspect in my responses because Nancy and Helen were leaving on a holiday together this coming Monday and I am sure I would be discussed whilst they were away and, knowing Helen, she can be less than discreet.
“I have noticed changes in the last few months,” I replied. “I have fantasized about certain things, but I know that they might upset Nancy, so I have kept my thoughts to myself. It is true that I would like to feel alive sexually again but I don’t know what to do about that. As far as Nancy’s lovers are concerned, I know I can’t compete with them but I do resent it when they call me a panty-boy, pussy, bitch or a sissy and Nancy just laughs with them.”
“I have a theory about that,” Helen replied after some thought. “I think, deep down, the humiliation you feel for being called a sissy or a pansy actually sexually stimulates you. I know you didn’t willingly go on estrogen treatment but you have adapted to it better than any other transgendered patient I have and now I know that you would be very upset and confused if you ceased the treatment. The way you behave around Nancy and me, and the way you cater to her every need speaks of a need to be extremely submissive. Submissive people get off on humiliation. I want to do an experiment to demonstrate that, so take off your gown and walk up to me.”
My face reddened as I did as I was told and took off the gown and approached Helen, who remained seated at the desk and swiveled her chair to face me. I saw her examine my body from my painted toenails to my budding breasts and enlarged nipples. I saw a smile spread across her face as she looked at my penis and testicles. She emitted a little laugh when she lightly gripped my cock between her index finger and her thumb. It was barely big enough for her to hold but it was the first time anyone else had touched it for years and the feeling was electrifying and it didn’t even bother me when she giggled as she held it.
“You have been off of Depo-Provera for over three months but you have been on large doses of estrogen for three years, so it is very unlikely, but still theoretically possible for this little thing to get hard,” Helen said as she continued to hold on to my miniature prick. “So I am just going to continue holding it while I tell you some truths about you that you have to accept.”
I didn’t reply because I was literally too embarrassed to think of anything to say so I just nodded my head. I was mesmerized by the beauty of her smooth manicured hand as it held what remained of my manhood and playfully pulled on it slightly.
“I want you to understand something Briana,” Helen said, looking up into my eyes whilst still holding my little prick between her fingers. “Do you know why Nancy’s boyfriends call you a sissy, or a faggot, or a panty boy? It’s because you are one. You are a little feminized sissy, a submissive pansy, an effeminate wimp whose sole role in life is to make sure your wife is taken care of while she cheats openly on you with men who are superior to you in every way. She fucks real men and you have never been one of those. You are the laughing stock of the neighborhood. You are a cuckold and have been since the day Nancy married you. You were never going to be man enough to satisfy her so we both turned you into the little pussy you are today. First, we chemically castrated you and then shot you so full of female hormones you will never be able to go back and be the wimp you were. And you let us do it with your eyes wide open. You didn’t even want to be a little crossdressing sissy but we made you one. I don’t know of any real man that would let two women do that to him. If I wanted to cut off your balls today you would willingly let me and then fry them up for me for breakfast.”
Helen’s words tore right through me making me blush even more and bringing me close to tears but, despite my utter humiliation, my tiny prick did something it hadn’t done for over three years. It actually twitched in Helen’s fingers. It wasn’t like it was hard by any means but it did show some life and, much to my embarrassment, it actually leaked a tiny bit of semen which Helen scooped up with one finger and brought to my mouth, smearing the sticky juice on my lips.
“Now lick the cum off your lips and get used to the taste,” Helen added. “If you are lucky you will be getting quite a few loads up your behind and in your mouth in the coming week from men who will treat you like the sissy bitch you are.”
I reluctantly ran my tongue over my lips and tasted my own salty cum. With a knowing smile on her face, Helen ordered me to turn around and bend over so she could give me the injection in my right butt cheek. After I put my robe back on and sat down in the seat in shame she made a few notes in my file and looked up to me with a smile.
“I am sorry I was rude to you but I just wanted to demonstrate something to you and make you admit some truths about yourself,” Helen said with a slight smile. “You are a work in progress and you are turning into a beautiful sissy girl. The dose I gave you today and the pills the receptionist will give you when you leave will help speed up the progress but it is time for you to now make some major changes in your life. There are some things I want you to do whilst I am on holiday with your wife. You know that her lovers will need you to take care of them and one lucky man will pop your cherry while we are gone. You better get prepared for that and buy yourself a butt plug to stretch yourself out so your first time isn’t so painful. I don’t want you to be ashamed of your little dicklette any more. Nancy’s lovers may want to see it and they may laugh at it, but you might get lucky and have one of them play with it for a bit. Tie a pink bow around it every morning so it looks more feminine. Keep is smoothly shaved like it is. Your little dick and tiny balls are almost too small to shave safely so you might consider laser treatment. Finally, I want you to change your wardrobe. Go out and get some skirts and nice tops and heels. You are very attractive and you are trying to hide it for some reason. I don’t want to see you again in those leggings and tops. Buy some bras and get some silicon fillers for them so you have a nice feminine figure until your tits grow out more. Nobody mistakes you for a man anymore. You look younger than your age and you’ve got a nice sexy look so get some lipstick, mascara and eyeliner and work on getting a sexier look.”
Helen’s compliments buoyed me and what she said about becoming aroused when I was humiliated had been proven beyond a doubt. I was also extremely happy to be off the Depo-Provera and to have the chemical castration reversed. I had read extensively about estrogen treatment and I knew that, over the long-term, there was very little chance of becoming sexually functional but I could hold out some hope.
“I guess it is time for me to get a boob job,” I told Helen. “I don’t want to have big breasts but I would like to have them about the same size as yours or Nancy’s. I don’t know what to do about my penis and testicles either. I am sort of ashamed of them.”
“I can put you on a fast track for a boob job and I know just the right surgeon for that,” replied Helen. “But we are, under no circumstances, doing anything to your little prick or your balls. You have a very cute little prick. Men who see sissy girls like you want to see the tiniest prick possible, it’s an ego thing. I have studied the psychology of men who occasionally see t-girls and they love the sense of superiority they have over them and the contrast between their manly cocks and the submissive sissy’s little thing, and yours is the smallest I have ever seen. Don’t for a second think any of these men will develop any emotional feelings for you, but they will enjoy you as the little fuck toy that you have become. It’s not what you want either. You will revel in the humiliation of being taken by a real man. I can’t wait until Nancy and I come back, and you serve us dinner and tell us all about your wild week.”
“Now I want you to go out to reception, pick up the hormone pills and go right down to the high street and get a new wardrobe,” continued Helen. “Surprise Nancy when you come home with a whole new look. No more of those elastic panties either. Buy some nice lingerie and some sexy knickers. You are too tiny to fall out of them now, so you don’t have to worry about that anymore. And I want lots of eyeshadow and mascara. Your skin is soft and feminine now, so show yourself off. Be a little slutty.”
“Another thing,” Helen added as I picked my knickers and put them on. “There are plenty of trannies out there and Nancy and I don’t want you hanging out with them. You are totally convincing and completely passable as a woman until, of course, some man pulls your panties down and sees your feminine micro cock. You have nothing to learn from other trannies. I work with them all the time and they are all bitches. You are a sissy, not a trannie, and don’t you forget it.”
I continued dressing and kissed Helen goodbye. I picked up my hormone pills on the way out of the clinic and immediately caught a taxi to the high street. I spent close to £1000 on new skirts, blouses, lingerie and, of course, the silicon fillers for my new bras. I even stopped on the way home to get makeup and to have a manicure. I had the girls paint my nails to match the pink lipstick I had just bought. When I got home I unpacked the bags in the guest bedroom where my closet was. Nancy had locked the door to our bedroom because she had a date with Rob, and they were making love. I dressed in a new skirt, donned a pair of natural colored stockings, slipped my new patent leather heels on and put on a burgundy colored silk blouse and went out to have a glass of wine before I got my ears pierced. My new bra with the silicon fillers gave me a very feminine shape.
It’s funny how men respond to a woman or, in my case a sissy, in heels and a skirt. Needless to say, I didn’t have to reach into my handbag to pay for a glass of wine. Two men even asked for my number in the wine bar but when one of them casually put his hand on my thigh I got up and left. After having my ears pierced I now had a sophisticated look and when I caught my reflection in a shop window I almost stopped dead in my tracks not quite believing the image looking back at me was really me. My black leather skirt was two inches above the knees and my high heels gave my legs a whole new look. I suddenly realized that if I was still a man I certainly would fuck me.
Except for that one-minute interlude with Alex and Nancy I had never been in bed or had sex with a man before. I really wasn’t that experienced with women either. Nancy was only the third woman I slept with and obviously, she was going to be the last one. I needed to armor myself with some knowledge about how to please a man in bed so I popped into the neighborhood Waterstone’s and immediately went to the relationship section and picked up two books about how to have great sex. When I got home I poured myself a glass of wine, went to the living room and sat in one of the chairs and opened one of the books. I immediately turned to the chapter on anal sex and was engrossed in it when Nancy and Rob came downstairs after spending the good part of the afternoon fucking.
They both reeked of sex. Nancy was just wearing one of my old, pre-hormone, shirts and a pair of low heels and Rob had his trousers in his hand and his shirt was open. He did have the decency to put on a pair of boxer shorts. When they flopped on the sofa they both turned and looked at me with a start.
“You look fabulous Briana,” Nancy exclaimed. “I love your new look. How are you getting around in the heels?”
“I’m doing fine in heels and I love the way they make my legs look,” I said as I rose to get Rob and Nancy their ‘after sex’ glass of wine. As I walked towards the kitchen I could literally feel Rob’s eyes on my ass and I gave a little swing to my walk to tease him a bit. When I reappeared in the room bearing two glasses of white wine, I could see Nancy’s hand underneath Rob’s boxer shorts playing with his now erect cock.
“Briana, Rob wants you to do a special favor for him,” Nancy said with a giggle when I put the wine glasses on the coffee table in front of them. “He has to go back to his home now and he is worried that the smell of my pussy juices on his prick will make his wife suspicious, so he was wondering if you would clean it off for him.”
“How would he like me to do that?” I asked innocently. “I can get a wet washcloth from the kitchen.”
“Oh, he doesn’t want his big cock to get cold,” Nancy replied as she pulled down his boxer shorts and released his throbbing penis. “Rob thinks it’s best if you clean his hard shaft with your tongue and take your time while you do it and make sure it doesn’t smell like my pussy anymore. His wife is too prudish to suck his cock but, who knows, she might change her mind tonight and what if she went down on him and smelled my pussy juices?”
Nancy giggled when she saw me look hesitantly at Rob’s rather massive cock, which she was stroking with her manicured hand. She had the confident look of a woman who is very familiar with the male organ of pleasure and knows how to make it spout its molten cream.
“Get over here and drop to your knees and worship a real man’s cock,” ordered Nancy. “Show Rob what a dirty little sissy slut you are. If you don’t have his prick in your hands within ten seconds I am going to have Rob spank your pansy-ass until it is bright red and you won’t be able to sit down for a week.”
I had no choice so, even though I was blushing and burning with humiliation, I daintily dropped to my knees in front of Rob’s splayed legs and took his cock in my hand and slowly began to lick it from the base to the head, swirling my tongue around the helmet and, for the first time, tasting a tiny seed of another man’s salty cum, mixed with my wife’s dried pussy juices. The smell was overwhelming at first: musty, sweaty and masculine. I could hear Rob’s moans as I ministered to his cock and the sounds of Nancy whispering to him. I wasn’t sure if I was meant to bring Rob off in my mouth or if that would infuriate Nancy, who gets jealous at a drop of a hat. My confusion was ended only about 30 seconds after I began to give Rob pleasure.
“That’s enough cock sucking for now, Briana,” said Nancy. “Stand up and go and sit back down in the chair. Rob has to go home to his wife now but I am sure he will be back next week to see you.”
Without saying a word, Rob got up from the sofa, put on his trousers, shoes and socks and gave Nancy a goodbye kiss. Before he went out the door he paused, looked my way for a second and gave me a wink.
