Sissy Briana Pleases Derek

“I tried to take him as deeply as I could in my throat and used my hand to stroke up and down on his thick tool. His moans increased in intensity as I kissed and sucked his large cock and lowered my head further to briefly suck his swollen balls.”

I must have had a tremendous hormonal rush because I had blacked out for a few minutes and came to my senses only when Helen repeatedly called my name. I opened my eyes and tried to remember why I was on the floor in front of the couch. I had soaked my blouse through with perspiration and my forehead and hair were wet with sweat. My body did still feel about ten degrees above normal, but it was a pleasant, sensual warmth, like a furnace of hormones was cooking just beneath my chest and pumping their feminine endorphins through my body. The aftermaths of the hormonal surges still continued to rock my body but now it was under control and I began to recall the events of the morning.

“I can’t believe you asked for another estrogen shot,” said Helen, as she stood over with a bath towel in her hand. “I could give you another shot if you really liked but I wouldn’t allow you to get out of bed for two days.”

“I asked for another shot?” I replied. “What else did I say and how long was I out of it?”

Helen was both my doctor and friend and has started me on the estrogen treatment four years prior which had changed both my body and the state of my mind. I went from an attractive young man of 21 to a cute facsimile of a woman at 25. It had also soothed out my marriage because I no longer felt in competition with my wife’s lovers. Now I was at a precipice and Helen was going to lead me on the next step of my journey. The dosage for the weekly injections she has been giving me along with the pills she prescribed were increased substantially as of Friday, when I visited her office. The day after, I was now a mess on her floor, but a very happy mess.

“You have been out of it for about ten minutes and you kept talking about your mother and the dirty things you did with her,” Helen said with a laugh. “I have to meet this woman some day. Anybody that can turn their son into a willing toilet slave seems like my kind of woman.”

“Oh God, I must have forgotten that or suppressed it; I can’t believe I mentioned that to you,” I said as the remembered shame of it all made me blush. “Every morning I had a big glass of her pee. She said it was full of her hormones after the night and it would be good for me to have her inside me all day.”

“She sounds like she was ahead of her time,” Helen said. “How old is she now and where does she live?”

“She is in her late forties and lives in Sydney with her new husband,” I replied. “She looks much younger than she is and is still a knock out.”

“How did sleeping with your mommy affect other relationships you have had in your life?” Helen asked as she took a seat on the sofa while I was still recovering on the floor. “That’s a pretty unusual start for any man’s sex life but, strangely, I wouldn’t call it abusive or even use the term incest to describe it. It was consensual and carried on for over six years and fulfilled needs for both of you but it seems to have started you on a life grounded in submission to whatever woman you could choose to be in a relationship with. I can see now why it was so easy to convince you to forego your manhood and become a willing sissy and how you’ve now embraced it with such enthusiasm.”

I pushed my shoulder-length blonde hair back from my head and thought about it for a minute but I was too drained and struck dumb by the hot flashes I had all morning to really have any sort of serious psychological discussion. I felt pleasantly disorientated and bit bewildered by my current state. I actually thought about asking for another injection. The idea of experiencing even more intense moments than I just had was extremely appealing, even if it meant staying in bed for another two days.

“I’m sorry, Helen, I can’t think straight now, and I feel like a mess,” I said. “I felt so fresh when I came out of the house this morning and now my clothes are all wrinkled and I’m sure my mascara is running. The only thing I can think is who is going to give me my treatment while you and Nancy are gone.”

“I’ve already taken care of that,” replied Helen. “Now take this towel and go upstairs and shower. There is a white sundress laid out on my bed for you. Just throw the clothes you are wearing in the hamper. I’ll make sure they are cleaned and returned to you.”

I showered, washed my hair and dried it and reapplied makeup, this time putting on, not only mascara but eyeliner and lipstick as well. I went into Helen’s bedroom and slipped the sleeveless sundress over my head and looked at myself in the mirror. I was no worse for wear and I had a lot of healthy colour on my face which had probably been brought on by the numerous hot flashes I had already had in the morning. I knew that as the day wore on whatever rushes I would feel would be weaker and weaker until it all started over again on Sunday morning.

I bounded down the stairs to find Helen dressed for the day. She looked me up and down and seemed to approve of how the sundress fit me.

“Let’s get you some strappy sandals and something to eat,” she suggested, grabbing her bag and leading me out the door.

As we walked down the street we got the attention of every straight man and envious looks from a number of women. I realised, with the sun behind me, that everyone could see the outline of my figure through the flimsy sundress and, for the first time in a while, I was glad I had a tiny penis and balls and could neatly tuck them into my knickers, giving me a smooth feminine appeal. We stopped into a shoe shop and I immediately found the right pair of strappy sandals with a two-inch heel. After I paid for them I slipped them on and put my trainers in the bag. We crossed the street to a small crowded bistro where we, fortunately, found one empty table in the sun.

After we placed our orders with the waiter, Helen turned to me with a concerned look.

“Chrissie, I want you to know you always will have a home with me,” she told me. “I worry about you. You are such an innocent and Nancy is too wild. Who knows what she might involve you with and whether she will go out one night and not come back? She is capable of that, you know, and where would that leave you?”

I felt a surge of emotion run through me. Helen had pinpointed my biggest anxiety in life. Nancy was on a rollercoaster and lived life without a care in the world. She was also attractive and drew men to her and, one day, someone was going to come along and convince her that being married to an impotent sissy wasn’t her future.

“Thank you,” I replied. “I know one day she will leave and I wake up every morning surprised to see her in the same bed as me. I know you get more pleasure out of me than she does because I am really your creation.”

“I thought that up until this morning until you told me about your mother,” Helen added with a laugh. “It seems she was working on you years before I got my turn. You really have to fly her up here so I can meet her. You were her sissy first. Now we could compare notes.”

We were both wearing large sunglasses which gave us the ability to people-watch without being obvious. I heard Helen take a short intake of breath as she reached over and grabbed my hand under the table and gave it a tight squeeze.

“Oh God,” she whispered. “That’s Derek across the street with the dark suit on. If he sees us and comes over I don’t want you to say a thing. Just let me do all the talking. When he talks to you I’ll answer.”

I looked over across the street and I saw a sharply dressed man in a blue suit and the only adjective I could think of to immediately describe him was hard. He had a vague air of respectability about him that anyone could tell was just a thin veneer tightly held over an underlying coiled spring of steel. He wasn’t the man you would want to offend or get caught looking too closely at his wife. He emanated a certain threat which I am sure he cultivated over the years in whatever bit of the underworld he occupied. He was also just the sort of man Helen preyed upon: dangerous, unpredictable and seemingly untameable.

As luck would have it, he spotted Helen and confidently walked across the street, grabbed a chair and joined us at the table. Helen kept hold of my hand under the table gripping me tightly as if to remind me of her words or warning. Things didn’t bode well for that as I saw his eyes firmly lock on me and he studied me from my feet to my hair with a knowing superior smirk on his face. I was embarrassed by his attention and blushed and looked downward. I was used to men looking at me but not with the sort of intense scrutiny of Derek. I felt I was being assessed as to my value in a clinical way, not so much as a sex object, but as a possession that could be owned and traded.

The waiter served Helen and I our poached eggs on toast but the last thing I wanted to do was pick up a fork and eat. The two of them seemed to whisper together but I couldn’t hear what they were saying as the heat of another hormonal surge took over my body coupled with what I assumed was a panic attack, which was another unfortunate consequence of my estrogen treatment. I had the wherewithal to quickly reach in my bag, grab my pill case and quickly dry swallow two valium tablets, but the warmth and tranquillity I would feel when they kicked in was ten minutes away. My brow and chest grew red from the heat of my body. I could see Helen and Derek whispering to each other but their voices were too faint to hear. He kept looking at me and shaking his head with a look of disbelief whilst she nodded her head. She had a concerned look on her face whereas he had a cool look of detachment. The bistro did three spins as I surrendered to what was the most intense hormonal rush I had ever experienced while Derek and Helen seemed to move in the distance and speak above me, although I could vaguely sense I was the sole topic of conversation. I felt like I was in a state of temporary suspended animation while erotic thoughts tumbled through my brain and images of my mother’s lovely thighs filled me with a longing for my younger days. Nothing felt more like home than the feeling I used to have when I tasted mommy, licked her pussy and heard her moans of pleasure. It was the secret place I went to in my mind when I felt most insecure. I missed her more than I wanted to admit.

Slowly I began to come to and was shocked to find myself holding a fork above my plate while Derek and Helen looked at me with concern. I must have been out of it for ten minutes because I began to feel the warmth of the valium tablets spread through me and my emotions began to get under control.

“I’m sorry,” I stammered, looking up at Derek for the first time and realising that Helen still had a firm grip on my hand under the table. “I was out of it for a little while and didn’t hear anything you two were saying.”

“Who is Mary?” Helen asked in a whisper. “You kept talking about how you missed Mary. Is Mary your mother’s name?”

A blush spread across my face as I nodded in the affirmative. I could see that information took Derek aback as he arched his eyebrows with an astonished look. Helen only gave me a sympathetic smile.

“I said before we have to get her up here as soon as possible,” Helen said, this time in a clear voice, not a discreet whisper. “Let’s call her up today and make arrangements. She would love to see the new you, or at least that’s what you led me to believe.”

“I would love to see her again too,” I replied and gave Helen a smile. “She would love you but I’m not sure how she would take to Nancy. They haven’t met yet.”

“Is Nancy that South African slut that’s your friend?” Derek asked, not realising that the woman he was referring to was my wife of five years. “She has a reputation that stretches around the world. Word has it that she could suck the chrome off a car bumper.”

“Be quiet,” Helen said sharply to Derek. “Nancy is married to Chrissie and she’s a good friend of mine. She lives by her own rules.”

That information appeared to be too much for Derek to process. He studied me again and cupped his hand and whispered something into Helen’s ear. When she whispered back to him he shook his head in disbelief. The whispering continued for a few minutes then Helen and Derek both rose from the table.

“Will you be alright on your own for a couple of minutes?” Helen asked. “Derek and I want to have a private discussion and it would be impolite to do that in front of you. We’ll just be a few feet away, so don’t worry. I can rush over if you start to feel funny again.”

I was glad they were gone because it gave me time to recover. I took out my compact and looked at myself in the mirror. My makeup looked fine but I quickly dabbed on some lipstick and ran my fingers through my hair and smoothed my dress. My appetite was gone but I drank both glasses of water that were on the table.

They soon returned to the table smiling, seeming to have agreed on a subject in my absence. Surprisingly, Derek took out his phone, told me to smile and took a couple of pictures and seemed to send them to someone. He quickly got a reply and stood up and told us to follow him. Without seeming to have a choice in the matter, I opened my handbag, laid £20 on the table and followed the pair to destinations unknown.

“Where are we going?” I asked Helen when I caught up with her. “What were you two talking about?”

“Just follow my lead and do what I tell you to do,” she replied with a knowing smile. “You need someone to protect you in life and I will be there to do that, but you need someone else like Derek who nobody in their right mind would fuck with. Just be quiet and do what you are told and trust me when I tell you I know what I am doing.”

After walking a few blocks we arrived at an apartment block. The doorman let us in and we walked to the lifts. Derek pushed the button for the top floor. As we travelled up I kept my head down and tried to repress another minor hormonal rush. The valium was kicking in fully now and doing a good job of suppressing my anxiety.

The lift was mirrored and I had time to briefly glance at myself and I could see I still looked fresh and had nice colour in my face. I also quickly realised I was the shortest person in the lift. Helen, who wasn’t wearing heels, was a few inches taller than me and Derek was at least a foot above her. The realisation made me feel slight and petite, which was a familiar feeling. I used to love the way my mother and I looked in the mirror together. We are both the same height and have the same slim look, although I always envied her breasts and pert bum. I don’t know why my mother was occupying my thoughts so much but the image of her filled my mind every time the hormones rushed through my body. Even though we were thousands of miles apart I felt closer to her than ever, perhaps because I was becoming more like her physically and mentally.

The apartment Derek led us into was just what I expected from the villain. It was a spacious penthouse with wrap-around balconies. The floor to ceiling windows were open and the light curtains were billowing in the breeze. Without asking, Derek went into the kitchen, opened the refrigerator and took out a bottle of white wine, which he poured into three glasses. As he handed me mine he directed us to the living room and told Helen to join him on the couch. I was left standing in the middle of the room.

“Take off all your clothes and let Derek inspect you,” Nancy told me as she crossed her long legs and nestled up closely to Derek. “Don’t worry; nothing bad is going to happen to you. Derek just wants to see you fully.”

I blushed and lowered my head and kicked off my shoes. I felt completely displaced as I looked around the room, which was the size of a normal person’s apartment. I lifted the sundress off my head, undid my bra carefully so as not to let the silicon fillers fall to the floor and wriggled out of my panties. I trusted Helen enough to go through the humiliation of letting a straight man inspect my sissy body and the two valium tablets continued to quell my anxiety. I could see Derek focus first on my shrunken penis and testicles and I watched as his gaze moved to my puffy breasts and enlarged nipples. He nodded with approval as he took his phone out and snapped more pictures of me and then appeared to send them off to a contact of his. An unmistakable bulge began to grow in his crotch as he continued to gaze at me. I was mesmerised as Helen undid his belt and zipper and pulled out his manhood and held it her hands. I stood still and let him admire me for what seemed like minutes. His hard circumcised cock began to grow to its full length as Helen touched the head of it lightly between the same two fingers that had once touched my tiny prick. I could see some of his semen leaking out.

“Come over here and make Derek happy,” Helen commanded with a low erotic voice more like a purr than a whisper. “Put your sissy lips and tongue on a real man’s cock and concentrate on giving him pleasure.”

I did what I was told and lowered myself to my knees between his legs and lightly held his throbbing prick in my hand and lowered my mouth over his helmet, swirling my tongue on it and catching the taste of his manly cum. I tried to take him as deeply as I could in my throat and used my hand to stroke up and down on his thick tool. His moans increased in intensity as I kissed and sucked his large cock and lowered my head further to briefly suck his swollen balls. I was in a dreamlike trance as another small wave of hormones swept through me and I struggled to concentrate on providing Derek with pleasure and push the image of my mother’s smooth thighs away. Derek gasped loudly and held my head down on his cock as I could feel his testicles contract as he began to erupt. I sucked the hot spurts of his cum eagerly, careful not to spill a drop and let his jism linger in my mouth until I swallowed it all. I continued to suck him briefly although I could tell he was becoming increasingly sensitive so I carefully licked his cockhead to catch the final spurts of cum that were leaking out of his dick. When I was finally done, I continued to hold his prick in my hands and looked up at Helen with a curious gaze. It was the first time that a man had allowed me to suck his cock until completion and I didn’t know if she realised that the first part of my virginity was taken that morning by Derek, nor did I think she grasped how much joy that gave me.

“That was beautiful,” said Helen with a knowing smile as I gently let go of Derek’s softening cock. “Now go and freshen up while Derek and I talk privately. Take your time, we have a few issues to straighten out.”