Caroline Meets Katie

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Erotic lesbian and T-girl transformation.
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Veritty
Veritty
2 Followers

At last it was 6pm and I had just left the office and on my way home. The last Friday of the month was always a very special day in my calendar. My mind was racing, as I knew that Caroline would be waiting for me, waiting to tease me, punish me, and pleasure me whilst transforming me into her T girl. God, how much I looked forward to the last Friday of the month.

I arrived home at just gone 7pm and eagerly entered the house. Caroline was waiting for me in the living room and smiled wryly at me as I entered the room. As always she looked immaculate, her shoulder length strawberry blonde hair was the envy of any woman, her make up was absolutely perfect, and of course Caroline was beautifully dressed. She was a sophisticated and elegant woman in her early 40's and in keeping with her inimitable style she wore a very pretty ivory coloured silk jersey wrap dress with the most subtle floral print in shades of soft grey and lilac. Her legs were long and slender and encased in the palest of grey nylon. The soft sheen of her hosiery really turned me on. As I gazed at her delicate feet, I could feel my cock begin to twitch in my pants. Her shoes were suede and the colour a soft lilac that coordinated beautifully with the print of her dress and the two-inch heel was just the right height to show of her trim ankles.

She knew I was entranced and walked across the room and stood next to me. The aroma of her perfume was intoxicating and I could clearly make out the delicately embroidered cup of the bra that she was wearing. Caroline had magnificent breasts, her narrow back and slender physique accentuated the 32c that she was so proud of. Her nipples were thick and reddish brown in colour and were surrounded by large puffy areolas. Caroline was as usual a sensation, and I was her plaything.

Without notice, the tone of her voice changed and I was ordered to go upstairs to the bedroom and strip naked and wait for her to arrive. I nodded; left the living room, climbed the stairs, and entered her bedroom. The room was centred on an enormous bed that was covered in soft scatter cushions in an array of pastel colours. How I wished that this could be my bedroom. I undressed and waited for Caroline to arrive. It was some fifteen minutes before Caroline entered the bedroom.

Come here she said, where I can get a better look at you. Caroline walked around me and inspected my body. She slapped my buttocks and murmured something under her breath that I couldn't make out. She told me to open my legs and as I did so, she wrapped her hand around my cock and scrotum and tugged them back thru my legs towards my arse. It's a good job that you are small Katie, having a small penis makes things much easier for me. Caroline promised that she would teach me how to dress like a woman, walk like a woman have the sensitivity of a woman and most importantly how to be fucked like a woman. My cock started to twitch and Caroline noticed immediately. Getting excited at the thought are you, you are a truly pathetic man but as my T girl, you will be so perfect. You will be a good sub to Caroline won't you my darling? Yes, Maam I answered subserviently. Don't worry darling in a very short while you will be Katie, but before that moment arrives we have some preparation to do, now follow me into my dressing room.

I followed Caroline out of the bedroom along the landing passing several doors before we arrived at her dressing room, Caroline opened the door and I followed her in. I was in heaven, the room was decorated in a very feminine style, the furniture was exquisite, candles burned everywhere I looked, and the scent they gave off was divine.

Caroline had been shopping, something that she could do very well. She loved spending my money and lots of it on gorgeous lingerie, hosiery and outfits for her and for me. As my eyes scanned the room I noticed that there were several adorable bra and panty sets laid out for inspection together with at least a dozen pair of stockings, I also noticed from the elegant packaging that they mostly had deep lace or satin tops and doubtless very expensive.

Then my eye found a selection of gorgeous open bottomed girdle's waist cinchers as well as several other foundation garments, all of which coordinated beautifully with the bra and panty sets Caroline had bought. My cock was as stiff as a pole and Caroline looked at me in disgust. That is repulsive said Caroline pointing to my erect penis we will have to deal with that before we can do anything we don't want you dribbling pre-cum all over these adorable panties and stockings do we Katie. No, I answered hanging my head in shame.

Caroline left the room and did not return for what seemed and age. When she did, my penis had become limp. However, at the sight of her it became swollen and hard in a moment. Caroline had indeed returned she was carrying a large bowl and several small flannels. More importantly, she had taken off her dress and was standing inspecting me in her lingerie sheer stockings and lilac suede shoes. She wore the most beautiful bra and panty set I had ever seen the fine embroidery on the bra cups masked her nipples perfectly, continued on front panel of her sheer panties, and extended to grace her satin, and lace-matching waspie, which to my delight was firmly boned. The ensemble was in the prettiest pale honey colour and the embroidery of roses and butterflies contrasted in pale pinks and light blue. The mental picture that I had of her hosiery when I first saw Caroline in the living room was rewarded. It was now apparent that she was wearing the most heavenly pale grey RHT sheer stockings that had a delightful contrasting deep satin top.

The six metal clasps of her suspenders were pulling delicately on her stocking tops and the name La Perla was woven into the nylon between the deep black satin welt, and the darker charcoal band of nylon before the sheer pale grey stocking began to cover her leg. She had me on fire. I swear I could have cum almost without being touched.

Caroline placed the bowl on the floor, held my swollen penis in her hand and made me kneel in front of her. Katie let this be a lesson to you. This is what happens to T a girl who gets erect in front of Caroline without my express permission, this must never happen again, do you understand me young lady. I nodded in full agreement with her, whereupon she took hold of my balls with her left hand and squeezed so hard I shrieked with pain. Please stop Caroline I beg you it hurts so much. It is supposed too Katie she said as she plunged my swollen penis into the ice-cold water. My erection disappeared immediately. Good Caroline said sternly that is quite enough of that nonsense. She took the dry flannel in her right hand and roughly dried my genitals. Finally, she squeezed my penis and wiped the last drop of pre-cum from the head of my cock.

Katie get up Caroline ordered and sit in the armchair, place one leg over each arm, get nice and comfortable because Caroline is going to shave you and expose your pretty clit stick. My balls ached and I had to cup them in my hand as I sat in the chair and positioned my legs astride the arms. Caroline wasted no time first; she slipped a cushion under my arse, which positioned my groin perfectly. I was so excited I could only stare at Caroline as she sat down on a stool between my open legs. She smiled at me as she proceeded to clip the hair around my penis and balls with the sharpest pair of scissors imaginable. Don't move an inch she said as she held my limp penis to one side and continued to snip away at the hair on my scrotum. Then she took a hot flannel and wiped all the excess hair from my groin and ball sack before massaging my genitals and surrounding area with a proprietary hair removal cream. I had to sit with my legs astride the arms of the chair and wait for fifteen minutes whilst the cream had time to take effect. We spent the time talking about how wonderful I would look and feel being hairless. The time passed and Caroline washed me carefully and hey presto she was right I was beautiful. Smooth and soft with not a pubic hair to be seen. Wow, I felt so sexy. Now on all fours Katie like a good girl and spread your legs so your buttocks are stretched, as we have to repeat the process on your love hole. Caroline are you sure I whimpered, do not question me Katie Caroline replied. You are mine to do with as I please. Do as you are told right now. Do you think I am going to finger, lick or fuck your love hole the way it looks now, because if you do you are sadly mistaken?

Dutifully I did as ordered and Caroline creamed my anus and inside my buttocks. The sensation of her fingers rubbing the cream in and around my arse was made more thrilling by the gentle warmth of the cream doing its job. I felt so incredibly turned on that all I could think of was a stiff cock fucking my arse. After another fifteen minutes or so, Caroline wiped away all the cream and with it, I was smooth and hairless. I stood up and Caroline led me back to the armchair to sit and watch as she prepared my wardrobe.

Tell me Katie said Caroline, it would appear from the way you have been staring at me that you like my lingerie, my stockings in fact my total look. Am I correct in assuming that this is the case Katie? Yes Caroline you are 100% correct, you are so sexy and beautiful I do not know what to say other than I wish I were you. My darling girl do as I say and you will be just like me, only better. I promise you darling T girls are very special. I had a feeling that you would like my outfit so as well as buying this for myself today I bought the same for you my darling. Exactly the same, does that excite you Katie.

My body shuddered as Caroline held in front of me the exact bra and panty set that she was wearing and of course the beautiful matching waspie and a packet containing the exquisite La Perla sheer pale grey stockings. I was so excited and desperately wanted to touch and feel the beautiful bra around me. Not so quick young lady let me show you the matching wrap dress and shoes. I simply could not believe it everything was just so right. I began to cry with joy and excitement, there, there Katie, Caroline said as she kneeled down next to me, and I put my arms around her and sobbed. As she comforted me, Caroline held my head next to her warm bosom and with her free hand gently held my cock. Ever so slowly, she began to milk me. Sh, sh Katie do not cry we will have you looking just beautiful in no time just let Caroline milk you, don't cry. After a couple of minutes Caroline's right hand moved away from my cock and settled on her breast. Would Katie like to suck on Caroline's tits whilst I continue to milk you baby. Oh God yes, please Caroline, please let me that would be so wonderful. Caroline's delicate fingers unhooked her front closing bra and her magnificent boobs gently spilled out from her balconette underwired bra. There you are Katie darling suck the milk from Caroline's heavy boobs whilst I wank all the cum out of your little cock. I needed no encouragement, immediately I took Caroline's left nipple, areola and good amount of breast flesh into my hot little mouth, and began to suckle. Good girl Katie that feels so good, Caroline's boobs are so sensitive, suck harder Katie chew my nipple there's a good girl. I did exactly as I was ordered and sucked and chewed on Caroline's full breast. After several minutes had passed, I felt my self about to cum. Caroline sensed the same and quickly removed her left boob from my mouth lowered her head, swallowed my cock in her warm mouth, and after four hard sucks, I had a beautiful orgasm and shot my load deep into her throat.

After Caroline had swallowed my load she stood up and told me how wonderful that was for her but she had to punish me as my cum had dribbled on to her nylons and stained them. Now they were ruined. She pulled my cock so hard I screamed but she took no notice. You nasty slut Katie, Caroline screamed. Look at the cum stains on my nylons they are ruined you stupid bitch, do you have any idea how much La Perla stockings cost? I am not sure but I am so sorry Caroline, I did not mean to stain your nylons. You are are going to pay for this Katie, over my knee NOW. Caroline began spanking me with a riding crop. It hurt so much, but the more I whimpered the harder the leather crop met my buttocks. Eventually Caroline stopped but before I was allowed to stand up she gently probed by anus with her finger. That is just a taste of what is in store for you Katie. Now stand up and wait in the corner. Do not look or touch any of the pretty things in this room. I have some telephone calls to make I will be back in half an hour. Caroline walked me to the corner and made me hold my head in shame with my hands clasped to hide my now smooth clit stick.

Caroline duly returned as promised half an hour later, I dare not look up and held my head in shame. Caroline spoke kindly to me, don't worry Katie it was only a silly pair of stockings, we have plenty more. Now I want you to come and sit next to me on the bed and help Caroline change into a fresh pair of stockings, would you like to do that for me darling? I simply nodded as she held my hand and sat me down at her side on the vast bed.

Katie you choose for Caroline which pair should I put on. I was bewildered but happy as Caroline passed me six different pairs. I took much notice of the packets being passed to me for inspection. Finally, I made my selection. What about this pair Caroline? Fabulous was her reply they are just perfect I would have chosen them myself. I felt on top of the moon. Now take them out of the packet and lay them carefully on the bed and I will teach you how a woman rolls stockings over her legs.

The stocking that I had chosen for Caroline was an ultra sheer RHT from Gerbe a 7 denier non-stretch stocking in a colour called gazelle, which was a very pale coffee, and the stocking had a contrasting satin top in black. These are very special stockings darling and extremely expensive. Clearly, you have very good taste Katie. As a reward, Caroline placed her left hand on my balls and squeezed them firmly.

Caroline stood up, unhooked the three suspenders from each leg, and rolled down the pale grey stockings that were now badly stained from my cum. Throw them in the bin Katie and pass me the new pair. Before she passed me the stained nylons, Caroline let them fall gently over her bare bosom, which resulted in her nipples growing stiff. She smiled knowingly at me as I picked up the stockings from the floor and placed them in the bin. Caroline opened the new pack of stockings, discarded the paperboard that held them neatly in the package and proceeded to feed her hand gently down the leg of the stocking until her fingers arrived at the darker reinforced nylon of the toe. She held up her leg and pointed her toes toward the floor bent forward slightly her breasts swinging forward so seductively as she slipped her foot gently into the sheer nylon. At which point she began to delicately roll and pull the stocking firmly but carefully up her leg. Finally, she stood up her boobs bobbing gently too and fro, and attached the three suspenders to the satin top, all the while making sure that they were evenly spaced.

There you have it my darling Katie that is how a woman perfectly puts a stocking on her leg. She repeated the process on her left leg and finally made some small adjustments to the suspenders and smoothed the nylon from her ankle to her thigh on both legs.

Beautiful don't you think Katie. I agreed. Now it's your turn darling but before you slip into this pretty panty for me, I am going to give you a little surprise. Caroline lifted her right leg and placed her foot on the bedroom chair. Take a look Katie what do you see Caroline asked. I see a tampon string hanging between your legs Caroline. Good girl Katie. Caroline produced a Tampax in its applicator and told me to lift my leg. I did as I was told. Caroline lubed the head of the waxed cardboard applicator and positioned it firmly against my anus. Lean on the dressing table darling as this may hurt a little Caroline said as she pushed the tampon deep into my arse. She was right it was a little painful, as the dry wadding of the tampon did not slip easily into place. However, when Caroline had finished it felt sensational. I stood upright, looked in the mirror, and could see the string hanging down between my legs just as I had seen Caroline's a few moments earlier. As my reward, Caroline handed me the lace panty to wear. It was identical to hers and it felt gorgeous as I stepped into each leg and pulled the panty up, positioning the fabric to hold and conceal my penis and balls.

Caroline adjusted the gossamer like material to cover my scrotum perfectly and re- positioned my dick so it was back between my legs. Finally, she separated my buttocks and ensured that the fabric of my thong was tight into my now hairless crack. Caroline the feeling is sensational, but the panty feels ever so tight. Katie of course it does my darling Caroline bought you one size smaller so you can experience a little CBT.

Now time for your bra, it is the same as mine except that it is a full cup rather than a half-cup and it has a back closing rather than front like mine. Other than that, it is identical. When your boobs have developed to a full B cup, I will allow you to wear front closing bras. Anyway, a full cup bra will give your greater confidence especially whilst you are wearing breast forms. I held out my arms as requested and Caroline helped me fasten my bra and then filled the cups with my silicone boobs. They looked and felt wonderful; they even had permanently stiff nipples. My god they are so heavy Caroline, I am sure they are darling after all you are wearing a 38d they should be heavy. By the way, they look fabulous on you.

Well Katie take a look in the mirror at your new bra and panty set. Caroline stood behind me as I admired how femme I felt. As I was doing so I felt a tug on my tampon, it was Caroline pulling on the string between my legs. Don't get to carried away darling we have a long way to go. Caroline selected a coordinating waist cincher for me to wear. You need more shaping than I do darling this firm cincher will be perfect. She wrapped it around my torso and fastened all 14 hook and eye fixings. It is so tight Caroline I said. Katie this is the way it has to be do you understand. You do want to be a woman and enjoy being fucked as a woman don't you? Of course, I do Caroline I am so sorry for being disrespectful. Sit on the bed Katie and let me watch you put on your stockings just as Caroline taught you to do. My heart pounded as Caroline handed me the packet. I opened the pack nervously and laid the she stockings on the bed just as Caroline had done earlier. Good girl Katie now be careful darling we don't want any mistakes do we. I gently gathered thin nylon in my hand and finally had my fingers in the reinforced toe area. I raised my leg pointed my toes and started to roll and carefully pull the stocking on to my leg. It felt so wonderful. I stood up clipped the suspenders into the satin welt and repeated the process on my other leg. Well, well said Caroline ten out of ten. I can see that you are a fast learner.

For that, I am going to share a little secret with you that I have planned for us. Would you like me to tell you what that is.Oh yes please Caroline? I thought you might. I spoke to my secretary on the phone earlier. Her name is Lucy and I asked her to pop over to meet you, she will be here very soon. Don't worry Katie she knows all about you and is dying to see you. So let's hurry and get you into your dress. I stood up and Caroline helped me into the pretty wrap dress and assisted me with my shoes.

There you look stupendous Katie. How do you feel? Fantastic I replied. Now help Caroline put her bra and dress back on and we will wait for Lucy to arrive. I picked up Caroline's bra and walked toward her. She held out her arms and I placed the straps over her shoulders and fastened the clasp. That feels so much better now pass me my dress darling. I passed the dress and Caroline stepped into it and fastened the sash. She looked at me slipped her hand inside my dress and adjusted my left boob. That's better now you look just like the pretty T girl you so want to be.

Veritty
Veritty
2 Followers
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