Dressed So Ch. 04: Tess’s Notes Pt. 01

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Please find a moment to read the story “Dressed So”. The following is a supporting chapter to the three parts previously released. This is a collection of notes Tess prepared over a period of years.



I laugh today thinking of how strongly Michelle had come on to me at the riverside restaurant several months ago. I was with two girlfriends having a pleasant light dinner on an early fall evening. She must have been dining as well, for she came into the rest room, clearly having followed me.

“Can I help you?” I asked noticing her stop at the washbasin, just to stare. But she said nothing, yet she moved two steps closer.

She said nothing in response to my question, “Excuse me, but I don’t know why you’re looking at me like that. I need to pee, excuse me.”

I noted her expression changed to a lewd smile, “I’ll listen, and I’ll wait than, ok?”

She was beautiful with near platinum blonde hair, possibly nearing forty maybe older, tall and dressed in a severe yet sexy black dress. I noted her nice figure, her jewels and her scent, as well as her legs and heels. While I sat relieving myself she had moved closer to the stall door. I could see her heels beneath the door, for she was very near the door and had turned. Standing as she was, I would need to again ask to be excused when I had finished and resettled my garments.

Opening the door very slightly I said, “Excuse me Madame, please move so that I can leave the stall.”

She didn’t respond but with the door slightly open I saw her right hand extended partially within the stall. Looking toward her hand I saw she was extending a shiny object to me. Without a word I reached for her hand and she opened it while pressing the cool object into my palm.

“What’s this Madame? What have you given me” as I lifted the steel object closer to see it in the dim light.

“Don’t drop it young Lady, simply lift your hem and put it where it belongs.”

Now I could see what she had placed in my hand, a heavy steel anal plug, with a ruby stone on the flared end.

“My god, you have confused me with another girl Madame, please move away and allow me to pass.”

She turned to face me and while opening the door she moved inside and took me into her arms and our mouths met.

“You will be back to your friends in a moment but you will be wearing my plug.”

I was shocked by her next move as she closed the door and held me close for another deep kiss. Somehow I allowed this, but I was again surprised when she moved her left hand to my round bottom and ran her finger along my cleft and than lifted the hem of my dress. She was deep in my mouth and her other hand was atop mine as she moved the plug beneath my dress. I was wearing a cream-colored sweater dress, which fell several inches above my knees, and I was a bit unsteady in my black pumps.

I was quite aroused, her body was pressing mine, her breasts at mine. I was somehow willed to accept her seduction. As her kiss continued her left fingers explored my damp panty and she grasped my slightly stiffened clit.

“Now I’m happily surprised young ‘Lady’, but I will help you get my plug into your tight passage.”

Moments later she allowed me to leave but she had done what she’d wanted. Somehow I would notice her next signals, I would follow her home that evening.

Two weeks later, having spent almost all of my time with her, Michelle told me of her husband.

“I figured there was a chance you had a someone, but he’s not where you’re happy, huh?”

She detailed their history and her career success in trading, his missed opportunities. But I was surprised when she told me he had suggested she try to meet a Lady. She didn’t want to share me with him, though he definitely was interested. She hadn’t told him about my clitty, just that I was a lesbian with a ‘special gift’.

“Let’s try and forget about that new information and settle into each other tonight, ok?”

I paused to consider the offer, “Are you telling me you want to fuck me, or just that you want to cuddle?” I smiled and we went to shower.

During the past weeks she had used a cheap strap-on to fuck me three or four times. I had insisted she get an insertable and it had arrived this morning. Before showering I help Michelle with the toy. We practiced pushing it inside her vagina until she was comfortable.

“Now, how should I dress for my special penetration Michelle?”

She stepped into the large warm space, “You shall select out two corsets and two pairs of the full fashioned seamed hose. You can find our heels, they should make you beautiful bum look super sexy Tess.”

I went to the wardrobe and selected two under bust corsets, a soft peach one for her and a deep red one for myself. The hose were easy since she had only two pairs left. I’d ruined several during our earlier sex play. But the creamy ivory would be sexy with her peach and the black for me. I selected her 120mm heels, beige with a strap, and mine were gaziantep escort 130mm black without a platform. I would enjoy trying to move about in them.

As I reentered the bathe I hear, “It’s lonely in here without you Tess.” I stepped into enjoy seeing Michelle’s soapy pussy.

“Can I help you there?” I moved close and kissed her mouth. “Already Mistress, I need your cock now dear.”

“Soon, be patient Tess, or I’ll tease you for an hour first, humm?”

This woman could get my attention and we had fun outside the bedroom as well. Her significant other might destroy our budding relationship, started by such a lewd act in a restroom. I was lead from the shower by my instance Mistress.

“You will be filled properly tonight my Tess, but I want you to dress me first.” I did as Michelle requested and than I gather my own garments.

“Your thong Tess, and then I’ll help you set your corset Tess, 64cm is the target.” I had pulled her tighter earlier this week to 63cm and now it was fair play.

“Of course Mistress, as you desire.” She came behind me and started tugging the top strings then as I snug each I moved lower.

Afterward I reached for my black hose and using the six clips secured them, “those heels are simply marvelous Tess. Please come to me dear, I want to observe your walk, turn and show me your butt, oh wow, you look wonderful.”

We retired to the bedroom and I suckled and played with her breasts and pussy, waiting her signal to insert the toy. I needed a good fuck. At the moment I recalled my old friend and lover David, how he had help me realize why too much cock could be a bad thing.

“I want to enter you from behind first Tess, please move to your tummy across the wedge.” A moment later her cock was at my opening and I turned to beg Mistress, “Please push into me Michelle, I’m ready.”

And so she started to slip inside me, once the helmet passed my muscle the smooth shaft met no resistance. She reached for my breasts and said, “Can I fuck you deeply or should you need a moment to contemplate my cock?”

“Fuck me Mistress Michelle, give me your great cock.”

Tomorrow I might leave her for good, to stay clear of her problematic husband. I needed a woman who wanted my cock but also loved my beauty. Michelle was not this woman, I now knew this, but she was fucking me and fucking my bum deeply.

“Mistress, please push your cock deeper.”


Seeing this woman crossing the room beside Juli caught my attention. I didn’t know her but had heard that we had two new members at Faunesse. Juli was shuffling the tall blonde about, with introductions and more wine. I’d watched them for thirty minutes when an opportunity presented itself. I had found the power of Michelle’s seduction so intriguing I might try with this new beauty. As she moved toward me I looked to her and smiled. As she drew near I rose to speak with her. She smiled back and we enjoyed the flirting. She didn’t even look at the plug I’d given her, simply dropping into her handbag. Maybe I would fail at this aggressive seduction game.

Later Alexa had slyly smiled, “I saw her reach for it as she left the doorway and she looked back into the room. I thought she was looking for you. But you had met Emma and were walking away toward the windows. I had met my new lover that night.


I had come to realize that I wasn’t like the others. I started to let my hair grow, and my nails for that matter. Both were easy to disguise but eventually my Mom saw the changes. We discussed what I wanted to do because she also noted I’d started to wearing a training bra under my shirt nearly every weekday. I would stop at a gas station each morning to adjust my appearance. A light coat of lipstick and mascara were easily applied in the poor light, and the shoes were concealed in my backpack when I’d leave the house. The kids and school were a bit mean but some were ok with me.


I’d hung out with several pretty girls from my neighborhood since I was ten. I enjoyed the time with the three of them and they would occasionally press me to try on their clothes. One afternoon John, the older brother of Jill, came down the stairs and found us. I was wearing Jill’s new dress. He turned back up the stairs. Later he approached me and told me I was quite cute when I dressed with the girls.

“I’ve seen you several other time Tracy,” and he pulled me near and kissed me.

“No John, please, I don’t want to cause you any problems.” It was the first time I had been kissed by a boy. I ran home and cried.


When I reached my fifteenth year I had decided to fulfill my desires rather than adjust to the high school society as my parent wanted. Having a son who wore make-up and a ponytail was the least of it. After I passed sixteen I would spend my savings from summer work on shoes, clothes, bras and panties and accessories, not on music or video games. My diet was healthy and escort gaziantep my Mom helped with teaching me to cook, but she didn’t support my wearing heels around the house nor would she wash my panties.

“Tracy I cannot allow you to wear these girly garments and therefore if you intend to wear them you must clean them yourself. How can I explain the underwear to your father?”

A couple of weeks later it didn’t matter any longer. My father had discovered a bag from Marshall Fields with my new bras. I’d returned from a shopping trip and didn’t secure the bag in my room. There was a major battle over my gender selection.


While doing my outdoor chores one afternoon I met a woman with her young daughter. They lived on the next street. Cathy stopped and spoke with me regarding cutting her lawn when I could find some time. I think she noticed my bra straps due to my sweaty shirt. Her asking me to help her with her lawn was the beginning of other requests to help about her yard. Several weeks later she asked me to sitter with her three year old one evening. That day changed my life. When she returned around 10:30pm we talked for several hours. I could discuss anything with her and explained my need to dress to her. After several evening of talking Cathy suggested that I could dress while sitting for her daughter. The next visit I did so. From that point forward Cathy help me find myself. She even setup a bureau and closet for my clothes.

I started to spend some part of almost every day at her home, doing my homework, helping with the housework and caring for the little one. I’d spend most of my free time with her, so much that my mother realized something was probably going on. Mom said she wasn’t going to cause a fuss since my grades had risen so sharply. Instead of changing at the station I stopped at Cathy’s to dress each morning. Cathy inspired me to read and work well beyond my grade level but with the freedom to dress I was now wearing only girls jeans and tops, shoes and jewelry to school. Mom told me that she had heard from others of my change in dress and she’d even discussed it with my father.

“Better she doesn’t wear any of it around here or near me, or I’ll beat her.” So I started to spend less time at home, only returning to sleep and shower.


After several months Cathy suggested that I visit her doctor. Somehow she talked the doctor into providing me with a subtle dose of estrogen. We began to see the changes occur in a matter of weeks, just days after my seventeenth birthday. I never felt like a boy again once my breasts began to form. Cathy was very excited and she spent time teaching me how to move as a young girl. Slowly we became closer and my lust and interest in her body was clear.


Cathy spent several hundred dollars getting me appropriately sized undergarments. These were simple but they were the correct size. She also brought me to her wardrobe and selected several old dresses’ which would fit my developing body.

She was adamant, “I will not have sex with a boy.”

So I continued to focus on being the best girl I could be. She clearly was attracted to the girl in me but we did not sleep together.

Several weeks later Cathy gave me another outfit from her wardrobe. This was nearly new; “I wore these right after the baby, before my breasts came back.”

I was falling for her and she seemed to love having me about. But there was a line we didn’t cross. One evening she explained her failed marriage.

“I realized awhile after the baby that I was a lesbian. He left within three month. I’ve found little use for men and they’re dangly sticks.”


“Tess, can you come over to see me this evening?” Cathy was on the phone one Saturday afternoon. She hadn’t said she was going out.

It was a ‘date’, at least to me. I wanted to sleep with Cathy from a moment after we’d met. Yesterday she said that my breasts were nearly prefect. I was happy she noticed but I felt they were too small. Over the past three weeks I’d noticed that she’d begun to dress differently. She looked beautiful and wasn’t wearing jeans. The signals were clear, but I was cautious.

When I’d arrived I asked, “I must have forgot about your date tonight?” She was dressed beautifully in a black dress, 100mm heels and her long hair was up. Her face was ready for a party. I’d never seen Cathy looking so beautiful.

“I’m not going out Tess. We’re staying in tonight. I want to spend sometime getting to know my beautiful Nanny.” She took my hand and kissed it. Then she brought the hand across my smooth cheek.

“Anticipating my love young Lady? Let me take care of you Tess.”

She washed me in the tub, shaving my legs as well as my l genitals and then she did my hair and nails. The hour passed without my awareness, “I brought you a new outfit Tess. Please go to my room and dress. I’ll await you in the Living room with two glasses gaziantep escort bayan of wine ok?”

I found the pantyhose, the shoes and a lovely floral print dress. A moment later Cathy watched me enter the room, “Tess you look lovely. Please sit here beside me.”

Sometime later she was atop me kissing me. No, she kissed me for well more than an hour.

“Come to my bed, I want you to love me, I want you to lick my camel toe.” Cathy had explained that to her the subdivision of the labia was the ultimate female characteristic. I removed her panty and licked her pussy tentatively.

“You won’t hurt me with that tongue dear.”

I slowly developed a sense of her body and Cathy responded.

“Oohh yes my little Lady, lick my pussy, deeper, and push that lovely tongue inside me.” A few moments later I watch the smile on her face turn to intense focus as she orgasmed. We rested on the bed for a bit and she pulled her panty back into place.

Turning to look into my eyes she said “Let me see if you got a camel toe Tess.” I stood and she lifted the dress hem.

“You need to tuck these bits away.” She brought me close and somehow carefully pushed my testes up and away and settled the thong panty. This seemed to keep them out of sight.

“Ladyboys or transfemme don’t present their genitals in this manner. Maybe due to the hormones your little cockette allows you to part your body like a girl. Now let’s try on another gift I got for you.”

I followed her to the other bedroom where she had laid atop the bed a lingerie set of platinum grey and sexy black seamed stockings. The hose were new to me as was the suspender belt, and after removing my dress I had to ask to her to help me get the seams straight.

“These are details a boy doesn’t concern himself with,” she took my hand and we went to the bed edge. “Let me do your face first. I kissed all of the lipstick away.”

I watched as she carefully adjusted my rather simple application of my makeup. Cathy then showed me how to ball up the hose and slip them up my shaved legs. “Now hook the top edge, yes, just like that. And I want you to wear this pair of high heels Tess.”

I had been dressing for months at Cathy’s but when I moved to the dressing closet and saw myself dressed in the just the new lingerie reflected in the long mirror I was shocked. “Yes Tess you’ve become a lovely young Lady,” Cathy had moved behind me and reached to hug me, settling my new breasts in her hands.”

Maybe is was the love I felt from her, maybe the luxurious lingerie and the makeup but I saw myself dressed just so beautifully, I was a woman.

“I want to make love with you Tess. Can I lye with you?”

She needn’t ask again. I moved with her to the bed, enjoying removing first her dress and then her panty.

“No I need to have you in my mouth. Though I’m a lesbian now I still love sucking a stiff cock. Oh and you are quite hard young lady.” She had me within her warm mouth. It was my first blowjob and couldn’t control what happened next. My new lingerie was covered with my explosive orgasm. We played several times a month after that first night.


During the months since I’d met Cathy I barely maintained my social relationships at school. My girlfriends were aware I was distracted but I was maturing much faster than them. Their interest in boys was paramount. While Cathy kept me fulfilled I started to consider my new sexual self. Was the interest in boys sometime I should embrace or was Cathy right. I was a girl who loved girls?

John had grown as well and hadn’t stopped his subtle interest. He was a real catch to the other girls, but I knew of his bisexuality.

One early summer day after his graduation he saw me walking back from Cathy’s pushing the mower. I was dressed in my girl shorts and top and I’d stop trying to conceal my chest months earlier. My hair was in a ponytail and I worn pastel sneakers with ankle socks. I was sweaty and a little dirty from my work. He had stopped his car and came over to the curb, standing below me so I was just a bit taller.

“I’ve asked you several times and you’ve put me off Tess. Can I take you out this evening? We’ll take a ride along the North Shore, just the two of us.”

I knew Cathy didn’t need my help this evening. I bit my lower lip, “Can you assure me that we won’t be seen by any friends? I don’t want my presence to ruin your summer. Girls can talk and then the boys will be all over you about dating the ‘Fag’. I don’t need that attention John.”

He suggested that he could pick me up at the Library, which was discreet and quiet this early in the week. We enjoyed the ride and parked. His kisses weren’t as soft as Cathy’s but I was very excited. “Can I suck you off John?”

Clearly he wasn’t stopping me and I enjoyed giving my first blowjob. I’d practiced with Cathy’s toys for months and I actually enjoyed it. John came quickly but pulled his cock away at the last moment catching his juice in his left hand.

“Now I’ll use this to lube you Tess. Lift the back of your dress.”

“No John, I’ve never been penetrated, you’ll hurt me and it might be very messy.” Though I had been cleaning my bum for several months after seeing a porn video on line of a women getting fucked from behind.

“Tess, don’t be worried, I’ll go real slow and gentle.”

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