Looking for Tess, Dressed just So

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Please remember this is a copyrighted work and all legal disclaimers apply.

This story is a subtly revised version of the story “Dressed So”. The intent is a response to a comment from a reader. She suggested that the story “. . . belongs in the Lesbian category. I arrived here from a ‘stories like this reference’. I found myself captivated by your series that was romantic, with character development, and quite different; re: lesbian and transwoman. I ‘d never thought about this possibility in real life. You created a beautiful story that really excited me erotically to a different possibility.”


Looking for Tess, Dressed just So

As evening approached I entered my dressing room and set the glass of Chardonnay on the bureau. I had planned to wear a simple black dress but decided the white V-neck with a fitted waist and open back would look best. I’d lost nearly two kilos due to my work regiment the past two weeks and decided to enjoy the slimness this evening. The mild winter allowed some freedom from the boots and long sleeves and a sheer nude pair of hose’ would suffice. After trying several pairs of shoes I selected white pumps with a 110mm heel, and ran the seven bangles passed my left wrist. Pulling my long hair up into a simple knot I grabbed my evening bag. Pausing at the mirror I checked out the outfit and my lipstick. The liner edge looked good and I smiled sure I was ready.

Dressed just so I would search for my lovers in bars downtown, near the river, where the lesbians were of no notice. I’d come to this process by accident a few years ago while visiting a friend at a Cambridge college. Sarah was a tall brunette beauty I’d met late in high school. She was from a rival town and I hadn’t realized, that she was gay and that she was attracted to me. I’d blossomed late and at seventeen years old was over 175cm tall and a bit chucky at 70 kilograms. As my senior year came rushing on I’d lost the weight and settled at 178cm. My mother had been a stunning tall maiden my father had said many times but I’d taken little notice of her beauty since I had been clearly an awkward teen. Anyway, Sarah had come into the restroom a moment after I had finished in a stall and was washing my hands. She stopped when she caught a view of me in the mirror.

“You’re not like these others girl. With no makeup, dressed like that, and just running out? Not even a little lipstick?”

I’d not realized she was addressing me until I turned to my left as she crowded me. The others seemed used to her and just muttered. I wore a simple top and jeans with sneakers. The pant legs were rolled up passed my ankles.

“We’re hunting here girl, and you don’t seem to understand the importance of presentation? Granted you are lovely but these smelly jocks with bad vision need help with their gene selection. Mating is what keeps us going and you’re not helping them nor yourself.”

We became friends that weekend and when she’d traveled east for college I did so as well. The second month of college I traveled on the train to stay with her for the weekend. After a simple dinner she brought me to a club that had a lot of women, shit, it was only women. As we entered and she started to introduce me to each of her friends I realized she was gay. The looks of near rage and hate passed back my way showed me that they had deduced I was her lover. Maybe she had prepped them, maybe not, but several of the girls we met were pissed.

At the bar and on the dance floor there were women of all types, cute and slim, large and butch; some were dark and angry. There was another group of quite well dressed girls as well. I tried of the aggressive stares from Sarah’s friends and moved across the room and started a conversation with a lovely blonde in heels. She smiled when I said I liked her skirt, a soft olive green but of cashmere.

“Thanks, I’m Gerri. I love the feeling on my legs, and it was on the discount rack at the Limited. Most of the other girls here don’t share with us. What’s your name?” I was about to give her my name but thought about her comment.

“Why won’t they ‘share’? Are you from a different College or planet? Or worst, the visiting team?” At that moment I felt my arm being grabbed and turned to find Sarah at my left.

“We keep to ourselves Maddy. These ‘girls’ aren’t female. They may look like us but their fakes.”

Sarah had me across the room quickly, “Couldn’t you see that ‘she’ was actually a boy? Come on Maddy! The bar allows only ‘women’ but doesn’t discriminate so those girlie guys get passed the door.”

Maybe it was her sense of style or it might have been her studied beauty. Instead of wearing jeans and flats with just a bit of makeup like Sarah and me this woman was dressed; hose’, jewelry, the heels, even her hands were beautiful. As Sarah went off about ‘them’ I wondered about Gerri. She didn’t leave my mind the rest of the evening.

Thinking back to that weekend eight years ago I know Gerri affected my life as well as my personal femme’ style. I’ve found I loved preparing for each Sivas Escort day whether to just go to work or to go out on the town. I’d realized I loved being dressed beautifully and at a significant cost all of the time.

Late that night years ago Sarah seduce me. I became aware of the loving women offered. We were discussing the differences of lesbians and ‘them’ for over an hour when I’d reached to grabbed my beer and she kissed me. Our pent-up sexuality had control and she led me to her bed. Her mouth was all over my body and her tongue seemed to be able to read me. I watched her lovely bottom as she removed her jeans. Seeing a bare mons for the first time I realized I had much to learn. I loved the nakedness, the smooth skin near her pussy and she was very good at loving my body as well. I had touched myself but Sarah was my first lover. We made love atop one another in what I’d later learned was sixty-nine. The connection to Sarah and the sex I couldn’t sort out. I wanted more of her body but I wasn’t in love. The lust caused by her mouth on my pussy made my head swim. Afterward she had some very good cannabis and soon we were hungry.

On the walk to the Diner we saw the same group from the bar and the discussion started between us again. To her these other girls weren’t quite right. To Sarah they stood for all the wrong things and messed up the queer agenda. It took more than ten years for Sarah and her type of female to accept that these other girls were in fact in need of support and could add to the agenda rather than distract from it. I didn’t care for any of her mis-directed politics. The subdivision and attitude of belonging to a group was destructive. Near 3am I’d stated what I realized. I was attracted to girls who had a penis. She cried a little and we hugged. Early as the sun entered her room I awoke to see her naked bare body and I stirred her with my tongue. We had the best release when scissoring each other; her naked pussy on my furry mons. I knew I was going to love women from that day on.

Now I live in a Canadian city where the subculture of sex isn’t treated as a negative, just part of life. My friends are from many political camps and lifestyle issues aren’t cause for segregation. My career has evolved to provide me with an ample salary and the freedom from the office suite. My professional work allows me to set my schedule and for whom I’ll produce. But my love life has stalled. I’ve had many women lovers but my interest in beautiful women with a special bump hasn’t been sated.

After school I met and lived with an older high femme’ and she nurtured and developed my appreciation of style and the role it has come to play in my life. Clara also helped me become aware of my omnisexual nature. At thirty-five her body was still taut and smooth. I loved the nakedness of her vulva and her spirited loving seemed like an adventure. Each night she would find some new way to get my attention and bring us to peak.

Her loving was as special as were her relationships. The time spent with her girlfriends and her toys slowly helped me understand my nature. Meeting independent females whose appetites were so varied was important. Her friends and ex-lovers were of course years older then me and there was an openness to our relationship. She taught me the importance of submission as well as penetration. What a bossy femme’ though.

Her world was comfortable due to an inheritance and we loved each other sincerely. I think she wanted me to stop working but she had shown me that I was still exploring and growing. Having been her lover for sometime I’d eventually introduced some of my girlfriends.

“The transwomen you’ve been with Madeline are really more or less femme’ lesbians not shemales. You seem to find and select only the girls able to pass without question. They’re all small-breasted girls too. Two I’ve met I wouldn’t have guess their birth gender if you hadn’t suggested their history. I really liked that babe from Canada. What was her name? I would have slept with her in a heart beat.”

Jenna was what had drawn me to Canada. She was amazing woman about ten months older whom I’d met the summer after college. She had studied near me and we’d crossed paths several times. She must have been living with one of Clara’s close girlfriends for we met again at a cocktail party in a garden.

“It’s been, what, two years Maddie?”

She looked wonderful in a vintage floral dress in white with a gradient flower print. Jenna was a sexually charged femme’ and she was quite comfortable among the group of successful lesbians gathered in mid-July.

We’d kissed cheeks and I’d introduced my lover, “Jenna, more than three but let’s not count the years.”

The following day Clara suggested, “I see your old roommates, these other girls, as a research project. You are trying to decide just how much cock you needed. I’m more casual when it involves a penis. Sometimes I just want to suck some dick and get fucked.”

She and I drifted apart after spending three years together. My professional Sivas Escort Bayan path got in the way of her travel. She would call from some exotic place and ask me if she could sleep with a girl she met or some cutepie with a nice cock. I didn’t want to get old with Clara but looking back she was a mentor.

Since resettling in the north I’d been with Jenna and two other very different transfemmes. My heart went flat last spring when Lisa informed me that she had come to the conclusion she wanted a vagina. I love vaginas but having my own is plenty. I needed someone or something to fill mine. The break-up lead me to realize I had been searching now for eight years, had lost four serious romances and yet I was a selfish lover. Sure I had helped each, four beautiful ‘girls’ and two gorgeous femme’ lesbians, but I’d restricted my heart. I’d told myself I was protecting it but I was purposeful. I kept an eye on my girl’s development anticipating their next move. Maybe that was a trait I’d learned from Clara. She wasn’t to blame for my failure to commit though. I knew there was chance each would move on, something would lead to a breakup as their needs changed. I had felt I was in love with the four but I was just enjoying, lusting for their individual beauty. Lisa was the latest and near to my heart. We’d been living together for five months. She was a few years younger and though beautiful, had real conflicts within about her sexuality.

I’d thought we’d worked through her issues and hoped we’d be together for a long time but as she said when she was packing, “You just love the scent and feel of my body. The twin characteristics that make me a special lover and a woman. But you don’t love me. I’m a person that grows and does change; I’ve evolved Maddie. I could have been a loving partner. You’ll eventually understand what love is but try and be alone for some time and find out why you are you.”

Her five cases were in the hall and she was dressed in a great A-line with sheer hose and 100mm black slingbacks, her auburn hair partial up. She had helped me become expert with my own makeup and now as I looked into her light hazel eyes and cried, of course sad for her leaving but more because I realized she was correct. I loved dressing her and settling how we’d look together just as she loved making my face. Though she seemed to be on the same wave she needed to be herself. Not Lisa for me. I was going to miss her beautiful cock though. Sure she passed without question, unless you found her in only a panty; it straining to keep her 15cm flesh down between her perfectly shaped thighs.

“You will find love Maddie just resist hooking a girl for a couple of months and settle what and how you’ll be happy. Then the perfect mate will fall into your lap dear because you are a great lesbian and your kissing is special, a lover and unique in your interests.”

I didn’t go out for three weeks after Lisa fled though I did invited several old friends in for dinner and sex. Each gave me a similar view on my lover’s query. Could I settle down and help someone just be herself? In the past I’d needed the joy of the new to keep me alert and sated. They each felt my needs were primary to theirs in the relationship hence the split. Clearly my emotional maturity was at the core of the issue. I had some work to do if I was truly to find love but did I really want this? Maybe the rotation of beauty was part of my need? I decided to stay single for at least six months and gathered my various toys as a substitute and reduce my wandering. I visited only one gay venue during this period, tending to meet others and friends at traditional bars. I discovered more than a few girls that were attractive but though we flirted I resisted the temptation for an overnight. Some months into the forced behavior change I noted more preferences, which type of woman I did need.

I also discovered that hanging with a woman in a traditional bar lead to other issues unfolding even if society allowed gay women a place. I was surprised at the second attempts made while sitting enjoying time with another woman. Men would press their advantages but women could be crazy. On two occasions the risqué behavior of women who wanted the attention lead to or caused a short hen fight. It seems that to closeted lesbians seeing two sexy women close at a bar is a signal.

After this period I needed to re-explore and I’d found a new club. I was invited to a small gathering on a Thursday evening just after six. I’d skipped the last work hour to properly prepare for the evening. A new LBD was set out, as were my other furnishings before I started work that morning. I had a salon visit at lunch and after work stopped home to shower and dress for the evening. I paused naked in front of the tall mirror in my dressing room; my 31 year old body still had lift, the breasts a nice but modest size, my butt taut and without a bit of cellulite. The dirty blonde hair fell softly to the middle of my slim back. Not quite an athlete’s body but close. I dressed in the lingerie Escort Sivas as I considered the new mindset. Stepping into the dress with cap sleeves and an open V collar I reached to the zip. The hem fell to just above my knee and I slipped on sexy slingbacks. Checking my face I felt Lisa’s training really helped with my makeup. I grabbed my evening bag and ran to the elevator for my taxi was waiting.

The taxi pulled to the curb of a 19th century factory building. A small deep grey plaque with white script letters just beside the door the was the only identification: Hers.

I didn’t ring due to the sound of a lock release and noticed the security camera overhead. Leaving the large elevator, manned by a serious hunk, I stepped toward the jazz music coming through the heavy steel fire door. Again a big male was stationed and took my simple wrap. Everywhere there were beautiful women dressed to kill and smiling. The setting sun was streaming through the industrial windows at the sharp angle of early spring. This felt like a great new start. A hostess in a simple black maid’s uniform approached me carrying a tray with flutes of champagne.

“Welcome Ms. Quill, the staff is happy you’ve joined the Faunesse. Enjoy and let us know how we can make your evening special.”

I smiled and watched as this beautiful young woman moved passed, her sexy bum moving beneath the simple fabric. I watched a moment longer then moved toward the glazed wall where several others were gathered looking over the City.

“Hello, and welcome, you must be our new member.” I turned to my left toward the soft voice and looked at another beauty.

“And you are?” I asked.

“I’m Juli, one of the original members. We are so happy to have you with us. Can I show you around and introduce you to some of the others?”

We moved about the space, meeting members and a few guests for over an hour. I asked for the restroom. Walking to the darken hall on the opposite wall from where Juli had directed me I noted the several private rooms on this floor. Exiting the washroom I was bumped by a woman preoccupied as she turned into the main room.

“I’m so sorry, I’m a bit blind after that,” she nodded over her shoulder as if I’d understand.

I was dressed appropriately as the others had clearly prepared as well; many LBD’s and sexy legs were present. As the evening became darker food and salads were presented and the drinks continued. I met over forty women, at least two which I was very interested in getting to know. Not to say I couldn’t have enjoyed the company of each person I met. I simply had a different perspective. Juli was a bit older than most of the women but she was still stunning. I was looking for someone nearer my age. I had decided to head home when I passed a table with three women. One of them shot me a stare and stood as I walked near.

“Leaving before we’ve had a proper introduction?” I pause and turned toward the table.

“I’m Tess, but I’m not a lost milkmaid. Can you stay for awhile longer?”

I liked her immediately and when she was by my side she reaching out for my hand, but took me by the waist instead and she kissed my open hand.

“I’d liked to stay and get to know you Tess, and your friends,” but when I turned back toward the table the two others were moving off in the other direction. “But I’ve got to go. Maybe I’ll see you next week okay?” She smiled and slowly released my waist.

“I’ll be waiting, you’re worth it and I’m sure of our next liaison. Until then, hold this for me,” as I’d turned she handed me a small stone object that I couldn’t understand. “Slip it into yourself to remember our first meeting.”

I dropped the gift into my bag without thinking or looking at it. The doorman had hailed a cab and I stepped in and car moved away. I looked out the window for Tess was at the curb.

While riding I removed the object from my bag. It was about 7cm long, slightly flared, than I realized it was a discreet anal plug. I smiled thinking of how forward this woman was. Certainly we would see each other again.

The next week of work really pushed me and I was happy when the HERS alert text arrived on Thursday morning. I cleared my late afternoon schedule to allow some time to prepare. As I entered the dressing I glimpsed the plug Tess had given me on the jewelry box. I’d forgotten about it all week. An extra cleansing was required now so I stopped dawdling and got started. Once my bum was clean I reached for the strapless blush bra first and settled in and hooked it into place behind my back. I had selected a panty but put it aside for the narrow blush thong and started to gather my pantyhose. I thought again and went to my hose’ drawer for a unique non-lycra nude pair with a red welt and seam. I knew exactly whom I was hunting after all these years. With the suspender in place I balled the hose’ and ran them up my long legs. One of my earlier girlfriends had purchased for me a collection of the traditional but beautiful suspenders; six clasps with a tight waist. The heels would be important as well; too low and I’d have the butches chasing me, too high and I would be restricted to less movement. The black open toe 110mm pair would be perfect with a very low quarter. I’d selected a different LBD, slipped on my jewelry and I was ready and off.

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