• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Dressed So

Dressed So

123

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 a 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 120mm heel, and ran the seven bangles passed my left wrist. I pulled my long hair up into a simple knot and grabbed my evening bag, pausing at the mirror I checked out the outfit and smiled sure I was ready.

Dressed just so, I would search for my lovers in bars downtown, near the river, where the gays and lesbians were of no notice. I'd come to this process by accident years ago while visiting a friend at a Cambridge college. Sarah was a tall brunette beauty I'd met late in 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 19 years old was over 175cm tall and a bit chunky at 70 kilograms. As my graduation 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 been awkward. 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 girls. 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.

"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."

So we had become friends that weekend and when she'd traveled east for college I did so as well. Now I was staying with her for the weekend and 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 the women were of all types, cute and slim, large and butch, 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.

"Well 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 a actually a boy? Come on Maddy! The bar allows only 'women' but doesn't discriminate so those girlie guys get passed the door."

I was attracted to the 'girl' Sarah had rescued me from. Maybe it was her sense of style, or it might have been her 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. I'd not heard her name but she didn't leave my mind the rest of the weekend. From that night forward I found and met all of my lovers at gay friendly establishments. And this woman I met years ago affected my personal style. I found I loved preparing to go out on the town. I eventually realized I loved being dressed beautifully, and at a significant cost, all of the time!

Later that night years ago Sarah gave up trying to seduce me as well. We had discussed the differences long into the night. 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 nearly ten years for Sarah and her type of women 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 politics, the subdivision and attitude of belonging to a group was destructive. Near 3am I stated what I realized. I was simply attracted to girls who had cocks. She cried and we hugged but I used the couch.

Presently 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. My interest in beautiful women with a special bump 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 nine years, had lost four serious romance's, and yet I was a selfish lover. Sure I had helped each of my lovers, seven beautiful 'girls', but had 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. 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 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 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 woman. But you don't love me. I'm a person that grows and does changes, that evolves. 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 three 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 help me become expert with my own makeup and now 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, but though she seemed to be on the same wave, she needed to be her, not her 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, just resist hooking a girl for a couple of months and settle what and how you'll be happiest. She will fall into your lap dear because you are a great 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. I could settle down and help someone just be themselves. In the past I 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' and 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. This was funny given that I had developed the ability to read even the best passing transfemmes, hence knew who or what I was spending time with. These advances just assumed us both to be genetic girls.

After this period I needed to re-explore and I found a new club. I was invited to a small gathering on a Thursday evening just after 6pm. I 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 ran home to shower and dress for the evening. I stopped short 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 taunt 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. My dress had cap sleeves and an open v collar and fell to just above my knee. I slipped on some slingback heels, 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 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 step 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 watch 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 saw immediately her secret, so subtle and yet I knew having been with many transfemme.

"And you are?" I said.

"I'm Juli, one of the original members. We are so happy to have you with us. Can I show you around and introduce 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. I passed a darken hall on the opposite wall from where Juli had directed me. She had indicated there were several private rooms on this floor, with full suites on the floor above. Exiting the washroom I was bumped by a woman preoccupied as she turned into the main hall.

"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 continued food and salads were presented, and the drinks continued. I met over forty women, at least two to 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, but I was looking for someone nearer my age. I had decided to head home when passing a table with three women, one of them shot me a stare, and stood as I passed.

"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 kissed my open hand.

"I liked to stay to 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, see you next week ok?" 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" 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 and hailed a cab returning to my apartment, but 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 Tess was. Maybe 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 cleaned 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 a narrow blush thong and started to gather my pantyhose. I thought again and went to my stocking 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 very long legs. One of my early girlfriends had purchased for me a collection of the correct suspenders, six clasps with a tight waist. The heels would be very important, too low and I'd have lesbians chasing me, too high and I would be restricted to less movement. The black open toe 120mm pair would be perfect, with a very low quarter. Again a different LBD and I was ready and off.

This week the party seemed a bit more crowded and another senior member introduced herself. Georgia was about my age, slim but slight at 168cm. We were walking into the Bar when Tess approached smiling.

"You two know each other it seems," said Georgia. "I'll be off to help any other newbies."

Tess moved nearer "You look just fabulous, and I hope it's snug in your bum" meaning the plug. I considered what I might say but instead took her left hand and brought it to my smooth backside. She immediately traced my spine to confirm her question. "Very lovely, I mean your butt. I'd hope you'd come prepared tonight."

"I'm always ready for some fun Tess, but I worn your jewelry as a sign of my quiet respect. We'll have to go slow if you want to have me to keep. I'm emotionally soft right now and need patience. Where are your beautiful girlfriends?"

"We'll catch up with Alexa and Emma later. Can I bring you something?" I looked into her eyes and saw that Tess was someone special, deep within her eyes there was spirit.

We moved to a small couch, settled and she slid her heels beneath her bum. Now we had some time to learn of each other. I discussed a little of my history, asked about the Club, it's name and why 'HERS' was important.

"Rodin created a bronze called Faunesse and Juli offered the name at an early meeting. I joined in the second year." She told me that nearly sixty percent of the women were serious lesbians while the remaining were all over the spectrum.

"As you noted Juli is the prima transfemme, and there are twelve to twenty others. Oh, and though it may appear as if there is a dress code I assure there are no such rules. I adore your outfit."

She suggested we complete the tour Juli had interrupted last week so wine in hand we entered the hall "The private rooms are simple, a day bed and cabinet, a corner sink. Nothing crazy tends to happen in these, but a lot of kissing and petting."

She moved in closed and I allowed the kiss, she clearly pressing her lead, tongue across my mouth, while her hand reached up my hem and touched the plug. "You're moist for me, I like that in a lover."

"Please take it slow with me Tess. I want to get to know you as a friend before you're my lover ok?" Her fingers lingered at my thong panel a moment longer, and her long fingers spun the plug before retreating down along my leg, passed the stocking welt.

"It will be difficult but I will await your sign next time." I had enjoyed her touch and wearing the plug was a bit flirty.

We returned to the main foyer at the foot of the generous open stair with a skylight "Upstairs are the more private spaces."

Once at the upper level she pointed to a Foyer with four adjoining doorways, all the doors closed and a subtle red light shone. "Those are taken, you can reserve them a week ahead." Turning to the other doors "These seven suites are available as necessary." Two of the doors were open and she moved to the suite on the right.

"This is an extraordinary room, what a view, and the finishes." I moved toward the bathe.

Tess followed me speaking "Each suite is unique and very comfortable, one could stay here without a bother for two or three days." She moved to sit near the window. "Granted that only happens occasionally."

I sat across from Tess and being close again I paused to take in her outfit, details and study her manner. Now I was certain, though there was no true 'tell', I just knew she and I would fit. I stood when I noted the bar, "Care for another drink Tess?"

"You're not a typical lesbian, but you of course know that. But if we start you must be prepared for a storm. I will fill you like a wind and push and pull you into my dance. Can you see yourself releasing for me, humm?"

I turned back toward her, smiled and just looked into her eyes, but I said "Let's meet sometime over the next week Tess, I need to pause my racing heart and consider you clearly, can you allow me that dear woman?" I walked to door, stopped again, looked over my right shoulder to her, still seated. I turned and looked up to the skylight at the deep coming night sky.

"Somehow I'll quell the fire you've stated in my panties until then. Your plug can remain with me I assume?" She stood and her heels sounded her approach, she was near, and she reached for me and we turned to kiss gently, her tongue again slowly exploring me while her hands move across my bottom. I enjoyed being loved by this beauty; her ripe body might soon be mine to please. I had to resist Tess so I moved slightly breaking our kiss, smiled and moved to the stair and left the gathering.

While seated on the sofa I realized I forgotten the plug. I move to the bathe to remove it. Later that night I had a chance to review the clubs members only Website, looking into the background of several of the people I'd met. Though there were guests at the gathering as well, I wished to understand more about club. Juli was listed as the most generous donor to the club. I found on the google she'd made a killing in distressed property in the southwest prior to 2008 and was very comfortably. She was originally from San Francisco and wasn't married now. Her bio stated she'd transitioned at 24 years old. Tess's information was less specific. She had been born in New York and was 28 years old. Her true gender wasn't noted; her education listed University of Chicago with a degree in Art History, and another in Computer Software. Somehow she had found wealth of the necessary scale, as a dealer for art photographers, but also worked at a regular job. The picture attached to her bio only furthered my interest. Her blonde hair fell to below her shoulders but with blunt bangs. She listed her height at 175cm and weight at 55kg. In the photo her blue eyes were intense, more so than in person so I assumed she sometimes wore tinted contacts.

123
  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Dressed So

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 16 milliseconds