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Looking for Tess, Dressed just So

By: MadQuill



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 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 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 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.


Looking for Tess, Dressed just So



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 the 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 as a retort 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 toy 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 femme' and she is near forty-five and there thirty-eight women, some attached. There were two straights but they just didn't fit in and left the club. And we have six or seven transfemmes on the roster as well. Oh, and though it may appear as if there is a dress code I assure there are no such rules. I adore your outfit Madeline." 

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 okay?" 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 six adjoining doorways, four of 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 two suites are available as necessary." 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'd walked to door, stopped again and looked over my right shoulder to her. She was still seated. I turned and looked up to the skylight at the deep coming night sky.

"Somehow I'll quell the fire you've started in my panties until then. Your plug can remain with me I assume?" 

I heard the sound of her heels as she approached. Now she was beside me 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 at the apartment I realized I'd forgotten the plug. I went 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. 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. The other fifty women had varied descriptions of their sexuality. 

Tess's information was less specific. She had been born in New York and was twenty-nine years old. Her gender wasn't noted but I was pretty certain that she'd transitioned. 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 she 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.

My past relationships weren't as sexually driven as it might seem. I enjoyed my liaisons and affairs but most of the girls who had moved in were in need of very specific care. I insisted on strong penetrative sex and mostly resisted providing them the opposite. Since Lisa had moved out I'd focused on learning to appreciate how to treat a lover's needs as my own. Last month I'd spent the holiday weekend fucking a sexy older woman I'd met at a party. During the long weekend she had shown me the beauty of penetrative anal sex. Prior to her request to fuck my bum I had only allowed my lovers to lick me there. All of the girls had wanted me to fuck them with a strap-on and I did sometimes. But I failed to orgasm during these sessions while bringing them off and therefore I didn't offer this unless requested. Never had I consented to having my tight passage entered. 

The weekend with Mary I had reached orgasm as I'd fucked her butt but I had multiple orgasms when she deeply loved my ass. This was a new adventure and required careful cleansing. I had decided to work at it and tried with my toys with success and learned the technique. Patience was important. If I had further explored this act and my body with Lisa or better with Jenna, the brunette beauty I'd lived with for 15 months over two years ago, I might be a married woman now.

I was at the doctor when I received a cell call from an unknown number. "This is Tess. Can you meet me for a drink this evening?" 

Tonight I was busy with a client and couldn't meet, but agreed to do so the following evening. This began a slow seduction but not by me; Tess was after me. 

Our drink turned into a light dinner but I passed off her flirting, "We'll see each other soon enough dear." 

She kept at me. Flowers arrived at the office the next morning and the following afternoon there was a box delivered. Inside were a lingerie outfit, quite beautiful, and a note with a poem.

She said please

she said she feels 

so a young woman

like one 

with desire

for a union 

she must flirt 

must tease and warm 

with fingers 

and other members to compare

The poem was just the beginning for she left a phone message, then a sextext of her bum. Clearly we had a need to get together. I responded to only the sextext, with a smile and an address; she had to pick me up. I was trying to take this slow. To focus on the details I'd previously missed in my relationships so I agreed only to meet for drinks and dinner. 

She'd found a lovely place with a mixed crowd and we weren't the only gay couple. I was dressed to attract her eye and imagination. I selected the pale white lingerie she'd sent me including a very delicate waist suspender. These were fine garments and I wanted to play the part of a submissive lesbian femme. My legs were in sheer nylon hose' with nude colored 110mm heels. She knew what I had on beneath the ivory skirt and white sheer blouse with a scoop neck but I worn a chemise to subtly conceal my body and the soft lingerie.

"You're taunting me but your manner of flirting is very discreet. I'd like to take you to bed this night. To slowly remove lovingly those garments and play over your body with my tongue, then slip inside you." 

She was trembling with excitement yet I played mute, waiting rather than giving her any sign. Beneath the table she'd slipped her right heel off and stroked my legs with her hose' covered foot but I simply sipped the wine and commented on the vintage.

"When I allow you to my home you can bring this along. It's a great Pinot. I'd love that Tess." 

Then I was silent as she continued to speak of her attraction, the massage beneath the table dressing continued. I changed the path of the discussion, asking her to tell me of her first encounter. The story went on nearly an hour. Not about a girl and her but of a slightly older woman. Divorced but with a young child whom Tess help care for. Cathy was instrumental when Tess was fifteen finding and buying her the hormones that started the changes Tess desired. She also helped train Tess about beauty care and makeup. Tess had worn her hair quite long but it was a mess and Cathy brought her to a salon that helped repair and shape her hair while still easily converted with a band to a boy's style. 

Their relationship became sexual when Cathy deemed Tess could pass and only if they were both properly dressed, lingerie as well as dresses. Their loving didn't include any penetration for over eighteen months. Tess finally convinced Cathy to use a strap-on in bed one afternoon while the child napped. 

Tess continued, "Soon after that Cathy stopped calling for me to help with the babysitting and within a month she made it clear our relationship had been spoiled by the act of penetrating my bottom." I saw her eyes moisten but no tears fell. 

"Anyway I was off to Chicago very soon after and classes distracted my memories. Why I can still feel this pain I don't know. Cathy was of course a beautiful and a tender lover. I clearly needed more though and the split was therefore a good thing."

I sat quietly listening and she suggested we head to her apartment. 

"Tess I want you as well but I want us to settle a good foundation without sex, if that's alright with you. I feel it will be for the best dear." I reached across the table for her right hand, a diamond on the fourth digit. 

"That a beautiful stone, a gift?"

"I had a serious male admirer for nearly a year. His true gift was his great cock but he tried to marry me as well. I just knew it wouldn't work. I wanted his sister more than him," she laughed.

So we shared a cab home. She watched me enter the building. Than the cab moved back into traffic. 

Again the next morning flowers arrived and another box and a poem. This time the gift was a realdoe insertable! I smiled knowing I would use it with Tess soon. 

"Stop sending me these toys to my office Tess. The distraction isn't helping me do my work!" 

She asked me for another date, Friday evening, at a surprise location. Reluctantly I agreed so long as she didn't assume we'd be in bed that night. 

She chuckled, "I promise not Friday."

I decided that evening to research the difficulty transfemmes encounter in the job market and business. Tess had an advanced degree in computer software and worked in the IT department of a small international firm. That appeared to be one of the few great jobs and the firm was on the record as supportive of the LGBT community. Her sole art venture was due to meeting several artists at the end of her college studies. Two of these had become big and Tess enjoyed the fruits of their success. 

She would eventually find out about all of my past lovers as well as my financial background. We could be every good for each other so long as I didn't mess it up. I thought of Jenna. How I'd loved her breasts (the best boob job any woman could get), and she had a great cock too. I'd allowed her to simply leave and now I thought to call.

"I know you asked me not to call, but I just had to find out if you're okay?" 

She didn't speak for a moment, "I'm with someone right now but he's in the bath. Email or a text is more discreet girl, you know that." 

She paused, "But I'm just fine. No long term relationship but I'm cool with that. I'm staying healthy and sane, and you?" 

I shared the recent past and we agreed to speak in a couple of months. It was clear she was sleeping around. I guy? She'd not been with a guy in years as far as I knew.

Friday evening Tess arrived by cab and had told the driver to wait. She came into the Lobby and asked for me. 

Via the phone I said, "You're twenty minutes early! But it's fine Tess. I'll be ready in a few minutes. Come upstairs while I finish." 

She entered the unlocked apartment a minute later and I called for her to sit and enjoy a glass of Chardonnay I'd set for her. I entered the Living Room ten minutes later ready to leave to find her looking over my photos and Library collection. 

"This one of you is beautiful but who's the girl?" Her question distracted my attention. I was reviewing her flouncy tiered, cream-colored dress. 

I moved to her side; in my heels she was just a bit shorter, "That one is Jenna but let's not go there right now." 

She turned quickly and kissed me, her tongue finding mine and playing. I noted how quickly my pussy became moist as she felt my breasts. 

"Slow down honey," I said pausing but not ending the kiss. "I love you in this color," I whispered in her ear.

Tess said, "We've got a few minutes," her hand running down my back and started to lift my hem. 

"No we don't young Lady! Let's go before there's an accident. My panties are just a bit wet and not soaked yet."

In the elevator she drew me to her and I felt our breasts touching, hers were just a bit larger. Her nipples erect and noticeable through the fabrics of her spring outfit. 

"Tess, please stop for now I am quite moist. That's what you were trying for, so yes my pussy wants you. The toy you sent me hasn't left my mind. It's quite stout you know." 

She smiled and took my hand and caressed along the front of her beautiful dress. Up until this moment I'd had a wonder about what I felt but wasn't certain. 

"You tuck very well. Or your clitty is quite small Tess." she smacked my hand and kissed me roughly.

"You can't wait to see my clit can you? You've been lusting after me, huh? Well I'm a bit more stout but also very soft, and very attracted to you Madeline and can't wait to fuck you!" 

Her hand reached the welt of my stocking. "You had better always dress just so for me dear. I will for you too." 

We kissed just as the doors opened and my middle-aged neighbor Ms. Lester looked up and frowned. She of course knew of my girlfriends but she didn't like the public display she'd just witnessed.

Dinner was great. The wine perfect and we didn't finish until nearly ten-thirty. Leaving the restaurant our heels clicking on the bluestone slabs I asked, "Shall we have a night cap at the Bar down the street?" 

Tess looked pensive. 

"I'm not going to sleep with you this night. I told you earlier this week we need to go slowly Tess. I think you're too special to lose and want our first time to be just perfect." 

She turned upon her heels, a beautiful and tall pair strapped about her lower leg well above the ankle. 

"Okay. Then let's stop but at a wine bar nearby instead." 

They had a wonderful cellar and Tess clearly knew what to order. The Gamay arrived and was perfect. I failed to read the label until a bit later, Point-G 2006. The sly smile on her face made me realize Tess had a plan and I was the target or the prey. We were seated in a little sofa wrapped about a café table. I had slipped off my heels and slid my feet to the edge while Tess massaged my hose' covered legs. She spoke softly, cooing her words. As midnight approached I softly asked Tess to get me a cab home. 

"Won't you let me bring you to my home?" We were reclining on a sofa and I moved to look down at her. 

"You started this evening making my panties wet Tess and I assure you I want to return with you but I was very clear." 

I stood and slipped on my heels turning to leave. She jumped up and tried to hold me, "NO Tess, not this night. Soon yes, but not tonight." 

I continued to the door, she slightly behind trying to get her own shoes on. As I reached the door a cab was just pulling up and I had my wrap and signaled to the doorman.

"When can I see you again?" she pleaded. 

"We'll speak early next week Tess." 

I turned and gave her a quick kiss then entered the open door of the cab. I was upset and also aware I was being a bit of a tease.

I was so hot for Tess but I had settled my path. The relationship was more important than the sex, at least right now. I thought of our evening, of her touch and the kisses. I hadn't checked my messages in more than thirty-six hours and on the ride home found that Jenna had tried to reach me. The message said: 

"Call ANY time"

I paused to consider the possible benefits of pursuing Tess while re-visiting with Jenna. It could be interesting to better understand what I had lost over thirty months ago. I quickly placed the call even though it was after midnight. Jenna picked up on the second ring. 

"I'm glad you've call. Where are you?" she asked. 

"Please come see me right this moment, please?" I considered how aroused Tess had made me and re-directed the cab to Jenna's new address. 

I arrived and was buzzed passed the entry; she was waiting for me. The mirrored metal elevator door allowed me to collect myself, straighten my outfit and run a brush through my hair. Jenna met the elevator and jumped to kiss me. 

"Come to me you sexy Lady". We entered her apartment hand in hand and she led me to the sofa near the windows. We hadn't seen each other in so long yet she knew what she wanted and I think she understood from my questions last week where to take me. 

"I still love you and miss you Maddie but can you be with me?" 

She paused in her excitement to settle into a reclined position that allowed her gown to fall open. Her lovely breasts were just held by the thin material which fell to her open thighs, just covering the tip of her semi-hard clit. I considered her beauty and shifted closer. She'd clearly showered and re-done her face. 

"Yes Jenna, I need you tonight as well, but I've changed in important ways since we last were together." She smiled knowingly. Previously our lovemaking would include kissing, petting and lead to her entering me after I played with her clit. I would occasionally penetrate her. She simply looked over to the side table. I followed her eyes and saw the fleshy strap-on, proud and erect. 




Looking for Tess, Dressed just So



"Is that what you mean by changed sexy Lady?" She moved and kissed me, while reaching for my skirt zip. Her hands cupped my bottom. I was still wearing the damp thong. "Is that the way we'll play tonight?" The phallus was extraordinarily large.

She started to un-button my blouse. "Can you handle fucking me, humm?" She caressed my breasts while releasing the bra. I felt so alive and my pussy was so wet. Her hand came to my mound. 

"Why are your panties so wet sexy Maddie? Missing me a little or has someone else got you humming?" 

I was quiet, allowing her to slip off the damp thong and remove my chemise and unclasp the bra, as she reached for the strap-on with her other hand. 

"Let me settle this for you," the harness was a flesh colored material and concealed a small protrusion. "Don't worry, we're both going to come tonight, maybe at the same moment humm?" 

I considered what I wanted to do, to fuck her like she enjoyed, allowing her to do my ass as well? She had wanted my tight opening for so long. My right hand reached for the large phallus as Jenna cinched the strap tight and my mound felt the subtle vibration begin. 

"Turn to me sexy Lady, I want to see your cock." I held the phallus and nodded to Jenna. She moved close and dropped to allow my phallus to enter her mouth. Moaning softly I watched as she ran her tongue along the length, across the tip and deep into her throat. 

She removed the phallus slowly, "I've been sucking a bit more real cock as of late, but I need to be fucked. Can you fuck my mouth please?" I trained my attention on the willing soft mouth and slowly began to move into her while holding her shoulder. 

"Watch the teeth Jenna, and hold my balls gently. Kiss the tip girl, yes, run your tongue around the smooth head Jenna. I'll let you in on a secret, I've missed your beautiful tits and your great clit too." 

I pushed her to lay back and this exposed her tight opening. Her thong now concealed her stiffness so I pushed the panel away from her pink rosebud. I ran the moistened cock up and down her perineum, teasing her while my fingers entered her mouth. 

"Suck on these while we get you lubed."

"I won't need any dear. I'm so ready for your cock. Please enter me," So I slowly centered the stiffness and pressed up and into her, pausing with just the large helmet inside. I needed her loving tonight. I needed her excitement. Though I been with her, been fucked by her, each memory was unique. Now we were in bed and she was hot for me.

"That sooo good sexy Lady, yes go slow, I want to feel each centimeter enter my body dear. Ooh that's just perfect, now all the way in please. Oohh yes, all of your cock sexy Lady, press your nuts into my butt!" I leaned forward to kiss Jenna, holding her chin with my right hand, at the same moment I withdrew the phallus some 5cm, then slid back in deeply. 

"Oh Lady that's what I need. I need your cock, fuck me now, yes. Sexy Maddie, fuck me!" I started at a pace fucking her slowly but deeply and kept my face close to hers and our tongues were kissing and licking. Her kisses on my mouth, mine on her cheek, her ears, while caressing her breast with my free hand. We were looking into each others eyes. 

"You still love me, after I hurt you?" I said.

"Sexy Lady you're inside me and my peak is near, yes I do. I do love you. I love your cock inside me. I only wish it could shoot me full of your seed. Keep fucking me!" 

She closed her eyes. I had noticed the stir within my pussy though not penetrated. The vibration began to cause my inner walls to contract and I was going to come. Jenna's tight body was wrapped about the smooth phallus. We had never experienced a mutual orgasm like this before. I increased the pace just a bit and the stimulation at my mound moved just to the right and I started to come and she was gripping my body. Holding me close as the deep fucking brought her own release. She loudly orgasmed as the phallus pounded her tight bottom.

Afterward we lay relaxing in each others arms in the bedroom, with a cool white wine. 

"Will you let me fuck both of your openings this night Lady?" 

I turned to look at her face, "Don't be greedy Jenna, but yes. Maybe after a rest, near morning we'll make love again okay? Why the urgent call tonight? Were you alone or just horny?"

She started a story about her past month, with first a man, then a woman, confusion on her part, but some great sex. The woman wanted her to move in with her and her husband but Jenna worried it might get too kinky. She just needed some time with a friend. My call last week had opened the door so she'd reach for me. I was happy she had called for the release was what I needed. 

"So you decided to find out how sexy your butt is Lady? I've always loved your little hole. Now you'll let me in, humm?"

I decided to be as truthful as possible. "I met someone who insisted I allow her in, over thirty-six hours she fucked me repeatedly and I came so strongly Jenna. I realize you'd tried to get me comfortable with anal for so long. I resisted foolishly I now see." 

Jenna smiled wickedly, "Turn over. I want to kiss your ass Lady," she rolled me a bit onto my side and dove beneath the covers, licking me with intent, then slipped her middle finger into me. 

"You are accessible Lady!" She played there, licking, stroking and rimming me for ten minutes. 

Jenna was calm as she lifted my bum and positioned a pillow. She stroked my back, and ran her hands under to grasp my breasts, thumbing my nipples gently. She moistened my cleft with a lube and then played her clit along my slit and then my anus. Without a word she pressed the tip of her cock inside. I was caught surprised. It was so thick but the penetration wasn't uncomfortable. She subtly eased a bit in, then a bit more and stopped. 

She again grasped my tits, "You are ready Lady. Never before have you allowed me inside your bum. Can you sense my excitement? My clit wants to come inside Lady, may we enjoy this first and special loving." 

Though fully penetrated by her clit this was the first warm cock I'd allowed in my bottom. She was smiling and looked so beautiful. Now I saw it as something to enjoy in a new way. 

"Oh Jenna, make love to my ass please? Slowly, but do fuck me please Jenna." 

I reached around and used my right hand to hold her close to my back. 

"Pooch, you're so deep within me Lover. Stay with me Jenna, stay, fuck me, fuck oohhh " I came again but she didn't pause, just continued to fuck me. She moved off my back and we coupled in a reverse cowgirl and fucked until her peak. I'd never felt a seed eruption inside my bum. 

We stayed close and quiet until she slipped out but she quickly moved to enjoy her seed seeping from my opening. Her tongue soothed my rear until she felt she had retrieved most of the juice. Her lips met mine and she pushed some of the juice into my mouth. 

"Maybe you'll stay the weekend?"

- - - - - - - - - - 

Tess had not been happy I'd left her Friday near midnight. Her own history was surely filled with past lovers but she was falling in love and therefore used the quiet time to consider the next phase of her seduction. She wanted something to come from our meeting and felt she was ready to commit to one woman. It wasn't strange to Tess that we were attracted to each other. She had the advantage most transfemme never have, having transitioned near fifteen. Her skin and hair were as perfect as any twenty-nine year old genetic girl and her breasts had large areolas, unusual for a transfemme. Since she was seventeen Tess had never been mistaken for a boy. This had caused the separation of her parents though once Tess moved away to college her parents had resolved their issues. 

She didn't see herself as anything other than a woman and treated her penis as just a normal part of her world. She had come to Canada to pursue a business opportunity and found the society and the relationships so supportive she shifted her entire portfolio and bought the loft about two years earlier. In this town the lesbians were treated with respect not derision. Because her look was so passable she had always been treated as a lesbian not a transfemme.

She awoke early the next morning to prepare. She had decided to focus all of her energies on me, loving me, making me a part of her life. By eight she had settled her plan and was outside my flat by nine-thirty awaiting my first morning activity. Only I wasn't at home and had turned my cellphone off. She realized something was not in order around eleven but she had no alternative. Eventually she entered the Lobby and asked the Doorman if he could ring the apartment. With no answer she could only wait, but she also started to worry.

- - - - - - - - - 

Saturday morning I'd awoken before Jenna and easily made myself at home. I heard the shower just after Noon and brought her some coffee. I watched as she readied herself. 

"What is your plan for today?" she asked.

I just smiled, unsure I wanted to do anything except stay here with her. "Is there anything you need to do Jenna? I haven't decided to do anything though we could go downtown. There is a gallery opening I could stop by around five but it's not required."

She had partially dried her hair and was applying makeup while dressed in her fluffy robe. "I have to take you somewhere special. Can you be ready in forty minutes?" 

My evening clothes wouldn't do, "Can I wear something of yours?" 

We were dressed for a party and in a cab, "Where are you so intent on taking me?" 

Jenna was beautiful in a black mesh over blush dress, nude hose and black 110mm slingback heels. 

"You'll enjoy this event Maddie. A small fashion show in Oldtown at the Spice Gallery." 

The Spice was an old wood frame warehouse near the waterfront used for various special events. I had a curious relationship to fashion design. I'd spent time while at college walking the catwalk for extra money.

"So you gladly loan me the star of your wardrobe," a Dior seersucker knee length dress, "to show me off, humm?" 

She smiled and pulled my hand to her, to the folds between her thighs, "this is the only thing I want to show you dear." 

I blushed as she parted them allowing my hand to reach the naked skin above her hose welt. 

"Press into me sexy Lady again tonight?" I thought about the offer and turned to kiss her, my tongue playing with hers. 

"Then let's turn this cab around. I'm hungry for you too." But we had arrived at Spice. 

The driver jumped out, I guessed he wanted to enjoy our exiting the tight backseat, our legs and heels on display. 

Once seated in the third row I looked about to see whom I might recognize or know. Several of the women I'd met at Faunesse were near and I noted that Mary, the lesbian who opened my back door, was off to the right near the stage. Thankfully Jenna disliked overt public affection. Even holding hands annoyed her. I wasn't too concerned about word getting back to Tess. She wasn't my girlfriend as of yet just a friend. I waved to several women and then the show started. 

After the first break I saw Tess. She was near the rear, standing and hadn't seen me yet. I recalled that she had commented on the photo of Jenna and me so she might recognize her. Considering my options the show began again. I was distracted thinking of the two women in my life. I barely noticed the parade of beauty, the dresses and outfits, the shiny thin models.

When the show finished I looked in the direction where Tess was previous but she was gone. I was surprised that I was worried. Being with Jenna again felt so right until now. I didn't want to hurt Tess but now I realized I just may have. I decided to not ruin the afternoon and asked Jenna to leave; to return to her apartment. We made our way to the street and found a cab and I didn't see or encounter Tess. 

"What caused you to become flustered?" I turned and looked at my lover. 

"It's of no matter Jenna. Just hold me tight and love me again okay?"

I returned to my apartment late Sunday afternoon. My body was tired and my bottom sore from Jenna's fucking. She used all three of my opening several times. Her seed filled me. Even now I wore a panty liner to prevent it leaking to soil my dress from Friday evening. I didn't look that worn since I'd showered and settled my hair but I felt I needed to good night's sleep. I was removing my clothes when the bell rung but there hadn't been an announcement. Sunday the Lobby door wasn't manned after five. I went to the door but stopped to grab my robe. I was in only my bra and thong. Opening the door I found a crying Tess. Her mascara was running and her face smeared. 

"Why did you run off with that girl? She had her time, now I want you, need you!" she fell into the Foyer and I stooped to catch her but ended atop of her. Tangled by the robe's long belt. 

"Oh Tess, I didn't try to hurt you it just happen. You and I will be together. I need you too my dear. Let me help you." 

I moved to my knees and wiped her face, the tears still coming. "You poor girl, let me get you to the chair. 

"I'll get you a drink," but she stopped me by grabbing my left hand. 

"No stay right here. You do owe me an explanation Madeline. Then I'll decide whether you're still worth all of my attention." 

I explained how I'd come to spend the weekend with Jenna. How I did see her at Spice and how I felt about the two of them. She listened and continued to cry, 

"So you do still love her? Still want her?"

"No Tess, it's not as simple as that. Jenna and I had something very special and she will always be my friend. You and I are starting a journey to find our love. To fill both of our lives with each other. There will be plenty of time for friends, especially those in need." 

She stopped me, "You did let her fuck you? Let her release inside of your pussy? The other opening, the one I wanted to be just for me? Did you let her fuck your ass?"

I paused to let her complete her rant. Let her exhaust her negative feelings toward Jenna. 

"First Tess, we are still NOT lovers."

I moved away but still on the floor.

"I want you to be so but I need it to develop rather than just a rush to fuck. Second, no one owns me nor my body and especially not my tight little ass. Is that clear young lady?"

I was upset that she felt she could control me.

"You need to back off and focus on what I thought we both wanted."

I stood and stepped toward the glass wall. I looked to the City but could see her in the reflection as the sun had fallen. 

"You can have a simple dinner with me here or you can get out and find out what happened to the girl I was starting to love."

She stood and retrieved her bag, wiped her nose, pausing again. She seemed to be thinking. Then she sat down looking at me then out toward the view. She stayed there without speaking for several minutes. 

I went to the bar and poured two glasses of wine. As I moved back toward her I saw her looked down at the floor.

"I don't want to eat anything nor do I want to go. I'm here because I love you Madeline. I have been outside most of the weekend awaiting your return. I'm sorry to crash your Sunday evening. Maybe you can give me that glass of wine?"

I walked a step and extended the glass. 

She looked at me and said, "I'll settle down and consider what you've said. Can I use your bathe? I need to clean myself up a bit." I directed her to the Guest suite but was surprised when I heard the shower.

I tapped on the door, "Tess, I appreciate what has happen but you cannot spend the night." 

She called out her awareness of the time, "I just needed a quick wash. I'll be out and presentable in a few minutes. Can you bring my bag though?" I did so and resisted the temptation to peek inside. It was a small black bag, the one she'd had with her Friday evening. 

I turned from my chair near the window when she entered. 

"I feel so much better. Can I sit with you?" I motioned for her to sit across and she noticed the re-filled glass. "Please forgive my earlier fit."

I smiled, "You look much more presentable Tess and let's just enjoy the evening. Sure I can't interest you in a portion of my small supper? Its very good Sushi from Kazi." 

I went to the Kitchen to gather the plates and sauce. She had calmed down but wasn't herself yet. 

"You're typically so talkative. Let's just relax for awhile?"

She stayed until after 8pm and I was happy to see her forget how the evening had begun. I told her I would call her late Monday evening and we arranged to meet at Faunesse on Thursday. 

I kissed her gently at the door just as the elevator arrived. With the doors closed I returned to clear the dishes and glassware. I consider whether this evening had any impact on my feelings but decided to forget the negative. The weekend with Jenna was fun but something soft in Tess was pulling me to her. Though Jenna was special I was bother by her activities with her gentlemen friends. I couldn't imagine she was soliciting but what if she was? She hadn't spoke about these encounters while we'd spent the weekend fucking. 

I received a text from Tess Monday afternoon. She had to travel to Quebec for a meeting Tuesday so we'd see each other at the Club. 

I was conflicted; Jenna had asked me to meet Tuesday for a light dinner but I said I was over booked at the office. I truly need time away to consider the next step, either with Tess or Jenna. 

When I got home Wednesday there was a gift package from Tess. The note was from a Quebec lingerie store. Inside was a set of dark undergarments from the Graphique label including an elaborate suspender and full fashion black hose. Her poem was short; 'longing to see and feel you'. 

I knew what I had to do Thursday. I called my salon for an afternoon appointment and selected the dress for the evening. I wanted it short enough that all who saw me would want to seduce me but especially Tess. 

Getting away from the office proved to be difficult and I had to shift my appointment. The afternoon would be more hectic than I liked. 

I finished my face and settled to dressing. Tess's plug was on the dresser and since I was clean I moistened it with my tongue and slipped it in place. The feeling was distracting. I removed the sexy hose' and the suspender from the beautiful box. This one had eight clasps and was embellished with macramé embroidery and a cute satin bow about the back-panel concealing the fasteners. The black hose' were surprising; they appeared custom fit to my leg length. I slipped the brazilian panty up and over. My dress was quite sheer allowing a subtle reveal of the undergarments. The chemise added a layer of concealment but I felt so sexy dressed and filled. The plug in my bum reminded me that tonight I was Tess's. 

I arrived a bit late. Most of the women were on hand therefore I didn't immediately see Tess. While looking about a slightly older dame approached me. 

"I'd love to be what you're looking for. I'm Suzanne." 

We spoke while I moved to the queue at the bar, still my eyes wandering across the crowd. I was surprised when Tess came quietly from behind me to hold my waist. 

"You're incredibly beautiful dear. Have this rather than waiting for the barkeep." I turned to her smiling face and kissed her deeply. 

Taking the glass of white wine I said, "I've missed you as well Tess."

Suzanne just shrug, "I'll be dreaming of you tonight dear Lady. Touche' to your conquest Tess!" and she move on. 

After the party finished I agreed to accompany Tess to her flat.

The short cab ride went by in a blink as we sensually kissed and petted each other. He long finger teased my inner pussy and I was quite close went the meter rang. The driver smiled as he took the tip but Tess was two step toward the door.




Looking for Tess, Dressed just So



"Hold on honey," I called to her. She turned as I approached and we kissed on the sidewalk. 

The large noisy elevator stopped on the seventh floor. I was surprised by the scale of the loft yet the rough space was elegantly furnished. We settled on a large sofa near the window and started to explore each other. First removing our garments, then our lingerie. Tess was so beautiful and I was lost in her charms. When she lowering her mouth to mine we kissed as she moved her hands to my breasts while releasing my bra. My hands were in her hair as I pulled her close and slid back into her mouth, then to the side of her neck. My right hand slipping into her panty to find her rigid clit. I kissed her deeply as she caressed my breasts. The oral loving of our tongues was exciting.

Tess paused with me holding her tightly as I removed the last of her delicate undergarments leaving only the taut thong; my mouth now on her right breast. Her nipples couldn't have been more sensitive as my teasing tongue caused her to moan. 

"Suck my clit," and I slipped down to engulf her sweet sex. 

A mere few seconds and I was flooded with her first sweet seed. It overflowing my lips. Tess moved to kiss me capturing it as she did and then settled her tongue within my mouth. We rolled the snowball around. 

I wasn't asleep but I'd closed my eyes as she removed the small plug. I was smiling with her seed still on my tongue. Tess had moved to my pussy and gently slid her fingers into both of my openings, the short finger just barely opening my anus. Then her tongue went lower and she pushed into the tight passage. 

"The plug has helped open you. Can I fuck you here first to help us remember how much alike we are?" I thought it a ruse but in a blink I knew it was the right thought and reaching for her chin, nodded my agreement. 

"Don't be concerned I keep my body very clean Tess." During the past weeks since meeting Mary I'd played with my bottom to prepare for Tess. Now she was nearly in me and it was all I could think about. She stood to retrieve a lube and I noticed she still had on her heels. 

"Please bring my shoes here as well dear." 

I slipped my foot into the first while she glanced down my slim body, the other as she applied the lube. 

"Fuck me Tess, please enter my body and share your clit with me." But she had a different approach. 

"No dear, you need to control the entry and pace. Let me lye there on the sofa and you settle your bum over me okay?" 

This was a good though and we shifted about, me slightly above her but directing her meaty clit inward. I been in this position with my girlfriends many times but her warm clit was at my bottom. She moved the tip along my slit and then stopped. I looked to her face as I started the initial penetration. Her size was perfect and I was quite moist which made it seemed easy. I had lusted about this most every evening for days. I pulled her close and our mouths met.

"Wow, we're together now, Ohhhhh!" Tess moaned as I withdrew a bit and then slid right down allowing her deeply within me. 

I leaned to kiss her again as my hands reached for her breasts than I rested my head on her chest. She was holding me and we both were still enjoying the connection of our bodies. Pushing up off of the sofa I looked into her eyes. 

"Now you fuck me Tess. Please fuck me Tess."

She was slow and subtle but the push was deeply felt.

"Oh yes, that's my girl, fuck me slowly, enjoy my tightness Tess! I feel your clit, oh Tess! Wow you're getting larger as we move, yes, yes, ohhh Tess, fuck me please." 

When I played with my anal toys by myself it took at least five minutes to reach peak but she had me so near I started to pant and moan. Grasping her close to my face we kissed aggressively as she continued. Her clit seemed to swell within me and then she screamed into my ear, 

"I Love You!" just as the rush of her second release occurred. I was startled but still reached my orgasm. 

"Your butt is pulsing on my thickness dear. That's amazing! What the way to start my Love." 

We'd moved to the bed a bit later and continued playing until early morning. Tess' oral loving was extraordinary and I held her head tight to my pussy, my hands in her long hair. Her licking me had caused me to tremble so that I squeezed her tightly for a minute after I'd came. We slept again.

Near morning she fucked my pussy sensually, slowly, for what seemed like an eternity. I had four orgasms that first night and early morning. Sore and tried I fell into a deep slumber.

Tess had prepared breakfast and came to find me lying awake looking at the juice still flowing from my bum and slit. She smiled and ran over before I could stop her to lick me clean; both openings soothed with her tongue.

"I want all of you sexy Madeline. Nothing we shall do is beyond my love. Now grab your robe and a panty and come sit with me near the window. It's a lovely Friday. I have to leave shortly, you?" 

I'd forgotten it was not a weekend and saw the clock near 10am. I was late but didn't care.

"Can't we just shower together and return to bed Tess? I need more of your loving."

She was full of energy and stated her intent "I'll come back by two but I must be at a meeting at eleven-thirty so I need to dress quickly." 

I rolled onto my tummy and watched her from the bed as she prepared to go out. I was still surprised at the pace our romance had taken and happy as well. As I watched her a moment I realized I hadn't thought of anything other than Tess since sometime yesterday. Realizing I'd shutdown my phone as we'd traveled to her place I reached for my bag to check my messages. 

"I like that you shut that off last night Madeline. We had only each other to focus on but now I need to go. What appointments do you have this morning?" Tess said while pulling open her bureau. 

My phone came to life. "Nothing urgent Tess." I saw three messages, one from my assistant, and the others from Jenna. 

"My morning meeting was cancelled late yesterday." 

My assistants confirmed a late afternoon telcon arranged to resolve a minor dispute. I could handle that offsite. Jenna wanted to see me over the weekend. I hadn't considered her since our last meeting had caused Tess such anxiety. 

"Can't you postpone your meeting for a couple of hours Tess?" 

She stopped and looked at me. "You look absolute like what I need. Yes of course I'd like to stay and play beautiful Madeline but No!" She turned to continue her preparations. 

I smiled noting her pique. She had a powerful interest in my body. I wondered if I could have cleaned her up like that. It was just so intimate. Watching her move about I was captivated by the movement of her breasts. These couldn't be implants but Jenna's were and moved nicely as well. Tess was intent as she wrapped her long hair under a shower cap and took a quick rinse. A minute later I enjoyed watching the tresses fall from the damp cap, the color deeply modeled tones of blonde. Pulling the brush through her hair was a bit less heavy and quickly it was neat. 

I reached back and touched my tender puckered hole with my index finger. I pushed just slightly to recall her last plunge; I was still moist from her tongue. 

I smiled with a wicked grin. "Can I kiss your bum before you pull those panties into place?" 

I wanted to hold her near for as long as possible. Tess was a few feet away and stopped and saw my hand at my opening, smiling she dropped her thong panty. 

"I'm a bit more accustom to deep penetration. But if you're quick, okay." 

I jumped up and moved to her feet than slipped to my knees, "Please turn Tess." She pirouetted and rotated her bum so my tongue could lick her tight little hole yet she could witness the kiss. My attention stirred her for her clitty was a bit swollen. 

"That will keep me interested Madeline but now let me get dressed!" She moved away and tried to calm down. 

The coffee she'd made was on the nightstand and I hadn't wanted it quite yet. I drank it while I watch her do her face. She always wore some makeup but her beauty didn't demand it. For a girl born as a boy the shape of her head and face were totally feminine. I watched her spread a simple moisturizer across the cheeks and then brush a light mineral powder. A bit of mascara and then she managed her beautiful lips with a mauve red lip cream. 

"I must run in five minutes. Aren't you late?" 

"I think I can stay. Can I and await your return?" I really could skip the work today, at least most of it. She rushed into the closet still naked except for the thong. The white fabric trying to conceal her clitty.

"I marvel that your beautiful clit seems to have disappeared." 

She turned back and pulling the front panel aside exposed the toy I wanted to play with. Tess said, "I assure you it's tough to restrain after our nights activities and your kiss." 

She refocused on her dressing, donning a bra and chemise prior to slipping a pair of nude pantyhose up her legs. 

"I'd rather not bother with the suspenders for this quick meeting."

She slipped her sexy red painted toes into a white 100mm pair of pumps and then grabbed a simple patterned chiffon wrap dress of white with a bit of black and with half sleeves off of the near hanger. I enjoyed the scent as she spritzed a slight shot to her right wrist as she rubbed it together with the left. Just a subtle hint of female provocateur and she approached me sitting on the bed to lean and kiss me. 

I move to accept her attention and reached out to touch her nylon covered right leg. Her hand was more intent for her fingers moved to fill my still softly gaping bum hole. 

"I will return in about 2 hours to fuck you again. Enjoy all of my home please." Her tongue played deep within my mouth as her two fingers continued to rim my hole. 

"You're causing me to melt Tess. Please stay honey?" 

She moved off the bed and grabbed her bag. "I'll see you very soon dear," and she was out the door. 

I listened as the elevator door closed and the machine carried my lover away. I wondered what I might do with the time. But first I had a naked ass to contend with. I stepped to her wardrobe and found a short dressing gown and some slippers. Tess's feet were near my size thirty-nine. The seed had been cleaned so I skipped the thong. I found some juice in the refrigerator and returned to the bedroom for my still warm coffee. I wondered about my subtle submissiveness. In all of my previous relationships I had taken the lead role but with Tess I was clearly being the one brought along. She didn't make me feel dominated but I was giving up some control.

Back in the Kitchen I sat on a tall stool looking about both the loft and the view beyond the glazing. Now I started to wander about the space of her home. I spent sometime reviewing her books and found a leather bound book of photos. 

The images were mostly recent and included many of other women and several men. The scenes appeared to be at parties or gatherings. Near the back of the folio were several older images that appeared to be Tess from many years ago. One image was a beautiful shot, clearly a pro produced modeling image of her in a sexy dress. I found another of her in lingerie and this one caught me. She was so passable I wondered if the photographer even knew of her secret. I reviewed it to gauge her age, maybe twenty, so fresh and already with full breasts. Her perfect teeth and smile. It could have been for a catalog? 

There were two other old images. One badly exposed and faded. The back was marked in a soft hand 'Cat' and dated ten years ago. This must be her Cathy for it was of a woman about 30 years of age and casually dressed. The woman was looking into the camera, not directly, and with an amused partial smile. She was good looking but clearly a bit reserved. The other was of Tess and Cathy shot with a mirror holding each other about the waist. They appeared very happy in this snapshot. I realized I wanted to have Tess guide me while looking at the images and set the book back but on the coffee table. 

I considered getting dressed and entered Tess's closet again. She clearly enjoying shopping for there were a great many dresses, blouses and skirts, racks of beautiful clothes. I did see that she also had a collection of pants and shorts. On the right side of the wardrobe were two large bureaus. I opened the top two drawers to find an amazing array of special lingerie. Each of the eight drawers was dedicated to a collection of garments, panties and thongs, legwear in packages, bras (neatly settled and nested), chemises and slips, so many suspender belts of various size and detail. Each drawer was careful organized and the clothes folded. I was surprised to find one drawer filled with Basques and other foundation garments for I thought Tess didn't require the help for her figure. She was very shapely especially in the hips. Her waist may have benefited from some surgery. My review of several of the structured garments provided a hint; these were all sized for her, possibly customized. She may wear them as a fetish rather than to reduce or control her figure. There were several open bottom girdles with suspender clips. Others were just sexy bed wear since these were made with minimal fabrics with a lot of lace or embroidered fabric. 

The lower right drawer was filled with toys of all kinds and shapes. Sexy dildos of various lengths and many with two heads, vibrators, made of different materials and colors. Some were quite realistic in look and feel. I paused and studied several that seemed made of a material very close in feel to skin. I brought one to my nose to verify the scent and was happy that these were carefully treated and cleaned. 

The last drawer was for her workout outfits, Lycra and spandex of a multitude of colors, as well as bathing suits. I smiled seeing the several bikini sets though I wondered how that great penis could possibly not be detected within such a skimpy panty. It excited me to think of Tess that exposed in public. I closed the drawers and looked into the mirror. I needed some attention! 

I decided to bathe but not do my hair. The shower cap was hanging near and I used it. Afterward with two soft towels wrapped about me I sat in the side chair the bedroom considering my late morning. I decided to dress but in Tess's undergarments, to surprise my new lover and keep her focused on playing with me. But which outfit? Just then my phone chirped; Tess would be at least an hour delayed meaning I had about 90 minutes to prepare. There were so many choices; would I wear black or white, ivory or a colored set. Most transfemmes enjoy lingerie and clearly Tess was in that camp. I returned to the wardrobe to select some items for consideration. 

Should I wear full fashion black seamed hose with a suspender belt or a pair of holdups? I wanted to appear as much like a present as I could. I considered whether to wear one of her fetish Basque. I found several that would fit. A sexy look but maybe an outfit that exposed more of my skin would be better. I wanted to focus her attention of my butt. These decisions kept me busy for more than 30 minutes before I made a selection. 

I returned to the Living Room and reviewed the operation of her music system. I selected a soft jazz recording and set the volume quite low. Returning to dress in the lingerie I realized I needed an ivory heel rather than my black pair. I found a rhinestone detailed pair with a small 15mm platform but the heel at 140mm. Sexy shoes with this high a heel can be difficult but I wanted her full attention. With my suspender belt about my waist, an ivory French Leavers lace with a skirt detail, I attached the six golden clasps to the welt of the champagne nude with black detailed sheer hose'. The rear clasps had rather large bows attached. I had to pause to align the rear seams, which required the heels to determine the proper position. I looked at myself in the mirror, just long legs and hose and noticed I was moist. 

The bra I'd selected was unusual for it wrapped about my neck with a dual back clasp. The material was so barely there and again I looked to the mirror as my nipples arose. The thong slid along my legs and I touch myself briefly before adjusting its position. I was wet and I tasted my juice. I wanted her mouth on my pussy now but I slipped the garment into place. The chemise I'd considered would provide insufficient coverage so I looked for something a bit longer. A La Perla elegantly embroidered one of ivory was perfect but I needed to adjust the straps a tiny bit. 

After I reordered the wardrobe the walk to the chaise in the heels was nearly too much. The feel and scent of her exquisite silk lingerie was new to me. Pausing I noted a second large mirror on the Living Room wall. I saw myself as ready and clearly a willing, almost wanton slut, awaiting her Mistress's return. Again I considered how submissive I was with Tess. I realized that she had established her role in the first moments of our relationship by handing me that plug. How far I would allow myself to fall into her control I couldn't say just yet. 

Still looking at my outfit and reflection I settled upon the chaise in the Living Room in a manner that assured that Tess would find me. I planned to appear to be asleep but paused when I realized I had forgotten the plug. I quickly scampered back to the wardrobe to the bureau's lower drawer and found another one, a bit larger made of stainless steel. This one had a handle, maybe because it was so much larger. The first two attempts to insert it failed. I needed more lube but decided to try my own juice. Viola! It popped into place and my passage sealed around the protruding handle. I had come to enjoy the feeling it provided. Last nights play had produced the most intensive orgasm of my life and I was shocked that this occurred while she fucked not my pussy but my bum. 

I recalled an interview I'd seen where a famous Porn Star talked about her love of anal and stated that her audience both enjoyed to watch her bum get fuck and she loved the stronger fulfillment she received from the backdoor sex. My climax early this morning had been just so powerful. She had me on my back lying on the high bed. Tess had stopped plunging and had just held my shaking body. I don't recall her removing her clitty or slipping beside me to fall off to sleep. 

I moved back into the Living Room just as I heard the whirl of the elevator motor. It may be Tess! My bottom was pointed toward the entry as I lay on my right side. I'd moved the slip aside to allow her to see the cleft of my butt. A minute later I heard Tess's called from the door but I didn't respond. 

"Madeline? I'm back, Oh dear." 

I hear her stop, pause and then the sound of her heels moving off toward the bathe. She stopped again and turned back to approach me but again she seemed to stop short. I wasn't certain why until I hear her move back into the wardrobe and heard the shower. 

An eternity passed as she padded about just at the edge of my hearing with the soft Coltrane playing beyond. Then I heard her heels approaching, off the carpet, and then clicking on the polished concrete. I stirred slightly as she stood over the chaise. I felt her right knee beside me on the cushion edge. She reached down to brush the hair away from my cheek and I looked up to her face but noticed the clitty at my mouth. 

I looked up into her eyes as she softly pushed her sex into my eager open lips. The meat was semi-hard but quickly stiffen as it moved deep passed my tongue and slowly entered my throat. I paused her entry and allowed my mouth to gather more saliva to bathe her clit. I tried to smile as I sucked her but her subtle thrusts though not aggressive still didn't allow me to pause. Deeper Tess slipped into my body and again I paused her to re-position my throat for her penetration. 




Looking for Tess, Dressed just So



"So you've been thinking of me huh? I had trouble focusing at the meeting as well. I love looking into your eyes as you love my clit with your mouth and tongue." We were moving just a bit, she pulling out only about two centimeters of her clit. 

"Now I think your throat is ready. I'm going to fuck you." 

I gave a smile with my eyes and she began, just a bit further out and slowly since my throat had grabbed her length. My private practice had enabled me to breathe without panic through my nose. Tess smiled and caressed my face and hair as she increased her rhythm. Then I felt her turning the plug with her other hand, slightly extracting it from my bum only to release it and allow my ass to seal around it again. 

"So now you get to enjoy my seed," she said just as she erupted when her clit was fully back in my throat. The amount of seed wasn't great but some did escape my mouth. She bent down and kissed me cleaning the dribble from my cheek. 

"I hope I'm everything you expected Maddy. I'm falling in love with you." 

I reached up and hugged her while she continued to play with my butt. I moved to stand and we kissed, our mouths wide and our tongues intertwined. The heels made me taller by almost five centimeters. I felt the fingers of her right hand rimming the edge of the handle protruding from me while her left caressed my breast. She stopped and bent to pull my thong away leaving it dangling near my knees. My body was very aroused and yet I wanted to focus on hers. I slid the left strap of her Basque off of her shoulder exposing her breasts and I leaned to kiss the nipple of each. 

While I worked my tongue at Tess's nipples her fingers were now sliding about my vulva using the moisture to further open my bum. I was surprised how comfortable I had become with using my anal passage for sexual pleasure. Tess's initial attention was the event that truly opened me. Her gift of a stone plug had so surprised me. The forwardness of the gift, the assumption of control, was what had brought us to today. 

"Should I enter you or would you like to fuck me?" she asked. 

I was happy with her suggestion since using her Realdoe had been one of the highlights last night. "I would love to be inside you Tess. When you had to leave it's all I could think of, me fucking, you fucking, humm." 

She smiled, "I'd love to be fucked so let's go to the bedroom." She removed her fingers from my plugged opening and turned toward the other room. 

"NO, I want to take you right here Tess. Settle yourself on the chaise while I attend to my cock." I pushed her slightly to clarify the role reversal. 

"I hope you're moist enough. There, you have an assignment."

She understood and did exactly as directed and I noticed her beautiful hose' and heels. 

"I do love your CFM's dear, and the way your ass is framed by the straps and hose. I intend to enter you from the rear, get yourself ready." Before walking slowly off in the tall heels I bent and kissed and licked her cleft.

I recovered the insertable from the floor just beneath the bed skirts and washed it. This dildo was the stout version and fit snuggly in my honey pot. We had agreed to generally fuck with our thongs in-place. This seemed to help Tess feel more womanly, her clitty a bit concealed. It also aided retaining the inserted phallus. I stepped quietly to the doorway to inspect Tess. She had placed a large red pillow atop the chaise that lifted her rosebud to a perfect angle and height. I paused just watching. She had clearly used her mouth to lube her passage, as I saw the spittle glisten. Her knees were spread a bit and the heels showed a bright red sole. She had one hand on her bum holding the cheek wide open. I almost ran to get my phone for a snapshot. Her breasts were relieved from the Basque, which was taut across her sloping back and I studied the detail to distract myself as well as provide a delay. She needed to learn patience as well as I did. 

I moved slowing across the floor, my noisy heels making my presence known while I lubed the cock. I intended to not pause and the speed I walked toward the chaise allowed me to consider the aim and angle of my penetration. I noticed that Tess worked to keep her eyes looking out the glazed wall. There would be no surprise but the anticipation made me very aroused. As I reach the carpet edge I carefully held my cock and moved the last steps without a sound. 

"Uggh! Madeline, yes, ohh, ohh, ahhh, so big my lover, more, more, deeper please." 

I rode her for a few slow strokes pushing into her hole then I adjusted my pace as she relaxed. The large plug was still within my bottom. It banged the end of my insertable through my inner wall as I moved. I pulled her right heel covered foot toward me to help steady the action. I noticed she had her left hand at her clit bump and was tapping it with our rhythm. My half of the fun stick was bringing me closer to peak but I wanted to watch her sunlit face as she came so I slowed my thrusts and moved her first to her left hip while pulling her down toward my cock a bit. Then I shifted her to her back. 

I could now look into her eyes as well as watch her breasts heave. I grabbed both of her hose' covered legs bringing them together and high above her bum. Now I was certain we were both near and I could fuck her fully. I pushed into her tight bottom deeply. The plug and the deeply settle end of the realdoe were causing me serious joy. Her sighs changed to moans and her breathing was sharp. I was so wet but also sweating from the excitement. 

I was growing a little tried and accidentally allowed the cock to slip out of her butt. I used the pause to lie on my side, still able to get at her hole and we proceeded to fuck. Tess held her bottom a bit and I grabbed her waist to better penetrate my babe. I decided to slow for a full 20 seconds. She would be so close but I would have her even more excited when I plunged deep again. 

"More, more lover, fuck me now, I want your great cock . . ." 

As I started the last push into her I'd moved my hands to her breasts and she screamed and grabbed my neck pulling me to her mouth. I started to orgasm at this moment and a loud groan of intense joy came from my mouth as we kissed. Her seed oozed to her tummy while I held my fake stick deep inside her ass. I was again surprised by the intensity of our sex. The act of fucking Tess had re-leveled the relationship; she was my bitch. 

"Aren't you a lucky girl Tess. Someone loves your bum three time in less than a day." 

We remained somehow atop the chaise for a while longer. We kissed and snuggled not wanting the bliss to depart. 

"What's next for your day dear?" 

She smiled as she turned to kiss my mouth, the realdoe cock slipping from her hole. Then she pushed me to allow her to pull the plug out and I moaned deeply again.

I considered the requirements for dealing with the telcon I had on the schedule. "Do you want to accompany me to the office?" 

The End 

By Madquill