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.