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.