• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • A Visit to the North Ch. 05

A Visit to the North Ch. 05

12

This is a mystery story of Annabelle's life and the changes she encounters. The characters are all fictional. Please read the earlier parts. Please leave your comments.


Florence was a beauty that had left Indiana at the age of seventeen. She had met an interesting older woman and they became lovers. This mentor taught her the languages and the character of a lady during those three years. At twenty-seven she had joined Mastress. She was 173cm tall with dark hair and skin of a warm tone that implying a southern European origin.

Mastress was in her study have a simple poached egg and her cup of London Fog, Earl Grey with a little vanilla and steamed milk.

"So did Annabelle enjoy your attention last night Florence?"

Florence was wearing only her robe and heels since she had just left me.

"She couldn't ejaculate the last time I fucked her. She climaxed but the sheets weren't soiled. I made love to her bottom four times Mastress. Anna should sleep until afternoon."

Florence continued as she came to stand beside Mastress, "She did dream though, talking of her woman Barbara. On another point though, I wonder if we should adjust her hormone dose lower this week?"

Mastress asked, "How quickly did her clit rise on the second stimulation?"

"Ha, immediately! But by the third she didn't stiffen. Who was the first to penetrate her while under sedation?"

Mastress considered the question, "I think I recall asking Margrette. Does it matter? I agree we'll lower the hormones a bit. She's been talking during her sleep for weeks. She seems to think her wife will want her back. In eight weeks Annabelle will be comfortable with her new couple."

Mastress was still looking out to the City, "What size cock did she have in her bum last evening?"

Florence was specfic, "15cm long, medium realskin attached to my 300 harness with the vacu attachment. She may be ready next for a large dildo but I suggest we increase her opening."

In Georgetown Michel was also early for she too wanted to understand her prey. She watched as Barbara entered the Bar but did not wave. The submissive had suggested her appearance while speaking via the phone so Michel was pretty certain. She watched as her potential new playmate removed her coat and moved to an empty stool about 10 meters from her. She thought the ivory and soft pastel pink skirt pairing quite lovely and most important this woman was beautiful with a full bosom and a great bottom.

Michel sat studying the woman for a few minutes. The opportunity to have this lovely woman for the weekend was a surprise. Their on-line chat didn't provide enough background on this Barbara. That name wouldn't do. She would call her Pia. Her submissive character was stronger than her chat had implied. This Barbara looked uneasy, maybe a little afraid. Michel would settled her down. She stood to approach her.

"Are you waiting for me Barbara?" she said quietly to prevent the barkeep from hearing and causing a stir.

Barb was slightly surprised since she'd not seen anyone enter. "Oh, why yes, I am Barbara. You must be Mich, I mean to say Mistress?"

"Very good my beauty. Yes dear, it shall be Mistress. Come join me at my table. I only arrived a moment before. Let's seat here and talk. I will get you some wine."

"Yes please," Barbara quietly said.

Michel sat very close to her and just looked carefully at Barbara for a minute.

"You are remarkable for the opening you've offered Barbara and I love your outfit. It makes me want to help you all the more. Do you find me equally interesting?"

Barbara paused for a bit to consider the situation, looking into Michel's eyes, then to her breasts. She was studying the woman's character and poise as well as her dress, and the need to be a little submissive. She had a goal. Barb was excited by the woman but thought to herself quickly.

'Stay focused Barbara, you need this woman for information.'

She looked downward and squeezed her hands tightly. She did find Michel quite intriguing. Michel was a little older than Barb, also a little taller and she looked like a size ten while Barb was still an eight.

"Yes Mistress, you're quite beautiful. I love your satin black dress and your pearl choker."

She hoped her compliment had come off correctly. Was she crazy or was finding me more essential then all else? The two quietly surveyed each other before a waiter had arrived.

Michel slowly lower her hand to her lap and extended to touch Barbara's thigh near the left knee, just out of sight. Barbara jumped slightly and a soft gasp escaped her lips. The waiter was busy at the bar and still hadn't come to the table.

Michel spoke as she slowly moved her fingers along the sub's leg.

"I too love these true nylons. Mine are French and they tend to hang a bit loose at the ankles when we sit. It's an unmistakable detail."

Michel's long middle finger moved over the suspender clasp and continued higher reaching Barbara's flesh above the welt.

Michel left her fingers on Barbara's naked thigh as she spoke, "You've gone to a great deal of trouble to be here. I wonder exactly how you're handling being this close to the one you want to lead you away?"

Her finger had reached the fabric of Barb's thong. Michel couldn't miss the moisture and lightly rubbed Barb's slit through the panel.

Michel was looking deeply into Barbara's eyes, "I know how to bring you along but there will be many changes dear."

The barkeep came near and Michel ordered a bottle of Chardonnay. Michel's fingers paused as she spoke to the barkeep. The woman left them to get the wine.

Michel's fingers moved slowly, "I love how you're showing your appreciation of our arrangements."

Michel then slipped her finger beneath the fabric of the thong and into Barb's labia folds. Barbara's breathing was sharp and she realized how wet she'd become. She was losing control of the situation.

Michel spoke slowly while her finger reached the moist opening, than she pressed her digit into Barb's pussy.

"My slut, may we retire to my car, then home? I live quite near on the hill. Less then two blocks."

Mistress withdrew her fingers and licked each while Barb continued to look into her eyes. "Humm, you do taste lovely Barbara."

Barb considered that she knew nothing of the area let alone this Mistress. Her friends were away for the weekend so she couldn't call for any true help. Maybe she had to let this pass. Just drop the thought and return to Julie & Liz's apartment by herself. That was her intent when Michel lifted her fingers to Barb's mouth. Barb slightly opened her lips to taste her arousal. She could smell Michel's as well.

"I think you're about to change your plans Barbara. Please be with me this evening. I won't bite."

Michel stood having released the clasp of her necklace. She moved behind Barb and lifting Barb's hair placed the choker about her new sub's neck.

"This is mine just as you will be Pia."

Barb was conflicted and then she realized she was completely without the discipline to leave. To this woman she was giving free rein. She watched as Mistress sat down shifting her chair a little further away.

Barbara looked across the small table and said, "A moth to a flame I guess."

Barb had initiated this contact to resolve a plan. An investigation of how and why was her intent. But here she was without the ability to resist this slightly older beauty. Was it Michel's scent or was it her focus? She'd penetrated Barb in a public space without her resistance. Barb's thong was soaked and there was a bead of her juice slowly gliding down her thigh. She knew the arousal was apparent on her face.

Michel reached for her purse, left some money, stood and helped Barb up. She was a bit wobbly due to the interlude and they passed the barkeep.

"Don't you want that wine ladies?" They smiled but left and headed to the waiting limousine.

Liz had a plan when she'd press to keep the Montreal hotel and flights. As a couple they had been to several sex clubs in DC but the ones in Quebec' were on a different level. She had researched two near to the St. James. Both were wide open meaning all type of people and fetishes would be on hand. She had Julie select their attire for the weekend and therefore Julie was game. The two sexy lovers were on an adventure in a foreign city with no responsibilities. Though Barb was a dear friend she did interfere with the girl's monthly sex charged escapades while she was living with them. A night of great sex would do them a wonder of good.

The club's party scene didn't get underway until late evening and typically closed near dawn. The two women returned to the hotel after a quick dinner. To further invoke mystery they dressed in their selected lingerie and put on their simple wrap dresses. Liz suggested they wear the delicate black lace masks she'd found on their afternoon shopping walk.

The revealing outfits caused some stir on the local streets, but the neighborhood was home to at least the two sex clubs so the crowd was accustom to the occasional troupe of mavericks. They arrive with another small group, which enhanced their anonymity, and they were quickly befriended, masks, long legs and sexy smiles.

Once inside they moved about holding hands to imply a union. They're past visits to similar spaces were better when there was no ambiguity that they came as a pair. They were parading the club in only their lingerie; sheer dresses without brasseries. Each was dressed a little differently yet both wore black, except for nude high fashion hose. Julie had on a pair of Christian Louboutin 130mm black heels and her hose had a triple band welt with a keyhole at the rear seam. Liz wore full fashion hose with a silky soft lace welt held by a eight strap suspender.

After twenty minutes they were sure their walk was complete. Any interested parties would soon approach them. They didn't try to guess who or what might happen. They allowed for only a special encounter.

The first was an older couple that just didn't bring their blood pressure up at all. They were polite but clear. Minutes later a second couple approached and the four spoke for a moment but the woman was too submissive for this evening. Then a beautiful woman walked in, with a nearly naked man aside, him tugged along but without a leash. She might have witnessed their parade but no matter, she immediately walked toward them and spoke.

"Hello, I'm Donna and this beauty is Douglas. We'd like to take you home for the night. It's our common practice so you can see the manager Richard if you need some kind of assurance. We hope we'll all have a grand time. My home is minutes away aside the Parc."

They both looked to each other, nodded assent and followed hand in hand back to the entrance. For this evening Liz and Julie would be this dome's subs.

Donna had beautiful skin and bright hazel eyes, dark brown hair just passed her shoulders. Her large breasts barely held within the long black sequin gown she wore, opening with a slit to her upper thigh where Julie observed her dark hose with a welt of silver. Julie assumed Donna to be about 45 years old and a bit taller then her 173cm.

Douglas had retrieved the women's outerwear and the manager Richard was standing near. He tipped his chin to them, while Donna climbed into her black German sedan. In the car they exchanged names and vitals, but also some cooled champagne. Good to Donna's word in five minutes the vehicle stopped and they entered an older stone house built into the side of the west slope of the Parc. There was a small cab elevator and the three women use it to arrive at the Living Room some three levels above. Douglas was there at nearly the same time having used the stairs.

Margrette stood over me when I opened my eyes the next morning. Florence was gone. I was a sticky mess and was still wearing the red lingerie from last night. I wanted to remain in the bed, and Margrette seemed to be patient with me. I did need a break, but after 30 minutes I slowly did rise and begin my toilette. She watched me and started to arrange an outfit.

"You're to continue your catwalk exercised, then later we'll focus on social settings. Please get on the scale here."

I was now naked, my clit nearly invisible.

"Oh Anna, you've reached 60kg. Mastress will be so pleased. Here, put on your bra and panty, and these stay-ups. I'd like you wear this white hoop neck blouse and black and red pleated tartan skirt. Now slip on the Mary Jane heels. Let's sit here for a simple breakfast then we'll get started."

"But Margrette, this school outfit doesn't seem right. We were to " She cut me off.

"Manners young lady. Before we eat Annabelle lean here so that I can place my plug. Your cunny is still a little too tight and you need a little convincing."

She slipped her lubed thumb in just a moment before pushing in her nearly 2" wide jeweled plug.

I whined a little really without reason. I simply wanted her to play with me. "Please Margrette, be gentle."

After the small meal she produced a wide rhinestone choker with an attached leash. She placed it about my narrow neck and led me to the hall.

"We are to move in unison Annabelle, hence the leash. Try to keep with me, about half a meter apart please. Your best strut is what I want to see."

I looked directly at her, down her torso, and saw the clear bulge beneath her skirt. She was planning to get me to fail at this task so I worked hard to keep just so. After 20 minutes of the exercise I slipped slightly and the leash became taut.

"I told you to take care young lady." She scolded me.

"One more failure and I'll have you punished is that clear? We will practice rising up the stairway now."

"Yes my Lady," I quietly said.

This was the first real harshness I been exposed to since becoming alert at the Estate several weeks ago. I had become accomplished walking in heels, even pairs as high as 130mm, but I hadn't used a stairway. The Mary Jane's were the easiest to wear but the leash would make this task difficult. During the third descent it happen, a slight misstep near the bottom cause me to fall slightly toward her. Margrette pulled me up while she fell against the banister. Neither of us was hurt.

"STOP now! Come off the stair and follow me."

We entered a small room new to me with a small daybed and a cupboard in the corner just beneath a high window.

Turning to me she said, "You could have been badly hurt." as she rubbed my shoulders.

The feel of her hands was nice but not necessary. Then with firm pressure she pushed me to my knees, she leaning against the wall.

"This will be more fun my dear, open your mouth, take this smooth meaty cock."

I found I wanted this more than I can explain. The harnessed penis was black in color, and my lips felt the raised veils along its length. I could only take a small portion into my mouth, as it was quite thick.

She stopped me, pulling me upward, and kissed my mouth while pulling my blouse open, and my breasts loose. Her cock brushed against my partially exposed tummy.

"More young lady, suck me some more," she said while pulling my hair gently with one hand. I returned to one knee and the fat cock back in my mouth.

Margrette then spun me around pulling me up and leaned me over the daybed pushed the thong panel over my cheek and removed the large plug. Then she licked my opening. She didn't paused but quickly entered my un-lubed anus. The saliva coating had done enough for she entered me with one push. The head of her cock moving up within my body brought an increase of my heart. My lust was surprising. We fuck each other like this for several moments, once she slipped out and I had to reinsert the member.

She smacked my bum playfully while holding my skirt, and then Margrette rotated to sit on the bed, her cock still deep within me. She was fucking me reverse cowgirl. More correctly I was fucking us. Her hand came around and though I was still tucked she patted my mound as we continued. In this position our passion seemed to rise quickly and her panting reached a peak as she climaxed, still within me and I released too.

"That's what happens to my bad girl when she fails to follow instructions. Down on your knees young lady. Clean my cock of your juice. We'll leave your soaked panty until later."

I licked the fat shaft and head while also rimming her vagina. "That's a good girl but back to work. Up the stair you go."

Sometime later I heard a woman walking toward us in high heels. It was Catherine coming down the hall with a small lunch. We sat on a wood bench while Margrette shared the day's events, not sparing the sex, nor the fall. Rine got down and checked my foot, then went off to the suite.

We heard another girl further down the hall but she was not known to me.

Margrette simply smiled. "That one has nearly completed her preparations. You'll meet her soon."

Catherine returned with a pair of 150mm club heels with an ankle straps and a medium platform. "Your foot isn't hurt therefore we'll try a new pair. These will affect your movement and raise that tush. Walking in super high heels will challenge our lady. The sole of the platform tends to not bend which requires a different walking style. I'll put mine on as well to demonstrate the difference."

It was the first time I seen any of the girls wearing any true high heels. They commonly wore medium chucky heels. Only 80 to 90mm. Catherine's 175cm height together with her very tall heels brought her almost to my eye level. She held my arm while Margrette reattached the leash and handed it to her. She wasn't dressed as I but still she attracted my attention. With a slow step she started our parade. The sound of heels resonated about the hall. The platform did require a change to my step and therefore my posture.

Late that night Catherine visited me as I slept. She stirred me, "Madeleine you must be prepared now. Ms. Rachel has demand that you be prepared. Get up and quickly use the toilette."

I returned in a moment. "Why at this hour are you making me so anxious?"

"Please just focus and get dressed in these." She handed me a pair of black silk stockings and a suspender, a special thong panty, and heels.

"And this negligee, oh you've not tucked correctly with that thong. Let me brush your hair,"

My hair was always their concern. They spent hours keeping my long blonde hair beautiful. I still can't imagine it. Then she moved me to the makeup desk and focused on my face, the deep tones made me look sexy and wanton.

She quietly reviewed her work then said, "Come sit in the hall."

We moved from my suite into the darken hall. "Here Anna, please sit on the chair."

It was quite dark as she settled me with my face toward the backrest of the chair.

"No Anna, you bum here."

She strapped my ankles to the chair's legs loosely. "Let me move the pad at your bottom."

I was restrained from moving from the seat. She reviewed the cuffs on my wrists, my arms partially crossed.

"Miss Catherine why can't I sleep?"

She was satisfied, "Quiet or I'll have to gag you."

Finally she placed a black cloth over my eyes. The chair's pad slightly lifted my bottom off the chair's seat.

"Stay very still and speak to no one, please Annabelle."

Due to the cloth over my eyes the sound of Catherine's heels as she left the hall was how I knew I was alone.

I sat for some time and due to the cuffs it was difficult to be comfortable but with the cloth in place my mind became blank and I slept.

I didn't hear anyone approach me but I felt a subtle brush on my stocking clad right leg. A soft tongue touched the fabric covering my opening. I was now awake but remained very still. The mouth was very moist and insistent. Someone's hands moved the thong aside exposing my hole. A moist finger entered me, then a second. After a brief moment the fingers were replaced by the head of a large semi-erect penis.

12
  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • A Visit to the North Ch. 05

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

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 20 milliseconds