A Familiar's Fate Ch. 11

Chapter 11

Sunday started much the same way. I cooked breakfast, and cleaned up. We did some work, but mostly just relaxed.

She renewed her request to take me out shopping. Despite my new found desire to expand my wardrobe, I remained nervous about being out in public wearing a dress. Initially, I successfully distracted her by licking her to orgasm.

Yet, once she was fully sated, her attention refocused.

She understood my anxiety about being in public, but remained insistent. "You got away with it last week, but I want to show off my pretty sissy."

I still bristled at the word, despite its obvious truth.

"And you do need more clothes, a purse, some shoes, and to get your nails done."

"My nails?" Part of the way she kept me off balance was her manner of constantly presenting new challenges

"Sure. They're not very long. But we could get our nails done together, maybe even get matching colours. What do you think?"

I shook my head, not even sure why I was objecting. It was just another step in my feminization.

She managed to coax me out with some light hearted banter. "Come on Christine, it's time for the girls to do some shopping!"

I was still reluctant to go out, but I relented once more. Even I was starting to wonder why I bothered resisting her at this point. Yet, this was reality, not like our fantasy roleplaying at her home.

I froze in the car when we arrived at the mall. However, another stern look from Karen, and I was moving.

To Karen's delight, I had no trouble walking. I was becoming more and more confident wearing heels. The sensation of wearing a dress, and nylon-covered legs rubbing together with every stride excited me. Fortunately, my penis was firmly enclosed by the pantyhose. The heels gave my legs a nice arch, and my hips swayed with my walk.

Karen was loving it. By contrast, she was wearing slacks, a buttoned-shirt with collar, and a pair of flats. She is always beautiful. Yet in my pink dress and heels, I was the one who was more feminine.

The mall had a steady stream of people coming and going in all directions. It was at once unnerving and comforting. There was so many people that I expected to be called out at any moment. The freak, the sissy, the guy wearing a dress. Yet there were so many people that perhaps we would disappear into the crowd. Just two young ladies shopping on a Sunday afternoon.

I was not prepared for the third scenario. Furtive glances from men.

Karen gave a knowing smile, almost laughing at my nervous look.

A handsome man, slightly older than us, and dressed sharply in a casual suit, was looking at me from the other end of the first shop we stopped at.

I was afraid I had been outed. Yet Karen clearly saw it differently.

"It looks like someone is appreciating you my pretty one. Would you like to go chat him up?" Karen teased me.

I looked back at her in shock. "What?" It was hard to keep my composure. I wanted to disappear... to be anywhere but here.

She laughed. "What?" she said with a mocking tone. "Don't you think he's handsome?"

He was undeniably handsome.

"I suppose, but why is he looking at me?"

Karen leaned over and whispered in my ear. "Because you are pretty."

I blushed. Standing next to a gorgeous woman like Karen, why would anyone think I'm pretty? Why would men look at me?

Suddenly Mr. Invisible, who had longed for women to notice him, was getting attention. Yet not the attention I wanted.

I prompted Karen for us to move on. She paused, wanting to find some items. Yet she mercifully relented, only stopping to purchase 3 sets of blouses and slacks.

The next stop started a different form of awkwardness. A lingerie shop. All those pretty things. Things I would like to see Karen wearing.

Yet it was clear that Karen had other ideas. She immediately began pointing out a variety of garments. Panties, negligee, bras, camisoles. All soft, seductive and pretty.

"This would look pretty on you... Or how about this one?"

"Karen, I can't afford these." It was a lame excuse, but it was all I could think to say.

"Oh, don't worry about that. This is all my treat. I want to take care of my pretty girl." She hugged me, and laughed.

I could only give a meek smile in return. Her pretty girl?

I relented, allowing her to pick-up some panties and chemises. All bright colours, soft, and delicate. They were cute. Despite myself, my little penis twitched within its panty and nylon encasement.

Karen looked at the matching bras. This really put a lump in my throat. I could easily disguise wearing panties and camisoles under my usual shirts and pants. Yet bras, they were another story.

She had her heart set on a pink bra with a pretty lace trim. Just the feel of it in my hand excited me. But I couldn't ever wear this.

Karen wasn't taking No for an answer. She picked up this bra, and three more pretty bras. Each matching the panties she had already selected.

With her tools of feminization in hand, she started for the counter.

"Wait." I called out, with as feminine a voice as I could muster.

She paused for a moment, suspecting I was just going to argue further.

I selected the same bras, except a different size, and handed them to her.

There was a bemused look on her face as I took the first set of bras from her and placed them back onto the shelf.

How did I know my bra size? Once again, her sissy had surprised her.

She didn't say a word as she brought the bras, panties, camisoles, and 1 negligee to the counter.

I was afraid the sales clerk would notice that I was not a woman, as we now stood directly in front of her. Yet once again my fear was for nothing.

As we exited the store, Karen continued to look at me with an amused smile. And once we were out of the crowded area, she remarked, "I gather you borrowed more than your mother's shoes."

I blushed and looked down sheepishly.

I was more than ready to leave at this point. Yet once again, Karen had other ideas.

We started looking at dresses, skirts and blouses. At least this would give me some options for dresses and skirts at her home. This reinforced the confidence that it was now my home as well. Surely, she didn't intend to make me wear a dress in public again.

Karen was clearly enjoying every minute of this. I think my humiliation made her happy. Certainly my emasculation did.

Yet I have to admit, it was rather fun to see all the beautiful fabrics, and try out some of the dresses. It was exciting and fun. Shopping for men's clothes was always a chore. Oh, I need a new pair of pants, let's see what they have. These will fit. Next.

Women's clothing has colour and style. There were options. They have character. They're fun.

I could easily see why women enjoyed shopping. And now it was my turn.

Karen was happy that I was finally getting into the spirit of things. I was no longer worrying if the sales clerks recognized that I was a man in a dress. And I no longer felt like hiding when a man looked at me.

In the end, 2 dresses, 2 skirts and 3 blouses were purchased. Overall, it was quite the haul of clothing purchased.

I asked Karen as we carried the bags out to the car, when I may be able to try out the new clothes at her home.

She grinned. "They are all your clothes sweetie. I hope you will wear them as often as possible. Especially the under garments."

I was stunned. Where was I going to wear women's clothing? I didn't want to be wearing a dress in public again. And I certainly can't wear anything, not even the blouses, at work.

Yet before I could raise any objection, Karen had changed focus, looking at her watch. "Oh my, look at the time. It's nearly 4:30. We need to get home. I have a video conference, I need to get ready for. Perhaps we can grab some dinner on the way home."

I simply nodded.

"Damn, we didn't have enough time to get our nails done." She was already scheming to feminize me further, but I would worry about that later.

* * *

Back home, after her call she sat in her straight back chair. She pointed to the floor in front of her. That's all she needed to do. She placed her hand on the back of my head, redirecting me back between her legs.

This was what my mouth was meant for.

That evening, I begged her to touch me. It had been days since I had cum, and I was aching. I had licked and fingered her to multiple orgasms. Surely, I deserved a reward.

Yet Karen simply dismissed it. She wasn't in the mood and we had a busy day tomorrow. Whatever her reason was only a token for her real reason. She liked having me on the edge, desperate for her attention.