Sherrie's Dollhouse Ch. 03

As I drove over to Sherrie's place, I was worried, worried I'd become an 1880s version of a drag queen. A transvestite, a crossdresser. She had probably hidden cameras somewhere and would blackmail me with compromising photos. I feared I was becoming her slave, like when I gave in to her insistence that I closely shave my arms, chest, shoulders and face. She had me by the balls.

On the other hand, there was sexual excitement building in me fed by the unknown, danger, her kissy lips, and her long hair. And maybe eventually, her pretty cunt.

Sherrie welcomed me, in a new long dress with more lace, in an off-white color. I handed her a bottle of Riesling.

"Oh, thank you so much, dear," she said, hugging me and pecking me on the cheek. I had an instant erection. "We have so been looking forward to your visit. I've been telling the children they'll meet Anna for the first time!"

I blushed a little; she noticed. "Derry, let's open this lovely wine and have a little before I help you dress."

"Sure, let's."

Again, the wine barely touched her lips while I drank a little too much, and was definitely feeling more loving and relaxed. In Sherrie's company, and around her "family," I was again feeling immersed in all things Victorian.

Soon, she led me into her bedroom where a variety of garments were laid out on the bed. Against my will, I had another erection. I didn't want it to show, but I think Sherrie noticed everything.

"For starters," she announced brightly, "put on these nice drawers, which you may love because they are so nice and soft, and then I'll come in to cinch your waist, OK?"

I grunted "yes," at which she closed the door, leaving me with my erection as I undressed. The Victorian drawers were long and loose, with dainty lace at the bottom. Putting them on, my dick made a strong dent in them and produced a moist spot.

I tried to keep Sherrie at bay until my erection subsided, but that took too long, and she came in uninvited.

"I'll try not to notice your little excitement there, Anna," she said, herself somewhat embarrassed.

She then introduced me to the next cotton garment, which she called a chemise. White, with rather sexy lace embroidery around its top, it pulled on nicely over my shoulders and came down to my waist. It left exposed most of my upper chest. Tell the truth, I liked wearing it. It made me feel just a little feminine, something I'd been missing in my life.

Sherrie stepped back to judge the effect. "My, my, Anna, these fit you rather well, don't they?.....

"And now, the crème de la crème." She fetched what appeared to be a corset from the bed. I'd been eyeing it with a sense of wonder. It was a cream color, with much boning and some satin panels. As she held it up against me, I realized that back in those times -- the gay 90s -- corsets didn't have cups for women's breasts. They rather pushed up one's breasts and topped off just above one's nipples.

She had me step into it. I felt rather awkward doing so, and nearly fell over until I grabbed a chair. I could see the concoction was meant to be laced up, and that Sherrie would do the lacing.

I felt like a wedding cake being elaborately iced.

We positioned the garment, and Sherrie began tightening the lacing in back. Down below, my erection was increasingly protruding against my drawers. Beginning at the corset's top, she authoritatively began pulling the laces, making its top push up my hardly-there male breasts.

"This corset has some built-in bust enhancers," she informed me, as she continued her tight lacing. I was astounded by how far she drew in my waist. I was so bound and confined that my breathing became shallow. My prick rose even higher yet.

As I looked at myself in her full-length mirror, my ample fanny now contrasted nicely with my very-narrow waist.

"There," she announced as she tied off the laces in back and I stiffly sat down on her bed to pull on some long silken stockings. "Anna, Anna, you're on your way! What do you think?"

"I'm becoming quite the doll," I quipped.

Next Sherrie had me step into a princess-like petticoat that blossomed outward. After that, I slipped into one of Sherrie's dresses, with a closely fitted midriff. This shiny creation was a light green, with an embroidered bodice open to the bosom in the middle, with sleeves widening as they extended. At the dress's hem, there was more embroidery, rather like a peasant style.

To add to all of this, Sherrie provided some slender black cotton gloves.

Now it was time for her to playfully attend to my head. She worked rather quickly in making up my face and modifying my eyebrows in an 1890's style.

Finally, Sherrie opened a gayly decorated box and withdrew a wig -- its style very closely matching the way she had her own hair: uplifted, with some cute swirls. As she carefully fit it onto my head, and smoothed out a few wisps of faux hair, she whistled.

"Oh my gosh, Anna, look what we've accomplished. Are you ready to see yourself?"

I stood up and looked in her mirror. I really could not believe my eyes. What a job she had done! In my reflection stood a real, live woman. I... had... become... Anna. Anna of Briarwood Glen. My psyche excitedly absorbed this new person.

I dimly realized Sherrie was writing a book in real life and I was one of the characters she'd created.

I hugged her. Her boobs were now against my boobs. "I want to hear what your family says about me," I said. "What will they say?"

We sat down and had tea with Emma and Alice while the four children looked on.

"Emma and Alice, you now have a new friend visiting -- Anna. Doesn't she look so pretty and proper? What do you think of her dress and hair?"

A pause and then, "Anna, Emma says she'd love to have you as a friend. Alice too."

I slipped my hand over Emma's, and said, "Why, thank you."

We sipped our tea. With my horniness, even the adult dolls looked rather sexy with their just-so bosoms, painted lips, and delicate hands.

After a half-hour of this fantasy play, Sherrie and I retreated to our old haunt, the sofa, to watch a Sherlock Holmes film on TV with the proper ladies in 1890s dresses. While we cuddled, we decided which of the ladies' outfits we liked the best.

Soon we were kissing, more fully than ever before. My transformation to woman seemed to excite Sherrie. Soon she was feeling up my bust (what there was of one) and my thighs. I responded equally. We were soon wrapping ourselves around each other like copulating snakes.

We put aside our passion long enough to go in her bedroom and quickly pull off our petticoats before jumping into bed. I reached under her dress and slid my hand up her thigh teasingly. She curtailed my move before it reached her sweet spot, but that didn't stop her from doing the same thing to me. While one of her hands crept under my bodice to play with my nipple, the other hand found my thick and throbbing cock deep under my drawers. It was so wet with precum that she didn't need any lube to hand-stroke it.

"You have such a nice clit, Anna," she whispered in my ear. "Does this make you feel extra nice?"

I came all too quickly. All I could do was exclaim "Oh god... god... god," as I spurted into her hand and into my drawers.

I lay back in all my finery with my eyes closed, in my very tight corset, with the wig still on. But Sherrie soon found a towel, lifted my dress and pulled down my drawers so she would wipe up my cum, obviously fearing I stained the dress (which I didn't do).

I smiled weakly while she was doing all this, and finally said, "My dear, this was so much fun, and thank you truly, but I hoped we'd do the act, you know. Is that something you'd like to do?"

"Let's just take things slowly, Anna," she said seriously, now distanced a bit from her fantasy world. Sex can be too farm-animal-like sometimes, and I don't want to go to THAT place. I like sex to be polite and gentle and, well, slow. I like to play."

"Next time I'd like to reward your clit."

"Maybe, if we can keep relating as two ladies."

I was coming to discover that Sherrie had a lot of money to spend. Besides her Mercedes sedan, every time I came over, when she was in Victorian mode, she had a new dress on.

Along those lines, she eventually showed me a small closet and small chest of drawers she was surprisingly devoting exclusively to me as Anna. As an indication of her confidence in me, she showed me five custom-made dresses she'd acquired for me -- plus two corsets, four pairs of vintage shoes and boots, three wigs, and an assortment of drawers and chemises. The largess continued, with jewelry, perfume, a dainty makeup kit, and much more. Beyond that, she had even procured one set of contemporary attire, including a skirt, slim sweater, plus a wig, several bras, panties and the like. "This is for the occasional time when we get tired of our Victorian game," she allowed.

"It's fun messing around with you as another woman," I said. "But a year ago, if anyone'd told me I'd be into this, I'd've told them they were crazy."

"Our meeting on that path was meant to be, Anna," said Sherrie. "I had dreamed of a relationship like this. A woman with a little extra." She actually blushed a little.

I knew that at least for the time being, living with her and her family would be too much reality for her to handle. She depended upon her fantasy world to keep her intact.

The same day she showed me all of this finery, I easily became Anna again. This time, and succeeding times, I was able to do more of my own makeup. And one of the corsets had front fasteners and didn't require her lacing me up every time. I was feeling more and more comfortable being Anna. I could relax and have fun.

The next time I came over, with little idea of what Sherrie wanted to do, she was out of Victorian mode and into casual dress again. That is, not in a dress but in loose Levi's and a T-shirt emblazoned with "I can't adult today -- please don't make me adult."

I laughed. "Ok, Sherrie, today you are, say, 10 years old."

"That would suit me."

Which I thought was a brilliant pun, knowing how much into clothing she was.

I wondered just what she had planned for the day, knowing how much she liked to orchestrate things. I didn't have to wait long. She had me pick out a dress, so I choose a slender white creation, nearly transparent because it had so much lace and the material was so thin. She still insisted on a corset, but there were no petticoats this time. She seemed in a hurry -- so much so that we didn't do makeup.

Then it was time to set the scene. Sitting by herself in the living room was Emma, the three-fourths-size adult doll, with long, flowing hair down to her waist, and an off-white long dress, also without petticoats.

"Please indulge me, Anna; please, please do this for me. Go on a date with Emma, and become intimate. I want to see you become intimate with her."

This was taking things to an all-new plane. I gathered she wanted me to fuck the doll like you see some guys fucking fake blow-up women. Kind of gross.

"You actually want me to go all the way with her? Now how the heck would I do that?"

Sherrie blushed, and looked away for a moment. "She is especially outfitted with a vagina, Anna. If you do this I will explain everything later."

"Things are getting just a little creepy for me, dear. I suppose you will video this and I'll find myself on social media, or you showing your friends."

"You forget. I don't have any friends. The only social media I visit is a couple Victorian groups online. I'll put my phone in the other room if it makes you more comfortable."

"And of course you want to watch?"

"Of course." She laughed a little.

"And how would Emma feel about this?"

"We talked it over. She likes you and wants you to do her."

"Is she a virgin?" I thought I'd milk this for all it was worth.

"Oh no, she's experienced. She enjoys men."

I thought things over. "I will do this if you and I can go all the way soon."

"I promise."