Sherrie's Dollhouse Ch. 02

On our fifth "date," we met at Sherrie's again (we never went to my place, which paled compared to hers). She greeted me at the door not in her usual casual attire, but in a rather attractive and old-fashioned 1880s floor-length dress of a slightly wrinkled and white cotton fabric. I immediately assumed that her waist had been gathered in with a corset, and her breasts now looked rather more firm above her tight midriff. Above her bosom, a semi-transparent and lacy bodice closely surrounded her neck. The dress had pretty, puffy sleeves.

She had re-arranged her long hair, too. Instead of hanging loose or being braided, now it was now skillfully arranged high up on her head. All in all, she'd captured the times of over a century ago.

"Well," I said, expressing surprise, "what do we have here? Jane Austen?"

"I'm a cross between her and George Sand," Sherrie cheerily replied. "Well, what do you think?" She twirled around merrily.

"It really takes me back in time," I said. "I'll have to admit that even though so much of you is covered, the total effect is rather sexy."

"Sexy? I don't know. It just feels so right. Maybe I had a past life in the 1880s."

I laughed a little.

"No, I'm serious...... Oh, by the way, I think I'll take you up on your offer to photograph my family, Derry. Do you have your camera?"

"I always carry it; feel naked without it."

"That would explain what I found out about you. I googled you... and learned that you are a highly respected and published wildlife photographer. Why didn't you tell me?"

"I don't want to live on past accomplishments."

"Well, I wish you would've told me. But I can understand your desire to be low-key."

"Great."

"Now I can admit that my birth name was not Sherrie Flowers. I changed it from Nancy Lubowsky."

"I'm not at all surprised."

"So, could we take a couple photos today?"

"Love to."

She soon made it clear that she wanted me in the photos too. Amazingly, she'd visited a costume shop and had rented a complete man's outfit for me -- to place me, too, in her late 1800s era. I was a little reluctant at first to change into this clothing (my reserve, again, and not used to being in my own photos) but decided to be more of a fun guy and go along. So, she showed me to her bedroom where the clothing was all laid out on a bed. It all began by putting on a starched white shirt with plain tie and vest, followed by a dark-brown suit with overly long jacket. The effect was topped off with a bowler hat. I confess that when I looked in the mirror, I thoroughly enjoyed the transformation.

When I returned to her living room, she clapped her hands merrily. "Oh Derry, we've really done it, haven't we?" With that, she took the liberty of applying a false, bushy mustache above my lips.

I strongly felt I had time-transported back to the 1880s. What a turn my life was taking.

I set the camera up for time-delay exposures, which allowed me time to quickly walk over and sit next to the pretty adult-doll women as the camera clicked. They wore dresses and had hair styles similar to Sherrie's. Next to us, the children were wearing spotlessly white pinafores. After this, we took some closer-in shots with just Sherrie, two of the doll children, and me. I suppose I was playing their father or grandfather.

When I showed Sherrie the results of the digital photos, she was more than pleased, and hoped we could repeat the shoots on other days.

As per our routine, we moved over to her love sofa, and watched a Disney kid's movie -- not much to my liking -- but then I wanted so badly to make out with her.

I began to pull off my mustache, but she said, no -- that would ruin the ambiance. As we sat there, she ran her hand inside my suit jacket, saying she loved its feel. Then she began nuzzling my faux mustache with her nose, and lightly kissed me through it. At the same time, her hand had migrated to my inner thigh -- briefly. I was taken back to the time I first made out with a woman at a beer bar back in my student days (I was a late bloomer).

There on the sofa, overcome with 54-year-old lust, I once again placed my hand on the upper portion of her breast which emerged from the top of what I now knew to be her boned corset. This time, she mmmm-ed a little, and let my paw rest there. I bent over and kissed her with more urgency, through the mustache. My prick was quite hard.

Sherrie then unbuttoned my vest and shirt and reached in to gently play with my nipple. I too mmmm-ed a little. She soon made it clear that this was as far as she wanted to go.

So, I had reached second base.

As usual, she soon made it clear my visit had ended, and after I changed back to 21st century Derry, I left. Upon reaching my own place, I could hardly wait to beat off.

This interlude was my reward for joining her fantasy family! I was taken with Sherrie's directness. She seemed to know exactly how to orchestrate things and to get what she wanted. I had left my former calm, measured existence, and was walking into a sort of paradise that offered more and more, as long as I played along with her fantasies and was patient.

Next time we met, we again walked the path around the lake, with child Debbie in her stroller, but this time we were daringly attired in the same 1800s attire we'd worn previously. An added touch was her dainty parasol. We choose a time and day when there weren't likely to be other walkers on the path, so as not to arouse unwanted curiosity. I took some more timed exposures. It was wonderful fun.

Behind a tree, we managed an 1800s kiss, and I briefly placed my leg more or less between hers, under that voluminous dress. She let that happen briefly. Unfortunately, there was to be no amorous love-sofa action that day.

After a month-long hiatus (I had taken a trip to Europe to visit some old friends), I gave Sherrie a call.

"Derry, we missed you so much. We really wish you hadn't been away for so long. You were neglecting us in the Glen."

"I missed you all too. I actually spent some of my time online looking at clothing styles from the 1880s and the 90s, and even read a Henry James novel about the manners of those times. So interesting!"

"What did you think of it?"

"James writes so densely, and with so much detail. What was best was learning about the way men and women engaged each other then."

"Well, Derry, this is so remarkable, the lengths you've gone to. And now that you've looked into it more, what do you think about fashions back then?"

"Well, of course, women, even though they all wore long dresses, still could pick from many different styles. Their big hats, wonderful hairdos, curious tight little shoes, and so on. Men's clothing was so predictable and stodgy.

"And there's something else -- I was looking through my library -- and found an old scrapbook I inherited from my parents. It is, remarkably, circa 1880s, and part of it has cut-out lithographs of beautiful women in head-and-shoulder and full-length portraits. What a discovery!"

"Oh, bring that next time you come over, Derry. I hope you will come over soon."

"Saturday?"

"Yes, come to the Glen Saturday morning."

When I arrived, we pored through the scrapbook. She absolutely loved it. Back in her casual attire, she seemed more animated than usual, and even poured some of the rose wine I'd brought during my first visit. She sipped a little while I polished off two full glasses. I was getting inebriated.

In the next room, her doll family patiently awaited our presence. So we walked in and enjoyed the wine and some muffins with them, as corny as that sounds.

Sherrie to her dolls: "We want to welcome Derry back, don't we? We missed him, especially since he so wonderfully joined us in his wonderful suit and hat."

I smiled and sipped more wine.

For the first time, she provided the names of the two adult women dolls (Emma and Alice) and addressed them: "Didn't Derry look so fine in his suit? Now, I do hope that Derry will try on a new outfit that would be even more fun -- Derry could dress up as, say -- Anna! -- to join us. Alice, would you like to have a new woman-friend? Oh, wonderful!"

"Derry -- they so want you to be an Anna for them. Could you do that for us?"

I found this turn of events to be a world-changer of extreme proportions. Other than in a childhood play in a back yard orchestrated by my older sisters one time, I had never dressed as a girl or woman. The desire never entered my mind, and even though I was greatly excited by women in lingerie or sexy clothing, I could not -- I repeat, could not -- picture myself dressed as Sherrie had been dressed.

I was silent and looked away, feeling like seven pairs of eyes were bearing down on me. Imagine that.

"It would be so much fun," urged Sherrie, "to let the child in you come out. I saw how much you loved your appearance as an 1880s man; now think of how much better you'd look as an Anna!"

"Going too far," I managed. "If anyone found out I'd be an object of ridicule."

"You know we're very private here. Any photos we took would stay with you."

"So how far do you want to take this?"

"To make you look as much like a Victorian woman as possible."

"Corset and wig and makeup and all?"

"Oh, yes. We want you to look into a mirror and say, 'I feel like Anna.'"

"I'm sorry Sherrie, it just doesn't work for me. It's taking the fantasy too far."

"Well, then, Derry, I really hate to say it, but you are choosing to end our relationship, because for me, this is necessary if you're to be part of our family. We very much want you to grow into a more versatile person. Actually, I'm sure that in the end, you would find that you enjoyed it."

"You have a gift for persuasion."

Sherrie: "And, dear, there's the erotic attraction between us -- I can see taking our fun to the next level, and to the next level after that, just like the characters in a steamy period novel."

"You have the gift of persuasion times two. Let me think this over a little more."

I returned home, with my mind racing. In my mind's eye I saw myself in the vintage man's suit, and then in Sherrie's plumage. Would this be a one-time part to play, or would she insist on this all the time? Would she hold back on full-bore sex until I became her permanent Anna doll? I really did want to bed her and go all the way. If we did do that, would I do it as Anna or Derry?

Ultimately, my lust won out. I hoped I wouldn't look and act silly. A small part of me was afraid I might get to like wearing the fascinating attire of women, and my equilibrium as a man-- and as an intrepid wildlife photographer -- would be disturbed.

Take chances; go with the flow, I told myself.

When I told Sherrie, she was ecstatic. "We're about the same height and size, so you can wear my things," she promised. "This will be such a big moment in Briarwood Glen. Emma and Alice and the girls will be so, so happy."

The date was set -- our date. Two weeks away. I absolutely could not take my mind off this. My thoughts were running in so many directions.