Sherrie's Dollhouse Ch. 04

I really did manage to do it. Screwy, but I did it. And without ever having fucked a blow-up doll before.

I took "Emma" into the bedroom and lay her down. Sherrie came in, handed me some lube, seated herself in a chair, and watched.

I lay next to the doll and looked intently into her glassy, brown eyes. I remembered that I must proceed quite slowly, because I didn't want Sherrie to think I was a slam-bang, quick-fuck kind of guy. Laying alongside the large doll, I pulled her to me and ever so gently kissed her tiny painted lips. Then I kissed her hands and ran my fingers through her luxuriously long hair, which must've been human hair. I kissed her neck and her bosom.

Then I ran my hand lightly over "Emma's" barely-there bosom, gently massaging her breasts. I kissed her again, with a long lingering kiss. I kissed her ears. Then I finally pulled up her long Victorian dress and ran my hand up her thighs.

I wondered if Sherrie was getting off seeing two women make love.

By feel, I found evidence of a small doll cunt down there, and with an opening!

As I began to feel rather horny, my penis came alive. I pushed the dress up further, bringing Emma's cunt into full view, and explored it with a friendly finger. No clit, but there definitely was a vagina.

I could see Sherrie was entirely engrossed in the scene.

I fingered some lube into the "vagina," and after pulling up my dress and pulling my drawers off, I lubed myself. Now positioned over Emma, I played my cock's head around her cunt a little before ever so slowly pushing in. The passageway fit my cock nicely.

Sherrie walked across the room to get a better view.

I could've madly fucked away for a minute and reached orgasm quickly, but held back and thrust gently and slowly. My corset's tightness felt highly erotic, and wisps of hair from my wig fell across my face.

Gradually, I increased the tempo of my thrusts, but never went into a frenzy. After a few minutes, Emma received my sperm, and I had a great orgasm. But I didn't scream or yell, as I have been prone to do in the past. I just sighed deeply,

After a spell, I gently withdrew, and wiped myself with the towel Sherrie soon provided. I wasn't going to worry about my jizz in Emma; Sherrie would have to take care of that.

As I wiped myself most carefully, Sherrie stood over me, smiling broadly. "Well, see, that was doable, wasn't it? You really acquitted yourself admirably, Anna. I mean, it really did look like you were both women enjoying their company. At least that's what I wanted to see. Bravo!"

She brought me a glass of wine, as a thanks, I suppose. Then she kissed my forehead.

She excused herself to the bathroom, where she remained longer than one would expect. Maybe it was just a male fantasy, but I guessed she was masturbating.

Upon emerging, her cheeks were quite rosy. She went about making some sandwiches for lunch, which we eventually enjoyed while sitting, again, on her vintage sofa.

"I think Emma quite enjoyed your amorous attentions," she said. "I think she loved your touching her love spots and entering her gently and with care."

"Emma was a good lover," I added.

"Now, Sherrie, you mentioned you wanted to explain something? I'm very curious."

"Oh, it's a long story. Are you sure you want to hear it, Anna?"

"Certainly."

She lay one denim leg over my own legs and my dress, and leaned back, wiping sandwich crumbs from her lips.

"My past, dear Anna, my distant and not-so-distant past. I grew up on a farm in the sticks. My mother died when I was four, so my dad raised my two brothers and I. He was a hard taskmaster. Of course part of that was due to not having a wife to handle the domestic duties.

"My brothers and I did a lot of outdoor work, taking care of the chickens and milking cows, and even driving the tractor sometimes to handle the field crops. Also I had to do the laundry. Dad did the cooking and I helped with the dishes. I had no feminine identity at all. I always wore boys' clothing. I never wore a dress or girls' clothing until I went to school. Even then, some girls called me Nancy Nada, because my clothing was so basic and cheap, my hair was cropped short by my dad, and I couldn't dance or take part in the social swirl."

"You must've been pretty unhappy," I offered.

"To say the least. But I did get great grades; my dad made sure of that; because my brothers didn't. I went on to college on a nice scholarship, so I bloomed a little bit. Majored in English, because I enjoyed reading so much. There, I had some, well, flirtations with boys for the first time. There were only two that went anywhere. One turned out to only want rough sex; I ended that quickly. The other one turned out to be gay. We remained friends.

"I taught at the high school level for a while. There was another teacher there, a woman who I was attracted to. I eventually told her about my feelings, and was embarrassed when she more or less mocked me, and that was that."

"And at some point you began doing kid's books."

"While I continued teaching for the money, I slowly became immersed in the Victorian world of pretty women in beautiful dresses and conservative men in vests and suits. It began to consume my fantasy life. I began with small little Victorian dolls, and gradually moved on up to my big dolls. Then I started dressing Victorian myself -- lovely, sexy dresses and corsets. I really did begin to feel that my dolls were my best friends, and you know, family, and I began to interact with them -- so childish, I know. I began writing stories about them, and dreamed up Briarwood Glen, and eventually I got to the point where I could turn them into publishable books, and leave teaching. So -- my doll friends and the books, which have made me a lot of money, have pretty much kept me from going totally looney.

"Oh, and one other thing -- you may think it odd, but I have played both female and male roles with my dolls. Usually I'm the matriarch, but once in a while I'm the father if I'm so inclined."

"Sherrie, I'm going to ask you a very personal question, which you needn't answer if you don't want to."

"OK."

"Have you ever gone all the way with a man?"

"Oh, no, I'm still a virgin."

"So, I'm so curious -- why did you want me to make it with Emma?"

It was time for Sherri to blush again. "Because I wanted to see how you made love. Emma and I are so close, I easily imagined I was her.

"..... OK, l'll admit I'm a bit fearful of men. Of men being macho not wanting the kind of gentle sex I imagine for myself."

"I can see that," I said. "But why do you feel more comfortable with me as Anna, rather than Derry? Maybe you see yourself as more relaxed with a woman now? And of course all your friends now -- your doll family -- are girls and women."

"Yes, that's it, Derry, I mean Anna. You've hit it. I like a woman with something extra."

"OK, Sherrie. Now it's my turn to admit something."

"Yes?"

"I've been surprised that I enjoy being Anna! I don't think I'd want to be a full-time Anna, but I'm finding being Anna is rather erotic, and opens up a whole new part of me I didn't know existed."

"Well, I couldn't help but notice that wearing Anna's apparel turned you on."

We both laughed.

We soon ended up lying on her bed, where we turned to each other, held each other tightly, and kissed long and longingly. Eventually, I began caressing her breasts. As before, she played with my cock under my dress. But this time she allowed my hand to travel up her thigh, to unzip her Levi's and ever so lightly begin to touch her cunt. At first touch, she shuddered a little, and whispered, "Oh Anna, dear, oh Anna, aren't we being naughty?"

While I kissed her neck, my finger circling her clit brought her to orgasm. She convulsed several times and then lay back.

And then she wept, deeply.

I wiped her tears away and didn't say anything.

Eventually, she opened up and looked my way. "I feel as though all of Springtime has moved through me. Butterflies, and tiny flowers, and meadowlarks. It's all there. Anna, wow, how could you be so nice to me?"

"No, it's me that's saying that. How could I be so lucky to have met you?"

The next time we were together, I knew we were ripe for ending her virginity. She was already dressed in the most sensual of dresses -- probably meant for a classy social gathering. It was basic black, with short sleeves and the most wonderful wide, white lace bodice. The neckline was low, displaying her bare shoulders. Her hair was even more artfully tossed than before. A velvet black choker completed the picture.

She had an entirely new dress for me. A bride might've worn it. It was white, of a quite thin and gauze-y cotton. The shoulders and bosom were covered with very lacy and intricate over-cover, which became more transparent as it approached the neck. However, the high neck itself -- closely covering my entire throat -- was embroidered. The thin, transparent sleeves fell loosely to my wrists. As the dress neared the floor with many folds, there was an extra flounce just above the hem.

Underneath, Sherrie had me skip the corset this time, to wear what she called a bralette (with modest little breast forms), plus a very lacy white pair of contemporary panties.

To go with this, a new brown wig, and the most wide and gayly decorated hat, with imitation flowers and more. Now that I had my ears pierced, she could add precious little pearl earrings.

After makeup and subtle lipstick and a little eyebrow pencil, I was feeling thoroughly "Anna" again -- sexy and pretty.

We celebrated each other by enjoying tea and scones with her family.

"Emma, did you enjoy being with Anna? Was she nice to you? Did she make you feel good?"

It was assumed that Emma answered in the affirmative.

"Anna, did you enjoy being intimate with Emma?"

"Oh, yes, very much so. She is such an attractive and sexy woman."

Sherrie: "Emma, I hope you wouldn't be jealous if Anna and I spent some time together today. We like each other and have been looking forward to today."

I looked at Emma, halfway expecting to suddenly speak up. But no, there was just that pretty face, long hair, and tiny painted lips.

"Anna, Emma says she wishes she had you all to herself, but because of our long friendship, she is willing to share."

"Thank you, Emma," I said.

Sherrie and I spent most of an hour cuddling on her sofa. I loved her perfume, and she had the most inviting lipstick. On her giant TV was another period Victorian-era drama. The sound was down really low and we weren't paying that much attention to it. With all our kissing -- lipstick to lipstick -- and petting we were both getting worked up. Her hand was lying in my lap, and my cock was rising to meet it.

"Your bed?" I asked.

We walked into her bedroom, hand in hand, hips touching.

"In this dress," I commented, "I feel like we just got married, and this is our wedding bed."

"Oh, don't be so serious, Anna. Just treat me like Emma, and we'll have lots of fun."

So we lay down, and to be perfectly honest, I proceeded just as I did with Emma. I didn't want to do anything new that might trigger Sherrie's fears.

I had looked forward for so long to actually see Sherrie's breasts and cunt. When her dress came off, I saw her small and pert breasts, with small pink nipples. I kissed them. Then off came her petticoat and drawers, and -- time for her to blush again -- there was the cutest cunt, without any pubic hair at all. Just all so pure and sexy looking.

I could've tongued her right then and there, but retained my patience, saying as I lay my hand on it, "I love your cunt, dear. It's just absolutely perfect."

"Yes, and it craves your attention."

As I did with Emma, I carefully traced its contours and edges with my finger, at which Sherrie squirmed and moaned a little.

Sherrie once more reached under my petticoat to find my dick. "Oh Anna, what a surprise to find this under your dress." She lightly grasped the erection, wet with precum. "Now what use do you suppose it could be put to?"

"I've heard it said that it's like a dowsing rod. It can be used to find hidden springs."

"Well then, do try to find those hidden springs," Sherrie chuckled.

As we assumed the missionary position, I did indeed place my rod lightly on her clit, and massaged it around a bit, making her moan once more. "Oh Anna, be a good dowser."

And so I entered her just a little, fearing I might have a hymen to tear and cause pain, but that didn't happen. Sherrie was laying back with her eyes closed with an occasional flutter.

"This is sending me to heaven," I said. "Is it good for you too?"

"Don't talk, Anna, just do what comes natural. Do your business!"

And so I did, just as with Emma. The difference was that Sherrie was reaching down to touch her clit as I entered her further. Soon I began a very slow rhythm of even thrusts, knowing that if I sped up, I'd come within seconds. Soon, her self-stimulation was bringing her to a pitch of excitement. So, I sped up just a little, then a little more, and we virtually both came at the same time.

After I withdrew and we were both lying there, she hoarsely spoke up.

"Anna, Anna, what you do to me ..... wonderful."

"We had a good time; we made good music."

"I have the feeling we could continue to have some good times together. Just follow my directions and you'll always be rewarded, I'm sure."

I laughed at her humor. And yet, I realized it was only half humor.