Sherrie's Dollhouse Ch. 05

After reaching the end zone with Sherrie, which satisfied me immensely, our relationship continued to evolve. I spent more and more time with her, and after three months, we occasionally slept the night together, me in a long, frilly Victorian nightgown. I had let my hair grow long, and eventually no longer had to wear a wig (thank god).

Now that she trusted me with sex, we indulged maybe every week or two. She was so inventive, and kept things fresh with her fantasies and ideas. Again, it was as though I was in a Victorian book she was creating. During one of our bedtime romps, she up and began kissing my erect prick, and then took its head within her sweet lips, all the time looking at me to see my reaction. I was in heaven. She ran her tongue around it.

I think she got most of her sexual ideas from watching porn on the Internet -- something she'd never admitted.

I said, once while in that heaven, "Sherrie, I'm close to cuming in your mouth. Is that something you want to experience? I don't want to shock you."

"Oh dear," she said, after pulling away, "No, I don't think so at this point. Thank you so much for warning me."

But after a month or so more, she did reach the point of enjoying receiving my load, but in her own way. Eventually, she even enjoyed my spraying her face with my milk. Kind of like having a "shower of nature's seed."

On my end, I did eventually ask if she'd like my tongue exploring her private parts (phrasing it as Victorians might). She said she'd like to try it. Again, I proceeded very slowly and delicately -- as Anna, of course. She always kept her cunt completely shaved and it was oh, so small and pure-looking. The first time, she was a bit nervous and didn't climax, but with me also playing with her breast, I knew she came close. The second time, as my tongue toyed with her tiny clit, she suddenly pushed my whole face into her pubic lips -- hard -- as she came -- in big jerks and gasps.

"Oh my, Anna, why have I waited so long in my life to experience this?"

"You were waiting for me, silly," I quipped.

The more time I spent at her place, the more womanly I felt. I began to feel that my breast forms were real tits, and I loved the idea of having real tits. I had begun speaking and moving more femininely.

I'll admit to becoming more comfortable in my Victorian dresses and underwear than I was in a man's clothing -- that is, as long as I didn't have to wear a tight corset. The corsets, therefore, only came out for special occasions, such as taking pictures of our "family."

After a time, when at her place, I only dressed as a man when she had a relative visit, which was quite rare (maybe twice a year).

Eventually, Sherrie broached the idea of me living with her 24-7, saying, "I wonder how you would like living as Anna all the time, and maybe even get breast implants."

I knew this was coming, but didn't want the idea to come from me. "Well," I replied, "I don't want to be going out in public as a woman, because I know people would see through me. People pick up so easily on gender, you know. In this town, going out as Anna would be scandalous. And so, I don't think breast implants would be good."

"Darn," said Sherrie. "I guess I get caught up in my fantasies sometimes. Like, people don't think my collection of dolls is too out of the ordinary."

So, we compromised. I did move in, photographic gear and all, and many of my best framed wildlife photos now adorned her walls.

Not that living together was all tulips and roses. She could be prickly about certain things, such as not wanting to be explicit about sexual subjects. For example, we used euphemisms for fucking such as "having fun" or "playing." Oral sex was broached by talking about "candy." I discovered that some of my favorite off-color jokes didn't make her laugh. As usual, she enjoyed telling me what to do and orchestrating my life. What irked me the most was when she talked to me in a one-sided manner like I was a doll (like when a guy calls his girlfriend his "doll" and treats her like one!).

What kept me happy, to be honest, was living as a woman there. Under her direction and instruction, I felt so carefree and captivated by acting, well, Victorian. Being polite and whimsical. Appreciating fine feminine clothing. Dressing to look rather sexy. Loving tea and muffins.

Together, we created a new book, this time not using her artist friend, but my photos of her dolls. When it was published, the book went over well because it appealed to both children and adults.

One time, we woke from a night of solid sleep where we'd spooned most of the time. It was so nice that neither of us worked outside the home and we could luxuriate in bed and get up whenever we wished. We were both, of course, wearing our lacy-topped Victorian nightgowns. I was feeling horny and reached down to put my hand over her cunt. That woke her up for sure. She turned around and our long hair intertwined as we kissed. Her leg went between mine and contacted my cock, which now woke me completely up. After a few minutes of that, she did the unexpected and pushed me onto my back while she pulled up her gown and squatted to mount me and insert my rod in her warm, tight vagina.

"Whew, Sherrie. Oh ... oh."

As she began to slowly raise and lower herself, I hoarsely asked: "Don't get too fast on that, dear." We both knew I had a tendency for premature ejaculation.

She soon began fingering herself, closed her eyes, and let out a brief cry as she came. It was so neat to see her reach orgasm, as the 'gasm rolled through her body and she tensed and shuddered, followed by smiles.

I had begun to thrust a little up against her, and came just after she did, ecstatically pumping my warm jizz into her. (Yes, she did practice birth control!)

So now we had a new option for our bodily get-togethers. I could tell she enjoyed being on top, pretty much controlling the penetration and tempo.

This tendency of hers eventually led to yet another variation. A rather major variation!

One time we were dressed all Victorian for some more fantasy photos of us with the dolls. She didn't do it much, but this time she'd chosen to dress in that Victorian man's outfit that I'd worn when I first visited many months ago.

She continued to wear the outfit afterwards -- complete with vest and a man's shoes -- and with her hair tightly back in a bun -- all that day. As we retired in the evening, and I was changing out of my corset and into my nightgown, and getting into bed, she had a rather wicked smile on as she turned down the lights low, and came to our bedside just wearing her man's long shirt, and ... an all-black strap-on dildo!

Smiling conspiratorially, she murmured, "Anna, dear, let's play parents. You're the mom, and I'm the father. I'm really horny tonight and it's your duty to please me, right?

"I've had this fantasy for some time, so let's pretend. Be a good wife and present your wonderful behind to me like a doggie, OK?"

"Oh, so now you DO want sex like animals?" I joked.

She laughed. "No, I mean just the position. Would you do that, my dear wife?"

In my many relationships with women in the past I had never experienced anal sex, except with a woman who sometimes ventured a finger up my anus (which I'll admit I liked). But this was taking things much further.

As I thought about being penetrated, my cock quickly went erect, which Sherrie noticed.

So I compliantly accommodated her and assumed the position, on our bed. I'm sure she gained the knowledge of how to do this from watching porn!

She thoughtfully lubed the outside of my little Anna vagina and her black, curved dildo-cock as well. Watching her grasp it as she rather awkwardly made her way over and aimed it toward my hole was thrilling, to say the least.

"Oh, Anna, are we really doing this? Maybe I should have a male Victorian name too, like Charles or Henry ... "

"Henry, Henry," I whispered, "I so want you in me. Please fuck me gently; I'm a virgin, you know."

"Henry" took a while to position himself, finally having to put a pillow under his legs so his prong was just the right height to enter me. He pushed up my nightgown.

"Anna, dear, are you ready?"

"Be gentle."

Reversing roles was intoxicating (I was pretty much saying what she said when I first penetrated her).

I felt the soft push of Henry's into my tight Anna's vagina. He played with tiny little thrusts. Being quite unfamiliar with the anal sensations this was causing, I can't say they were turning me on much. What turned me on, though was him holding onto my hips, which made me feel womanly and taken.

He then leaned over my back, and began to play with my nipples through my nightgown. Now, that got me going. Somehow those sensations merged with the anal sensations and I became fully aroused.

He began to thrust earnestly and deeper, but still, thank god, slowly.

"How does it feel to be fucked, Anna? Do you like being penetrated? Do you like my cock inside you?"

"Yes, oh yes, Henry. And don't stop playing with my nipples."

Finally, at one point, He just pushed all the way in and held there. His other hand now went down to my cock and began stroking it. It was completely wet with pre-cum. After only a few moments I had an all-consuming orgasm, the best one I'd ever had. And I told him so.

"You did this so adeptly," I complimented. "I can only guess you've learned much from the internet."

I couldn't see his face, but I KNEW he was blushing again.

"A proper lady would never watch porn," he said. "However, it was fine for Henry to do so. That's what most men do, isn't it?"

"Yes, of course."

After he finally withdrew his dick, he removed his harness, and I eagerly ate him (now her) out to orgasm.

So another whole avenue of fun and pleasure had been opened. She truly did have a strong need to play the male role from time to time. In her male role, her conversations with her dolls took a different turn.

Like, "Oh, Emma and Debbie, today we will play house with Anna as your mother, and me as your strict and demanding father, Henry. Anna, could you go prepare our tea and muffins? I'll go light the fire in the fireplace. Then perhaps you could read some children's books to the kids, while I read the stock reports in the newspaper."

And so on. I usually played along with her whims, but from time to time I'd tell her, or Henry, that she was taking her fantasies too far.

There was another development that was even more important. As I have said before, Sherrie followed web sites and blogs where the Victorian era was honored and promoted. Eventually, using my photographs, and working with a web designer, she opened her own web site promoting her books and her "family." Visitors to the site would often write her with compliments. Once in a while, some dolt would write in saying, "Your [sic] bonkers. Your fixation on dolls is crazy, crazy, crazy!"

One visitor wrote to tell her about a semi-secret organization in New Orleans called Piccadilly Lane which held Victorian-themed shipboard parties twice a year. The interesting thing was that most of the couples who attended were role-switchers, just as we were. The thought of attending at least once excited Sherrie to no end.

So, for the very first time, we took our own Victorian show on the road, as Henry and Anna. We flew down, and boarded the grand paddlewheel boat Mississippi Belle for a four-day excursion.

Sherrie and I used false names when registering, not wanting her author (or my photographer) status to attract attention. We were just another couple attending.

Guests were expected to always be dressed and acting in their chosen roles.

Sherrie had, for the trip, purchased some new sets of male Victorian clothing and suits for the occasion, and she looked rather convincing, even to the point of sporting a bushy mustache. And I, having so much cross-dressing and role-playing under my belt (or rather, under my corset) was totally relaxed and convincing in my role. I'd say two-thirds of the couples on the trip were reversing roles. Some of them were even better in their roles than Sherrie (Henry) and I, while others, to be honest, were sad caricatures of men and women.

We made friends with one of the best-appearing couples, Arthur and Grace, who hailed from Tennessee. We found ourselves sitting in the ship's elaborate restaurant with them one evening. I was wearing a lush dark-maroon dress with a small bustle. My corset presented my bust front and center, just as I liked. My earrings were elaborate and I wore long white gloves. The first day on board, my hair had been professionally styled in that wonderful uplifted style.

Sherrie (Henry) was outfitted as a riverboat gambler that night, and even looked a little rakish.

Arthur and Grace were similarly attired. Something about Arthur really turned me on. She/he wore tiny earrings and just seeing the evidence of ample breasts under her suit turned me on. Later that evening, a dance commenced in the ballroom, and as the southern Mississippi River shoreline slowly passed by, and one could hear the splash of the paddlewheel, I danced with first Sherrie/Henry and then "Arthur." She pressed herself against me, and my dick instantly rose to the occasion. How could it be that I both wanted to fuck her and wanted to receive her own stiff rod (which I assumed she had)?

We two couples retired to their cabin around midnight, where we had several nightcaps (as usual, Sherrie/Henry just sipped hers). While Henry and Grace just petted heavily, "Arthur" and I made our way into their bedroom, where he wasted no time with niceties. First, after some impassioned kissing, she unbuttoned her fly and out poked her red strap-on dildo, which had been pushed back out of the way before. She pushed me down on my knees, and inserted her member into my mouth -- way in. And without a hello, she began thrusting away, deep into my throat. This was giving her raptures already -- she was heady with pleasure. Forget about my needs!

Then, after she had me remove my dress (but not my corset) she positioned me on the edge of their bed on my back, with my bent-back legs raised up -- nicely presenting my vagina-hole. After quickly penetrating me, she held my ankles with her hands and went to town, fucking away. I rather endured this. She soon climaxed with a vigorous yell.

She explained later that her strap-on had a little vibrator that contacted her clit as she fucked me. I told her I'd have to get one for Sherrie.

Beyond that, I was miffed that "Arthur" didn't seem to care about my satisfaction. It was only her streak of maleness and aggressiveness that turned me on. With Sherrie, I'd become accustomed to being gently dildo-fucked and got a slight turnon from that, but this had been quite different.

When I eventually turned in, in our stateroom, with Sherrie/Henry, I was only too pleased when she performed oral sex. I needed that.

We continued palling around with Arthur and Grace, and the next time we got together after the dance, "Henry" and "Arthur" got together in their bedroom. "Grace" and I sat in their living room and compared notes about Victorian women's fashions while drinking cocktails. This loosened us up and we were soon moving closer together. Eventually we kissed -- lipstick to lipstick. That was nice, but my senses told me this was no woman.

Still, our hands sought out each other's cocks under all that fluffy material and under our drawers. After a few embarrassing moments, we found pay dirt and stroked each other's erections while we kissed some more. His dick was rather small, but still hand-holdable. Losing all control, we both ooohed and ahhhed and began stroking in a frenzy. We came at about the same time, getting our dresses a bit wet and sticky.

Sherrie told me later that she and "Arthur" just kinda kissed and rolled around together and didn't get into any strap-on activity. Darn, I would've loved to watch that.

And then the trip was over, in Natchez. We flew home as Derry and Sherrie.