Mrs. Doubtfire

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Ryans fantasy takes an unexpected turn.
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Many Feathers
Many Feathers
10,460 Followers

Like a lot of people, I'd seen the movie, far-fetched as it was. The idea that a man could impersonate a woman, and then try and fool his own wife and expect to actually get away with it was just a little bit much. But then again, it was only a movie after all, and meant for entertainment, not reality. Or so I thought anyway.

I had moved into a new Condo four month's previous. I was single, currently unemployed though I managed to make a living aside from a steady full-time job as a free-lance writer of sorts. I had a sizeable inheritance to draw from, as well if and when it was necessary, but even that wouldn't support me for long all by itself.

The Condo I'd just purchased was apart of a two Condo per floor type of architecture. I lived on the fourth floor of an eight-floor building. I had met my neighbors the same day that I moved in as we also shared an elevator that of course stopped at the same floor where we both lived. Donna and Steve as I met, and learned were my "down-the-hall" neighbors. Almost immediately I was attracted to Donna. She wasn't drop-dead gorgeous by any means, but there was something about her that caught my eye, and captured my heart. Silly as that was, especially with her being married and all, and a newly wed herself as she and Steve had only lived here not even a year yet themselves.

Donna had light brown shoulder length hair, nearly the same height, as I was at just under five foot nine perhaps, with nice full looking breasts, not too big, certainly not small. But of course, I'd certainly never seen them except in the occasional glimpses when we'd run into one another over the course of the days and weeks that passed when she'd wear a tank top, or tight fitting blouse, sometimes wearing a bra, sometimes not.

Steve traveled occasionally for his work. I knew he was in sales, some sort of regional or district Sales Manager or something, which required that he be on the road two or three days every week, and once in a while for a week or two at a time.

As time passed, I had even been invited over for lunch on a couple of instances, and even for dinner one evening when Steve had been in town. I enjoyed the opportunity I had to be around Donna, even though my "secret" desires and fantasies about her would certainly always remain that....secret. And, there was never any indication from her that we had anything more than just a neighborly relationship either, albeit a closely developing one. Still, whatever amount of time I could spend near her, or with her, I did.

I had just gotten out of the shower on a Sunday morning when the doorbell rang. As I had not gotten a phone call from security first down in the Lobby of the complex, I knew it had to be one of the tenants, and in all likelihood, it was either Steve of Donna above any others. I quickly threw on a bathrobe though I was still wet, and headed for the door. Answering it, I was delighted, though slightly surprised to see Donna standing there. She too was wearing a large fluffy bathrobe, and though I had received "glimpses" of her in the hallway, either saying good-bye to Steve on his way to work, or picking up a newspaper by the door, sometimes nearly less dressed than she was now. It was still a bit of an unexpected surprise to actually see her standing here now.

"Good morning Donna!" I said, actually holding the door open even wider as a silent invitation to come inside if she wished too. And without asking, or saying a word about it herself, she did.

"Morning Ryan. I hate to disturb you like this, especially this early on a Sunday morning, but as Steve is going to be gone for two whole weeks, I wanted to do something special for him, and I came up with fixing him breakfast in bed."

I stood listening, looking at her as she spoke to me, still unsure of what if anything I could do for her.

"I realized I hadn't had time yesterday to go grocery shopping, and wondered if you had a few things that I could borrow from you in order to fix him breakfast."

Donna actually produced a small paper from the pocket of her bathrobe with some of the things she needed on it. As she did so, I saw her robe part slightly, and for the first time got a brief glimpse of a rather well rounded and full looking breast. I'm not sure she knew, or saw that I had seen her, but "feeling" perhaps that her robe had parted, she quickly gathered it in with her hand and held it together while she handed me the small slip of paper she'd written a few things down on.

"Come on into the kitchen. I'll see what we can do for you." I told her.

As we rounded the couch in the front room, Donna happened to glance down at the woman's dress that was draped over the back of it.

"Oh Ryan. I'm sorry! I didn't think to consider that you had a "guest"!" She stated apologetically.

Confused, I looked over to where it was that she as looking and laughed. I'm not exactly the neatest person in the world to be sure. And spotting my sister's dress still lying on the back of the couch where she had dropped it almost a week ago was a little embarrassing. Not because Donna thought it belonged to some intimate "guest" that was staying over, but because I'd been too lazy to take and hang it up.

My sister and I were "Fraternal Twins". Regan and I certainly weren't identical, but even as fraternal twins; we looked a lot alike. Just the "obvious" differences between us being a man and a woman. Regan was an airline hostess, and as such, came through the city about every two weeks on either a layover or a rest stop between flights. The fact that I happened to live here made it much easier on her to save some additional money by staying with me when she did.

I quickly explained this fact to Donna, telling her that Regan had stayed over with me the previous weekend, just long enough to change clothes and fly out again. My sister had stayed with me a significant number of times, so that it became easier for her to literally take over one of the bedrooms and store a few articles of clothing here instead of always having to travel around carrying them with her.

It was then that I also pointed out one of the few pictures I had of my sister, which showed the two of us standing side by side. If it weren't for her having longer hair and a slightly different look with make up and all, it would have been hard for anyone NOT to see the obvious similarities in our appearance.

We finally entered into the kitchen, still laughing together over the initial thought that she'd had that I had a "friend" staying over, still sleeping in my bedroom. But the reality was, I did have a growing hardon, brought about simply by Donna's presence. The fact that I had a robe on wasn't helping much. The ease and "freedom" of having plenty of room beneath my robe wasn't helping to contain anything, and I had to ensure that I didn't twist or turn in certain ways that would have revealed this fact, or pointed out to her quite unexpectedly my rapidly growing discomfort. Trying to get my mind off the situation, I took Donna's list from her and began to look it over, pulling stuff out of the refrigerator, or down out of the cupboards. Before either one of us knew what was happening, I was suddenly making breakfast rather than just giving her the stuff to go make it her self. It seemed like the easiest thing to do, and I am sure I subconsciously wanted her to stay here as long as possible. I even had one of those "bed-trays" which Donna went and got from my bedroom, and we decided to prepare everything here, and then she'd simply take it home with her and wake Steven up with it.

As Donna and I stood together at times cutting things up, scrambling eggs, or making toast, I stole whatever glimpses and glances I could down her robe whenever it parted. I was reasonably sure that Donna never caught me actually looking, but it did seem to become apart of the "game" to some extent that we became aware of one another's nudity beneath our robes, and especially as I maintained an erection of sorts throughout the entire process.

Twice I know I had inadvertently touched her, brushing my hard cock briefly against her side once, and again almost directly against her bathrobe covered ass when she had bent over to pull out a frying pan from one of the lower cupboards. Neither of us said or mentioned a word, but I know that if "I" felt it....she certainly had to of felt it as well.

And as we cooked, we talked too. One of the subjects of course being my sister. I told her a little about Regan, and as we became more and more comfortable with one another, I also informed her that my sister was also "gay", or in more specific terms as defined by her gender, a lesbian.

"Maybe it's the fact that I know we're both naked beneath our robes...." She began. "And because of what you just shared with me, I don't know. But I confess, I have wondered about that myself. Even Steven and I have discussed the possibility at times when we've shared fantasies. Of course.....I'm pretty sure I'd never actually do anything like that, but I guess most women do wonder about what it would be like to be with another woman at one time or another."

Perhaps I shouldn't have been too surprised by her revelation. And she was right in one respect; our "covered" nakedness was still just on the edge of awareness for both of us. And I had seen both of her breasts fully exposed a couple of times now, and once had even thought I had seen the smooth surface of her sex when she'd sat down at the table and crossed her legs.

The image of Donna and my sister locked together in some sort of oral "69" with one another was still on my mind as we finally placed all the food we had made on the breakfast tray for Steve. Donna thanked me profusely for my help, even giving me a kiss on the cheek, and in doing so, allowed me to feel the softness of her breasts press against me even though it was through the material of her bathrobe.

Holding both doors for her, I escorted her down the hall as she carried the tray full of food, along with a fresh pot of coffee. Holding her door open for her, she once again turned to thank me, her robe now parting completely open as she did. With both hands holding the tray, she couldn't possibly reach to cover herself, and realizing this, simply looked down just as I did, and then looking back at me merely smiled, winked, and went inside.

I closed the door, smiling like a Cheshire cat I'm sure, and with a full-fledged hardon pointing the way back to my own place, whistled down the hall and looked forward to what I knew was going to be a rather extensive session of solitary abuse.

Even as I lay down on my own bed and began jerking off, I was surprised when images of my own sister entered my mind. I remembered a time not so many years ago when we were still fairly young teens, forced to remain inside the house due to a severe storm. Bored out of my mind, I'd asked Regan if she'd be willing to play one of my "War" board games with me to pass the time. She agreed to do so, but only if afterwards I'd be willing to do something that she wanted to do too. Perhaps I should have asked "what" even then, but was so excited to actually get to play one of my favorite games, I agreed, and perhaps too quickly as I later found out.

After the two of us had played "my" game, which she had won to make matters worse, we then played hers, which as it turned out, was to turn Ryan into Regan. For the next hour I was subjected to wearing eye shadow, lipstick, a play wig that was very similar to Regan's own hair, and after cutting it to look like hers, I was surprised at how much we truly did look alike. I had stopped short of her request for me to put on any of her clothes, though I did allow her to fix me up with a pair of similarly sized "tits", which I had to admit was sort of interesting in a weird sort of way. Seeing the two of us standing side by side, looking nearly identical was a little freaky. And as further "fun" to our game, I actually went downstairs shortly after that, and managed to fool our mother into thinking I was Regan for a short time. Regan had often worn more of my clothes, so seeing me dressed as Regan might was far easier to try and get away with.

Once again my revolving fantasy refocused on Donna however, and the memories of her bare breasts and that briefest of looks between her legs was enough to finally bring about the orgasm I was desperately trying to reach with the use of my hand.

The following morning I had just settled down at my computer to finish working on a piece that I was doing for possible publication when the phone rang. I picked it up, wondering who'd be calling me, especially since I knew very few people, and also knew my sister wouldn't be back in town again for at least a month. It was "Security" calling, telling me that Donna had had some sort of mishap and had fallen down the stairs. I knew that she quite often "jogged" up and down the stairs as apart of her daily workout routine, and had admired her determination for doing so nearly every day. What I was then told however was that she had slipped on something someone had spilled, tumbled down a flight of stairs, and had injured her legs. As Donna's husband had in fact already flown out for a flight overseas no less, she had Security call me.

I quickly arrived in the lobby a short time later, and though they had urged her to take a trip to the hospital by ambulance, she'd declined, allowing me to drive her there instead. Hours later, Donna emerged with both legs cast. And though they had recommended that she perhaps spend the night in the hospital, she once again declined.

Donna was able to reach Steve via phone even while he was still in the air. And they discussed the dilemma that she now found herself in. She would, for a short time at least, need some special help and care. I hung around, ensuring she was comfortable and did the kinds of things that she needed and Donna was pleased to get and receive my help with getting her a drink to even fixing her a sandwich. To "both" of our surprise however, Steve was adamant about getting another "woman" in to help her instead of depending on me to try and do everything. Though Donna argued with him briefly about it, she finally relented and said she's see if her mother couldn't fly out and be with her until Steve got back at least. Satisfied with that, Steve said he'd call her back after he'd landed and gotten settled in, and that hopefully by then her mother would in fact be on her way.

As I sat there listening, the weirdest little plan suddenly started to form inside my head. I couldn't believe I was actually even considering this, let alone actually intending on doing it. But in the next instant, I was telling Donna that my sister Regan was due in, in the morning, and had planned on staying with me for a couple of weeks. And that I knew that "she" would be more than happy to help out whenever she needed anything.

Of course, Donna declined at first, stating that she was confident her mother could be here in a day, or two at the latest. But I argued that Regan would be here long before then, and that it would be no problem, or bother for "either" of us to help her whenever she wanted or needed it. And that we'd "both" just be a phone call away, and she'd still have her privacy and home to herself instead of having her mother flitting about. I had gambled on that idea, but it seemed to hit home with her so she finally agreed.

Knowing that I needed to buy a "little" time to get the few additional things that I needed, having Regan coming in the following morning gave me that afternoon to run out and do some shopping. And yes, it was strange to actually go to the drug store and buy a wide variety of products that I knew I was going to need to make the transition complete. One of which included a realistic looking wig that I could shape and style to appear more like the way Regan wore her own hair. The second problem of course was finding a suitable pair of "tits" that would not be "too" large regardless of any desire to sport any otherwise, and in fact, be "toned" down to some extent instead. Buying a decent bra, and then explaining to the clerk who sold me the undergarment that I was doing so as a "costume" she provided me with the necessary "insertions" to complete the required illusion. The fact that she smiled at me in a certain way wasn't lost on me either. Though frankly I could have cared less at that moment what she thought. The idea of somehow getting closer to Donna, even in this particular way wasn't something I was about to throw away if I had the chance.

That night after first having checked in on Donna, along with bringing her home something to eat and spending some time simply chatting with her. I informed her that I "personally" had some appointments in the morning, but that Regan, my sister would drop in on her first thing. Donna then gave me an extra key to give to her, and told me she was really looking forward to meeting my sister, especially as we had now gotten to know one another so much better. Just before I left, Donna told me that she was really looking forward to having Regan help give her a sponge bath. I nearly choked on that, and almost decided to forget the whole thing. But again, my cock "lurched" and the chance of actually getting to see that terrific body of hers, even if somewhat innocent, though clandestinely, was again something I simply couldn't turn away from.

That night I practiced a far more effeminate voice. I had been a reasonably good singer in High School, and once again used the falsetto of my voice to give myself a half decent chance to pass as a woman in that way at least. All the makeup I had purchased could be washed off immediately with no telltale traces remaining if it was necessary. Taking several pictures of my sister, I sequestered myself in the bathroom and began practicing on making myself look as close to her as it was possible to do. Several hours later, I stood looking at myself in the floor-length mirror of my bedroom. Even if Regan herself had walked into the room just then, she'd have wondered which one of us was really her.

I went to bed that night, nervous, apprehensive, and horny as hell. I had no idea what I thought I would be able to get away with, nor to what extent. Mostly a little voyeurism in a way perhaps, and later as we became more confident and comfortable with one another, more, far more. As I was sure we would since Donna and Ryan had, my hopes then that I, as Regan, would become even more intimately associated with her in a confidant, female way.

In the morning I checked myself out meticulously, comparing my "new" self to every photo of my sister that I could find, I felt reasonably assured that I could pull this off. And, if at any point along the way I could come up with an immediate reason to leave and suddenly be called away due to my "on-call" flight status as a stewardess. Practicing my new voice, I then steeled myself and unlocked the door to Donna's place at a reasonable hour and called out.

"Donna? You up?" I called out in my well-practiced falsetto voice.

"In here!" I heard her exclaim. "I'm so glad you arrived, I was just about to try and crawl into the bathroom!"

Hearing that, I already had misgivings. I had of course considered that possibility, but thinking through it, realized that if nothing else I would simply on occasion help her into the bathroom, and then leave and wait for her to finish before she needed my help.

Walking into the bedroom, Donna looked at me and stared.

"Oh my. If I didn't know better, I'd swear you and Ryan were twins!"

Once again my throat caught, and I nearly fainted, almost playing the role too well here.

"I saw your picture in Ryan's front room. You're even prettier than your picture shows you to be." She added.

Many Feathers
Many Feathers
10,460 Followers