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Ms. Bakers New Sissy


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I was desperate to pee and the only possible place was the basement laundry room, and I almost made it. I was praying that I wouldn't be seen as the elevator reached the lobby and odds were in my favor. There were sixty tenants in the building, counting my aunt and confrontations were rare. Of course I didn't count on Murphy's Law

Murphy's Law states that anything that can go wrong will go wrong and I thought of that the instant the elevator stopped at the Lobby floor. It was Ms. Baker and there I was in wet pants and no where to hide. Her slight smile after a moments pause said it all although she also noted the obvious when she suggested I use a bathroom in the future.

I didn't want her thinking the worse so I quickly told her about my aunt losing her key and taking mine which left me locked out till she came home from work. That was still nearly three hours away and I'd had to go the instant I'd gotten to our floor and hour ago. I tried holding it for as long as I could but couldn't and there I was - soaked.

I was grateful when Ms. Baker told me to come into her apartment. I could get out of those soaked things and avoid a rash, she warned which would give her a chance to launder everything. I didn't think about it leaving me naked till I was half way through the shower, wondering as I washed, what I would do for the hour it took to wash and dry my things.

"What's your waist size," Ms. Baker yelled from the other side of the door. I was, according to my aunt, skinny as a rail and favored their mother's side of the family since I was so damn short, yelling back to Ms. Baker my waist size as I dried. From the other side of the door came an apology first.

I had two choices: Ms. Baker had a niece my size with a few things left from her visits. I could wear a blush pink satin robe with nylon panties or a pull-up under a cotton night shirt. Her niece, she noted as I weighed my options, sometimes wet her bed. Staying naked, she warned, was not an option.

Girl's panties and a pink robe or diapers and a nightgown? No choices at all but I was sure choosing panties and a robe would be slightly worse than a pull up and cotton nightshirt. I chose the last two and took both after opening the door only slightly. I was actually considering the panties and robe when I had a chance to actually see the items I'd taken.

They were good nights and yes they pulled up like underwear, but were clearly diapers. Girl diapers and that too was clear. White with pink hearts and ballerinas dancing around the front. The nightshirt wasn't a nightshirt so much as a far too short nightgown also white with pink trim. There were little pink bows at the puffy sleeves and another at the lacy neckline.

"It would be that long before your things are dry," Ms. Baker said obviously considering what I was considering. Even a minute or two was too long to be in these things but I had no choice and again I was given the option of panties and that robe. I also had to share the bathroom till the Super came to fix the other in Ms. Baker's room.

"Thank you," Ms. Baker said as I came out of the bathroom. She hurriedly passed me - thankfully not giving her much time to see what I was wearing. I was grateful for that small favor when she added that she'd put out cookies and milk. At least I could sit and hide the bottom part of my humiliation.

I was eating the second of three cookies when Ms. Baker returned noting as she fixed a cup of tea that everything seemed to fit OK. It did I said, thanking her for at least trying to help making her laugh a little. Since she was the only one to see me then there was no harm, other than to my ego, and that, she promised, would fix itself over time.

She also had some other news. The dryer circuit, which had kicked off again, had also been called in for the Super to fix. What it meant, she noted apologetically, was that I would be in those things I was wearing, for a little while longer than before. At least till my aunt could give me a change of clothes after she came home.

It was four, my aunt was do home at six or six thirty depending on traffic and there I was in a girl's diaper and nightgown. Murphy's Law was in full effect as I started to eat the last of the three cookies. Her niece, she noted, was almost ten. Somehow knowing I was seven, almost eight years older than the girl and her clothing made it worse.

It couldn't get any worse I thought and then my cell phone went off. It was my aunt and I avoided most of the details about my plight as she herself apologized. She was running late, very late and may even have to stay in town leaving me with only one option. Ironically she was about to call Ms. Baker and ask if she would take me in on an emergency basis.

I couldn't help but frown a little more when I handed the phone to Ms. Baker. She would be more than happy to help, telling my aunt not to worry. I felt my heart skip at least one beat when Ms. Baker told my aunt, not to worry, she had lots of clothes I could borrow and plenty of food.

Plenty of cloths to wear had to be a joke I mused with a touch of fear as I shifted in the chair. The diaper I wore wasn't seriously thick but it was clearly a diaper and padded enough where I sat to know that. I could also feel it gathering between my legs and worse how short the nightgown was in length. The nightgown would not cover the diaper and wondering what might gave me goose bumps.

"I was joking about the clothes, but you might reconsider the robe. It's going to get a little chilly tonight," Ms. Baker said and added, "and it's a little longer than your nightgown."

"Here try these," Ms. Baker said after returning with the robe. I had nodded a yes to her offer thinking at least the robe would hide the diaper and she went off to get it. She did have the robe in here hand and in the other a pair of shoes.

"Who would have thought," Ms. Baker noted as I slipped the first shoe on after the robe. I'd had to stand to get the robe on and did so with a face turning crimson from the embarrassment of Ms. Baker catching a glimpse of the diaper I wore and a full view of the nightgown I had on. She was commenting on the shoes that also belonged to her niece and how well they too fit.

Pink satin robe lined in blush pink nylon that only tied at the neck over a nightgown trimmed in pink that didn't hide the diaper I'd stepped into, and now the shoes. Everything fit as if they were my things and I didn't dare say that. Unfortunately Ms. Baker did wondering if that meant everything. I didn't add a word fearing she might want to find out.

"Dinner is at six so why don't we sit in the living room and chat," Ms. Baker said as she moved to the stove with her tea cup. I nodded cursing my aunt as I stood. Ms. Baker allowed me to walk ahead with another glass of milk as she followed with her tea. I wondered, as I walked, what I looked like from behind and was my behind as big as if felt? I would have fainted had I been capable of reading her thoughts.

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"There we go," Ms Baker said plopping down on the love seat directly across from the chair I had chosen.

Bad Idea I realized. This particular chair was a bit larger forcing me to try and keep my legs together after I realized that neither the robe nor the nightgown would hide the diaper otherwise. I could cross my legs as a girl might but I wasn't sure I actually could. I definitely did not want to bring my legs up and under and crossing my legs like a boy would be even worse.

It wasn't just worrying about what Ms. Baker could see but the view she now had of me. Not only the view but I instantly felt the diaper gather beneath my testicles when I sat. Like a gentle warm hand between my legs and under those testicles pushing them up softly. On top of the diaper there was the nylon under the satin of the robe moving slightly with every movement I made.

"Is this the first time you've worn a girl's diaper," Ms. Baker asked.

"What," I answered realizing first that she might think I've worn a diaper before this and shocked more that I might have worn a boy's diaper besides as I added, "first time in a diaper that I can remember."

"I'm assuming that goes for the girl clothes as well," Ms. Baker added before she took a sip of her tea.

"Yes ma'am," I said wanting to challenge her assumptions, whatever they were, and not daring to say another word.

"It's just that you seem very comfortable in both a diaper and those girl clothes, and I couldn't help but notice how well you keep your legs together. Frankly, that's not an easy thing for a boy," Ms. Baker noted before dropping her voice a little and adding, "I find it very attractive."

"Excuse me," I said shocked again. I was still trying to decide what it was that made her ask such a thing and now this... this attraction? What in heaven's name was she attracted to as I asked, "attractive? I would think a boy dressing in anything not male, even masculine or, for that matter, age appropriate would be a turn off."

"I suppose most women, although I would have to see the statistics, might agree with you, but frankly I find a little femininity in a man very refreshing and something of a turn-on. That and the fact you're wearing a diaper... Honestly, if you were to ask me what I might think of a man wearing a diaper I would have laughed but facing one wearing one is definitely not making me laugh.

"Do you know men that do this? I mean do this for you," I dared to ask. I had no choice in what I was wearing nor any hint of how long I might be wearing these thing. Truth was it could be all night and at least knowing it didn't scare the woman facing me was a little comforting.

"Good heaven's no. Frankly, there have been very few men in my life, truth be told and of those few none as girls or babies. I'm sorry if I gave you such an impression. It's just that if I were to consider such traits... traits that prompted such things I might consciously argue against such things. However, having seen it, you know, first hand, and on someone so attractive besides, well... well, it has changed my notions of such things drastically," Ms. Baker noted.

"why," I asked feeling a little more comfortable.

"femininity. That is to say some amount of femininity is a trait I find comforting in a male simply because I don't have to explain myself so greatly. Even if you're really not feminine at least wearing something feminine gives me a leg up on trying to define my behaving in ways considered typical for women. For example, you're crossing your legs female for the same reasons females cross their legs," Ms. Baker noted.

"OK, I can understand that but what about the diaper part," I asked feeling slightly more comfortable talking with her.

"That precious, hits me directly in the center of whatever it is women have that makes them naturals at having or caring for a child. Truth be known I instantly wanted to cuddle you the moment I realized you were wearing a diaper," Ms. Baker noted.

Without realizing it till just then, I was getting turned on and that oddly enough my erection, climbing slowly within the soft warm diaper only made it more sensuous. I found myself wishing desperately for a private moment to make the necessary adjustments that comes with a penis now almost three times it's original size. I could even feel the beginnings of pre-cum forming and being absorbed by the diaper as I lost my train of thought.

"I'm hoping what I've said hasn't scared you too badly. We have the potential for a long and interesting night ahead of us I think and I'd hate to start out by scaring you," Ms. Baker said and added, "and please, call me Julie."

"It's not scaring me. OK, I mean I'm uncomfortable, a little. Especially in these things, definitely uncomfortable, but what you've said so far has made it a little easier I suppose. I mean I wouldn't want the world to know about any of this, definitely not my aunt either," I said losing a little of the pressure that had been building in my diaper.

"I hope you believe me when I say this would definitely be just between you and I and I suppose I should add, now that the ice is broken at least a little, would you... could you find me, someone as old as me, even a little attractive as well," Julie asked with a very wicked smile appearing suddenly on her face.

"You're kidding right? Ms. Baker... I mean Julie, you're hot. Very hot and yes, I find you more than a little attractive," I said feeling my penis pushing right to the very edge of the disposable diaper. The tip, growing very sensitive became painfully so as it tried pushing it's way out of the diaper.

"Would you mind sitting beside me," Julie asked patting the coach cushion next to her.

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I like the way this story is written, even though I'm not normally interested in sissy stories. It flows very nicely and provides some good suspense. Hope to read more! :thumbsup:

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