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More Fun Time With Sherry

"Mommy Sherry starts to show her feisty side."

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Days turn into weeks and weeks turn into months...

As time marches on, Sherry and I see each other more often and our notes at the stores are replaced with the usual conversation of a customer and associate. On weekends, she stops by my place and we talk, watch TV or do whatever is on the agenda. My co-workers and assorted friends understand that there is now a woman in the mix and to call ahead in case they want to stop by. Gone are the days where people could just drop in unannounced. There were a few times when they showed up when she was there, but were polite about it and all was fine.

My mother is famous for showing up like she owns my place now that she know Sherry and I are seeing each other. The usual remark is that she is in the neighborhood and decided to just stop by to see how I was, while I knew damn well it was in the hopes of finding Sherry with me. My mother knew I was pissed, since I cite the obvious fact that they live over fifty miles away. My father respects my privacy, but it took quite awhile before my mother could do the same. I tell Sherry that my mother needs to cut the apron strings and quit being so nosy, making her laugh.

When it was my turn to check out Sherry's abode, I am amazed at how open she is. Friends would just stop by as if they own the place, which is something I am always uncomfortable with. They are told about me and act like I was intruding on their turf. Sherry has to be polite and give a general response, telling them that I am a friend and that we are seeing each other. After awhile, she starts to put her foot down with her friends, reminding them that it is her place and that she wants more privacy. They get the message, even though a few are pissed off. Her place is a bit smaller than mine, but very inviting. Being in the city is okay while I am working, but I like my privacy, whereas Sherry's house is in the mix and her area gets quite lively on weekends. On one visit, she decided to test her limits.

We go to the second floor and she walks me to the back to a room I never saw before. It has two chairs and on a table is an unfinished jigsaw puzzle and I tell her I haven't put one together in years. She then asks me to strip and put everything in the hamper. Her washer is in the basement, so the thought of a clothes hamper in this particular room is kind of odd. She keeps hers in the upstairs bathroom, whereas I keep mine in my bedroom. There are spare jeans and such of mine in one closet in her place, so not a problem. I am naked as she hands me a small box.

She giggles and says, "I got you something, Davey."

I have no clue what she could have picked out for me. Inside the box is a multi-pack of bikini briefs for men in various solids and stripes. She asks me to model one, so I select the plain navy blue one to be on the safe side. I put it on and it fit just perfect. I model it for her to show off my toned form. She puts the rest of the box into the hamper.

"See," Sherry tells me. "I knew they would fit your cute little buns. Now, take them off and try these on for me."

I take the brief off and toss it into the hamper and go to open the next box. It is gift-wrapped and I have to take all the stuff off to get to it. I undo the paper, open the box, turn it around, take one look and drop it like a hot potato! I yell at her as I speak.

"Holy shit! You're fucking crazy!!!!!" 

Sherry just looks at me and seems puzzled.

"Why? What's wrong?"

I glare at her and pretty much yell at her. "What's wrong? They're panties. For women!"

My face is beet red as Sherry picks up the box and hands it back to me with a sly grin. I blush as she talks to me in a sexy tone.

"They are in the correct size for you. Besides," she adds, "anything that is worn underneath clothing is a panty to me, no matter if you are a man or a woman."

After thinking it over, I decide to play along and put on the white bikini brief on for her. The soft cotton feels good and the fit is snug in front. I start to get aroused again and blush. She has me model it for her and applauds.

"See, Davey," Sherry tells me. "They fit and you look very sexy! I might even get a thong or two for you, as well."

I decide to model a few more for her in various cuts. Full, high-cut and string bikini. Each fits and she tosses the remainder of each pack into the hamper. I take the last one off and look at her.

"Now, stand with your arms out to the side for me, please."

I do as I am told and stand naked my arms outstretched. She returns with a yardstick, ruler and measuring tape.
 
Sherry calmly tells me, "Now, let's take care of this, shall we? Let's get this out of the way first."

I feel her soft hands on my penis and shiver. Then, with ease, she is able to tuck my item inside and my crown jewels, as well. She secures what feels like a bandage over the area and adds more tape to secure it quite firmly. I look down and my manhood is gone. She stands back and smiles, admiring her work.

"There," Sherry says. "Your little sausage and dumplings are out of the way. Oh, and you need to shave that clitty of yours."

 I ask what she is talking about.

"Shave your pussy hair,'' Sherry tells me. "I want that area silky smooth from now on."

Sherry then rolls the full-length mirror out and measures my waist, hips, inseam and other items of interest. She pats the front of me and smiles. I blush and she knows I somehow like this. Once finished, she asks me me to look at myself in the mirror. I am upset that nothing is in front, but am amazed at how I look. I am actually aroused by my new look, but I don't dare tell her.

"You look lovely with your penis out of the way. You will look even better with a clean clitty. Now, come here."

Sherry then takes me over her lap and spanks me with her open hand ten times per cheek and smacks me with the ruler five more times. She then leads me to a corner and pinches my sore behind, causing me to squirm in pain.

Sherry then talks to be in a clear tone. "Now, my little girl, you stay right there for five minutes."

I remain quiet and do as I am told. With my stuff still inside, she returns and asks me to face her.

"Why am I like this?" is the first thing I say to her.

"I needed to measure you for clothing," Sherry tells me. "Plus, all naughty girls need kept in line. From now on, you shall stand in a corner for five minutes if you act up. Now, hold still."

Looking at her, I tell her, "I am not a girl! I am a boy!"

She reaches down and pats my private area.

"Do you see a penis in front? No? I didn't think so. That means you are a girl. I can always leave you like this."

I am beet red with shame as she walks away from me and stands at the doorway. I am amazed at how powerful she looks and the amount of control she now has over me. She leaves the room and is gone for what seems like forever. When she returns, she stands before me with her hands on her hips. I am sobbing, so I choose my words carefully and she is amazed at how pathetic I look as I talk to her.

"I will behave, Mommy. I promise I'll be a good girl. But, can I be a boy now? This is starting to hurt."

Her face lights up now that she knows she can control me with relative ease. She gently removes the bandage, telling me she wants me to shave down there, something I have never done. It hurts as she pulls the bandage off, so I will try my best to remain clean down there.

"Be a good girl and shave your clitty for me, or I might let one of my friends do it for you."

The thought makes me decide to do as I am told, but I become hard at the same time.

"Yes, Mommy," is all I can say to her.

She looks at me and grins. Sherry goes on to tell me that since she now has all of the needed measurements that she can now buy me things and know they will fit properly. I am upset when I am told that she might take some of her friends along to select the panties and assorted items.

"As long as they behave," I tell her.

"Okay, but what makes you think that some of my friends didn't go and buy these panties for you in the first place?"
 
I look at her and realize that this could have been a set-up the entire time.

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Sherry wanted to see how far she could go. I don't mind my body, but there are only so many I would show it off to and her friends are not on that list. Still, the intrigue appeals to me and I become aroused now that my penis is free. Some of my male friends have seen her fine body, but this is quite different, however. I have seen some of her gang and they are a wild mix. I have no clue what that would do to me.

She hands me a pink brief, lets me put it on and then calls me over to the chair and sits down again.

"Come here, Davey. Or, should I figure out a girly name now that you are wearing panties? Put your hand up above your head and come here. Now."

Once I get to her, she places me over her lap, slowly pulls the panty off and drops them in the hamper. I notice it has become a bit fuller. With my ass cheeks fully exposed yet again, she proceeds to spank me several times with her open hand, then opens the drawer of a table next to her. Sherry pulls out what looks to be a standard Ping-Pong paddle, gently taps my behind with it and then swats me with it for a quick sting. Turning it to the side reveals that it is a bit thicker.

"There, all finished. That wasn't so bad."

I stand up and she shows it to me.

She responds, "I ordered this when we were at the local craft fair. Remember? It was so cute that I had him make one for me. Look at it."

She turns it around and right there in the middle in plain sight are words that me makes grin and want to laugh: "Mommy's Paddle."

Turning to face me, Sherry hands it to me and tells me what to do.

 "Now, I want you to sign it as proof that I used it on you. I will be the only one to use this on your cute little buns."

Taking her pen, I calmly write below her name - 'With Love, Your Baby, Davey', date it and draw a heart on it, causing her to giggle and blush. She then reaches behind me and shows me a second one. This one is somewhat larger and I cringe as she speaks.

"This one is for anyone who ever decides that you need a good swat!" Sherry continues, "It will cover more of your tiny tush. Also, they will get to add their names to it and you must call them Mommy. If they want to bring their own paddles, so be it. Who knows, I might even allow your own mother to spank you and use my paddle on your bare bottom. I can just picture her making you stand in your naughty corner with your sore behind on display."

"You're crazy," is all I can say. She can tell I am pissed off and just smiles.

"Yeah, I know", she says. "But, you like that side of me, right?"

I calmly tell her, "Then there needs to be ground rules."

"Yes, you're right," Sherry tells me. "They will need to be fair, yet firm, as you said Marty was. Besides, girls get spanked and boys get paddled. Depends on how they see you, my dear. Now, get in position."

She then gives me five solid whacks on each cheek and orders me to count as she does. Each strike feels a big more painful, but my toned ass can take it. She then smacks me with the ruler and a few slaps to seal the deal. After getting up, she takes a marker and signs and dates the back of the new paddle, as well as her ruler. Thankfully she did not use the thick yardstick.

Then, in a direct tone, she says, "Now, follow me."

She walks me to a different room and orders me to face yet another corner. Thankfully I am hidden, rather than out in the open like the other room is.

"You will stay here for fifteen minutes and remain quiet."

She pinches my bare thighs, causing me the wince and yelp.

"I said be quiet!" Sherry tells me. "I guess I might need to get something to keep that mouth shut. Duct tape, perhaps? And, just for that you'll stay here for thirty minutes."

She digs her nails into my behind and pinches me. I am able to stay quiet. After a pat on my rump, she closes the door and goes about her business. I try to remember which room I am in and how it relates to the outside. There is a window on the adjacent wall to my right with a lace curtain. It lets the sun in, but nobody can see me from where I am. Once I get out of here, I plan to check the house out further. For now, I stay motionless. When the time is up, she comes in and tells me my sentence is over. I ask her my question.

"Why was I standing in here?" I say to her.

After thinking things over, Sherry is very direct.

"I will just tell them you were a bad boy and needed some corner time. Besides, this room is seldom used, so I could close the door, turn out the lights, lock it from the outside and nobody will even know you're in here. I'm sure I could get some things to make you more comfortable if I feel you need to stay in here."

"We need to keep this between us, okay?" is my lone comment.

"Well, I suppose so. For awhile, at least. But, if you are naughty, I will stand you in the nearest open corner, no matter who is already here or shows up. Five minutes for the girl in you and fifteen for my baby boy. If someone shows up, they will get the chance to use my paddle, add their name to it and stand you anywhere they choose. That would be fine by me and they can add to your corner time. Trust me, they would all get to see just how much control all women can have over you."

She leads me to the spare room where my clothes are and has me stand at attention.

"Here, put this on and get ready. Oh, and I might even invite Susie over so that she can do as she wanted to and beat your little ass. I think she'd like that, and so would you."

I cringe at the idea of that bitch seeing me, so I get my stuff on before anyone shows up. Thankfully, I get to wear a manly thong and jeans. After getting fully dressed, we dine out on her enclosed patio and watch the sunset. As I prepare to leave, we embrace and pat each others' clad backsides.

"I'm glad we shared this time together, Sherry."

"Yes, David. And, I might just have to find a feminine name for you when I decide to have you wear panties. I think it would be so sweet. I'll wash all of your panties along with the rest of them."

I give her a dirty look and asked her what she meant by that.

"They had a sale and I kept the receipt in case they didn't fit. I will add them as needed. Don't worry, your mother didn't help pay for these. But, you never know if she might help in the future."

I cringe when she repeats that word, since I still call guy's things as underwear. But, if it pleases her, I can't complain. That naughty devil knows me all too well. The idea of being seen in them arouses me, even though it does seem a bit weird. The idea of a dress drawer filled with male attire and panties, a closet full of jeans and such for me is both upsetting and exciting. Before I leave, I notice a glass jar with money in it and decide to add some of my own.

"What's that for?" Sherry asks in a puzzled manner.

"Well, you said they were my panties," I tell her. "It seems only fair that I should help pay for them, as well as other items you and your friends might pick up. Also, keep my mother out of this."

She tells me she will not involve my mother in any way and pats my bottom as I leave. She hints that it might actually be fun, although she understands that it would be tacky and very humiliating.

It is dark as I walk to my car. As I drive home, I can't help but wonder what might be in store for me later on. The thought makes me hard as I continue. I am all man, but the idea of modeling for her in whatever she pleases is very arousing to me. Things could get a bit dicey if her friends show up. But, I'll handle that if and when the time comes.

I get home and immediately go to the bathroom. I am able to let out all of the sexual energies that came to me over the past few hours. The release is well worth it. I have a full mirror on a door in my bathroom and laugh at the idea of shaving my genital hair. But, time will tell where this may lead.

Published 
Written by David929
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