A Sissy for Sarah Pt. 03

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Sarah disciplines me. Her period starts.
2.9k words
4.57
15.6k
13

Part 3 of the 4 part series

Updated 06/16/2023
Created 03/21/2023
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Alice64
Alice64
262 Followers

(Please be sure to read the intro story and Part 2 before proceeding)

Mom was teaching me about make-up and girly things and how I could be more feminine. I was told to wear lipstick daily, even when the girls weren't wearing any. Mom taught me how to paint her toenails while she watched TV in the evenings. Mom surprised Sarah one night and told her I learned to do this and had me paint Sarah's toenails. I think it was also an excuse for Mom and Sarah to sit on the couch together. One would put their feet in a foot bath I prepared for them and soak their tootsies while I painted the other girl's toes. They wear only their panties and bras. I had to keep my head down and keep my eyes on my work, but when I could, I glanced up I would see them kissing and feeling each other's breasts. When I was done with theirs, the girls painted my toenails bright pink.

When we were alone, I asked Sarah if Mom was still coming in her room at night and sleeping with her. Sarah admitted, "She comes in about 2 or 3 nights a week. I go to her room too sometimes now too, Tammy. I take her panties off and crawl into bed with her naked. Mom says some people might call what we do, incest, but Mom calls it Family Love, although she says we shouldn't ever tell anyone. We do smell each other's panties now too, the way you used to do it in the laundry room behind our backs. Mom's pussy smells so good! Then we masturbate each other, you know, putting our fingers in each other's pussy. And sometimes we do this scissors thing that Mom showed me, and we rub our pussies together. Tammy, it gets me so hot and feels so good! I wish you had a pussy Tammy so you could feel this too. I still haven't licked her down there yet, but she says she still wants me too. She said maybe she will have you lick our pussies together. Wouldn't that be nice, Tammy?"

"Oh, Sarah, really? Both you and Mom? Do you think she was serious?"

"I think so. She already let you lick her panties."

We let the conversation drop.

One day after school, Sarah was in a bad mood. Mom says when that happens it usually means Sarah's period is coming. I tried to avoid her by staying in my room, doing homework and keeping busy. My chores were done but apparently Sarah's weren't. Even though Sarah is my best friend she still oversees the household when Mom isn't home, and I have to obey her. Sarah called me upstairs and wanted me to do her chores. Sweep and mop the kitchen and bathroom floors. I think it was because of her moodiness. I told Sarah, "I don't think that's fair Sarah. I did my chores. Those are your chores."

"Tammy, you're not allowed to argue with me when I tell you to do something. It's not always going to be fair around here, now that Mom and I are in charge of you."

I continued to argue. Maybe I was getting in a bad mood now too. "But Sarah, you know this isn't right..."

"Tammy, don't 'but' me. I'm sorry but when you talk back Mom says I have to punish you. Go get Mom's hairbrush."

"Sarah, please. You don't have to do that. I'll do the floors."

"Yes, you will, but after I punish you. I'm sorry Tammy but this is the way it has to be."

I went to Mom's room and got her hairbrush from her dresser, brought it down and gave it to Sarah.

"Tammy, I won't punish you as hard as Mom spanks me with this because it's your first offense with me and you went and got me the brush. Mom says you have to go over the back of the couch. Go get in position, lift up your skirt and pull your panties down."

I didn't want to, but I really had no choice. I didn't want her to punish me harder if I didn't comply, and I really didn't want her to tell Mom about this. I went the couch, lifted the back of my skirt and pulled my panties down just below my ass cheeks. Mom's hairbrush was hard plastic, about 4" wide with a short handle. Sarah walked over to me slapping the hairbrush in her hand, making a loud smacking sound. She seemed upset with me. "Tammy, when I tell you to take your panties down, I mean all the way down!" She ripped my panties down the rest of the way, and they fell around my ankles. She said, "Tammy, try not to wiggle or flinch. You're not allowed to. Don't tense your cheeks. It hurts more. Spread your legs and keep your hands on the back of the couch." Sarah lightly tapped my cheeks with the brush to make sure I wasn't tensing, and I could feel my cheeks jiggle. Then she smacked one cheek, then the other with two stinging slaps.

I screamed out an "ouch!" It stung like crazy, but I held firm. She applied 3 or 4 more to each cheek and my knees began to buckle and I started to yell and scream. I started to stomp my feet. "Please, Sarah. That's enough. I won't disobey you again."

"I told you not to wiggle. I'm sorry Tammy but now you will need a few more. Hold still for me!"

It felt like Sarah spanked me even harder, 3 or 4 more times. I wasn't counting. I just hoped it would be over. I started crying. Maybe I have a low tolerance for pain or maybe from the sheer embarrassment of my best friend spanking me. But at the same time, I was as hard as could be, my boner brushing up against the back of the couch. Sarah gave me 2 more on each cheek and then told me it was over. I reached back to feel my burning bottom. Sarah went the kitchen and brought back aloe vera gel. She said, "I'm sorry I made you cry, but you deserved it Tammy, for disobeying me. This will help ease the stinging," and she rubbed some aloe on my bottom. I liked her touching me back there. Something she had never done before. I think she felt sorry for me. But I was conflicted from the pain and what I was feeling in my penis.

Sarah saw my erection and her sympathy for me turned around and she grew angry again. "Tammy, a boner? This wasn't supposed to excite you!"

"I know, Sarah. I'm not sure why this happened. My butt is burning!"

Sarah was disgusted with me. She turned my shoulders to face her. My penis was jutting out in front of me towards Sarah. "Hold up your skirt, Tammy! Spread your legs!"

As I did, Sarah took the hairbrush up under my spread legs and slapped my peanuts. Twice. Then two more times. Still in tears, I winced and reached down to hold my peanuts. Sarah laughed. I had never seen her so cruel towards me. I think Mom may have put Sarah up to this to see if she could discipline me. And now it would only get worse.

"Tammy, take all your clothes off and go stand in the corner facing the wall until that goes away. Then you'll do the floors naked!"

I'd never seen Sarah like this before. "Sarah, please. Why are you doing this? You've already punished me. I've learned my lesson. Please don't humiliate me further."

"Are you arguing with me again, Sissy? I still have the hairbrush! When I tell you to do something, don't ever talk back to me! Do you understand me?"

Those were Mom's words. My younger friend. Humiliating me. Being treated like a child. Mom used those words on me several times. I always had to answer that I understood.

"Yes, I understand Sarah. And I'm sorry."

"You're still dressed! Get your clothes off and get in that corner! I'm not going to tell you again, Tammy!"

"I'm sorry, Sarah. I'm getting undressed."

Sarah watched me undress. I hurriedly kicked off my panties and took off my top, bra, skirt, stockings and heels. Sarah told me, "Fold your clothes neatly!" Ashamed and naked, I tried to cover myself as I walked to the corner and stood with my hands at my sides facing the wall. My cheeks were still red and stinging, but my erection was beginning to subside. About 10 minutes later, it felt like 30, I called out to Sarah, "I'm okay now, Sarah."

"Did you stop crying too, Sissy? Turn around and show me." I turned around and faced my best friend naked, feeling vulnerable and thoroughly humiliated. Sarah said, "Ok, now not another word from you. Get the floors done before Mom gets home." I felt ridiculous in front of Sarah. Wearing gold hoop earrings, my red painted lips, my red bottom and pink painted toenails. I tried hiding myself from Sarah's view but that was impossible. Sarah laughed at my predicament and red bottom and said, "Tammy, your penis is so small when you don't have a boner!" I couldn't have been more embarrassed. I realized Sarah had only really seen me when I was hard.

Sarah sat on the couch and got on her phone, talking to a girl from school while I worked naked in the kitchen on the floors. Her moodiness seemed to disappear as she laughed with her friend on the phone. Mood swings. Her period was coming. It still wasn't fair, being punished and having to do her chores, and humiliating me, but I was no position to argue or disagree with our family dynamics. I finished her chores, and I went to Sarah, naked, my penis was beginning to stiffen again, a mind of its own, and I stood in front of her. I tried to cover it with my hands. I didn't want any more punishment or for Sarah to make fun of me for getting another erection. "Sarah, may I be excused and go to my room?" I had never asked for her permission before, for anything ever before. But I felt obligated to ask her now.

She acted sympathetically towards me again and said, "Tammy, I'm sorry I had to discipline you and humiliate you, but you'll know what I expect from you from now on, won't you?"

"Yes, Sarah. I apologize for my behavior."

Sarah picked up her phone and snapped a picture of me. "You're excused. Take your clothes. Wear a panty diaper tonight. It will pad your bottom and be easier on you."

I said, "Sarah, please don't tell Mom about this." She smiled mischievously and didn't answer me, but I knew that Sarah tells Mom everything.

The next morning, I stayed in the diaper under my pants. My bottom was still sore. I didn't want to sit down for breakfast, so I grabbed a glass of orange juice and told them I had to catch an early bus for school. Before I left, I noticed Sarah had left the hairbrush out on the coffee table. I think she did it on purpose. She wanted Mom to see that she disciplined me. I'm sure they discussed that after I left for school...and probably laughed about it. I was relieved Mom didn't get to see it. How awful it would have been to be punished like that with her Mom watching.

The next day Sarah was complaining to Mom about cramps. Mom looked at me and said, "Sarah, gets terrible cramps and mood swings." I was all too familiar with the mood swings!

"Sarah, you know that means your time of the month is coming. Tammy, it's her period, her menstrual cycle. A way for a woman to relieve her cramps is by having an orgasm. Sarah, go up to my bedroom, get undressed and I will masturbate you. Tammy can watch and see how it's done."

"Mom!," Sarah shouted.

Mom said, "Honestly! I'm shocked at the way you two behave. You know we have an open household now. You've both seen each other naked, taken a bath together, even watched each other masturbate. You know I've done this for you before, Sarah. I want to show Tammy how she can help a woman in need when she has cramping. Now, Sarah, don't make me tell you again. Get upstairs, take your clothes off and lie down on my bed."

We all went upstairs to Mom's bedroom. Sarah turned her back and began undressing. I thought maybe this was my sweet revenge for how Sarah treated me yesterday. Karma. Mom said, "Sarah, I don't understand why you're being so shy. We've done this before."

"But never in front of Tammy! I had to spank Tammy yesterday!"

"Then I'm sure you had your reasons and she deserved it. I saw the hairbrush out. But this isn't about Tammy now. Tammy is a Sissy. She needs to learn about this. Do you want Mommy to be naked with you?"

"Oh, Mom, yes, could you? Thanks. I'll feel more comfortable if you're naked too."

Mom told me to get some supplies. This almost seemed clinical, but in a very surreal, erotic way. Mom told me to get hand sanitizer, Sarah's lubricant, a box in the bathroom labeled "Winged Maxi Pads," a box labeled Tampons, and a diaper. "Oh, and get Sarah's brown, big, cotton granny panties in her top drawer and heat up a moist towel in the microwave." I didn't know what all this meant but I scurried around collecting everything Mom asked for. Mom and Sarah had undressed and were both naked when I returned. The two beautiful girls naked together caused my penis to stir in my panties. Sarah was laying naked on her back on the bed, legs right together. Mom was sitting off the side of the bed, her back to me.

Mom laid a towel on the bed saying, "Sometimes this causes her period to start."

Mom had me sit near the bottom of the bed to watch. Mom leaned down and kissed Sarah on the lips and Sarah put her arms around Mom's naked body pulling her in closer. Watching Mom and Sarah kiss always excited me but seeing them both nude kissing was even hotter to me. Mom sanitized her hands and said to me, "First, Tammy, I'm going to rub her belly, down low, her pubic region, over her mons and over both sides of her vagina, where her ovaries are located. Then I'll place this warm, moist towel over her belly. Now, Sarah, spread your legs. Tammy, you prepare the brown panties. Turn them inside out and lay them flat on the bed. Get a Maxi Pad and lay it on top and open the tabs and line her panties with the pad."

Sarah opened her legs and Mom placed her right hand on Sarah's shaved pussy and said, "Now I'm feeling her pussy, on the outside, to see if she's wet or if we need to use the lubricant that I bought for you two. I'm opening her lips, gently, just using my fingertips, opening her pussy just a bit, and feeling along the inside to see if she's lubricated with her own wetness."

Sarah looked plenty wet to me. I could see the glistening as Mom opened her pussy. I was hard in my panties, watching Mom and Sarah and Sarah started squirming on the bed. "Tammy, I know you have feelings for Sarah and don't want to see your friend cramping. At the same time, I know it's also exciting for you to see her like this." I tried to suppress how I was feeling and the feeling in my panties. Mom placed her left hand, palm down over Sarah's smooth pussy and used her thumb and fingers to spread her pussy wider, exposing her clitoris, like Sarah had shown me in the bathtub that day. She slipped two fingers from her right hand inside Sarah's wet pussy and slid them in and out. Sarah began panting and moaning and squirming on the bed, telling her Mom, "Oh, Mom, this feels soooo good. Please don't stop, Mom!" Mom used her thumb on Sarah's clitoris and Sarah's knee-jerk reaction was to try to close her legs. She relaxed again and Mom pushed her legs down and resumed masturbating her.

I couldn't stand being so hard like this and leaking profusely into my panty. Mom asked me, "How are you feeling, Tammy? Do you like seeing Mommy and Sarah naked like this? Do you want to learn how to masturbate our pussies and make us cum...to make us orgasm...like I'm doing for Sarah?"

"Omg, Mom! Yes. I'm so excited and turned on."

"Kneel on the floor between my legs, Tammy. You can put your finger in Mommy's pussy."

Mom spread her legs. The room smelled of the women's sex and their hot pussies. Mom said, "Lightly, like you saw me do for Sarah. If it feels wet to you, slip your finger in." I kneeled between Mom's legs and looked up at her beautiful naked body.

I slipped my index finger along the wet folds of her pussy and slid one inside. Then two fingers. "Mom, you smell so good. You're so soft and slippery."

"Yes. Sweetie, but remember, Sissies never go near a woman's pussy with their penises. Sissies masturbate."

Both Mom and Sarah were moaning together and climaxed. I ejaculated in my panties. Mom said, "Suck your fingers, Tammy. Taste Mommy's pussy."

Mom pushed a Tampon into Sarah's pussy.

Alice64
Alice64
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chefjess2039chefjess20394 months ago

You say this a wonderful story about friendship and love. Maybe I am reading a different story because all I see is a mom that's a sexual predator that is grooming her daughter to be just like her and taking a naive boy and mentally and physically abusing him

SissyBoy1WarszawaSissyBoy1Warszawaabout 1 year ago

A wonderful story that shows the realness of feelings, friendship and love, and shows the full emotions in each of the characters, both in Tammy, Sarah and Mom.

I really like the step by step change, training Tommy-Tammy into a sissy dedicated to Sara and her Mom. You wonderfully portrayed the state during a girl's period and how his emotional state can change during his period, and you beautifully described how Mom masturbated to Sara and how Tammy caressed Mom at the same time.

You write wonderfully and I am already looking forward to more experiences and changes in Sissy Tammy with great anticipation and curiosity. I grew very attached to the character of Tommy-Tammy.

Regards SissyBoy from Warsaw, Poland. 📝👩‍🦱❤️👧❤️👩‍🦳🧒❤️👩‍👧‍👧

Wspaniała historia, ukazująca prawdziwość uczuć, przyjaźni i miłości, oraz pokazuje pełne emocji w każdym z bohaterów, zarówno w Tammy, Sarze i Mamie. Bardzo podoba się Mi krok po kroku zmienianie, szkolenie Tomego-Tammy w sissy oddanej Sarze i jej Mamie. Cudownie przedstawiłaś stan podczas okresu dziewczyny i jak może zmieniać się podczas jego stan emocjonalny, i pięknie opisałaś masturbację Sary przez Mamę oraz jak Tammy w tym samym czasie pieściła mamę. Cudownie piszesz i już z wielką niecierpliwością i ciekawością czekam na kolejne doświadczenia i zmiany w Sissy Tammy. Bardzo się zżyłem z postacią Tomego-Tammy.

Pozdrawiam SissyBoy z Warszawy, Polska. 📝👩‍🦱❤️👧❤️👩‍🦳🧒❤️👩‍👧‍👧

AnonymousAnonymousabout 1 year ago

Love the story! I like the dynamic between Sarah and her mother. I know that Tammy was told she would never have sex with either of them, but I'm kinda hoping that they stay a trio, and Sarah and her mother start to have deeper feelings for Tammy. Well anyway, love your writing style and I look forward to the next chapter.

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