A Sissy for Sarah Pt. 02

Story Info
Mom continues our education.
6.4k words
4.71
21.9k
26

Part 2 of the 4 part series

Updated 06/16/2023
Created 03/21/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Alice64
Alice64
263 Followers

The next day I began dressing. Sarah and Mom were so helpful to me in adjusting and adapting to this new lifestyle. They both gave me some of their clothes and helped me set up my closet and drawers and feminize my bedroom. Sarah even gave me one of her old dolls to put on my bed. Mom took all my male underpants except for one that she took and put away just in case. We shopped for some things I would need like more panties (some really cute ones!) pantyhose, stockings, a garter belt and shoes. Mom got my ears pierced at the mall. We even stopped at the bookstore. Sarah and Mom browsed books and Mom told me, "Go pick out a gay magazine you like. I'll buy it for you."

It was embarrassing for me, especially when I put the magazine on the counter and a young girl looked at it, looked at me, and rang it up. When she saw Mom pay for it, she started laughing a little. They started me on low 2'" chunky heels just to start getting used to wearing ladies' shoes. It was strange feeling my weight shift forward in the shoes. Mom told me to practice as often as possible. "Stand and walk in them as often as possible, Tammy. I want to move you up to 3" spiked heels soon. They will be harder for you to walk in at first but I think that will be a good height for you and make your calves and legs look sexy in your nylons."

Sarah and Mom taught me how to put my stockings on, by pointing my toes close together and down, rolling the stocking up and then to gently guide them up my legs. They taught me to be careful not to put runs in them, but how I could fix small runs with clear nail polish. They showed me how to attach my garter belt to my stockings. And showed me how to lift my dress and sit down when using the toilet. Mom showed me how to put lipstick on the proper way and they taught me how to hand wash my delicates.

That first 2 days, after Sarah and I came home from school, she would go to her bedroom, and I would go to my basement bedroom and change clothes. Then we would go to the kitchen for a snack or start our homework and studying together either at the kitchen table or in the family room. Sarah acted normally around me, even in girly clothes. I was Tommy during the day but as soon as I came up the stairs, I was Tammy. Sometimes both Sarah and her Mom would just call me Sissy. When Mom would get home from work, we would all do dinner. I was responsible for setting the table and doing all the dishes after dinner. They were teaching me to cook too. They both acted like everything was perfectly normal, even though I was now wearing all female clothes.

The next day, Sarah called and told her Mom she would be running late as she had to do some work at the library. Mom said to me, "This will be a good time to get you shaved, Tammy. Let's go to my bathroom." Mom took my hand and led me up the stairs. "Get undressed Tammy. We have to do this in the tub."

"Everything, Mom?"

"Yes. Everything."

"But I have a boner, Mom."

"Tammy, I'm sure you do but I've seen you naked before."

I took my blouse and bra off and lowered my skirt.

"Panties and stockings too, Sweetie. Stand in the tub."

I got in the tub, still hard in front of Mom. She ran some warm water and let the tub fill a bit. She got her razor and some shaving gel. I thought she was going to start but instead Mom started to get undressed.

Nervously, I asked her, "Mom, what are you doing?"

"I don't want to get my clothes wet Tammy. Don't worry. It's ok now for you to see me naked too."

Mom took all her clothes off and came towards me in the tub. I don't know if I've mentioned how pretty and sexy Mom is. She's about 38 years old with a great body, big tits, pretty face and sexy feet! I put my head down.

"Tammy, don't be nervous. It's ok to look at me. Sarah and I have talked about it. Do you like Mommy's tits, Tammy?"

Mom looked wonderful. She was shaved smooth, just like Sarah. Mom's tits were bigger than Sarah's. They looked twice as big to me. When she turned around to get towels, I saw her perfect bottom too. I couldn't see between her legs. Only the part above her pussy. I was surprised to see a butterfly tattoo on her right hip and a rose tattooed on her left hip. "Yes, Mom, your tits...your body is beautiful."

She stood naked next to me in the tub and told me to lift my arms up high. She rubbed some feminine, floral smelling shave gel on my armpits and around my penis. She left the gel around my penis while she used her razor to shave off all my hair under each arm. Then she kneeled next to me in the tub and looked me over. I don't really have any chest hair, just a few hairs around my nipples. Mom got her tweezers out and plucked my nipple hairs. It stung a little. She gave me lotion to put on my nipples afterwards. "Honey, the hair on your legs is so light and soft I think we can just use a depilatory cream on them. We just apply it, leave it on for about 10 minutes and your hair will rinse away in the shower. And we'll do that for your peanuts too." She went to get the cream and I waited in the tub. She rubbed the cream all over my legs and then said, "Spread your legs and I'll do your peanuts."

My penis was so hard when Mom started to rub the cream on my peanuts. Other than Sarah in the bathtub, no one has ever touched my gonads before. I had an involuntary reaction to her touch and instantly ejaculated in the tub. I stood there, ashamed, perfectly still, as Mom watched, as my semen spurted 4 times and then dribbled out. I nearly started to cry. Mom said, "Oh, Tammy it's ok, Honey. That happens sometimes. Especially when you haven't jacked-off in awhile."

"Mom, it's just that seeing you naked and you touching my peanuts, I was too excited and couldn't stop it."

"It's natural for you to be excited seeing Mommy naked. I know it embarrasses you, but I don't have to tell Sarah about this if you don't want me to. We can just keep this shaving time between us, and she will see how smooth you are next time you jack-off. Ok, Tammy?"

"Yes, Mom."

"Now let me just finish shaving you and you can get in the shower and rinse off."

Mom shaved all around my penis and shaved away all my hair. I looked younger and more sissyish than ever. I rinsed off in the shower and my leg hair fell away. Mom checked my peanuts and leg hair to see if it had all been removed. We both redressed and went back downstairs. Sarah was just getting home. We didn't say anything to her.

Finally, it was Saturday and Sarah and I were doing our chores. Mom went grocery shopping. Sarah made me vacuum. She wanted to see me like a little housewife pushing around the sweeper. We took a break and sat down to talk. She asked me how I felt about that day in the bath with her. We hadn't talked about it before. I told her, "I know we were both embarrassed, but I was so excited, finally seeing you naked. I loved taking a bath with you. You're still my best friend, Sarah."

Sarah said, "I liked it too, Tammy. Especially the part at the end, you know, watching you do that." I blushed. "Tammy, I have something to tell you. Mom said not to tell you or anyone about this but you're my best friend, Tammy. And you can't say anything about this to anyone either. That night after you went to bed, Mom came in my room. She asked me if I was excited about my bath with you and watching you jack-off. I told her that I was. Mom pulled down the covers on my bed and then took off her nightgown. She was naked underneath. She told me to take off mine. I didn't have anything on underneath either. She laid down next to me in bed and started circling my breasts with her fingers and talking to me. She said girls have urges and get frustrated too and told me to just relax and close my eyes. She started touching me, you know, down there. She put her fingers on my pussy and told me to spread my legs. She played with my clitoris and fingered me. Mom said I was so wet. I had my first orgasm ever. I felt so good I started crying and I rolled over into my Mom's naked body, and I started sucking one of her tits, Tammy! I don't think she went up far enough to break my hymen so I'm still a virgin like you, Tammy. She said she's going to masturbate me again in front of you while you jack-off, Tammy. I don't know when, but she was serious, Tammy."

I was shocked by what Sarah just told me, but I had to tell her something too. "Sarah, I have something to tell you too. Mom took me upstairs to shave me and she took off all her clothes to do it."

Sarah said, "I think that's ok, Tammy. You're probably going to see us running around the house naked sometimes anyway."

That night at dinner I couldn't help thinking about what Sarah had just told me. I felt very frustrated and fidgety in my chair. Mom noticed and started asking me questions during dinner. "Tammy, are you adjusting, ok? How do you like wearing your new feminine clothes now? Have you been looking at your magazine?"

"Everything is good, Mom," I lied. "I like my clothes and being able to wear them now. I look at my magazine before bed."

"Tammy, you seem so squirmy. Have you been tingly in your panties? Do you peanuts hurt? You haven't asked about jacking-off. Do you have your boner now? Sarah and I are worried about you. Are you ready to do that again?"

"Oh, Mom!"

"Tammy, I have to ask you questions. You know that."

"I guess I've been kinda ready, since the first day in my new clothes, but it's so embarrassing for me."

"I know it is, Honey. But the more you do it, the easier it will be for you. Sarah and I won't have to ask you and can just tell us you want to do it."

"Mom, could I go do it by myself?"

"You know you can't, Tammy. We've talked about this. You've been hiding things from Sarah and me. Going into our bedrooms. You were wearing Sarah's dresses. You have to be supervised. Do you want to just go upstairs to the bathroom in private with Mommy this time?"

"Could I, Mom?"

"Tammy, I want you go talk to Sarah and tell her you want to do it with just Mommy this time. Tell her you need to jack-off and Mommy is going to watch you. Then I'll take you upstairs."

"Oh, Mom! Do I really have to tell her?"

"Yes, Tammy, you do. She will understand that you want to just be alone with Mommy."

I went over to talk to Sarah. I whispered to her, but Mom said, "Say it out loud, Tammy. You don't have to be ashamed to tell Sarah or me anything."

"Sarah, Mom said it would be okay for me to just go upstairs with her this time."

Tell her why, Tammy.

"I...I...I need to jack-off."

Sarah said, "You know, I could just say I'm coming too. I have that privilege. But I won't this time. I heard Mom say you could do it privately, just with her. I know this is still embarrassing for you, but Mom says you have to do it, so it's ok, Tammy. Go with Mom."

Mom took me by the hand, and we went upstairs. Even though Sarah already knew, Mom called back to her, "I'm taking Tammy upstairs for a few minutes," just to embarrass me more. She stopped at the laundry room. "Tammy, get two dirty panties, one of Sarah's and one of mine. You can use them this time. One to smell and one to ejaculate in." We went into Mom's bathroom and she shut the door.

"Tammy, you're going to need to take your dress off, Hon. Turn around and I'll unzip you." When my dress was off Mom noticed how I was dressed underneath. "Oh, Tammy, it's nice to see you're wearing your garter belt with your stockings. And such cute little lace panties! Do you want Mommy to take your panties down for you?"

"Mom, this is so embarrassing!"

"Don't be embarrassed, Sweetie. It's just Mommy here for you. All private in my bathroom, just like you wanted. Let Mommy take your panties down for you. You don't have to take them all the way off, just down around your thighs."

"Ok, Mom."

She took my panties down to my thighs. My penis sprang out and wiggled. She handed me both panties. Mom sat down on a stool at her vanity table while I remained standing.

"Go ahead and smell the panties, Honey. Decide who's you want to smell and who's you want to jack-off into."

I felt funny in front of Mom with my penis out and my panties pulled down and smelling their panties. I smelled them both. Mom watched me and said, "Turn them inside out. Smell the middle, the gusset of the panty. That's where our pussies sit on the panty." I did what she said.

"I'd like to keep smelling this one, the pink one."

"Ok. Those are mine. You like how Mommy smells?"

"Oh, yes!"

"Lick my panties, the gusset, Tammy." I was so hot I didn't question it. I licked where Mommy's pussy touched the panty.

"And you want to wank in Sarah's?"

"Oh, yes....please."

"Please what?"

"Mom, I feel so ashamed, but please may I wank in Sarah's panties?"

"Tammy, you don't need to feel ashamed with me. I let you do this privately with me so you wouldn't be embarrassed. No one ever needs to know you smell our panties in my bathroom and jack-off with me. Except Sarah of course. You used to sneak my panties and smell them. Now I'm letting you. Put Sarah's panties around your penis, Tammy. Rub your peanuts with Sarah's panties. Go ahead and jack-off in them. You can ejaculate in Sarah's panties while you smell mine."

"Oh, Mommy, I can't stop. I'm going to do it! In Sarah's panties!" I ejaculated and nearly fell over.

"Tammy, I want you to do something very special for me right now. You don't have to tell Sarah about this...lick Sarah's panties."

"But Mom, they have my semen in them."

"I know. I want you to taste it."

"I don't think I can."

"Yes, you can. You don't have to lick them clean. Just get a nice, big taste in your mouth, stick out your tongue and show it to me and swallow it."

I licked Sarah's panty and got a big glob in my mouth. I showed it to Mom and swallowed it.

Mom said, "I knew you could." I know Mom was laughing at me under her smile. She took my hand over to the sink and handed me a washcloth. "Clean your penis, Tammy. Put a little lotion on it after."

When I was done, Mom told me to take my panties off. And leave my dress off. I didn't understand. "Why Mom?"

"I want Sarah to see you limp, so she knows you've finished. Now give me a little kiss, Tammy and say thank you. Take my hand and we'll go downstairs."

I still had my garter belt, stockings, heels and bra on when we went back down to see Sarah. Mom took me over to Sarah and said, "Look Sarah!"

Sarah looked at my little limp penis and smiled as I hung my head. "Oh, Tammy, you did it with Mommy! And you're hairless now too. You look like Mom and me except for your little penis."

Mom smacked me on my bare bottom and laughed as she told Sarah, "Sissy did it in your panties!" We all changed into nightgowns and watched TV together that evening.

Maybe I hadn't noticed before, but it seemed to me that Mom and Sarah were getting closer together. I started noticing them doing little kisses while we all made dinner. It seemed innocent but I never noticed it before recently. Then the kisses grew longer and looked to be more passionate between them. I couldn't stop thinking about what Sarah had told me about that night with her Mom. I would see Mom pat her bottom or grab Sarah's ass while walking through the house. Once at dinner I dropped my spoon. As I went down for it, I saw Mom's hand rubbing Sarah's thigh. Mom would put her feet in Sarah's lap while we all watched TV together and Sarah would massage Mom's feet. One night, while they were doing this, Sarah said, "Mom, why don't we have Tammy suck your toes?"

I felt my humiliation, but I loved Mom's pretty feet. She gets her toenails painted about every two weeks. Today they were pink, one of my favorite colors she wears. I couldn't say no anyway. I kneeled on the floor by the couch as Sarah held Mom's feet in her lap. Sarah said, "Go ahead, Tammy. Like you did to me." I licked the bottom of her soles up to her toes and kissed each toe, finally sucking each of her toes into my mouth. Mom smiled down at me and shifted her feet to give me better access. Sarah touched my cheek and said, "That's so sweet, Tammy."

The following week, we started back to school. Sarah and Mom were starting to demonstrate their dominance and power over me, living with them as a sissy. They often talked in secret together, or behind my back. I guess I was warned and knew it was coming, but some things still shocked me. On Monday, after school I put on my panties, a skirt with stay-up thigh high nylons, a bra and top. Sarah said to me, "Tammy, now that you're all shaved and smooth, I think it will be cute if Mom comes home from work and you're on your knees right inside the kitchen door as she opens it and sees you wanking. I want you naked for this. Take off all your clothes and kneel in front of the door where she comes in. When she comes in, I want her to see you naked and jacking-off. I want you to look up at her and tell Mommy you want to jack-off for her. Then I want you to ask her to please take off her shoes so you can ejaculate on her feet. You know you love her feet and her pretty, painted toenails, and she always wears nylons to work."

"Sarah, you can't be serious!"

"Oh, believe me, I am Tammy. I will be sitting at the kitchen table watching. Mom is going to be so surprised seeing our Sissy masturbating while waiting anxiously for Mommy to get home from work!"

"Sarah, that will be so humiliating for me!"

"You're a Sissy, Tammy, what do you expect? Mom and I haven't seen you naked since our bath day. Now take your clothes off and get ready. She should be here in about 10 minutes."

I hesitated. My younger best friend making me do this. Sarah said, "Obey me Tammy, or I'll tell Mom and get the hairbrush!"

I know I didn't want the hairbrush. Sarah told me how much that thing stings and hurts, and you can't even sit down. I started taking off my clothes and draping them over a kitchen chair. Sarah said, "Just leave your heels on, Tammy. That's all."

I was naked and put my heels back on facing away from Sarah. "Turn around for me, Tammy." I turned and faced Sarah. "That's adorable, Tammy. Your penis is so hard! Mom will be so surprised, but she will love this! Looks like you don't need any cream or jelly. You're leaking already. You can use that. Kneel by the door, about 5' back so she can get inside the door and keep yourself hard. When you hear the door open start jacking-off and ask her if she would please take off her shoes and if you can ejaculate on her toes."

"Oh, Sarah! Please don't make me do this!"

"Kneel down, Tammy."

I was so nervous and embarrassed. I heard Mom's key in the door and watched the door open. I began masturbating and looked up to see Mom's face. She smiled and said, "Oh, isn't this a nice surprise for me! Coming to terms with your sissyness! Naked and wanking for me! And wearing your pumps. I'm sure Sarah made you do this. I love this, Sarah!"

Once she was in the door, my voice quivered as I asked, "Mom, I wanted to jack-off for you. Would you please take your shoes off for me and let me jack-off on your pretty toes and feet?" Mom kicked off her 3" pumps and put her nyloned feet beneath my dripping penis.

Sarah called out, "Tammy, ask Mom if you can smell her shoes."

Sarah wanted to humiliate me even further. But my heart was racing, and my penis was twitching. I don't think I've ever been so excited. I was so nervous even thinking what if she said "no" now? I went ahead with what Sarah told me to do. "Mom, may I smell your shoes?" I didn't wait for an answer. I was too excited. Mom's shoes were still warm inside. I picked up each shoe, one at a time and inhaled the pungent scent. I sniffed inside the heel and the toes of each shoe. The leather combined with her foot scent gave her shoes a penetrating power over me. I heard Mom and Sarah giggling as they watched me degrade myself.

Alice64
Alice64
263 Followers
12