A Sissy for Sarah

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I was looking directly at Sarah's pussy. Sarah said, "I pull up here, it's the hood, and then it exposes my clitoris."

Her Mom said, "The only purpose of a woman's clitoris is to provide her with sexual pleasure, Tammy. That's where oral on her will really give her pleasure and powerful orgasms. Now do you see her labia? The flappy darker colored skin around the opening to her pussy? That's her labia, or pussy lips. Touch them, Tammy. Feel them. It's ok. Don't be shy. I want you to explore my daughter's body. Put a finger in her hole---her pussy hole."

Sarah winced a bit when I slipped a finger in. "Does that hurt?," I asked her. "It's so warm and soft in there."

Sarah said, "No, it's just that no one has ever done that to me before. My Mom kinda does it a little bit when I'm taking my enema just to see if my pussy is wet. You kinda caught me off guard. But I like it, Tammy!"

Sarah sat back down in the tub. Sarah's Mom said we should soap and wash each other. We were both a little clumsy doing that and weren't sure what we were doing. Sarah's mom told us to stand up to wash each other's genitals. When we stood up, her Mom started snapping more pictures of us. Sarah was tentative when she touched me there and I've never had my penis touched so it was really quite exciting for both of us. Her mom told Sarah, "Don't be afraid to wash his little penis, Sarah. You may be bathing Tammy in the future and I want you to know how to wash her penis." I especially felt strange when Sarah washed me there in her hands! But she was so gentle with my peanuts! I loved it! I thought we were done until Sarah's Mom told us to stand up and face the wall opposite her. She said, "Both of you, bend over!" We were both embarrassed and as we bent over. Sarah's tits hung down. We heard her camera go off again with both of us in this humiliating position. She told us to spread our butt cheeks. The camera clicked again. Mrs. Carter slipped a soapy finger into both of our rectums at the same time! We both jerked forward. She told us to sit down and rinse it out. Sarah and I never said a word about that and neither did Mrs. Carter. But we knew she would bring it up again sometime.

Mrs. Carter gave us towels and we toweled off. We wrapped ourselves in the big towels she gave us, but we were both still naked. I still had my erection. Sarah's mom said, "Tammy is still hard, and she won't be comfortable in her panties like that. You're going to have to masturbate, Tammy. I know you haven't had much experience doing this so we can guide you through it. Most boys do this in private but we're all girls here now and I'm sure Sarah would like to watch. I don't want you masturbating in private. Come to me or Sarah and ask us if you can masturbate. I'm going to have Sarah oversee the household when I'm not here, so you listen to her and obey her. If I'm home you can come to me, but if you're home with Sarah, you will need her permission and only if she is able to supervise and watch you. Do you understand?"

"I'm feeling ashamed, but yes, Mrs. Carter, I understand."

"You can call me Mom like Sarah does. It will give us nice family feel."

"Ummmm....yes, Mom."

"Some men look at a girly magazine for arousal when they masturbate. You might like a gay magazine like you saw in the bookstore. We can get you some. Stand up and take your towel off."

I took off my towel and handed it to Sarah while she looked on intently. Sarah tossed my towel over the tub.

"Ok, Tammy, you can call this wanking, jerking-off, jacking-off or masturbating. There are other more derogatory terms but those four will be your only words for this in my house."

"Yes, Mom."

"I'm going to give you some hand lotion. It makes it smoother and saves you from chaffing. Sarah knows where we keep the petroleum jelly when she's home with you, or even kitchen vegetable oil is good for this."

I told her, "Mom, this is very embarrassing for me."

"Tammy, there's nothing to be embarrassed about. You just had a bath with my daughter. I know your peanuts are full, Sweetie. Think how nice your panties will feel after your soft and limp. Mommy is here with you and your best friend, Sarah. This is private here in our home. No one will ever know you wear girl's sissy clothes or masturbate in front of us. These are the urges you felt when you put on Sarah's dresses, but you couldn't do anything about them then. Now that we all know you're a Sissy, you don't have to hide it anymore and you can jack-off to relieve your tensions and sexual frustrations. We'd like you to show us how you humped your pillow that one time too. You can even wear a dress now when you jack-off if you want. I know that's what you're thinking when you wear one of Sarah's dresses. You don't have to have any secrets from Mommy and Sarah from now on. I know we'd love to see you hairless, in just a pair of sexy nylons, with a garter belt and high heels while you jack-off for us, wouldn't we Sarah?"

"Omg, Mom, that would be so hot! Could we really see him like that, Mom? Won't he be humiliated?"

"Of course, we can, Sarah. Just imagine how cute and sexy she will look when she's hairless with smooth skin and her little penis sticking out between her nyloned legs! Tammy needs control over her life. She needs authoritative figures in her life. You and I will be his dominants and Tammy will be submissive to us. Sarah, a Sissy needs this. I'm sorry to say this Sarah, it may be difficult for you to hear and see your friend like this, but you're going to need to humiliate Tammy sometimes. You're going to have to give her orders sometimes, like I'm doing for her now. Trust me, the humiliation excites her."

It's not like I wasn't in the room. I could hear everything they were saying to each other. I bowed my head feeling my shame. But my penis was as hard as it has ever been, and my peanuts were aching. I held out my hand and Mom put the lotion in my hand. "Mom, will my peanuts stop hurting after this?"

"Yes, Honey, they will. I promise."

I asked Sarah, "Do you think I should do this?"

"Yes, Tammy, Mom says you should. Just listen to her."

Mom smiled and squirted the lotion in my hand, and said, "Good girl." She told Sarah to take her towel off and stand naked so I could look at her and said to me, "I know this is still embarrassing for you, but I promise you that you don't need to feel ashamed with us. We understand you now, Tammy, and only want to help. I have your panties all ready for you here as soon as your finished. Just use the lotion and start playing with yourself. Go ahead. There's nothing to feel guilty about. Mommy and Sarah are here for you."

Mom turned my shoulders to face the big full-length mirror in the bathroom. I put my hand on my penis and began rubbing it while Sarah and her Mom watched. Sarah was fascinated as I pulled myself back and forth with my thumb and index finger.

Mom said, "That's right, Sweetie. You look so cute, Honey. Look at yourself in the mirror. Use your finger and rub your bulb a little with the lotion. That's right, Sweetie, don't feel embarrassed. Show Sarah."

Sarah stood and watched in awe as I circled my bulb with my finger. Sarah's Mom took another picture of me playing with my penis.

Then her Mom said to me, "There's a very natural motion that will make you feel very good, Tammy. Wrap your hand around your penis and pump it, loosely in your hand, a nice, steady in and out, back and forth stroking motion. Make your grip tighter or looser as you need it. Massage your peanuts with your other hand. Go ahead and push your hips in and out. Look at Sarah, Tammy. Look how pretty she is, standing here naked for you. Look at her soft little tits. Imagine if she had a limp little penis hanging down between her legs that you could look at."

Sarah yelled, "Mom!"

"It's ok Sarah. It's good for Tammy to imagine these mental images in her mind."

"Does that mean Tammy is gay?," Sarah asked her mother.

"Not necessarily, Honey, but she already admitted she fantasizes about male cocks and would like to suck them."

My head was spinning. My mind quickly brought up an image of Sarah with a penis! I couldn't help thinking that would look good to me too!

Mom said, "It's ok, Tammy. Just look at Sarah now while you wank."

Both Sarah and her mom were focused on my fist pumping and watching me masturbate. Mom flashed more pictures of me. Under my heavy breathing, I let out, "Ohhhh, this feels soooo good!"

Mom said, "I know it does, Sweetie. Take your time. Make it last. I'm so proud of you."

Sarah's mouth was open, sort of half smiling, mesmerized, half giggling at me.

I called out, "You promised you wouldn't make fun of me or laugh at me!"

Mom said, "Oh, Sweetie, we're not laughing at you. Sarah has just never seen a man masturbate before. She's excited seeing her Sissy best friend naked in her bathroom jacking-off in front of her. You'll get used to us watching. And you'll get to watch Sarah masturbate too. And we'll teach you how to lick her pussy."

Mom put her hands on my shoulders again and said, "Turn now and look right at your best friend Sarah. Show her how much you like to jack-off while looking at her naked. Like the way you looked at her pussy while wearing her dress. You liked putting her dresses on and having Sarah show you her pussy, didn't you? She's right here for you now. And so is Mommy. You've always wanted to do this for Sarah. Look how pretty she is for you. Show Sarah and Mommy how you ejaculate!"

That put me over the edge, and I screamed out some kind of girly Sissy scream and ejaculated all over Sarah's thighs, running down onto her legs and the bathroom floor. Sarah said, "Omg, Tammy!"

Mom put her arm around me and said, "Tammy, you're going to be a wonderful Sissy around here. Let's get your little limp penis and little peanuts into nice soft panties and a nightgown now. You can jack-off for us again tomorrow."

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7 Comments
bottomfunbottomfun12 months ago

Such a fantastic story, I was so drawn in from start to finish, it was so very erotic, such a huge turn on!

itsnotjustmeitsnotjustmeabout 1 year ago

Another awesome story. You have a great imagination and do a great job of bringing it to life in your stories.

someonesGoodBoysomeonesGoodBoyabout 1 year ago

HOLY SHIT THAT WAS AMAZING!!

SissyBoy1WarszawaSissyBoy1Warszawaabout 1 year ago

A wonderful story of friendship and even more between Sara and Tom-Tammy, the wonderful acceptance of their friendship by the mother and even taking care of Tom-Tammy. Sarah's mom also opens up their erotic world, showing their naked bodies to each other, and Tommy becomes Tammy. I would like to have such a mother who will love me and train me as a Sissy for her daughter Sara. Thank you for showing me faith in true love, friendship and acceptance of other people. SissyBoy from Warsaw (Poland). 💕📝

Wspaniała historia przyjaźni a nawet czegoś więcej pomiędzy Sarą i Tomem-Tammy, cudowne przyjęcie przez mamę ich przyjaźni, a nawet podjęcie się opieki nad Tomem-Tammy. Mama Sary również otwiera ich świat erotyczny, ukazanie ich gołych ciał sobie, a Tommy staje się Tammy. Sam bym chciał mieć taką mamę która będzie Mnie kochać i szkolić na Sissy dla swojej córki Sary. Dziękuję za ukazanie Mi wiary w prawdziwą miłość, przyjaźń oraz akceptację inność innych osób. SissyBoy z Warszawy (Polska). 💕📝

AnonymousAnonymousabout 1 year ago

A really wonderful story,so full of love.

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