A Sissy for Sarah

I cleared the tears from my eyes and was glad Mrs. Carter wasn't judging me or Sarah and seemed to want to help us. We both nodded "yes."

Mrs. Cater started again. "Ok. Now let's discuss Tommy's behavior. Be honest, Tommy, do you feel better wearing girl's clothes? Sarah's clothes?"

I was embarrassed but tried to answer her honestly. "I guess so."

"You guess so or you do? Let me ask it this way. Do you wish you were wearing Sarah's dress right now?"

"Oh, Mrs. Carter, I'm sorry...yes, but not in front of you, the way you caught us."

"There's no need to be sorry, Tommy. I just wanted you to admit it so I could offer you something. If you accept my offer, I'll be seeing a lot more of you in dresses. You had a very loving but sheltered life with your Mother, Tommy, and never had the opportunity to explore your own sexuality. She kept you safe and protected you from everything. I'm sure she would not approve of what I'm about to say, but you're 19 now and old enough to make making your own choices and decisions. Tommy, if we kept this private between the 3 of us, how would like to be able to dress feminine while you're at home with Sarah and me?"

"Oh, my! Really? I mean, you'd let me do that? You'd be ok with that? And you wouldn't make fun of me?"

"I wouldn't have offered it to you if I wasn't serious. No, Tammy, (the first time I heard her call me this) we won't make fun of you, but you may feel self-conscious and embarrassed sometimes. But I think that would be a natural reaction for you. After all you'll be a Sissy now, Tammy, and your relationship will change with Sarah and with me. You're a boy wanting to live as a crossdressing girl with two women. You have a penis and no breasts and will be wearing panties every day. We'll be calling you our little Sissy. It's only natural that we will tease and embarrass you about this, Honey. If you want this, you'll have to be prepared for that, Sweetie. You will be a Sissy girlfriend to Sarah and no longer her former neighborhood boyhood friend. She's starting to date boys now. You'll be staying home in your dresses and pretty panties. You want to wear Sarah's dresses, panties and bras. I'm sure Sarah will tease you about that. Sarah will be in charge of the household when I'm not home, even though she is younger than you. You'll take orders and directions from her. Sarah will be strict with you. Sissies can become very needy and whiny. I'm giving her permission to use my hairbrush if she feels it's called for. Do you think you can accept all of this? Sarah, you don't have a problem with this do you?"

"No, Mom, I'd love it, if Tammy (now Sarah used it too!) could be out in the open about this with us. I can give her some of my old dresses and panties, Mom, unless you have other plans for him. I know he likes my clothes though. And I'm ok with spanking Tammy if she needs it too."

I cringed at the thought of my friend, Sarah spanking me. I told her, "I hope that won't be necessary, Sarah. I would feel humiliated having to take a spanking from you or your Mom." Sarah and her Mom smiled at each other.

Her Mom said to Sarah, "Yes, you can give her a few of your things, your older dresses and some of your panties and your smaller old bras. And we can go through my closets and drawers too. Of course, we'll have to get her some new things too. Her own nylons and hosiery and heels. If she's being ornery or disrespectful to you, have her bend over the back of the couch, take her panties down and give her about 10 good smacks on her bare bottom, Honey, like I do to you. I know it may be hard for you to spank your friend, but Tammy is a Sissy now and will need to learn discipline and proper behavior. If you don't redden her bottom, she will think you are just playing. If she cries it's ok, Honey. Don't let her tears stop you from finishing her punishment. And don't let her wiggle her bottom until you are through. You can teach Tammy to wash and dry your hair and shave you, armpits, legs and pussy. You can allow Sissy to masturbate if you watch her, but I don't want her going down on you if I'm not home to watch her with you. Are these rules clear to both of you?"

Sarah told her Mom, "Yes, Mom and I'm sure Tammy understands. I know she feels nervous and embarrassed right now, don't you, Tammy?"

I nodded my bowed head in agreement with her. Now her Mom turned to me. "Tammy, I still didn't hear you say, 'yes' yet."

"Oh, my, yes, Mrs. Carter. I'd love to dress in feminine clothes at home!"

"Ok, you'll still have your same bedroom downstairs. We can do some things to make it more feminine for you. Pink sheets and bedspread. Flowers. A teddy bear. We'll get started tomorrow night on a few other things after dinner, picking out clothes, learning how to dress, you know, stuff like that. We can progress slowly, but I don't want you changing back and forth between male and female clothes at home. Once you commit to this you will only wear female clothes at home and to sleep in. You won't have any male underpants here anymore. You can wear panties to school. If you ever go back to male clothes, with certain exceptions, here at my home, I'll take that as a threat to Sarah's virginity and have you find another place to live. Do you understand me, Tammy?"

"Yes, Mrs. Carter."

"Tammy, I want to make sure you understand. This means after school you'll be changing into a dress or skirt, bra, panties, hosiery or pantyhose, and heels. No pants will be allowed. There will be few exceptions to this rule. This won't be playtime. You'll keep your body and legs free of all hair, including your penis and balls. You'll remain dressed throughout the weekends and keep up your grades in school. You'll keep up on your chores. I will expect ladylike behavior from you. You and Sarah can study together...as two girls. I will allow you to be in her room as long as you remain dressed, and the door is left open. You won't be dating, but if Sarah has a date, there can be no jealousy and you can help her dress for her dates. If she brings a boy home, you will remain in your basement room. There can be no jealousy about her dating. You should be happy for her. After a date, she can tell you about it while you masturbate. No going in our rooms without our permission. Are we clear on all this?"

"Yes, Mrs. Carter. I understand."

"And you want to make this choice, is that correct?"

"Yes, Mrs. Carter, I really do. And thank you so much."

"Sarah, you're good with all this?"

"Yes, Mom! I didn't really understand him wanting to wear my dresses, but I understand more now, and that my friend Tammy is a Sissy. You made it clearer now and I know things won't be the same, but I think Tammy will be happier now."

"Good. We are all agreed."

There was a momentary pause and then Mrs. Carter told us, "Now since you two have never really seen each other naked, a good place to start is in the bathroom. I'm going to have you two take a bath together."

Sarah called back, "Mom, you can't be serious!"

"Of course, I'm serious. You two have been mollycoddled for all your lives. Look what you've both been doing behind my back! Tammy wearing dresses and panties. Sarah, you showing him your pussy! No knowledge about sex or relations. Sneaking around, covering up things. Tammy's mother and I never gave you two anatomy or health classes. We never had the sex talks with you, and we should have, so I'll do it now. I would rather have you do this with me watching rather than sneaking off together. You can ask questions and learn things that you never knew. It will fulfill your curiosity and we can be out in the open about this. Besides, I don't believe from what I've learned about Tammy, that she's interested in intercourse, so I'm not worried about her being naked with you. And you will see her when we help her dress anyway. Now Tammy can see you nude as well. Let's go upstairs and get the bath water running."

I couldn't believe this was happening. Just from me wearing one of Sarah's dresses and it turned into all this. Now Mrs. Carter wants us to bathe together! And I just accepted that I will be living here, femininely from now on. Sarah has been my best friend all my life. But I've never been naked with her. I was excited but nervous. Sarah probably was too!

Mrs. Carter stopped in Sarah's bedroom and came back with two panties. "We may as well start Tammy on her panties after your bath," she said. Mrs. Carter started the bath water and poured in bubble bath. She was still smartly dressed in her business work attire, burgundy blouse, black medium length skirt and black hose. She had already taken her heels off downstairs. "Both of you can get undressed now," she told us. We both looked at each other and didn't know how to respond. But Mrs. Cater was serious and the bath water was running. We turned around but Mrs. Carter demanded, "No. There's no need to be modest about this! There's nothing to be ashamed about. Nudity is perfectly natural. Face each other and take your clothes off. Both of you now! I expect you both to respect me and follow orders. I'm doing this for you both!" Sarah and I had been friends for so long. But this was different now. We had never seen each other totally naked before and now we were going to do it in front of her Mom!

We took our socks off and then I took my shirt off and Sarah took off hers. Mrs. Carter quickly commented, "Tammy, look at her cute toes and painted toenails. You said you were attracted to them and even sucked her little toes." Her Mom then went behind Sarah and unclasped her bra, as if all this was very normal, and I saw Sarah's tits for the first time. They were small, round and looked firm, sitting up high on her chest. Her nipples were sticking out. Mrs. Carter said, cupping Sarah's tits, "Sarah is late bloomer and still blossoming, but aren't her breasts so cute, Tammy? She's small, 32B, so I think her bras will fit you. I measure her for her bra size every month. She's grown a cup size in the last few months! Don't you just love her dark brown nipples?"

I said, "She's beautiful, Mrs. Carter. You know I've always thought your daughter was very cute."

"Finish undressing and you can touch her breasts in the tub. I want you to massage her nipples. Has any man ever touched your breasts, Sarah?"

"One date felt me up a little. Just on the outside of my clothes."

"Once we have Tammy adjusted to her new lifestyle with us, we can have her suck your titties, too."

We both took our pants down at the same time which left us in our underpants. Sarah, of course, had panties on. We hesitated, looking at each other. Sarah's mom said, "Come on you two. Take them off. The bath water is almost full!"

Sarah pulled her panties down first and stepped out of them. I had to take mine down over my erection. Mrs. Carter said, "Look at you two! Two best friends! How does it feel to be naked together now? Look at Tammy's cute, little hard penis, Sarah!" Mrs. Carter shut the water off and said, "Before you both get in, give each other a little friendship kiss on the lips."

I couldn't believe this was happening to me. Standing naked with my best friend, Sarah, in the bathroom, with her Mom telling me to give my friend a kiss. We stepped up close and brought our puckered lips together for a quick peck. Mrs. Carter grabbed her phone and took pictures of us, naked and kissing! "Don't worry," she said. "These pictures are just for us. We can look at them later together. You two look adorable. Hold hands and face me for another pic."

Mrs. Carter said, "That's so cute you two! So sweet! You both look adorable naked together. Tammy, I want you to notice that Sarah is clean shaven." Turning to Sarah she said, "Spread your legs, Honey and show him." Sarah spread her stance. Her mom said, "All her pubic hair has been removed. I wax her myself. I believe in cleanliness and good hygiene, and I think this keeps her pussy cleaner. You'll need to be shaved clean down there too, Tammy. Even your balls. It's a much more feminine and a cute look for a Sissy. I hope you don't mind me referring to you as a Sissy now. That's how Sarah and I think of you now."

"No, I don't mind. I think I kinda like it. I've always felt a little different from other boys and confused about my sexuality. Maybe I've always been a Sissy and hearing you tell me what I've been helps me come to terms with it. I already know now that I don't want to use my penis for intercourse."

"That's good, Tammy. I didn't think you would. That's why I'm not concerned with you being naked with Sarah. I want you to remain a virgin while you're living with us. And hopefully you'll carry that forward and remain a virgin for the rest of your life. I think it would be best for you if you never entered a woman's pussy with your penis. I do think as a Sissy you'll enjoy giving Sarah cunnilingus."

"I've never heard that word, Mrs. Carter. What does it mean?"

"It means giving oral pleasure to Sarah's pussy, using your mouth, lips and tongue on her down there."

I blushed but had to agree with her. "Yes, Mrs. Carter, I told Sarah once that I wanted to kiss her there."

"Tammy, kneel in front of Sarah so you can smell her sex. Her natural scent, instead of from her panties."

I nervously kneeled in front of Sarah and smelled her pussy. Sarah blushed and closed her legs together. Her Mom told her to open them. "Sarah, open your pussy to let your scent flow for Tammy. Tammy, give Sarah's pussy a little kiss. You said you wanted to kiss her down there."

Omg, I was kneeling in front of Sarah, my best friend, both of us naked, her own Mom telling us what to do and taking pictures of us. I smelled Sarah's pussy and kissed her there, her mons area, right above her pussy; so soft and smooth.

"Doesn't she smell nice Tammy? She keeps her pussy very clean. I douche her once a week and after her periods. A period is about 5-7 days of menstrual flow. She bleeds from her pussy, Tammy. It's perfectly normal. She wears pads in her panties during this time. You can wear pads in yours too when she's having her period to feel in close contact to her."

Mrs. Carter asked Sarah, "Would you like to tell Tammy about your enemas, or should I? She will be taking them too now."

Sarah felt embarrassed but thought she should be the one to tell me. "Mom gives me an enema once a month. It's to clean me out if you know what I mean. She wears rubber gloves and gives me a suppository the night before. It's like a little pill she puts in my rectum. She pushes it pretty far up. Then we have to wear a ladies panty diaper to go to sleep, just in case. But nothing else, just the diaper, so we're ready in the morning. By morning I really need to go. The suppository makes the enema easier. After I've pooped, I get the enema. I'm naked in the bathtub on all fours, Tammy. It's a little humiliating, but Mom says the enema is healthy and good for me. She has an enema bag on a stand, and it usually has warm water in it. Sometimes you get a coffee enema. There's a nozzle that gets inserted and you hold the liquid as long as you can. I don't know, I think it's like one or quarts. She's gentle. She uses some kind of stuff to make it slippery when she inserts it, like a jelly or something. Sometimes some comes out if you get too full and can't hold it. That's why you have to naked and in the bathtub. Sometimes she repeats it 1 or 2 more times. She wants to see clear water coming out. When it's over we wear the panty diaper again until Mom says it's clean. You'll be a little sore back there the next day. It's really not that bad, Tammy. We can do them together."

All the while Sarah explained it, we were both still standing naked facing each other while her Mother observed us.

Mrs. Carter said, "You explained it well, Sarah. Tammy, you're going to like being a Sissy with us girls! Now Sarah, one more thing. You said you had never seen Tammy straight on, from the front. Take a good look now. Notice how his penis stands up straight, pushing out from his body? It's his sex organ---a hard-on, or erection, but we will call it his boner. It's a little more juvenile term and fits for Tammy. His penis is very small, but a Sissy usually is. He has a little penis, Honey, never a cock. Real men have a cock. You'll have bigger men in your life, Sarah. Hopefully, you marry a very loving man with a big cock. If you marry a Sissy like Tammy, you'll only get oral.

"Oh, Mom, I don't know how intercourse feels or oral sex. But I think Tammy would love me and make me very happy, even with his little penis. Especially if he lived with me as a Sissy!"

"That's probably true, Sarah. But you would need another man to impregnant you for a baby."

Mrs. Carter talked to her daughter while I stood naked. "Sarah, when Tammy has a boner like this, it means she's ready for sex. Sex does not mean intercourse for Tammy which is why I want you to see it. Sex can mean any number of things to Tammy. It means she's excited and aroused. It may mean she's ready to give you oral sex. Or she desires to suck your toes. Honey, this may sound strange to you right now, but Tammy even may want to lick your anus, especially when she's wearing her girly clothes. I know it may be hard to believe that your friend would want to do this to you, but please try to understand that Tammy is a Sissy and it's perfectly normal that she would want to do this. Her boner may also indicate that she needs to be masturbated. Now, I want you to notice his cockhead, we'll call it her bulb. There is a very sensitive spot right on the underside of her bulb. If you touch her there and rub that spot for a few minutes she will ejaculate without ever really having to touch her penis. It's like you're rubbing her clit in that spot. A Sissy like Tammy should orgasm quickly like that."

Mrs. Carter asked us, "Do you two have any questions right now?"

Sarah asked her Mom, "Mom, you said my breasts are still growing. Will Tammy's penis get any bigger?"

"No," she said, "I'm afraid he won't get any bigger, Honey. He will always be diminutive."

Sarah asked, "What about his balls? I don't know too much about them."

"Good question, Sarah. Obviously, you see his little balls hanging down below his penis. It's his sex gland, called his scrotum. His scrotal sack or ball sack. They are his testicles. Another word is gonads. Semen, which contains sperm, is produced in his gonads. That's the fluid to get you pregnant. It comes up from his gonads and through his penis when he ejaculates. His gonads are very sensitive and can ache when he has repeated erections without ejaculating. I think Tammy's gonads are probably aching her right now. You can feel her gonads in the tub. Go ahead and both of you get in now, facing each other."

The warm water felt so good, but I still had a raging hard-on. We both tried to relax but being naked with each other wasn't helping us to relax much, especially in front of her Mom! Mrs. Carter said, "Tammy you can touch Sarah's tits now and Sarah, reach under the water and feel Tammy's gonads. Don't squeeze them. They can be very sensitive." We both reached out and touched each other. The sensations were incredible for both of us, never having done this before. Sarah called out to her mom, laughing a bit, "Mom, they feel like little peanuts."

Sarah's mom laughed, "Hahaha...that's cute, Honey. Yes, they are small and I'm sure Tammy won't mind you calling them her peanuts." Sarah's mom was smiling, and her hand was rubbing over her pubic area on the outside of her skirt. She continued to give us instructions. "Sarah, you can touch his penis and Tammy, you can feel her vagina." Her vagina felt wet, but not water-wet. It was more slippery, like oily is all I can say to describe it. We were both very sexually aroused.

Mrs. Carter told Sarah to stand up. "Show him how to find your clitoris, Sarah."