A Sissy for Sarah Pt. 04

(Please be sure to read previous chapters before proceeding.)

Mom and Sarah were still teaching me about becoming more feminine. Mom taught me how to sit properly. I never thought about it before but when wearing a skirt or dress, you can't just plop down, the way I did as a boy in pants. She showed me how to reach back and smooth my dress down before sitting down. She taught me how to cross my feet at my ankles and fold my hands in my lap. And how to cross my legs, over my knee. Sometimes I would squish my peanuts doing that and Mom would laugh. She said if I'm ever out with a boy on date to make sure I discreetly adjust myself in my panties before I try to sit like that.

Sarah was assigned by Mom to teach me female bathroom etiquette. She seemed to enjoy this task, teaching me to be like her. She said, "Always leave the seats down in the house and never stand anymore when peeing. Sometimes you have to take your dress or skirt off, but you can usually just gather it around your waist. If you're wearing pantyhose take them down to your thighs along with your panties. If you're wearing stockings take your panties all the way down around your ankles. Since you have that penis, make sure you tuck it down and hold it towards the bottom of the bowl, so you don't splash the rim. In our house we always have feminine wipes on the counters. Wash your penis with the wipes and always wash your hands afterwards."

Sarah started dating a guy from school named Jake. I had met him once and he seemed like a nice enough guy, but I couldn't help but feel a little jealous. I still hoped Sarah and I might get together some day. I even wanted to marry her. But that didn't seem likely, even though she was still my best friend.

On her third date night with Jake, Sarah was getting ready upstairs, and from my basement room, I heard Mom answer the door and invite Jake in. She had only met him briefly once before on their first date. "Hi, Jake. I'm glad you're early. Sarah is still getting ready. Let's go into my office for a little chat."

Mom took him into her office off the kitchen and I heard the door close. I was nosey and listened through the vent in the floorboard.

"So, Jake this is the 3rd time you're going out with Sarah. How are you two doing?"

"Fine, Mrs. Carter. I like your daughter very much."

"And you're what, 23?"

"22."

"And you know Sarah is only 18? Did she tell you she's still a virgin?"

"I guess she mentioned it. Yes."

"And the 3rd date is the magic one, the special one, isn't it? When you boys expect something from the girl?"

"Well, no, I'm not expecting anything."

"Oh, come on, Jake. I expect you to at least be honest with me. I know about boys your age. Raging hormones. What are your plans for tonight?"

"Just dinner and a movie."

"Empty your pockets on my desk. Show me the condoms."

It was quiet for a few seconds but he must have done what Mom said.

"Mrs. Carter, I wasn't planning to use them."

"3? Going for your lucky night?"

"Mrs. Carter, I promise to respect your daughter."

"I'm sure you will, Jake, but I'd like to make sure of that. I want Sarah to remain a virgin. Drop your pants, Jake."

"What???"

"You heard me. Sarah will be at least another 20 minutes. Drop your pants."

Jake must have taken his pants down. There was silence for a few minutes. Then I heard Mom say, "Now your underpants, Jake."

"Please, Mrs. Carter. This isn't necessary. I promise nothing will happen."

"Jake, do you want to go out with my daughter tonight?"

"Yes, Mrs. Carter, but..."

"I don't need excuses, Jake. Your underpants, Jake."

"But..."

"Jake, I said your underpants. Take them down."

Silence again.

"I won't ask you a 3rd time."

There was silence again. He must have pulled his underpants down.

I heard Mom. "An erection. Just as I thought. Take your shirt off!"

"Mrs. Carter! Please! This is humiliating!"

"You will do as I say, or you won't be dating Sarah tonight or any other night! Shirt off, Jake!"

There was silence again. I assume Jake took his shirt off and must have been standing in front of Mom, nearly naked with his pants and underpants down around his ankles. I felt sorry for him, but at the same time it excited me, the way Mom was talking to him. I was getting hard in my panties. And I was curious what his penis looked like. How big he was. I could picture him standing there with his penis sticking out! I wished I was there to see him with Mom.

Then I heard Mom say to him, "Jake, Sarah tells me you're a very nice boy. And Sarah is a very good girl. I'd like it to remain that way. But you won't be dating Sarah like that. Masturbate, Jake!"

"Wait. What? Please Mrs. Carter!"

"You don't have to. You can just get dressed and leave. Or you can simply jack-off, empty your balls and go on a nice date with my virgin daughter."

Jake must have started masturbating in front of Mom. I heard him making those "ugh" sounds.

"Good boy. Keep going, Jake. Here's a wastebasket for you to use." I could hear Mom's heels clicking on the wooden floor pacing around Jake.

He was trying to be quiet, but I heard him say, "Mrs. Carter...I'm going to cum!"

"Go ahead, Jake. It's nothing to be embarrassed about."

There were muffled groans coming from Mom's office.

There was silence again for a few minutes. Then I heard Mom say to him, "Again, Jake."

"What? Mrs. Carter! I can't!"

"Yes, you can. And you will."

Jake must have started again. I heard Mom say, "Good boy." Then I heard smacking sounds. I think Mom was spanking Jake's bare bottom!

Shortly after I heard Sarah knock on Mom's office door. "Mom?"

"We'll be out in a few minutes Honey. I'm just having a little chat with your boyfriend. Go have a seat in the living room."

Jake must have still been masturbating with Mom in the office while Sarah was right outside the door. My penis was stirring and leaking in my panties listening to them.

Jake must have finished while Sarah was right outside the door. Mom's voice lowered and said to him, "Pull up your pants, Jake. Now listen carefully to me. After your dinner I want you to go to the restroom and call me. You'll go in a stall and jack-off. I want you on the phone with me so I can hear when you cum. You'll do the same thing after your movie and have Sarah home by midnight. Do you understand me, Jake?"

"Yes, Ma'am. Mrs. Carter."

"Now, I don't want Sarah to get suspicious tonight and wonder why you didn't try anything, so you can feel her up. Just on the outside of her clothes. Her breasts. Her bra stays on. When you get home, jack-off again before you go to bed. Ring my phone once when you're done and hang up. Are we clear on my instructions?"

"Yes, Mrs. Carter."

"Good. And you don't mention a word of any of this to Sarah."

"Yes, I understand."

"Finally, if there's a 4th date, or any future dates, you will be at least 20 minutes early and we'll have our little office chats. Understood?"

"Yes. Yes, Mrs. Carter."

"Good. Now go have fun!"

Mom and Jake met Sarah in the living room. Mom said to Sarah, "Jake seems like a very nice boy, Sarah. We were just having a nice little chat in my office, weren't we, Jake?"

"Oh, yes, Ma'am!"

I heard them leave together.

I stayed home with Mom when Sarah went out with him. Mom didn't know I heard her in the office with Jake that night. Mom could see I was depressed. She said, "I know you're sad without your best friend here on a Saturday night with you. I told you this would happen when Sarah started dating. Come upstairs to my bedroom. I've been saving something special for you."

I didn't know what Mom meant but I learned by now to never question her or protest anything she ever said to me. I followed her to her bedroom, a place I was rarely ever allowed to be in. Mom went to her closet and brought out a box. There was a label in the corner that said it was from "Sissy's World." Mom put a towel on the bed and told me to take off all my clothes. I decided it best just to do as she says, especially with her hairbrush quite visible on her dresser top. I took off my skirt, top, bra, nylons and my panties and stood naked in front of Mom, erect as I usually am around Mom. Mom smiled pleasantly at me, proud of me for doing as I was told. Mom opened the box and I saw several things in it, but Mom only pulled out one item, a garment I had never seen before. She held it up and said, "This is called a 'onesie,' Tammy." It was sleeveless, pink with baby ducks on it and snaps all down the front. Mom slipped it over my arms and snapped it halfway down. Then she brought out a diaper, placed it on the towel, and told me to lay down on it. Once my bottom was on the diaper Mom brought out a bottle of baby oil and without touching me, squirted the oil onto my penis and peanuts. The cool oil made my legs kick up and Mom held them back down. She swaddled me in the diaper and closed the sides with the Velcro tabs. She pulled the onesie the rest of the way down and there were four snaps that closed over my genitals. Mom patted me on the onesie, over the diaper area.

Mom said to me, "Mommies put their babies in a onesie to comfort them. I know you're sad about Sarah being out with Jake, so Mommy wants to comfort you." With that, Mom went and sat on the back of her bed and braced her back with the pillows. She said, "Come lay across my lap Tammy." I placed my head in Mommy's lap and she cradled me, bringing up the blankets around us. She said, "Mommy is going to have you suckle her," and she began unbuttoning her blouse, then she stopped. "Tammy, I don't want you to mention any of this to Sarah. It will be our little secret, private between you and Mommy. You'll only wear this for me and when I breastfeed you. If I ever find out you told Sarah you'll get my hairbrush. Do you understand me?"

"Yes....yes...Mom."

"Call me Mommy when you're nursing."

"Yes, Mommy."

Mommy's bra opened in the front, and she exposed her breasts to me. She held her nipple towards me and told me, "Open your mouth, Tammy." I took her nipple in my mouth and began to suckle her.

Mom ran her fingers through my hair and spoke quietly and soothingly to me while I nursed from her beautiful tit. "Tammy, I'm doing this for you. To calm you down. It's your quiet time with Mommy. I'm sure you're thinking about Sarah and what she might be doing with Jake. I imagine they are parked somewhere, and Jake is probably feeling Sarah up, maybe even fingering her pussy. She may even have her bra off. She probably has Jake's pants open and is rubbing his penis." I started moaning and squirming, nearly crying.

Mom said, "Shhh, shhh, it's ok. That's how normal couples date, Tammy. I know you feel jealous. You know Sarah isn't allowed to have intercourse, but she will need to keep Jake satisfied. Mommy's tit is here for you to suckle. I gave you the baby oil so it would feel good in your diaper. If you need to ejaculate it's ok, Babygirl. I want you to. Wiggle in your diaper Sweetie."

"UGH!" I squirmed and wiggled, trying to rub my penis against the padding on my diaper. I lifted my hips, trying to get more contact with my diaper.

"That's right, Sweetie. Just wiggle and push. Let it happen. It's ok. Think about your bath time with Sarah. Think about your first time masturbating in front of Sarah and Mommy. It's ok. Suck Mommy's tit and spurt in your diaper, Babygirl."

I wiggled and pushed against the soft, oily padding. After I ejaculated, Mommy held me quietly until I calmed down. I told Mommy I had to pee. "Just do it in your diaper, Tammy. That's what it's for. It's ok. Mommy will hold you while you pee."

"Mommy, please. I don't want to."

"Shh, shh. Hush. Just let it out."

I sucked hard on Mommy's tit, trying to hold back from peeing, but I couldn't, and filled my diaper with my warm piss, mixing with my semen. Mommy knew I was peeing and said, "It's ok, Tammy. Mommy is here for you."

Mommy buttoned up her blouse and took me to take a bath, removed my wet diaper and watched me in the tub. She told me, "Stand up and wash your penis." Mom watched to make sure I washed it thoroughly. She went to her bedroom and brought me a pair of her panties and one of her nightgowns. She said, "Remember Tammy, not a word of any of this to Sarah." I went to my bedroom and waited to hear Sarah come home. It was 11:55 when I heard the door unlock.

The next day I asked Sarah about her date. "I don't think he likes me, Tammy. He barely felt me up in the movie. I tried to take my bra off for him and he wouldn't even let me! And I tried to rub him through his pants, and he didn't even have a boner. He kissed me at the door but said he had to get home to do something. I was frustrated and crying. Mom heard me crying and came in my room. She took off her nightgown and laid down in bed with me and held me."

I couldn't tell Sarah about what I heard in Mom's office. And I couldn't tell her that I thought Mom was being selfish and wanting to keep Sarah for herself. And I couldn't tell her about my night with Mom either. I didn't like keeping secrets. Now I had 3 more.