A Sissy for Sarah

Sarah and I grew up together in the same neighbor as childhood friends. We both led pretty sheltered lives, each with single moms raising us and being home schooled. We didn't get the sex education classes or the gossip behind the school like most kids. We didn't even have cell phones until we turned 18. Our Moms wouldn't allow it. Now we were attending college together at a local college. I was studying Nursing and Sarah was in Business. She was 18 and I was 19. I considered Sarah my best friend, really my only friend. I felt more like her girlfriend. Sarah was developing more friendships in school, but I stayed mostly to myself. She even went on a couple dates with guys she met. She liked the attention she was getting. She never had that before college. She liked flirting with the boys. I never did date anyone. My mom had to move upstate for a new job but Mrs. Carter, Sarah's Mom, said I could live with them while we went to school. She would set up a room for me in her basement. My mom agreed to let me stay with them.

Sarah and I were both short, her about 5'3 and me about 5'5. I always liked her cute face and by now Sarah had developed small breasts, but I think she was still budding. I considered myself average looking. Soft facial features, not much face, leg, or body hair. It was mostly blonde anyway and not very noticeable.

Everything was going fine, and I enjoyed living with them. We shared chores and household duties. In the evenings, Sarah and I would often study together having a few of the same classes. One afternoon, we finished classes and came home early. We went to Sarah's bedroom. We had done it a few times before, but I really wasn't supposed to be alone in her bedroom with her, especially if her Mom wasn't at home. Mrs. Carter came home unexpectedly while I was in Sarah's bedroom. We didn't know she was home when she made 2 quick knocks on Sarah's door and opened it, to tell Sarah she was home. I really wasn't supposed to be alone in her room, let alone the fact that I was wearing one of Sarah's dresses! I was barefoot with a pair of Sarah's panties under my dress. We weren't doing anything. I was sitting on the edge of the bed and Sarah was laying down. She was rubbing her toes on my bare thigh, sort of toying with the hem of my---her dress. We were just talking about school and classes and such. But my face turned beet red from my embarrassment seeing Mrs. Carter walk in on us. She was obviously surprised, more likely shocked, to see me like this, but she was calm and just said, "I want to see you both downstairs in the living room in 10 minutes."

Sarah nervously said to me, "Oh Tommy, this could be bad. I've never told you this, but you know how strict my Mom can be. She uses a hairbrush on my bare bottom sometimes to spank me. I know I'm 18 but she still does it. Tommy, we could get spanked for this! If she asks me any questions, I have to be honest with her. I'm sorry Tommy." Sarah turned her back to me and I got out of Sarah's dress and panties and went downstairs with her to meet her Mom. I was so nervous and upset with myself, feeling ashamed. Mrs. Carter calmly told us to sit down on the couch while she sat across from us in a chair. She had some notes already made up on pad. Mrs. Carter began looking at her notes then talking to us. "First, let me say, I'm not mad or upset with you two. I am disappointed that Tommy was in your room. You know that's not allowed. But I know you're dear friends and sometimes you forget the rules and things happen. What I'm most concerned about and want to know right now Sarah, is why Tommy was wearing one of your dresses. I want Sarah's answers first, please."

Sarah said, "I don't know, Mom. I guess he just wanted to try it on and see. You know, like what it would feel like to wear a dress or something."

"What do you mean you don't know? Did he do this on his own?"

Sarah was cautious, trying to protect me with her answers.

"Kinda. He was looking through my closet. I was on my computer at the time, with my back to him. I didn't really see him. I guess he put it on."

"Has he done this before?"

"I guess, maybe he has...yes."

"You guess? How many times?"

"Maybe 3 or 4 times before."

"Sarah, you would know how many times he's done this."

"Six."

"Six? And you never questioned him about it?"

"I guess I just sorta thought it was cute. You know, that he wanted to try them on."

"Did he ask you if he could try them on?"

"Not exactly, he just sorta did it, like when I went to the bathroom or kitchen or something. I would come back and see him with the dress on."

"Did you ever watch or see him put on the dresses?"

"Mom, yes, ok, I watched him do it, 1 or 2 times."

"Did he take all his clothes off to try on the dress in front of you?"

"No, Mom. Just his shirt and pants. He had his underpants on. I can tell you they were the little boy's kind, little white briefs."

"What does he do after he puts the dress on?"

"Nothing really, Mom. He sits on my bed, and we just talk, kinda like girlfriends, I guess. Like the way you found us."

"Ok. Now, this is important. Does he also wear your panties, Sarah?"

I was getting more nervous and embarrassed. I was afraid what Sarah might say. I know she didn't really want to tell her Mom this stuff.

Sarah told her Mom, "I didn't see him do it, but I think some of my panties have been missing. Maybe they are in the laundry."

"Where were his clothes when he had the dress on?"

"On the floor or sometimes on a chair. But I only saw his pants and shirt in the pile. I guess, maybe I might have seen his underpants there once. Maybe it was twice."

"So, you're saying then you think then he put your panties on too?"

"Yeah, probably, yeah, I mean, I guess he did."

"He never showed you he was wearing your panties?

"No, Mom. Once I think I saw them under his dress when he bent over for something."

"Tommy, since Sarah doesn't seem to know or want to tell me, I'm going to ask you. Do you wear Sarah's panties when you put on her dresses?"

I looked at Sarah. She said, "It's ok, Tommy, tell Mom the truth."

I hung my head in shame. "Yes, Mrs. Carter, I, I, I wear her panties too."

"Tommy, where are Sarah's missing panties?"

"In my room. Under my pillow. I took them from the laundry hamper. I'll put them back. I won't ever do it again."

"Tommy, were you wearing Sarah's panties when I saw you up there today?"

"Yes, I was. I had them on. I'm sorry."

"Sarah, what about your bras, slips and stockings?"

Sarah looked at me again and said, "I'm sorry, Tommy. I have to tell her. I helped him put on a bra once. I think he tried on a long slip, and once, one of my nightgowns. He tried a skirt too. I don't think he knew where to find my pantyhose and stocking drawer and I didn't tell him."

"So, it's been more than 6 times and you were helping him dress."

"I guess so, kinda, yeah."

"I guess your shoes would be too small for him. But mine might fit him."

I thought to myself, "What did she just say??"

"Sarah, besides wearing your dresses, has Tommy ever done anything with you that found odd?"

Sarah turned to me again. "I'm so sorry, Tommy. I have to tell Mom." She turned to her Mom and said, "One time he asked me if he could suck my toes."

"Did you let him? Was he wearing your dress at the time? Tell me what happened."

"Yes, he had one of my dresses on. I let him to do it. At first, I thought he was kidding, but he was serious. He was always looking at my feet when I was barefoot on the bed. I just put my feet out and he laid down at the bottom of the bed near my feet and started kissing them. Then, you know, licking my toes and sucking on them. It tickled at first but then I liked it and just let him do it. Mom, I think he felt embarrassed after he did it. It only happened once but I'm sure he was going to ask me again, if he could get past his embarrassment. Oh, and one time he asked me if he could put my lipstick on. I thought that was odd too."

"Did he put the lipstick on?"

"Yes, Mom, he did. But just for few minutes and he wiped it off. I think he felt ashamed after he did it."

Her Mom still didn't seem mad or upset and spoke calmly to us. "That's interesting, Sarah. Thank you for your honesty. I'm sorry these things may be embarrassing and hard for you to hear, Tommy. I'm sure you thought that what you were doing was private between you and Sarah, but I want to get this all out in the open and I'm glad she's being so open and honest with me. Sarah knows my rules about honesty, or she gets my hairbrush on her bare bottom."

Sarah spouted off, "Mom! Please! Now you're embarrassing me!"

"I'm surprised you never told Tommy you get spanked. You two are so close. I wanted Tommy to know that he's not the only one keeping secrets. Now Sarah, do you think Tommy has been in your room when you're not home?"

"I think so. Sometimes things in my closet and drawers are out of place. Once I found a pair of my panties under my bed and I know I didn't put them there."

Sarah's Mom turned to me. "Tommy, have you ever gone in my room without my permission? Or gone through Sarah's room when she wasn't home? Or done things in the laundry room that you shouldn't?

"Ummm, well, only once in your room, Mrs. Carter. I know that was wrong of me. I'm so sorry. And I've been in Sarah's room too."

"And did you find what you were looking for?"

"I looked through Sarah's closet. At her dresses and skirts. I might have looked in her panty drawer. I'm so sorry."

"And in my room?"

"I just wanted a pair of your panties. I can't explain it. I've gone to the laundry room a few times."

"And what do you do there?"

"Ummm, I'm so sorry, Mrs. Carter....I smell your underwear...your panties...and Sarah's."

"You smell our dirty panties?"

"Yes. I'm so sorry. I know it's wrong."

"What did you do with them besides smell them?"

"Ummmm, after I would smell them, I would take my pants and underpants down and rub them, you know, the panties, on my penis, just a little bit. I didn't want to get caught and I felt guilty about doing it. I put them back in the hamper. I wasn't naked or anything. I just had my pants pulled down for a few seconds."

"How did they feel to you, on your penis?"

"They're not like my underwear. They're much softer, silkier. Some have lace and a frilliness to them. I like the pinks, lavenders and yellows the best. One of Sarah's had little teddy bears on them."

"Was your penis hard when you did this?

I looked won at the floor. "Yes, it was, Mrs. Carter. I really didn't understand it."

"Tommy, did you ever smell your mother's panties at home?"

"Oh, Mrs. Carter, I'm so embarrassed! I did, yes, a few times."

"It's ok, Tommy, we're getting this all out in the open. Sarah and I need to know about this. We're not judging you. Tommy, it's not unusual for a young man to be curious or attracted to a woman's scent---her pheromones. From now on, when you have the urge to smell them, tell me and we will let you do it, but in our presence. I don't want you sneaking around in the hamper and laundry room. Is that understood?"

My face was red, and I had tears in my eyes. I began crying and apologizing. "I'm so sorry Mrs. Carter. I'm so ashamed. It won't happen again. I swear."

"Tommy, I'm not upset with you. Don't cry, Honey. This will all be ok. I just wanted to find out what happened and hear it from Sarah. I know you both haven't had much of a sex education from us Mothers. And you're both pretty naïve about the subject. I'm pretty sure neither of you have had sex and are both still virgins, is that correct?"

Sarah spoke up. "Yes, mom. I don't even have any birth control. Tommy and I have never had sex. We're just friends. I've never had sex with anyone. Tommy has told me he's still a virgin too. He doesn't even know what a condom is for. We were at a drug store once and he asked me what those were behind the counter."

"Ok, I believe you and I hope you both stay that way until you're both married. But I know you're both at a very curious age. Sexually. You both have hormones racing at this age. Let me ask you this, and please be truthful. Have you ever seen each other naked?"

Sarah tried answering for both of us. "Well, sort of, a little, I guess. I mean, I saw him when he tried on the dresses, but just a little, like from behind and the side, not the front. I zipped a dress up for him once. He had the dress halfway up, but was naked underneath, but I only saw him from behind. And a couple times I laid on the bed and took my panties off; Tommy asked me if I would, you know, just so he could look up my skirt a little bit. But I was never naked with him, Mom, honest."

"Honey I'm not mad but tell me, how did Tommy react when you showed him your vagina...your pussy, Sarah?"

"I guess he got kind of excited. He would put his hands in his lap and tell me he thought I looked 'pretty' down there. He said he would like to kiss me there."

"Was he ever wearing a dress when he looked at you down there?"

"Yes. I think always. That's when he would want me to do it. After he would put on a dress, he would ask me to please show him, so, you know, he could just look again."

"Did he ever play with himself when you two did this? Did he masturbate or ejaculate while looking at you? Ejaculate means spewing or spurting. Some call it cumming but I don't like that word for boys. Did Tommy ever spurt?"

"I don't think so, Mom, but I can't be sure. Sometimes he had his hand under the dress while he looked at me. He might have been touching his panties."

"Were there any stains on any of your dresses or panties after he wore them?"

"Maybe just a few little spots around the area that his penis may have been touching it."

"How did it make you feel when he was looking at you? Did you feel a wetness in your vagina...your pussy, Sarah?"

"Yes, I would get excited when he said he wanted to see it. And the look in his eyes when I would take my panties off excited me. It made me wet."

"Did he ever touch your pussy, Sarah?"

"Oh, no. He never did that!"

"What about you? Do you touch yourself?"

"Sometimes---in the shower."

"Sarah, have you ever seen a naked man's hard cock in person?"

"Just a glimpse, a little bit of Tommy's, once or twice, but like I said, not from the front."

"Tommy never tried to show you his penis the way you showed him your pussy?"

"No, Mom. He's kinda shy about stuff like that. He just likes putting on my dress and looking at my pussy."

"Was he looking at your pussy when I caught you two in the room?"

"Just before you came in, he asked me if I would take off my panties. You came in before I took them off."

"Do you think Tommy wanted to touch himself while he looked at you like that?"

"I don't know Mom. Like I said, I never saw him do that and he never said he wanted to do that. I asked him once why he liked wearing my dress and looking at my pussy. He said he'd never seen a girl's pussy before and liked looking at mine. He said the dress felt good. That's all we've ever done, Mom. He puts on my dress; I take off my panties and spread my legs a little bit so he can look at my pussy."

"How about touching a man's penis? Have you done that?"

"Just once on a date, but more on the outside, through his pants."

"Tommy, what about you? Have you ever seen a man's hard penis in person?"

"Ummm, I've seen pictures in a magazine once. I was at a bookstore and got curious. There were two men naked together.

"How do you feel when you saw that, Tommy?"

"I'm not sure, Mrs. Carter."

"Did you feel excited? Did it give you an erection?"

"Ummm, yeah, I guess it did. I felt a stirring in my pants, like a tingly feeling. A drop leaked out in my underpants."

"So, you like looking at cocks, hard penises? Have you ever had the urge to kiss a man's penis or put your mouth on a man's penis?"

"I guess I'd be lying if I said no."

"It's ok to admit this to me, Tommy."

"Sarah, any desires to be with a woman?"

"No, Mom. I mean I never really thought about it. I mean I like when you still snuggle and cuddle with me and helping me with my personal hygiene."

"Have you two ever laid down in bed together?"

"No, Mom," Sarah answered. "I mean, I guess we both laid down on the bed when he was sucking my toes, but at opposite ends. Never face to face."

"Have you two ever kissed?

Sarah said, "No, Mom. He has never tried to kiss me. I've only ever kissed two boys on two dates."

Mrs. Carter asked me, "What about you, Tommy? Ever kissed a girl? Or a boy?"

"No, Ma'am. No one."

"One more thing. Have either of you ever watched any pornography?"

Sarah and I looked at each other and shook our heads "no."

Mrs. Carter spoke up, "Ok. What you've both been doing is natural curiosity. But Tommy's behavior is a little more than that. It's called Sissy behavior or effeminate behavior. It's nothing to be ashamed of. You seem to like both male and female sex organs, Tommy. You could be bisexual, but the smelling, toe sucking, dresses and panties tell me a different story. You're a Sissy, Tommy. That term can be a little shocking to some boys. Are you ok being called a Sissy, Tommy? If Sarah and I called you a Sissy?"

I looked down at the floor. "Does Sarah think I'm a Sissy?"

Sarah replied, "I'm sorry, Tommy, but yes, I do. After what Mom said, and the questions, I have to agree with my Mom."

Mrs. Carter told me, "Don't be sad, Tommy. It's not a bad thing. You're just a more delicate and sensitive boy, more feminine and girly than manly. Tell me, how do you feel when you're wearing Sarah's clothes?"

"I don't know exactly. Just sort of excited, I guess. Like tingly, all over my body."

"And do you get an erection, a hard penis, when you put her clothes on? Her dresses and her panties? Her bra? In other words, is your penis hard when you do this?"

"Yes, I suppose it is. It gets hard."

"And what do you do about that?"

"What do you mean?"

"I mean, your erection causes you to have stronger sexual feelings. You like to wear women's clothes. You haven't had sex with Sarah or even touched her. You'd like to suck a man's cock, yet you haven't. You've never seen a naked man or a woman, yet your mind fantasizes about both. I'm asking, do you relieve yourself? Do you masturbate? Did you make stains on Sarah's panties and dresses?"

"Omg, Mrs. Carter, maybe a little leaked out. I'm sorry. To be honest, I don't really know what to do when I feel that way. You know my mother was very strict and taught me never to play with myself. There were parental controls on my computer and TV growing up, so I never saw much of anything. I didn't have video games. I wasn't even allowed to get a cell phone until I turned 18 last year. I've never even seen an R rated movie."

"Well, without relief, Tommy, you build up semen in your testicles...your balls, Tommy, and they begin to hurt and ache. Has that ever happened to you?"

"Yes. One time it was bothering me so much that I got this urge to lay down on a pillow and it felt like I was going to pee, but white cream came out instead. I felt embarrassed. And sometimes when I'm sleeping stuff comes out."

"Those are wet dreams, Tommy. It's an erotic dream that causes involuntary ejaculation of your semen. It means you didn't mean to do it but were dreaming about something sexual and you ejaculated.

Your humping the pillow is a way a lot of boys, and girls masturbate. It's nothing to feel embarrassed about. That was an orgasm Tommy, not pee. You're going to have to learn to masturbate, Tommy, to relieve yourself. If you're going to be living here, you can't be sneaking around wearing Sarah's clothes and then getting excited with no relief. If looking at Sarah's pussy helps you, I don't mind if she shows it to you. I just don't want you two having sexual intercourse. Masturbating will stop you from pursuing that. And the same goes for Sarah. Girls have urges too. But what I'm suggesting stays here, private, between the 3 of us. Some parents would frown on this, but I think it's better to get an education from me then from porn on the Internet or on the school campus. Are you both agreeable so far?"