Mrs. Watson and Me
By Alice64.
One day, she saw me outside and asked me to do some chores for her. I assumed she was asking me to do some chores for her. When I got inside her house, she said, “This isn’t about chores today, Jamie. Your mother asked if I might speak with you. Please sit down.”
I took a seat at her kitchen table.
“Jamie, this may be hard to hear and embarrassing to discuss. But rest assured, I’m not here to embarrass or judge you in any way.”
“Ok. What is it, Mrs. Watson?”
“Your mom says she knows you’ve been trying on her clothes, specifically undergarments, and she doesn’t know how to talk to you about it, so she asked me if I would.”
“Oh, Mrs. Watson, I’m sorry. I didn’t know she knew! And now she told you?”
“Yes, honey, she told me everything. Honestly, it’s nothing for you to feel ashamed about, but talking to your mother about it may be hard. Many young boys like yourself are still experimenting sexually and can be excited by female clothing.”
Mrs. Watson reached out and held my hand from across the table.
“Jamie, your mother came to me about this because she knew something about me that no one else knew. My late husband, Earl, was a crossdresser. We had a very happy, wonderful life together privately at home. You know he passed away last year. Your dear mother, Mary, and I became very close, and I had told her about Earl. She’s concerned about you and wanted to see if I could help. Are you okay with talking to me about this?”
“Umm…yes, I guess so, but can you tell me how she found out about me?”
“Jamie, things were misplaced, missing from the hamper and laundry, missing from her panty drawer, stains left on her garments. She never actually saw you, if that’s what you mean.”
I hung my head, and Mrs. Watson squeezed my hand.
“Jamie, I know this is a difficult conversation for you, but I understand. It was hard for Earl to be open with me at first. I’m not saying you’re a crossdresser at this point, but if you’d like to explore that, I want to be here for you. And that’s what your mom wants, too. So, can I ask you some questions?”
“Ok. I guess so.”
“Good. This is going to get very personal. Your mom says you’ve tried to peek in on her when she’s showering and getting dressed. Is that true?”
“It was just accidental, Mrs. Watson.”
“I don’t think it was, Jamie. She says you’ve done it more than once, and she’s seen you outside her bedroom door when she’s getting dressed or ready for bed. And you deliberately opened the bathroom door while she was bathing. She said you stare at her feet. Does it excite you to peep at your mom?”
“Mrs. Watson, it’s just me and my mom at home. I haven’t had much experience with girls or dating. I guess I was just kinda curious.”
“Have you ever seen a naked woman in person?”
“No, not really, just my mom.”
“What about a man?”
“Umm, well, you know, at the gym or something. The locker rooms. Showers.”
“And do the naked men excite you?”
“I don’t know. Maybe. I guess so.”
“It’s ok, Jamie. We’re just talking, ok? We’re private here, Jamie. You can tell me anything.”
“Yes. Ok.”
“Have you ever had sex with a man or a woman?”
“Not really. I dated a girl a few times. Ok, maybe only actually once.”
“Did anything happen?”
“We parked. I felt her up a little. I unbuttoned her top and saw her bra. She told me to open my pants and unzip them. She saw my size outlined in my underpants and laughed. She told me to put my hand in my underpants and, you know… jack off while I looked at her tits in her bra. I was hard, and I came as soon as I started touching myself. I felt humiliated. She laughed at me.”
“I’m sorry that happened to you, Jamie. She made you feel ashamed. I’m not here to shame you, Jamie.” Mrs. Watson began unbuttoning her blouse. “But tell me how you feel when you see me in my bra. Does it remind you of her? Or when you see your mom in her bra?” She opened her top and stood in front of me in her bra.
“Oh, my, yes, mmmm…Mrs. Watson, so nice!”
“Does it make you want to touch yourself, seeing me like this? Or when you think about your mom in her bra looking like this?”
“Oh, Mrs. Watson! I’m ashamed to say it, but yes!”
“That’s ok, Jamie. Lots of boys have fantasies about their mothers.”
She buttoned back up, sat at the table, and continued questioning.
“What about men? Have you ever had sex with a man? Touched his cock? Looked at naked pictures of men?”
“No, Ma’am, not really.”
“What does that mean? Tell me, do you look at porn online?”
“Sometimes.”
“Just sometimes?”
“I guess I do it a lot.”
“What do you look at?”
“I look at girls.”
“Just girls?”
“Well, this is embarrassing for me to admit, but sometimes I look at men, like wearing panties and lingerie and stuff.”
“Don’t be embarrassed. That’s what your mother thought you were doing. She found some of your history and searches on your home computer.”
“Oh. I guess I need to be more careful.”
“Not with me. Next time you’re here, you will show me some websites you visit. You don’t have to feel ashamed to show me. Remember, my Earl was a crossdresser.”
I hung my head, unsure how I felt about showing her that stuff about me. She saw I was uncomfortable and changed the subject back to my mom.
“Tell me, Jamie, what items have you taken from your mom.”
“Umm, you know, like panties, slips, nylons…”
“Would you be able to take those items from the hamper? Soiled panties?”
“Usually, yes. But sometimes clean ones, from her panty drawer.”
“Her bras, too?”
“Yes, but it was rather big on me. Mom has some pretty big tits, if that’s ok for me to say.”
“It’s fine, Jamie. Tits is fine to say with me. You can say anything to me. And you like seeing your mom’s big tits in just her bra and panties?”
“Oh, Mrs. Watson, is it bad if I say I do?”
“No, Jamie. Remember, I just want you to be honest with me. Your mom knows you’ve been looking at her. She paused and asked, “Do you try her things on?”
“Well…yes.”
“How does it make you feel when you try on your mom’s panties and nylons?”
I had tears in my eyes. “I’m sorry. I like it. It feels good. Please don’t tell my mom.”
“That’s ok, Jamie. If it didn’t feel good, you wouldn’t be doing it. And I think your mom knows that about you, too. I just need you to be honest with me. I just wanted to let you know I’m not here to chastise you. I’m just here to help you.”
She continued, “Now, let’s get more serious. Tell me, do you smell her panties?”
“OHHHHH—I’m sorry…yes, I do.”
“Jamie, that’s quite normal.”
Then she asked me, “How about a dress or skirt? Have you ever tried them on?”
“Oh, Mrs. Watson, yes, I did that too!”
“And have you tried to wear your mom’s shoes? Her high heels?”
“Yes, but they’re too small for me.”
“What about a garter belt? Would you happen to know what that is? They hold up your stockings. Does your mom have one of those?”
“I think I saw one. I wasn’t sure how to use it.”
“But you’ve seen your mom put on stockings?”
“Umm…yes…the stay up kind. And her pantyhose.”
“And that excited you?”
“Umm…yes, I guess it did.”
“Did it make you hard—your penis— when you watched her doing that? Putting on her stockings?”
“I guess so.”
“You ‘guess so,’ or do you get an erection when you’re watching her?”
“I get hard.”
“Do you play with yourself after watching her?”
“Maybe just rub myself a little.”
“A little?”
“Ok. Sometimes, I, I, masturbate.”
“What about when you wear your mom’s clothes? Touch yourself, then? Play with your penis?”
“Umm, well, yes.”
“You masturbate to completion? You ejaculate?”
“Sometimes…well, usually. Almost always. If I’m sure, I won’t get caught. Yes.”
“That’s a good indication that you want to be a sissy.”
I thought to myself, ‘sissy?’ Where did that come from? What did she mean?
“It’s nothing to feel ashamed about, Jamie. Earl used to love to masturbate wearing his panties.”
“Ok, Jamie, as I see it, you have several choices here. 1. You can just stop completely. We know that won’t happen. 2. You can learn to hide it better from your mom. That’s not likely. 3. You can tell your mom and risk how she might react or allow me to help you.”
“How would you help me?”
“Well, I would tell your mom for you to save you that embarrassment. And then we’d just take things slow. We’re close to the same size. I’m sure I have some things here you could try on and wear. When you’re ready, we could shop for some things.”
“Wait. What? You want me to wear your clothes?”
“Yes, Jamie. You can’t sneak around at home trying on your mom’s clothes. You’re embarrassed to admit it now, but you want this, Jamie. I have closets and drawers full of frilly, sexy, feminine clothes you can wear. You can be the sissy you want to be.”
“Oh, my!”
“Of course, I’ll have to talk to your mom.”
“You’d tell my mom?”
“Yes. She asked me to help you. I’ll have to tell her the truth. That you’ve admitted to wearing her clothes and masturbating. And that I’m having you dress here with me. Hopefully, that will ease the tension at home. I’m going to suggest to her that she allow you to wear panties at home.”
“Oh my! Really? Do you think she would allow me to do that?”
“Jamie, behind her back, she already knows you’ve been doing it secretly. Let’s get that part out in the open with her.”
“Ok. I hope she’ll be ok with it.”
“I’m pretty sure she will agree.”
“Oh my!”
“Then we can start here. Once your mom knows, you can come over after your classes during the week and spend the weekends at my home.”
“Jamie, if you want to smell my panties, you won’t have to hide it. You’ll be able just to ask me for my panties. We will explore different styles of clothes, hosiery, shoes, make-up and more. I still have some of Earl’s things we could start with. I would need to become very familiar and intimate with your body.”
“What does that mean?”
“It means you will be dressing and undressing in front of me. You’ll often need to be naked. Can you handle that?”
“I’m not sure. I’ve never been naked in front of a girl…or a woman before. But I think maybe I can, Mrs. Watson.”
“How would you feel about being naked or just wearing panties in front of your mom?”
“If she’d be ok with that, I think I would like it.”
“Well, it will be like that except with me. What about wearing a bra and stockings in front of your mom?”
“Omg, honestly, if she would allow that…wow.”
“Good. Why don’t we start now? I’d like to try something with you.”
“What do you mean, Mrs. Watson?”
“Jamie, take off your clothes for me.”
“What? Now? Here in the kitchen?”
Mrs. Watson waited. She lightly tapped her fingers on the table, looked at me, and said, “Yes.”
I wanted Mrs. Watson to help me with my thoughts, desires, and urges. However, I was hesitant and embarrassed to undress in front of this older woman. Finally, I took off my T-shirt and lowered my pants.
She said, “Take them off. And your shoes and socks.”
I stood in front of her.
“Take your underpants off.”
“Mrs. Watson…”
“You’ll have to learn to trust me, Jamie.”
“But my penis is hard!”
“I fully expect it to be when you’re with me. It’s a natural reaction. Take your underwear off, Jamie.”
I was nervous, but I slowly managed to get my tightie whities over my boner and lowered them to the floor. I tried to cover myself.
“Jamie, put your hands down. Stand up straight, legs together. Oh, Honey, you are very small. I don’t mean to hurt your feelings, but I understand why your little girlfriend was disappointed.”
I hung my head in shame.
“Aww, don’t look so sad, Honey. It’s going to be alright.”
Mrs. Watson had a firm, commanding voice, yet she seemed sympathetic and understanding. She went to her kitchen drawer pulled out a pair of blue nurse’s surgical gloves, and pulled them on her hands. She brought out a tape measure. “3 7/8. You’ll look a little bigger once I get you shaved.” She came over in front of me and said, “Raise your arms.”
As I did, she told me, “Sissies are hairless. We’ll shave your armpits. You don’t have much hair on your chest or legs so we can use a depilatory on those areas.”
There was that ‘sissy’ word again! But it made my penis twitch when she said it. I had so many questions running through my mind. Shaving? What was she talking about? Why did I take my clothes off in front of her and subject myself to this?
She moved my penis side to side with her finger and then examined my balls. She said, “We’ll shave this area but leave a little patch of hair above your penis. That always looks cute for sissies.”
I was blushing and not sure how to react. She pulled off her gloves and threw them in the garbage.
She said, “Follow me upstairs.” Walking naked behind her, I was still hard; she took me by the hand and led the way to her bedroom.
“Open my top drawer, Jamie.”
Her top drawer was filled with panties, bras, and nylons.
“Jamie, I understand you’re feeling nervous and ashamed right now. It’s ok. I want you to pick out one of my panties you’d like to try on.”
“Mrs. Watson, I…”
“It’s ok, Jamie. It’s why I brought you up here to my bedroom. Imagine this is your mother’s panty drawer. Only these are mine. I’ve worn all of them. You’re going to show me what you like to do with your mother’s panties.”
There were so many—different kinds, a few unusual ones. I passed over those. I ran my hands over them, feeling the soft textures—nylons, silks, lace. I picked a white see-through nylon panty with black lace around the waist and leg openings. I held them up and asked her, “Are these okay?”
“Those are quite lovely, aren’t they, Jamie? Yes, they will be fine. Go ahead and put them on.”
I pulled them up my legs and over my ass. They fit me perfectly.
“Look in the mirror, Jamie. Get used to the way they look and feel on you.”
I stood in front of her dresser mirror. I couldn’t help but admire the way my little hard cock looked in her panties.
“Run your hand over the panties. How do they feel?”
“Oh, Mrs. Watson, I’m ashamed to say how good they feel.”
“That’s perfectly fine, Jamie.”
Mrs. Watson said, “Now I want you to lay down on my bed and play with yourself in my panties. Show me what you did with your mother’s panties.”
I felt embarrassed and ashamed.
“Jamie, don’t feel bad. You did this alone at home, in secret. You won’t have to hide when you masturbate here. You’ll do it in front of me. It’s a very natural act. I’m here to help you. And I won’t laugh at you the way that girl did.”
I started rubbing myself on the outside of Mrs. Watson’s soft panty. I was getting hot and started to leak.
“That’s right, Jamie. It feels good, doesn’t it? There’s nothing to feel ashamed about. You’re private here with me.”
I was panting and unable to answer her other than groaning.
“Put your hand in my pretty panties. Imagine me wearing them. Imagine how those would look on your mother. Masturbate in my panties.”
I put my hand inside the panties and began stroking myself while Mrs. Watson watched me.
“My panties feel good on your little penis and balls, don’t they, Jamie?”
I started panting. “Yes…oh my…yes!”
“Do you want to cum in my panties, Jamie? Like you do with your mom’s?”
“Ugh!” I filled Mrs. Watson’s panties with my sperm as it spilled through the material, out the sides, and down my legs.
Mrs. Watson worked the wet panties down my legs and off. She brought a warm washcloth over, put on another pair of rubber gloves (it appeared that she had boxes of these stored all over her house) wiped me up, lifting my penis with just her index finger and thumb.
“Jamie, that was a very good start for today. This weekend, we’ll do your shaving and personal grooming of your genitals. You can try on more panties, and I’ll show you how to put on your stockings with a garter belt. I want to get you measured for your bras, too.”
My head was spinning. What just happened? What was she talking about with all this? I took my clothes off and jacked off in front of a neighbor lady, 30 years older than me, whom I barely knew, in her panties! And she’s talking to me about feminine things and sissies and staying with her on weekends! What did my mom tell her about me?
Mrs. Watson told me, “You can go to the kitchen and get dressed now.”
As I was getting dressed, Mrs. Watson was coming into the kitchen, and I could hear her talking on the phone and knew it was my mom. I heard her telling her, “Yes, Mary. No, no, everything went just fine. Jamie is very polite and respectful. I’m sure you’ll be pleased with some of the decisions he’s making regarding his life and future. Don’t press him about it at this point, but suffice it to say we had a wonderful conversation today. Yes…I’m sending him home for dinner now. Yes. This weekend. Right. Ok, goodbye, Mary.”
“Jamie, we must have you ‘come out’ to your mother.”
I still didn’t understand what she meant, but we exchanged phone numbers before I left.
The following night, I got a text from Mrs. Watson. It read: “I spoke to your mother, and she’s fine with this, but you must ask her. ‘Mom, may I please pick out a pair of your panties to take with me to Mrs. Watson’s this weekend?’ Don’t worry. She will say ‘yes.’ I promise.”
The weekend came around, and I nervously headed next door to Mrs. Watson’s.
“Mrs. Watson, I’m still unsure what this is all about.”
“You live at home with your mom. You’re sneaking around peeking at your mom while she’s naked and stealing her panties and nylons. Smelling them and masturbating. You have a small penis, and you’re looking at gay porn and men dressed in lingerie. You’ve only dated one girl, and that ended badly. Your mom suspects you’re a sissy, just like Earl was. Need I say more…Sissy?”
I hung my head. “I guess not.”
“Did you bring your mom’s panties?”
“Yes. I was embarrassed asking her for them.”
“But she didn’t object, did she?”
“No. We went right upstairs to her panty drawer. She helped me pick them out.”
“Show them to me.”
I showed Mrs. Watson the silky pink panties I brought from my mom.
“Oh, you like pink. Very sissy color. Perfect! Upstairs now. In my bedroom, I put towels on the bed. Take your clothes off and lay down face up on the bed.”
“Please, Mrs. Watson, we don’t have to do this.”
“Your mother giving you her panties disagrees, and so do I.”
I sheepishly took off my clothes. I was immediately hard again, like last time. Mrs. Watson ignored it and said, “Knees up, bent, feet flat on the bed.”
With her rubber gloves on, she began rubbing a cream all over my legs and chest. She pulled my butt cheeks apart and dabbed the cream around my hole. She said, “This light hair will be gone after you shower. And we can shave your armpits in the shower. I’m going to shave your genitals now while the cream works. Just relax.”
She had a pan of warm water and her razor ready. She began by pulling up my ball sack and started shaving underneath and all around my balls, then moved on to the few hairs around the base of my penis. She used her scissors to first trim the long hairs around my crotch and above my penis and then shaved me smooth, leaving just a tiny patch of hair above my penis. Then she told me to shower, and I watched the hair on my legs and chest disappear. I felt like a little boy or maybe a sissy? She had me lift my arms, and she shaved my armpits smoothly. After drying me off, she rubbed lotion on my legs, crotch, arms, and chest. Then she said, “You can put on your mother’s panties now, and then we’ll get you into your nylons.”
I still had a raging hard-on when Mrs. Watson handed me my mother’s pink panties. I knew they would feel nice against my smooth, freshly shaved penis and balls, so I didn’t resist. I slipped on my mom’s panties and sat down on the bed.
Mrs. Watson brought out a pair of nylon stockings from her drawer. “These are called ‘thigh highs.’ They stay up around your thighs with the elastic in the stocking tops. Point and curl your toes up tight.”
She showed me how to roll the stocking down, slide it up my leg, and smooth it. “Be sure you go slow so you don’t snag your stockings. Runs in your hose are very unattractive and costly when you have to replace them.”
When I had them on both legs, she asked me, “So, how do you like them? How do they feel?”
“Umm, well, they feel nice on my legs.”
“Of course they do! Sissies love wearing nylons! Take a look in the mirror.”
I stood up and walked over to Mrs. Watson’s full-length mirror. I couldn’t help but feel excited by the look and feel of wearing panties and nylons. Several drops of my pre-cum leaked into my panties.
Mrs. Watson said, “Watch yourself in the mirror and jack off. Pull your panties down a little.”
I was excited. I’d been hard since I arrived at Mrs. Watson’s this morning. The nylons looked and felt so good on my shaved legs. I wanted to see how my penis and balls looked with no hair around them. Mrs. Watson watched as I lowered my panties to my thighs. There was something “cute” about this new look and that little patch of hair she left above my penis. Mrs. Watson laid a towel on the floor before me and sat on the bed to watch.
“You’re becoming such a cute little sissy, Jamie. Jack-off. I want to get you measured for your bras.”
I wrapped my hand around my penis and started stroking myself, and it didn’t take long until I shot my load on the towel.
Mrs. Watson handed me some tissues and said, “Wipe yourself. Take off those panties. They need to be washed. You can pick out one of mine now for the rest of the day.”
I was naked except for the stockings, and my penis had finally gone limp while Mrs. Watson brought out a tape measure. She measured my chest. “We’ll get you 34A bras to start. There are ways to increase your bust size, primarily with hormones and estrogen creams, and that help to give you smaller erections, too. Earl used them and grew a cup size.”
She led me to her panty drawer again. She laughed and said, “I have pink ones, too, if you want to wear your favorite color again.” I noticed one of her bras with the tag showing…36C. I would go home and check out my mom’s bras to see how her size compared.
I blushed, hurriedly grabbed the silky pink ones, and sat on the bed to put them on. I must admit they did feel nice over my shaved penis and balls. After I had them on, I started to remove the stockings.
Mrs. Watson stopped me. “Leave your stockings on. You won’t have heels or a bra today, but I’ll find you a dress to wear, and we’ll start on some housework.”
Mrs. Watson zipped me into a light blue dress that reached just about mid-thigh. I feared telling Mrs. Watson, but I found the day more stimulating and exciting, being dressed this way with her. We went to the kitchen, and my feet felt great in nylons sliding across her tile floor. She had me clear her kitchen table and did the dishes while she sipped coffee, read the paper, and supervised me. I made us sandwiches for lunch.
That afternoon, Mrs. Watson taught me how to paint her bright red toenails while watching TV. My hands were shaky, and getting her toes right took me a while. I had to wipe the polish off several times on her toes until I got it the way she wanted and approved it. I tried to peek up her skirt but couldn’t get a clear view. She said, “Next time you’re home, offer to paint your mom’s toenails.”
She taught me how to make a meatloaf for dinner. That night, I slept in her guest room in a teddy and panties she picked out for me. I had an erection most of the night. I fell asleep with my hand in my panties, holding my erection.
The next day, we went shopping at a high-end department store. Mrs. Watson had me wear my mother’s panties again after I hand-washed them in the sink last night. She picked out a pair of black, sheer thigh-highs to wear under my pants. The sexy undergarments with my smooth skin made me feel so good yesterday that I didn’t resist wearing them.
In the ladies’ Intimates Department, salesladies watched us as Mrs. Watson held up several bras to my chest in A cup size that she said I would need. I felt embarrassed but excited in a strange way. Next, we visited the hosiery aisle. Mrs. Watson pointed out different styles and then said, “Look. These are vintage-style stockings. See how these have the nice back seams? They have no elasticity. You must wear them with a garter belt or panty girdle with garter straps. We’ll get you some of these stockings today, nude and suntan and a garter belt.”
She asked a saleslady, “Where are your garter belts?”
The clerk directed us to a rack of garter belts, and Mrs. Watson held them up to my waist. I was shocked and it appeared the saleswoman was too. Mrs. Watson asked the woman, “What do you think? Does he need a small or medium?” She draped both sizes back and forth over my waist. The woman didn’t answer. She just kind of stood there and didn’t know what to say. Mrs. Watson told her, “I’ll just have him try these on,” and she grabbed both sizes in both pink and white and carried them with her.
Then we walked over to the panty section, and she had me pick out four new pairs. My penis was hard as we shopped together, and the small bulge in my pants was visible. She picked out two dresses for me. It was easy to find dresses that fit my small, 5’6 frame and slender body. She told me to try them on in the ladies’ dressing room. “Show me when you’re dressed. And try on a garter belt under your dress. The medium should work. I can always adjust it if you need it smaller. I’ll watch by the doors here if anyone comes.”
Naturally, I felt embarrassed doing this, but I entered the dressing room with the two dresses and the garter belt.
The first dress was “flouncy.” It was a light blue floral print with a flared skirt that swished around my waist, and it felt good over my nylons. I pulled it on over my head. I looked at myself in the mirror and felt “pretty.” I knocked on the door to tell Mrs. Watson I was ready to let her see me. She opened the door and said, “Very nice, Jamie! Do you like it?”
It was hard to admit the truth to her, so I said, “I think so, yes.”
“Ok, try the red one.”
The red one was much more flattering to my slender figure. It fits tight, and the hem ended about 5″ above my knee. Almost a “mini-dress.” I did think it made my legs in nylons look sexy. I got an erection when I put it on, and it forced my dress to show my little bulge poking out in front. I needed help with the zipper, so I knocked and asked Mrs. Watson for help.
Just as she opened the door, a lady wanting to use my room walked by and peeked in at me. I felt embarrassed, but Mrs. Watson said, “Don’t worry. It’s fine. How do you like this one?”
“I guess it’s ok too.”
“It looks like you like it! A lot! That’s very sexy on you! Your panties are pushing out the dress. Lift your dress and show me the garter belt.”
I pulled my dress up. I didn’t have it attached to the stockings, but it felt wonderfully erotic to be wearing it.
“Jamie, that looks just darling on you. Wait till you have your new stockings attached! We’ll take both dresses.”
I was going to get changed and asked her to unzip me and please close the door. Mrs. Watson kept holding the door open while she unzipped me, and I took the dress off. The woman came by again and saw me in my nylons, panties, and the new garter belt. I felt so embarrassed, but Mrs. Watson smiled at her and said, “‘She’ll’ be done in a minute.” I turned my back and dressed quickly while Mrs. Watson opened the door so everyone could peer in!
In the shoe section, she asked a salesman to bring us a pair of black 3″ heels she found in size 10, a size she presumed I could wear. He brought them out and handed her the box, thinking they were for her. She handed me the box, with the salesman watching and said, “Here. Try these on.”
The salesman said, “Oh, I’m sorry, no one can try on shoes without a footie or nylons. Would you like a footie…er…sir?”
Mrs. Watson told the clerk, “He doesn’t need one. Take off your shoes, Jamie.”
I was embarrassed but thought it best not to make a scene to attract more attention in the store, so I sat down, took off my shoes, and exposed my nylon-covered feet in front of the salesman. I slipped the heels on quickly, said, “They fit,” and quickly took them off.
Mrs. Watson said, “No, no. Let me see them. Stand up and try to walk.”
I felt humiliated but gave my best effort and took a few steps before Mrs. Watson and the salesman. She said, “Lift your pants so I can see them.”
I looked around at the other customers in the store feeling ashamed and nervous, but I lifted my pants to show the shoes and my nylons. She seemed satisfied and asked the man, “Do you have them in red also?”
He said, “I think so,” and went to the stockroom to check.
I tried taking the heels off, and she stopped me. “Leave them on until he gets back. Get used to how they feel on your feet.” Mrs. Watson was wearing a similar pair on her feet. Several women around us were shopping and couldn’t help but notice that I was wearing heels. I heard one of them say to her friend, “Such a sissy!”
The man brought a red pair, and she responded, “Thank you. We’ll take both. He’ll wear these out.” The other women who were still shopping gave me a few strange looks.
Mrs. Watson had me wear the black heels out to her car. I didn’t want to stumble to attract unwanted attention, so I walked upright and tried not to look down at my feet. Luckily, the car was parked nearby. When we got in the car, Mrs. Watson told me, “Take your pants off and put your new heels back on.”
I did what she told me and sat in my mom’s panties, stockings, and new high heels as she started on our drive home. My penis was hard in my panties.
Mrs. Watson asked me, “How are you feeling? Are you excited about trying on all your new clothes?”
“I’m so nervous right now, in the car like this with you.”
“Don’t be nervous. No one can see you except me. Take a picture of your legs and shoes, then send it to your mom.”
“Oh, I couldn’t!”
“Sweetie, she’s been suspecting you anyway. You brought her panties over. I told her we were going shopping today. Could you take the picture and tell her you’re wearing her panties, too? You’ll feel better once she knows and not have to keep secrets from her.”
I took out my phone and snapped the picture.
“Send it, and I’ll tell you what to text her.”
I couldn’t believe it, but I sent my mom the picture of my nylon-covered legs and black heels!
“Ok, now text her: ‘Yes, mom, that’s me. I’m wearing your panties and these stockings and heels that Mrs. Watson bought me while driving us back home. I hope you understand.'”
I sent it, and Mom texted me back. “I do understand, Honey. I knew you’d been taking my things. I’ve seen you trying to watch me and the gay sissy porn on your computer. I hoped Mrs. Watson could help you since I knew about her husband, Earl. I see she’s helping you, Sweetie. Your legs look lovely in those stockings and those shoes are so pretty! I just want you to be happy, Honey.”
I read the text to Mrs. Watson. She said, “See? I told you to trust me! Now put your hand in your panties, Sweetie.”
Reading Mom’s text gave me a sense of relief. My penis was hard and throbbing in my panties. I put my hand inside and sighed.
“Go ahead and jack off in your mommy’s panties, Jamie.”
“In the car? Now?”
“Yes, Baby. You’re hot and excited. No one can see you except me. Go ahead.”
I was soooo hot, I had to do it! I came quickly, just as we pulled into the driveway, covering the front of my panty with my semen. Mrs. Watson grabbed her phone and quickly took a picture of me in my mom’s panty soaked with my cum…and sent it to my mom!
I was shocked when she sent back a smiley face emoji!
I spent the next two weeks as often as possible with Mrs. Watson, after school, after work, and on weekends. I tried on all the new clothes Mrs. Watson bought me, and she started having me wear make-up at home. She would do my face and put my long hair in pigtails with ribbons. She had me pierced my ears so I could wear dangling earrings and hoops. I felt sexy around Mrs. Watson and always felt hard in the panties she made me wear with her. She had set up space for me to hang my dresses and skirts in her closet and gave me my panty drawer. It became routine for me when I got to her house to immediately go upstairs and begin changing. This particular day, I was about to get dressed when Mrs. Watson said, “Jamie, I want you to try something new today.” She brought out a thong panty!
“Oh, Mrs. Watson, that’s so small!”
“Jamie, you’re small enough to wear these, even if you’re hard. And it will look just darling over your tiny penis, Sweetie! Put it on, Jamie.”
It was a tiny triangle with those little strings that go around your legs and a string that goes up the crack of your ass. I got undressed in front of Mrs. Watson, already sporting my erection in full view. She handed me the pink thong, and I worked my legs into the strings and covered my little package with the tiny triangle of material.
“Oh, Jamie, those are sooo cute on you! You can go on dates with a thong, and your man won’t even know you have a little penis under your dress!”
I didn’t think she was being serious, but it did cause me to leak a few drops in my thong. She told me to wear it the rest of the day.
My mom was happy I wasn’t out drinking or hanging with the wrong crowd and was safe next door with Mrs. Watson. I didn’t know if she knew exactly what I was doing with Mrs. Watson, but I suspected she had a pretty good idea by now. She knew what Mrs. Watson was teaching me and what I was becoming. And I knew Mrs. Watson was always talking or texting with my mom. And Mrs. Watson started sending my mom more pictures of me dressed up. My mom never complained or acted differently towards me. She would send back texts like, “Oh, so cute, Honey,” or “That looks adorable on you.” She sent one text to Mrs. Watson that said, “I never knew my little boy had such nice-looking, sexy legs, especially in those beautiful stockings you bought him!” It made me feel better and less ashamed of myself.
The next day, Mrs. Watson and I were having coffee together in her kitchen, wearing our nightgowns. She said, “I’m going to invite your mother over for tea next weekend, and I’d like you to serve us, Jamie.”
“Oh, I don’t think I could do that, Mrs. Watson.”
“Of course you can, Jamie. She’s seen how you dress with me. I’m sure she’d love to see how cute and special her sissy son is now. She should see how happy you are now as a crossdresser.”
“If you think she’ll be ok with it, I guess I could try it.”
“I’ll word the invitation very carefully.”
The following Friday night, Mrs. Watson texted my mom: “Mary, Jamie is very special, as you know by now. She and I would like to invite you to tea and cookies with us tomorrow at 1 p.m. Jamie would like to serve us and ‘present’ herself to you.”
There was no hidden meaning in her text. It made me very nervous as I read it. I slept in her guest bedroom that night, and Mrs. Watson woke me early to prepare. She bathed me and shaved my legs in the tub. She laid out the red mini-dress dress that I knew would be tight on me. I had tried it on with her in the store once before, and she liked how it fit on my slender body. She helped me with my sheer, black stockings, which my mom said she liked in the pictures, and attached my garter belt to my stockings. She had me wear pink panties over the top to remove them easily. The matching pink bra was next, and she stuffed two little bra pads into my bra to give me more shape. Then she sat me down at her vanity table for light make-up and did my hair in the pigtail style she liked. She added the bows in the back and gave me bangs in front. She used press-on nails for my burgundy fingernails to match my toenails that she painted last night. She had me stand up and helped me into the dress. She also brought out the black high heels I wore in the picture. To finish my look, Mrs. Watson added big silver hoop earrings.
I didn’t want to admit that I felt girly and cute. My erection showed otherwise. I was pushing out my panties and the front of the dress. Mrs. Watson said, “Oh, we can’t have that! Come over to the sink here.”
She stood next to me in front of her sink and lifted my dress above my panties. She said to me, “Step up on this little step stool and pull down your panties.” I took them down while she held my dress up.
“Jack off in the sink, Jamie, before your mom arrives.”
I’d masturbated in front of Mrs. Watson plenty of times, but it never stopped being exciting, especially like this, a new experience, in front of a mirror with her next to me, over a sink. I pulled down my panties, and my erection sprung forward. She was smiling as we locked eyes in the mirror. I gripped myself and started to jack off.
Mrs. Watson said, “Oh, Jamie, you’re so adorable! I love watching you play with your penis! Cum in the sink.”
I spurted out into the sink.
Mrs. Watson said, “That should settle your penis back down into your panties. Let’s go downstairs and get ready for your mom.” I tucked myself back into my panties.
At exactly 1 p.m., there was a knock on her door. Mom was right on time. Mrs. Watson invited her in, and they sat at Mrs. Watson’s kitchen table. Mrs. Watson said, “Jamie, we’re ready for tea.”
I was nervous, but I walked around the corner and showed myself to my mom. I stuttered, “I’m sorry. Please don’t be upset, mom.”
“Oh, Jamie, I’m not upset at all. I’ve always felt this is what you’ve wanted, and of course, I’ll support you, Honey. You look adorable, Sweetheart. Please don’t feel ashamed.”
Mrs. Watson said, “Tell your mom how you feel.”
“Mom, I feel feminine…girly. Like this is how I am supposed to be.”
“I can see that, Jamie. And you look very pretty, Honey. Your lipstick, earrings, fingernails, even how cute Mrs. Watson did your hair. You see why I wanted you to talk with Mrs. Watson a few months back. You know her husband was a crossdresser.”
Mrs. Watson said, “Jamie, I know that was hard for you, but you don’t need to feel ashamed. It takes a lot to come out to your mom this way. Don’t you feel better that this is out in the open with your mom now, as the sissy you are?”
“Yes, it feels good that my mom accepts me.”
With shaky hands, I served the tea to Mrs. Watson and my mom and brought out the cookies we had baked together last night.
My mom asked me, “Do you like serving and catering to us, your mom and Mrs. Watson, as a sissy?”
“Oh, mom! Yes, I do.”
“Would you like it if I allowed you to dress at home as a sissy, and you could serve me?”
“Oh, Mom, yes!”
“You’d have to do womanly chores, laundry, cooking, cleaning. Would that make you happy to do those things for me? Cleaning in your sissy clothes? Washing my panties? In front of your mother?”
“Omg, Mom, yes, yes!”
“Jamie, Mrs. Watson says you paint her toenails.”
“Yes, Mom, I do.”
“Would you like to paint mine?”
“Oh, yes, Mom, I would love to!”
Mrs. Watson said, “Jamie, why don’t you show your mom what’s under your pretty dress? Come over here, and I’ll unzip you.”
“Mom, please don’t be upset. This is what I wear under my dresses and skirts.” I stepped over near Mrs. Watson and turned around so she could unzip me. She pulled my zipper down, and my dress fell to the floor. My mom’s eyes opened wide as she saw me in my feminine undergarments. I faced her and felt my penis rising in my panties.
Mom said, “Jamie, I’m not upset. You should be wearing panties, stockings, and a bra under your dress. And pink panties are so cute on you, Honey. Those nylons, garter belt, bra, and panties with those heels make you look so sweet! Are you wearing pads in your bra? Are those the nylons with the back seams I saw you wear? Turn around.”
My penis pushed my panties out further. I turned around so Mom could see me from behind. “Yes, mom. Do you like them on me?”
Mom said, “Yes, Honey. Very sexy! Very sissy! Very vintage-looking stockings. Your legs look better in nylons than mine!”
I blushed. My mom has great legs. “I don’t think so, but thanks, mom.”
Mom said, “Sissy-dear, your panties are pushing out in front.”
Mrs. Watson said, “She had that problem when she tried the dress on in the store and upstairs earlier today. We can fix that if you want to go publicly with her.”
Mom asked me, “Jamie, is that something you think you might like to do? Go out in public with me, dressed like this?”
“Oh, Mom, I don’t know if I’m pretty enough for that, but maybe it would be so exciting when people don’t know us. Maybe just shopping together or going to a movie?”
Mrs. Watson said, “Jamie, about that…isn’t there something else you wanted to do in front of your mom? Ask her.”
“Oh, mom, please, please don’t be upset with me…please…”
“Mrs. Watson said, “Tell her, Jamie. You’ve come this far.”
“Mom…this is so embarrassing even to ask you…”
“Tell me, Jamie. I’m here for you.”
“I want to…to…masturbate in front of you!”
“Oh, Jamie, that’s sweet. You can. I’m not upset with you asking me that. I don’t want you to feel ashamed about your sexuality or masturbation. I know you’re a virgin, and girls have rejected you. Masturbation is a natural and normal, and safe outlet for sissies like you. I know you’ve been masturbating in your bedroom alone with my panties. I’d rather you be open with me about it. If it excites you to do it before me, I want you to. It will be very private at home with me or when you visit Mrs. Watson. I won’t be upset when you ask me to masturbate in front of me. I promise. Do you want to show me now?”
I was feeling ashamed but comforted by Mom’s gentle words and understanding. “Yes, mom, I do. My penis is so hard being dressed in front of you like this.”
Mom said, “I know you’re excited, Sweetie. It’s ok. Go ahead, Jamie. I’m ok with this. I want you to. Pull your panties down, Honey.”
I took my panties down to my thighs.
Mrs. Watson said, “Doesn’t she have a cute penis, Mary?”
“Oh, I’ve never seen her erect little penis before. She’s smaller than I thought. And all shaved now, too.”
“Less than 4″, Mary.”
Mom said, “Your father was not that small. I can see why you don’t want to be embarrassed in front of other girls or go on dates with them. Do you think you might want to start dating boys?”
“Omg, mom! No.”
“It’s ok, Jamie. I was just being curious. Turn sideways. Let me see how far you stick out.”
They both started referring to me as “sissy,” “her,” and “she,” which only excited me more. I turned to my side so Mom could see how I was sticking out. Mrs. Watson went to her kitchen cabinet, brought out a small bottle of Virgin Olive Oil, and told me to open my hand. She poured a drop into my hand, then brought out her kitchen mop bucket and placed it in front of me on the floor.
Mom told me, “Play with your penis. You said you wanted to do this in front of me.”
Mrs. Watson said, “Jamie, it’s okay. Show your mom. Jack-off, just like you do with me. Hold your balls. Stand over the bucket.”
I put my oily hand on my hard penis, cupped my balls, and began jacking off.
My mom said, “That’s it. Mmmm…that looks so good, Jamie. I love your sissy look, your little sissy penis, dressed so nicely, standing in front of me, jacking off. Show me how you masturbate. Don’t stop.”
I had my mom’s approval, and both ladies were watching me intently, increasing my arousal. I felt so incredibly sexy and feminine. I let my hand glide over my boner. It felt so slippery and wonderful. I cried, “Oh, oh!” and entered the bucket.
Mrs. Watson came over and brought me a wet towel to clean my hand and my penis. Mom came over, pulled up my panties, and kissed me on the cheek. She said, “That was very special, Jamie. I’m glad you trusted me. You don’t need to feel ashamed when you want to jack off in front of me. I understand, Sweetheart. I haven’t been able to give you much guidance in your life, and without a father to influence you, you’ve patterned yourself after me. You’re a sissy now and feel the need to be humiliated. I understand, and I want to be here for you now. I want to be here for you when you need to masturbate in front of me and your need to have me make fun of your little penis, just like that girl did on your first date. I understand now. Mrs. Watson helped me to understand you, Jamie. Maybe you’d like to masturbate on my feet after you paint my toenails?”
“Omg, Mom, I would love that!”
“Now, why don’t you put your pretty dress back on and have tea with us?”
—————-
A few days later, I was visiting with Mrs. Watson on a Saturday, like I usually do. I was dressed in lingerie for spending a casual day with her, a babydoll nightie with panties and stockings. We were in her bedroom together and I was sitting on her bed. Mrs. Watson stood up. She was wearing a wraparound skirt. She began to slowly unravel it from her waist. She said, “Jamie, do you remember me telling you how happy Earl and I were together?”
“Yes, of course. You mentioned him often.”
“Well, I want to let you know that you can be as happy as Earl and I were…” Her words stopped as she unwrapped her skirt and revealed a beautiful, hard, 5″ completely shaved cock and balls. She lightly stroked it pointing it towards me. Then she continued, “when you find a loving man like the way Earl loved me.”
I was shocked. I honestly never suspected this. I’d been with Mrs. Watson for months. But I realized how beautiful she looked, more so than ever before. This “woman” facing me with a beautiful hard, rather petite cock in her hand. She had two tiny balls snug just up under her cock.
“Jamie, your life can be wonderful, like mine has been. I’ve lived like this for over 30 years and Earl was with me for over 25. Your mother thought Earl was the crossdresser. He never was. I was. I had my boobs implanted, some facial work done and began taking hormones many years ago. It stunted my testosterone levels but as you can see, I still have a nice penis, even if it is on the small side. My balls shriveled from the hormones but they’re still cute right? I could hide my little package nicely in my panties and Earl liked my smaller size. After all, he was the man in our house. And I was a ‘wife’ to Earl in every way. He made me feel womanly and beautiful all the time. You can feel the same way, Jamie, when you meet the right man.”
I think my jaw was still wide open, in shock and awe of what I was seeing and hearing. Mrs. Watson kept lightly stroking her “girl cock” as she talked to me.
“Jamie, your mother was one of the few people who knew about me. She noticed your tendencies at home and asked me to speak with you. I worked as a secretary in an office every day and no one ever knew. I loved wearing my panties, bras and stockings to work every day. Jamie, this can be your life too.”
I looked down at the floor.
“Jamie, don’t be ashamed to be who you are. You like feeling feminine. Doing the cooking and cleaning and the role of the classic housewife. Wearing female clothes. You could have this life. A life like I had. You’d like that wouldn’t you?”
“Umm…yes.”
“Jamie, Look at me. You like what you see, don’t you?”
She walked towards me as I was still sitting on her bed, her cock jutting out from between her legs, holding it, pointing it at me.
“Umm…yes, I like it. You look wonderful, Mrs. Watson.”
“And this can be you.” She paused and then said, “Jamie, I want you to suck my cock. I haven’t had my cock sucked since Earl passed. Suck me, Jamie. Open your mouth, Sweetie.”
Mrs. Watson stroked herself right in front of my face. She always looked pretty to me but now she looked amazing, hold her cock in her hand. I never expected this!
“Take me in your mouth, Jamie. Open your mouth.”
Her cockhead was big, and I had to open wide. She held her cock at the base. I was nervous but I opened my mouth and Mrs. Watson smiled and slipped her cock in.
“That’s right, Jamie. It’s nice, isn’t it? Just slide your mouth in and out over my shaft. Nice and slow. In and out.”
I wrapped my lips around her and gently sucked. I could feel her hardening in my mouth. Then she started moving back and forth slowly, in and out of my mouth. She started moaning as I sucked her cock.
“Oh, Jamie. This is so good. I need this. I miss Earl so much. Lick my sweet little balls.”
I held her hard cock in my hand while she moved in closer so I could lick her cute little balls.
“Oh, Jamie! That’s great! Tell me you like it. Tell me you like having my cock in your mouth.”
I was licking Mrs. Watson’s balls. “I do, Mrs. Watson. I had never thought of you having a cock between your legs. But I do love this!”
“Oh, that’s good, Honey. I knew you would. This is so good. I want you to enjoy my cock. I’ve been waiting for you to do this to me. I had to wait until I knew you’d be ready for this. Suck my cock, nice and slow, sweet sissy.”
She was moaning, holding the back of my head, pushing her hips in and out, gently fucking my mouth.
“Oh, Jamie! I’m going to cum in your mouth. Breathe through your nose and keep your lips wrapped around my cock. Try to relax when you feel me spurt in your mouth.”
Mrs. Watson began ejaculating in my mouth. It surprised me and I started to pull back a bit. Mrs. Watson held the back of my head to hold her cock in my mouth and told me, “Don’t stop, Jamie. When I cum, I want to finish in your mouth.”
I swallowed some of Mrs. Watson’s jizz and the rest ended up around my lips and mouth. She pulled out and told me I was a good girl for her. I wiped my lips with my hand and sat in shock, realizing what I had just done.
————–
Afterwards, we were having tea in her kitchen and I asked her, “Mrs. Watson, can I just stay with you always?”
“No, Jamie. I want you to still suck me, but I’m much too old for you. I’ve brought you along about as far as we can go together. Now I want you to find a nice man, like my Earl was to me. Jamie, you’re pretty enough to go out in public. On dates with men. You could find a sweet man, like my Earl was. He loved sucking my cock. You can find a man like Earl who will love you as the sissy you are and sucks your little 4-inch penis and fucks you. And you can suck his cock. I can help you find someone nice online. There are dating sites that cater to “girls” like us. We’ll just need to get you a vocal coach.”
“Couldn’t you fuck me, Mrs. Watson?”
“No, Jamie. Your virginity should be taken by a real man, and you should be fucked by real men. But I might know someone who could help with that when you’re ready. He was a friend of Earl’s and played with us sometimes. Older gentleman and I’m sure he would be very gentle with you. He’s a good 6″ and quite thick. I could be there with you and help you through it.”
“Mrs. Watson, will me ever suck me?”
“No, Jamie. I only suck real men. But you can still masturbate with me after you suck me off. Do you want to now?”
Mrs. Watson smiled and brought out the bucket.
I stood up and pulled my panties down…
To Be Continued…?
*This story has been edited by AI to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.