I meet a mature woman in the complex I lived in and showed interest in me.
At 19 I haven't had sex yet but I did jerk off to pin-up nudes in Playboy a lot so I kinda knew a little bit about sex. But Miss Baxter showed me things I had no idea about.
Miss Baxter was in her late thirties I'd say. She had an hourglass figure, a slim waist and very nice breasts. Not married and has no kids. She lived alone and didn't talk to people that much. She wasn't a crazy cat lady type even though she did have a cat. She was the typical mother type without kids if that makes sense.
She was about 5'2 and 110 pounds. She had red hair and bright green eyes.
I couldn't understand why she was single then one day she asked me to come talk to her.
I thought I was in trouble for something but thought I could easily get away from her if she tried grabbing me or something so I went up to her.
She said you look like a strong boy, can you help me move something inside.
Now my mom always told me to never trust strangers but it was the middle of the day and lots of people were watching so I said sure.
She had me help her rearrange her living room.
An hour or so later she gave me $20 and thanked me with a kiss on the cheek.
As the spring went on she had me do more things for her and always paid me with cash and a kiss.
One day on a Friday she had me move some things from her bedroom to the main floor, she told me she would move it the rest of the way to the basement herself.
I took it upon myself to take it into the basement. What I saw shaped me sexually for the rest of my life.
The windows were blacked out. In the middle of the room was a steel four-post bed with handcuffs and ropes. The walls had all kinds of things, whips, rope, straps, chains, sex toys, wigs, girl's clothes, lots of heels and boots of all kinds and colors, and make-up. All kinds of things that just didn't seem to fit with what I thought Miss Baxter was.
So you found my playroom, I see Miss Baxter said.
I'm sorry Miss Baxter. I shouldn't have come down here, I said.
Nonsense she says with a grin on her face. I was really hoping you would come down here.
Embarrassed, I just stood there looking around.
Everything seemed to get extra quiet except her heels that she always wore, even in the condo. Now that I think about it that was a bit strange.
She made her way past me, curling her finger under my chin seductively.
I have a confession, she says. I've been watching you for some time now.
I turned red quickly at this point. She just laughed and said I was so damn adorable.
Do you like girls she asks as she slowly walks around the bed, her heels clicking on the concrete basement floor?
I.. I like girls, was my embarrassing response.
Good, have you ever thought what it would be like to be one?
No, I mean not really.
Come on now, I know when you're lying to me you know.
Thinking of me trying on my mom's underwear and how it made me feel I said well sometimes.
You know what happens down here stays between us. I promise never to tell anyone. Do you promise that you'll never tell anyone too?
I thought about it for a bit while I asked her what she wanted to do.
I like to dress good boys up like girls and show them what it's like. It's up to you how far you want to take it.
Have you done this before to other boys?
She just smiled and said she can't tell me that because of promises she made.
That meant yes. Now I was thinking of all the boys in the neighborhood and Wondering which one was her last plaything.
Okay, I'll do it. I'll let you dress me up. I was thinking maybe getting a girl to help me dress up would be better than trying to figure it out by myself. Boy was I right.
Fantastic, she says. You can move the things from upstairs to this corner and she went back upstairs.
I took my time looking around wondering what I got myself into.
Once everything was done she paid me and kissed me on the cheek as usual.
Can you come by tomorrow, say around 9 am she asks.
Nine am? I like to sleep in on Saturdays after a long week.
The earlier we start the more you will learn.
Okay, I'll be here at nine then I said with a huge smile.
The rule still was you wake up, eat and then outside until the street light came on. It's always been the same. Then I'd better be home or my dad would whoop my ass good. So I set my alarm for 8:30 am.
Mom was already up and working on her second pot of coffee I think. Dad always sleeps in on Saturdays and my little brother did the same.
Mom and I made small talk while I ate quickly then I left for Miss Baxters.
Her door was open which was unusual but I knocked anyway and heard from the depths of her condo, come in and close the door behind you.
I did as I was instructed. I stood still listening for any sounds to indicate her whereabouts.
She said down here.
I went downstairs. She looked much different. She usually wore blue jeans and a loose blouse or a sweater and of course her high heels.
Not today, she wore bright pink heels. Her legs were clad in shiny silky white stockings. A very short pink miniskirt. A bright pink and white corset that made her sizable breasts pop out at me.
My little boner stood at attention immediately in my tight jeans. I just stood on the last rung of the stairs staring at her.
She smiled as she patted the back of the chair at the vanity.
My hand hid my boner as I approached and sat down.
The lights were very bright shining on my face and I couldn't see myself in the mirror as Miss Baxter told me to sit still. She started pulling hairs from my eyebrows. She smelled so nice. Intoxicating really. Before long I seemed to fall into a trance of some sort. She stood behind me and her arms were on either side of me. She worked her magic on my face for a long time, every once in a while, I could feel her breasts touch the back of my neck or my cheek when she was on either side of me.
I don't think I ever had a boner for so long without rubbing one out before.
When she was finally done she had me stand up and look at myself in the mirror.
I couldn't believe that was me. My face looked so soft. My lips stood out the most with a slightly darker pink.
To be honest I was quite taken aback by how beautiful I looked.
So… do you like it, she asks. Oh yes, yes I do. I love this look Miss Baxter.
Good. Now let's pick out some clothes for you to wear. Shall we?
Without thinking I just stood up and followed her to the wardrobe.
She opened it and started flipping through the dresses.
Ah, this one will do. She held one up against me and said perfect.
She put it on the bed. Then she added a bra and panties. Some pantyhose, A long blond wig and some heels.
She stood facing me as she said I assume you know how to put these on, right?
Yeah, I can do that.
She stood there looking at me for a long moment then she went upstairs saying if I needed help to just call.
I sat on the edge of the bed wondering if I really should do this. No one has ever seen me dressed as a girl, but the bra and panties looked so good.
I don't even remember taking my clothes off but I sure do remember putting that blue bra and matching panties on. My little wet boner peeked out to the top. It didn't do that with my mom's panties.
The bra fits really tight squeezing my chest and making it look like I have cleavage.
The blue pantyhose slid up my legs next. The hair on my legs showed a bit. I still had some hair on my arms and legs but my chest was pretty hairless.
The dress was a nice short sundress, blue with yellow stripes.
Miss Baxter called from the top of the stairs asking if I was done.
I told her all I had left was the wig.
She came down to see me standing in front of the vanity admiring myself.
She helped me put the wig on and pin it in place. She stood back and looked me up and down.
Oh my, you're not wearing your heels.
She grabbed them off the bed and helped me into them. I had never worn high heels before and found it a bit difficult so Miss Baxter said let's try something different. She walked over to her shoe rack and picked a different pair. The sound of her heels clicking on the floor made me try harder. The second pair were a lot stiffer and after she had them in place she locked them on me with small paddle locks.
She stood up and told me to practice walking around the basement.
I stood up and she held me up as we practiced walking for a bit. Then she let me go on my own. It felt like the training wheels came off. I felt very unsure about my steps but the more I tried and the more I listened to her instructions the better I got.
After a couple of hours, we went upstairs. She usually had her curtains closed but today they were wide open. I tried to avoid the windows but Miss Baxter would have none of it. She told me she was dressed much more scantily than I was and it didn't bother her. I replied that I was a boy. She pointed to a mirror and asked if I looked like a boy. I admitted I didn't look like a boy but I am a boy. She reminded me that was why she was training me. I relaxed a little after that but still didn't like walking in front of the window. She had me practice walking in heels all over the main floor.
She had me practice how I sat whether it was on the couch or a kitchen chair. She showed me how to position my legs so I sat ladylike.
She showed me how to sip tea and eat sandwiches.
We chatted in the living room in full view of the window. I paid very close attention to anyone that walked by, hoping no one would look my way.
Miss Baxter was right in the end. Nobody cares.
It was getting late and I had to get back home so we went downstairs. She asked me to strip and place everything on the bed. I did what I was asked without thinking about it first. I stood there naked as she cleared her throat. Looking at her I suddenly felt so embarrassed. My little boner was standing tall as usual. She asked if I was like that all the time.
Embarrassed, I told her it was the feel of the panties. It just feels too good. She asked me if I could jerk off while she watched. I wasn't sure I should but after briefly thinking about it I just started. I grabbed it and tugged it hard and fast. She laughed and told me to take my time. I told her I didn't have much time left.
She stood up and told me to stop then. I'd better get dressed and head home. Once I was dressed she cleaned the make-up off my face.
As I was leaving she gave me $20 and a kiss on my cheek. I thanked her. She said the same time next Saturday. I smiled and said you bet. See you then. She smiled as I ran off home.