Staying with Mrs. Wentworth Day 01

This is my first story and it develops a little slowly. Some people don't like that but I like a slow development. I hope you do to. It is obviously meant to be continued so if you have suggestions about things, I'd be happy to hear them and maybe make changes to make the story or characters better. I hope you enjoy this situation.

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I'm 18 years old and should be old enough to stay by myself for a week when my single mom is off somewhere. I don't know why she can't see that. I heard my mom talking to her friend, an old teacher of mine.

"Doris, I know he's 18 but I can't leave him alone. I don't think he's prepared. He's sort of a young 18, really. I really appreciate you taking him in while I go away. I'll drop him off tomorrow afternoon on my way to the airport."

I fought with my mom over this but she was always over protective. I might not be the most experienced guy and she didn't exactly encourage independence but when a guy's 18, he doesn't want a babysitter, right? But my mom insisted. "You'll stay with Mrs. Wentworth and I won't worry about you while I'm off on my business trip. This is not open for discussion."

Not that Doris was a babysitter. Mrs. Doris Wentworth was the old lady who had been my teacher in fourth grade. There wasn't a Mr. Wentworth. In fact, I don't know if there ever had been. Maybe that's why she and my mom got along. Neither had a husband. She was an old lady who was always nice. Now I say old lady but really she just seemed old when I was in fourth grade. That was nine years ago and she was probably in her later 30s. She was in her forties and actually looked pretty good for her age. She was in good shape, dressed nice and was always nice to me even when she tutored me in high school. She might be kind of old, I thought, but she was nice.

When Mom dropped me off, Mrs. Wentworth lived more than an hour away but on the way to the nearest big airport. I took in a suitcase with some clothes and Mom talked to Doris. Doris teased her about her trip and told her to be a good girl and try not to get in trouble. Then they both laughed in a way that made me uncomfortable. I think they were probably talking about sex or drinking. I knew my mom probably had a sex life but I didn't think about it much. I did think about sex itself a lot. I was 18 and as horny as any 18 year old you'd meet. I thought about sex day and night. I didn't have much experience at all first hand but it didn't stop me from having a fantasy life.

Then mom got serious and gave me a kiss but it was like when she was going out and I was 12. I was an adult now and she didn't treat me like one. "Now, Stephen, you be a good boy and listen to Mrs. Wentworth. While I'm gone, she's in charge of you. I will be very angry if you're a bad boy. You listen to her, help her out, do anything she tells you to, and show her how nice and obedient you are. Make mommy proud and be a nice young man." I felt like she didn't notice I was a grown man. I was an adult not 12.

"Aw, mom, c'mon. You're embarrassing me. I'll be fine. I would have been fine at home and we're not even near any of my friends...."

"Stephen!"

"All right, okay, I'll be fine. This will be fine. Everything's fine. Don't worry. Have a good time."

Mom smiled. "That's better, but it's not to have a good time, I'm just going because I have to go for work"

Doris smirked and Mom gave her a dirty look.

But Mrs. Wentworth put her arm around mine and said "Don't worry, Stevie and I are old friends and we'll be great. Run along or you'll miss your plane." I didn't like being called "Stevie" but I liked her attitude and we watched mom go.

Then Mrs. Wentworth told me to grab my suitcase and led me up the stairs to my room for the week. Following her, I realized she wasn't that old really and actually had a nice ass at least how her skirt which was a little tight cupped it. I kind of liked following her even if it was weird to like looking at the surprisingly tight ass of the "old" lady who was my ex-teacher. We walked past a big bedroom which was hers, really nice with a giant bed with posts and then down the hall to the room for me. It wasn't exactly masculine, like no sports pictures or anything definitely manly but at least it wasn't pink or girly, just kind of blue. I put my suitcase on the bed and she told me she cleared out half the dresser for me. But it isn't like I had a lot of clothes so I just put the suitcase on the floor when she said "come down to the kitchen when you're settled."

I walked out maybe 60 seconds behind her, pretty much "settled." She smiled in the kitchen and had me sit at the table while she gave me lunch.

While she cooked some soup and made a sandwich, she talked about how nice it was to have me and how it was like playing house. Then she laughed. I laughed too but mostly I stared at her ass the whole time. I liked it and I noticed every time she bent down (and she bent down a whole lot of times, a lot more than I hoped for) I could see the lines of her panties bumping out. I liked that. When she gave me lunch, she put a plate in front of me bent over and I noticed from my angle her blouse wasn't real closed. I mean I could see in and saw a pretty good look at a black lace bra. I didn't expect that. I was surprised and tried real hard not to react even though it made me hard. She didn't notice me staring down her blouse and I thought it was probably an accident. But we had a nice late lunch and just talked about how things were going with me. I hadn't started college and didn't know what I wanted so we mostly talked about that.

Then she grabbed my hand across the table and held it (which I liked) and said "now, sweetie, I hate to do this and run off on you just as we've started our little time together but I have to go out to a charity dinner as a favor to a friend. I didn't know you were coming yet when I made this date but I won't be late I promise." Then she laughed at me, I guess I looked funny. "Oh sweetheart," she patted my hand. "Are you jealous? It's not a real date, I'm just going with friends."

I don't know why she said that so I said "What? No, of course not. What do you mean jealous? Oh you're kidding. No, I don't care what you do. I'll just hang out and do whatever." She smiled and said "that's a good boy. I promise I won't be late. I'll be home by 9:00. You can hold me to that. I don't want to be spanked for being bad so I won't be late." Then she laughed again. "Now I have to go get ready so you make yourself at home. Think of this as our house for the week." And she went upstairs.

It was really weird. I didn't think I looked jealous. That would be stupid. What do I care what some old lady I'm staying with does? And what the hell did she mean getting spanked? That was weird. Probably some older person joke. It wasn't like I'd let her spank me if I was late. And did she think I would bend her over and spank that gorgeous ass of hers? Ridiculous. I sat there thinking about it for ten minutes, though. That was weird but thinking about it was at least a little sexy.

I heard her up taking a shower so I guess she was going to change to go out. I wandered around downstairs realizing I couldn't call anyone and have them come over or anything. We were way far away. Not that I did a lot socially on a normal week but I was feeling sorry for myself. I looked around the backyard, couldn't see any neighbors or anything, just a lot of land. I was turning on the TV when she came down stairs and called out that she was going to go. I turned and was speechless. She stood there smiling.

She was wearing a really red tight satin dress. It was shiny and it hugged her. You could tell she had a nice ass and I saw she had a nice figure everywhere too and nice breasts. I couldn't believe I was noticing this about a lady who was even older than my mom. But she was very hot and the dress made her super hot. I just stared and found myself wondering what was under it and how come I never noticed how hot she was. I mean maybe in fourth grade I sort of liked her like a kid likes his teacher but wow! She asked me if it looked OK? It did but I just nodded not able to speak. "Oh, are you sure Stevie dear? You look surprised. Is it the wrong style for an old lady? Do you hate it?"

"Gosh no, Mrs. Wentworth, it looks amazing and you're not old or anything. You look awesome." She smiled and said, "aren't you the sweetest little guy?" Again I liked the attention but both she and my mom had a way of making me feel 12. I mean what adult 18 year old wants to be called a sweet little guy?

I was kind of hard and horny because I was 18 and always horny actually and I had just realized that whatever else happened she was totally hot for a woman her age. Hell, in that dress she was hot for anyone. I didn't want to just sit on the couch and play with myself so when she left I decided to explore. So I walked around. It was a pretty big house. But very orderly and not messy at all. There were a lot of books but whatever I felt like doing, reading wasn't it. I walked into her room. I felt kind of weird, sort of forbidden like it was a private place I shouldn't be. Which it probably was. She was very neat and nothing out of place with her bed completely made. I did open a drawer or two and even one with her panties in them. I looked them like they were a basket of jewels. And there were lots of colors and they weren't boring. But I was afraid to touch because everything was so neat.

So I wandered in the bathroom. This was a little messier. But not a lot. A hairdryer was out and the tub was wet still but it was a hell of lot cleaner than mine at home. Then I saw the black bra I had stared at earlier laying on the floor. I picked it up and stared like it was magic. I have a total thing for women's lingerie. It's so erotic and mysterious. It was very feminine and it was black which made me hard. Lingerie always turns me on so since I was alone I actually unzipped and let out my cock. I didn't have much real experience with women but I masturbated lots of times.

I pulled the bra and back and forth across me to feel it against my skin but was about to leave when I saw the panties. They matched. I picked them up and smelled them. I could smell a hint of perfume and her on them. I tried not to but I grabbed them and started jacking off even though I knew I shouldn't. In a few minutes, more like 45 seconds, I grunted and shot a load, catching it with the panties. Oops. I looked at the pool of white cum caught in black silk panties. I liked it and liked doing her panties like that but afterward kind of thought maybe I shouldn't have done that. So I wadded them up and found the dirty clothes hamper and pushed them down under stuff. I threw the bra in too and figured she wouldn't notice.

I knew I was a perv but I felt better because I came. She wouldn't know and I'd be more relaxed. But quickly I left her room after rinsing my dick off in her sink. I went back downstairs and watched TV. I just watched ESPN for a while to get my mind somewhere else. I figured she'd actually be pretty late. No way you go out looking like that and get home at 9. But I was wrong. I heard a car outside at 8:45 and then the garage door and hear her come in. In the family room, I was in a chair and hear her heels making clicking noises slowly across the floor as she walked through the kitchen and dining area and finally came into the living room, leaning against the doorway and looking just as awesome as when she left.

I sat in a chair with my feet in front of me on a stool and looked at her and just stared. I didn't say anything for like a minute and then I just said, "uh, hi." She was standing there leaning against the doorway with one hip out. Her legs looked awesome between the heels and some white stockings. I hadn't notice every detail before she left but wow she looked like some fantasy woman in shiny satin. It was only a couple hours since I had used her panties to get off but I was instantly really hard in my pants.

She looked at the clock and said "not even 9 yet and I'm home, that was the rule and I followed the rules. It's good to the follow the rules isn't it Stevie?" Then she walked into the room slowly and stood at the edge of the chair looking down on me, smiling, and making me a little self-conscious. "Um, yeah, I like rules. Of course. So did you have...."

But she interrupted and told me to sit up, reaching down and tapping the bulge I wasn't hiding. "Sit up and cross your legs sweetie-pie. You need to be more discreet about some things."

I turned super red and sat up and crossed my legs to hide myself. I was more embarrassed than I'd ever been but I didn't know what to say. "I'm sorry," I mumbled.

She sat on the stool I had just been using and patted my hand again. It made me feel little. "Don't be sad my little sweetie. Mrs. Wentworth is just trying to teach you like I always do. You were always a good little student and I know you'll be a good boy if someone just shows you what to do. I know you'll be a good for me won't you? Are you my good little student, sweetie?" She smiled at me and I nodded. But she kept looking. "Say it Stevie dear. Tell me"

I wasn't sure what was going on but I said what I thought she wanted. "Yes. Sorry. Yes, ma'am. I'm your good little student." She smiled.

I looked down kind of embarrassed. She was turned with her legs crossed so I just stared at her legs. I watched them from her heels and all the way up noticing that her legs the way they were pointed sideways made her skirt high. I could see all the way up her thigh and to some white lace band at the top of a stocking. She didn't notice how much she was showing I guess. It made me harder to see it and to know that it was an accident but I kept my bulge hidden.

She smiled, half stood, leaned over and kissed my forehead. Then she stood and said "OK, now it's bedtime. We have a busy day tomorrow." As she walked away, she stopped and looked at me and it was clear she meant bedtime for me too. It wasn't even 10:00 yet. But I followed her. She walked slowly which I enjoyed from behind. She took the steps real slow I guess because she was still wearing heels which she really should have taken off to climb the stairs but I loved it. I'm surprised I didn't cum in my shorts.

She went into her room and stopped me before I could keep going. "Stevie, dear, remember about helping me like mommy said...."

"Uh ok, sure." What now? I thought. And I wish she didnt say "mommy" like I was some kid.

She stood in front of the dresser looking in the mirror and said to me "Mrs. Wentworth can't reach her dress's zipper. Be a good little dear and help unzip me. I'm sure you help your mommy that way too."

That seemed really really weird to me but I wanted to be helpful so I reached and carefully pulled the zipper down. I realized that I could see some skin and her bra straps from the back and I was going a little lower. But then she dropped something I think because she suddenly bent over and down to the floor. I lost my grip on the zipper and her backside pushed out so that her beautiful satin covered ass pushed back into me and against my rock hard bulge. Just for a minute and then she stood back up. I finished unzipping a few more inches down. But I could see the top of red panties and also what I figured out was a white garter belt. I had only read about those and never seen them in person but it was hot. It was funny that her bra and her panties were both red like the dress even though no one was going to see them. Well, almost nobody because I saw the back of them at least. It was a lot more erotic to me than it would have sounded.

She turned around, her dress still up but loose, and kissed me very softly near my ear. "Thank you for being my good little helper, now run off and put on your jammies and get into bed." I was confused. It was sort of seductive and sort of belittling. And it's not like I wore "jammies" like some kid. I wore shorts and a T shirt and I got into bed. A lot of nights I jerk off thinking of someone my age named Julie but tonight Julie was replaced by Mrs. Wentworth. It was weird but I came pretty fast and fell asleep and slept great wondering what tomorrow would be like.