This is actually the fourth part of the Staying with Mrs. Wentworth series. You might want to read the day one through day three parts first. This is also slow developing and maybe longer than it should be. I'm really enjoying the characters so I got a little long. I'm a new writer though so any feedback is always appreciated.
I woke up later than I intended. It was the latest I had slept at Mrs. Wentworth's. I was starting to feel at home in my bed in the spare room. I almost didn't remember how mad I had been when my mom made me stay there while she went away. I mean what 19 year old (almost 19) wants to be forced to be babysat or watched over by some old lady who used to be his fifth grade teacher? But I didn't mind anymore. After all, Mrs. Wentworth was really nice and actually kind of hot for a woman her age. And actually her age wasn't that old. She was maybe 40 which isn't exactly old. And she treated me like an adult which after all I was. Most of the time anyway.
Other mornings she had woken me up but today I just slept through. It was already 9:30 and I was looking forward to seeing her. Actually, I was curious and nervous about what I would say but also looking forward to it. After what had happened the night before, I thought things were going to be really different. I mean she actually pretty much gave me a blowjob which changes things, doesn't it? (See the story in Day Three of this series) I hadn't been super sexually active in the past and it was probably technically my first blowjob. So I didn't know the next thing to do but I was sure we'd figure that out together. I was pretty sure we were going to talk about it and just go from there.
Anyway, I got ready and got dressed pretty fast to get downstairs as soon as I could. However, on the way past her room I stopped and saw her laying in her bed. I went in and looked around not sure if I should wake her. After all it was pretty late for her to still be asleep. She woke me up at 6 the first morning and it was almost 10 today. She was sleeping and her clothes from last night were on the floor. The pajama shorts and top she had been wearing, with the addition of a few dried stains that gave me happy memories, were laying there in a pile on the floor of her usually really clean room.
I was thinking about whether she was naked under the covers and how to find out when she woke up, saw me and sat up in bed with a big smile. She wasn't actually naked and had a blue nightgown on so I was disappointed. I guess she had changed after everything had happened last night. I smiled back and tried to figure out what to say. I guess "thanks for sucking on me" would have been a bad choice but I wanted to say thanks. While I was trying to figure it out, she saw the clock and said "10:00? Oh my goodness! I never sleep this late. Oh my sweet Stevie dear, you have to forgive me, I think Mrs. Wentworth made a big mistake last night."
I was a little shocked and said "well, I don't know about that." But she shook her head and said "yes, sweetheart, I set a bad example. I had much more wine than I should have. I'm sure I didn't do anything crazy because we didn't go out anywhere but I don't remember a thing that happened after the girls left and my head is aching. I'm sure I wasn't very good company and I'm sorry."
I didn't know what to say. This was weird. Maybe it all just happened because she was drunk. Wow, that wasn't what I expected but I couldn't exactly remind her of it. Instead I just said, "No everything was fine. You know we saw a movie and we went to bed early. I didn't even notice you were drunk. I don't mean that you were drunk, just sleepy or whatever."
She smiled and said "How sweet. Always the perfect gentleman. I'm so lucky to have found you. Now be a good boy and run along so I can get dressed and I'll make us some breakfast." So I went downstairs and did some thinking. It was like she was two different people sometimes and I was never positive which one was going to come out. Still I guess it was nice to be called a perfect gentleman. Not that she "found me." My mom brought me over. And while she did make me feel like an adult sometimes, at other times her language was a little funny. Be a good boy and run along isn't exactly what some guy wants a super hot woman to say. Finally it was weird that she didn't remember the most memorable thing that had ever happened to me. Oh well.
I was downstairs making a big pot of coffee because I knew that coffee was a good thing after drinking. That's what people said. When she came down, she was really happy to see coffee and gave me a huge hug and a big kiss before telling me "you're just the sweetest thing taking care of me like that." It wasn't sexy but it made me happy. She drank some coffee and took a couple pills but seemed to recover pretty fast while she was making us eggs and bacon. So I set the table and she brought stuff over and we ate.
It was usually morning when she asked me embarrassing questions so I jumped in first to avoid them. "Um, Mrs. Wentworth, are you on vacation or do you have to go to work soon? I mean I hope you aren't staying home because of me. After all, I'm an adult and don't really even need supervision. I don't want to be the one making you not go in."
She smiled again and leaned across and squeezed my hand and told me "you're such a sweetie-pie to think of that. Please don't worry, honey. I don't have a job." I looked surprised and she quickly explained. "Darling, I did teach for a few years but I think you were in my very last class. The late Mr. Wentworth didn't live very long but he did make a lot of money. When he went, he didn't have any family, just little old me. I finished out that school year and I haven't needed to work since. I'm glad because it gives me so much more time to spend with my dear, sweet Stevie."
That explained a lot. I didn't ask how much exactly she was worth but I guessed that her dead husband had made a lot of money because she seemed pretty loaded and had a big house and a real expensive car.
"Now, enough about that, Stevie. I have to ask something important." That made me nervous. "Sweetheart, I want to ask you to do something for me, well with me really. A lot of men, I guess a lot of people I should say, don't like to do it but I think you should experience it and you might even like it. I know I will like it and I think you will like it. In fact, I'm pretty sure you will, a giving young man like you. And I can walk you through it all because you won't be familiar with doing it and obviously I am very familiar. But it would make me happy if you and I can do it together. That will be fun won't it?"
I was pretty sure I knew what she about to say and I wanted to play it cool. So I waited while she continued. "After our pretty little date at the restaurant and how nice it was, I thought you might be willing to try this. I know it will be fun for both of us. I'm a little embarrassed to tell you but I've been thinking about it and looking forward to showing you since before you came here to our house."
She smiled at me and actually I had a huge erection under the table. I was all set to crawl under the table right there if she was ready. Maybe she wasn't really a completely different person in the morning. I guess she really did remember too and this was the next step. It only seemed fair like the obvious thing after last night. "Sure, I'd be happy to do anything for you, Mrs. Wentworth," I said. She was very surprised and very excited I said yes. I can't believe I would ever say no even if it wasn't something I had dreamed of doing or tasting. It was partly a fantasy, obviously, and partly an awesome sexual experience I had thought a lot about in the past. I think I'd have done anything for her right then. I knew I really liked her even that quickly and I just got a kick out of seeing her happy.
She stood up and pulled me to my feet. Obviously doing stuff under the kitchen table wasn't exactly classy. It wasn't how a classy lady like her would start her first time with me. She hugged me even though I was pretty hard right then. I'm pretty sure she didn't mind a huge tent in my shorts this morning because we were actually talking about more advanced things. Considering what we were about to do, it was fine to be really worked up.
"Now I need to figure out what to wear. This is a special occasion. And we need to decide what to put you in too. I want us both to look just right." I never thought a lot about clothes. At least my clothes. I noticed everything she wore and all the details of her underwear and her shoes and her dresses. I had spent a lot of nights staring at catalogs and the real thing was better. But I never thought what I wore mattered a lot. But why not, right? I know I was definitely extra turned on when she wore the right stuff so it made sense that she might want me to wear something special because we were talking about her getting turned on. I was okay with that. I just didn't know if she meant funky underwear or we were talking costumes or something kinkier.
But whatever it was, I was up for it. "Mrs. Wentworth, whatever you want is okay with me. Anything at all." She giggled and playfully swatted me on the butt. "Careful what you say young man, ha ha, I just might test you." And she laughed like she told a joke. "Okay, darling, now obviously I'll dress up from head to toe. I always do. For you, I don't think we need a tuxedo. A lot of men wore business suits last time I was at the opera so we'll work with that."
I'm sure I looked really puzzled because she stared at me and I mumbled "did you say opera?" She looked and laughed and said "didn't I say that before? That's so funny, Stevie. What did you think? You didn't think I just meant some boring movie, did you?" Well, I didn't tell her what I thought but I did turn red and said "No I didn't really know. I mean I wasn't completely sure. And, well, I've never been to the opera."
She hooked our arms together and led me up the stairs side by side up to her bedroom. "I won't waste our time on silly movies. I really think you'll have fun with me at the opera and I know we talked about how you don't have a lot of experiences." We had talked about that but usually she meant it in a sex way but I guess not always. "And I know I'm your teacher right now. I want to give you more experience so we can have another fun date night. Maybe not exactly the same as the last time though, right honey?"