Staying with Mrs. Wentworth, Day 03

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This is part three of the scenario. I’m enjoying crafting Mrs. Wentworth and I hope you do too. The story and its development are very slow. I should say I have benefitted from a lot of advice from commenters even if the story doesn’t always go exactly like some suggestions. This is my first story and it’s a learning process. I hope you enjoy.


The sun woke me up again and it took me a few seconds to remember where I was. I remembered that my mom had forced me to go stay with her friend Mrs. Wentworth while she was gone for a week. I resented it. I was almost 19 and old enough to live on my own if I wanted but I humored my mom. Mrs. Wentworth was my teacher in fifth grade and that made it more humiliating. I should be on my own not staying with some old lady who used to teach me. Actually, she wasn’t that old really. A lot older than me but probably around 40. And she turned out to be very nice. I wouldn’t admit it to my mom of course but I didn’t mind staying with Mrs. Wentworth. I was starting to like it really.

As the sleepiness wore off, I remembered the events of the night before (see Day Two). I started thinking about everything but mostly about Mrs. Wentworth taking off her dress and laying over my lap in her very nice lingerie and having me spank her for supposedly being naughty. I started thinking and doing what I usually do in the morning which is jerking off. I slipped off my shorts and used them while I stroked to keep from making a mess. I was living in my head the night before and not really noticing anything else so it wasn’t very long before I came and emptied myself. I sopped it up with my shorts and was catching my breath when I thought I saw some movement by the door.

I forgot about Mrs. Wentworth’s open door policy. Her door was always open symbolically she said so our doors shouldn’t be closed to each other. Maybe she walked by or something. I hadn’t noticed anyone but then again I was in another place so would I have noticed if anyone watched? I bet she’d have said something if she saw me there doing my thing. A few seconds later though, I heard her call out “Stevie, honey, are you up?” I had only a split second to toss the sticky shorts on the floor next to the bed and pull up the covers to cover myself.

She came in with an arm full of laundry looking rested and energetic. “Hi, sweetie. I’m just doing a load of necessities so I thought I’d grab a few things from you. Let’s see.” She looked around and I said I was okay but she grabbed a shirt and shorts from the chair and put them in her arm pile and then before I could think of anything to say she bent over and grabbed my fresh shorts off the floor. Her hand must have squished and felt the pretty big load I had sopped up. But she just squeezed it in her hand, looked at me, smiled and kept a tight grip on the shorts. Then she said “come down when you’re ready, dear.”

I waited until I heard her going down then I got up, took a quick shower and got ready. When I got downstairs, she had breakfast going and was pouring me a cup of coffee. “There’s a bagel in the toaster if you want it, I just finished and am enjoying my coffee.” So I got my bagel, sat down and put stuff in my coffee and started sipping it. It wasn’t great because I still was not really used to coffee but it made me feel sophisticated.

I was chewing a bagel when I noticed her looking at me. “Stevie, honey, I know you’re a virgin right now but have you experienced other things like oral pleasures?” My mouth was full so I couldn’t yell at her and say, “what the hell are you talking about?” But I thought when she was pushing the whole virgin thing yesterday, my reaction meant it wouldn’t come up again. But here she was with a total invasion of privacy. When I finally finished chewing, I said “why are we talking about this? You don’t know me and what I do and stuff like that. I do lots of things with lots of people but, you know, it’s private. I mean c’mon!”

I was steamed but also puzzled. I mean this woman was like a completely different person from one minute to the next. In the morning she was one way and at night another and I never knew what was coming my way. Plus I didn’t really like talking too much about how many things I had done or not done. She reached over and smiled, though, not offended at all. She patted my hand and said, “It’s okay honey. I don’t want to embarrass you. I am just trying to help. I know that right now, as of today, you haven’t had intercourse with a real woman yet and that’s fine. It’s a good thing actually. I just didn’t know how far along you were. I’m sure a nice gentleman like you doesn’t like to kiss and tell and you shouldn’t. But sometimes a teacher likes to know her students. Remember you’re my pupil, honey, and Mrs. Wentworth can help. It’s okay though. A lot of boys haven’t tasted a woman yet.” She smiled in a very reassuring way and I didn’t have to reply. I even stopped turning fikirtepe escort red.

Fortunately, she stood up and walked over to the sink so I didn’t have to feel awkward. I stared after her thinking of what to say but instead found myself just staring at her ass pressing against another silk robe as she bent down at the sink. I took my dishes over and was trying to walk around when she backed up without seeing me and her tight silky butt made direct contact with my bulge. She said “oops” and giggled but managed to collide two more times as we tried to get our signals right.

Finally, she walked away and headed upstairs. She called down “I’ll be ready to go in ten minutes.” What? Go where? I didn’t know what she meant. She was going out I guess. But I was wrong. It wasn’t just her.

She came down, dressed like a very nice lawyer or something in a blue business suit which fitted her tightly and whose skirt was over her knee but not much over. She looked great. Not as good as the silk dress but I guess in the daytime you can’t go all out. I was admiring her when she opened the door to the garage and said “I’ll drive today. Let’s go.”

I was going to ask where but I thought she told me before and I forgot or something because she didn’t say. She talked about other things. “Stevie, darling, I’m having the girls over for a late lunch or early dinner.” I must have looked surprised because she said, “Oh I didn’t mention it did I? Three of my closest friends are coming over for tea and light meal late this afternoon. I don’t have anyone to help serve so I thought you could be the waiter. I’ll train you of course but it will be fun. Like having a butler.” I didn’t have any response but I thought, what the hell it’s better than mowing the lawn or doing something else. I said, “oh yeah, okay.”

We pulled into the parking lot behind a store and got out. I followed her in. It was big store but sort of private. Mostly clothes but no prices or signs of cash registers or anything. A tall woman, even taller in heels, with pulled back dark hair came over and kissed Mrs. Wentworth on both cheeks. “Good morning, Mrs. Wentworth, we’re so happy to see you again. Lisa has the items you ordered.” The woman almost completely ignored me. Her assistant Lisa came over with three stacked boxes tied together. Lisa was younger than the owner ( at least I think she was the owner, she never talked to me so I wasn’t sure). She was much shorter and wearing a short dress. She smiled and even winked at me. Mrs. Wentworth thanked her and said “I need a few things for Stephen here. We’re having company and I think some shorts or something to hold everything would be a good idea.” The owner said, “well, Lisa can help get one of the things we have in stock but we’re shorthanded today Mrs. Wentworth so you’ll have to help with the sizing.” I had no idea what was going on or anything so I didn’t even talk. I wasn’t sure why I needed shorts but Mrs. Wentworth was doing this without having talked to me first.

Mrs. Wentworth looked uncomfortable and like she was going to protest but she didn’t. Lisa smiled at me again and the owner took my shoulders and pushed me in front of a chair like the stools you try on shoes with. I went to sit but Lisa pushed Mrs. Wentworth into it instead of me and whispered “go ahead.” The owner measured my waist and said “30” to Lisa and then waited while she looked at Mrs. Wentworth.

Mrs. Wentworth looked at me and said “Now, Stephen, dear, this is fine. It’s just a measurement. It is all very clinical.” The way she looked, it was like she was trying to reassure herself more than talking to me. Then she undid my belt and pulled my shorts to me ankles and looked at the owner nervously. I couldn’t speak and had no idea what was happening. The owner looked at Mrs. Wentworth with just a hint of a smile and said “not good enough. They are fitted and we need a better sizing or they won’t hold right. Take it out.”

Mrs. Wentworth then pulled my underwear down and held my cock in her hand like she had before. I started to get hard right away remembering things. The owner whispered to me while looking at Mrs. Wentworth “let’s see if you get larger, Stephen, while your teacher helps out. I need to find out if it’s bigger than average or average or small when you’re as big as you get. Now don’t get him too excited Mrs. W. I don’t want a mess just a size.” It was humiliating and also very exciting. Mrs. Wentworth was stroking me and had her spare hand massaging my balls underneath which had me pretty close to exploding. She was very serious while she was doing it and staring very hard at my cock as it throbbed so close to her face except that she would look up at me every minute or so which made me very close to cumming right there. Then the owner handed a ruler to Mrs. Wentworth who had to let go of my balls and press the ruler against me for a few seconds and say “seven.” The owner laughed, which made me gebze escort feel bad, and called out “seven, Lisa.” Then she smirked and said to Mrs. Wentworth “you’re a natural at that.” Then she said to me “according to research the average male penis is 5.5 – 6 inches erect so congratulations.” She was a little condescending so I was embarrassed but happy to learn I was bigger than average.

Lisa came back with tight shorts that were almost like biking pants. Then she explained to Mrs. Wentworth not to me that “when he wears them he needs to hang it on the right side. See, it’s looser there but just a little. It will hold him but not cut anything off.” They handed them to me and I put them on. Tight everywhere but there was a little looseness for my now semi-hard cock to be tucked into. I didn’t know what to say so I just got dressed. Lisa handed Mrs. Wentworth two more boxes “for the waiter.” I took the two boxes and her three and we went to the car without paying anyone.

In the car, I tried to talk not knowing what to say but Mrs. Wentworth interrupted. “Stevie, sweetie-pie, you know how we talked about making sure little Stevie doesn’t surprise people? This is going to help us. I go see Mrs. Jones for a lot of things. She has quite a nice collection so I knew she could fix this. I bet you feel much better with little Stevie in a proper spot, don’t you?” With that, she reached over and patted my leg right there. The whole thing seemed weird so I just said “Yes, Mrs. Wentworth. Thank you for thinking of it.”

She pulled in the driveway and said, “Back at our house. Now we need to get ready for our little lunch party.” We went inside and she started right away showing me what to do. How to answer the door and act very official. How to show a lady into the dining room. How to serve plates and a pot of tea. We worked hard for a couple hours then she talked to me more about having the right attitude.

While we talked, she had me follow her and we went into a laundry room where a bunch of clothes had been drying on air drying racks since before breakfast I think. The first thing I saw was my underwear that she had picked up earlier sitting there, now washed and dry. Almost everything else was her clothes. Actually mostly underwear. She picked up a few blouses and folded them while we talked. Then she told me to “be a dear and help me get these things folded. We don’t want all our undies out when we have our guests at our house do we? I’m sure your mommy makes you clean up too when friends are coming over.”

I started folding things but I wasn’t sure where to start. The things hanging closest to me seemed to be only her panties and the other places had more underwear. I started folding her panties because I knew how to fold them anyway unlike some other kinds of underwear. It was interesting because they were all different colors but they were all silk or lace or things like that. I folded slow because I kept holding them too long. I tried to pay attention to what she was saying but when I was folding a pair of black lace-all-over panties I was distracted. It was the first time I was glad I had the new underwear because it made sure I wasn’t just pointing up and out but was held together.

Mrs. Wentworth didn’t seem to mind. She seemed really happy actually. I didn’t ask if she only had sexy underwear but I did wonder. I mean my mom had some things but most of what I saw in the laundry anyway was cotton and regular. Maybe Mrs. Wentworth was just a lot sexier. I was pretty sure I remembered seeing other things in her room when I was snooping but maybe she washed them separately or something.

She put the laundry in a basket and told me to leave it on her bed. She then took out one of my boxes and put it on top and told me to wear my uniform and get ready quickly, guests would be here any minute. I went up and changed. I was a little nervous at first about what might be in the box but it was just a nice white shirt, tight even though I’m pretty skinny. And also a pair of black pants. You know, like a waiter. The pants were dressy but a little tight in the legs and much tighter on my ass than I wear anything. But that’s the way uniforms are.

I heard a car in the driveway as I came down the stairs. Mrs. Wentworth looked out of the kitchen and I saw she had changed again. Gone was the cool sensual lawyer. Now she was wearing a flowery dress that came down halfway to her ankle and was buttoned up on top pretty high with maybe a little neck exposed. She looked less like a lawyer and more like a schoolteacher. It was very different, I thought, from the red satin tight dress that I dreamed of the first night I stayed over.

She went back in the kitchen and let me get the door as soon as the doorbell rang. I opened the door on three women. They all looked different but also all looked sort of like Mrs. Wentworth the way she was dressed now. They were surprised to see me, I think. I said “good içerenköy escort afternoon, ladies. Mrs. Wentworth is expecting you. Would you care to follow me and I’ll lead you to the dining room.” I was so good I could have played a butler in a movie or something. I turned and walked and they followed, whispering to themselves.

I held the chair for the first one and let her sit before following and doing the same for each in turn. Then I carefully unfolded each napkin and placed it on their laps. I knew my actions perfectly just like I was shown. The ladies were almost speechless when Mrs. Wentworth breezed into the room. She walked around and kissed each on the cheek but they were all obviously old friends.

She nodded at me and said “please bring in lunch now, Stephen.” That was my cue to serve the food. They giggled when I left and I heard one say, “Doris, did you buy him or are you just renting him for the day?” Then Mrs. Wentworth’s voice, “Janine, please, he’s a former student and the son of a friend.” Then another voice saying, “I’d like to teach him a few things” followed by a nervous giggle and the person named Janine saying “can I have my lunch off his cute butt?” And Mrs. Wentworth more authoritatively, “stop it, he’ll hear you and get the wrong idea. Stop it now.”

I came back into the room with two platters with small sandwiches and cold salads to help themselves to. As I leaned and placed them in the center of the table, I felt a finger poke my ass like it was testing its firmness. The lady next to me was smiling. It turned out she was Janine. With her other hand she was gently touching the skin under her neck and above her cleavage. She wasn’t low cut but lower than Mrs. Wentworth and had a teasing smile. I didn’t say anything but I went quickly back to where I left a teapot and started pouring for everyone like I had been taught. Mrs. Wentworth was beaming with approval, Janine was looking hungry and directly at me. Another woman, a brunette, just looked nervous but happy. She was the one that giggled and was a little shorter and about fifty, dressed more businesslike but it didn’t come off quite as sexy as Mrs. Wentworth had done it earlier.

The fourth twirled a string of pearls in her fingers as I poured. She had dark hair, a silk blouse and just stared at me without speaking. Janine on the other hand was talkative. When I poured for her last, she kept finding reasons to touch my arm or bump me. “Stephen, is it?” I nodded. “Stephen, I’m not your grandmother. I’m going to need more than a cup of tea. I notice the wine glass you set out for us. Are you pouring wine soon? Janine’s day out needs more than tea.” Her grin was like a predator surveying birds to eat. The other ladies all smiled or giggled. I guess Janine was known for being the bold one of their group. Mrs. Wentworth interrupted and said “You may serve the wine that’s chilling in the fridge. The bottle on the left please.” So I went to get it too.

In the few seconds I was gone, I could hear the giggler tell Janine “you’re saucy today, Janine!” and Janine respond “and we just got started.”

Everyone had wine except the giggler who said something about driving. I had started with Janine but by the time I got around she was almost empty and holding out for more. Mrs. Wentworth suggested I place the second bottle from the fridge on the side table and then join them. I sat with Janine on one side and the giggling woman on the other. They talked a little. I guess they all went to school together in the past but soon the quieter third woman named Anita asked about me. “Stephen, Doris tells us you’re a student of hers.” Mrs. Wentworth corrected “former student from my last year in the last school I taught at. Now he’s just staying here while his mommy is away.” I just looked at her and thought it was a weird way to say that. The giggler, Kim, asked in a half whisper if I had a girlfriend and giggled. I was trying to sound more sophisticated so I just said “not a specific one right now, you know how it is.” At the same time, I felt someone’s foot rubbing my leg and Mrs. Wentworth said “oh but he had a date with a pretty girl last night, didn’t you dear?” I didn’t know where she was going with this and wasn’t sure how to respond. I mean the pretty girl was her and obviously she knew that.

While I was deciding what to say, she quickled added, “Her name was Lana I think you said, wasn’t it?” I nodded, feeling better about it. “Yes, Lana it was and she was very nice. I had a great time.” With that, I smiled at Mrs. Wentworth who blushed even though no one else noticed or would have understood. Then I felt Janine’s hand on my thigh when she leaned over and asked suggestively “did you get lucky, Stephen?” I didn’t know how to respond when Mrs. Wentworth interrupted almost angrily “Of course not, Janine, stop that. Stephen isn’t going to kiss and tell. He’s a very sweet boy and knows better than that.” Then, almost like she was changing the subject, she said, “Stephen can we start the other bottle?” The ladies had finished the first bottle of wine and I started pouring another while Janine said “you always were a prude, Doris.” But she laughed and so did the others so it wasn’t mean-spirited.

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