Tutoring Tess

Tutoring Tess

Update: 2025-10-11
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Neighbor's daughter seeks out widower next door, to help her with human sexuality lessons.

By SilverFoxMullet - Listen to the ► Podcast at Steamy Stories.


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 I was folding the last of my laundry, there wasn't much with just myself left in the house. My son had got married and moved to British Columbia. My wife passed on 2 years ago. Just me now, enjoying a much-too-quiet life.

Then the doorbell rang. I went to the door and opened it, only to find my neighbour's daughter Tess standing on his front porch. I'd watched her grow up next door.

 When my son had moved out ten years ago, my wife and I had occasionally babysat little Tess. It had been nice having kids around the house again. She'd grown up into an intelligent, pretty young girl. She'd also been devastated why Marie had died.

"Oh, Hi, Tess. What can i do for you?"

"Hi Mr Brock. I um, I need some help with some, uh, homework. I was hoping you'd be able to help me?"

"Okays, I don't know how much help I can really be, but I can try. High school was an awful long time ago for me! Come on in."

Tess followed me into the living room and I asked her "Do you want a drink, I've got water, pop, juice, or milk."

"Water's fine" she said.

I poured two glasses and came back, handing her one as she sat there on my sofa. "So, how can I help? My knowledge of high school math is really out of date you know."

She was fidgeting and blushing, as she sat there clutching her drink and a textbook. Finally she exhaled and said "Human sexuality" as she held up the book.

I blinked at her, nonplussed. What are they teaching kids these days? The only response I could muster was "Um, what?"

She set down her book, took a drink, then set her glass on the coffee table. "Mr. Brock…"

"Call me Kenneth, please."

"Kenneth. I, I want to learn about um, you know, sex. I, my friends, they're all starting to do stuff, to fool around, and I um, I want to learn too but I'm afraid."

I sat there looking at her, unable to process what she was saying. She grew more agitated, and blushed even more. Tears welled up and slipped down her cheeks. If I have one weakness, it's a crying woman. I got up and moved to sit beside her and wrapped my arms around her.

Tess sobbed and clutched at me, crying into my shoulder. After a few minutes she pulled back, and I let her go. "Will to teach me?" she asked. Oh fuck no, I thought.

"That depends on what you want to learn."

"I want to learn about sex. I want to learn everything, I want you to teach me."

"Oh. How old are you now, Tess?"

"I'm sixteen. I'm old enough to learn about this."

Oh crap. This is bad. Really, really bad. "You may think you're old enough, but not for me, that's for sure. You're not even an adult in the eyes of the law. I'm sorry Tess, I can't help you with this."

Tears started dripping again as she spoke. "I'm sorry, I shouldn't have bothered you with this. It's just, like, all my friends, they're doing stuff, and I feel left out, I want to, but I'm scared. They all say sex is painful, or uncomfortable, or just, not great. Stuff I've read, and stuff I've watched on the internet, makes it sound like sex should be really good, really fun, but my friends say it's not. I want to learn the right way, so it's good for me."

Wow. What the hell are her friends doing? Ah, right, teenage boys. Worse than useless. Maybe I can't do anything with her, but I can help.

"Ok, I am not going to teach you, at least not any hands-on lessons, but I will offer you some advice."

She straightened up a bit, and wiped her eyes. God she was so beautiful. Very girl-next-door wholesome. The last thing she deserved was some idiot teenage boy humping at her for 30 seconds and then running off to brag about his prowess to his idiot friends.

"My first piece of advice is to masturbate."

She looked confused now. "You want me to what?"

"Masturbate, play with yourself. Look, how will you ever be able to tell your lover what you want and how you want it unless you know yourself? Get comfortable with yourself, learn how to please yourself, learn what makes your orgasms great."

She was staring wide eyed at me now, as my words started to sink in. "How do I do that?" she asked.

"Look up female masturbation videos. Watch and learn, and practice."

"Okay" she said, "What else?"

"Buy a toy. Get a marital aid, a dildo, so you can practice feeling what intercourse is like. You can use other things, but it's better and safer to use the right tools for the job. Look up a sex shop or stag shop. I'll even go shopping for you if you want."

"Oh, yes, would you, please?"

"Certainly. Now, once you are comfortable with your own sexuality, and you find someone you want to be with, make sure you tell them what you like. Don't be afraid to be demanding about what they're doing. They either do it right or you kick them out of bed."

She giggled at this, which I thought was incredibly cute. "Don't discount female lovers either. They like sex exactly the way you do. Once you get good at masturbation you'll be able to please another girl quite well."

"I don't think I want to do that, I like boys." she said.

"You mean 'men' not 'boys'. That's exactly why your friends are having lousy sex. They're playing with boys."

She nodded, so I continued. "Guys like oral sex too. In fact, if you're good at blowjobs you won't have to put up with their inept antics in bed. That's another use for the dildo, to practice oral sex. And if a guy starts to hump your face, if he starts grabbing you and pushing, bite him. You don't have to take that if you don't want it. If it's something you enjoy, then let him play, but otherwise he is there to please you, not the other way around."

Tess was smiling now, tears all but forgotten. She hugged me, and said "Thank you. I will follow your advice Mr, uh, Kenneth."

I picked up her book, flipped through it quickly, and found the section on female anatomy. I showed her the diagram and said "Learn what all your parts are, what they're for, and how they work. This is a good place to start. I'll find you a toy tomorrow and you can stop by to pick it up on Tuesday, OK?"

She nodded, saying "Thank you", and repeated herself after hugging me again.

Once she'd left I locked the door and went upstairs with laundry basket. I dropped the basket on the bed and went into my bathroom. I had such a wicked hard-on, I just had to get some relief. The very idea that the literal girl next door wanted me to teach her about sex had me hard as steel.

She might be jailbait but I could still follow my own advice, and masturbate. Of course I didn't last long at all, but I wasn't trying to last.

I went shopping for Tess on Monday, picking out a nice realistic looking dildo and a bottle of personal lubricant. Maybe it was wishful thinking, but I chose one that was almost exactly my size. The girl at the cash looked kind of funny at me, so I smiled and said "Gift for a friend

Tess knocked on my door the next afternoon when she got home from school. We exchanged greetings and I handed her the plain brown paper bag. She wanted to pay me for it but I told her it was a gift. l got a hug in return and she practically scampered next door. I silently wished her luck. ." It's great to see Tess feeling more confident about her sexuality. I'm still amazed that I'm the one she turned to for help.

The thought of this girl using her new toy to explore herself gave me fodder for my own playtime for the next week. She may only be sixteen, but she's unbelievably sexy.

Afterwards I only saw her in passing, as usual, and we'd wave and say 'Hi'. She looked happy and cheerful, and I assumed her self-directed lessons were going well, as she hadn't returned for any more advice. Part of me assumed she'd developed a romantic relationship and was handling things just fine.

Life went on, I kept busy at work, and did yard maintenance, laundry, and all the usual stuff around the house. I wasn't into playing sports, so I went to the gym a few days a week to keep in shape. My woodworking hobby morphed from a strictly power tool shop to using a lot more hand tools. It was slower paced but I found it a lot more rewarding. Thoughts of Tess faded away. I had my 'internet videos & pics' to keep me occupied when I needed it. I had no interest in pursuing a new love this late in life, so i wasn't dating or putting myself out the

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