Kelly's Diary 118 - Teasing While Tutoring - Cover

Kelly's Diary 118 - Teasing While Tutoring

Copyright© 2025 by Kelly85

Chapter 5: Fantasizing About Nathan

The final day arrived and as I tried to decide what to wear (or not to), my thoughts began to wander as they often did, but this time I couldn’t help but think of how things would go with Nathan if I allowed them to happen. I was sure his father wouldn’t have said anything, no matter what we did, and Nathan being fourteen and horny wasn’t certainly wouldn’t protest.

After a quick shower I was back in my room standing in front of my mirror. Just like every girl when she looks in the mirror, I couldn’t help but critique my nude body. How had I looked in this same mirror back when I was Nathan’s age? Things had certainly changed since then - most for the better I would say, but there were a few things that could have stayed around. Face it, I’m seven years older than I was back in the summer when I lost my virginity. Sometimes it seems like it was twice that yet again, there were days it was like yesterday. I remember how excited I was the day I got dressed to meet Steve, knowing it was likely to be the last time I looked in the mirror and saw a virgin. My boobs were barely out of my training bra and my legs may have been ridiculously skinny but at the time I felt incredibly sexy and grown up.

Seven years later I was starting to think about working out and my boobs were almost to the point where a bra might be a sensible thing to wear, if not the most desirable. Back then I remember being so proud of the new fuzzy hair that was finally covering my virgin pussy. Now I just frowned at my shaven crotch as I realized I hadn’t shaven in two days and if I didn’t do it soon, I’d be breaking out again in a rash when I eventually did.

What must it be like for a woman my mom’s age or so when she looks in the mirror? At least my boobs were still perky enough I could get away without a bra most of the time (for now at least). My upper arms weren’t sagging and my stomach was pretty flat. Like always, I loved my ass and there still wasn’t any flab or cellulite back there to worry about.

Overall, I guess, I was content with the girl looking back at me in the mirror. My only regret was that I couldn’t carry off the “teenager” look any more, unlike my cousin Kristen who still looked sixteen or seventeen at age twenty. The only reason that concerns me is that I think it turned guys on more when they knew I was a teenager. For some reason, telling a guy I’m twenty one just doesn’t seem to be as naughty as back when I said I was eighteen. Even so, I’m not about to lie about my age - not yet at least.

“Staring in the mirror again?”

I turned to see my mom smiling at me from the bedroom door.

“Yeah, I have to get going soon,” I sighed

“Tutoring Nathan again today?” she asked.

“Yeah, last time too. They’re heading for Europe tomorrow.”

The disappointment in my voice must have been apparent. My mom entered the room and stood behind me. I felt her hands on my bare shoulders as she rubbed them gently. “Well, don’t you think you’ve teased the poor boy enough for one summer?”

“Mom, you know I haven’t done anything bad!” I protested.

Indeed, other than wearing some clothes that were a LITTLE provocative but by no means shameful, I hadn’t done anything untoward with Nathan. Oh sure I didn’t stop him from staring at me and looking at my shorts or between my legs, but I never let him so much as rub against me nor did he ever see anything more than he could’ve seen in a Sears catalog. Especially important, I’d never so much as laid a hand on him, not even in encouragement. When it comes to my professional life I take my responsibilities seriously and the last thing I need is a reputation for being a slutty tutor when I eventually apply for a teaching position (even if I was).

“Well, I’m not trying to say you’ve been BAD. It’s just that I see from the outfit you’ve got laid out that you’re not exactly meeting the school district dress code.”

She was referring to the skirt and blouse I’d spread out on my bed. The skirt was made of denim and was tight around the hips with about a two inch pleated section on the bottom. It technically covered my ass, at least when I was standing up. The light-blue blouse was rather sheer and probably at least one size too small for my measurements. The black thong I’d chosen covered my pussy but that was about it as the back side was not much more than some strings to hold it on me. There wasn’t a bra but I hadn’t worn one to their house one in weeks now.

“Hey, isn’t that the outfit your dad bought you a few weeks ago?”

I nodded as indeed it was. My dad loved to buy clothes for me and as a man, he knew what turned him. He would bring them home and give them to me and then I would pose for him afterwards. He had loved this outfit and so far, the only time I’d worn it was for him.

“No don’t get me wrong, Kelly, I don’t mind you wearing it for your dad, but don’t you think it’s a little over the top for public consumption?”

“Oh Mom, I’m not fourteen anymore,” I huffed. Maybe not, but I could certainly whine like one still! It was the first thing to come to my head, undoubtedly from having thought so much about being fourteen again before she’d come in my room.

“Exactly,” my mom said softly, not reacting to the aggressive tone of my response. “It was easier to get away with things back then, people just thought it was ‘cute’. Now you’re an adult and frankly, you look like a street walking whore in that outfit. That’s fine for your dad to see you in but are you really sure you want to wear something so provocative today?”

I felt myself stiffen at her words. Wow, she usually wasn’t quite so direct with me and calling me a whore was NOT typical at all. Maybe she was right, was I going too far?

“Well, it’s up to you I guess,” she said wistfully as she turned to leave, “You know how I feel about it.”

After she had left, I looked back in the mirror again. Was she right? Of course she was, my mom almost always was. But was it really so bad to look like a slut, even a whore, when your intentions are to tease someone? That’s like saying it’s bad to dress like a ghost if you want to scare someone. In the end what she said actually confirmed my decision. Poor Nathan was going to get an eyeful today. He wouldn’t have a tutor this time, he’d be getting a whore! God, I could only imagine how hard he’d be jerking off when I’d left. Who knows, maybe his dad would be as well. After all, it certainly had given my dad some incentive!

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