Kelly's Diary 182 - Mentoring
Copyright© 2025 by Kelly85
Chapter 3: Our First Date
Erotica Sex Story: Chapter 3: Our First Date - Usually when you think of mentoring, you picture an older person passing on their knowledge to a younger person, leading them along their career path. Sometimes it works the other way too, and not just at work but for play too!
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Mult Consensual True Story Group Sex Exhibitionism Masturbation Oral Sex
We met at the mall food court a few days later, just as planned. In between I hadn’t heard a word from Kate, not a phone call, e-mail or text message. Then again, I wasn’t sure if Kate was all that computer literate. She was at that age where it could have gone either way. Probably it was a case where her husband did all the computer stuff and she didn’t bother with it.
Seeing her sitting at an empty table, her purse sitting on her lap, together with knowing why we were meeting, I almost had laugh but somehow I managed to control myself and just smile nicely instead. Kate was dressed in loose jeans and a turtleneck top with a winter jacket over it all. A pair of plain brown dress loafers and a simple gold necklace around her neck finished it off. Her makeup was basic, some eyeliner, lipstick and a light base but nothing overwhelming. A pair of diamond earrings were in her ears, no doubt a present from her loving, if dysfunctional, husband. Hmmm, they looked to be pretty big ones too. Was someone trying to compensate for something, maybe buy her off?
I would have given anything to be able to read her mind just when she saw me. The look on her face was priceless so no doubt her thoughts had to be something else indeed. While I was far from being in full “slut mode”, I wasn’t exactly dressed for family day at church either. Had it been summer I would’ve gone for shorts but with winter arriving, a short denim skirt was more in order. Granted, when I say short, I mean SHORT - as in just a few inches down from the bottom of my ass and tight around the waist with ruffled bottom half.
Underneath I was wearing a standard black thong which wasn’t visible - yet at least, but when I sat down it would take some careful maneuvering NOT to show it off when I crossed my legs, if I really wanted to hide it in the first place. On top I had a tight pink camisole, no bra, that came down to my bellybutton when I tugged it down but then it would quickly creep up to reveal a few inches of my torso. I liked the way it dropped down low enough to show plenty of cleavage and with the cold air outside my nipples were popping through like someone had put the nipples from a baby bottle underneath!
My high heels were about four inches, enough to let me strut through the mall and make the best of my legs while not so high I was in danger of tripping over myself all the time. I was wearing a thin winter jacket with a fur-lined collar that was unzipped, falling open to let everyone see what little I was wearing underneath. If nothing else, was certainly getting the looks from every teenage boy in the place, not to mention most of the older ones as well.
“Hi Kate, I’m so glad you could make it!” I greeted her as I took a seat opposite.
I crossed my legs just slowly enough to let some of my “observers” catch a quick glimpse of my thong and wondered if they were turned on seeing my underwear or disappointed that I was wearing it in the first place.
“Oh my god, I can’t believe your outfit!” she gasped, trying to appear nonplussed but clearly flustered.
“What’s the matter Kate?” I asked, trying to appear as if I really didn’t know what would be bothering her. “Too conservative?”
She rolled her eyes at my futile attempt at humor. “Like ... you may as well not be wearing anything ... you know? Do you always go out looking like THAT”
After some of her comments at breakfast earlier in the week, Kate seemed to have this knack for insulting me without actually doing so but I didn’t take it personally, it was just her. I leaned over towards her, deliberately so as to let my boobs hang down to give her a good view of them. She started to avert her eyes but it was like a car wreck where you know you shouldn’t look but yet you can’t resist.
“Look, one of the things you need if we’re going to make this work is more self-esteem. Dang it Kate, you’re a hot women yet you dress like my grandmother. How do you expect to get yourself off when you’re don’t appreciate what you’ve got?”
She looked at me with an odd expression, as if she didn’t quite understand what I’d said - or maybe it was more like she didn’t WANT to understand.
“Look, we’re going to do some shopping and have some fun, OK?”
Kate just nodded, as if she was unsure of herself to speak. I took her by the hand and this time she didn’t pull back. It wasn’t anything overt, just two girlfriends holding hands but it was a step, albeit a small one, in the right direction.
As we stepped out into the general mall area, I turned to Kate and smiled saying, “OK, first things first, you need some new clothes! What do you say we start from the inside and work our way out, OK?”
At this point I think Kate was just overwhelmed. It was hard to think of her as being fourteen years older than me. You would have thought SHE would be the one to teach ME, not the other way around. From the way she flinched as we walked by, I think she was a bit surprised when we passed the Victoria Secret store and headed for Macy’s instead.
“You seem surprised,” I observed as we walked quickly down the aisle towards the mall anchor store,
“Well, I just assumed you did all your shopping at places like THAT,” she replied, still a note of surprise in her voice. There it was again, that inadvertent little dig which was starting to get irritating!
“Well, believe it or not, you can get some pretty nice things at regular departments stores and pay half the price,” I told her, “Besides, I know the guy who works the lingerie department at Macy’s ... we’re pretty good friends.” Kate looked at me at that and I laughed at her paranoia. “Noooooo, not THAT kind of friend ... you’ll understand when you meet him.”
Entering the lingerie department, I spotted Frank and pulled Kate over to him. She probably would never have guess that this was the guy I was talking about ... and for good reason. Frank was in his fifties, very thin and dressed, as always, immaculately. One look and you just KNEW he had to be gay - and you’d be right.
“Frank, I want you to meet my good friend Kate, she needs some advice on a few things and I told her who better than you to help her out!”
Frank took Kate’s hand and bowed slightly. He introduced himself and Kate sort of replied, but barely audible. Frank looked at me with a “what the hell is this all about” type of glance but we’d known each other for years and I knew he trusted me enough that if Kate was a “friend” of mine then she was OK. Actually, my mom introduced me to Frank back when I was getting my first bra. He was someone I trusted totally, probably one of the few men I could strip naked in front of and know with 100% certainty that he wasn’t imaging fucking me.
“You know Kate, Frank once told me that 90% of the women he sees are not wearing the right bra size, or at least don’t have their bras adjusted properly. Isn’t that so Frank?”
Frank was giving Kate the once over and didn’t even seem to have heard me. Kate shifted her weight from one foot to the other, clearly uncomfortable with the situation. Frank had one hand to his chin with the other cupping his elbow, clearly lost in thought as he stared at Kate’s chest. It was more like he was analyzing her than ogling her though. Frank was always a total professional in his work and I knew Kate was 100% safe with him. His mannerisms were a little hard to get use to as when most men looked a5t you the way Frank did, it meant something entirely different.
“When was the last time you were fitted?” he asked her softly. Kate just shrugged and Frank shook his head and smiled at her. “Well Kate, I think I can help you. Do you mind if we step back into a dressing room?”
Kate looked at me as if checking to see if this was all on the up and up. I just nodded and smiled, assuring her in my own way that everything was just fine. Her chest rose as she took a deep breath and followed Frank into one of the back rooms. Once inside, he pulled out a tape measure from a drawer. Then he pointed at her top and fluttered his finger at her.
“Let’s get to it ... I can’t do anything with your clothes on you know ... so let’s get them off,” he instructed her, as if it was just the most natural thing for a woman to strip in front of him. Kate hesitated and I was sure she had to be wondering what in the world I’d gotten her into.
“Say Kate, would it help if I took my top off too?” I offered, trying to make her more comfortable.
She quickly shook her head and said no, that it was bad enough to undress for a strange man let alone be topless with another girl at the same time! With that, she unbuttoned her blouse. I helped take it off of her and then I hung it on a hook on the back of the door. That left her in her bra, a conservative Playtex style that my grandmother probably would have preferred but nothing sexy whatsoever about it.
As I was already behind her, I reached out and started to unhook her bra clasps. She started to pull away instinctively but then she stood her ground and allowed me to unsnap it completely. The shoulder straps fell to the side and she held the bra against her boobs to keep it from falling to the floor.
“C’mon, put that old thing to the side and let’s get going Kate,” Frank encouraged her.
Kate sighed audibly and let it fall from her boobs, setting it on the bench seat to the side of her. For the first time I saw her naked, well topless at least. Her boobs weren’t as perky as I’m sure they were years ago but they were still quite solid and held themselves up pretty much on their own - suspiciously well in fact. Frank picked on that as well.
“Nice ... Dr. Wanchowski’s work I assume?”
Kate’s eyes widened as if she had been goosed, “Uhhhhh, how did you...?”
Frank smiled and assured her, saying, “Hey, you see enough women as I do and you start to recognize the workmanship. The man’s a genius and I see you were no exception.
Ahhhhhh, so Kate’s boobs WERE fake! I wouldn’t have guessed it but then I’d never seen her topless before either. Considering how conservative she was always dressed, the odds of anyone else seeing her “assets” bared were pretty remote. I had a sneaking suspicion that the boob job was something her husband had demanded. Most women that get their boobs done can’t wait to show them off to the world. The fact Kate always kept hers well-hidden was a pretty strong statement in and by itself.
“Actually, I’m a bit surprised the good doctor never told you what size you were,” Frank commented, making conversation as he approached Kate with the tape measure, “That’s unusual. You know, for full-figured women like yourself, having the correct bra fitting is more than how you look, it’s essential to your health and comfort.”
He reached around her and measured her band size and then cup size. He seemed to be doing some calculations in his head and then measured her boob again, as if he wasn’t sure the first measurements he had taken were correct. It might have had something to do with her plastic surgery. For girls like me, with “average” boobs and “natural” shape, the standard measurements usually came out pretty close but when a woman deliberately modifies the shape of her breasts from what Mother Nature intended, Frank told me in the past it can be a bitch to get the right size! Usually he would mutter something about “don’t fool with Mother nature” but he was too much of a gentlemen to make such a comment in front of Kate.
Frank abruptly left the dressing room, leaving Kate blushing like a little girl after kissing her first crush. She held her hands over her boobs, as if she was trying to hide herself from me. I reached out and gently pushed her hands down to her side.
“You know Kate, you’ve got a GREAT figure and you shouldn’t be embarrassed to let others see it,” I said, trying to reassure her.
Kate tried to smile but it was obviously forced. “I TOLD you Kelly, I’m not THAT kind of girl,” she whispered to me, as if afraid someone might overhear us.
Just then Frank returned and Kate quickly tried to cover herself again. Frank had brought back several bras of different styles and colors with one thing in common - they were all a heck of a lot more revealing than the old-maid version she’d been wearing when she came in. As much as she tried to hide it, I couldn’t help but notice a slight smile at the edge of her lips as she looked at them.
One by one, Frank tried them on her. My favorite was the red one, It was so deeply cut that it barely concealed her nipples and it lifted her just slightly, enough to emphasize her cleavage without having that fake “WonderBra” look where your boobs are all squeezed into the middle of your chest. I convinced her to leave it on and I think she liked it, even if she tried to act as thought it was too revealing for her.
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