Kelly's Diary 148 - Amateur Night - Cover

Kelly's Diary 148 - Amateur Night

Copyright© 2025 by Kelly85

Chapter 1: Dressing For the Party

Erotica Sex Story: Chapter 1: Dressing For the Party - A night out at a bar or club isn't usually tops on my priority list yet there are those times when it can be fun. Besides, you never know who you're going to run across from your past!

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   True Story   Exhibitionism   Oral Sex  

While I’m not a “party girl” in the sense many of my friends are, I still enjoy spending a night out with my girlfriends now and then that includes a little more “fun” than your standard evening at a club gossiping and trading stories. At the far end of the spectrum are what I call the pure “sex parties” - the ones my best friend Beth is really into. She has somehow convinced me to attend a number of them in the past and while I have to admit I’ve always had a good time, I don’t see how I could handle a steady diet of them. More typical are the nights we go to a sports bar or club where people get a little carried away now and then but some semblance of public order manages to remain.

Tonight was supposed to be one of those nights where we would show up as a group, flirt and maybe fool around a little as the evening progressed. Even so, we all knew when it was over nothing “serious” was going to happen. In the neighborhood where I live there are lots of small bars which don’t appear to be much from the street but often have a small restaurant in the back in addition to the bar up front. Many even have patios where they hold various events designed to bring in people to eat and drink. The one my friends and I were planning to attend was such a place. You had to walk through the smoky bar and then past the eating area to get to the fenced-in patio out back. I’d been there before and they usually had someone playing music with tables and chairs set up with a small stage for karaoke and games.

Getting ready for the evening didn’t require a lot of imagination. The standard “uniform” for most girls at these events was anything that showed a lot of leg and ass, not to mention as much cleavage as you could legally expose. For me, that usually meant either a really short skirt or a pair of “Daisy Duke” cutoffs matched with a tube top, halter or cami. Thongs have become almost a requirement these days, replacing sexy sheer lace panties. Bras are always an option. On the one hand I love the way my boobs look loose and free but then there is the teasing aspect of a bra that can be even more fun under the right circumstances. My philosophy is that if I intend to let the guy fondle my boobs then the bra stayed home but if my goal is primarily to tease and flirt then I pick out one of my sexier versions.

After changing my mind at least a half-dozen times, my bed was covered with different outfits. I finally sat down on the chair by my desk and stared at them all. If guys only knew how much effort a poor girl has to go through to tease them! As I sat there contemplating my dilemma, my mom passed by my room and then turned around and came in. “Looks like someone is having a hard time deciding on what to wear,” she observed astutely, waving her hand at all the clothes I had out.

“Yeahhhhhhh, what do you think Mom?” I asked, “Skirt of shorts?”

She put her hand to her cheek as if lost in deep thought and then walked over to my bed and picked up a cute denim skirt, one of my favorites. “Oh! So this is supposed to be a skirt?” she teased me, holding it out in front of her and shaking her head as if she couldn’t figure it out, “And here I thought it was some sort of wide belt.”

“Mommmmmm,” I whined, “YOU bought that for me, don’t you remember?

My mom sighed heavily as if the weight of the world was on her shoulders from trying to be a good mother. She put it back on the bed and picked up a pair of cutoffs, the ones with more holes in them than anything. She started to say something to me again but then shut her mouth and shook her head some more. “What happened to that sexy little pink dress your dad bought you?”

I knew exactly which one she was referring to. It was a halter style dress with a thin spaghetti strap running around my neck. It was cut really low and showed off my boobs incredibly well. It wasn’t the shortest dress in my closet by any means, but I think my dad was drawn to it because of how good my boobs looked in it. I hadn’t worn it in quite a while and so I found it interesting that she should remember it.

“It’s back in my closet somewhere,” I answered.

“Why don’t we see how it looks on you now?” my mom suggested.

I shrugged and opened up my closet where I rummaged through everything and finally found it hanging towards the back. As I took it off the hangar, I marveled at how light it was. It was like I was barely holding anything in my hand! My mom stood back and watched as I stripped and held the dress up against my naked body.

“As cute as you look standing there naked like that, why not try the thing on?” my mom said as I waited for her assessment.

Not rising to the bait, I just smiled and pulled it over my head and let the silky fabric fall down and settle over me. I cupped my boobs and adjusted them into the top and straightened out the bottom hem.

“Wow, that really looks cute on you!” my mom praised me, “It’s easy to see why your dad loved it so much.”

We each glanced at my all but totally exposed cleavage and then we laughed together. Yeah, it was REAL easy to see what my dad liked it on me. Although it was more formal than I had planned to wear, the thin material felt so loose and soft against my skin I knew immediately it was going to be perfect for me. Fortunately, I had a naughty pink thong that I’d picked up only a couple of weeks before that would go perfect with it. It certainly didn’t hide a whole lot but it would keep me legal when my dress flew up or I sat down too quickly. Note I said “when” and not “if”!

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