Kelly's Diary 175 - Bachelor Party - Cover

Kelly's Diary 175 - Bachelor Party

Copyright© 2025 by Kelly85

Chapter 2: Enjoying Myself While Making Preparations

Erotica Sex Story: Chapter 2: Enjoying Myself While Making Preparations - I did some bachelor parties back when I was in college but that was years ago. I've changed a lot since then and I'm definitely not the same girl now as I was back then, so how would this one go compared to those others?

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   True Story   Cheating   Group Sex   Orgy   Exhibitionism   Masturbation   Oral Sex  

When arranging for a party like this, most people want me to dress up as one of the usual stereotypes - catholic schoolgirl, French maid, sexy business woman, Daisy Duke, and such so I have costumes already for all of those situations. In fact, the schoolgirl costume had been given to me by my own dad for a past Christmas. It’s a cute little ensemble featuring the shortest light-blue plaid skirt that zips down the side for easy removal. Actually, it is a little longer than you might expect which just made it all the more erotic as I could move around, bend over and such causing it to pull up but without quite making it high enough to reveal anything underneath - or if there was anything but me under it. Of course, there WAS something under it.

Going bare bottom has its time and place but for the most part, every stripper worth her salt knows men are turned on more by what they do NOT see than anything else. Otherwise, why bother with all the costumes and long, drawn out strip teases? Sure, they may SAY they want to see you nude but deep down, it’s the gradual removal that turns them on, as if they were getting to see something they weren’t supposed to.

I LOVED my Daisy Duke outfit mostly for the shorts. Actually, there wasn’t much down the legs to qualify them as shorts to be honest. I had cut the denim up so high that half my ass was showing and all there was left in the crotch was a small strip of denim barely wide enough to be strong enough to hold the two sides together. The center strip usually pulled up into my pussy anyway so it was like having nothing on down there. Even so, for stripping purposes I managed to hide a string thong underneath, just to provide a little extra tease when I pulled the shorts down. Just when they thought I was about to be bare- ass, yet another obstruction was in the way! It’s all part of the game - and both sides love it.

Well, I could go on a lot more about my outfits but the only one that mattered now was the one I was supposed to wear at this party. When I discussed it with Brian, at first he said he didn’t have any particular preference but then he called back the next day with an unusual proposal.

“You know, I was thinking more about your costume some more. My brother always had this thing for one of our teacher’s at school - Miss Donnelly. It was weird and I use to tease him about her all the time, but she was the mousiest teacher at school. You know the type - long dresses, hair tied up, glasses. There was something about her, though, that just set Keith off. All he talked about was wondering what was under that dress and what it would be like to “convert” her. I don’t mean she was a lezbo or anything, he meant convert her to a slut. You think you could pull something like that off?”

“You mean, come in like I’m Miss Donnelly and then turn into a slut in front of your brother?”

Yeah, that’s it. Damn, he would love it, I’m sure!”

Well, that wasn’t too hard a request. When he first called I was afraid he’d come up with something bizarre involving chains or whips. Heck, this sounded like fun! The next time I was at the mall I would go to JC Penney, the place to shop when you want something dull and drab. Well, to be fair, the store DOES carry some nice clothes but face it, most girls wouldn’t get caught dead shopping there if it wasn’t for the sales and coupons. Put it this way, I bought a number of outfits there back when I was going to school and then later when I was teaching at a Christian elementary school.

It was a couple of days later before I had an opportunity to shop at the mall. Just as I had planned, I went to JC Penney first and headed straight to the Misses section. I felt a little out of place as usually this was where the moms and older woman shopped. One of the more elderly sales ladies give me an odd look but she probably figured I was buying something as a gift for someone like my mom. Looking through the dress racks, I winced at some of the styles and sizes, pledging to myself that I would never let myself go to where I had no choice but to wear such large sizes. God, some were more like tents than dresses!

Eventually I found a rack with some half-way decent dresses in my size and picked out a few to try on. Fortunately the store wasn’t very busy in the middle of the week and nobody was in any of the dressing rooms so far as I could tell. I chose one towards the end of the row and closed the door behind me. It was one of those deals where the door didn’t go all the way to the floor but instead left an opening at the bottom of about a foot or so. I guess it was meant to be like a restroom where people could see if someone was in there without having to knock or inadvertently walk in. The door DID have this pathetic little latch but it was so flimsy I doubted that it would have held if someone pushed really hard by mistake.

Hanging up the clothes on a hanger on the side wall, I quickly stripped. It didn’t take long as all I was wearing as a pair of old jeans and a Steelers sweatshirt, nothing to write home about for sure. It left me standing there naked as I hadn’t bothered with any panties or a bra. Heck, with the bulky sweatshirt nobody could tell if I was wearing one or not anyway. I hung them on a little hook on the back of the door and turned to debate which dress to try on first.

I started with a cute little number that was a light floral design and a lace top around the neck. Dropping it over my head, it fell down over me and I turned to the mirror without bothering to try and zip up the back or anything. Looking critically at myself in the mirror, it didn’t appear to be all that bad on me and I might have been tempted to buy it for school back when I was teaching. Therein was the problem - it looked cute and “cute” wasn’t the style I was looking for.

The next dress was a turquoise nightmare that I had picked out more for a joke than anything. I couldn’t help but wince when I looked in the mirror. God, it was like something from a 1950’s horror movie. Had I been colorblind, it actually fit me well and I might have gone with it but that awful color! God, it was just too much.

The dress I saved for last was dark brown, almost black, with a tie-around belt that came together in the back. It was a little more low cut than I was looking for, not enough to show any cleavage but not up to the neck by any means. It hung just below my knees with short sleeves that had some lace around the edges. Overall, it was just tight enough to show off my figure without being clingy. Hmmm, this might be the one.

Standing there in front of the mirror, I imagined how the guys would react when I walked into the room wearing this dress, maybe with some modest heels and thigh-high black hose. I certainly wouldn’t look like any stripper any of them had probably ever seen before. Would I remind them of a teacher or maybe a mom of one of their friends back when they were younger, maybe one that had them jerking off at night when they were alone in their beds? I cupped my boobs, squeezing them gently as my nipples reacted to the thought of the whistles and comments the guys would be making. Of course they would want to see underneath right away but I wouldn’t let them, not at first at least, not until they wanted me even more.

My eyes closed and my head dropped back as I gripped my firm boobs through the dress, rubbing the material against my bare flesh underneath, causing it to tease my erect nipples even more. I let out a long breath as my pussy tingled just as little as I dreamed of walking around the room, fending off their groping hands as they tried to lift my dress and touch me. God it turned me on so much to think of all those men wanting me, lusting for me. They wouldn’t have ever seen me before, not know a thing about who I was or anything. All they would be looking at would be my body, lusting for it and wanting it for themselves. To them I wasn’t a girl, with feelings and needs. All I was to them was a piece of meat, something they wanted to fuck as their ancient animal instincts began to rise within them.

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