A special thank you to Kenjisaito who was again kind enough to review my work. Your willingness to work with so many of us to make sure Lit readers are not bombarded by grammar mistakes is commendable!
The standard caveats apply. All characters are 18 or older and consenting. As with most of what I have published on Lit this story is gender bent. If that's not your thing, this might not be the story for you. Then again, it might just be the story to change your mind.
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Halloween Tricks Are Quite the Treat
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It was a dark and stormy night... when Nicole met Conroy. It was also Halloween night; it just happened to be dark and stormy, a great night to stay inside and party. Nicole was the only girl at the party who wasn't dressed as the sexy version of something. She had recycled the costume she had worn when she played Little Red Riding Hood for the musical, her senior year of high school.
How she still fit in it, six years later, was a minor miracle in itself. But somehow, she had stayed the same -- five-foot-four-inches tall, 125 pounds, a size 4, with a nice perky set of B-cup breasts all the way through college. Sure, her freshman year, she gained the requisite fifteen pounds, but she had worked it off her sophomore year and had kept her figure since.
Conrad was dressed in much less than she was. He had opted for the pink button-up, tube socks, and whitey tighties of Risky Business fame. He had brought along a soccer participation trophy to use as a microphone. He even performed the dance, from the costume's namesake movie, to the great amusement of the party goers. At ten pm, the two were crowned as the king and queen of Halloween, also known as the winners of the costume contest.
Conrad had been charming and pulled her close, for the requisite slow dance. Nicole, at first, wondered why the king and queen of Halloween would have to slow dance in front of everyone like they were in high school, but by the end, she was actually enjoying it. The party continued long after the dance ended, and they only saw each other a few times after that throughout the night, never quite connecting again.
The next week, Nicole received a text message from an unknown number with a picture of tube socks and a short message.
Hey, I hope this is ok. I got your number from a friend of a friend, and I wanted to know if you'd like to go on a date.
A month later, they were a steady couple. Two months after that, they moved in together.
Conrad was in many ways an average guy. Average height, average build, with a slowly growing beer belly, average looks, and an above-average smile. Nicole felt comfortable with him, he complemented her girl-next-door good looks. But one thing about him really stood out, his charm and outgoing nature. Any room he walked into, he was somehow instantly the center of attention. He didn't pull in the girls like some guys, who oozed charm. Nicole was never worried he would cheat on her; she just let him do his thing, and enjoyed the glow of being by his side.
Everything seemed wonderful until they had been dating for six months. Conrad finally landed his dream job, doing sales for a company that specialized in Web3. He left his first job out of college as a regional sales manager for a business travel provider, and overnight, things changed for them. Conrad absorbed the company culture like he was drinking from a firehose.
Gone were the romantic nights at home when Nicole would come home from the small gallery she worked for, and he would have dinner ready. Often, he would spend half the night out with his coworkers, some of it working, most of it drinking. After the first week at the new job, Nicole asked how long it was going to be like this. Conrad promised that it was just a month max, just until he got his feet under him and got his first few clients. Then things would slow down.
Then the money started rolling in. Nicole enjoyed it at first. A new car for her, new furniture, a few fancy dinners at sought-after restaurants, talk of buying an upscale condo in the art district of town. But the late nights and the lack of company started to wear on her. The only time they had sex anymore was when Conrad would come home late, slightly drunk, wake her up, and quickly get his rocks off while she lay there like a sleepy log.
Conrad had been an average lover before the new job, sometimes even a little timid, sex had never quite clicked for them, the only thing that had set him apart was his attentiveness. He had always cared about what she wanted, had listened and tried to make up for his shortcomings. But as time progressed, he was becoming more demanding, more demeaning. Nicole was starting to dread sex with him. She had always been a sexual person, and often, had been the instigator early in their relationship. It had gotten to the point, though, where she was trying not to start anything -- afraid he would ask for a blowjob, a beer, and then go to sleep without asking what she wanted or needed.
His personality was drowning in the firehose that was his workplace. His natural charm was earning him client business, and this made him successful. Their relationship suffered, the more successful he became. Six months in, he had started to take her for granted. He hadn't brought home flowers in months; he hadn't cared if she came during sex for even longer. She was growing tired of being taken for granted. She was tired of his slightly demeaning words and the comments that she should quit her job to clean the apartment and make meals like his coworkers' partners did.
Then October arrived. Conrad informed her that his office was renting a bar for a party. Employees were encouraged to bring their partners. To Nicole, it suddenly seemed like a beacon of hope. A chance for them to start over, remind them of how they started, the king and queen of Halloween.
Halfway through the month, Conrad came home and announced that there was going to be a costume contest, the winners would receive an all-expenses-paid, two-week stay in Jamaica at an all-inclusive resort. But there was a gotcha. Each couple had to dress in outfits chosen by a random draw from ideas submitted by the staff for couples' costumes. A second drawing would choose six couples who had to swap the guys and girls costumes.
Nicole agreed to the game. With the potential of winning the prize and getting a two-week vacation to reset, it seemed like Halloween really could be their special day again this year. She hoped it might mean a fresh start.
With a week to go, Conrad brought home the card with their required costumes. A football player and Tinkerbell, and he had also drawn a costume swap card. Conrad would be dressed as Tinkerbell and Nicole as the football player. Worst costume combination ever.
Nicole doubled down. If they were going to get a bad combination that would make it difficult to win, then she was going to get the best costumes possible, it was a contest after all.
She spent a week gathering everything. The football gear was easiest. A second-hand sporting goods store had the pads, cleats, helmet, mouthguard (a new one); they even had a jersey from the local state school that looked like it might have actually belonged to a player; last but not least, a jockstrap with a cup. In for a penny, in for a pound.
The Tinkerbell costume was harder. The local stores had nothing that would fit Conrad, everything was made for children. Nicole ended up calling a friend that did cosplay, in desperation, who came through at the last minute with a custom costume so unique that it almost looked like it was made from real giant leaves. Her friend lent her a pair of gossamer wings that were attached to the back with clear medical tape so they looked almost real. Some shapewear; some thick, nude pantyhose; a pair of small breast forms; and a blond wig with a bun finished the outfit.
Halloween night was a bit of a mess. Conrad initially refused to wear the outfit. He said they could stop by some secondhand store and buy a green dress and that would be fine. He was adamant he wouldn't wear the shapewear. After a beer to calm his nerves, and Nicole promising a sexual reward after the party, he finally relented.
Into the shapewear which tucked in his gut, pulled his package tight, and gave him a slightly slimmer waist, the breast forms glued into place to hide his sparse chest hair and give him enough of a bust to keep the strapless top on. A close shave, a little foundation, blush, and then the wig. Conrad looked like a man in drag, not overdone, but definitely not a woman. The dress was fantastic, clinging in all the right places, they debated on putting the wings before, but decided to wait until the last minute so they wouldn't get destroyed in the rideshare on the way. Conrad balked at the last minute about slipping his pantyhose-clad feet into the green sequin heels Nicole presented him with. In the end, she promised that if they won, she would allow him to take a video of her in the Tinkerbell outfit sucking him off.
They rushed to the rideshare and arrived at the bar a fashionable thirty minutes late.
Conrad was immediately the talk of the party. His work buddies slapping him on the ass, stroking his wings, and Nicole noticed more than one grab his breast forms to see how they compared with the real thing. She felt her spirits lift as more and more people talked about his outfit. It only took twenty minutes for Conrad to ditch her in favor of hanging out with the guys. Five shots later, he had seemingly forgotten she was even there, and the bro culture of the company took over and the boys (three of them also dressed as women, none of them as well dressed as Conrad) took up residence in the back corner of the bar with a near constant stream of drinks making its way to them from the bar.
Nicole ended up standing at a high top near the bar, nursing a bright orange Halloween cocktail by herself, when Conrad strutted by, dirty fingerprints marking where someone had tested how supple his temporary bust was, and slammed into a woman dressed as a witch.
