Tricked with a Treat

Story Info
A Halloween Masquerade party is the opportunity she needs!
19.2k words
4.84
251.5k
616
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Goldeniangel
Goldeniangel
12,558 Followers

Author's Note: I struggled on what category to put this in. It would also apply to First Time or Erotic Couplings, but I ended up deciding that Romance described it best of all because the romance the meat of the story, whereas the other categories only describe the intercourse. I hope you enjoy!

**********

Lily pulled another costume off of the rack and held it up to herself. "What do you think about this one?"

"Geezus!" exclaimed Veronica, her best friend. "I thought you were going for sexy, not out and out skank!"

Looking over the frilly french maid outfit that was more white lace than black silk and wouldn't cover more than the bare necessities (if that) Lily shrugged. "At this point I'm looking for whatever will get me noticed by Paul. This would be perfect for being Yvette from the movie Clue."

Veronica rolled her eyes. "Well that will get you noticed by more than one guy, but probably not in the way that you want."

Holding up the costume in front of her and looking in the mirror, Lily had to admit that her friend had a point. There was a fine line between "come and get me" to a specific person and "I'll sleep with anyone" when it came to women's Halloween costumes. Slutty wasn't her usual.

Halloween was Lily's favorite holiday. Ever since she was a little girl she'd loved playing dress up and that had never changed as she'd gotten older. She took every chance she could to dress up, whether it was for a party, spirit week in high school, the midnight showing of a movie, or really any excuse at all. Of course, her costumes had changed over the years from when she was a little girl. Now at the age of 19 she wasn't a little girl anymore and she needed her costume to reflect that. She also needed it to hide her. Lily was absolutely determined that this Halloween she was going to get something she'd been wanting for years: her older brother's best friend Paul. She knew that she wouldn't be able to get a date with him or anything like that, but she'd been half in love with him ever since she was a teenage. Four years older than her, he'd always seen her as a little kid, but now she was all grown up and she still wanted him. Always pragmatic, Lily didn't expect him to suddenly see her for herself and realize that he wanted her just as much as she wanted him.

However, during Halloween she could be someone else. Anyone else. Someone that Paul would notice, someone he'd find sexy... and then she'd seduce him into her bed and finally achieve a fantasy that she'd had ever since she knew what sex was: losing her virginity to Paul Donner.

"Here, this is more appropriate," Veronica said with a giggle, brandishing a sexy nun outfit.

"Oh please," Lily groaned. "The whole point is to lose my virginity, not flaunt it."

"You'd be flaunting plenty of things if you wore this," her friend replied with a giggle. She held it up in front of her own body. "Fine, maybe I'll try it on."

"I'm sure Chase would love that," Lily teased. Veronica laughed. The pretty redhead had been going out with her boyfriend Chase for the past year and Lily knew very well how hot and heavy the two of them got. In fact, talking to Veronica had been part of what settled Lily on making her fantasy come true. She'd watched as Veronica had crushed on Chase for forever, before they finally got together and eventually Veronica had lost her virginity to him. Apparently it had been an amaaaaaazing night and part of it had been the fulfillment of something Veronica had wanted for a long, long time.

Well Lily had wanted Paul for a long, long time. She'd waited, hoping that someone else might come along, someone she could fall in love with and forget all her feelings for Paul, but she had nothing but lackluster interest in the guys that she met. Yet every time Paul had come home from college and visited with her brother Robert she'd fall head over heels for him all over again. Not just because he was gorgeous - although she'd practically creamed her bathing suit bottoms when he'd shown up at the local community pool with Robert. Her and every woman with working hormones. Mostly because Paul was a good guy. He took time to talk to her parents and help her mom out with things around the house that her Dad and Paul hadn't gotten to yet, and he always had something good to say about everyone. On top of all that, he was also funny, charming, read the same books and watched the same movies as her, and was a drop dead gorgeous hunk. It was enough to make her scream in frustration that he was willing to spend time with her but acted like she was still 12 years old.

When she'd found out that he and Rob were going to Lisa's Masquerade Halloween Party she'd realized that this was her chance to have her special night; all she had to do was become someone else. To see if she could attract Paul to her and seduce him if he didn't know who she was. And for that, she had to have the perfect costume. Something that would cover the parts of her that she didn't want him to see and flaunt the assets he'd never noticed before.

"Hey, how about this?" Veronica said, holding up a white and pink plastic sixties go-go girl dress.

Lily made a face.

"No, seriously, it'll look fantastic on you. Plus then you could get a go-go girl wig to cover your hair and no one would think any of the fact that you're wearing a wig. And it'll be sexy without being skanky."

"You have a point about the wig," Lily admitted, taking the dress and looking at it. Suddenly a vision flashed in her mind of herself in the dress with white go-go boots, a pink wig, white mask and glowing pink eyes. She'd really been wanting to try those crazy colored contacts and here was the perfect outfit for it! The costume would make her almost completely anonymous. "I'll try it on."

Squeezing into the tight plastic wasn't easy but it was more than worth it.

"Holy crap," Veronica said, her voice breathy as Lily came out of the dressing room.

Turning to the mirror, Lily could see why. On the hanger the dress had looked fairly covering, which is probably why the more conservative Veronica had picked it up in the first place. On Lily it was scandalous. The fabric club to her curves, outlining them, hugging them seductively. The short, short skirt barely covered the swell of her ass and she would have to make sure not to bend over too far unless she wanted to give everyone standing behind her a show. The short length of the skirt also made her legs look miles long. With her dark blonde hair and light brown eyes she looked pretty in pink, once she put the rest of the outfit together she'd look like a 60's bombshell.

"Yes..." she breathed, staring at the vision she saw inside her head. "This is perfect."

The fact that it covered more than most of the other sexy costumes only invited a man to look further, to want to see what was underneath it. It hinted at everything and showed nothing. Most guys would probably move on to easier prospects but Paul was the kind of guy who would appreciate both the challenge and the relative demureness (in comparison to some of the other costumes that she knew girls would be wearing). It didn't scream one night stand but that was a good thing. Both her brother and Paul were more into relationships than into casual sex, although she knew from listening to them that it had happened occasionally. She also knew that they both used protection religiously.

Good. Yes. This was everything she wanted to be for Halloween. Sexy but innocent in pink and white; a seductive challenge. It was also something that she, Lily, would never have chosen for herself. Lily always wore costumes that allowed her to wear flats instead of heels - although this year it wouldn't matter since Paul was more than a couple inches taller than her 5'7" - and she never wore anything generic. She was Jessica Rabbit or Loony Luna, Sleeping Beauty or Sarah Conner. Lily's costumes were always specific and complete; she'd never just gone a 'a witch' or 'a princess'. Paul would have no idea it was her, much better than her Yvette idea - even if she did know that Clue was his favorite movie and that he'd lusted over Yvette in high school. Maybe she'd do that next year, see if he noticed her for herself.

At any rate, she was going to throw herself into anonymity this year. She'd get her one night and then maybe she'd be able to move on from him. Maybe by this time next year she'd have a real relationship, once she'd gotten Paul out of her system.

"Veronica you're a genius," she announced.

"If I was a genius I'd figure out a way to talk you out of this," her friend retorted. "Why can't you just seduce him as yourself?"

"I tried that over the summer, remember? Apparently putting suntan lotion on a girl is a lot sexier in books and movies than in person judging by how unimpressed he was at putting his hands all over my back. Although I didn't burn once this summer," she said a little glumly. In fact she'd practically done cartwheels trying to get Paul to notice her. Sexy clothes, massages, suntan lotion, sexual innuendos - her brother had put a quick stop to those, none of it seemed to do anything to make Paul sit up and pay attention. In fact by the end of the summer he'd barely been coming around anymore. Rob had told her that he was tired of having his little sister hanging around all the time and that he was going out with Paul instead. And looking forward to the day when he moved out of their parents.

Lily made a face at the memory. Even though she and Rob got along pretty well she knew that she'd been cramping his style, but she HATED that he'd circumvented her seeing Paul more often at the end of summer. Hence her desperation now in October.

"I know, it's crazy... but I want this. And if he never knows, then even better and I can keep trying to make him see me as me, but right now I just want this. I have years of backed up frustration about this guy."

"What if he sucks in bed?"

"He won't," she said confidently. He couldn't possibly.

"What if he does?"

"Then that will probably be a good thing since it'll help me get over him."

That shut Veronica up. But only for a moment.

"Don't you want your first time to be special?"

"Of course I do, that's why I want it with Paul."

"Are you in love with him?"

"Yea- I mean... dammit Veronica!" Lily stomped back into the dressing room to the sound of her friend's laughter. The entire time she'd been planning this she'd been doing her best to hide her feelings over this because if things blew up in her face she didn't want anyone to know what a big deal it was to her. Not even Veronica. It would just be too embarrassing. But Veronica had tripped her up with all the questions, she'd just been answering automatically without thinking. Damn.

When she came back out of the dressing room, back in her normal clothes, Veronica was looking more serious again.

"Aren't you worried about getting your heart broken?"

Lily sighed. Now that she'd admitted part of it she might as well admit it all. "You don't think it's already breaking? Seeing him dating other girls, having other girlfriends and never even looking at me like I'm a possibility? And he won't. This way at least I'll have some small part of him, know that some part of him finds some part of me attractive and worthy."

"Aww honey," Veronica got up from her seat and slung her arm around Lily's shoulders, looking both sympathetic and worried. "He's an idiot for not being able to see you."

"No, the problem is that he sees too much of me. Too much of what he saw growing up. I have no womanly mystery for him." Lily looked down at the garment in her arms. "But now I can create some and if that means that I lose my virginity to the guy of my dreams then even better. If it's awful then maybe that will help me get over him and he'll never even need to know about my feelings. If it's amazing then maybe that will satisfy me and I can move on."

"And if it's amazing and it doesn't completely satisfy you?"

"Well, something is better than nothing. And I'll still have lost my virginity to the guy that I've been wanting to give it to for years and it will be a special memory for me."

"I can see so many ways this could backfire," muttered Veronica.

To tell the truth, so could Lily but she'd thought through all of the consequences and had decided that the risk was worth it. She knew that Paul might never look at her, Lily, the way he looked at other girls. But she wanted to try. Dammit, she just wanted a chance. Even if the only way she could do it was hidden behind a mask.

**********

Paul adjusted his Zorro mask as he and Rob headed up the front walkway to the party. "Is it on straight?"

"Yeah, you look good," Rob said with a grin. "How about me?" He adjusted the feather on his hat.

"Like you're ready to rob the rich blind," Paul replied, with a slight emphasis on "rob" that made his friend snort. He must be in a good mood, normally he hated Paul's puns and it was up to others to laugh at them.

Giving his friend a once over, he had to admit they looked pretty good. Rob was wearing dark leather boots, green pants and a dark green shirt with a brown leather vest over it which was belted closed. There was even a plastic sword hanging from a scabbard. Paul was similarly outfitted, but in all black, looking exactly like the legend of old.

"Kind of funny that we're both dressed up as similar characters," he said.

"Yeah well that's Lily for you," Rob replied as they reached the door. "Don't know what I'd do every Halloween without her. That mustache she found for you is ridiculous by the way." The two of them always managed to win some kind of costume contest, thanks to Lily's help with putting together very detailed costumes. She was always on top of that kind of thing and never minded lending them a hand with theirs.

"What is she doing this year?"

"Some party with her friends I think."

"No, I mean, what's her costume? She didn't mention it to me." Paul always loved seeing what she came up with. Even as a middle schooler she'd had amazing costumes and they'd just gotten more detailed as she'd gotten older. Last year she'd made an incredible Loony Luna and had even made her own radish earrings. He always admired her ingenuity and was a little disappointed that she wasn't coming to the same party as them. Not that she always did, but he hadn't even gotten a glimpse of her tonight since Rob had picked him up in a taxi on the way to the party.

"I'm not sure," Rob said. "Hello... Lisa?"

The pretty witch who had just opened the door, face partially hidden behind a sleek green beaded mask, grinned up at them. "Good job! Although I guess since I'm the one throwing the party I shouldn't be that surprise," she said laughing. "Mmmm... Rob and Paul!"

"How'd you know?" asked Paul, bemused. The Zorro costume covered him up pretty well he thought.

Lisa grinned at him. "You two always show up to everything together. Without Rob's blonde hair I might not have recognized him, but you've got a pretty distinctive jaw line and put the two of you together..."

"Okay, okay," Paul said rolling his eyes. "Stop now before we have to break out in a rendition of 'Guy Love.' You make us sound like an old married couple."

"You wish dude," Rob punched his shoulder.

"Go enjoy the party guys," Lisa said, shoeing them off. "The bar's downstairs and it's turning into a dance party down there, we've got jello and syringe shots, kegs are on the back porch and beer pong is in the garage."

"Fantastic," said Paul, heading off towards the back porch. Rob followed him and he returned to the conversation they'd been having. "So you have no idea what Lily's being for Halloween? That's kind of weird isn't it? Usually she won't shut up about her costume." "I dunno," Rob answered a little distractedly as he looked around the party, unleashing his most charming smile on a small group of half dressed women giggling and standing in a corner as they talked. "I think she's still mad at me after I told her off for trailing after us all summer. Last week she said something about that maid from Clue."

Yvette. Paul stifled a groan at the image that flashed in his head of Lily in Yvette's outfit. Sweet mother of all that was holy. For the first time that night he thanked his lucky stars that Lily had decided to attend a different party. He'd spent all summer doing his utmost not to notice how well she filled out her bathing suits and those tiny sundresses, had been perfectly respectful during the times when she'd needed help with her sun screen, and had finally had to admit defeat to himself and hint to Rob that it would be nice if they could have more guy time. Although Rob didn't know it was because Paul had been at the end of his rope when it came to restraint from Lily, who had grown up all too fast and all too well.

He couldn't even hint that to Rob because he had no doubt that his best friend would cheerfully kick his ass if he had. Well, try to kick his ass anyway. But Paul probably wouldn't have fought very hard because he wouldn't be able to blame Rob for doing so. If he found out that any guy had been having thoughts about Lily like the kind of thoughts that he was, he'd cheerfully kick that guy's ass.

Suddenly Lily's absence from the party seemed like a very bad thing. Especially if she was prancing around in a Yvette outfit with her mile long legs and those gorgeous boobs pushed up and-

"Here." Automatically Paul took the cup of beer from the Rob, only now noticing that he'd blindly followed his friend out onto the back porch. Thank god. He needed booze to clear away the rage that he felt at the idea of some ass wipe hitting on Lily... God he hoped she hadn't gone as Yvette. Not without him there to watch out for her. Although who would have kept him in line then?

As forbidden fantasies went, Lily dressed as Yvette and laid out naked on his bed had to be-

"Dude are you okay?" Rob helpfully interrupted his reverie for the second time in two minutes. He gave himself a small shake and took a sip of beer to snap himself out of it.

"Yep, good, just trying to decide where to go next."

"I'm going to go back to that group of girls we saw," Rob said with a wicked grin, heading back inside.

Girls. That was a good idea. Something to get his mind off of Lily. Maybe he could find someone to derail his thoughts and fantasies from the utter train wreck they'd slowly devolved to this past year. That would be ideal.

Stepping back into the house he was almost immediately halted.

"Oooo cool costume!"

"Thanks," he said, smiling down at the pretty girl. Her mask and wig covered enough that he couldn't tell if he knew her or not.

"What are you? A highwayman?"

"Ah sort of. Ever heard of Zorro?"

The slutty Raggedy Ann shook her head. Dressed up as a doll and didn't know Zorro. Talk about a warning sign for jail bait. Giving her a casual smile he was preparing a friendly brush off when a vision in pink and white sidled up to them.

"Don Diego, is that you?" she quipped. Just seeing her coming up behind Raggedy Ann had made his dick twitch a little. Like most of the female population at this party she was dressed to be noticed, but her outfit was slightly more covering than a lot of the other women's. It was also hugging her like a second skin, all the way to where it ended very abruptly at the tops of her thighs, showing a nice expanse of leg until you got down to just above her knees where the boots started. The fact that she recognized his outfit, and knew Zorro's real name, made the rest of him come to attention.

"Shh," he grinned at her, a real smile this time. "You'll ruin my secret identity."

She laughed. "You need to work on your accent."

"I didn't use one."

Goldeniangel
Goldeniangel
12,558 Followers