The Masquerade Ch. 01

Story Info
Brad helps Tiffany get rid of her inhibitions.
1.5k words
4.23
16.2k
7
Story does not have any tags

Part 1 of the 2 part series

Updated 11/02/2022
Created 04/15/2014
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

Brad was frustrated with his long-time girlfriend Tiffany. She was easily the hottest girl he had ever dated. In fact, he'd rarely seen a more attractive woman anywhere else, including the porns he loved watching. She was slim but muscular. She wore a DD bra and everything was still high and tight on her where it was supposed to be.

Beyond that, she was warm and open with a great personality. She was able to hold an intelligent conversation with virtually anyone, and more than likely -- she was smarter than he was. Yes, she was the perfect package..... almost.

He had plenty of women before her. They all had some part of their personality that was great and he only dated attractive women. Tiffany beat them in all of those areas. Her only short-coming was her reluctance in the bedroom. She was willing to try almost anything, but after some of the freaky women he had "dated" he had tastes that ran a little freakier than most. So sue him. He tried to ease her into different situations and she was willing to do it -- but only so far.

When they watched a porn and had seen a girl being fisted, she was willing to try but asked him to stop before he got much in. When he told her he liked being an exhibitionist, she was willing to do more pda than normal -- but she wasn't really showing much. She was willing to let another woman join them, but she left it up to him to satisfy the visitor to their bed.

Tiffany's only part had been filming him and the girl going at it and occasionally fondling her tits. The night they discussed role playing and she mentioned wanting to try being the 'victim' of rape and being tied up had seemed awesome to him. Until she changed her mind before they really got started. She always had her limits.

He loved her and always respected her wishes. The problem is that he knew that if she would just let go of her inhibitions that she would love it as much as him. The other part of that was that he knew what he liked. He was thinking of asking her to marry him but could he do that knowing that he wouldn't sleep around on her behind her back, and still not have any of his freaky tendencies catered to occasionally? When his buddy David had told him about a party where there would be plenty of alcohol flowing and all inhibitions were to be left at the door, it sounded like the perfect time to see how far she would be willing to go. An added bonus is that it was a masquerade ball of sorts. Though there would be no ball gowns, everyone would be supplied with a mask of their choice to wear during the party. Supposedly, it helped people put down their insecurities. He was hoping he would be finding out.

The night of the party was upon them and Brad could hardly wait. He'd told Tiffany some about it. He warned that there would be lots of exhibitionists at the party and lots of liquor. She thought it was a great way to see what and how others were doing it. Maybe the alcohol would help her let loose a little. Brad couldn't agree more.

When they came in the door there were 2 people with trays. One had masks they could choose and the other had glasses of some fruity concoction for the women and beer for the guys. They chose their masks and drinks and were assured that there was plenty to drink all around and to enjoy the party. They put their masks on and entered.

He started looking around at the decorations but that didn't last long. All around him people were in various states of undress and Brad would rather look at that than the decorations. Tiff looked hot in her super short white dress that was almost see through but getting a glance around him, he hoped she would be like some of the other women and out of her clothes soon. When he glanced at her, she was taking it all in with a slightly shocked look on her face. He walked her in and tried to find some place a little quieter for them to watch while she got a few drinks in her. She sat on a stool while he stood next to her trying to be comforting while getting her loosened up at the same time.

A naked man approached them when the high heel she had been dangling off her toes fell off. "May I?" he asked as he picked the shoe up. She said nothing but Brad introduced them before the man -- Jay - bent down and grabbed her foot to put her heel back on. Sitting on the stool had hiked her already short dress up so it was barely covering her ass. When Jay grabbed her foot to move it and put the shoe on, he parted her legs slightly more to get a glance under the dress. He was greeted by a bare pussy that was glistening. He glanced up at her and smiled before sliding the shoe back on. As he stood watching her, he trailed his finger up her leg until it was under her dress and he barely grazed her wet lips. Brad was behind her and had slipped his hand down the front of her dress and massaged her tits.

Jay slid his finger in her as he bent down and took the large tit that Brad had just exposed, into his mouth. She gasped when he pulled away from her. He smiled before walking away. "That wasn't too bad now was it" Brad asked her.

"No." She responded. "I actually enjoyed it. I didn't think I would. I feel like I don't have to worry about anyone judging me with this mask on."

Relieved, Brad took her hand and helped her off the stool to go mingle. She had a few more drinks before a brunette walked up to Brad and had her hands in his boxers as she kissed him. They had shed the majority of their clothes a long time ago. The brunette stopped kissing him long enough to turn to Tiffany and kiss her as well. It was just moments before Brad was looking down at the brunette on her knees with his dick in her mouth. He was surprised when a second later he saw a twinkle in Tiffany's eye before she was on her knees next to the brunette and they both had their mouth on him. Taking turns on him turned into the two hot girls kissing and he watched as the brunettes fingers slid into Tiffany's wetness and Tiffany took the woman's tits into her mouth and started sucking them. Brad didn't think it could have happened, but he was harder than he was just moments ago.

Before long Tiffany was on her back with the brunette was between her legs. Brad took this opportunity to enter the stranger from behind. As he pounded into her she moaned and worked harder on Tiffany. Between the two women he couldn't tell which one was enjoying it more and he had never been more turned on. The brunette picked her head up for a moment and turned to look at him. "My ass. Put that big hard cock in my ass." He hesitated a moment before he decided to oblige her.

He started sliding in slowly not sure if he would hurt her. She was so wet that sliding out of her pussy into her ass, her own juices was all the lubrication he needed. After he was all the way in and pumped a few times she was telling him to fuck her hard. He had been watching his dick slide in and out of that tight asshole and when he looked at her he saw that she no longer had her mouth between Tiffany's legs and was only paying attention to how his cock felt pounding away at her. Tiffany was just watching with a hungry look.

He had to concentrate so he didn't cum too soon. But when Tiffany maneuvered under the brunette and he could feel her under them both to get to the brunettes pussy with her own mouth, it took everything he had not to cum. A minute later the brunette was screaming out and he could feel her cumming. He could feel the contractions while he was in her ass and he followed a moment later filling her ass with his hot cum.

He practically fell on top of her but collected himself quickly. He helped both ladies up and the brunette kissed them both before simply saying "Thanks" and walking away. They watched her for a moment before they headed to a bathroom to clean themselves up.

"So how are you liking the party so far?" he asked her. He was worried that in the aftermath she was upset. He chanced at a glance at her at the sink. She simply smiled and said "I like it a lot. Let's see what else is out there."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousabout 10 years ago
Let's have Ch. 02

Please continue the Masquerade adventures. Tiffany sounds like she is just getting warmed up, thus I'd like to know more about her adventures.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

White Sluts' Club: 40th Birthday Teacher takes 40 loads of black CUM a variety of unique ways.in Incest/Taboo
Christmas at the Strip Club I give a special performance at the staff party.in Exhibitionist & Voyeur
Jamaican Holiday Ch. 01 Vacation starts white couple's journey to being Black-owned .in Interracial Love
Black Cock Whore White wife punished.in Interracial Love
Bosom Buddies Ch. 01 A nerd befriends the 5 hottest girls in school.in First Time
More Stories