New Year's Eve With Tiffany

Info silverhawk
25 Dec. '19

I’d been looking forward to New Year’s Eve since Thanksgiving.  That’s when I started planning what I was going to have Tiffany do at the party I was taking her to.

Now, it might sound odd when I say I was going to have Tiffany do something, but if you knew Tiffany, you’d understand.  On the outside, Tiffany looks about like any other woman, though she has really big tits.  It’s on the inside that Tiffany’s a little different.  Well, truth be told, Tiffany’s a lot different than most women.  It was a little confusing at first.  

See, Tiffany is what you might call a closet exhibitionist.  What that means is she gets a real thrill out of knowing men are looking at her and the more they can see, the bigger the thrill.  She’s also too shy to do anything about that secret desire.  That’s where I come in.  She likes me to tell her what she has to do.

She always says she can’t, but she always does, and she gets hot enough she’d fuck me in the middle of the street in front of her house if I didn’t stop her.

I thought what I’d been planning was something she was going to like although she’d be mortified at first.  That’s what I’d been planning on, that she’d be embarrassed to death, but enjoy every second of it.

It had taken me three weeks of searching on-line to find the dress I was going to have her wear.  The stockings weren’t anything special, just black stockings with elastic lace at the tops so she wouldn’t need a garter belt.

The night before New Year’s Eve, I packed the dress and the stockings in a box, put a big red bow on top, and drove to Tiffany’s house for dinner.  Tiffany’s a great cook, so dinner was great.  The look on her face when she opened the box was more than I could have hoped for.

The package the dress came in was about the size of a sheet of notebook paper and almost as thin.  Tiffany took the dress out of the package and held it up.

“Are you sure this is the right size?  It doesn’t look like it’s going to fit.”

I grinned.

“It’s ‘one size fits all’, so I know it’ll fit.”

Tiffany shook her head.

“I think I have too much all in a couple of places.”

“Well, go try it on.  It’s what you’re going to wear when we go to the New Year’s Eve party at The Last Chance.”

Tiffany was in her bedroom for almost ten minutes before she came out.  When she did, the look on her face was fear, but I saw the way her eyes were open and shining.

That black dress was made of some kind of material that stretched in all directions.  It was cut low enough in front the top half of Tiffany’s bra cups showed, and it was short.

“I can’t wear this.  My bra shows and so do my panties.”

“Hmmm…turn around so I can see you from the back.”

Tiffany turned around and I smiled again.  The crack of her ass would have been showing if it had been cut any lower.  The hem hit her just below the crease between her thighs and ass cheeks.

“Tiffany, I think it’s fine.   It won’t show anything when we go to the party.”

She turned back around then.

“I don’t think they make a bra that won’t show, or panties either for that matter.”

“Well, they can’t show it you’re not wearing them, now can they?”

Tiffany’s face and chest turned the cutest shade of pink then.

“You want me to wear this without a bra and panties?  My boobs will be flopping around all over and my nipples will show and, and, and, with no panties anybody will be able to see my…my…my…up there.”

I chuckled.

“Well, that’s the general idea.  I like the idea of other guys seeing your big tits and hairy little pussy.”

“But you know how I’ll get if they do.”

“Yep, I’m counting on it.  Go try it on that way and let me see how it looks.  Put the stockings on too and wear those black heels you like so much.”

About five minutes later, Tiffany came back into her living room.  If anything, she was pinker.  She was also hot enough I wanted to fuck her right then and there.

“I might as well go naked.”

“Nah, you’re all covered up… well, I can kind of see your nipples because they’re darker, but that all.  They won’t show because it’ll be dark except on the dance floor.  The guys are gonna love you.”

Tiffany’s eyes were pretty wide open by then, and her pupils were dilated.  I’d seen that often enough I knew what it meant.  Tiffany was hot to trot.  I really wanted to just bend her over the back of the couch and fuck her right then, but that wasn’t part of my plan.

“Tiffany, come closer so I can see you better.”

It was like I’d planned on.  Tiffany’s ass swayed from side to side as she walked and the dress started to ride up her hips.  By the time she’d walked about six feet, I was seeing the dark brown hair on her pussy lips peeking at me from under the hem of the dress, not a lot, but enough I could tell it was there.

Tiffany felt it too.  She stopped and pulled the dress back down over her ass.

“I’m going to spend all night pulling this dress down.”

I chuckled.

“You might not want to pull it down quite as much.  Your nipples are showing now.”

Tiffany looked down, gasped, and pulled the dress up until her nipple beds were covered again.

“Do I have to wear this?”

“Well, it’s too late for me to find anything else.  I guess you could go naked if you want.  They guys would like that even better.  Come closer. I want to see how it looks on you close up.”

By the time Tiffany was standing in arms reach, I saw her pussy hair again.  I reached out, slipped my hand up Tiffany’s inner thigh, and then stroked her pussy lips.

“Yeah, this is gonna do just fine.”

I stood up then.

“I’ll pick you up at about seven.  Don’t eat too much for dinner.  They’ll have finger food at The Last Chance, so we’ll eat there.”

Tiffany caught my arm.

“Aren’t you going to do me now?”

“No.  I want you so hot tomorrow night you’ll want me to fuck you right there on the dance floor.”

“You wouldn’t really do that, would you?”

I grinned.

“We might find out.  I’m sure everybody would like seeing you cum hard right there in the middle of everything.”

I left then, and I knew what Tiffany was going to do.  She was going to think about all the guys at The Last Chance staring at her.  Then she was going to wonder if they’d want to fuck her.  Then she’d be imagining me fucking her on the dance floor while every body watched.  Then she’d get so worked up, she’d finger her pussy until she came.

That would take the edge off a little, but not much.  She’d be thinking about that all the next day too, and by seven, she’d be ready to do anything I asked her to do.

When I picked Tiffany up the following night, she met me at the door wearing the dress, stockings and heels, but she also had on a long coat.  She looked at me sheepishly.

“It’s cold outside so I wanted to stay warm.”

“Tiffany, it’s not cold enough for that coat.  You could go to the North Pole in that coat.  All I have is a light jacket.”

“Yes it is.  After I got dressed, I went out in my back yard.  It’s cold enough my nipples got all stiff and they show.”

“Well, nobody’s gonna see them in my truck except me.”

“Well, somebody might.  I’ll take it off after we go in…probably.”

She wouldn’t show me, but I had a pretty good idea about what she looked like.  Tiffany’s nipples aren’t all that big most of the time, but when they get stiff, they’re as long as my middle finger is wide and as big around as my little finger.

I’d picked The Last Chance Saloon And Whorehouse as the place where Tiffany and I would celebrate New Year’s Eve, and I’d picked it for a reason.  Unlike most bars, it has pretty loose rules about what you can and can’t do.  That’s because the owner understands what brings people to a bar.

The dress code for guys is pretty simple.  You have to be wearing pants or shorts, a shirt with sleeves, ball caps have to have the bill facing the front, and you can’t wear spurs.  The dress code for girls is even simpler.  Anything a woman wants to wear is OK, as long as she’s not showing nipples or her pussy.  I was maybe stretching the rules with Tiffany’s dress, but it was New Year’s Eve, so the security guys would only be pretty lax about what happened.  The more fun people have, the more they drink, and the more they drink, the more money the bar makes.

The last New Year’s Eve party I’d been to there had been interesting.  There were at least three girls there wearing jeans with the legs cut off so short the only leg left was the seam between their legs.  After ten minutes of them line dancing, it was obvious one wasn’t wearing panties.  That seam had pulled up between her pussy lips and those lips stuck out on either side.

I paid the cover and then walked Tiffany to a table and asked if she wanted to take off her coat.  Her face turned pink.

“I think I better leave it on until I get warmed back up.”

Her face had turned pink, but her eyes were wide open.  I knew she wanted to take off that coat but was afraid.

“Tiffany, nobody’s here yet.  Open your coat and let me see.”

Well, she was right.  Her nipples stood out like sewing thimbles.  

“Tiffany, I can hardly see them.  Let me go check your coat so somebody doesn’t steal it while we’re dancing.”

She unbuttoned it, then let me slip it off her shoulders.  I smiled, because she was smiling too.  

“OK, I’ll go check your coat.  You sit down and when the waitress comes over, order a beer for me and whatever you want to drink.”

When I got back to our table, Tiffany was sitting there with her arms crossed over her chest and her legs tightly closed.  I asked if she’d ordered us a drink and she said she had.

“Well, let’s get something to eat then.  The food last year was great.”

Tiffany looked at me and shook her head.

“You know what happens if I walk in this dress.  Why don’t you go and bring something back to me?”

“Nope.  There’ll be too many things to chose from.  If I bring you one of everything, you’ll say it’s too much.  Come on…there’s still nobody here.”

It was fun watching Tiffany walk to the wall with the food tables.  She’d take about four steps, then stop and pull the hem on her dress down, then look at her chest and pull the top back up.

When we filled our paper plates there were a few guys filling theirs, and they didn’t try to hide what they were thinking.  I’d intentionally gotten ahead of her a little.  A guy I knew named Bobby Lee stopped in his tracks because Tiffany had to lean over the table to reach the pot of meatballs.

“Holy fuck”, he blurted out.  

I saw Tiffany pull her dress back down then, but she was grinning.  I knew then it was going to be a great night.

Nothing much happened while we were sitting at our table eating.  Tiffany had her shoulders rolled forward and her legs crossed tight.  The DJ played a slow song about the time we finished eating, so I asked Tiffany if she’d like to dance.  She blushed bright pink.

“If I do, my dress will ride up and everybody will see me.”

“Nah, I’ll put my hands on your ass and hold your dress down.”

“You promise?”

“Yeah, I promise.  Come on before the song’s over.”

Once we were on the dance floor, Tiffany draped her arms around my neck and pushed her tits into my chest.  I put a hand on each of her ass cheeks and gave them a friendly squeeze.  Tiffany whispered in my ear, “Don’t do that.”

“Don’t do what?”

“Don’t squeeze my butt.  You’re making my nipples get stiff.”

I chuckled and squeezed her ass cheeks again.

“Well, I can’t hold your dress down unless I have my hands on your ass.  Would you rather I just put my arms around your waist?”

“Oh God no.  By the time we get done, I’ll be showing my butt to everybody.  Just don’t squeeze.”

Well I didn’t squeeze her ass cheeks again, but I did sort of hike up the hem a little at a time, slow enough that Tiffany didn’t notice until Jack danced by and said, “That is one fucking great ass you have there, Honey.”

I felt Tiffany push her big tits into my chest a little harder when she whispered, “Why did he say that?”

I chuckled.

“Well, it’s probably because about half of your ass cheeks are uncovered.”

“You didn’t.”

“Well, sort of.  I was holding your dress down, but it slipped up anyway, so I’m holding it where it is.  Don’t worry, I don’t think he could see any pussy hair because you’re standing up.”

“Oh God, he’ll think I’m just white trash.”

I squeezed Tiffany’s ass.

“No, he’s just thinking he’d like to fuck you.  Oh…you should see the look on Randy’s face.  He wants to fuck you too.  After this dance, I’ll go ask them both if they’re busy after the party.”

“Oh God, don’t do that.  I don’t know what I’d do with two men.”

I ran a fingertip between Tiffany’s ass cheeks and grinned when her ass tightened up.

“Well, it’d be three men.  You don’t expect me to just watch, do you?  You could handle three.  Randy told me Shirley likes being fucked in the ass, so I’d bet that’s what he’d want.  You could suck my cock while Jack’s fucking your pussy.”

The song ended before Tiffany could say anything.  She took her arms off my neck and pulled her dress back down over her ass, then started walking back to our table.  I followed her and watched her dress ride up her ass again.

She was halfway there when the DJ played another slow song.  I was going to catch up and take her back out on the floor, but before I could, Rick walked up, put his arm around Tiffany’s shoulders and said something to her.

She shook her head and kept on walking but forgot to pull her dress back down.  By the time she got back to our table, that little fringe of dark brown hair on her pussy was showing.

Tiffany did pull down her dress then, just before she climbed up on her stool, but it didn’t do any good.  As soon as she sat down, it rode up again.  I pulled my stool up beside her and sat down, then put my hand on her thigh.

“I just saw your pussy hair.”

“Oh no…did anybody else see?”

I chuckled.

“Well, Jerry choked on his beer, so I’m pretty sure he did.  Marty’s girlfriend hit him on the arm, so he probably did too.  He’ll have to lick her pussy tonight to make up for that.  Bet he was wishing he could lick yours instead.  You wouldn’t mind that, would you?  I can go dance with Myrna while you two go out to his pickup.  I hear his camper is pretty nice inside.”

I slipped my hand up Tiffany’s thigh until I felt hair.

“Damn, Tiffany, you’re wet.”

“I know.  He wouldn’t really want to lick me, would he?”

“Well sure.  He’d want to fuck you after that too, so I might have to dance a few dances with Myrna so you had time.”

“You wouldn’t let him do that to me would you?”

“Well, normally I wouldn’t, but you getting wet and all, I thought you might like it.  What did Rick say to you?”

“He just wanted to dance with me.  I told him I only dance with you.”

I grinned.

“He just wanted a feel of your ass cheeks.  They feel really great.  I’ll bet he’d like giving them a few squeezes.”

“No, that’s OK.  I’m good just dancing with you.”

It was then I looked at Tiffany’s chest.  There was no missing the two bumps her nipples made.

“Damn, Tiffany, your nipples are hard as rocks.  I think you wanted Rick to feel your ass cheeks, didn’t you?  Maybe you wanted him to do more to you too, like run his finger down your crack, or maybe you’d rather he cupped your ass and slipped a finger in you.”

Tiffany’s eyes were wide open and bright and shining.

“He wouldn’t do that right on the dance floor, would he?”

“Well, it was all I could do to keep my fingers away from your pussy.  Now that I know you’re wet, I’d probably do that too.”

Tiffany looked at me with the look I’d seen many times before.

“I think I want to go home now.”

“You sure?  Half the guys who are coming aren’t here yet.  They won’t get to see your ass and your stiff nipples.”

Tiffany wiggled on her stool.

“Yes, I’m sure.  If we stay any longer…well, I’m going to have to do something or my dress is going to be wet too.”

“OK, if that’s what you want, I’ll go get your coat.”

I hadn’t intended to stay until midnight anyway.  It was already getting pretty drunk in The Last Chance, and in another two hours, it was going to get pretty rowdy.  Before I met Tiffany, I’d have been there, sucking down a beer and trying to get one of the girls to go home with me.  Now, I just wanted Tiffany like I knew she’d be.

It took my truck about five minutes before the heater started blowing hot air, but once it did, I reached over and slipped my hand between the buttons of Tiffany’s coat.  Her nipples were still hard, and she caught her breath when I stroked the left one.

“Tiffany, we have a twenty minute drive to your house.  How about unbuttoning that coat for me?”

Tiffany shook her head.

“No, I can’t.  Somebody will see what you’re going to do.”

I pinched her nipple through her dress and Tiffany let a little moan slip from her throat.

“What do you think I’m going to do to you?”

“You’re going to play with my nipples and put your hand between my legs.”

I chuckled.

“Well, I might do that, but nobody will see you…well except that cop up there on the corner, but he’s watching for drunks, so unless I give him a reason, he won’t stop us.  I could do that if you want.  I’m sure he’d have a ball searching you.”

“No, that’s all right.  Let’s just go home.”

I pinched Tiffany’s nipple again.

“Well, unbutton that coat or I will.”

Tiffany unbuttoned her coat then, and when I slipped my hand up her dress, she scooted down in the seat and spread her legs.  She jerked a little when I ran my fingertip down over her clit, but she didn’t stop me.  I knew she wouldn’t.  When Tiffany gets aroused by showing herself, she gets so hot the only thing that calms her down is cumming, and then not for very long.

I wasn’t about to let her cum though, not until we got to her house, I got her out of that dress, and was licking her wet pussy.  I just wanted to keep her on the edge so she’d cum really hard that first time.

We’d gone about ten miles when Tiffany started to breathe pretty hard, so I told her to play with her tits.  It didn’t really surprise me that she did.  What surprised me was she pulled her tits out of the top of the dress and started rubbing her nipples.

Five miles later, Tiffany was starting to moan and arch up into the finger I had inside her pussy, so I pulled my hand back to the steering wheel.  Tiffany gasped, “Don’t stop.  I was almost there.”

I chuckled.

“Nope.  I want you to cum all over my face and I can’t do that and drive at the same time.  We’re almost there, so just keep playing with your tits.”

It was funny watching Tiffany walk up her walk to the door.  She was trying to hold her coat closed and walk fast at the same time, but she could only hold the top closed.  When the bottom opened, she shuddered and reached down to close the coat, and when she did, her bare tits popped out into the cold air.  She shuddered, said, “Oh God, I’m freezing out here”, and started to walk faster.

If I hadn’t already been ready to fuck anything with a hole, Tiffany’s big tits flopping around would have done it.  By the time we got to her front door, my cock was standing tall.  

Once we were inside, Tiffany shut the door and then pulled the dress down over her ass and stepped out of it.

“I’m so hot it feels like I’m dripping.  Do me now.”

I picked her up, carried her to her bedroom, and plopped her ass down on the bed.  About thirty seconds later, I’d kicked off my boots, stripped, and was kneeling between Tiffany’s spread thighs.  

Usually, she have told me not to do what I was going to do, but that was just the way Tiffany is.  I guess this time she was so hot she didn’t care.

She wasn’t dripping wet, but if that drive had been much longer, I figure she would have been.  As it was, her pussy hair was damp, and just inside her pussy lips she was as wet and slippery as if I’d rubbed her clit and sucked her nipples for half an hour.  

I didn’t waste any time.  I just stuck out my tongue, spread her pussy lips with my thumbs, and pushed my tongue into her entrance.  Tiffany gasped, and grabbed my head.

It didn’t take her long before she dropped her hands to the sheet and started clawing at it.  I suppose that was because I’d started sucking her clit and rolling her nipples at the same time.  That’s what usually makes her do that.  

A few licks and a couple firm pulls on Tiffany’s thick nipples pushed her over the edge.  She cried out, “Oh my God”, and arched up into my face.  She hung there while I sucked her clit, her thighs quaking against my ears, and then finally gasped and fell back down on the mattress.

I nibbled my way from her pussy to her nipples, sucked each one a little, and then raised up to look at Tiffany’s face.


Tiffany grabbed my back and tried to pull me forward some more.

“No.  Put it in me.”

“All ready?  I thought you’d want to rest a little first.”

Tiffany arched her pussy up and tried to find my cock.

“Just put it in me, she moaned.  “I’m ready.”

Well, she was, more ready than I was, but that was a good thing.  When Tiffany gets so aroused she wants to be fucked right after she cums, it’s so erotic I have trouble not getting ahead of her.  It’s how slippery/sticky wet she gets inside and the way she moans when I suck her nipples and the way she keeps rocking her ass into every stroke so my cock goes inside her deeper.

Tiffany was doing all that, so I caught up pretty fast and then had to start holding back.  I was doing OK until it felt like she was opening her pussy and then closing it around my stroking cock.  I almost lost it then, so I whispered, “Tiffany, rub your clit.”

I felt her hand slipping between us, and then her fingertip on the top of my cock.  A second later, Tiffany moaned and I felt her tummy roll.  

She rubbed her clit slowly at first, but then started to speed up.  When she did, she started lifting her pussy up and into every stroke.  I knew I wasn’t going to last very long if she kept that up, so I bit her left nipple a little.  Tiffany caught her breath and held it as she arched up off the bed.  When she was starting to lift me too, her thighs started to shake.  A second later, she screeched and started rocking her pussy over my cock so fast all I could do was try to keep it inside her.  

I bit her nipple again and then pulled my face away from her chest.  She screeched again, dug her nails into my ass cheeks, and came hard.  I didn’t even try to stroke my cock in and out then.  I let the contractions in Tiffany’s passage take me the rest of the way.  I think when I groaned as the first shot splattered inside Tiffany, she shook more, but I’m not sure.  I was cumming so hard it was hard to think about anything else.

Tiffany sighed then and sank back down on the mattress and pulled me down with her.  She nibbled my ear, and then whispered, “Again.  Do me again.”

“Right now?  I can’t.”

“Use your fingers then.  I’m still so worked up I’ll never go to sleep.”

Well, she finally did go to sleep, but not until I’d fingered her until she came and then fucked her one more time.  Well, the second time she climbed on top of me and rode my cock so it was really her fucking me.  I love it when Tiffany rides my cock.  She’ll dangle her big tits over my face.  I’ll catch a nipple between my teeth, and as soon as she feels that pinch, she pulls back.  I’d think that would hurt like hell, but all it does for Tiffany is cause her pussy to get wetter.

The next morning, we were sitting at Tiffany’s kitchen table drinking coffee.  Well, that was after she wanted me to fuck her again.  That’s usually what happens.  She wakes up horny and won’t let me get out of bed unless I make her cum even if it’s just with my fingers.

Tiffany put down her cup and smiled at me.

“You were just kidding last night about what those men wanted to do to me, weren’t you?”

“No, I’m sure they wanted to do what I said and probably a lot more.”

Tiffany grinned.

“Like what?”

I shrugged.

“Well, I know Marty likes to lick pussy, and after he saw your pussy hair, I expect he’d want to find out how you taste.  I expect the others would want to do that and then fuck you.  They’d probably want to fuck you more than once too.  I know Bobby Lee would want to fuck you from behind at least once.

Tiffany smiled shyly.

“Like you did last night?”

“Yeah, like I did last night.”

Tiffany got out of her chair, pulled off the robe she was wearing, and then bent over the table.

“Do me again like this.”

Well, what can I say?  If it wasn’t for the fact that Tiffany gets hot from showing herself, I’d feel bad about making her do that.  As it is, well, I like watching her showing herself and I like how she needs to be fucked when she does.

We won’t have too many opportunities for her to do that, not until spring gets here and it warms up enough.  I think tonight, after I’ve gotten her naked on her couch, I’ll tell her I forgot to close the blinds and her neighbor is probably watching us and jacking off.  That oughta be good for at least one good fuck…maybe even two.