Winter Lottery - Cover

Winter Lottery

by LiteroCat

Copyright© 2020 by LiteroCat

Erotica Sex Story: A department ski trip has a secret agenda. Many spend the week naked as the boss satisfies his wife's request to bring home a stranger for a special prize. She slowly strips for them and is surprised as she gives the stranger his prize.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Mult   Consensual   Heterosexual   Fiction   Sharing   Wife Watching   Anal Sex   Cream Pie   Exhibitionism   Oral Sex   Petting   Safe Sex   Squirting   .

During a week-long, employees-only ski trip, I got to know my accounting department much better than I ever expected. For the smaller crowds, we went to a startup mountain ski chalet between winter holidays. Most of us don’t ski so we were there for the pristine snow scape, department morale, spa benefits, and to ogle the ski bunnies during that adults-only week.

Starting with the first night, a promise of holiday gifts kept everyone together every night for dinner. After our first group dinner, I burst into the room naked except for a Santa hat, beard, black belt and boots. Mari, a confident nudist coworker, dressed the same, without the beard, was happy to display her average body to our group. She was one of us, but always felt overdressed in the office no matter how little she wore. This was her way to indulge her exhibitionist compulsion and ensure that every man and woman would get a good look at her oversized, firm tits and shaved pussy.

We took our time presenting everyone with a gift card and ignored the liberties they took with her damp pussy and my semi-hard cock. I announced that I would present more gifts during the week and would have a special lottery with only two special prizes. Mari and I turned and bent sharply to show them our full moons and deep craters then ran out the door laughing. I heard Howard, probably our shyest, and certainly our oldest, worker say, “Well, that sets the tone for the week. I wonder if they expect all of us to be nude all week — or even if we need dress for dinner.” Was that wishful thinking or was he just trying to fit in with the younger people?

The pool and Jacuzzi were ‘clothing optional’ and most of my crew took advantage of it — males and females. While I generally ignored naked men and dreamed about the naked women, this trip, I had to be more balanced. Howard never used the sauna and never went nude, as I predicted, though his swimsuit was obviously well stuffed. When I approached him at the bar to confirm my premonitory selection, I looked for more background and family info.

“So, Howard, I understand that since your wife passed twenty-five years ago you’ve only had two serious intimacies. Are you OK? You seem sociable, yet you don’t date and seem lonely when not performing. Are you off women and relationships?”

“Thanks for asking, Ger. I’m OK. No, I’m not off women, but at seventy-four, I don’t have much to offer to attract them. I quit my last sex partner five years ago and don’t date. Since I’m in middle age, I have plenty of time. You know, snow on the roof doesn’t mean the fire’s out in the hearth. Mari coming out naked like that sure fired up my hearth. It’s good I was dressed or I would have scared a few people with mini me.”

“Gotit. The equipment still works, but you have no one to instill it in. Middle age? So you expect to live to 148? You know you have to use it too so you don’t lose it. Even Rosey can help you keep the rust off it. I bet most of these women will be naked most of the week and would love to see and coax mini you.”

“Rosey Palm and her five sisters? Yes, she has been a frequent help. I’m resigned to being alone. Mari is the first live naked woman I’ve seen in five years and that did make my heart ache a bit. I do long for a loving pussy to taste and fuck, but that’s life. Getting old isn’t for sissies.”

Yes, I think he is the right one for my special winter lottery prize. I suppose I need to chat with some women too so I’m not too obvious. About half our happy group stayed naked all week, even to dinner, while the rest stayed partially dressed, yet enjoyed the naked bodies around them — except for Howard and Ann, our other shy introvert.

At our last dinner, I had everyone write their name on a paper strip and put them in bowls — one for men the other for women. As they passed the bowls around, I explained this random drawing was for the special prize. They would meet my wife soon after the new year and spend some quality time with her and

me at our home. We would present their secret prize then and ask it stays secret. When the bowls came back to me, I drew a strip from the female bowl and announced Ann won. I dropped the strip back in the bowl so no one could tell whose name I actually drew. I did the same with the men’s bowl when I announced that Howard won. Eyes and mouth wide open, I’d never seen him so shocked. So it wasn’t quite random. I was under orders from my wife, Cozie.

What happens on an adult ski trip stays there. Yet, I may reveal that another time. Once we got on our warm chartered bus, we all stripped, except for Howard, and rode home naked and singing.

My wife is a blatant exhibitionist still exploring new challenges. She had been asking me to bring home a stranger, i.e., someone that I know, but she doesn’t. When our ski trip came up, I used it the find someone who might be a challenge — Howard.

Rather than just flashing in public, she wanted something more limited and yet more intense for a change. Beyond that, she left me in the dark about how far she hoped to go. I let her set the conditions and limits alone. For our first exercise, I chose Howard to come visit since he was in his seventies, balding and clearly overweight. I knew there would be no attraction to him, but I was sure he would lust over Cozie even while she was fully dressed. With his long lapse with sex, he was also safe to play with and unattached, no shock. He didn’t know the surprise she had for him, but neither did I.

With the days getting longer in January, it was still bright and warm out when Howard rang the bell on our open So Cal door. I let Coz answer so I could watch Howard’s reaction. I deliberately hadn’t shown him any photos and never described her as anything but ‘average’ for a forty-year old. Well, in my most unbiased assessment, if ‘pleasantly average’ is 50 then Cozie is a strikingly hot 75. By the way Howard’s face lit up, he agreed. All the while his extended hand hovered before her, I watched his enthralled eyes quickly scan her svelte shape then return and get mired in every detail of her. She was pleased too as he licked his lips and undressed her with his obvious stares.

Eons passed as he glossed over her medium length, light brown hair, her pools of deep blue eyes, her petite and perfect ski jump nose, her bright and enthralling cupid-white smile. Finally getting past her inviting neck, he struggled to see under her open vest and mild cutoff tank top to assess her tits. Despite the three open buttons on her top, they hid from him, so he continued to her bared abs, paused and fixed on her modest skirt and lingered at its fastener. Before he salivated at her shapely calves, she grabbed his hand and, leaning forward, shook it and herself. I smiled as I watched him try to drop her skirt telekineticaly. His light Bermuda shorts did nothing to hide his huge and growing bulge. She drew him inside and left the door wide open.

I reminded Coz that Howard won the winter lottery and we owed him a special prize. Her eyes twinkled and her lips smiled as she said she remembered. We all sat on a sofa and chatted openly until Coz got up to get some drinks. He was obviously dazzled by her smile and guile. His eyes followed her loose skirt and swaying ass into the kitchen. “I thought you said she was just average looking. She’s hot!”

“You should tell her that yourself. She loves flattery and may relax and reward you with even nicer views.” She came back with drinks on a tray and a large-faced timer. She made a show of bending, away from us, at the hip as she stood before us and slowly, seductively, placed our drinks on the low coffee table. The show centered on her shapely legs and the ever rising skirt that revealed more and more of them as she bent lower and lower. Howard subtly shifted his slacks to lighten the strangle hold on his swelling bulge. Her eyes lingered on his already thick rod. She marveled at its rise considering his age.

Cozie straightened and moved to the other side of the table. She bent the same sultry way and placed her drink and the timer on the table. Her vest fell openly away, her tank top billowed and her lacy bra appeared. She aimed her chest at Howard, knowing full well that her full D-cups were shifting and straining the flimsy wonder bra. Howard was thrilled. Such a tease!

“Um, you should punch your husband for lying about you. I know he can’t believe it, but he said you were ‘just average’ looking. I have to say you are very pretty and I apologize for staring.” Her grin was radiant, her bright eyes flirted as she set the timer for ten minutes, sat back into our red leather Carver chair across from us and dramatically crossed her legs slowly.

As Howard squirmed, she fought off a smirk and enjoyed his torture. “Why thank you, Howard. He thinks I’m much prettier than I am.” Between asking about where he grew up, went to school, his hobbies, etc., she recrossed her legs and let the skirt rise a bit higher each time. When she scooted forward for her drink, her knees gaped a bit and, since I had moved nearer to our stranger, we both got a glimpse of bright yellow panties. Cozie started the timer then changed her mind and stopped it and reset the time to eight minutes without comment or explanation. As she ‘struggled’ to slip off her shoes, one knee briefly fell far from the other to yield a fleeting, yet profound and wide view of her teasing panties. We both angled our heads for a better view of any trace of camel toe. I didn’t see any.

She slapped the timer to start its countdown, turned it so we all could see it, lifted her drink and leaned back in the chair before resuming with inane questions. I asked what the timer was for and her enigmatic answer was, “What timer?” As Howard answered about his school, sports, blah, blah, blah, she fidgeted and kept an eye on the timer. 4:52... 3:23 Two cocks enjoyed the views, yet failed to see any wetness. 1:09... 0:03... -ding-

Apparently ignoring the timer, she asked another insipid question, slid to the edge of the chair and casually removed her vest while thrusting her chest forward. I began grabbing photos of her exposure and Howard’s stiff reaction. He didn’t notice. She neatly folded the vest while keeping her chest stressing her blouse. As she carefully laid the vest on a side table, we stared thru her translucent blouse and clearly saw the outline and details of her demi bra. Her movements let us see the frilly upper half of the bra and a shadow of a demi nipple that was bisected by the revealing bra. She shifted forward again and tapped the timer reset. 7:59 ... One leg slowly swung as wide as the armed chair allowed as she settled in and her pristine yellow panties again waved at us. What was she playing at?

We discussed hobbies, diets, etc., 4:33... 2:11 ... Favorite types of TV shows... 0:02... -ding- Cozie shared that thoughtful SciFi is our preference ... as she slowly unbuttoned her blouse. “Babylon 5 is a masterpiece of drama, SciFi, character study, classic life events, morals, honor, sacrifices, political conflicts, wars, diplomacy, spirituality, consequences and hope above all, all written as ONE well arced novel of 110 chapters and five movies. So much more then simple SciFi.” She slid the blouse off her shoulders and neatly folded it. “Our favorite movies are Lathe of Heaven and Bladerunner, but I also like The Notebook and even The Lakehouse.” She laid the blouse on the vest and threw her shoulders back. One hard nipple and half the other were barely hidden by the frilly lace. Howard’s cock throbbed as he swallowed. His breathing deepened and sped up.

She shifted forward and reset the LCD counter. 7:59 ... As we stared through her bra, she pushed back and left her legs slightly agape. Howard licked his lips as he stared at her tempting thighs and panties. “We’re also big on procedural shows like all the CSIs, forensic files, medicals, legals, rescues...” She deftly stroked her toned abs then upward, to and over each modest, well rounded breast. As she pushed her cups up, her tits swelled and her tempting nipples threatened to escape. Our cocks responded positively, as her eyes lingered on our responses. She was already enjoying this a little too much. But it was her show and we were just the lucky audience. 0:02... -ding- “NCIS etc. How about you?”

Howard’s throbbing responses stopped and started as he watched her slide forward again. This time she let the skirt sit on her upper, slightly open thighs a moment before resetting the timer. 7:59 ... She stood and pretended to listen to Howard as she stared at his bulge. It noticed and throbbed again. While he tried to ramble on, she lifted her skirt to her groin, exposed all of her shapely legs and the very top of her sunflower panties. In the four breathless seconds she let us stare, we saw a dark, wet, growing pattern at their tip.

Her hands slipped under her skirt, snagged her panties’ waist and began to slowly slide them down. She let us see some of her teasing landing strip before pushing the tiny coverup down her legs and let it drop to her ankles. Her skirt all too quickly fell to mid thigh and ended her tantalizing display. Though still pretending to be casual, her chest heaved farther with each breath. My wife had already ‘nearly’ exposed her nipples and pussy to a stranger as I watched and conflictedly enjoyed it! She grunted at his response, which she didn’t hear. Howard was stunned at the brief, nearly nude, close up display. His cock obviously extended another three inches down his shorts. Cozie turned and bent sharply and slowly, letting her skirt hike up to her shapely ass in Howard’s face. She picked up her panties, blatantly unrolled them and sniffed her gusset as Howard’s fluttering mouth moved soundlessly. When she sat again, she let her legs drift apart, but her pussy was still in the dark.

I expected, or hoped, that she would toss the damp panties to one of us to savor. Instead, she folded them neatly and stacked them on her other clothes. She reset the timer. 7:59... “Maybe I shouldn’t admit this, but we also enjoy reading adult tales of sex on SOL and watching the occasional porn vids. Do YOU like that sort of thing?” Smirking, she leaned back, pointing her half-covered legs at Howard. Wasn’t it too late to feign subtlety? 4:12 “I, uhh, especially like the forced or accidental exhibitionist stories.” Howard groaned with anticipation as his cock surged again. He blurted out that he liked those stories too as well as the mind control and loving wives tales. 0:02 -ding-

 
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