The Anchor Street Inn

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Six friends, one game, endless possibilities.
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Author's note: This story takes place in a world where STDS and birth control are things of the past.

*****

It was a cold, slow night at the Anchor Street Inn Tavern. The "inn" portion of the place is closed after summer, but the owners keep the restaurant and bar portion open for any tourists travelling to the mountains for a skiing holiday. Life on the Maine coast is a seasonal existence and the town of Criehaven is no different. My name is Ambrose, though I'm often referred to as "Rosie." I bartend at the Anchor Street Inn five nights a week while finishing up my degree. I'm twenty-six, single, six-four in height, a half-decent six pack leftover from my time in the military being quickly overtaken by takeout food and beer. I have dark brown hair and green eyes, and while I don't consider myself good-looking, I can't imagine it's just my charm that pulls customers back here. Maybe it's the charm of the place. It's old-world, old-money, leather chairs and mahogany wood, classic dishes served by the fire, smelling of pipe tobacco and faded aristocrats.

The clientele tonight was minimal as most nights in December were. There was me, of course, and Jenn as the only waitress. Jenn is sweet girl with honey-blonde hair, pale-blue eyes and tits the size of melons. I don't say that to be crude, but it's noticeable immediately upon meeting her, even through the black button-down shirt. She's not a thin girl, but that was fine by me. Savannah, the hostess, was still lingering around, waiting for the place to close, pretending to check the salt-shakers for fullness for the thousandth time that night. Savannah was rosy-cheeked and innocent looking, having only graduated high school the year before. She was the National Guard though, lending her an edge of toughness that I respected, as well as jet-black hair that suggested some sort of Native heritage. Her frame was thin, though she had a plump, sculpted ass and thick, powerful legs.

"Rosie! Stop staring at her ass!" Called a familiar, saucy voice from the bar. My only two patrons of the night were Amber and Sophie, waitresses at the Inn who bewilderingly spent their nights off here. Amber had long, red hair and a crooked smile. She had two children and was as kind as someone can be, though this was often hidden by her bawdy and upfront manner. Amber had wide hips and what appeared to be a decent rack, a theory I was always curious to test. Sophie was an usual specimen. She was six feet in height, skinny as a rail and half-Chinese by her mother's side. She was quiet but funny- and often dirty- in her own way. "I'm running low over here." Amber said, swirling her glass around. They were drinking gin and tonics and Sophie's face was flushed from the liquor.

"Hope you're not driving home." I said, pouring them another couple of cocktails. I wanted one myself, but I knew Candance, the manager, had a habit of popping spider-like out of the back office to inspect the restaurant and wouldn't tolerate anyone on duty drinking. "Supposed to be rough out there tonight. Eight inches."

"I could use eight inches." Sophie said, before the redness in her face darkened. I thought for a second Amber was going to fall out of her chair. We hadn't had a customer in hours and it was very nearly closing time.

"I'm calling it." Jenn said, removing her apron and sitting at the bar. "We should have closed an hour ago. That snow was looking pretty rough, the last time I checked."

"I'll peek outside." I offered, moving from my position behind the bar and leaving the Inn. What was before me outside was nothing short of apocalyptic. The entire world seemed to be blanketed in a foot of snow, all of which must have happened in the span of a few hours. The few cars in the parking lot weren't visible and no vehicles appeared on the roads. I quickly retreated inside to deliver the news.

"Where were you?" Asked Candance, who seemed to materialize behind the bar in my absence. Candance was tall, as tall as Sophie, with classical Scandinavian features, blonde hair, blue eyes, large breasts and a plump ass with long, shapely legs. She was usually as pleasant as a Viking raid, adhering to the terrorizing method of keeping her employees in line.

"Checking out the weather." I replied, giving her my biggest smile. "There's a foot out there, at least. Does anyone know any Uber drivers that moonlight as plow-truck drivers?"

After confirming the weather for themselves, our attentions turned to finding cabs and Uber drivers crazy enough to brave the weather. Once that was established as an impossibility, Candace threw up her hands in despair.

"What was I supposed to do? Predict the weather?" She said. All of us were sitting at the bar now, a sort of informal meeting with Candance doing all the talking. "Does anyone have any ideas how to get out of here?"

"We could just stay here." Suggested Savannah, eyeing the blizzard outside nervously. "I don't want to drive in this. I doubt anyone else does."

"I can't let anyone stay in the rooms. They're closed for the season." Candace protested. "Mr. Silverman would have my ass."

I knew that was a lie. Mr. Silverman, the owner of the Anchor Street Inn, was as kind and generous as a human being could be. Just as Candance was about to continue her rant, her cell phone went off. She spoke to the person on the other line, her part of the conversation being mostly in the form of "yes sir." Afterwards, she turned to address us all again.

"Mr. Silverman just called. We can't have the rooms- he said he would, but they're locked up and even I don't have the keys- but we can grab some linens and camp down here tonight if we need to."

"A sleep-over?" Jenn said, draining her glass of wine.

"With a guy?" Savannah said, her voice becoming both worried and excited.

"Well, I usually sleep naked, but I can hold off for tonight." I said, finishing my second drink. The booze was loosening me up, I could feel it. The girls laughed, Candance included. It almost sounded like she muttered "Ain't that a shame." The six of us went to collect our beddings and prepared a spot in front of the fire.

We formed a circle on the floor of the main area of the restaurant, the carpet being the kind you'd want to play a board game on. Booze and left overs were handed around, even Candance partaking in both. After about twenty minutes, it was Amber who took an empty bottle of scotch and placed it in the middle of the circle.

"Truth or dare. Let's play." Amber said, grinning her sideways grin. Everyone let out a nervous chuckle. The order of the circle was myself, Jenn to my left, Savannah, Amber directly across from me, Sophie and Candace directly to my right.

"I'm game." I said, grabbing the bottle. Amber put her pale hand over mine.

"Need to lay down the rules." She said, wagging a finger in my face. "If you take truth, you have to take off a piece of clothing."

"No!" Cried Savannah, blushing.

"Oh, come on. I can't sleep in my jeans. I don't think anyone else can. Besides... Haven't you always wondered what Rosie's packing?" She pointed to my crotch and squeezed one of Savannah's cheeks. Savannah relented and Amber went on. "If you refuse a dare, you have to take truth but you have to remove two pieces of clothing. Jewelry doesn't count. We play until the last person is dressed. Everyone agreed?"

No one protested, and I took that as a green light. I spun the bottle around before it landed on Jenn. Jenn giggled as she said "truth."

I started off with an easy one. "What's your bra size, Jenn?"

Jenn sighed and started unbuttoning her black shirt. Our shoes and socks were off by the time we settled in, except for Savannah who had kept her socks on. "38E, I think? They're huge. Such a pain to lug around." She threw her shirt to the side to reveal two massive mummeries contained in a sheer pink bra. Savannah, to everyone's surprise including her own, reached up and gave one a firm squeeze. Jenn giggled and playfully slapped her hand away. I felt my cock stiffen at the sight.

"It's your turn now." Amber said to Jenn. Jenn twirled the bottle around on the carpet. It landed on Candance, who rolled her eyes.

"Truth." Candace said.

"When was the last time you got yourself off and what did you think about?" Jenn asked, the booze clearly having a profound effect. Candance's eyes went wide with surprise.

"This... this morning, actually." She said, biting her bottom lip. "That's two questions. I'm only answering the first."

"And taking your shirt off!" Jenn said. Candace shook her head and reached under her blouse, somehow managing the feat of removing her bra through her sleep. I could see the outlines of her nipples pressed against the white fabric.

Candace spun the bottle around, stopping at Savannah. Candance grinned one of her most malicious smiles. Savannah was at a disadvantage. She was wearing a tight blue dress, as the dress code of the hostesses differed from the waitstaff. If she took truth, she'd have to remove the dress or her socks- which could be used as a last-ditch effort to stay in the game. Savannah had guts, I realized, as she looked her manager in the eye and said "Dare."

"Hmm," Candace contemplated, looking around the circle. "I dare you to sit on Rosie's lap and make-out with him for thirty seconds."

"Sure." Savannah said, looking at me with apologetic eyes. She climbed onto my lap, waiting for me to kiss her. She wasn't a bad kisser, but inexperienced, trying to much tongue, not realizing the sensation was in the lips. Her underwear rubbed against the growing bulge in my pants, an aching, unsatisfactory sort of grinding that left me harder than Chinese algebra. I nibbled on Savannah's bottom lip as Candance yelled "time!" Savannah climbed off me and I could see a wet spot up her dress. She spun the bottle around until it landed on me, fatefully.

"Truth." I said, crossing my arms in defiance at the girl.

"Have you ever thought about anyone here while you're... you know, tugging on it?" She said, shyly. I wondered if this girl was a virgin. It would explain a lot.

"Sure." I answered, truthfully. "We all work pretty close together. It's only natural." I stood up and removed my jeans, pausing for a moment to let the girls drink in the sight. My bulge showed pretty well through my boxer-briefs, though not representative of the whole thing. I spun the bottle around until it landed it on Amber, who smiled defiantly.

"Truth." She grinned. I knew I didn't have to pull any punches with this girl. She had her shirt off before I could ask a question, exposing two milky white, almost conical breasts, beneath a yellow bra.

"Who here have you fantasied about?" I said. "Specifics. I want details."

"This could take a minute. You, of course, Rosie. Remember when I had to host last month, and I wore that little red dress? I was hoping the entire night you'd take me back to the linen closet, pull my dress up, and fuck me raw." She giggled, arching a ginger eyebrow at me. "I've always wanted to suck on Jenn's tits. Not that I don't like the rest of you, Jenn, but those boobs drive me crazy."

"You're not the only one." Jenn said, rolling her eyes.

"Savannah, you're so innocent, I've thought about sitting on your face, just to teach you. I'm not into girls, really. Well, a little bit. Sophie..." She trailed off. Sophie had a wicked grin of her own now. "We'll talk about that later. Candace, I've thought about you tying me up in the back office and fucking me with a bottle from the bar. I'm serious. Maybe even sticking a beer bottle in my asshole if I'm really bad."

There was a collective silence from the group as everyone took that in. We knew Amber was dirty, but this put everything on another level. I leaned back, hoping my throbbing erection would at least distract everyone. Candace got up and went to the bar, and we all had two or three more drinks before continuing.

The next person to fall victim was Jenn again. She grumbled but chose truth, knowing how Amber's imagination stretched. Jenn took off her pants, revealing a small, tanned ass in a pink thong, stocky legs and just the slightest bit of pudge about her middle. As Jenn sat back down, her hand landed on my thigh and lingered there.

"Where's the weirdest place you've had sex?" Amber asked, sipping at her cocktail.

"Here." Jenn blushed. "In one of the rooms upstairs. Don't get upset, Candace, two of- one of the guests invited me up to their room."

"Two?" I said, shocked by the details of her tryst. I knew she wasn't inexperienced, but I had to hear this story. Jenn went on.

"Two navy guys on leave. One black, one white. They... what do you call that? Spit roasted me? I took the black guy in my mouth but he came in like thirty seconds. I can't believe I'm telling you guys all this." She said, blushing. "The other guy, Jason, he was really sweet. I dated him for like three months, until he wanted to meet my parents. How would I explain the way we met?" She laughed, shaking her head.

"Was he as big as they say?" Savannah asked, wide-eyed. "Some of the girls in my unit say it's a myth."

"Tiny!" Jenn shouted, holding back her laughter. "Jason was like five, maybe six, average, the black guy was maybe three inches hard as a rock. Kind of a disappointment, really." She spun the bottle around. It landed on Savannah who, to my surprise, chose truth. Carefully, cautiously, she slid a pair of white cotton underwear down her dress and threw it off to the side, making sure to cross her legs as she sat back down on the carpet.

"Are you a virgin?" Jenn asked, already suspecting the answer.

"Well, yeah." Savannah admitted. "I've given a guy a blowjob before, when I was at infantry training. His thing wasn't even hard. It turned out he was gay and just wanted to see what would happen." She shook her head, obviously embarrassed. "We made out a few times and he tried to finger me in his car, but that was about it."

"To new experiences!" Amber interjected, holding her cocktail up and draining it. We all followed suit. Savannah spun the bottle before it came to rest on Candace. The manger mumbled "truth" before standing up and taking over her pants, revealing long legs leading up to a muscular, round ass covered by lacy black underwear. An anchor tattoo was just visible on one of her cheeks.

"Answer Jenn's question from before. What were thinking about, this morning, when... you know And who were you thinking about." Savannah said, not making eye contact with the lioness of a woman before her. Candace intimated all of us but terrified Savannah. We were surprised she was playing at all.

"I was thinking about... Oh Jesus, I can't believe I'm going tell you all this." Candace said, shaking her head. "I was thinking about this one time with D."

"You slept with D!?" Sophie exclaimed, suddenly. D was a line cook at the restaurant, a guy whose ethnic origins were as much of a mystery as where he slept at night. He worked hard, said little, clocked in and out on time was visibly the soberest of all the cooks. We called him "D" on account of his resemblance to a popular actor.

"Not slept with, no. I was closing the bar one night when Rosie called out." She shook her head at me. Leave it to Candace to use a sex story as an opportunity to correct an employee. "There was no one in the place and I went out back to see how close he was to being finished. The kitchen was finished, but D was standing there, dick in his hand, jerking away right in the middle of the place. I was... stunned." She took another sip of her drink. "I'd been flirting with him all night, now that I think about it. Said I wouldn't mind if a good-looking guy pulled one of those jokes from that awful movie Waiting on me."

"What did you do?" I asked, incredulous.

"I got down on my knees in front of him, pulled the girls out and waited for him to finish." She said, as casual as could be. "I licked it off as best I could, he cleaned the floor again and we went our separate ways. Haven't talked about it since." She laughed. She spun the bottle as a way of announcing that question and answer time about her tryst was over. It landed on Savannah, who groaned.

"Dare." She answered, instinctively.

"Hmm..." Candace said, contemplating the girl's fate. "I think I've got an idea. Rosie, write down on a piece of paper how big your cock is. Don't give me that look, just do it. Write in half-inch increments. Keep it secret from everyone else." I shrugged and wrote down "7.5", which was the honest answer. Candace continued. "Savannah, we're going to play 'Princess and the Pea...nis. You're nineteen, I know, but I'm sure you'll remember the gist of it. Sit down on Rosie's lap for three turns. After the three turns, guess how big his cock is, hard. If you're within an inch, Rosie must do any dare you say, completely naked. If you're wrong," She gave another malicious grin, "You have to give Rosie a blowjob and swallow every drop of his cum, right in front of us. Once he gets that thing out, anyway."

"This is getting way too completed." Protested Sophie, waving her hand. "Savannah, you don't have to do this. I think this is getting out of hand."

Another stunned silence fell over the group. I half expected Savannah to rush from the room, crying. She instead stood up, her legs shaking and plopped herself down right on my lap, rubbing her round ass into my crotch. I could feel the cheeks of her ass gripping around it, now that she didn't have any panties on.

"Just tell me how big it is and I'll give you one anyway, maybe." Savannah whispered in my ear. Her breath smelled like mint and gin. "If you teach me how."

"I'll take my chances." I winked at her. She spun the bottle from my lap. It landed on Sophie for the first time. Sophie cursed and took over her sheer top, revealing a small, perky pair of breasts crowned with dark, pointed nipples. Sophie hadn't bothered to wear a bra. Her tits were the first exposed in the game and we all cheered, Amber going so far as to tweak one of her nipples. Sophie covered them with her hands. "Truth, obviously." Said the lanky half-Chinese girl.

"Have you and Amber fooled around before?" Savannah asked, pointedly. Sophie shrugged her narrow shoulders, looking at Amber for the go-ahead.

"When we were drunk." Sophie admitted. "A little, anyway. She got me off with her fingers, once." Sophie shuddered with pleasure at the memory before turning to her friend. "You tried to get me to eat you out that one time."

"I did not!" Amber exclaimed before the realization struck her. "Well, okay, maybe I did, but I was so horny. I can be held liable for my actions."

"Aren't you all the time?" I asked, smirking at her. Amber gave me a knowing smile. Sophie spun the bottle around before it landed on me and Savannah.

"I guess that counts as me." I offered, pretending the part of the gentleman. "Truth." I said, unbuttoning my shirt and throwing it off to the side. I was down to only two pairs of clothing, but I wasn't in the worst shape. Savannah had three still on, her socks, bra and dress, Jenn was in her underwear, Amber was only lacking her shirt and Candace was down to a shirt and underwear. I wasn't sure if Sophie had any panties on under her jeans.

"If you could fool around with each one of us, what would you do?" Sophie asked, all nerdy coquettishness. I loved her look, her dark hair set above a pair of black framed glasses and her pouty lips. "Go person to person."

"Well, my fantasy with Savannah is about to come true in another turn." I winked at the girl on my lap and gave her prodigious ass a good squeeze. "I'd tit-fuck Jenn, obviously."

"Men." Jenn said, playfully rolling her eyes.

"Amber... I'd let Amber take control. Show me something I haven't seen before. Let her blow my mind."