Tip Your Bartender

September came and went, I was back in college taking classes and working my handful of part time jobs to pay for them. This didn't leave me a lot of free time or fun money, so in the rare free time I had I spent it sleeping, doing laundry, and jerking off to various genres of internet porn. I was doing the odd private party gig here and there and managed to pick up a steady bartending and doorman gig at a bar closer to my college out on Long Island than my apartment. I spent many afternoons and early mornings sleeping in my car between school and work instead of driving back home. 

It was wedding season which meant while I did make some money at the private events there wasn't much action outside of the occasional after party hook up with a bridesmaid who was drunk and horny after being the only single one in the wedding party. All part of the job really. What I was really looking forward to was Halloween weekend, where my boss had us booked to do a party on the Saturday night before Halloween at Rebecca's house.

Halloween landed on a Thursday in 2002 which meant there were possibly 3 nights of partying to enjoy. On the Friday night before I would be working a costume party at my new bar, Saturday night would be bartending at Rebecca's house, and actual Halloween I'd probably end up barhopping in the city. All while sporting a fun, but functional costume, getting to admire all the slutty nurses, slutty superheroes, slutty everything pretty much, and make enough money at the parties to enjoy a night out. I may even have enough liquid courage to partake in the large gay Halloween parade in NYC and see where that leads. That was still in the future and my horny self needed to get through those two parties, especially Rebecca's.

The Friday before Halloween party at the bar was both fun and profitable. Since I was working I needed a costume that was functional, so I put on a football jersey, eye black, wrist bands, and matching head band to complete my 1980s NFL look. I would lose that jersey later that night when a Puerto Rican Velma ended up just in that jersey after we had our post party fun at her place. Thankfully I had a predetermined costume for Saturday's party at Rebecca's house.

Pirates. The whole staff dressed as Pirates. There were definitely worse and more uncomfortable ideas Rebecca could have made and I was confused about why until I showed up to set up. She had gotten a replica pirate ship to dock in the bay at her house. She really knows how to do this extravagant rich person thing real well, I thought to myself. 

I finished setting up the bar at the pool house with close to two hours before the party was starting. It went quicker than usual thanks to my familiarity with the set up. My boss went to go get dinner somewhere nearby and the other people working the party probably wouldn't arrive for about an hour still. I was feeling a little hungover so I grabbed myself a water and went into the pool house to relax a bit before everything started.

"Well if it isn't my favorite bartender. My guests had nothing but nice things to say about your, let's say, service last time. I'm pleased you were available for tonight" said our hostess, Rebecca, wearing tight blue jeans, a white tank top, black heels, and her red hair pulled up into a ponytail. Not quite dressed for Halloween yet.

"Oh, sorry, I didn't realize you were back here. I can go back up front if you'd like Miss Rebecca." I said a little shocked she was in the back room of the pool house.

"Again with the manners, I like that about you. Such a pleaser or so I've heard from my friends" she said with a grin. 

"Thank you" was all I could get out before she pushed me down onto the couch, placing her right heel into my crotch with a little bit of pressure. 

"I'm just a little upset you didn't think to invite me for your adventures. They are my friends, after all" she said giving me an icy stare. Making me both nervous and horny at the same time.

"Oh, don't worry, I'm not mad. I was young and horny when I was your age too." Rebecca said as she leaned over where I could get a good look at her cleavage, caressing my face before slapping me.

She turned around and started walking out, her ass looking amazing in that pair of jeans, when she stopped and came back.

"I almost forgot to give you your inspection. I hope you like your pirate outfit. Now stand up and let me get a good look." she said in her boss-like way.

I stood up, she glanced me up and down, and had me do a slow turn to get a full look at me.

"Pants." She said as I looked confused.

"Drop your pants." Rebecca said as she undid my belt and yanked my pants and briefs down below my knees revealing my hard cock.

"Stay right there" she said as she gave my cock a tight squeeze and pulled out her phone.

"Yes. Pool house. Thank you." she said sharply into the phone to whomever was on the other end. 

She put her phone back in her pocket, gave my cock a couple strokes and playfully slapped my balls. I was enjoying this moment and didn't even realize Sarah/Scott had made his way in. He handed Rebecca a Polaroid camera and she took a picture.

"There, now we have a nice before picture. Sarah, why don't you help our bartender friend here relax a bit before the party. He's got a long night of serving guests ahead of him." Said Rebecca as she walked out and shut the locked door behind her. At least I hoped it was locked as I stood there pantless and with a rock hard cock.

Sarah had his blonde hair in pigtails  and was already in his Britney Hit Me Baby school girl costume. He grabbed my cock, giving it a nice right underhand stroke, placed his left hand on the back of my neck and pulled me in for a deep french kiss. We made out as he stroked me and I reached under his school girl skirt to get a good hold of his hard package. This made him pull me tighter against him, kissing me deeper as he let go of my cock and reached around grabbing a firm hold of my ass. 

Sarah pushed me down onto the couch, kneeled in front of me, and started bobbing up and down on my cock with his wet mouth. I started to moan in pleasure and he covered my mouth with his hand and stuck his finger inside my mouth keeping me from ruining our privacy. He continued sucking me and as I tried to grab his pigtails he smacked my hands away not wanting me to ruin his costume. 

Sarah stood up, straddled me, grinded on my hard dick, and gave me another deep French kiss before standing up on the couch pulling my head under his school girl skirt and feeding me his rock hard cock. He held me by the hair fucking my face and stopped momentarily when someone knocked on the door. It was my boss Gus back from his dinner. Sarah kept me silent with my mouth full of his resting cock. After no response from me, my boss must have assumed I was napping as we could hear him walk away. Sarah, confident that we had privacy again, pulled his dick out of my mouth, stepped off the couch, and told me to turn around. 

I turned around, felt his hands spread my ass cheeks, and felt his tongue begin to work my hole. I let out a small moan and he told me to be quiet before going back to work with his tongue on my ass. I moaned again from the pleasurable feeling and he stopped, shoved me face first into the couch cushion, and after I felt him spit on my hole I felt his rock hard cock slowly push its way into my ass. As he worked it all the way in I let out another moan and he shoved me even harder into the couch as he slowly loosened me up. 

Sarah started pounding me harder and faster, working different angles to loosen me up. Now that I had my moaning mostly under control he grabbed me by the shoulders while fucking me from behind getting that much deeper into me. 

"I'm going to be your first load of the night" he whispered loudly to me as he pushed my face back into the couch as I sunk deeper into it with each thrust.

I felt him explode his cum inside me as he continued to pump me with every last drop. Satisfied with himself, Sarah pulled out, started stroking me off, and then started sucking until I came in his mouth. He swallowed most of it down, but when he came up for one last deep kiss I was tasting myself on his tongue.

"I guess I should go reapply my lipstick" he said laughing.

I looked down and I could see some lipstick on my cock and Sarah was nice enough to grab a nearby napkin and wipe some off my face as well. I put my pants back on, wiped off as much of the cum and spit from my pirate shirt as I could, and Sarah cautiously made his way out of the pool house without being seen. Rebecca was right, I was very relaxed now. Sore and full of cum, but relaxed.

I had cleaned myself off enough before the party started and Rebecca came over with a devilish grin and ordered herself a vodka and club soda. She was now in full costume wearing a tight police costume that showed off both her tits, ass, and the short skirt with thigh high black boots really made her legs look incredible. 

"Eyes up here or I'll have to get the handcuffs out." Officer Becca half joked as she caught me admiring her. Her red hair flowing and her eyes and their intentions hidden behind mirrored sunglasses. 

She walked away and looked back motioning for me to stop looking at her  tight ass. That's when I felt a quick slap on my own ass. I turned around quickly and there was Victor, a bottle of tequila in his non slapping hand. 

Victor was dressed up in a bright yellow bedazzled cowboy outfit complete with fringe and matching hat.  Before I realized it, he had poured two shots of tequila. We did the shots, he gave me a quick crotch grab, and he galloped off. This party was already off to an interesting cum filled night and it had only just started.

More costumed party goers continued to arrive and admire the now lit up pirate ship docked in the bay. The music changed to some pirate-like techno music and an unexpected group of dancers emerged from the ship doing a choreographed dance fight complete with cannons firing off fireworks. 

While everyone was distracted with the pirate show my boss Gus had made his way over to the bar. He asked me if I would be interested in bartending the after party as well. Same deal as last time. I pretended to think it over for a few moments and then agreed to do it. I didn't want to seem too eager, even though he probably would have just thought I was happy to get the extra money. 

After the spectacle of the pirate ship finished up, I got busy behind the bar with many party goers wanting drinks at once. I recognized the pantless man from her first party, now dressed as an astronaut and he ordered some drinks for a few friends including the Russian trophy wife in a tight latex Catwoman suit complete with what I assumed was a real whip. After getting a couple vampires, a Spider-Man, and a tomb raider there drinks the bar area mostly cleared out as they guests went back to enjoy the night. Officer Becca, Sarah Britney, and Cowboy Victor made their way over to the bar with a couple people I had yet to meet. 

"6 tequila shots." Becca said as they all made their way to the bar. 

I poured them, lined them up, and the 5 of them did their shots and Becca shot me a look so I took the sixth shot. Becca introduced me to her two friends. The first was an athletic African American woman in her early 40s with dark hair straightened to halfway down her back, around 6 feet tall in heels, slender but muscular build, large c cups, and she was dressed in a red 1960s style Star Trek dress with matching red heels. Her name was Jamie and she worked with Becca in NYC. The second newcomer was a white man in his late 30s dressed in a stereotypical Native American costume. He was around 5'7", thin and firm build, short brown straight hair hidden by a small costume head piece, and other than a brown vest with white decorations on it, his costume was pretty bare. No shirt under the vest and tight baby blue bike shorts that definitely showed off his ass and what appeared to be a nice sized package. His name was Grant and was Victor's "friend" from the gym.

Victor whispered something to Grant causing Grant to eye fuck me as he smiled. They walked away back towards the rest of the party and Becca turned back to talk to me.

"Another two tequila shots, Frankie. I'm glad you accepted my invite to the after party. I need a good bartender that can handle everything that is thrown his way. Don't worry, you won't have to wear that pirate costume all night." She said while toasting a tequila shot with me and walked back to the others. I wasn't completely sure what she meant by not being in costume all night, but I assumed it was a good thing. 

The rest of the party was pretty standard. Victor and Grant came back a few times for drinks and shots. Jamie  came back for drinks and we discussed the past baseball season and this year's basketball season. Becca must have given her some pointers because she got me to do a few shots with her. While I was wiping down some of the stray alcohol from the bar top, Jamie gave me a friendly graze of the hand before walking off with a hint of a smile. 

As the main party ended I cleaned up the bar and put everything where it needed to be. My boss split up the money to everyone and went on his way, telling me to call him if there were any issues at the after party. Apparently I was the only one of his bartenders invited back to work at an after party at Rebecca's. So he always thought it was a dud of a gig. I just told him that I guessed they liked me.

Cowboy Victor and Native American Grant came and got me and walked me into the main house. Victor gave my ass a quick squeeze as I walked down the hallway and encouraged Grant to do grab it as well. I didn't mind the attention. Officer Becca was waiting for me in the study and Victor and Grant made their leave.

"Get out of that ridiculous pirate costume" she demanded while laughing, knowing full well that the costume was her idea to begin with.

I stripped down to my briefs as she stood there almost pondering as to what her next step was. I stood there nervous, confused, and visibly horny as she smacked my hard on with her hand.

"You can't serve drinks like that either. Too distracting for everyone." She said jokingly as she tossed a small duffel bad to me.

She told me to get changed into what was in the bag. It was a bright orange prisoner costume and it was about one size too small. The shirt fit tight around my chest and arms and the pants were so tight they left nothing to the imagination. 

"Perfect. Who else is better to serve a cop than her very own prisoner." She boasted as she slapped my ass and sent me towards the party room bar. 

I set up behind the bar in the party room and recognized many of the people from the last after party. Victor and Grant were chatting with the Russian trophy wife, Sarah/Scott was dancing with a guy in a football player costume, and Becca was over with DJ Chanel behind the DJ booth. Chanel was wearing a tight form fitting devil costume. Jamie made her way over and ordered a rum and cola. 

"Mmm I was going to comment on your costume being two sizes too small, but those pants do make your ass look really good. I see why Becca picked it." Jamie said approvingly. 

I nodded in agreement as I handed her the drink. This costume was a bit snug in an uncomfortable way, but at least it was getting some compliments. Jamie walked away towards where Victor and Grant were. I looked over towards the DJ booth and Becca flashed 10 fingers and mouthed tequila to me, letting me know to get the shots ready.

Becca came over with Chanel, Victor, Grant, Sarah, Sarah's football player friend, Jamie, the Russian trophy wife, and another tall athletic blonde woman in a cheerleading outfit that I didn't recognize. Everyone did their shots and I did mine as well. Most of the group went on their way back to the dance floor, but Chanel stayed along with the Russian trophy wife.

"Hey slutty prisoner, 2 more shots for Tanya and me. Pour yourself one too." Chanel said jokingly mocking my costume.

I poured the shots and now had a name for the Russian. We did the shots and the girls walked away. Everyone was nice and loose at this point and enjoying themselves. Sarah was making out with the football player and Grant had lost his vest basically just wearing his baby blue bike shorts at this point. Victor still had his cowboy hat and top on as well as matching boots, but had taken off his pants revealing matching yellow briefs. Tanya in her Catwoman outfit had ditched her whip, but now had a riding crop that she was playfully smacking Becca and the blonde cheerleader in the ass with. Then I felt something poking me in the ass.

Chanel had made her way behind the bar and started poking me with the plastic pitchfork that went along with her devil costume. She grabbed the bottle of tequila, took a shot straight from the bottle, and handed it to me. I took my own shot out of the bottle and put it down in the bar. Chanel gave my cock and balls a nice squeeze when I turned around and gave me a playful slap to the face.

"No extra curricular fun without me again tonight, right?" She said sternly as I nodded and she made her way back to the DJ booth.

At this point of the night it was around 1 AM and everyone still standing had been drinking since 7 PM. Becca came over and told me to pour one last round of shots and drinks for everyone. 

"Ok everyone, the party room is closed, but feel free to use the rest of the property for, well, for whatever your heart desires." Becca said while I cleaned up the random glasses on the bar and Chanel turned off the music. 

"Now turn around" Becca said spinning me so my back was to her.

She slapped the handcuffs on me, clearly having some experience using them. She grabbed me by the left arm and led me to the living room area and had me sit on a couch. 

"Be on your best behavior prisoner. I'll be right back, so don't go anywhere" Becca demanded as she left the room. 

I sat there for a few minutes until Becca came back in the room with Tanya and the blonde cheerleader. Becca made herself comfortable on my lap as Tanya and the cheerleader started making out, making my cock get stiff in my already tight pants. 

"Tanya. Sherry. I think our prisoner here is enjoying this. Ladies why don't you show him a little more since he's behaved himself so well." Becca said while teasing my cock by rubbing her ass up against it ever so slightly.

Tanya pushed Sherry down onto her back on the couch, crawled up between her legs, slipped off her panties and started to eat her out. This made me even harder and Becca stood up.

"Those pants are looking real tight prisoner, why don't you enjoy the show while I get something to help with them." Becca said in a fake concerned matter as she left the room and Tanya continued to pleasure Sherry. 

Becca returned to the room with a pair of scissors and Victor and Grant in tow. 

"Why don't you boys help out our prisoner and make him more comfortable" said Becca as she handed Grant the scissors. 

Tanya and Sherry were unbothered by the ever growing crowd and continued their lesbian fun. Grant slipped the scissors into my waistband and cut down, slicing both the pants and my briefs. Victor eagerly ripped my shoes, pants, and briefs off, tossing them aside. 

"That's a good start boys and our prisoner is so well behaved I think he deserves a little more attention." Becca said while motioning towards my now fully in view hard on. 

Grant took a seat next to me and started stroking my hard cock. Victor took off his cowboy hat and put it on my head, got down on his knees, slid off Grant's bike shorts, and started sucking on his dick. I heard the familiar sound of a Polaroid camera going off, but was too distracted by the lesbian show in front of me and the hand jerking my cock to notice where the camera was. 

"Girls, why don't you give the boys some privacy and move your fun to another room. Thank you" Becca politely hinted to Tanya and Sheri as they ran off to another room.

Grant had brought me near climax a couple of times and knew exactly when to stop. He was also enjoying the head he was receiving from Victor. With my hands still handcuffed behind my back I felt Becca's hands giving me a deep shoulder rub.

"I think I need to see how much our straight bartender has learned since last party. Victor, if you please" Becca said directing the scene as Victor got off his knees and stood up on the couch, his crotch in my face.

Victor tossed the cowboy hat off my head and rubbed his still covered bulge in my face. Grant pulled off Victor's briefs as Becca slipped her fingers in my mouth, parting my lips for what was to come. Victor teased my lips with the tip of his cock while Becca held my shoulders tightly to the couch. Victor worked his cock into my mouth as I took every inch down my throat. Victor grabbed my hair and the back of my head and started to fuck my face hard and deep. This pleased Becca.

"Taking it like a pro. I see someone's been practicing" Becca said complimenting my throat's ability to get fucked.

Becca let go of my shoulders and motioned for Victor to move. She came around the couch and put me on my knees on the floor, looking up at Victor and Grant's hard cocks. Grant wasted no time grabbing me by my hair and shoving his thick cock down my throat causing me to gag a bit. He'd go all the way in, feel me gag, and hold it there for a few seconds before releasing me, allowing me to catch my breath.

Grant and Victor would take turns slapping my face with their cocks and using my throat. Me kneeling there helpless, but willing. 

"If you're a good prisoner and swallow your guests here, I'll remove your cuffs, but only if you're a good boy" Becca said sternly as she kneeled beside me and pushed my mouth deep around Victor's cock.

I mumbled in agreement as Victor pulled out his cock, started stroking it, and right before he was about to cum he stuck it back down my throat, shooting his load into me. Feeding me every bit of it. 

Grant wasn't planning on stroking himself off and went to town on my throat. His thick cock making me gag and difficult to breath as he fucked my face. I could feel Grant's cock swell up as he pumped me full of his cum. 

True to her word, Becca pushed me down on my stomach and removed the handcuffs. My arms were sore from being restrained like that. I laid there face down while I tried to recover when I felt a lubed finger enter my ass.

"Easy, relax. I'm just rewarding you for being so well behaved and loosening you up a bit" Becca whispered into my ear as she worked my ass with her fingers.

Once Becca was satisfied with her fingers loosening me up, she slid a butt plug in and slapped my ass. She stood me up, playfully rubbed my cock, and motioned for me to follow. Horny and willingly I followed her out of the room and into the hallway, wearing nothing but the butt plug. 

Becca walked me into a bedroom, gave my cock a firm tug, pushed me back against the wall, put a hand around my neck, and licked the side of my face. 

"You're a good listener and somehow an even better slut, aren't you?" Becca stated as she pushed off me and took a few steps away from me towards the king size bed in the middle of the room.

"A very willing and obedient slut too. It's almost hard to believe that you took your first cock only a few months ago. I know you were hoping for me to fuck you, but a lady doesn't fuck someone before she sees what they can handle." she said to me as I stood there naked with a rock hard cock. 

Becca stepped back towards me and pulled me close to her by tugging my cock before giving me a deep french kiss, biting my lower lip, turning me around, and shoving me onto the bed. Becca straddled me pushing and pinning my arms over my head and teasing my cock by grinding on it. She slapped my face, smiled, and stood back up. 

"I'm almost pleased with what I see. I think you just need a little more work. I also know someone who was disappointed that they didn't get invited to the last post party fun and she'd be really upset if that happened again. Come with me and let's see if we can find her." Becca said in a sexy, but stern way. 

I of course followed her knowing that she was talking about Chanel. Chanel had fucked me real good and popped my cherry that night out. I was very open to experiencing that again. Becca led me into a dark room that was dimly lit. I had never seen one before, but this appeared to be a sex dungeon.

The room had one of those large X shaped crosses I'd seen in porn, some sex toys and whips on the wall, something resembling a saddle, a swing, and in the corner was a large cushioned area that was better lit than the rest of the room with a camera on a tripod. Becca grabbed a pair of leather cuffs from the wall, had me put my hands in them, walked me to the well lit place, pushed my cuffed hands up over my head and latched them into a hook or chain that was on the wall.

"Get comfortable, I'll go see if I can find our friend" she said laughing as she smacked my cock and turned to leave the room. 

It wasn't on, but I was restrained straight across from the camera. This room was definitely set up well and I was left there long enough to get a better look at everything. I barely knew what anything was, but recognized some stuff from enjoying some porn movies in my down time. The door opened and Chanel in full devil costume walked in, shutting the door behind her.