Tip Your Bartender

Part 1: Straight?

Back in college, when I was 21 in 2002, I worked for a private event company that catered to the affluent neighborhoods of NYC and Long Island. I alternated between checking the guest list at the door, a barback and security type thing, and occasionally bartending. I wasn't a great bartender, but I was a people person so for the more intimate parties I usually drew the bartender card for that reason. So that 4th of July weekend it was a relatively small gathering of less than 40 people at a waterfront house in the Hamptons and the gig landed on my lap.

I had worked at this house for a bigger party during the holidays, but worked the guest list at the front door. All I knew about the host was that she was someone important in the fashion industry, but had yet to actually meet her. My boss refreshed me on the house rules which included which bathroom the staff used, where the extra inventory was, and which parts of the home were off limits to the staff. My boss then pointed out an athletically built redhead with porcelain skin in her mid 40s in a red sundress and told me that was our host, Rebecca, and to do whatever she says. He then went on to his next station and left me to finish setting up the bar.

The bar was set up on the deck of what I assumed was the pool house since it overlooked the pool more than the bay. That pool house was basically our office for the night. It's where we had the inventory, staff bathroom, and a makeshift locker room for our personal items if we had anything. The main house was off limits to a lowly bartender such as me.

The party was about to start as I set up the final touches at the bar and ducked back into the pool house to square up my outfit for the night, black dress shoes, black dress pants, and a black polo shirt with red accents on the collar. I had played baseball throughout High School and stood 6'3" 220 lbs with my dark brown hair most closely resembling the haircut of a military man, clean shaven, fairly muscular with a small belly, and thanks to my Italian and Norwegian heritage wasn't quite a bear, but definitely not smooth. No one was going to mistake me as one of the guests, but I wanted to look professional while also filling out the shirt well, I at least thought that helped with tips. I made my way back to the bar and the redheaded host appeared to be making one final lap of the party to make sure everything was up to her standards. As she approached the bar I embarrassingly said "Hello Miss Rebecca, would you like anything to drink to start off your night?" She stopped, took a look at me, seeing that I had a slight blush of embarrassment for how I just spoke to her and, breaking my awkwardness said "That's a great idea, I'll have a vodka and club. There's also no need to be so formal, Becca is fine." I made her drink, she smiled when she took it, and went on her way.

The guests started making their way in, all wearing their most fashionable and expensive summer clothes. I'd try and describe them better, but I know nothing of actual fashion. The guests all appeared to be between 30-50 years old with a mix of men and women all enjoying themselves. As the night went on and the drinks flowed the guests became more flirty, both the women and the men.

I'd been in the bar and entertainment industry for long enough just to take a compliment from whomever gave it no matter how inappropriate or not my type they were. This had led to a few one night stands with some slightly older women and even a threesome with two female realtors after their company's Christmas party. I was mediocre at best. Saying I went with the flow when it came to these rich women using me for their pleasure was an understatement. As for the men, at this point I had allowed some playful ass grabs and even crotch grabs if they were good tippers, but never anything beyond that. They just weren't my thing, at least that's what I thought.

The party continued, some fireworks were launched over the bay, and our hostess Becca made her way to the bar with a small, probably 5'2" Latino man in his 30s. He was very petite, feminine, and loud. He exclaimed "Bartender, 4 shots of tequila!" I grabbed the bottle of expensive tequila, lined up 4 shot glasses, filled them up, and as I was leaving them to their shots he said "Where are you going? You cannot leave us like that. You need to do shots with us. It's America's birthday!" I informed him that there was a no drinking policy while I worked. Becca pointed out "well I'm paying you, so you're doing a shot with us." I wasn't going to argue that logic, so I did a round of shots with the two of them. Then simple math kicked in and I inquired who the fourth one was for. Becca looked at me, changing to a serious demeanor and said "This one is for Miss Rebecca!" She took the shot, slammed the glass on the bar, and then laughed playfully as her and her petite friend went back to the party. I'd say that was odd, but  some drinks are crazy and I just took it has her fucking with me about earlier in the night.

The night was winding down, many of the guests had already left since it was close to midnight, and my boss was politely letting everyone know it was last call. The petite Latino man came back with two of the other male guests, one in his early 30s, about my height, slender build, tanned white skin with shoulder length blonde wavy hair, clean shaven and the other in his late 40s, about 5'8", average build with a shaved head, brown goatee, and appeared to be missing his pants. "Another round of 4 shots of tequila Mr. Bartender with the tight sleeves and bubble butt!" The petite Latino man exclaimed. I turned to grab the glasses and the bottle and overheard the blonde surfer looking one say "You were right about that ass and he's got some nice DSLs too." I had no idea what that meant. "Bubble butt" and "DSLs" were something I would have to look up on Urban Dictionary later on. The petite Latino man motioned for me to take the fourth shot, which I did. He slipped me a hundred dollar bill, thanked me for the drinks, and asked me my name in case he wanted to request me to bartend one of his events in NYC. "I'm Frankie" I said, just now realizing I never mentioned to him or you, the reader, my name. "Nice to meet you, Frankie. I'm Victor, hope to see you again soon." Victor, surfer man, and their pantless friend walked off towards the main house.

As my boss and I finished cleaning up the bar area, the hostess, Becca, came over to pay the rest of her bill to my boss and pulled him aside to talk to him. While they were up front chatting, I brought the garbage to where it needed to go and stopped quickly to organize the tips I had shoved in my pockets throughout the night. At a quick glance it was over $2,000.00 of cash, a couple scraps of paper with email addresses and phone numbers, and one business card with a man's name crossed out on the front and his Russian trophy wife's phone number written on the back. I wasn't sure if she was serious or not, but she filled out that card right in front of her husband saying she wanted "a real man" to take care of her. Sounded hot, but I definitely didn't want to get involved with whatever was going on there. Maybe I'd try one of those other numbers or head to the bar with the other staff and see what the Hamptons nightlife brought me.

As I made my way back to the front of the pool house my boss came up to me and informed me that Becca had asked if I could stay and bartend the after party inside the house and she would of course pay me more for staying late. He told her it was up to me and here he was asking. I thought about how much I had already made that night and how well they were tipping and I agreed to stay. He said goodbye and Becca motioned me to follow and off to the house we went.

Before we went in Becca handed me $500.00 and said that should take care of the rest of the night. I thanked her as she led me through the back entryway walking down a flight of stairs to the bottom floor of the house. We walked down the hallway, me now noticing her nice yoga trained ass peaking out a bit from her dress, and got to the end and before we went in she turned to me and slyly said "Remember, you have to do whatever Miss Rebecca wants" as she led me into the after party.

I walked into a room about half the length of a basketball court. There was already a DJ playing house music complete with colored rotating lights, strobes, and a fog machine. She really knows how to do this rich thing well I thought to myself as I started making my way to the bar across from the DJ. The alcohol had been flowing all night and I'm sure some other party favors as well so everyone was already feeling good. They were also very handsy. My ass and crotch were groped a few times as I made my way to my work station. I did a quick look around the room and saw Victor was there a long with the surfer dude, the pantless guy was still pantless and dancing with a couple of skinny women in tight skirts, and even the angry Russian trophy wife was flirting with someone not her husband at the end of the bar and noticeably was down to just her bra and panties. Becca was over chatting with the DJ who had long brown hair, an American flag low cut v neck shirt, and a tight sparkly red mini skirt on.

Becca and the DJ made there way over and I could see Becca mouth "tequila" to me and I turned to search for the bottle and some glasses. I put the glasses down poured the shots and couldn't help but noticed the DJ had turned around to talk to someone and that her ass and legs looked amazing in that sparkly red mini skirt and matching heels. Becca introduced me to the DJ, Chanel, and I realized quickly that the hot DJ was in fact a crossdresser. Ok, I thought, this party is interesting and I can admit this DJ still has a great body. Victor and the surfer dude came over to get some drinks and I overheard Chanel say "He's a little younger than I was expecting, but you boys are right about those DSLs and butt". I still had no clue what they were talking about.

At this point it was around 2 AM, Chanel had switched to 80s freestyle, and I was 6 or 7 shots of tequila and a couple of beers in. I was feeling a nice buzz at this point. This was the part of the night where things started to get interesting. I'm not sure if it was because I was the fresh young guy there or just new in general, but there seemed to be a game at foot and I was the target. The Russian trophy wife still just in her bra and panties started dancing like a stripper a few feet in front of the bar using one of the random stools as a prop and I was enjoying the show when I hear a familiar voice say "Yeah, she's hot, but my ass looks better in panties and I suck a better cock" as I turn to see Victor who snuck behind the bar to let me know that and get a nice handful of my crotch. I slid away slowly and he grabbed himself a beer, winked, and walked away. I was getting hard in my pants and at this moment I wasn't sure if it was from the Russian dancing or my package getting some attention.

Becca comes over and motions me to follow her. I do and we go back into the hallway and she apologized for Victor's actions and the odd turn the party has taken. She says she understands if I want to leave and there's no hard feelings if I do. I say "No, no I'm good still. I'll stay. It's not what I'm used to, but I'm fine." "Miss Rebecca approves" she says jokingly and I go back into the party.

At some point someone grabbed a bottle of orange flavored vodka and body shots off the Russian trophy wife became a thing. It didn't take much to convince me to join in. And then it was Victor's turn. At some point he also changed into bra and panties and hopped up on the bar. It took a little more convincing but I hear "Miss Rebecca says to do the body shot" and I did. Victor then jumped up on the bar showing that his ass did indeed look great in panties, turned around and leapt onto me wrapping his legs around me before giving me a quick kiss on the lips and prancing away. I can feel my pants get tighter and just think, okay, this is a new feeling. Things started moving quickly from there. Tequila will do that.

Becca now gets in on the action from behind me, wraps her arms around my waist, and proceeds to stick her hand down my pants and grabs a firm hold of my now rock hard cock and says "Miss Rebecca needs you to come with her". Wow, am I ever glad that I called her that before. I follow her like a willing dog down the hallway and up some stairs to a section of the house I hadn't been to yet. We stopped in what appeared to be a living room with a couple of couches and TV in it. She says "Before this continues I want you to know that if you get uncomfortable at all we can stop. We'll stop right there and that's the end of it." I nod my head in agreement, a little confused because I still have no idea what's going on other than I'm beyond horny at this point. She goes "good, now strip". I hesitate and she repeats herself "strip and put your clothes on that chair". This time I understand the assignment and do as I'm told. She instructs me to stand there and reiterates that if I get uncomfortable we can stop. She sits, stays fully clothed, and says "you can come in now" as Victor and the surfer dude walk in. Victor has now added a blonde wig and heels to the lingerie he was wearing and his blonde friend was wearing only panties. Becca looks at me to see if I'm going to bail or not and I give her no indication that I'm leaving. I'm extremely nervous and everyone in the room can tell. Blonde surfer guy rubs my shoulders from behind telling me to relax as he lightly rubs his bulge against my ass. Victor walks over to Becca and asks her something that I'm too distracted to hear and she tells Victor that's a great idea. Becca gets up, motions for all of us to follow her and we enter another room that looks like a study.

She has me sit down on one of those couches you see at a therapist's office. I see Victor going through a drawer looking for something and Becca tells Sarah, apparently her nickname for the surfer guy, to check a different drawer. He pulls out a dildo and she says "a little early for that". Victor then pulls something out and Becca says "perfect". "This will help you relax a bit" she says as she blindfolds me. Victor lays me down on my back as Becca slips my hands into some restraints that were already on the couch. Becca squeezes my hard cock and told me to play nice with my new friends. She removed her hand and a mouth, I was assuming, Victor's, took my cock right down. After some squirming I relaxed a bit and my suspiciouns were correct about that being Victor's skilled mouth after he said "I told you I'm better than sucking a cock than some woman" and proceeded to get back to work on my shaft while playing with my balls.

"Good boy" I hear Becca say. "Sarah, why don't you give Victor a break and help out."

Sarah took over sucking me and was a bit more aggressive and started jerking my shaft as he sucked me. Everytime I felt like I was going to cum he eased off like a pro. Sarah began working on my nipples, pinching them as he sucked. I squirmed some more from the sensation. Sarah teased my ass a bit with his finger, but I wasn't welcoming that just yet. Sarah got up and Victor, now without panties on straddled my face and teased my mouth first with his fingers, sliding them in and out and then teasing my lips with his hard cock before I relented and took his hard cock down my throat. Slowly at first and then he started to fuck my face hard and fast. He ripped the blindfold off me, flipped around so he can suck me and I took his cock into my mouth as we started to 69 with him on top.

Out of the corner of my eye I could see Becca get up, say "you boys don't have too much fun", and head out the door. Victor got up off me and Sarah now leaning over the edge of the couch started to suck me again, this time with me being able to see his skills. Victor came up behind Sarah, worked his panties down, and lubed up before slowly entering him with his hard cock. Sarah paused at first and once Victor got a good rhythm going went back to sucking my hard cock. 

This went on for a few minutes while I was still restrained. Victor pulls out and tells Sarah that I'm going to get all the cum. Victor comes to the side of the couch as Sarah jerks on the other side of me and sticks his cock in my mouth, fucking my face until I feel his hot load hit the back of my throat, swallowing it down as my first reaction. This pleased Victor and he tells me it's Sarah's turn. Sarah was already close to exploding from jerking it and barely got his cock into my mouth before shooting his load down my throat. Victor then said it was my turn. Sarah held my legs up over me as Victor jerked my cock pointing it right at my own face. I shot all over myself and Victor told me lick it all up and I did. They undid me, cleaned me off, and said next time they're going for my ass. I got dressed, made my way back to the now empty party room and found three Polaroid pictures behind the bar. One of me tied and blindfolded and Victor sucking me off, one of Victor straddling and fucking my face and had Victor's phone number, and one before shot of me sitting blindfolded and naked on the couch. That one was signed "Thanks for listening, Miss Rebecca". 

"Looks like everyone had fun without me" a voice said from behind me. I turned and saw it was DJ Chanel. "Looks like they didn't leave much for me, but I'll have to claim that ass of yours another night" Chanel said with confidence as she gave me her business card and told me to call her sooner rather than later. I nervously nodded and headed out to find my car. I got in and saw I had a message from my boss asking me how it went. I'll respond when I wake up I thought and he'll get the safe for work version. 

Part 2 of the Top, I mean,Tip Your Bartender coming soon