Tip Your Bartender

Part 2: Bottoms Up

A few weeks had passed since that 4th of July weekend party at Rebecca's house in the Hamptons and I still wasn't sure how I felt about the whole thing. Did I get caught up in the moment? Did I fall under the spell of a powerful redhead? Or did I have gay attractions that got brought to the forefront that night thanks to tequila and horniness? No, I thought to myself, everything got out of hand real quick and I thought I was going to get some action from Miss Rebecca. I'll put that in the rear view mirror and move on. Like any straight man who was questioning his sexuality I did the only thing I could do, hook up with a girl and suppress the feelings from that 4th of July party. I did just that and for a couple weeks, until around the middle of August, I was content with my hetero life once again. Then came a bartending request from my boss.

My boss, an older Greek man in his mid 50s named Gus, was around 5'7" and had a heavyset build with greying thinning hair, and while he was good at running a business and booking gigs, he lacked a certain awareness of things going on around him.

"Rebecca was really pleased and impressed at how you handled yourself at the party. She said you exceeded all expectations at the after party as well." Bossman Gus said to me not knowing all of the hidden meaning in her praise. It also made me a little uneasy and nervous thinking he may find out what happened.

"You must have had a good night because I got a request for you to do a party next Saturday. A guy named Trevor, do you remember him at all?"

I told my boss I did not, but I joked that I was sure I must have poured him a few shots to his liking then. Gus went over the details, it was going to be at one of those recently reclaimed industrial buildings turned apartment lofts in Long Island City, and indeed would be the bartender that night. Only my second time bartending since 4th of July (the other parties we did had chosen my female co-workers with much nicer breasts than mine for some reason leaving me to other duties). The last party I bartended was for one of those local business associations and was very uneventful other than a local politician getting a drink thrown in his face.

Saturday comes and my boss, a few coworkers, and myself are setting up. I'm nervously scanning the room for any one from the July 4th party, but don't see anyone. The DJ is a short chubby Italian man in his 40s, definitely not DJ Chanel. I started to feel more relaxed now that I hadn't seen any of the other players from my extra curricular activities. Then I met Trevor.

Trevor. I remember Trevor. He was the random pantless guy from Rebecca's party. He didn't seem to have much interaction with my friends from last time, so I was once again feeling a bit relaxed. 

For the first hour or so of the party it was a pretty standard one. Mostly a beer and wine crowd with a few hard liquor drinkers and some shot takers mixed in. The DJ was pretty terrible playing what he probably heard on the Top 40 radio station this week in no particular order. No sexual advances or overly flirty party goers at all. A tall thin man then walks up to the bar and orders a gin and tonic. It's surfer Sarah.

I hand Sarah his drink and he looks at me realizing I've become a bit nervous and says to me "Hey, how have you been? Having a good night? I'm Scott, we met at that 4th of July party."

"I'm doing alright, thanks. Hope you're enjoying your night so far" I reply nervously, hoping he doesn't say anything more about that night with my boss in earshot. 

"So far so good." He says while he slips a $20 bill onto the bar as a tip, smiles, and walks back into the party.

I breathe a sigh of relief appreciating that he didn't blow up my spot and for the tip he left. I feel some anxiety as I look around the room for any Victor, Chanel, or even Rebecca sightings. I see none of them and don't even see Sarah/Scott anymore. However, now that I've seen Scott/Sarah, in the back of my mind I am slightly disappointed by how uneventful the party has gone. 

Another hour goes by and the alcohol and other party favors are kicking in for the guests. Some of the guests have turned their attention to the DJ, requesting and demanding he play some drunk sing-along songs from the 70s, 80s, and 90s. Looks like he begrudgingly accepts their intoxicated harassment and starts playing songs that the crowd starts to enjoy. Some of the party goers have now realized shots are a thing and I'm busy pouring out trendy shots I don't even notice an androgynous looking mixed race (possibly African and Asian background) person in a blue and white pant suit with matching blue heels walk up a few people down from my left. I finish pouring the shots and hear "you never called".

I look over and it takes me a few moments before I realize who it is, DJ Chanel. She winks at me, orders a red wine, and walks away in a slow and sultry manner, making sure she had my attention. 

About a half hour later, Chanel comes back to the bar with Sarah/Scott and a  couple in their 40s who I don't recognize. Chanel herself I'm just noticing is in their mid to late 30s with Asian and feminine features, but a darker skin tone and without the 5 inch heels stands at about 5'9". I take drink orders from the four of them, get them their beverages, and they start back towards the party. Chanel stops, turns around, heads back to the bar, and orders a flavored vodka shot. I pour her the shot, she takes the shot, pats her pockets like she is looking for something and tells me she can't find her phone and asks to borrow mine. I think about it for a second, pull it out of my pocket, and hand it to her. She flips it open (it's 2002), dials a number, lets it a ring a few, closes the phone, and hands it back to me. Chanel tells me there was no answer, gives me a look over with a devilish grin, and walks away. I'm not sure what just happened, but I'm starting to feel turned on. Sober this time, but still getting a little hard in the pants. 

The rest of the party runs it's course, we clean up, and head out. As I walk the few blocks to where my car is parked I check my phone and see I have a text message that read "Hi, it's Chanel. Some of us are going out. Call me if you're interested".

I walk another block to my car, take a seat, see that it's around midnight, and contemplate my next move. Curiosity got the best of me and I call Chanel. She answers the phone and playfully mocks me for finally calling. She tells me where they are and I walk 10-12 blocks to an old Irish pub. 

Inside it's a dimly lit dive bar. Not exactly where I was expecting. Chanel sees me walk in and waves me over to a corner booth where she's sitting with Scott/Sarah and the couple from before. She gets up to greet me, can tell I'm feeling a bit nervous, and points me to a point of beer and shot waiting for me. I slide into the booth next to Scott/Sarah, and Chanel slides in next to me, squeezing my leg quickly hinting at me to relax. She introduced me the couple, the man, Tim, was average build, probably Irish, and had red somewhat curly short hair. The woman, Michelle, was Hispanic, with shoulder length straight dark hair, and my first impression was that she was way too hot for Tim. Chanel then went to introduce Sarah/Scott and said "Oh, right, I believe you two have already tasted, I'm sorry, met each other".

Everyone at the table had a good laugh except me. They all knew how that last party went. Sarah/Scott realized I was a bit shocked by everything and slid me my shot and kindly offered his as well. I took them both down, Irish whiskey. Michelle, to make me feel better, apologized if they weren't supposed to know that, but not to worry, we're all a little gay here. 

Over the next hour I had a couple more beers and another shot to relax and Tim ordered some nachos for the table. Michelle and Tim finished their drinks, said their goodbyes, and headed out. 

Sarah/Scott was starting to try and start some under the table action by rubbing my cock above my pants, but Chanel reached under, pushed his hand away, and, while giving him an evil eye, gave my balls a nice firm squeeze over the pants. Sarah/Scott took the hint and went to chat someone up at the bar. 

"Just the two of us now, sweetie. Any thoughts?" She said.

I didn't know what to say. I just sat there awkwardly and nervously with a semi-erect cock.

"Hmm, alright. I'll ask some questions, throw out some ideas then" she said.

"How did you like Becca's after party? She's knows how to throw a unique party, doesn't she?" Inquired Chanel.

"It was an experience I wasn't expecting" I replied, getting aroused just thinking back to everything that night.

"Was that your first time using those DSLs?" She asked grinning.

"This is a dumb question, but what does DSL mean?" I asked since I never looked it up. 

"Dick Sucking Lips. Haha, you have to agree, that's what you have going on right there." She said, playfully teasing my lips with her manicured finger.

"Oh, I didn't know that was a thing, but yes, that was my first time doing any of that."  I said, still a bit nervous, but since the bar was mostly empty I was a little more willing to talk in the open about it. Chanel was not going to be subtle about it all.

"Honey, you're saying you sucked your first cock, sorry, cocks because you thought Becca was going to fuck you? You're too funny" she said loudly, playfully mocking me.

"I, um, I guess that's right" I embarrassingly answered.

"Well she still might fuck you. She just likes to toy with her prey before she goes in for the kill. Now for the real story, did you like it?" She said with intent, looking deeply into my eyes and grabbing at my hard cock over my pants. 

"I enjoyed myself" I couldn't have been more nervous saying that out loud.

"Well I'm still mad that I wasn't invited. Leaving me to get my own drinks while  you went and gave away your cock sucking virginity to those two. I should bend you over right here and give you a real cock, but I also like to toy with my prey a bit first." She gave my balls a quick slap, got up to go the bar, and left me there rock hard and stunned. 

I saw Chanel say something to Sarah/Scott and he came over to me, said his goodbye with a quick awkward hug, and wished me luck. I wasn't really sure what he meant by that last part. I was still trying to clear my head a bit so my hard-on would go down a bit so I could get up and get another drink without it being so obvious. Chanel toasted me from the bar with a devilish grin. That didn't help clear my head. 

After thinking about baseball and taxes for a bit I was able to make things a bit more manageable. I decided a quick trip to the bathroom before getting my next drink made sense. 

I entered the men's room, starting from the right there was a sink and a urinal and opposite of the urinal was a stall. I decided to use the stall just in case I needed to blatantly adjust myself. I start using the toilet and quickly find out the latch on the door doesn't exactly work. Chanel had swiftly pulled the door open, grabbed my from behind as I finished, and told me this was hers now while she undid my belt, pulled it off me, slid my pants down revealing my ass, proceeded to slap it with my own belt and told me that ass was hers too. She walked out, belt in hand, and left me to put myself back together. 

I pulled my pants back up, zipped, and washed my hands. Chanel was having a laugh with the bartender as she asked for another drink by slapping the bar with my belt. I ordered myself a drink and paid for the round. As I collected my change, Chanel whipped my ass hard with the belt. Laughing has she went back towards the table to collect her stuff. 

She told me I better finish my drink quick if I want my belt back before she leaves. I down the beer quickly, she shoved the belt into my chest, and told me to walk her home, the streets weren't safe to walk alone at night. 

We started walking back in the same direction of where my car was and after walking 3 blocks she ducked into a nearby store front, pulled out her cock, and told me to get on my knees and suck her right there. I didn't know what to do. She pulled me close and shoved me down until I got on my knees. She had a rock hard 9 inch cock that was also thick. She smacked me across the face a few times with it, shoved it against my lips, and pulled me back up, laughing. She walked away and motioned for me to follow. Her apartment building was just half a block away. 

We got to her apartment building and got into the elevator where she pushed me up against the wall and kissed me. At first I hesitated, after I've already done things like sucking cock this was different, more intimate. I didn't put up much resistance and we were in some deep French kissing while she rubbed my cock aggressively until the door open at the 6th floor and we made our way into the apartment.

We got in and pushed me down onto the couch, straddled me, and making out some more. Chanel got up, told me to stay right where I was, and she just needed to freshen up. I sat there buzzed and nervously horny not exactly knowing what I got myself into tonight. I could just get of here I thought to myself, still thinking like a confused not-so-straight man. And almost like they sensed my thought process, Chanel popped her head out the door of the bedroom and motioned for me to come in. So I did.

Chanel had changed into a set of lacy purple lingerie complete with matching stockings and heels. She wasn't wearing a wig, but her sporting that outfit with her natural short dark hair made her look even hotter. She removed my shirt, gave me another sensual kiss, and motioned for me to sit next to her on the bed. 

"Have you ever been fucked before or had a dildo used in your ass?" She asked. 

"No, never." I answered awkwardly and still thinking about backing out of this.

"Well, why don't you lose the rest of those clothes and we'll change that" she said reaching into the nightstand and pulling out a bottle of lube and a butt plug. Which was the first time I'd seen a butt plug. 

I stood up, disrobed, and Chanel I was fully hard. She told me she was glad to see me so excited and teased my cock with a quick lick of the tip. She stood up, spun me around, smacked my ass, and told me it was time to loosed me up. 

"This will feel a little weird, but just relax. I know how to loosen up a tight hole. Now bend over onto the bed" she said confidently and commanding. 

I bent over, feeling very unsure of myself as I felt the first of the lube being rubbed onto my hole by her finger. She had a bit of a fingernail so it felt a little scratchy. She told me to take a deep breath and exhale. Just wanting me to relax as she slowly worked her first finger into my tight ass. I let out a soft moan and she assured me I was doing good. She switched to what I assumed was her thumb and pushed me open a little more. Chanel then bent over next to me, grabbed my head, and turned my face to hers and gave me a deep kiss. 

"You're being a real good boy so far. I think we can do a bit more" she said as she stood up, pushed my head into the bed, stood behind me and rubbed her panties covered cock against against my ass as I heard the bottle of lube open again. 

Chanel told me relax again as she lubed up my hole more and slowly pushed the butt plug into me I'm. I grimaced in pain a bit, trying to hide it, but she reassuringly said it was just about in. She got the butt plug in place and told me that she'd make a slut out of me before the night was done.

"Good slut, now come here and get on your knees." She commanded and I obeyed.

Chanel pulled her panties aside and put her thick hard 9 inches in front of my face and told me to suck it. I wrapped my lips and slowly attempted to take her all the way down. I gagged a bit, pulled off, and she laughed.

"A little more than you've had before, you'll get it down with some more practice" she said while grabbing the top of my hair and guiding my mouth back to her cock. 

I took it down as much as I could, remembering what I liked when girls gave me head. I licked her shaft, kissed her balls, and traced my tongue around her tip. That must've been the right move because she grabbed the back of my head and started fucking my face hard and fast, leaving me gasping for air. Getting my face fucked while having a butt plug in me was just making the whole experience even hotter. She told me to get up as she removed the panties and laid back on the bed with her legs spread, motioning with her finger for me to crawl between them and go back to blowing her. 

I kneeled on the bed in front of her and went back to work on her hard thick cock, feeling better about my ability. She smacked my face and told me to look into her eyes as I pleased her. I followed her order, got slapped again, and she put both hands on top of my head and pushed down til I gagged. We did that a few more times and after I sucked some more, Chanel decided it was time to loosen me up some more.

Chanel directed me to bend over onto the bed again and pulled the butt plug out. That was a strange, but erotic feeling I thought. I went to stand up and she told me to stay where I was and not to peek. She lubed me up again and this time I felt some bigger and being pushed against my ass. She told me to relax and kept slowly entering me with whatever was being used this time. It got in deeper than the butt plug did and had my hole stretched out more. She reached around me, grabbing my hard cock and stroked it. 

"My little slut takes a dildo well and enjoys it too." She said while now slowly but steadily fucking my ass with the dildo. I almost came right there. 

She fucked me some more with the dildo, calling me a slut and a whore, and telling me it's almost time for the real thing. She pulled out the dildo and told me to go lay face up on the bed.

I laid down and she fed me her cock immediately while straddling my face and reaching back to stroke my cock. Once she was satisfied with how hard she was she grabbed a pillow, flipped me over onto it, pushed my head down and I felt the lube on my ass again.

The head of her cock was working slowly into my ass. Chanel reminded me to relax and open my mouth wide as she officially took my anal virginity. I squeezed the bed sheets hard while moaning in a pleasurable yet painful way. She rested balls deep into me, working her cock around, loosening up the muscle for what was to come. She fucked my ass slowly a few more times, but each time pushing slightly deeper than the last. 

Chanel grabbed me by the hips, adjusting me into a bent over praying position and started fucking me harder and faster.

"Stand up and lean over the bed slut" she demanded. 

I bent over the end of the bed and started to get fucked doggy style. As Chanel fucked me I moaned and kept squeezing the sheets. She spanked my ass as she slowed up a bit, giving me a chance to recover a bit. 

"Flip over, get that hole to the edge of the bed and grab your ankles" she instructed. I didn't do it right so she shoved my legs up in the air and told me to hold them. 

She forced her cock back in quickly and rested my legs on top of her shoulders. She stared deep into my eyes letting me know who was in charge. She leaned me slightly to one side holding one leg higher than the other and somehow fucked me even deeper. After she was satisfied with owning my ass she told me to kneel in front of her again.

She shoved her cock back into my mouth as she stroked her shaft. Feeding me some more until it was time to cum.

"Open your eyes and look at me. I want to see your eyes when I cum on your face" she said stroking her cock. Within moments she sprayed all over my face, making it a bit difficult to maintain eye contact. 

Chanel sat on the bed, motioned for me to sit next to her, and while making out with me she stroked my cock vigorously. When she could feel me about to explode she pushed me back onto the bed and shot my load all over myself.

"You were a good slut. Maybe next time I'll invite a friend." Chanel teased as she tossed me a towel to wipe all the cum off of myself as best that I could.

It was almost 6 AM at this point and I guess from all the fun I put my head down for a moment and passed out. 

Around 11 AM I woke up confused to where I was, why I was naked, and why my ass and legs were so sore until my memory kicked in. It was just me in the bed and Chanel was nowhere to be found. I gathered my clothes and ran into a problem, I couldn't find my briefs. I looked around the mess we made and heard a laugh and it was Chanel, now just wearing an oversized T-shirt with a popular cartoon character on, standing in the doorway waving my grey with blue stripes briefs around. 

"I gave you your first cock fucking and I'm keeping these to remember the occasion. You're welcome to wash up in the shower though. I promise not to interrupt your bathroom time again" Chanel said jokingly.

I took her up on the offer and took the shower, half hoping Chanel would join. I washed up, put all my clothes minus the briefs on and prepared to leave. 

Chanel came over and gave me a kiss and a tight hug and hoping I enjoyed myself. I explained the soreness, but otherwise said it was the hottest night of my life. She laughed about the soreness and said she went easy on me. She said next time she'll bring out the whole toy box. Apparently the thought of that excited me and it showed through my pants with going commando and all.

"Oh, you like that? Well don't forget to call me this time. Come here and give me a goodbye kiss" she said as I came closer.

 She squeezed my head tightly giving me a deep kiss that I didn't hesitate to accept this time.

"I know your new to this, but it's also customary to give the host a goodbye blowjob too" Chanel said laughing.

I stood there confused directly in front of her.

"I'm kidding, but it was worth it to see your innocent deer in headlights look one more time, but..." She mused while pulling up her oversized tee revealing her hard cock. 

I got down on my knees and took her hard cock into my mouth. 

"Oh, a slut and a gentleman. Good boy" she teased.

I took her cock down my throat eagerly and then she took control. Her oversized tee over my head while she face fucked me. She shot her morning load down my throat and I swallowed every last drop. She pulled me up, kissed me again, and sent me on my way.

I got back to my car and my message alert went off on my phone.

"Those DSLs didn't disappoint and neither did your ass. Call me soon slut"

My cock once again getting hard as I prepared to drive home with a sore ass and full of cum. I drove off knowing I couldn't say to myself that I was straight anymore. I wanted to experience more and hoped there were more sexual experiences coming my way.

---

Part 3 of Tip Your Bartender coming soon. Thanks for reading.