Tuesday Floozeday - M/F | 2016

It was Tuesday. I might’ve gone to work earlier than usual that day. I might’ve just been a bit stir crazy. All I can be sure of is the day the week and the restlessness.

I went straight to my car and pulled out my phone after closing up. I called Matt half expecting that his plans for the night would simply be staying in and most likely working on his website. It didn’t ring long.

“Hey what’s up man?” I asked.

“Hey, not much.” There was a brief silence as if he had something on his mind. “You?”

“Just closed up. I can’t stay in tonight. You got any plans?”

Matt immediately responded, “Yea dude. I’m actually going to a show. I got a photo-pass and a plus one if you want to go.”

“Hell yea man. Where’s the show?”

“It’s in the Upper East Side. It’s not really like the usual shows. It’s Girl Talk. It’s pretty big.”

I didn’t know what that really meant so I asked, “What like a concert big, or like sold out big?”

“It’s a concert. It’s probably going to be sold out. You should come though. I mean you might be alone for awhile because I have to take pictures up front, but there should be a lot of talent.”

“No yea, dude. I’m definitely down. I mean, I have to go out. I’d only regret it when I’m 30.” I stated this as I always did. We always would tell each other to live life with no regrets. Our basis was that we would at some point be 30 and we should never pass up opportunities.

I was relieved to have plans for the night. The cherry was that Matt was offering to drive us straight in. All I needed to do was stock up on some booze so before I went home I stopped by a liquor store. I needed something strong, something I could feel. I chose Patron. It was more expensive than what I was usually accustomed to, but for that night it was something to look forward to.

A few hours later I’m in Matt’s car. He had his own drink ready to be mixed. I had previously poured my Patron into an empty Poland Spring bottle and had about seven shots in there. I had over done it. I was understandably wary about drinking it all. I sipped the foul smelling tequila as we drove into from Hoboken into New York.

Surprisingly we were able to find a parking spot just a few blocks away from the venue. The show had already started, but Matt didn’t need to be there for the opening bands. As a result, we stayed in his car keeping warm while drinking.

Warm tequila is tough to swallow. It’s pretty common to take it with a chaser or at the very least a lime. I always get offered limes. I’ve forever been against doing exactly that. It’s not that I dislike limes. I fucking love chewing both lemons & limes. Maybe it’s just because when I first started drinking it was so awful that chasing was just a waste of time for me. It never did its job. That may have been the original reason, but afterwards I just grew accustomed to the burn. It became part of the process. Whenever I feel that burn it feels invigorating. It makes me feel alive.

Tonight was going to be trouble. I could tell by the way I was drinking. I cringed before every sip. Eventually I decided to suck it up & started taking larger gulps. Matt was mixing his drink in the car with some diet Snapple. He never rushed drinking it since he could walk down the street inconspicuously. I tended to draw a bit of attention since I always drank my liquor neat. Eventually I got to the point that I couldn’t continue. I offered Matt about a shot and a half of what was left and he gladly took it. He chugged it, chasing immediately after. I shook my head and smirked. I didn’t quite call him a pussy.

We walked straight to the venue. It had bit of a line but it moved quickly. It gave Matt enough time to finish his drink. He had two tickets for us at will-call. He also had a special photo pass so that he could go in front of the rails and take photos for his website. It seemed pretty cool but I was content with just being there. He handed me my ticket as I followed him inside.

The venue was busy. It was a large room that had a back area with a few steps that led to an island bar. Aside from that, there was another bar near the entrance that seemed a bit makeshift and less busy than the main bar. The bands played on the stage on the opposite end of the room. Most of the crowd was in front of the stage and bunched to the left side away from the entrance. There was a cold draft sweeping in and the audience wisely stuck together.

Matt and I separated almost immediately. I told him I’d see him later and headed for the main bar. I was in the mood for gin and conversation. I didn’t feel the alcohol in my system yet so I felt anxious. There were plenty of women around to talk to, but being alone seemed to put a lot of pressure on me. It wasn’t really just the act of being alone though. I always pushed myself & have always hated excuses. There would be no excuses tonight. There would always be that next glass of Gin anyway.

I waited on the left end of the the island bar. The bartenders were slow so I decided to try my chances at the opposite end. While I was pushing through, I caught an attractive brunette looking over my way. I assumed it might’ve been someone else she may have been looking at but I maintained eye contact anyway. I kept pushing through and when I was near her I said the first thing that came to mind. “Are you having fun tonight?” I instantly regretted that and felt dumb. She turned around and seemed to erase me from existence. I thought fuck it, I got the first one out of the way.

I finally got my Tangeray Tonic. I felt sober but committed. I walked over to the back of the crowd while the music blasted throughout the place. I positioned myself beside two blonde girls. Neither was particularly attractive, but I knew I had to push myself.

“So who are you guys here for?”

The shorter blonde girl with dark streaks in her hair was the most responsive. The conversation among the three of us was generic and forgetful. It started with questions and continued with even more. It then gravitated between me and the shorter blonde with streaks. After about five minutes of cherry picking I had had enough. I was still in the same position that I had started out in and knew my chances of achieving anything with these girls was getting slimmer by the second. I told them it was nice meeting them and that I was off to find my friend. Maybe I’d get another shot later. Sometimes you just have to know when to catch & release.

I felt like giving up. There really was no shame in doing so. It was a Tuesday night and I had no business really being at this show. The conversation between me and the short blonde centered around Girl Talk, someone I knew nothing about. As a result, I was facing an endless night of Girl Talk conversations and pretending I gave a shit. Usually when I go out, I feel like an actor. That night I felt like an actor who was way over his head.

I wandered around slowly. The slower the better. It meant I was eating up more time and maybe combined with my new glass of gin the night would simply pass me by. I ended up at the bar several more times. I took my time ordering. I felt ashamed that I wasn’t even attempting to talk to anyone. The alcohol building up in my system made it worse.

A refill later and I’m walking away from the bar. My mind is clear. Nothing is biting tonight. I couldn’t make anything work. It’s okay, these things happen.

“Mike!” someone shouts.

Matt was standing a few feet away in front of me. He was with two blondes. One was very attractive. It was hard not to look at her. The other was a lot older. She looked like she may have been attractive when she was younger, but tonight she looked like the years weren’t treating her kindly.

“Mike! Get over here man!” Matt said as he motioned towards them.

“Hey what’s going on?” I smiled at both ladies and gave a slight nod towards Matt. “You finish taking pictures?”

“Yea, I got some good shots. I’m good though. This is Jessica and Bobby Sue.” He put his hand on the very attractive Jessica’s hip and then tilted his head to introduce the old lady that had the most redneck name I’d ever heard of.

I shook hands with Bobby Sue and realized that this meant I was taking one for the team. I had no intentions of doing anything with her. Her face wasn’t wrinkled so much as it was worn out. I could tell she was doing her best to keep her hair looking fresh and vibrant. Her face was a different matter. It had too many years of tanning and her make-up was obvious. I began to grind my teeth and let Matt isolate his girl and owe me one. “Did you guys enjoy the show?”

“It was great! I’ve never been to this place, Jessica invited me out.” Bobby Sue smiled and looked more excited than she should’ve been.

“Yea, I’ve never actually heard of Girl Talk before. Matt had a plus one, so I figured why not. It’s a pretty good way to spend a Tuesday.” I felt above Bobby Sue. It could’ve been because her looks weren’t great, but it had a lot to do with the way she responded. It was immediate, followed by a smile and deep eye contact. Her eyes widened as she said, “That’s cool.”

“You want to get a drink?” I asked.

“Sure,” she turned to Jessica and Matt, “Are you guys coming with us?”

“Where? The bar?” asked Matt.

“Yea, let’s get some drinks,” I said. I figured since I couldn’t get Matt alone with his girl, I might as well take the initiative and make it so I was the one leading them all back. It’s always a good idea to do things on your own terms.

The three of them followed me to the island bar. I found a spot with a clear opening to the bartender with ease. “What are you guys drinking tonight?”

“Get me a vodka club,” Matt answered.

“What about you girls?” I asked, teasing them about their age.

“Vodka Cranberry is fine for us.”

I ordered three Grey Goose & Cranberries, mainly to keep the mood going. Matt was disappointed since he hated drinking liquor with any type of non-diet mixer. He took it anyway. I ordered myself another Tangerey Tonic since it seemed to be working out well for me.

The girls started peeking into their purses as the drinks were being served. I handed each of them their drinks. “Relax, I just won the lottery.” They both laughed and closed their bags.

“What are you drinking?” Bobby Sue asked.

“Tangeray Tonic.”

“Must be good,” she said.

“It’s gin. It does what it’s supposed to.”

Matt had finally gotten Jessica alone again. Well, as alone as you can be in a concert. I was face to face with Bobby Sue. The conversation was meaningless. The beer goggles were really starting to take effect. I was back on track. I knew exactly what to do.

“So how old are you?” Bobby Sue asked.

“I’m 15,” I said immediately.

Bobby Sue broke out in laughter. “You know I’m old enough to be your grandmother!”

“Is that so?” I put my hand on her left hip and held it while we talked.

“How old do you think I am?”

“Oh, well, I’m pretty good at this.” I paused to build up some anxiety on her part. “25.”

More laughter. “That’s good. You’re funny. I’m 55.”

“Oh, so a little off,” I responded as I brushed off that insane number.

“Just a little.”

We finished our drinks. I had had enough of the small talk. This woman would not stop smiling at me. I had both hands on her hips. It was time to escalate. I leaned forward and started kissing her. Matt looked on in shock, but hid it well. I know I saw Jessica’s look of utter disbelief. Matt stopped us.

“You guys feel like getting something to eat?”

I stopped kissing Bobby Sue and answered, “Sure. Let’s go.”

The girls didn’t have any ideas. Matt and I had both been on dates to Mandarin Oriental, or MoBar for short. We discussed the idea and agreed to go there. It took us some time to find a cab. Matt was vocal about leaving his car behind. I managed to convince him to take the ride with us. We had a change of plans as soon as we arrived at Columbus Circle.

“Wait a second. I’ve been here a bunch of times. There’s a restaurant in the mall here that we can go to,” Bobby Sue explained.

“Sounds good to me,” Matt replied.

We entered the mall and went up the escalators. The restaurant was fancy. MoBar itself is fancy, but in a smaller more exotic way. This place was more of a restaurant. It also had private booths along with stylishly sleek tables scattered throughout. Matt and I decided to get a booth along with the privacy it provided. The booth was circular and connected to the ceiling. It was basically a tube with one wide opening. I sat down first as I edged myself all the way to the right side. Bobby Sue followed, as did Matt with Jessica afterwards.

I decided to start throwing money around once we were all seated. I ordered a $100 bottle of white wine, fried calamari, and some other plates of appetizers that the girls had asked for. The bill was piling up. I knew it’d be hefty. Matt got anxious about it and let me know with a few stern looks. I gave him a nod and a quick wink to let him know it was on me.

The wine went quickly. I ordered another bottle, much to Matt’s dismay. The food tasted fine, but for some reason none of us was hungry enough to finish any of the food we had ordered. We tried picking at it but eventually we gave up. I’d soon realize that Bobby Sue had other things on her mind rather than food. Bobby Sue turned to me so I started kissing her again. To my surprise, her hands wandered over my pants. I didn’t know how to react, so I just kept kissing her. Then she unbuckled my belt.

“Wh-What are you doing?” I said stuttering and holding back my laughter.

“I’m thanking you for dinner.”

As soon as she said that, my penis was already out of my pants. I was completely against doing anything in public, but her hands moved too quickly. They had a lot of experience. I was even more against being exposed in front of my friend as well as hers. They didn’t say anything as she leaned over and started giving me a blow job.

This was the first erotic experience I’d ever had in front of other people. I wanted her to stop but I was powerless. I was surprised that I even had a full erection going. I didn’t dare look over to Matt or Jessica because I don’t think I could’ve handled their expressions. I didn’t want to be judged. I kept looking at the side of Bobby Sue’s face as she continued to perform an obscene act in full view of, for all I know, innocent families.

I had had enough. I’d been to jail before. There was no way I was going to get arrested over this. I wasn’t drunk enough for this insanity. I pulled her shoulder up and she backed off. I covered my erection with my hand. I couldn’t tuck it in immediately so I did my best to at the very least conceal it.

Bobby Sue then managed to climb over me and get into a straddle position. I was in shock. I thought this woman was trying to have sex with me in the middle of a classy restaurant. This sudden jolt of fear was exactly what I needed to tuck myself back in. Bobby Sue didn’t mind. She leaned forward and we continued kissing once more. I was still aware of how crazy this must’ve looked to other people, so it started losing the sexiness it originally had started off with.

“Let’s get out of here,” I said.

“Where do you want to go?”

“My place,” I replied.

“Where?”

“Hoboken, my apartment. Cabs are quick.”

She got off me and sat back in her spot. The waiter arrived just in time for me to ask for the check. The girls then decided to get up and go to the bathroom. The waiter came back with the bill. I looked into my wallet and felt a sense of dread. It was empty. “Yo, dude… I forgot my cash.”

“What?” Matt was more disappointed than angry.

“Dude, you know I’ll get you back.”

He sighed. “I know man… Just pay me back when we get back to your place.” He shook his head in disgust as he paid the bill. “You’re so lucky I can cover this. Jesus Christ.”

Two guys then walked up to our table. They were laughing as they looked at me. I was a bit out of it and didn’t realize they were pointing at me. I thought they had something to do with the bill and was going to let Matt handle them.

“So this is what goes on in these private booths?” asked one of the men while the other kept laughing.

“How do I get your table?” asked the other guy.

Matt didn’t answer so I shrugged my shoulders. They walked away laughing. I didn’t realize until later that they must’ve seen me getting a blow job for a minute or two. They definitely saw Bobby Sue straddling me. They might’ve even thought we were having sex.

The girls came back. We got our coats from coat check and went downstairs to hail a cab.

“I need to go get my car,” Matt said.

“Dude, just pick it up later. You don’t want to drive right now.”

“No, I really do. I’ll be fine and right behind you. Just take the girls and I’ll meet at your place.” A cab stopped in front of us. “Take the cab and go. I’ll be 10 minutes behind you,” he explained.

Bobby Sue was continuously grabbing me. She wanted me to get in the backseat with her and Jessica. Bobby Sue would’ve been in the middle while I was on the right. I refused. I told her I’d be in front. I really did not feel comfortable with her after what had gone on in the restaurant. I absolutely did not trust her in the backseat. As a result, I got into the front after making the cab driver move his books and paperwork.

It didn’t take long to get to my place. It was late and there wasn’t any traffic in the Lincoln Tunnel. As we arrived on my street I told the driver, “Stop at that first light that’s shining on the left.” I then paid for the fare, with the last few bills I had left, and led the two ladies inside. “Matt should be here soon. I’m right up here.”

The girls followed me up the 3 flight of stairs. I opened the door to the apartment not knowing what kind of chaos would soon ensue. Matt was probably going to take awhile to get here. Bobby Sue didn’t seem like the patient type. It didn’t even occur to me that I should have been trying to raise the stakes to see if Jessica was just as wild as her friend. No, instead I poured her a drink, switched on the television and led Bobby Sue into my bedroom.

There was some quick kissing. Our clothes came off quickly. I closed my door and Bobby Sue ripped my button down shirt open. I was momentarily stunned and angry at what she had done. I didn’t realize until later that she had miraculously ripped open the shirt without ripping any buttons off.

We were naked as we climbed into my unmade bed. She had a surprisingly great body for a 55 year old. There wasn’t a pinch of fat on her. She wasn’t as tight as someone half her age could be, but she could’ve gone into the exercise videos for older women business had she played her cards right. It was impressive enough to distract me from her otherwise unattractive face.

As if on cue, Bobby Sue began to fellate me. Her technique was something to appreciate. I had no idea that she was simply getting me ready. It didn’t take long. I was at full attention once again, even with the copious amounts of liquor in my system. The adrenaline coursing through my body was intense.

“I want you to titty fuck me!” she said unabashedly.

I had never titty fucked a woman before. This was something I had been eager to accomplish. “Yea sure,” I said trying to make it seem casual.

“Do you have any lube?” she asked.

“Ugh…I… no. I don’t think so.” I didn’t know what to say. I didn’t think you needed lube but I also didn’t want to sound like I’d never done this before.

“That’s okay.” She then leaned over me and grabbed an open Corona bottle that had been sitting on the night desk beside my bed. I’m not sure how long exactly it had been sitting there, but it had to have been a week.

“We can use this,” she said.

Bobby Sue then splashed the old Corona’s contents onto her cleavage. I was shocked and excited simultaneously. I wondered, was this odd? I didn’t care. I sat up on my knees and let her get to work. She pressed her well proportioned breasts together and I thrusted in and out. I thought, I could definitely get used to this. I also thought that it’d be a shame to waste an insane night like this on just a titty fuck. I had accomplished a first, but it was time to get that notch.

I laid her on her back and we started having sex. I didn’t bother hunting for a condom. In my defense, everything was just happening too quickly. I was thrusting away and doing well. I could tell my stamina was up to par. This was going to be fun. That’s when I noticed how sticky our bodies were getting. The old beer was all over our chests as well as the bed. I decided to switch up positions. “Let’s do it on all fours.”

She immediately got on her knees and faced the end of the bed. I continued having sex with her and I couldn’t help but smile. This was insane. I was having sex with what was most likely a grandmother. I mouthed out the word ridiculous in silence. I then pointed at the mirror to the left of my bed and imitated Christian Bale’s sex scene in American Psycho.

My mind must’ve been wandering. I thought about something Matt had once told me. He had said he loved sticking a finger up a girl’s butt during sex. He said it was something he thought everyone did. I told him he was nuts and that no one does that. He simply shrugged his shoulders and said that no one ever minded. I decided to test the theory.

I was still thrusting as Bobby Sue was on her knees. She kept getting closer to the end of the bed. I slowed down a bit so I could finger her asshole. At first I was cautious. I didn’t know what to expect. I wondered if it would end up being disgusting or if she would get angry. She didn’t say anything though as I slowly guided my pointer finger in. I now had my finger sliding in and out of her ass. There didn’t seem to be any mess. I continued and my curiosity got the best of me. I started to feel around in a circular motion.

“Why don’t you stick something bigger in there?” Bobby Sue asked.

Jesus, I had never had anal sex before. I was satisfied with my first titty fuck, but now this? I didn’t think twice. I was in too deep, literally. I pulled out of both parts of her. I was going in.

I’d seen movies and television shows where the main character looks up anal sex before trying it. I didn’t think pulling out my laptop would’ve been a smart move though. So all I had to work with was what I had in front of me.

I held my shaft as I tried to squeeze it in. It was proving difficult. I thought, what the hell and just tried to force it in even harder than before. The nerves must’ve gotten to me because I applied too much force too quickly. I hit her ass on and angle and as a result ended up bending my penis at the base.

The pain was surreal. I bit into my hand and held in a scream. I saw the base of my penis swell up and turn purple. The pain was coming in waves. The adrenaline was still coursing through me and it managed to blend the pain into the background. The alcohol was a blessing, but the mission at hand was all that mattered, crooked dicks be damned.

I fingered her asshole as I tried to recompose myself. I had learnt my lesson. I had to approach this slow and steady. Once I was ready, I ignored my bruised shaft and slowly forced it into her. I was in, I had done it. I guided myself in and out. I would occasionally pop out. It felt decent, definitely tighter, but it’s not something that I would truly recommend to anyone. I would slip out anytime I sped up. What I noticed was that Bobby Sue would wince every time I reinserted myself. I thought it was amusing at first, but I quickly found it oddly stimulating. I tried to keep from slipping out again though since I figured it was time to finish up. I managed to keep it together until I ejaculated in her. I didn’t know how she would clean up later, but I figured this is what you were supposed to do.

I then leaned forward over her back. We were still sticky and now I had to deal with the aftermath of what my shaft would reveal. I was too concerned about my manhood to realize just how dangerously close to the edge of the bed she was. When I slipped out of her, she too slipped, right off the end of the bed. She fell forward and landed on her neck. I couldn’t stop smiling and thinking how outrageous this night had been. I just looked at her laying there naked in a heap on the floor. After awhile she still hadn’t moved. For an instant, I thought the worst. She couldn’t be dead, could she?

“Sue!” I exclaimed. “Bobby Sue, are you okay?!”

She moved, to my relief. She just needed help. She was stuck with her ass in the air and with her neck on the ground in an awkward angle. I kept myself from laughing as I helped her up and we sat down on my bed. I thought I had just sodomized a grandmother to death.