Cheering Mom Up

"So, what do you think?" she asked sheepishly.

"At the risk of this sounding weird, I would say that whoever you allow to see this particular ensemble will be very lucky and very pleased."

"Thanks! It will most likely be nobody though."

"I'm a bit conflicted because I want to be your positive and supportive wingman. But, on the other hand, success in this scenario would involve some dude banging my mom," I jested.

She chuckled, "Yeah I guess this has been a strange conversation what we've been having. Anyways, what time is the movie?

"I think the next showing is in about a half hour so we should probably get going."

"Oh, well then I better get dressed real quick and then we'll head out," she said as she turned around to the outfit that she had laying out on the bed. I hadn't ever really noticed before but, seeing it in her tiny underwear, my mom had a great ass. It might not be as tight as it was when she was younger but it still looked phenomenal. In fact, it made me feel a little uncomfortable how nice I found it.

I got over that weird moment quickly and we got in the car to head to the movie. As we got to the theater, I was surprised to find a very long line for a matinee movie. After a couple of minutes in the line, my mom put her arm around my shoulder and asked, "How does it make you feel to be in a line like this for a Katherine Heigl rom-com?"

I realize that it is a pretty corny thing to say but, whatever, it's my mom so I wrapped my arm around her lower back and said, "At least I have good company!"

She smiled and gave me a kiss on the cheek. I bought the tickets and popcorn before we went into the theater. As the previews came on, I was reminded of exactly what I was in for. They were filled with other upcoming corny rom-coms. After a couple of them, I looked at my mom and gave her a playful eye-rolling which seemed to particularly amuse her. I wouldn't admit this to her, but I actually didn't hate the movie. Part of that probably had to do with the fact that she seemed to love it so much. With knowing how lonely she has been, it made me feel great to see her laugh so much and seem so happy if only for those two hours....or this weekend for that matter.

As the credits started rolling, we walked out of the theater. Seemingly assuming she knew the answer, mom asked, "So what did you think?"

With a grin on my face, I responded, "I cannot believe that, against all odds, the guy and the girl got together in the end. I totally did not see that coming."

She laughed, then followed up with, "I think you liked it though. I saw you laughing a few times."

"It wasn't the worst movie I've ever seen. I'll give you that much."

"So what do you want to do now? Should we go get something to eat?" she asked.

I thought about it for a second and said, "To be honest, I'm actually pretty full from the popcorn. What do you think about grabbing a few drinks somewhere? We could get a small bar snack or something."

"That sounds good to me. I'm pretty full too."

We ended up just going to a pool hall that was nearby. I was about to order the drinks before she stopped me, "No no no. You got the movie, I'll get the drinks. What do you want?"

"I'll just take a beer."

She turned to the bartender and asked, "Can we get a lager pitcher?"

Being that it was still fairly early, we did not have any trouble finding an open pool table. As I saw my mom attempting to do the rack, I realized that I had never seen her play pool before. Judging by where she placed the eight ball in the rack, I assumed that she wouldn't be great. After I missed a shot and it was her turn, my assumption was verified. The way she held the stick made me think that she might never have even seen somebody play the game before. Unsurprisingly, she missed the shot horribly.

I then took my turn. I made two balls before missing. As I saw her awkwardly approaching her next shot, I decided that I'd step in, "Here. Try doing it like this," I tried just showing her with my own pull stick but it didn't seem to take. So, I had to resort to the cliché pool-teaching position behind her. As I was showing her, I got a face full of her hair which smelled really, really good. I'm assuming it was her shampoo that gave off this very soothing vanilla scent. She was now ready for her shot. She lined it up like I showed her. She then displayed a much more smooth looking shooting motion and knocked in he first ball of the game.

"There you go!" I exclaimed. I then offered up a high-five which she happily accepted.

She actually ended up making three balls in a row on that turn. But, showing no mercy, I finished the game up on my next turn. At that point, the big soda from the movie theater and now the beers at the bar finally got the best of me. I told her, "Sorry, I gotta go to the bathroom."

"No worries! I'll be rack it up for the next game," she responded.

I walked into the bathroom that I would say was not the nicest I had ever been in. There were tons of paper towels on the ground and a plethora of horrible things written on the wall. But hey, it was a pool hall bathroom. What did I expect?

As I walked out of the bathroom, I saw a man that was clearly drunk talking to my mom. Judging by her facial expression and body language, it didn't seem that she was particularly happy to have him there. So, I made my way over to join the conversation. She saw me and looked extremely relieved that I was coming back. She yelled over to me, "Hey, sweetie!"

The guy barely seemed to notice and continued talking to her, "Come on. Let me get you a drink."

Very politely, she said, "I appreciate the offer but I'm here spending time with my son."

"It's just one drink. He'll be fine by himself for a little bit," he snarled.

I decided to step in, "Hey man, she said no."

He turned to me and clearly was not happy. He roared, "I wasn't talking to you."

"Well I'm talking to you because you don't seem to be listening to her. You just need to cut your losses and leave her alone."

After hearing this he gave Ryan a shove and raised his voice even louder, "I don't want to hear another goddamn word come out of your mouth."

"Listen man, you need to just walk away because this won't end well for you," I said. I felt very confident in this situation. First of all, this guy seemed to have hit the bottle pretty hard. Also, and probably more importantly, I am about six foot four and a pretty solid 210 pounds. This guy was not particularly small but he definitely gave up some size to me.

After hearing me say that, he slightly turned to make it look like he was going to walk away but then quickly cocked his right hand and tried to throw a punch. I blocked the blow with my left hand and caught him square in the nose with my right. He went right down to the floor with that one which caused the bartender to run over. He grabbed the drunk man as he tried to get up and come back after me. He began to guide him towards the door and said, "Alright, Frank, get your drunk ass out of here."

The bartender then came back over to us and said, "Sorry about that. Frank can really be an asshole. I know that you weren't causing trouble here but I think it might be in your best interests to get out of here. We often have trouble with Frank and I wouldn't be surprised if he came back in here with some of his cronies."

I cordially replied, "Thanks for the heads up! Have a good one!"

My mom and I got in the car and pulled out to find a new place. She looked over at me and said, "So that was crazy."

"Seriously!"

"I'm not sure what he thought the best case scenario there. Like did he think that I was going to leave my son to go have sex with him at six o'clock?" she asked.

I replied, "I have no idea. We gotta find a better example of the dating scene for you than that. Are there any cool lounges or pubs around here?"

"Well, we could go to Benny's. It's just a few blocks away."

"Sounds good to me," I said.

As we walked into Benny's, there were a decent number of people in there but it was not too crowded. We walked over and found a small table in the corner. The waitress came over to us almost as soon as we sat down. With a glowing smile, she said, "Hi, welcome to Benny's! Do you guys wanna see a menu?"

I looked over at my mom as we attempted to telepathically tried to discuss this question but was mostly just an exchange of weird facial expressions. Finally, I turned back to the waitress and said, "Can we get a drink and food menu?"

"Absolutely! I'll be right back.

And she was right back. We took turns looking at the food and drink menus. We decided to split some curly fries. I got another beer and she chose a vodka cranberry this time. Since our fries were taking a little while to come out, we got through those first drinks fairly quickly and our waitress promptly brought us another round.

Our fries finally came out and, with it, another round of drinks. The fries were delicious and we knocked them out in what seemed like two minutes. After we finished the next round, the waitress came over and asked, "Are you guys ready for another round?"

My mom took the reins this time, "Yeah that'd be great. But can we also get a shot? Tequila?" she asked while looking at me to seemingly get approval.

I wasn't particularly excited about doing shots of tequila but I faked some enthusiasm, "Let's do it!"

That shot really took me back to college and not exactly fond memories of it. But, my mom seemed to be having fun so it was a small price to pay.

I began to realize that if our true purpose of the night was to get her back out into the dating scene, then me sitting at this table with her would be extremely counterproductive. So, I told her, "None of these guys are going to come up and talk to you while I'm sitting here. I think I should just sit up at the bar for a little while."

She looked a little uneasy. After a moment, she replied, "But I don't even know what to do. It's been three decades since I've had to do this."

"You don't really have to do anything. Trust me, they will come up do you in droves and you just have to be your normal, charming self," I assured her.

"Okay, I'm trusting you," she pleaded.

"You'll be fine."

She gave a brief smile and said, "Okay. Wish me luck."

"You don't need it....but good luck."

With that, I walked over to the bar. As if on cue, a pretty good looking man walked over to her from across the bar. He looked to be slightly younger than her but she looked so good for her age that it wouldn't really matter. I kept an eye on them as I continued to down more beers. Other than one moment about a minute in where she glanced over at me, this guy seemed to be doing a good job of keeping her attention. She played with her long, blond hair and occasionally gave him a playful slap on the arm, along with many of the other tell-tale signs of female flirting. In fact, she talked to him for over an hour. I just watched a basketball game in the meantime.

Eventually, she came over and sat down next to me. Confused, I asked her, "What happened to that guy?"

She responded, "We actually really hit it off. He's a lawyer. He was pretty funny. We actually went to the same high school but he graduated a few years behind me."

"So what's the problem?" I asked.

"Well, he just split up with his wife. It sounds like they're probably going to get divorced but I honestly don't want to get into something so complicated."

"I don't blame you. Was he upset?" I asked.

"Well no but that's because I wussed out. I gave him my number but told him I couldn't go home with him because I was here with you," she confessed.

"Well played. Well I think he left. Why don't you go for round two?"

"I have to go to the bathroom first but I will after that."

Shortly after she left, our waitress walked up to the bar. She looked a little tired, then she noticed me. She asked, "What happened to your date?"

I laught a little at this and replied, "That's actually my mom."

She looked embarrassed and apologized, "Oh I'm sorry!"

"No worries. I'm actually trying to be her wingman tonight," I told her.

"No offence but I don't think she really needs your help. She's got super-MILF status," she told me in a very playful way.

"Believe me, growing up as her son has made me fully aware of that. I guess I'm just here for moral support. My dad died a few years ago and I'm trying to help her get back out there."

"Oh I'm so sorry to hear that! But that's really sweet of you!" she exclaimed.

"I'd love to fully accept that description but I haven't been back to see her for about a year," I admitted.

"Oh yeah? Where do you live?" she asked.

"I live in LA....with my fiancée," I begrudgingly told her.

"Oh, you're engaged? Well that's just my luck. I find a sweet, good looking guy. It only makes sense that you're attached," she said with a somewhat joking frown-face.

"Well if it makes you feel any better, the scumbag inside of me almost kept me from telling you that I'm engaged because of how attractive you are," I told her.

This definitely made her smile. She really seemed mull over what she was going to say next. Eventually she managed, "Well, I don't know how long you're gonna be in town but maybe we can exchange numbers and I can wing-woman for your mom."

"I guess there's nothing wrong with that. I actually think the two of you would really get along."

"Oh yeah? Who knows, she is single. Maybe she could get me to switch teams," she joked.

"You're making my penis very confused. I really like the thought of you being with another woman but that other woman being my mom kinda puts a damper on it," I joked back. I wouldn't say it out loud, but the thought of the two of them together didn't really gross me out all that much. That could probably be chalked up to the fact that she was incredibly hot.

She seemed to be very amused by my penis confusion. She then grabbed my phone and entered her phone number into it. She then said, "I'm calling myself right now but I should probably get back to my tables."

"Well it was nice to meet you," I looked down at my vibrating phone, "Kelly."

Shortly after that, my mom got back from the bathroom. Apparently, she had seen me talking to Kelly, "You looked to be getting pretty flirty with our waitress."

"No, it's not what it looked like."

I hadn't quite noticed earlier but mom had gotten fairly drunk., "You don't have to explain anything to me. I think it's good for you to experience different women before you take the plunge. Marriage is a big commitment and it's best if you have as much information as possible beforehand. A night with a hot little piece of ass like that could be good for you."

I was slightly taken aback to hear these words coming out of her mouth, "I never thought I'd hear you describe someone as a "piece of ass". Maybe I'll try it out. I love Sarah but I'd be lying if said I didn't have any doubts. Kelly, that's the waitresses name by the way, did give me her number. She said that she could probably be a better sidekick for you than I am when you're out looking for guys."

"Oh, well, maybe we should see if she wants to go out with us tomorrow."

"Maybe," I replied.

After that, we both assumed our positions. Again, almost the second that my mom was at the table by herself, another guy came over to talk to her. This guy looked even younger than the first. At first, she didn't really seem to be that interested. None of the signs that I saw with the earlier guy were manifesting this time. However, a few minutes into their conversation, he said something that absolutely made my mom explode with laughter. Once I saw that she was into it, I went back to watching the game.

During a commercial break, I looked back at the table to see how things were going. I was a little nervous to see that there was nobody there. Somewhat frantically, I began to scan the bar. This scare was short-lived though because I located the two of them out on the dancefloor. To my delight, they both seemed to be having a great time.

"Looks like she found one," I heard and turned to find that it came from Kelly.

I answered, "Yep. He might be a little young for her but she looks to be enjoying herself."

"Like I said earlier, your mom is a hottie. She could come out here and take home college guys if she wanted to," Kelly retorted.

"So what's my move here? Do I head home? Let her do her thing?" I asked.

"I would just shoot her a text and see what she wants to do."

Kelly quickly had to run somewhere but I took her advice. I sent my mom a text saying, "What's the gameplan?"

I watched my mom. I saw her phone light up in her purse and, luckily, she saw it too. After she read it, she turned to the guy she was with and said something. They looked to be exchanging numbers, she gave him a peck on the cheek, and then she walked over to me. I asked her, "What's going on?"

She said, "Let's get out of here."

"Are you sure? You guys looked like you were hitting it off."

"Yeah I'm sure. I'm gonna make him work for it," she said with a sly look on her face.

"Okay."

With that exchange, she went back over to the table to grab her coat. Kelly returned to the bar, so I updated her, "She said she's gonna make him work for it."

She laughed and said, "Good for her. I'm sure he will work for it too."

All of a sudden, my mom jumped into the conversation and showed her drunkenness because she was just shy of shouting, "Thank you so much for the great service! Ryan tells me that you might be interested in being my wingwoman."

Apparently very used to people in this state, Kelly didn't miss a beat, "Yeah I'd love to. I guarantee I'd be of more use to you than this guy," shooting me a teasing smirk.

My mom turned to me and said, "I like her," then turned back to Kelly, "What's your name by the way?"

"Kelly."

"Well, nice to meet you Kelly. I'm Julia. I sure hope that you can hang out with us tomorrow night," my mom said as she wrapped her arm around my shoulder.

"Well, I'm supposed to work but I'll see what I can do," Kelly responded.

"Sounds great!" mom exclaimed.

I finally jumped back into the conversation, "I think we're gonna get going but I'll get in touch with you tomorrow."

"Alrighty! I'll talk to you tomorrow," she said with a smile and a wink.

With that, we headed out the door with my mom's arm still wrapped around my shoulder which I realized was about as much for support as it was for anything else. She was drunker than I had ever seen her before. I realized that, while I wasn't as bad as her, I also was in absolutely no shape to drive. So, I called a cab to take us home and decided to leave the car there for the night.

When we got home, my mom had to run upstairs to go to the bathroom. We she came out, it looked as though simply standing there was difficult for her to do. In fact, she had to lean up against the wall as she said to me, "I like that girl Kelly. I remember when I used to look like her....young guys like you going after me."

I countered, "Are you kidding me? Guys at that bar were lining up to try to talk to you."

"You're sweet," she said as she seemed to half doze off while leaning up against the wall.

"Why don't we get you to bed," I offered. She latched onto me again as I led her into her bedroom.

Right before we got to the bed, she turned towards me and had my face cupped in both of her hands. She then ran her right hand through my hand as she said, "You always take such good care of me, Jack," she then cupped my face again and gave me a kiss on the lips. Now, this was not a peck on the lips like we've done tons of times before. This was a deep, passionate kiss. Now, I should have been freaking out because my mom called me by my dead father's name and was now kissing me in a very not mother/son way but all I could think about was how soft her lips felt. Without even thinking, I put both of my hands on her nice, firm ass and pulled her in closer to me. We were now exploring each other's mouths with our tongues. My penis was rock hard at this point as it rubbed up against her body. With my hands already on her ass, I picked her up and laid her down on the bed. As we continued kissing, my hand made its way down inside of her pants. Through her panties, I could feel that she was already extremely wet. For some reason, this seemed to snap me back into reality as I realized that I was making out with my mom and was just about to start fingering her. Not only that, she was probably blacked out at this point and I was essentially about to take advantage of her.