Big thanks to MissScarletInTheLibrary for reading over this chapter for me to help me fix the direction and tone. I hadn't really been happy with it, but her outside observations helped me work out the kinks and I feel much better about it.

Part 12: Jumping In

The next two weeks pretty much followed the same pattern on most nights. After a show, Jon would hit up one of his regulars or find a new little skank to stick his flag into. He would call me once he sent them on their way and regale me with the details while I masturbated listening to him. He thought it was funny at first, but I think he got as much enjoyment out of it as I did. I was still timid about it the first few times, but I eventually became comfortable enough with masturbating on the phone that I started to get really into it. I would help narrate his story by asking specific obscene questions for him to answer. I think it was getting him off a bit, too, because by the second week, I swore I could hear him jerking off on the other end.

It was a fun little arrangement.

However, one Saturday night when I got his text, I was not in a very good mood. The bar had exploded with people early in the evening and it was busy right up to closing time. I didn't even check my phone when I felt it vibrate in my pocket because I already knew what it said. Out of the last six days, he had hooked up with different chicks five times. I knew he got around, but I don't think I realized that he was this active. Maybe if it had been a quieter night or I hadn't been working, I wouldn't have cared as much, but I was already stressed out and riled up, so this did not improve my mood.

Larry noticed my frustration and called over to me, feigning wanting another drink.

"What's the matter, sweetheart? You've been in such a good mood lately," he inquired.

I gestured around the room. "Do you not see how busy it is tonight, Larry? It should be obvious why I'm frazzled."

He stared at me, rubbing his stubble-covered chin. "No, there's more to it. I've seen you stressed when it's busy before, and there's something different about you right now. Promise you'll tell me after last call, El?"

"Yeah, sure, whatever. I'll let you stay a little later, but I'm only going to serve you water, old man," I said with a wink.

When the final patrons were out the door and I successfully locked it behind them, I slumped against the wall and slid down to the floor, exhausted. I groaned rather loudly and Larry came over to help me up.

"Thanks," I mumbled. Dave and I started cleaning up while Larry listened to me rant.

"I think I'm starting to get a little jealous of Jon," I said, getting right to the point. I was too tired to pussyfoot around. "It's like he's trying to win some award for fucking a different girl every night and I've just been masturbating to him telling me about it after. It's fun, don't get me wrong, but I feel like he's the only one really benefitting from this open thing."

"Have you tried getting out there yet?" he asked.

"No, not yet. I figured it was too early. I mean it's only been a little over two weeks since we decided to do this. I thought I'd ease into the dating pool, but he cannonballed."

"I think he's cannonballing into the STD filled hot tub," David quipped. I sighed and gave him a sad look. I wasn't quite in the mood for jokes like that. "Look, El, if this is what he was doing before he asked you to be his sort-of girlfriend, and you agreed that it was fine for you guys to sleep with other people while still supposedly being with each other, I don't think you can really be upset at him for simply continuing to do what he does."

"Maybe…" I pondered.

"I think it's just time for you to go out and try to get a little something for yourself," suggested Larry.

"Listen to him, El. He's old and wise and was a horny teenager in the 60s, so he knows about crazy free love and all that shit." Right on cue, Dave made the save and got me to smile for the first time that night. "On your next night off, put on a hot little number, go to a crowded bar, and I'll give you a bat to beat the dudes away."

I giggled and gave him a hug. He seemed awfully confident in me, but I still wasn't quite convinced in myself. "I guess I'll have to go buy a little black dress or something tomorrow, then."

"Do you still have that outfit you wore when you were out with the wrestlers a few weeks back?"

"Yeah, but-"

"Wear that," Dave interrupted. "Trust me on it."

So another Monday night came, but instead of watching Raw, I got ready to go out looking for a new man for the evening. I put on the outfit Dave had suggested and stood in front of the full length mirror on the bathroom door. Staring at myself, I couldn't help but feel a little self-conscious. It had been so long since I had gone out alone, let alone gone out at all, really. Could I pull this off? I sighed and lightly smacked my face. You gotta get your game face on, girlie, or this will be a rough night. I turned around and glanced at my backside. These jeans did make it look surprisingly good. I guess the guys weren't just humoring me about it. I smiled and blushed slightly at this thought. Yeah, you look good, Lana, you can do this!

Confidence now up a notch, I left and headed to a more popular "hip" bar further into the city. It was nothing like my bar, but I suppose I didn't really want to go looking for a sex partner in a place like my bar. I tried squeezing through the sea of people surrounding the bar so that I could order. Ugh, all these people, laughing and flirting like douches. No, Lana, you have to be less judgmental and more charming or something if you want to try to use this ticket to ride.

Once I finally wiggled my way up to the front and caught the attention of one of the bartenders, I ordered a vodka cranberry. That drink seemed simple enough. I didn't want to end up getting plastered tonight and going home with just anyone or making a fool of myself. After opening up a tab and receiving my drink, I moved back to the main floor and surveyed my prey.

Every relationship or random encounter I had previously was during high school or college and I always met the guys at parties or through mutual friends. I never had to fend for myself on unknown territory and I was terrified. I knew about some of the lame "rules" of picking up women, so I figured I'd try attempting them on men. I looked around the bar to try to find someone who wasn't in a group. I finally spotted an attractive guy sitting at a table and approached him, pulling up in my own seat.

"Hi, my name is Lana and I'm kind of new to the whole dating scene recently because I got divorced last year, but I'm sort of dating this guy now and he wants to have an open relationship so I have to get back out there as they say so that he's not the only one getting to bone random people while he's away. Yeah, it's sort of a long distance relationship thing. Those are hard, aren't they? He's on the road a lot because he's a wrestler and he's always busy. Do you watch wrestling? Oh, why would I be asking that right away? I love it, though. I suppose that's kind of obvious since I'm sleeping with one. He's really good at his job. And in bed, too. Haha, you look really uncomfortable right now. Oh right, I'm sorry, where are my manners, I haven't even asked you what your name is yet!"

The man raised his eyebrows, looking stunned. Then his eyes shifted to above my head and I heard the sound of a woman clearing her throat.

"Excuse me, can I help you?" the strange woman asked. I turned around and looked at her, horrified. "Can you please tell me what you think you're doing with my boyfriend?"

My mouth hung open for what felt like minutes before I started stuttering. Finally, I was able to put coherent words together. "I'm so sorry! I saw him alone and didn't know he was here with anyone so I thought I'd try talking to him. I didn't mean to interrupt your date. I'm sorry! I'm sorry! I'm sorry!" I quickly stood up and walked away, stopping to lean against a wall and calm down. Christ, I had barely had any of my drink, but I had rambled like I had a few. I sighed and banged my head on the wall a few times.

Okay, Miss Lana, this is no time to panic and leave! If you want to be equals with Sir Bangalot, you gotta get in there and fight!

I decided to give a shot to that ridiculous pick-up line David had suggested. I stayed by the wall and started looking at shoes, trying to find the nicest ones. No one would believe the line if they were wearing scuzzy sneakers, right? I spotted two pairs of what looked like really nice men's dress shoes - I really don't know a lot about shoes in general - and headed in their general direction.

The owners of these shiny new shoes were two handsome men who looked athletic and fit. What a lucky find for me! I approached them and took a deep breath before laying down David's very inappropriate line.

"Hey guys, nice shoes. Wanna fu-uhhhh…." I stood in front of the two men, staring at them, as they engaged each other in one of the hottest kisses I have ever seen. "Um, sorry, never mind," I awkwardly apologized as they turned to look at me. They were thankfully smiling, so clearly they weren't offended. "Um. Would you mind if I stayed and watched?" They both patted me on the shoulder with looks of pity and walked away.

What the fuck is wrong with me!? I gulped down my drink and asked the bartender for two more of the same. Clearly being sober was not working for me. I never would've guessed that I would be this bad at meeting new people. I dreaded David and Jon's reactions upon hearing of my plight. I could hear their laughter in the back of my head. Jerks.

I grabbed my two new drinks and went to go search for an empty table. Luckily for me, the table where stunned guy and surprise girlfriend had been sitting was now empty. Hopefully they weren't both in the bathroom now and would come back to find me stealing their table.

I slumped down into a chair and just nursed my drinks while watching people. Look at them all, easily creating new relationships and memorable moments. Sure those relationships wouldn't last past sunrise and those moments would be soon forgotten amidst a drunken haze, but I used to think that I could approach people and connect with them just as easily. Somewhere along the way, I lost that. How fucking depressing.

I rubbed my temples to try to relieve some of the stress I was feeling. This was turning into one of the worst nights ever. I just wanted to go back to my regular bar and drink with my regular patrons and listen to David laugh at my misfortune.

"Excuse me, miss. May I sit here?" I was startled back to reality by a good-looking man. I smiled at him and nodded. He sat down and continued. "I've been watching you and you looked a bit frazzled. I thought it was kinda cute." He took a sip of his own drink. "Also I liked your rack."

I looked down at my chest, clearly highlighted by the alteration that Jon had made to it, and blushed. This guy was awfully forward, but I did find him attractive and if he was approaching me, I might be able to end this night as a success.

"Thank you? I suppose it's a miracle what a push-up bra can do," I said while lightly adjusting my cups. "My name is Lana, by the way." I reached out my hand to shake his.

"Chad. So I'll cut to the chase. I've been watching you ever since you came in."

"That sounds awfully creepy, Chad. Did you have nothing better to do?"

"I know it sounds creepy, and I'm sorry for that," he said, chuckling. "I had been waiting here for almost an hour before I decided that yes, my date did in fact stand me up. What are you gonna do though, right?" He shrugged. "So I was people watching when you came in and I thought you were kinda cute and you looked quite nervous. It was endearing and I found you a lot more intriguing than these other people."

"I see." I took a sip of my drink and looked him up and down. "So how much of what you just said is total bullshit?"

He smiled and rubbed the back of his head. "Eh, not as much as you'd think, honestly. I was stood up, but it wasn't quite a date. I was supposed to be meeting this chick I met on the internet for sex." I nearly choked on my drink. I had not been expecting that one. "I had been people watching, but mainly in the hopes that I could find a new partner for the night. I did think you were cute and definitely getting frazzled the longer I watched, but I also overheard you talking to some guy earlier. It seems that you're in an open relationship and looking for someone to fuck tonight?" He smiled and raised an eyebrow at me.

"Good lord, well when you put it that way…" Now it was my turn to rub the back of my head sheepishly.

"So I'm not generally this forward, but I'm attracted to you and we're both looking for noncommittal sex, so if you find me attractive, would you like to come back to my place? I'm drug and disease free and I always wear protection, so you don't need to worry. Maybe we can have a drink together and see what happens?"

"I…uh…" I wasn't sure what to say. This was what I was looking for tonight, right? So why did I feel so weird about it? I thought for a moment and then decided to jump into the deep end. "Yes. I would love to." We both finished our drinks and paid our tabs. While he hailed a cab, I sent Jon a text.

Going back to some guy's place. Wish me luck?

Sitting in the back of the cab together, I discovered that Chad was not shy. Almost immediately after the cab pulled away from the curb, his hand found its way to my knee and it continued its way up my thigh. Thank goodness I had worn jeans or else he'd probably have his hand in my panties already. Whatever happened to the art of seduction, huh? He leaned over and nuzzled my neck. I closed my eyes and tilted my head away from him, allowing him access to go further. Nipping at my neck with his teeth, he slipped his hand under my shirt and up to my lace covered breast. I opened my eyes back up and made eye contact with the driver in the rearview mirror. I suddenly felt very uncomfortable. I knew I was being watched and I didn't really like it.

Chad squeezed my breast hard and I was jolted back to reality. "You looked a little distracted, baby. Are you okay?"

"Y-yeah, I'm fine." He didn't look convinced, so I grabbed his shoulders and planted my lips against his, shifting around so that I was facing him. We made out the rest of the ride while he continued to paw at my chest. I was enjoying it for the most part, but I didn't feel the rush of lust that I felt when I was with Jon, or even years ago with Scott. It felt like something was missing, but I couldn't quite put my finger on it.

When the taxi finally stopped in front of his apartment building, he paid the driver and got out. He walked around to the other side and opened up the door for me, which I have to admit was a very sweet little gesture. He reached out his hand to help me out and I hesitated. This just didn't feel right. As much as I wanted to try to be Jon's sexual equal in this bizarre relationship, I just couldn't go through with this. Not tonight. Not with Chad.

"I'm sorry, Chad, but I can't. I'm going to go back home. You're a very handsome young man, but I just can't go through with this." I reached to close the door and he stopped it with his hand.

"What's your game? Do you get off on leading men on or something? Why are you suddenly backing out of this?"

"No, it's not that. I just don't feel comfortable with this right now. I'm sorry!" I tried closing the door again and he thankfully moved his arm without pushing the issue any further. I gave the driver my address and he drove off. I turned to look behind me as we drove away and I was greeted by the sight of Chad, apparently ever the gentleman, flipping me off and grabbing his crotch.

I think I made the right decision.

"Ugh, David. Why am I so fucking stupid?" I sat at the bar, my face buried in my hands. He placed an open bottle of beer in front of me and I peeked at it through my hands. "Thanks," I mumbled.

"Do you really think you're stupid? Or are you just a little embarrassed at how badly the evening went?"

"Ha! A little embarrassed. That's a good one." I took a swig of the drink and sighed. "Maybe I'm just not cut out for one night stands."

"Well, I would've thought that myself if you had tried something like this last year, but you proved me wrong when you ended up hooking up with your little sex toy."

"That was different."

"Really. How so, El?" he asked.

"Well…um…"

"You're very convincing," he said with a laugh.

"Jon kind of seduced me, in a way. Maybe. I don't know. He was persistent. He loitered around the bar for an hour, asking me stupid questions and I got all frustrated and riled up, so I suppose I sort of wanted the physical release. Also, I hadn't been with anyone in seven months, so my body was wound up pretty tight and my lady bits overrode the logical part of my brain. But with this Chad guy, we spoke for maybe five minutes before I left with him. There wasn't any back and forth banter. I didn't really get a feel for him. Maybe that has something to do with it. I don't know. I just wasn't feeling it with him."

"Maybe you need to get to know someone somewhat before you're able to be physical with them? I mean, you didn't really know Jon when you did, but it's an idea?"

"Huh. Maybe." I took another swig.

"Why don't you try online dating? There are all sorts of horny dudes on there looking for sex, but you can search for one privately in you apartment and banter all you want before you actually meet up. It's worth a shot, El."

"I don't know what I'd even put down in a profile. I think I'd be afraid of overselling myself, so I'd end up making myself sound absolutely horrible."

"How about after I close up, I come upstairs and help you write one? I'm a pro at them. I used to do a lot of online dating before I moved here."

"Sounds good." I finished the beer and paid for it. "Just knock on the door when you come up. I'm going to go see if I can contact mister man."

I sent Jon a text telling him that my attempt at getting the most from this open relationship was a bust tonight as soon as I got through the door. I tossed my phone down on the bed, deciding that I'd go take a hot shower to clean off this dirty lingering feeling I had on me. I watched the soap suds circle down the drain as I rinsed myself off, the uncomfortable feeling that Chad had left on me going down with them.

I dried myself off and went to throw on a t-shirt and a pair of cotton pajama shorts. They were covered with a Hello Kitty design and they were my favorite guilty pleasure clothes. Once I was dressed, I flopped down on the bed and saw that there was a notification on my phone. Jon had replied to my text while I was busy.

Shame. I expect to hear all the details, bitch.

I sent him back a reply.

I'm not busy right now. Feel free to call when you have a moment and you can laugh at me.

Asshole.

I fixed myself something to eat and after a while, my phone rang.

"Hey Jon," I answered. "How was the show tonight?"

"It was pretty good. My shoulder feels a little stiff, but it'll be okay. But the more important question is how did you fail in getting laid tonight? I have to say, I'm disappointed in you." The sound of his laughter made me smile. As awkward an evening as it had been, at least it would become an entertaining story in the end.

"Well, first I went up to a guy sitting alone because, you know, those pick up books always say to get the target away from a group, right? So I figured a dude at a bar by himself might be lonely and easy to talk to. Well, rambled at him like a crazy bitch, basically telling him my life story of the past year, and then his girlfriend came back."

"No shit! That's awesome," he laughed into the phone. "Did she throw a drink in your face? Did a cat fight break out? Did she pull your hair? Did you end up tearing each other's clothes off and making out on the floor?"

"Seriously? That's your reaction?" I sighed and shook my head, even though I was smiling. "Let's see. No, no, I probably would've liked it, and do you think my life is a porno?"

"Ever since I came into it? Yes."

"You're a douche."

"Admit it, you love it." I didn't think it could be possible, but I swore I could hear that cheeky arrogant grin through the phone.

"So then I tried using this pick-up line that David had given me."

"And that would be?"

I cleared my throat, embarrassed that I had even used such a phrase. "Nice shoes. Wanna fuck?" His laughter was so damn loud that I had to hold the phone away from my ear.

"I'm going to have to try that one sometime. I knew I liked Dave."

"So I spotted two dudes," I continued. "But it turned out that they were gay…or bi, but either way, they weren't interested in me joining or watching them make out."

"So that's why you want to fuck two dudes at once."

"No, I'd want to be greedy and have the focus on me, but I do get a little excited watching two guys together. Anyway, I went to go sulk at a table when some dude named Chad started talking me up and within a few minutes, he was asking me back to his place."

"So why didn't you go with him?"

"I did. But when we got to his place, I couldn't go through with it and I had the taxi take me home. It just felt wrong to me. I know it's just supposed to be random sex with someone I'll never see again, but I don't think I liked him very much. I'm going to try online dating instead so that maybe I can get in another friends with benefits kind of situation. I want to go with quality over quantity."

"That sounds cool. Promise me this, though. I'm gonna visit in a few weeks. That Wednesday night, go out with me and let me coach you on picking up a guy. Hopefully with me around, you'll feel more relaxed and gain more confidence so that when you do meet up with some guy online, you don't fuck it up."

"Alright, it's a deal. Just don't make me regret agreeing to it."

"I'm going to help pick out a guy for you to bang. In what way would you regret that?"

"Do you not hear yourself sometimes? You are so weird. Anyway, Dave should be coming up soon to help me with the profile, so I'll talk to you later, Jon." We said our goodnights and hung up.

"Come on in!" I called out when I heard a knock at the door.

"You know, I think this is actually the first time I've been to your place in the time I've known you," he stated as he looked around.

"Really? Not even for a Walking Dead and ice cream marathon?"

"No, not even for one of those. And be honest. You wouldn't share the ice cream."

"You got me there. I do love my mint chocolate chip. I honestly should tell Minty that we need a break," I said as I rubbed my hand over my stomach. "I might need to trim up a bit if I want to reel in the metaphorical fish in the sea."

"El, you are beautiful just the way you are. So shut the fuck up. Now hand over your laptop and let's get this bitch started."

He snatched my computer away from me and opened up one of the more popular dating sites in a new tab.

"Okay, so first things first. You need to think of a username. Try to come up with something while I start filling out your basic info."

Drat. I was never very good at coming up with internet names. In high school and early college, I had used that generic kind of handle, like "cutegrrl" with some number because I'm not original, but I assumed that it probably wouldn't be a very good idea to use something like that now. Not only is it not appropriate to my age or who I am currently, it would also probably attract a certain creepy kind of person that I didn't want.

"Alright, your basic info, like gender and age and all that shit is done. Do you have your username ready?"

"Um...how about something like Secondchances and then some random number." David stared at me silently, blinking. "You know, cause I'm divorced and this is, like, my second chance in the dating world."

"Yeah, I get it, El, but that name is terrible and I'm ashamed of you. You can do better than that."

I let out a frustrated groan. "I suck at this kind of think, man."

"Okay, how about this then?" He typed something out and then turned the laptop to face me.

"Hotandwilling4u?! What the fuck, Dave? No no no no no!" I rapidly pressed the backspace button while Dave laughed so hard that he had a coughing fit.

As he caught his breath, he calmly replied, "well isn't that the kind of relationship you'd be looking for? I just want you to advertise yourself properly."

"I hate you."

He grinned at my deadpan expression and then grabbed my phone from the nightstand. "How about we ask Jon for his input?"

"I'm not sure that's a good idea..."

"Hey...sexy..." he began to say aloud while he typed.

"What? I never call him that. You're being stupid, give me my phone back!" I grabbed for the phone and he kept moving it out of my grasp as he continued to type out the Text. We looked like a couple of children.

"What...should...my...online...dating...username...be? Smooches,...Your...baby doll. Sent!"

"My hatred of you is getting closer to loathing now, buddy. I don't fucking talk like that." The phone buzzed back with his reply almost immediately. Dave looked at my phone and he laughed so hard that he couldn't breathe. I sighed and took the phone from him when he handed it to me. "Cuminmywetpussy?! Seriously, you guys suck." I texted back to Jon that he was a fucking asshole.

I thought for a moment and was suddenly struck by an idea. I typed it into the username space and turned the laptop back to Dave. "How about this?"

"Barwench1859. I can get behind that. It's kinda cute and it does fit you decently. The number is just this street address, yeah?" I nodded. "Alright then, now we just need to write something about you. Don't worry, I got this, and I promise I won't be a dick about it."

He began typing, surprisingly fast, like he knew exactly what to say without really thinking about it. I was glad that he knew me so well, but also afraid at what he could be saying about me.

"Hey, while I'm here, could you grab me those DVDs I lent you months ago?"

"Yeah, no problem." I moved over to the TV and bent over to rummage through my movie box. I found his DVDs quickly, but before I turned around, I hear the shutter noise on his phone.

"That'll make a great profile picture," he said.

"Are you kidding me? David! Did you just take a picture of my ass?" I spun around to face him with a look that was a mix of angry and horrified. "You can't put that online!" He just laughed at me.

"I'm kidding, I won't use it! Do you have any good pictures of you though?"

"Yeah, there's some in a folder on my laptop. Objectively, they are all very nice, but you can pick the one to use because I'll just find something wrong with them like chicks often do."

He spent a few more minutes uploading the photo and finalizing my profile. "Would you like to look it over before I submit it?"

"Definitely. After the jokes you've made tonight, for all I know, you just wrote "I need dick" in the text box."

He handed me my laptop and I read through what he wrote:

I'm a young attractive woman who can mix a hell of a Long Island Iced Tea. I'm often hard on myself, but if I just listened to my friends, I'd realize that I'm pretty awesome. I love wrestling, perhaps a bit too much, but if you tell me it's stupid, I'll dropkick you in the face. I'm not particularly adventurous, but if hanging out and marathoning Breaking Bad while eating pizza and then getting frisky in between episodes sounds like your idea of a great night, hit me up and let's chat.

I smiled to myself and hit the submit button. I closed the laptop and leaned over to kiss David on the cheek. "Thanks, man. You're a really good friend."