The Sinful Six Chronicles: Lolli Part 1. A follow up to "I'm a legitimate motherf*****" | 2016

I never realized how expensive dating Lana was until I saw how much money was still in my bank account the Monday after getting paid. Spending over a year with someone really leaves you with uncertainty about yourself. I always equated it to Captain America thawing from the ice. I didn't know if I still had "it". I was rusty. Lana and I got to the point of getting overly excited about new movies on Netflix. Who knew if I can could still talk about anything single people cared about?

I got tired of sitting at home on online dating sites where I had time to formulate a compelling impossible to ignore message instead of being a part of the real world. I reached into my closet and pulled out my favorite shirt from my single days. It was a military style navy blue double breasted pocket button up. It had brought me so much luck and was guaranteed to be tangled up with someone's bra and panties every weekend.

I got it ironed out and rubbed my hands just itching to feel the power of my magic shirt. When I put the shirt on I felt nothing but dissapointment as the bottom of my shirt didn't pass my belly button and felt more like a corset.

With the money I had been saving since Lana's absence, I decided it was time to update my life to better align with where it was going. I bought one of those fancy smartwatches, got a haircut, new shoes, and a new wardrobe. I was ready to start my next chapter in my life.

I met Lolli about a week or so before Lana and I split up. She was plus sized with amber brown hair and forest green eyes. She had wide curvy hips, supple breasts, and an absolutely beautiful face. I was at a resturant with a couple of my male coworkers after a long day at the office. She was with a married couple at a booth across from us. I kept catching myself tuning in and out of the ongoing conversation to glance over at her. She was near impossible to stop looking at. I had decided after Marie and I's final encounter that I would remain faithful.

"Bruh!" My coworker Chris said as he waved his hand in front of my face. "Good. You're still alive. What the fuck do you keep looking at?" He asked as the other guys snickered at the table. "Homegirl at 12 o clock" my coworker Tyreese answered as he sipped from his beer bottle. Chris turned around to check her out. "Jeez man, this is why you can't a close a deal. You don't know how to play it cool." I said to Chris. "Okay stroke face, please teach me about playing it cool." Chris retorted. Tyreese laughed. "You guys are stupid and Chase don't you have a girl?" Tyreese asked. "Yeah. Doesn't mean I can't look. Now.." I began before Chris interrupted. "No no no no, I'm not done with this yet. If you think I can't close a deal, why don't you show us what you got big man?" Chris challenged. "I'm here to spend time with you assholes, not give you lessons on how to talk to women." I said trying to get out of the situation. "Go get a blowjob. That's all I'm asking." Chris pressed on. "I'll talk to her. That's it." I sighed. The married couple had gotten up to do kareoke as she stayed at the table. I made myself at home by sliding into the booth facing her.

"And here I was thinking you were just going to keep looking at me all night. I guess you figured you would have to talk to me to get that blowjob." She smiled. "You heard that huh?" I smirked somewhat embarassed. "Every word. I'm Lolli and please if your next move is to ask me how many licks does it take, keep it. You would be the 100th guy this week." She quipped. "I'm Chase. You just stole my best line so I guess I'll have to talk to you like a normal person." I smiled as we shook hands. Lolli's hand was extremely soft. We probably held each other's hands a little longer than most people but I instantly felt a connection to her.

Lolli and I talked for a while. So long in fact, that I didn't realize that Chris and Tyreese left. I learned Lolli was living in a less than ideal situation. Both of her parents had been in a car wreck making them both unable to work which put the pressure on her to be the breadwinner. Lolli also confided in me that her parents had become mentally and emotionally abusive since the accident often times guilting her into staying home, hindering her social life.

When our night came to an end and we were outside, we embraced and I used her phone to add me on Facebook. I could have gotten her number but I figured it would be less suspicious as Lana knew I would add customers I sold to on Facebook rather than get their cell phone information. Lana had deleted her facebook so Lolli really wouldn't know that I was in a relationship. Lolli and I had conversated back and forth during the final week of Lana and I's relationship. It was nice having someone around to make me forget about Lana and I's petty arguements. Here I was now with my thumb hovering over the "Message" button as a single man ready to get my new life started.

We decided to go to one of the local bars for drinks and talk

Under different pretenses. Today ended up being Lolli's birthday and she had originally planned on sitting at home. Lolli and I had set the boundaries before hand on what our situation was: Whatever happened would happen but I wasn't ready for anything serious. Lolli agreed as she too had just gotten out of a serious relationship.

Lolli looked amazing. She had straightened her hair and wore in down instead of the bun she had the first time we met. She had "dolled up" with fire red lipstick on her lips and her makeup expertly applied.

She told me how much she loved Cinderella and how she found comfort in it when her parents would take their frustrations with thier disabilities out on her. "It just helps me to think that my own prince charming is going to come along and rescue me someday. Until then, I guess I'll have to settle for guys like you." She teased by sticking her tongue out. I loved Lolli and I's back and forth. I never was able to have that with Lana. Lana was usually so young and sheltered that you had to watch what you said to avoid offending her.

The bar was getting too crowded so we went out to the balcony outside where we were oddly by ourselves. The tension had been mounting for a while now. I grabbed her Blue Motorcycle drink and put it on one of the tables before passionately kissing her. She responded in kind by placing her hand behind my head pushing herself against me. I lightly bit her lip each oppurtunity I got.

When we had finally finished our kiss, I noticed the waitress had been standing there akwardly waiting on us with our bill. Our bill was $63.37 for our combined 6 drinks. Not thinking with the head on my shoulders, I handed the waitress a $100 dollar bill and asked her to keep the change. Lolli laughed slightly embarassed before grabbing my hand and leading me to her White '96 Jeep Wrangler Sahara.

We laughed and talked about the situation as I secretly beat myself up internally for spending so much money on just alcohol and tipping our waitress who had maybe checked on us twice forty dollars. "Come back to my place." i instructed her. "I don't know. We both just got out of serious relationships. It might just be too soon." Lolli said conflicted. I had experienced this kind of last minute resistance plenty of times in the past and I knew the best move was to back away as pushing only would make me appear like any other guy she had met and totally throw off the dynamic. "Yeah you're right. You probably would catch feelings anyway." I said with a wink before kissing her cheek and turning away. I began counting my steps. 1...2...3...4.... "Wait!" Lolli called out. "Usually they only let me take two steps before stopping me. You're making me hold out a little." I said with that cocky fucking smile I had developed. "I'll follow you. You better be able to do better than that kiss though if things happen." Lolli said. "Don't worry. They're going to happen." I said casually.

Lolli sat on my bed still trying to debate what she was willing to do. "I'll suck your dick. That's it. Got it?" Lolli asked. We began to kiss again. I could still taste the Blue Motorcycle on her lips as she slowly laid down allowing me on top of her. I kissed her shoulder blade slowly moving up her neck and to her ear. Lollis legs straightened as stiff as if she had been struck with a taser while I flicked her ear lobe with my tongue. I raised up and we both peered deep in each other's eyes.

Lolli pushed me off to her side and undid my jeans. She began stroking my cock and blowing her hair out of her face. I grabbed it and held it in a ponytail position as she began to slide her soft puffy lips up and down my shaft. Lana HATED giving blowjobs and would complain about giving them. Lolli had a hunger, a craving, for oral pleasure. Lollis hands would stroke the base as she sucked the shaft and swirled her tongue around the head. I was in heaven. I could see the look of "Yeah motherfucker, I know you like it." All over her face. I sat up on my knees as she laid on her back and began to skull fuck her. I could hear Lolli moaning and trying to suppress her gag reflex as I fucked her mouth with the same verocity as I would her pussy. I began undoing her jeans as well and playing with her clit as she moaned louder. Lolli was soaking wet and had been for some time. Lolli spit out my cock and moaned extremely loud as my fingers penetrated her. Lolli pulled off her jeans as I placed my head between her thick lucious thighs and began to lick her clit. My fingers reached deep inside of her and curled up to put as much pressure on her gspot as possible. She screamed with pleasure and gave me the impression she was going to climb the walls as my tongue and fingers moved in sync on her soaking wet pussy.

Lolli began to shake as a plane during turbulance. I picked up my pace as she tightly pulled at my hair. Suddenly she let out a high pitch scream as I felt something begin dripping from my chin. I looked down

and saw as her muscles tightened and cum spewed from her pussy over and over. "I'm sorry. I squirt alot." Lolli said. "38. The answer is 38." I said. "What the fuck are you talking about crazy?" Lolli replied. "38 licks to get to the cen.." I said. "Shut the hell up" Lolli said interrupting me and laughing hysterically.

I was fully erect and spread Lolli's legs attempting to penetrate her. "Wait. I have only had sex with one person. You're going to be my second." Lolli said. Even though it was explicitly said, I knew what she meant. Lolli was trying to express how she considered this as being special. This wasn't just her typical Saturday night. The only other person she had given herself to was her ex who she had recently broken up with. She needed me to understand how special she viewed me and the risk we were taking with our friends with benefits situation.

I slid inside of her going as deep as I could reach. Lolli felt so tight. I raised her leg's up as I began to thrust. Lolli had no control of her legs as she had given into the intense pleasure coursing through her veins. I pushed Lolli's knees into her chest as the head of my cock continuously pounded against her gspot like a battering ram. Lolli covered her mouth with her hand to muffle her screams. I ripped her hand from her mouth forcing her screams to travel through the house. I held both her hands as I put everything I had into short calculated thrusts.

"Get on top of me." I instructed her. "Um I don't do that." She replied. "Have it your way." I said as I grabbed her leg and dragged her on her stomach to the edge of the bed. I gave her a hard slap across her ass which she wailed in a mixture of eroticism and pain. I took my left hand and wrapped her hair tightly around her wrist and placed my right hand around her throat as I entered her anxiously waiting pussy again. I continued with short and powerful pumps as deep as I could as she bit her lip trying to conceal her screams. Lolli gurguled as I tightened my choke. Lolli reached back and dug her nails into my arm as she got closer and closer to euphoria. When she finally reached the point of no return she pried my hand from her throat and let out a long wail as she squirmed and shook in ectasy.

Lolli used her foot to push me and create some distance as she crawled to her knees. She ripped off my condom and gave me this testosterone pumping, heart pounding look as she sucked solely on the head of my cock. I proceeded to cup the back of her head and slide my cock into the back of her throat over and over again. My knees got weaker with each thrust until finally shot multiple spurts of cum trickling down the back of her throat. Lolli removed my cock but continued to stroke as she tried to maintain her composure.

After we had wrapped everything up I went to the bathroom to clean myself up. I quietly pumped myself up as I stared at the reflection in the mirror. "Look at you! You got right the fuck back up on that horse and nailed it like it was another day in the office. Who's cum is all over that bed? Her cum! Why? Because you fucked the living shit out of her!" I remember telling myself.

Once I had finished, I opened the bathroom door to Lolli who was walking past. "Hey where are you going?" I asked confused thinking she would be spending the night or at least be up for another round. Lolli turned around and pulled my face to hers kissing me as if to carry that feeling with her if we were never going to see each other after tonight. Lolli eventually let go and walked to the door. "No feelings right?" Lolli asked. "Right." I said as if I was unsure. "Goodnight." Lolli said as she gave me a wink and a smile before closing the door behind her.

"Goodnight"