Urban dictionary defines a side n***a as basically a man who wants to be with a female, but can't because she's in a relationship already so all he can do is just flirt, talk and do sexual things with her on the low. I should start off letting you guys know my love and sex life isn’t the life I chose, this life chose me. If I had it any other way, it would be very traditional. I would be a virgin waiting on his wedding day to have sex and be with only 1 woman forever but that’s not the cards I was dealt. From my first kiss to my first relationship, I always find myself dealing with girls who were “technically” in a relationship. Never by choice, I just attract women who are already taken. I don’t know if they see something in me that they don’t see in their man, if it’s just boredom but the women I have flings, one night stands or become friends with benefits with usually have a dude they call their own.
Prime example, a few Halloween’s ago I was invited into a party. I was too cheap to buy a costume so I threw on my twin brother’s chef jacket, a hockey mask and carried a fake bloody machete (a prop from one of my horror shorts) and called myself the “Killer chef”. A group of us went to the party in costume and the party was lit! I didn’t expect my boy to throw an actual party party but he pulled it off. There was women everywhere, drinks of all kinds and he decorated his place like a set of a Blumhouse horror movie. It was on point! So I’m sitting on the couch with a group of other people who came to the party. Cat woman, The Wolf man and Freddy Kruger to be exact. We’re taking shots, joking and laughing non stop and telling each other our own horror stories over the loud music when “Erykah” comes in. I didn’t know who she was at the time or the guy she came with so I had no clue their relation to anyone in the party. I just remember how they stood out. Not just because they came to a Halloween party without costume but because shorty was stacked! You know the song “Brick house” by The Commodores? I swear the moment she walked in, time slowed down and that song started to play. Shorty was built like one of the girls you would see modeling in “King”, “straight stuntin” or some of the other urban male magazines I used to buy before the internet became my source of all info and entertainment. Butt so big, you can see it from the front. Long jet black dreads, wide hips, thick lips and thunder thighs... but she came with someone so I pay more attention to the conversation I was already having with the group (plus I tend to stare when I’m under the influence).
As we somehow go from horror movies to anime in our drunk ramble-ton, they make their way through the party. As the guy said what up to my boy, I realize they knew each other from the army and the girl was his date. “Ah, she’s a dub” I told myself (meaning she’s no one to go after). Eventually they grab some drinks and somehow made their way onto the couch and join in on our conversation. I introduce everyone in character including myself as “killer chef”. Erykah ask where that character was from. I told her I made it up. Wanted to be original (and cheap). She thought that was cool being creative enough to make something up instead of coming with no costume at all (yeah, she was definitely throwing shade at this dude). I brought them up to speed to the conversation we were having (is “The Boondocks” considered anime or not). The guy was totally uninterested in the conversation. “I hate anime!” He declared “that shit is weird”. I shrugged. “Hey man, to each its own” I responded “I’m not a fan of anime myself but it’s a cool art form. You telling me you never enjoyed an anime growing up? No dragon ball z? Pokémon? Sailor moon?” (Literally the three anime shows I watched my entire life up to that point). “Yeah, don’t be so closed minded” Erykah tells him. As everyone begins to list their favorite anime, I walked away from the couch to get a drink. Plus I peeped what was starting to happen. This tends to happen a lot. Sometimes while hanging with a woman and her date (her boo, her man, whatever) I would catch her mentally comparing us. It’s why I no longer bring up that I create online content, make movies, write books, (etc) because once I present my lifestyle to certain people, you can see when the guys ego start to get in the way and he starts to become insecure and once he does something trying to seem bigger or “manlier” or starts to get physical with her unnecessarily (like randomly grabbing her butt or giving her a random unexpected kiss) she starts to compare us. It’s in the eye Chico, they never lie. So I pour myself a cup of warm whiskey fireball cider and start a conversation with the crowd in the kitchen. We’re cracking jokes and laughing our asses off when Erykah walks into the room. She asks me to pour her a drink and I do. She asks for my real name and we get to talking for a bit until I realized we were the only two left in the kitchen. Not trying to be suspect with my friend’s friend’s girlfriend, I tell her “let’s go back to the party, I’m hungry!”
We head back to the party and I start to ask about food. All this weed, women and drinks but he didn’t think about food. So I announced “ let’s order pizza” and started collecting funds from everyone (we ordered 7 different boxes of pizza that night). Everyone dance, got stupid drunk, sang karaoke and made fools out of ourselves, I found myself smoking alone (which I tend to do while I charge my social battery). Erykah walks over to me and begin to compliment me. From my creativity to my ability to hold a conversation and bring people in it and not make them feel bad about the things they like and how impressive it was to get everyone together to pitch in for pizza and deal with all the orders and got everyone singing karaoke as we waited. I shrugged. “It’s party, what else is there to do but to make sure we’re all having a good time”. She smiles at me. “You’re a cool guy” she tells me, “we should hang out”. Now sober me would of just gave her my social media but drunk me was like “fuck it, take my number”. My phone died during the party so I couldn’t take her number but my drunk logic was “if I didn’t reach out to her, no one can say I was trying to steal his woman. Can’t reach out to her if I don’t have her number”. She told me she will text me so I will have her number when I charge my phone. I said cool and kept it pushing. They left the party early and we said our goodbyes. I honestly didn’t think I would speak to her again. I give out my number a lot and I don’t always get a text or call back. We usually just become another number saved in our phone but never use and end up forgetting about until we go through our contact list and go “who the hell is this?” I was able to charge my phone before leaving the party and the first text I get is from her, telling me how much it was a pleasure meeting me. I told her likewise and asked her to let me know she got home safe. Phone dies right there.
The next morning, I’m sitting on the toilet recovering from my hangover when I turn back on my phone. As soon as it turned on, a message came through. Looked like She responded immediately last night and thank me for asking if she got home because apparently her date never made sure she got there safely. I tell her that sucks but she made it home and that’s what important. For the next 2 weeks we begin texting each other daily. She was also in the army but unlike her man, she wasn’t friends and didn’t serve with my home boy. She tells me she wasn’t really feeling him anymore. She got with him cause he was supposed to be stable, coming from the military and was almost 7ft tall, had rock hard abs and huge muscles (which confused me cause I was 5’9 with no muscle and a gut but for someone reason she wanted to talk to me) but his insecurities, his lack of discipline and no sense of creativity or adventure was turning her off. She hated he only spoke in slang/Ebonics and that he was uneducated for someone who went to college and wasn’t interested in learning anything new. She stayed with him because he paid the bills and live on the same army base but she considered him a boring loser with no substance. I asked her if maybe she was being hard on him, she said no. At first the sex was good between them but it stopped being enough in the long run. Muscles and good dick wasn’t enough to keep her attention. I hit up my boy to see if he was close to the guy she was dating. He said “fuck na, I barley know the nigga. We was just cool during our time in training. He ain’t the homie”. After he told me that, I felt like I had the pass to smash. She started to become a fan of mine and read my erotic novella, watched my digital feature and web series and listen to my podcasts. She told me she would listen to me as she fell asleep and how she was so curious of how my brain worked. She loved my sense of imagination and my ambition to build a entertainment empire, practice group economics and rebuild my community really turned her on but she had a man and she wasn’t going to leave him for me, which was cool. I told her I’m down with just being friends.
So a week later, I believe it was either the week before thanksgiving or Black Friday the following week she calls me and ask me what I was doing. All I was doing was smoking weed and playing grand theft auto 5 with my boys. I told her “nothing, what’s up?”. She tells me she’s going to be around my way and she would love it if we could hang out. Shes going to buy a bottle and she asked me what I wanted to drink. Only one thing came to mind. “Oh she’s coming over here to fuck!”. I told her I didn’t want to drink any hard liquor cause I had to travel in the morning so we decided to drink a case of blue moon. She came to my place in this thin lace black dress that splits down the middle, revealing those thighs and hips. As she walked towards me, I watched as her hips rocked side to side, watching that ass jiggle from the front, I had to think of any and everything to get my erection to go down. Knowing what time it was, my boys left immediately to give me and her some alone time. So here we were. Alone in my room, drinking bottle after bottle of blue moon until there was only 2 bottles left. She sat on my bed as I sat on my futon. She asked me why I was sitting so far so I got close to her. She tells me how happy she was that I told her to pull up, I remain nonchalant about it saying “yeah, we’re just two adults having a few drinks. Nothing wrong with that”. She nods her head and looks at the tv. She then lays down on my bed with her backside facing me and all I’m seeing is ass and thighs. She looks back at me and says “would you mind giving me a massage?”. Part of me was still being naive. Na, it’s just a massage. Don’t think nothing of it. So I begin at her shoulders. “Lower” she tells me. So I go low. I’m now massaging her waist when she tells me to be a little more gentle since I was a little too rough. As I continue to massage her, all I can see is her ass and thigh rocking back and forth. Her skin was so soft and she smelled so good, I almost didn’t even hear her when she asked me to go even lower. So now my hands are all over her ass and thighs and I am rock hard!
I promise you I was never soo hard in my life! You could axe down a tree with how hard my dick was. She must of felt the bulge because she turned over immediately, wrapped her legs around my waist and pulled me closer for a kiss. Before I knew it, the lights were off, condom was on and I had the tv volume on blast, trying to drown out the noise of our slapping flesh and her loud moans since I had family home that night. This was the moment I learned big girls can really take dick. They can take dick for hours if you can keep up with them. I’m so used to dealing with small petite/thin women who tap out in the first 30-40 mins during sex but not Erykah. She came to play! Every position I wanted to do, she was down for it all. Missionary, doggy, leap frog, she was down for it all. I under estimated that ass as well. I thought I could take it but that booty was a work out! Her ass was soo big, I double the amount of strokes I usually do to make sure she can feel me in her hitting those walls. Now I’m not the biggest man of them all but I’m above the average dick size and even with my size (I used to lie and say it was 10 inches but it’s really 7 and a half inches...8 on a good day if I’m not drinking or smoking), even at that length I had to power drive into that coochie to make sure she can feel every inch cause that Booty pushed me back every time I stroked into it. I was going soo hard to bust a nut that night but it wasn’t happening for some reason. We went for hours with her climaxing several times but I could never reach mine. She ask if I was alright and if I was enjoying myself. I was. I was also out of breath. The sun was coming up and we both had work in the morning so I ended up just passing out inside her. The next day she called me to tell me how she could still feel me inside her but couldn’t be on the phone long cause her man was in the shower. She wanted to see me again. This time she wanted me to come to her place. She lived in a area 90 mins away from me. I wasn’t down for that trip but she told me she would make the trip worth it. I didn’t believe her but she did. I came to her place and just like before we went for hours but this time, I nutted all over her couch. She drained me out that night. It’s probably one of the best nuts I ever had!! I had her every where. On the kitchen counter, bent her over on the couch, her riding me on the coffee table, I fucked her in every corner of her house until she was K.O. I left not to long after. It was 3am and I could of stayed but I didn’t want to spend the night. I placed her comforter over her naked body as she laid there passed out in the couch. I locked the door behind me and drove back home (which was only an hour drive back). She texted me the next morning and asked why didn’t I spend the night and that she was hoping I would give her a ride to work. I’m like “Na boo, that’s your boyfriends job. You call me when you need other things that your man can’t provide” and that became our arrangement.
She would come over or we would meet somewhere and get busy when she needed a scratch itched. This went on for at least 2 years. She got in and out of relationships with other guys but I was always there on the side lines when she wanted a piece of that Haitian sensation. We don’t talk as much as we used to but she still calls me every now and then. Still getting with dudes she’s unhappy with but they take care of the bills. It’s cool tho. I’m not trying to take the role of the boyfriend anyway. To be honest, the amount of times I had sex with girls in committed relationships, it makes it hard for me to trust or take words at face value. So I guess that’s why I keep on the sidelines. No matter if their boyfriend has more money than me, rock hard abs, big dick and all, they still come to me at the end of the day. She wasn’t the first. She definitely wasn’t the last but I will say she was my favorite one of all. Long story short, I spent more years as a side nigga than I have with real relationships. It’s not the life I chose. It’s the life that chose me ??♂️.
It’s rare that a date or have flings with women with children. I can count at least 2 different situations when I dealt with a woman with kids. One woman had 2 boys and both were half my age. They knew damn well me and their mama wasn’t just “talking in the back room”. We didn’t last long because she wanted a father for her boys and them boys were old enough to be my brothers 😂. Now the other woman was a different story. She wasn’t looking for a father for her kid cause the father was still around. She wasn’t looking for a relationship either cause technically she was in a “committed” relationship (they lived together) but he couldn’t hit it the same way the Haitian sensation could 😏. We had rules tho. Her kid could never address me as “Uncle bla bla bla” cause we not related. I wasn’t coming to family functions, I wasn’t picking Lil homie up from school, I wasn’t taking them to the movies with me... that was her baby daddy and boyfriend’s role. As her friends with benefits, she calls me when she’s upset and when she needs dick. That’s it. I had no problem with that. Especially since she was a thick woman who could go as long as I could. I’ve had woman tap out within 30 mins. Not her. I would be knee deep in her guts for like four hours straight and she wouldn’t tap out. Now of course we would have to take breaks cause we needed to catch our breath but as long as her kid was asleep and the sun wasn’t coming up, we kept going until we drained our body of every fluids possible. I honestly can’t even remember if I ever met her son. I do remember sitting in my car waiting for her baby daddy to leave so I can walk into her place without looking over my shoulders and when I say she was ready, she was ready!!! Was naked under her robe, Bacardi and coke on the table and her son at her baby fathers place. Never ever had to worry about her son walking in. If he’s at her place, I tell her to have her boyfriend watch him and come alone. We need no interruptions. True Story.
It’s finally summer time! Time for summer vacations, summer parties and summer flings! I have a lot of good memories during the summer. A few funny and uncomfortable ones as well. Like the first time I had sex in a car. Must of been summer of 2011. I just turned 21 and got my driver license. I was hype! Told myself I’m never taking public transportation again. Now that I had a license to drive, I was able to pick up my friends whenever and say “let’s go out!” and we could really make moves. So that summer I started to “find myself”. Started dressing up differently, had a lot of money in my pocket and was ready to do things differently than I used to. I didn’t even think how that would catch certain girls eyes because I was too busy living my best life. Now at the time, living in my old building I had a huge crush on a girl who lived 3 floors above me. Since forever I had a crush on this girl and for maybe a year I been telling this same girl about her. Let’s call her “Cheryl”. Now Cheryl I knew for at least 7 years up to the point. We went to high school together, we shared a few friends and recently at that time got reacquainted. She was the homie so I told her about every girl that caught my eye. So one day, I’m walking in my old neighborhood and I’m feeling myself. Got money in my pocket, got brand new clothes and I was writing a new movie I thought I would be filming soon so I was feeling like the man, like jack screaming “I’m on top of the world!” As I’m walking home, I see my crush walking my direction. All these thoughts were running through my mind. Do I say something? Do I say hi and keep it pushing? Do I ignore her? Before I can rationalize these thoughts, she was already 3 feet away from me. “Hey you” I tell her as she locks eyes on me. She smiles back “Hey!”. In my mind I’m lost for words cause I never even thought I would have the courage to talk to her. I ask her “Do you remember me? When we was younger we (referring to my siblings) used to play with you and your brother at the park”. She laughs “of course I remember!”. So here we are, both smiling like idiots. I pass her my phone and tell her “give me your number, we gotta catch up”. She puts in her number immediately. When I say I felt like I upgraded to another level of life.... mannnnnnnnnn I was on a whole new high!!! So I text Cheryl cause at the time she was the only one who I talked to about girls I was really interested in and the last time I spoke to her, she made fun of me saying I would not only not talk to my crush but I also wouldn’t get her number. I text “Guess who just spoke to his crush and got her number.... this guy!”
She lol and congratulated me but something felt off. I paid no mind to it cause I was too excited about getting my crush number. We started texting that night but I wanted to play it cool so I held myself back from reaching out to her back to back. Randomly the next day Cheryl text me and ask me to pull up to her place. She ask me to bring my car and a bottle over and we can play some card games. Now because Cheryl and I always met up with a bottles, some card games and friends I thought nothing of it until she told me it would just be us two. Still thought nothing of it even when she asked me would we be able to push the back seats down (at the time I was driving my mother Chevy suburban). It wasn’t until I sparked up with one of my boys I figured we wasn’t just going to drink and play card games. When I told my boy my plans, he laughed in my face. He said “Bro, y’all bout to have sex”. I’m like “What? Na!” in total disbelief. She’s the homie. We’re not even like that. Now my crush was cute but this girl was gorgeous. She didn’t even need make up to amplify her beauty. She was humble, funny and had a great sense of fashion. She was a very slim/petite woman with long Curley hair, her butt wasn’t huge but it had a cute jiggle and double Ds I couldn’t take my eyes off from but she was still the homie. A few other friends join the cypher, mostly girls and when they hear the story, they all agree.. “yeah you’re about to have sex!”. Me being naive, I tell them they don’t know what they are talking about. I get ready to leave and I get word from my moms I won’t be able to use her car for the night. So I call up Cheryl to tell her and she goes “it’s okay, we’ll just hang in my dads car”. Now the alarm starts going off in my head. “Wow, she really wants to spend time with me tonight? She never so persistent in seeing me... maybe she’s going through something and just want to talk.. fuck it.. just in case... I should bring a condom”. So I get to her place, she walks out and we both quietly entered the back seat of her fathers car. It got really dark really fast to the point I was only able to see her with the street light above us. We were drinking pinnacle vodka, straight no chaser. Taking shots after shots. I don’t even think we ever got to play any card games. I just remember we had that right amount of drinks and the right amount of laughs before it got real quiet. She tells she’s cold, so I wrap my arms around her. She lays her head on my chest and we laid there for about a minute. Without hesitation we found ourselves kissing. At first it was an innocent kiss... but then we couldn’t stop. Eventually she turns around and wraps her arms around my neck. I started pulling her closer and closer as we continue to make our heavy. She tries to wrap her legs around me but there was no fucking space in the back of her fathers Honda Civic. She then looks me in the eye and ask “Do you have a condom?”. Feeling smart about having one with me, I pull it out instantly. I help her take off her pants and noticed immediately she wasn’t wearing any panties. It was that moment I realize how naive I really was and the fact that women know they are going to (or not going to) sleep with you before they even step foot out the house. I try to take off my jeans and put on my condom but I couldn’t get my jeans past my knees because there was enough space to take off my pants completely. She didn’t care. Once the condom was on, she just started riding. Now I’m in complete disbelief. Never in my right mind would I ever imagine Cheryl riding me in the back seat of her fathers car. A man I never met.
So we’re doing it in the backseat of her fathers car and everything was going so well until she started crying. She completely stops riding and just starts crying with me still in her! She gets up off me and goes into the corner of the car and continues to cry. Now here I am, drunk, with my pants up to my knees, dick out, my naked cold ass on these leather seats, condom still on, feeling awkward in the tight space of a car of a man I never met. I didn’t know what to do so I did what felt right. I held her and played with her hair until she calmed down. She eventually would tell me it was the first time she done it in a while and she wanted to do it with someone she trusted. She’s been heart broken by her ex so she had a hard time dealing with other men but once she heard I was finally talking to my crush, she just wanted me for herself. I thought that would be the last time we would have sex but it continued with the following week after leaving the bar and taking the train/Van back (and I ran home in 15 mins instead of walking the usual 30 to get the car while she was still in the mood). We begin to have sex in cars alot. We had sex in the car after she saw the best man holiday, after leaving her best friends party but the last time we did it in a car, it was the last time we had sex period. Literally this time, last year. At this time we were trying to date but it wasn’t working out. She had a heavy case of FOMO and my dumbass looked through her phone and found out she was talking to other guys after she left her phone in my car. So I decided to give her some space and wanted to go our separate ways. We had break up sex at my place the day I saw the messages and I thought that was the end of it, but she calls me one night and tells me she wants to talk things out. I was packing up to leave and shoot the first episode of my travel series in Fishkill New York but I said fuck, I’ll stop by one more time. She ask me to bring some weed so we can smoke as we talk. I get there and her dad was asleep in the backyard so we went back to my car instead lol. I had no intentions of having sex that night. Maybe it was the weed, maybe it was the back to back R&B songs, that right summer night heat and breeze but something came over us that night. In between spliff and songs, we found ourselves all over each other one last time. We made love plenty of times since the first night in her dads car, especially when I moved into a new apartment and she would spend the night but this time, we wasn’t making love. We was fucking. That car was rocking like we were in the middle of an earthquake. We went round for round until we was out of breath and covered in sweat. Looking at each other in disbelief. It was supposed to be over but here we were doing it again. Nothing ever came out of it. We eventually went our separate ways and never spoke again.. but when someone asks me “hey, you ever did it in a car before?”.. I begin to think of those summer nights.