The Wingman

Chapter Two: Sam

So there I was at this bar, cornered by this guy trying to hook up with me. Some nameless weenie I got stuck talking to because of my roommate and her asshole boyfriend. I'm annoyed. Those two are morons. They fight and make up. Break up and make up. She never shuts up about it. It's always drama. They wanted to go out tonight, she hounded me to come.

"Come on! It'll be fun." She pleaded.

So I caved. As standard procedure, these assholes get into a fight the minute we walk in the door then proceed to spend most of the night in the corner arguing. Enter stage right on cue, whatever his name is, "Dan"...."Dave".

I can't remember what he said, I was barely listening.

I tried to be polite and blow him off nicely. Start that walk away method, planning to hit him with a "ok nice to meet you" as I escaped. It didn't work, he followed along.

"Fuck I need a drink!" My brain screamed.

So I make my way to the bar in an attempt to ease my suffering since I can't shake him. I told him I was looking for my friends knowing those dicks probably left already in the midst of their fight.

My eyes wander as he talks. At a glance, a couple stools away, I see this guy sitting alone. He only briefly looked over, but his vibe felt friendly, comfortable. So I took a chance.

I saunter over the two stool lengths, my shadow in tow, and slither my arm around this stranger's arm. I quickly craft my exit by lying my ass off hoping this guy does me a solid. Pretending he's the friend I've been looking for, I was finally able to dismiss Dan/Dave.

I order drinks and formally meet Ryan. We sat and chatted for a while, he actually turned out to be a cool dude. Interesting in those small ways, little details that are fun to learn about a person. And I'm not going to lie, he was pleasant to look at. He had a great laugh. There was a way about it, how it crept in through his words while he was talking and amused with the topic. It was rather cute.

Then it struck me as he was talking, Ryan's handsome. Not in some chiseled Adonis way, he was just an average dude. But in that way someone becomes increasingly attractive through character and personality.

We started talking about music and the conversation just took off making us lose track of time. I had to go get some sleep, but I was digging on this guy. We had a great chemistry and I wanted to hang out more. So I invited him to my spot I like to go to, more of a performance venue. Comedy night is one of my favorites, and he has a good laugh, so why not. I gave him my number before I left.

When I got home I saw my idiot roomie's door closed as I passed by on my way to the shower. I rolled my eyes to myself remembering that situation. "Not a total loss though" I think to myself as I remember that guy I met. Ryan. Hmm, could be fun.

I let my thoughts wander as I soaped myself up. For a seemingly reserved guy, he had some sex appeal. It was subtle. I started thinking about his hands, how they would feel tracing over my body, leaving no inch unexplored. I thought about those lips I watched as he spoke earlier, and thought how they would be so soft on my clit. Mmm, my arousal teased me as the hot water beaded down over my flesh. My fingertips caressing my tender clit, losing myself in these thoughts. I rubbed out the sweetest little orgasm before exiting the shower and slept like a baby.

Over the next few days, I started getting those booty texts from Kyle. Kyle was my "fuck buddy" basically. We get together to have sex when we need some touch. He's an ok guy, nice and all, but I wasn't into much more than what we were doing. It was very routine. I go over to his place, we have sex, often in all the same positions as the previous encounter, he falls asleep. He always cums, I hardly ever do unless I do it myself. There was just a lack of chemistry.

So I get back to Kyle and tell him I'll come by tonight. As per our "routine", we hang out, move into some groping and kissing, then pop into his bedroom to get naked and fuck. The same three positions before he cums. Inside five minutes after he nuts, he's snoring and I'm left staring up at the ceiling debating my next move. I could lay here and just go to sleep, or I could just go home and pleasure myself with my collection of toys. Decisions, decisions.

*Text Notification*

"Hey Sam, it's Ryan. We met last weekend and you invited me to comedy night. Sorry it's short notice, but it's Wednesday, and I'm still interested if you want to meet up."

Hmm, this is a new development. I look at the time, then over at Kyle already balls deep in his slumber with his mouth open sawing logs.

I hit reply and sent Ryan the name of the place telling him I can be there in 30 minutes as I got dressed and hustled to my car.

We had such a blast. We didn't need to drink a whole lot to get comfortable and loosen up. It just flowed organically, the banter and little jokes. By the end of the evening, it was clear we had a standing open invitation to each other's company and the months just flew by cultivating this cool friendship.

Of course I checked him out. All of those casual low key nights hanging out at his place, I noticed how his fat cock flopped around in his sweats, secretly making me salivate. I watched his mannerisms, ogled his body, hung on his every word. He was a delight to be with, a great blend of comfort and intrigue.

Yeah sure, I wasn't fucking Ryan, but his company was great. Our conversations just kept it interesting. We talked a lot about sex, just in general, as if it were the weather. I discovered he had a rather healthy appetite for exploration, many things he'd like to experience. There's definitely a dominant presence, but I can sense he harbors a curiosity as to what it would be like to surrender that role.

These types of conversations were the best. Talking kinks, confessing little dirty thoughts and deeds, it was so freeing. My chick friends are all about "love" and "relationships" and "where is this going" type of chatter. Always trying to define everything. It's exhausting, the continual analysis.

Hanging with Ryan didn't have any of that, it was straightforward. We laughed and ate, keeping it simple. In between, we hooked up with whoever was on our rosters.

He liked to tease me about Kyle, and our relationship. There was never a shortage on the smart ass jabs, "Well, hit me up after you get him all tucked in LOL!"

There was just this unapologetic vibe, we were raw and uncensored with each other. No conversation, detail, or response was unwelcomed. There's not many people I could do that with, not without offending someone with my opinion or its delivery. I enjoyed this friendship's casual way.

One night we decided to go out, I felt like some dancing. He obliged even though it wasn't his thing. I met this awesome chick named Cheryl, we danced a bit and smiled. She was cute, so I asked her to hang out with us and have a drink. We really hit it off, she was fun and flirty. Her comments alluded to her interest in both women and men. Just going where the feeling takes you.

When she leaned in and expressed an interest in Ryan, I decided to meddle. I knew he wasn't interested in a clingy relationship so Cheryl would be good for him. A little hook up person he wouldn't feel guilt about. One night stands can sometimes feel gross due to a disconnect, empty. Maybe they'll have some fun and she'll make his cock happy in the process.

I lean to Cheryl's ear and say, "I think you should take him home. He's pretty dirty, kind of slutty when he wants to be. I think he'd be a fun ride in the sack. Plus, he smells incredible tonight."

She smiles and lets out a little sigh in my ear.

"He's a nice guy too. "You're in good hands." I add.

Cheryl was already diverting her attention in his direction, smiling and blushing.

My work here is done. I make my exit wearing a content smile shortly after our goodbyes, leaving those two to get better acquainted.

After they hooked up that night, Cheryl was around more often. She was a fun fixture when she would go out with us. One night we got into a little girl talk and she shared what Ryan was like in bed. Boy I ate that shit up. She told me about his cock, each word teasing me as I thought back to all those times I'd seen its outline in his pants. She described the moans and man sounds he would make as he came. I became so aroused my panties were moist. Cheryl seemed to be pleased by this, giggling and smiling as she spilled all the horny details.

I'll admit, I couldn't stop thinking about it. The more I learned, the more curious I became. The more I thought about him in a more sexual way, often sometimes so vivid that my pussy became wet taking me by surprise at how fucking thirsty I was. I was having a hard time shaking it.

This one rainy night we went out, I was feeling all sorts of flirty. These naughty thoughts stirring in my head, I decided to tease him and see what happens. I poked fun at his claim to be a sexy kisser. It stung a little bit when he responded back with a "Well you wouldn't know now would you?"

He was right, I didn't know any of those sexual ways about him, not first hand. Just from sharing in conversations. So, I pushed it. Stating that I'd have to be the judge of that.

We made our way through the soaked parking lot to my car, immediately making out upon entry. Fuck it was hot! That sexy wandering hands element which made a body quiver. I could feel his hard cock pressed against me driving me insane. I broke the kiss only to slither into the back seat. I wanted more. Needed more.

He followed and I wasted no time unbuckling and unzipping him. I knew what I wanted, and I was going to take it. I started sucking his cock with such precision, as if I was memorizing it. Learning every ridge, every vein, making every twitch belong to me. His moans were intoxicating, turning me on to the point where I could feel my pussy soaked and throbbing in my panties.

I wanted him to cum. I wanted to make him cum. I could taste his precum on my tongue and it was like a drug. I sucked him harder, until he was about to lose it. He grabbed my head, filling my throat with his warm spunk. His grunting and moans were so filthy to my ears given the moment.

Mmm, I lean back wiping my mouth like a proper slut while he zipped himself back up. The vibe was slightly awkward as we came back to being "us" from that erotic high we were just riding. I lit our joint so we could chill for a little bit, then go back to the bar.

When we got back, Cheryl was there. It's getting late. I have some shit to think about, clearly. So I decided to just bail for the night. Ryan seems a little anxious, I'm sure he has some thoughts about tonight too. I say goodnight and "We'll talk soon."

The next couple weeks, I busied myself with work and just hanging out at home. Thinking.

Kyle hit me up a couple times, but I passed. I may have been having some complicated thoughts about what just happened with Ryan, but it was so fucking hot, it was haunting me. An under the covers hump with Kyle would only fucking tease me knowing there was better dick out there I wanted.

Finally, I broke. I reached out, prompting us to hang out. I wanted low key for sure. Loud music, party clothes, no thanks. We'll likely need to talk, or, maybe NOT talk. Either way, I needed to see him. I missed him, and I was nervous shit would be weird or different.

Saturday, I picked up our pizza and drove over, so anxious as I knocked on the door. When he answered, his friendly familiar smile was inviting me to that comfortable space we have going. Just normal shit, no awkwardness. Even the slight chat about the car BJ was very chill. We seemed to conclude we could have this AND that, navigating a casual FWB and I was so relieved.

We laughed and talked into the night hanging out as usual. I was elated and likely smiling like an idiot. I took a pause and watched him, taking him in before popping up off the couch to get something to drink. Leaning against the counter digging in his cupboards for a glass, I felt his heat against my back. I inhaled his scent and my pussy instantly reacted.

His hands were all over my body, under my shirt, fondling my tits. Then traveling south dipping past the waistband of my sweats, his fingers spread my moist lips to invade my eager cunt.

Like a bitch in heat, my body began to tingle in its craving for that selfish primal need. I could feel his cock so hard against me as I pressed back into him. All the sensations overwhelmed me. Feeling his skin beneath my wandering hands, his fingers expertly fucking me, I barely recognized my own voice almost begging, "Fuck me."

As if I couldn't be anymore turned on, he pulled his fingers from my dripping cunt and sucked them clean. It drove me fucking crazy it was incredibly hot. I was blurred with lust as he pulled off my shirt, pushed me into the countertop, and pulled my pants down. I felt so exposed. So anxious with anticipation as he fondled my pussy with his fingers again, then slid his cock through my slit. What a fucking tease. I reached down to guide him inside, I wanted that dick. As he filled me, my body contorted and arched.

He started fucking me faster, his hands pinning mine to the countertop, growling his confessions of how he's been wanting this. I feel him ready to cum, I can hear it in his voice, in his breathing. When he tells me, I stop him, make him hold back.

I want more. I want to tease him and make him lose his fucking mind. Take over all control of his body, owning his orgasm. Making him a vulnerable mess for me.

We make our way back to the couch and I mount him. Kissing him. My hands could not stop touching his face and body. The feel of his warm skin, the hair on his chest, the roughness of his beard. I grinded my wet cunt along his shaft and felt how turned on he was, how he couldn't resist reaching for my pussy. But I can't allow that, not this time.

I forcefully tucked his wrists under my legs, pinning them down, leveraged myself with the couch back, and drowned his cock inside my pussy. I couldn't go slow or soft. I had this need to ride his cock to that edge, make him desperate for release, becoming a slave to my pussy. I grinded down deeper, shoving my tits in his face. His mouth sucking my erect nipples between his whimpers.

Again, I hear his breathing change. He's going to cum, and very soon. I needed to hop off and give him a break, a little denial to add to the tease. I positioned myself between his legs and softly sucked him. Slowly bringing him back from that edge. He reached for my hair, a reflex attempt to take control. So I held his wrists against his legs, then proceeded to perform the deepest sloppiest hands free blow job.

Fuck, his sounds were phenomenal making me want his cum.

I became so excited, I needed to feel him inside me again. I climbed into his lap, returning his hands back to their spot pinned under my legs, leveraged my weight on my knees and pounded down on his shaft.

I pressed my chest against his body, my mind lost in the rhythmic bounce of my twat. My moans filled the air, I could feel my climax pulling me. Suddenly, he pulled his arms free, wrapping them around me, thrusting his pelvis up, driving his cock harder and deeper inside me. Like a jack hammer, violently pounding me to orgasm. My body surrendered, making me a quivering mess, my whispers were begging him to cum too.

His embrace around me tightened and his breathing became labored when moaning out as his orgasm ripped through him, convulsing and filling my pussy. It was intense, I've never experienced anything like it. Our exhausted bodies, sweaty and tangled, now needed rest.