The Wingman Ch. 01

I was at this bar with a couple of co-workers having a drink after work. The bar scene isn't really my thing, so I had planned to only stay for a couple. My eyes wander the scene for some people watching.

I notice briefly a couple stools away, this girl getting hit on. Standing with her back to the bar, I sense he's invading her space. She looks as though she's uncomfortable, trapped into talking to this guy. She moves to gain space, claims she's looking for her friends she came with. At this point, I turned my head away trying not to eavesdrop.

Suddenly, I look over as I feel someone nestled up against me, feeling a hand reach underneath my arm which is resting on the bar, then glide down my forearm, coming to rest on my left wrist.

"Oh, you know, I just found my friend, so..."

The woman lies, trying to use me in her escape.

As she gestures, looking over at me and in seeing the situation, I say,

"Oh there you are, was the line for the ladies room that long?"

"No, I just got caught up talking on the way back." She responds, then turns to the persistent stranger to dismiss him.

"It was nice to meet you, take care."

Then she turns away from him back to me without waiting for a response. So he leaves.

"Thanks." She simply said as she pulled her hand back and signaled the bartender for a drink.

"Some guys just can't take those subtle friendly hints, that we're just being polite." She adds.

"Hey no problem, happy to help." I say.

"I'm just going to chill here for a minute to be sure the coast is clear if you don't mind." She says.

The bartender comes over for the drink order.

"I'll have a Draft. And bring him another round of whatever he ordered please."

She says motioning in my direction.

"Thanks, that's nice of you." I respond.

"You're welcome. It's the least I can do, that guy would've never gone away otherwise, so I appreciate you playing along."

Our drinks arrive. I raise my glass, and she mirrored the gesture.

"I'm Ryan by the way."

"Samantha..er Sam." She replies.

We sat and talked for a while, sipping our drinks. The standard 'get to know you' small talk. Discussion of music came around, and the conversation just flowed so easily. Touching on genre, concerts, and specific works made it so effortless given the common interest.

I mentioned that I enjoy playing guitar, just a hobby I toy around with.

Sam offered, "You know, I sometimes go to this little spot that has amateur night for local performers. It's really a fun time, with a great supportive vibe. Depending on the night, there's singer/songwriter performances, poetry readings, that sort of thing. Might be something you could check out."

"Even if you didn't want to perform, the environment feels creative and inviting anyway. Very low key." She adds.

"Well Ryan, I have to get going, but it was great to meet you. And thanks again for letting me rope you into my fib." She smiled.

"I'll be going to comedy night this Wednesday if you're interested. It's really fun. Maybe you'd like to meet up." Sam finishes with a shrug.

As she spoke and described the event, then ultimately invited me to tag along, I watched her. The movements of her hands while she talked, the curl of her lip when she smirked. I was actually a bit taken by her. Sam is attractive, but in such a way that she might not even notice it. She's just being herself, I found it intriguing.

Earlier, the way she had twirled a lock of her hair around her finger while scanning the room watching its patrons. She had this way about her that felt very relaxed, casual. A chill vibe that carried no expectations of me to entertain her. Many women are not this way, but rather need to be the center of attention and needy. Sam was nothing like that. Right away, there is a comfortable space to just be in her company.

"Here, I'll give you my number and you can shoot me a text if you want to grab a drink." Sam says reaching for a cocktail napkin to scribble her phone number on.

She slides the napkin over into my space on the bar and stands up putting her jacket on.

"If you decide it's not for you, that's cool too. I won't take offense if you don't join me." She cracked a smirk, placed her hand on my left forearm and said, "Later man."

She turned to make her way toward the exit, and I watched her until she disappeared amongst the sea of people.

As the months moved forward, Sam and I hung out quite a bit. She became that person I'd text when I wanted to go do something but wanted some company. We were really into food. So trying a new place to grub was common practice.

Interactions with her were always a good time. A couple beers here, hanging out smoking some weed there. It was all so casual. I liked that it carried no expectation. Even when she would come over to hang at my place for a movie night, I didn't feel that twinge of awkwardness as if it were a date. She would typically come in her comfy threads, often wearing no bra, completely relaxed. Occasionally, she would fall asleep on my couch for the night.

Naturally as things moved along, we covered many topics within our conversations. We seemed to be very comfortable discussing sex and various details about it just as any other topic. We talked a lot about kinks and our sexual preferences. What we like, might want to experience, and of course those limits we all have as well. I found her so easy to open up to.

It was pretty cool to be able to talk about those things without judgment and get a female perspective. She never held back even if her thoughts would ultimately paint her in a bad light or make her appear to be raunchy. She embraced that part of herself.

Sam was a great wingman when we went out. She even got me laid once.

Some random occurrence where she met a girl while out on the dance floor. Since she's so outgoing and makes friends easily, she invited this woman Cheryl to hang out and have a drink with us.

The three of us drank and talked into the night, until Sam decided to head home.

She whispered something in Cheryl's ear, making her blush, smile, then look up at me, finishing her conversation with a "you're in good hands" comment and a smile.

I pulled Sam aside and asked if we should go together. Make sure she made it home ok. She rolled her eyes in that fashion she does when I'm being ridiculous and assures me she doesn't need a sitter.

"I'm a big girl, I've already ordered an Uber." She replied.

"She's a cute chick, and she's into you, just let it happen and have fun." She said with a big smile followed by our little hug goodbye.

She turned to the exit to make her way out while I watched her disappear through the crowd.

Over the next couple months, I saw Cheryl off and on when schedules worked out. Sometimes for little dates or hooking up.

When it comes to the women I've pursued during our friendship, Sam liked hearing about the sexual aspect. She's rather dirty and delights in the erotic facet of connections. Of course, I oblige, taking part in an opportunity to brag since Sam is like a bro.

Different times we've shared the sordid details of our intimate encounters with others, it was always received well on both ends. Rather sexy in its own little way. I could tell she was turned on when hearing of some hot sensual foreplay with a random I hooked up with. Then, I teased suggesting I'm an intense make out partner.

Flirtatious playful comments regularly sprinkled into our confessions made it fun. Playing jump rope with that friendship line has been quite tantalizing.

One evening while we were out having some drinks, such flirting was afoot, and she slightly teased that maybe I was over-selling how great of a kisser I actually am.

I played along with a "well you wouldn't know now would you?"

I know she's thought about it. Dangling our sexual exploits in each other's faces all this time was fun, two pervy people comfortable together in their perviness.

Then, a challenge. Sam boldly states that she'll just have to be the judge of such a claim. She suggests we go out to her car to smoke a doobie. If we feel the need to explore this further, we can. If not, we could just get high and return back to the bar.

I smile my best shit eating grin, extend my arm towards the door and say, "After you."

We step outside to find it's pouring rain. Big fat drops soaking everything it touches. We run through the dimly lit parking lot to her car and jump in, our skin and clothing damp against our warm bodies. She immediately grabs my face putting her lips on mine, it was as if I was watching it from the outside perspective it was so surreal. My hands wandered her frame I've observed countless times. It felt amazing, her body responding beneath my touch. Writhing seductively, giving away just how fucking bad she wants it.

When we came up for air, without a word, she slithered into the back seat. No invitation was needed, I followed. I leaned back as she made her way kneeling to the floor in front of me, positioning herself between my legs. Her eyes bored into mine as she released my buckle and unzipped my pants. She almost looked surprised when she reached in and pulled my cock out.

The fat raindrops drumming on the car and pavement outside cut the intense silence, almost hypnotic in its part in the ambiance.

That little curl of her lip manifests as she smirks looking at me, then wrapping her lips around my cock. She swallows me inch by inch, so slowly it's almost torture.

One side of me wants to savor every succulent moment of this experience, the other side wants every animalistic passionate filthy part of her I've imagined and heard from her confessions.

Her hands wander up my stomach and chest as she takes her time in her precision, expertly stroking my shaft, her moist lips and tongue drawing out my deepest guttural moans, turning her on even more.

She starts to speed up, making my cock throb and my balls spool and tighten. I can't help but raise my hips in an attempt to match her rhythm. I growl into the moist thick air how fucking good it feels. My fingers are tangled in her hair, so I ball up a fist and push her head further, feeling the tip of my cock at the back of her throat.

"How long have you wanted this cock..." I tease.

"I know you've thought about it...while you've pleasured yourself."

"So thirsty to be filthy like this with me." I add.

The entire scene, sounds and visuals, heightened my arousal. I could feel I was going to cum, I was so excited and ready for an intense climax. Unexpectedly, Sam grabbed a hold of my balls pushing me over that edge. I shove her mouth further down and fucking lose it, exploding my warm load into her throat, moans of extacy fill the car.

"Swallow! Swallow every fucking drop! Fuck!" I wail.

My entire being shook and convulsed as I went empty, embracing every dirty thought about her I've had. Fuck it was fantastic.

Sam sits up and wipes her mouth as I let out a deep sigh of contentment.

The rain outside drums us back to reality, prompting us to our next move. I button myself up. We simply went back to what we planned to do, she sparks up the joint and passes it to me. When finished, we run through the rain again back into the bar, making our way to order another drink.

Just then, Cheryl approaches, and I realize I completely forgot she was going to join us after she got off work.

She mentions she's been looking for us and texted me.

"Oh sorry, we went out to Sam's car to smoke a joint. My phone must be on silent. How was work?" I responded.

My mind was stirring with all sorts of thoughts...

"WTF did we just do?"

"Why do I want to do it again, or more?" "Is that what we want?"

"I hope shit isn't going to be weird now."

Sam comes over next me and Cheryl saying she has to leave.

She shouts over the music.

"I have to work in the morning. You two have an awesome night and I'll catch up with you later."

I pulled her aside and asked if she's ok. She flashes me her smirk as if she knew the shit sloshing around in my head and casually responds with, "We'll talk soon."

The next couple weeks went by and our contact was sporadic, which is normal, work schedules and life happening.

We made weekend plans to do just a low key movie night. I found myself a little anxious, being it's the first time we'll actually see each other since that erotic time spent in her car.

Excitement simmered as Saturday drew closer, I missed her and needed her company.

She was planning on heading over to my place with a pizza around 7ish. I was a little on edge, just nerves. When I hear that knock and open the door. Her big warm smile greets me, relaxes me. I feel those tight nerves melt away as she lets herself in as she always has. Making her way to the table, setting the pizza down. She asks what I've been up to as she removes her jacket and tosses it on the couch.

This way about us, that comfortable vibe just takes over. I didn't feel anxious anymore as I did throughout the day. It's just me and her, a regular night of deciding what to watch as we ate and talked. At first, it was almost as if we never had that blow job happen at all.

We skimmed over it briefly, basically agreeing that it was hot and didn't appear to change much between us. We had a couple beers, smoked some weed, and laughed as we always have.

Then it happened. That smile and look that lingers a little too long. That hint of seduction in the glance. It's just slight, but still hooks just right. Suddenly, my thoughts were on the fact that she wasn't wearing a bra again. That her t-Shirt was snug around her waist and tits just right for a little tease.

I watched her as she made her way to the kitchen counter, opening my cupboard for a glass. Her body shape was revealed by how her sweats hugged her. I could suddenly picture my hands molesting her curves and peeling her clothes off.

Fuck, just like that, a switch flipped and I wanted this creature. I wanted to know and feel her in those intimate and lustful ways I've only briefly thought about throughout our friendship, prior to the blow job.

My cock made an involuntary throb confirming it was game on.

I got up off the couch and came up behind her. My body only slightly pressed against her back, my hands took over. My finger tips curled up underneath the bottom hem of her t-shirt coming to contact with her skin. She inhaled deeply as my hands slid up to her tits, caressing and tweaking her nipples. They became so hard. Sam leaned her head back to rest on my left shoulder, pressing her body into me, arching her back. I traveled the length of her torso reaching her bare smooth mound. My fingertips dipping between her soft pussy lips finding her so wet for me already.

My cock stiffened instantly, grinding into her ass, which she pushed back up against me. I pushed two fingers inside her velvet cunt and she uttered the sweetest moan nestling her lips against my neck. Her right hand slowly trailed down my forearm, grazing my wrist, then finally coming to rest on my hand adapting to the movement of my fingers pumping inside her.

I could feel her becoming more wet, her moaning was an intoxicating sultry whisper. Fuck, I was lost in another surreal moment of bliss. Sam's body was twitching, almost as if she were in agony. Her grip to my right hand and wrist tightened as she desperately whimpered "Fuck me."

I couldn't fucking take it anymore, that's all I needed to hear. I pull my fingers back bringing them to my lips to taste her succulent juices, licking them clean before pulling her shirt off. Her warm skin was so soft and inviting.

I shift her body weight pushing her towards the counter, her palms lay flat on its surface. I peeled her sweats down to her ankles, I could hear her shallow heavy breaths of anticipation. My hands begin kneading and squeezing her luscious ass. Fuck I have wanted this, my cock was aching, sensitive to the touch as my sweats graze it pulling them down.

I assaulted her soaked cunt with my fingers one last time before gliding my length along her slit, leaving its slick trail on me. I feel her finger tip at her opening, directing my cockhead inside her with such ease. She moaned, gasped, and arched her back pressing her ass into my pelvis. I leaned into her body, slowly driving my length deeper.

Between breathy moans, I was able to manage a couple sentences...

"You feel so fucking good."

"I've been thinking about this since that night in your car."

Pinning her hands to the counter top, my lips releasing desperate whimpers on her neck and ear. I start to thrust into her faster, letting my excitement overcome me, rising that edge to explosion. I blurt out that I'm going to cum and she stops me.

Panting and twitching, she pleads, "Not yet. I want to ride you."

It was hard to pull back, I wanted to cum so badly in this lustful moment. I stepped back giving Sam space to stand up straight and we transitioned back to the couch. I sat down and she immediately climbed into my lap to straddle me pulling my t-shirt off me tossing it to the floor. We started making out while her hands wandered my chest, trailing over my shoulders, down my arms, then latched my hands bringing them to her soft full tits. I fondled her nipples with my fingers, then my tongue. She started grinding her saturated pussy and clit along my length driving fucking mad.

I reached down to her slit to touch her and she swiftly grabbed my wrists tucking them under her legs pinning them down. Not hard, just slight uncomfortable pressure. The curl of her lip emerged as she smirked at me. She knew I could get out, but I wanted to see where she takes this. I felt comfortable enough with Sam to let her take that lead and I was incredibly turned on.

She reached behind me to grip the back of the couch plunging herself down on my cock. Grinding hard and rough, using her grip to the couch to push deeper. My wrists and hands felt the pressure of her weight shifting with each thrust. Simultaneously, the sensations her pussy and moans were creating in me flooded my senses. Sam grabs my head pushing my face into her tits. I could feel my cock swell and throb, I needed to cum again.

She could tell and teased that I wasn't allowed yet.

Lifting herself off my lap, she moved and nestled herself between my legs. She lightly stroked my cock with her lips letting my climax subside a little. I reached for her hair and she intercepted by grabbing my wrists, hugging them to the side of my legs. Her mouth strokes became deeper as her head dove down my cock. She's enjoying this. Just toying with me, the tease of it.

As she pulled her head back, her eyes stared me down. Then, her little smirk. Even in such an intense moment, still so playful as she stood up to mount me again.

Once again tucking my arms under her legs immobilizing me as she started bouncing up and down on my cock. She leaned into me, her body heat radiated on my skin.

She started moaning, deeply and louder. Her heavy panting was so fucking sexy, I couldn't resist any longer. I yanked my arms out from their bonds wrapping them around her. Lifting my hips up pounding into her saturated cunt, growling in her ear how I'm going to fill her. My lap was soaked as she started to cum, I'd never felt a woman this wet before. Sam's body twitched and spasmed against me. Her sultry whispers telling me to cum were dripping with desperation.

The sounds of bodies colliding and our moans filled the room. I squeezed her tight against me as I erupted violently, panting through my intense big finish.

As we recovered, our breathing returned to a calm content pace and our bodies were tacky from exhausting each other. We freshened up, then retreated back to the couch with Sam snuggling in next to me as the little spoon.