A Friendly Face at the Bar

It was always nice to see Caitlin show up at the bar. She was a rep for one of the local breweries, but she never came across as a salesperson. She was honestly interested in what my customers liked, and what she could do to keep them happy. She was also super cute. Mousy blonde hair, often with a crazy tint or two thrown in. Band t-shirts and overalls. High tops. Not a scrawny model type, but comfortable in how she looked, and it showed. And she knew as much about beer as I did, or more, and could probably match me pint for pint.

It was a bit unusual to see her in so late on a Sunday though. I was just waiting for the regulars to clear out. “Business or pleasure,” I asked.

“Always a pleasure coming in here,” she said with a smile.

“I bet you say that to all the bartenders.”

“I was just in the area. Thought I’d check in.”

“You’re always welcome. What can I get you?”

“Surprise me.”

The place had pretty much cleared out. I pulled a pint of one of her APAs and a shot of Fernet for each of us.

“Slainté,” I said, and we touched glasses.

“Business is good?” she asked.

“Could be worse,” I said. “We’ve been through tougher times. You?”

She sighed. “It’s a grind sometimes, but people always want beer.”

“I’ll drink to that.” We raised our glasses again.

We chatted for a bit while I started to tidy up. I’d been thinking I could get a jump on closing early.

“Is that a hint?” Caitlin asked.

“Fuck no, take your time,” I assured her.

We made small talk as I turned up the chairs, checked the bathrooms, put away the garnishes. It was a proud fake dive bar, not too many perishables, not too many seats. Shutting down didn’t usually take long. Caitlin offered to pick up a broom but I waved her off. “You’re a guest. You don’t work here.”

“Sometimes it just feels good to keep busy,” she said.

“Things are tough, I know. But this is a ‘forget your troubles’ kind of dive bar.” I picked up my shot and she did the same, throwing hers back as easily as I did mine.

“Let me at least clean these,” she said of our empty glasses, and I couldn’t refuse her. I waved her to the sink behind the bar as I swept up. She knew her way around a bar, that was obvious.

Pretty soon the place was ready for close, and she shadowed me as I locked up. And then we found ourselves on the dark, empty street.

“You done for the night?” she asked.

We didn’t open till 5:00 p.m. the next day. “There’s probably a bit of gas in the tank,” I said. “What did you have in mind?”

“Just feeling like I could use a nightcap,” she said.

“Not much open at this hour.”

“There’s usually something to drink at my place.”

I paused for a moment. Our relationship had always been professional, but friendly. I didn’t know where this might end up. But it was late, and I had no plans. “Lead the way,” I said.

We talked shit while we walked. How the city had changed, bars we missed, bands that had come and gone. Eventually we got to her walkup. I followed her up the stairs, unable to see anything but how her worn jeans hugged her ass. My mind wandered, unbidden, to imagine how it would feel to be pressed tight against it. I pushed the thought away, making a mental effort to just go with the moment.

“What’s your poison,” she asked, walking into a spare but stylishly rustic kitchen.

“Dealer’s choice,” I said.

She pulled a bottle of Ardbeg from the shelf and a couple of juice glasses.

“That’s the way to my heart, you know,” I joked.

“Intuition,” she shrugged.

We sat down at her small harvest table and raised our glasses.

“So this is maybe bad for business,” she started. “But you looked lonely, and have done for a while.”

“I have resting lonely face, I guess.” She wasn’t wrong, though. My last relationship had ended six months before, and I’d just thrown myself into running the bar to try to keep it off my mind.

“And I think we’re pretty different people, you and me… but I keep pretty busy myself, and haven’t had a lot of time for relationships lately either… well, ever, really.”

“So what you’re saying is, we’re friends…” I said tentatively.

She started laughing. “I’m sorry. This is awkward. I’m not usually so… out there.”

Then I had to laugh. “What, you, extrovert of the year, with your pink hair, and your tattoos, and your –” I stopped myself but my eyes gave me away.

She looked down modestly. “It’s all a show. This is me,” she gestured around the one bedroom apartment with her eyes. “This is my life, there’s work, and there’s me, here, alone.”

“That makes no sense to me.”

“I think the guys who I’d like are afraid to talk to me. And the guys who aren’t afraid to talk to me, well… they’re kind of all assholes?”

“Well it’s a damn shame,” I said.

“Is that a yes, though?”

We’ve had a few drinks, I thought. We’ve always gotten along so well. But we kind of work together, and how smart is it to mix work and… benefits?

Caitlin wasn’t fazed by my hesitation. She reached up under her t-shirt and did that magical thing that women do sometimes, half-graciously working herself out of her bra without taking her shirt off, and then flinging it, slingshot-style, out of one sleeve.

She looked me straight in the eyes the whole time, with a smile. I was speechless. The tent that her nipples made against her shirt had me rock-hard instantly. She topped up our glasses.

“Still thinking?” she asked.

“I’m not sure I’d call it thinking,” I said.

“Don’t get too cute. It’s entirely possible to be too cute for this gig.”

She put down her drink and peeled her t-shirt off over her head in one motion, without breaking our gaze. Her breasts were full and round, her nipples engorged and puffy.

“Those are magnificent,” I blurted out, instantly embarrassed at my awkwardness.

Caitlin blushed a bit. “Thank you,” she said quietly. She leaned across the table and kissed me, taking my hand and pulling it to her breast. “Still thinking?” she asked again.

“I want you so much,” I breathed, hoarsely.

“Well guess what,” she said. “You can have me.”

She stood up, and I followed her lead. We embraced, and the fullness of her felt wonderful, the softness of her skin against my bare arms. How would I describe her body? There was just nothing out of place about her. There was maybe a bit of a roll over the waistline of her jeans – but I certainly wouldn’t want anyone judging me on the same scale. She wasn’t even what they used to call voluptuous. She was like… the hot chick on the softball team. I don’t know! That sounds silly. Just a real woman, who you know, who you want to hold close to you.

“So does this have rules?” I asked.

“I don’t know. I’ve never done this. I think… if you get feelings? For me, or anyone else, you tell me? And I’ll do the same.”

I lied and said, “sounds good.” I lied because I already had feelings that might have been… feelings. And if that makes me sound like an idiot, that’s a pretty good assessment of the situation. Me sounding like an idiot, and probably being one.

She turned and walked toward her bedroom. “Bring the drinks,” she said. I dutifully grabbed our glasses and followed her. She flipped on the lights just ahead of me. The lighting was warm and pleasantly dim. The bed was immaculate with a soft duvet on top, and a mound of pillows in the corner. Nothing was out of place. It looked like a freshly turned down hotel room.

“This is nice,” I said. “Do you have, like, a service or something?”

She shrugged. “It’s a small place… it’s not too hard to to keep tidy.”

She stood in front of me, topless, wordless, with a wry smile on her lips. I put our glasses down on the nightstand and took her face in my hands. “You’re gorgeous,” I said, as my longing spilled out into a lingering kiss. She reciprocated, putting her hands on my ass and pulling me toward her.

“I need you to suck on my tits,” she said, unbuttoning her jeans and stepping out of them. She sat down on the edge of her bed, now wearing nothing but a pink thong. I had only a second to take it all in, her pale flesh, her curves, a smattering of tattoos, and her welcoming smile. I knelt down between her legs and took one soft, perfect nipple into my mouth.

Caitlin put her hands behind my head and pulled me to her with a sigh. Her soft flesh surrounded my face as I moved from one breast to the other. She pushed them together for me so that I could almost, but not quite, hold both her nipples in my mouth at once.

Her hands reached down to undo my jeans. I wriggled out of them frantically, my hard cock straining against my briefs. I stripped off my t-shirt and put my hands on her shoulders to ease her back onto the bed.

“Take your time,” she said. I kissed her soft breasts some more, and she ran her fingers through my hair. “That’s it. That’s it,” she sighed, wrapping her thighs around my torso. The crotch of her thong was warm and damp against my stomach. Pulling away from her reluctantly, I hooked my fingers around the waistband and pulled it down her legs, anxious to feel her warmth against my skin. Her pussy was taught yet fleshy, shaved except for a tidy triangle pointing down from her belly. I immediately began stroking the length of it with my tongue. She lifted one leg up to give me better access, then put her other thigh over my shoulder as I pressed my face into her.

“Ohh, that’s right,” she said. I couldn’t get enough of her. I licked her until she was dripping, then put my mouth over top of her clit and held it there. I slid two fingers into her soft folds as she closed her thighs around me, sucking on her from the outside and stroking her from the inside as she squeezed and ground herself against me. Eventually she gave herself over to her first orgasm, crying out my name, grabbing hold of the duvet in her fists, pulling me into her with her legs.

“Oh god. Oh god. Oh god,” she said as the waves rolled over her. And then those magic words, “Fuck me. Please. Fuck me now.”

I pulled my boxer briefs down and climbed on top of her, one arm under her leg, sliding my entire length into her sopping wet pussy in one stroke. Her eyes went wide, her face lit up by the broadest smile. “Holy shit,” she whispered. I held myself in her for a moment, trying to freeze the instant in my mind forever.

The next few minutes were a blur of me seeing how far I could push myself inside her, how quickly I could make her cum. Her body had a language all its own, and in time I took her cue to let her flip me over and ride me as she brought herself to orgasm. She cried out, shuddering, and then collapsed on me, panting.

“Your cock feels so good in me,” she said, kissing my face.

“It does,” I said. She laughed, squeezing me tight inside her. I could feel every little movement she made. Then, suddenly, she slid off me to lie back against her pillows.

“Scotch break,” she said, breathlessly.

The air was cool on my slick cock, which stood rigid and twitching. I was desperate to fuck her hard until I exploded inside her, but reason suggested it might be nice to take our time. I found our glasses and handed one to her, sitting opposite her, admiring her gorgeous body.

“To friends,” I said.

“To friends,” she agreed. We downed the rest of our drinks.

“I’ll be right back,” she said, and dashed off to the washroom. I slid up against the pillows where she’d been sitting. They were soft and crisp and clean. My cock was throbbing, anxious for release.

Caitlin returned with a glass of water for each of us. “You need to stay hydrated,” she said, in an almost sisterly way. I drank, and she was right.

She sat down on the bed by my leg and stroked the inside of my thigh gently. Her skin was pale, her hips ample but well-proportioned. I felt like I was dreaming, seeing her naked in front of me, with her juices smeared all over me.

“It doesn’t make sense that you need an FWB,” I finally said. “You could have any guy you want.”

“God, you’re sweet,” she said. “But there’s something I haven’t told you.”

“You’re a vampire?” I said, jokingly.

“Good guess,” she laughed, then her face got serious suddenly. “I’m a cam girl.”

I was honestly stunned. “You mean… you have sex, online?”

She searched for the right words. “Not exactly? I mean, not live, mostly? And just solo.”

I must have looked around the room without thinking.

“Oh my god, no! You’re not on camera!” She slapped my leg in mock anger. “Don’t be dumb!”

“Okay,” I said, tentatively, trying to get it all straight in my head.

“Are you mad? Is it too weird?”

“No, no, it’s just a bit of a surprise.”

“I started maybe a year ago. I needed some money. The brewery job is great, but the pay isn’t. And, well, it’s my body, and to be honest I kind of like knowing strangers are getting off looking at me. So I’ve got an OnlyFans, a couple other sites, and the money works out okay.”

“You just tell me if I’m getting too personal, but… your side hustle is getting off on camera and you still need an FWB?”

She climbed into bed beside me. “I know, right? But it’s kind of like… my customers aren’t my friends.” She took my hand and put my palm to her lips. “It’s not like this.”

We sat in silence for a few moments.

“It’s lonely, in its own way. And it’s a bit of a hurdle for new relationships.”

“It’s okay,” I said.

“What do you mean?” she asked, tentatively.

“I mean all of it. You’re right, it’s your body… I get it.”

She leaned over and kissed me. “Holy shit, it feels so good to tell someone.”

“I’m glad it was me,” I said.

Her bare belly brushed against my cock as we kissed. It twitched, straining for attention. She wrapped her hand around it, still kissing me, sliding the skin up and down the shaft. I moaned a bit. She kept stroking me like that, firmly and slowly, as she kissed her way down my chest, finally reaching the tip of my cock, where a bead of precum had collected. She tucked her hair behind her ear so I could see her face as she licked it off, and then proceeded to slide her mouth down over it. I caressed her breast in my hand, rolling the hard nipple between my fingers. She reciprocated by cupping my balls, gently fondling them, and then, with a firmer touch, stroking the base of my shaft with her fingers. I moaned louder this time, in spite of myself.

“Is this okay?” she asked softly.

“Too okay, almost,” I said.

“You have such a beautiful cock,” she said. She continued sucking on me, deeply and slowly, as I stroked as much of her luscious body as I could reach. The way she was massaging my crotch was making me crazy. My cock felt harder than it’s ever felt, and my ass muscles were clenching and trembling.

“Baby, that’s going to make me cum,” I warned her. She didn’t stop. I felt the pressure building faster.

“Baby wait, no – I’m going to – “ I didn’t have the conviction to stop her though. I felt a delicious wave of pleasure well up in my balls as I shot spurt after spurt of cum into her mouth.

“Mmmm,” she moaned between swallows, slowing her pace but not relenting. My orgasm felt like it lasted 30 seconds. She took her time releasing me, waiting until I started to go soft before letting me slip out of her mouth. “Sorry,” she said, finally.

“For what?”

“I think I heard a ‘no’ in there. Maybe I should have stopped.”

“I wouldn’t worry about it.”

She climbed her way back up me, drawing in to kiss me but stopping. I nodded to let her know it was okay. Her lips were slick with my cum, and her mouth tasted of me – earthy, salty. “Is this how friends with benefits usually goes?” I asked.

“What, the bit where you call me sweet names while you cum in my mouth?”

“Or the swallowing and cuddling,” I said.

“I say…” she traced a finger around my nipple, “we just try to make each other feel good.”

“Sounds fair,” I said. “Do you feel good?”

“So good,” she said.

“Me too.”

We sipped our drinks and talked about tattoos and scars and first times. Most uncomfortable first dates. First crushes. We were cuddled up, naked, and I couldn’t keep my hands off her breasts.

“Is this alright?” I asked her tentatively.

“I love it, honestly,” she said. “Here, wanna see something?” She sat up, facing me.

She tucked her chin into her chest and brought one breast up to her mouth, tucking the nipple between her teeth and holding it there, then letting go with her hands, and stretching her arms wide. It almost looked like it would hurt, but you couldn’t tell by her face.

“Wow,” I said. “Did you work that out for the camera?”

She let go with her teeth and let her breast slip back down into a waiting hand, laughing a bit. “I do it on cam sometimes, they love it. But I learned I could do it on my own years ago.” She looked down at my cock, which had sprung back to life. “You like it too, I think.”

“Your breasts are fucking gorgeous. All of you is.”

“Thank you,” she said again, smiling. “You know what I think would be fun?”

“I can’t wait.”

“If you want,” she straddled my legs and inched toward me, “you could cum inside me. But I don’t want you to pull out after. I want to fall asleep with you inside me, and wake up when you get hard again.”

If I wasn’t completely hard before, her proposal got me all the way there and then some. She inched forward a little more and raised herself up over my cock, slipping it inside her and sliding down over it. “That sounds amazing,” I sighed.

I cupped one of her breasts in my hand and put the nipple between my teeth and bit down gently. Caitlin groaned deeply and began fucking me slowly, rising and falling onto my lap with a steady, gentle rhythm. After a while she slid a hand down between us to massage her clit and pressed her mouth onto mine. I held her tightly by the ass as her bucking gradually became more insistent. Soon I was pulling her down onto me faster as she cried out for joy, cumming again as her beautiful tits bounced in front of my face.

Once she had caught her breath, I guided her off me onto her hands and knees, feasting my eyes on the generous curve of her ass. She knew where I wanted her to move with little more than a touch, backing up so that my cock was perfectly positioned against her pussy. I slid into her easily, pulling her toward me by her hips until finally I was balls deep in her again. I started slowly but soon I was slamming into her with abandon. I’m sure her cries must have woken the neighbours as one climax followed another, with her movement and the sweet wetness of her finally pushing me over the edge along with her. I held myself as deep inside her as I could as my balls pumped my sperm into her once again, slowly easing her down until she was lying prone underneath me. We lay in silence, panting and sweaty.

I did my best to stay hard. When I felt myself receding, I pushed against her ass gently so that my cock would swell a bit inside her. I motioned for her to roll back with me onto our sides, spooning up behind her, reaching around to hold one of those breasts that I couldn’t get enough of. I kissed the skin of her back lightly, tasting her salty sweat.

“This is nice,” she sighed, sleepily.

“Mm-hmm,” I answered, suddenly realizing how exhausted I was. Falling asleep wouldn’t be as difficult as I thought.

Waking up inside her was an unforgettable sensation. You know that feeling when you’re having a truly good dream, you have a slow realization as you wake up that it’s not real life? In those dark morning hours I woke up remembering that I’d fallen asleep in a dream and was still in it. My penis had stirred to life and had awakened Caitlin’s welcoming vagina. She was warm and sweet and wet, and as she slowly woke she pushed back against me. We undulated sleepily for a while, as I snaked an arm under her to pull her closer to me. She turned a bit and raised her leg over mine at one point, so that she could push herself further down onto me. I let go of her reluctantly, momentarily, to lift her leg over me, somehow – it seems impossible in retrospect – to face her without leaving her, our legs tightly intertwined, her eyes now wide open, pale grey and blue, as I bathed her in kisses. “You’re perfect,” I whispered.

She pulled me close to her, her breasts mashed against my chest, kissing me hungrily. “I’ve wanted you for so long,” she replied.

“This is not how this is supposed to work,” I said, pushing myself up into her.

“I don’t care,” she said.