Tyler had been getting his hair cut for awhile from a sexy tattooed brunette named Allison that was a friend of his girlfriend. Allison wasn't a professional hairdresser but she did a good enough job. Tyler kept coming back since she was flirty and to be completely honest he loved her really big tits that she always seemed to be showing off. On Tyler's birthday he doesn't know that his wife has told Allison she can give him a blowjob after his haircut.

Chapter 1: The Birthday Haircut with Benefits

"Hello?" I said softly as I pushed open the door to Allison's apartment, the scent of hair products and something sweet—maybe vanilla—enveloping me. I stepped inside, my sneakers sinking slightly into the plush, worn-out rug that covered the floor. Allison had been friends with my wife for a long time and she preferred I enter without knocking.

"Tyler, right on time. Sarah said you'd be here at two." Allison called out from the kitchen, her voice warm and slightly husky. Her apartment was a cozy, eclectic space. She had been doing haircuts out of her apartment as a side gig for as long as Tyler knew her.

"You know Sarah," I replied, shrugging off my jacket. "Got to make sure I keep to my birthday schedule."

Allison emerged from the kitchen, a mug of steaming coffee in hand. She was dressed in her usual casual but sexy style—a low-cut crop top that showcased her ample cleavage and a pair of ripped jeans. Her dark hair was pulled up into a messy bun, with a few loose strands framing her face. Her eyes sparkled with amusement as she looked at me.

If I was being honest, how hot Allison was the main reason I had never found a proper barber before. I enjoyed the flirtatiousness and energy she brought. I was a sucker for her tattoos too. And again in the name of being honest, she had a great rack. - which today's tank top wasn't exactly hiding. I tried to keep my eyes on her face, not wanting to be disrespectful. Plus I would get a chance to take a better look when she cut my hair.

Allison took a sip of her coffee, her eyes never leaving mine. "Sarah did tell me it's your birthday today."

I nodded, running a hand through my hair. "Yep, the big three-oh. Feeling every bit of it," I joked. "I mean, I'm officially over the hill now, right?"

"Get anything good gifts for the milestone?" Allison asked, gesturing towards the kitchen.

I walked towards the kitchen continuing our chat. "Sarah hasn't given me my gift yet." I chuckled, sitting in the kitchen chair. "But I'm sure it'll be something unique. She has always been good with gifts."

Allison raised an eyebrow, a playful smirk on her lips. "Is that so? Well, Sarah did tell me to make sure to take extra special care of you today."

I felt a jolt of surprise, but I tried to keep my expression neutral. "Oh, really? And what does that mean?"

Allison's smirk widened. "You'll see, birthday boy. Now, let's get you set up." she said as she draped a cape around my neck, reaching to secure it at the back. I felt the soft fabric brush against my skin, and I couldn't help but notice she wasn't wearing a bra as she leaned over me. Her breasts, barely contained by the low-cut tank top, were right there, just inches away from my face. I could see the outlines of her nipples through the shirt as well.

I swallowed hard, trying not to stare, but it was a struggle. I mean, come on, she was right there, and her cleavage was on full display. I could see the edge of her tattoo peeking out from the top of her shirt, and I found myself wondering what it looked like all the way down.

I tried to focus on the conversation so I didn't get caught staring. "So how are things with Ron?" I decided to ask about her boyfriend. I had only met him a few times but figured it was a safe area of conversation.

"Oh we split up last week ," Allison said, her voice casual as she began to run her fingers through my hair. "I am surprised Sarah didn't tell you."

"Well, I'm sorry to hear that," I said, keeping my voice steady. I could feel Allison's fingers working through my hair, her touch gentle yet firm.

Allison shrugged, her shoulders moving slightly, causing her tank top to shift and reveal more of her cleavage. I had to look away, my eyes landing on the framed photos on the wall. "It was just one of those things. We weren't the right fit, you know?" Allison continued, nonchalantly, as she reached for the razor on the counter.

As she turned around, her eyes locked onto mine. "I'll be honest he was pretty boring in bed too," she admitted, a mischievous glint in her eyes. "But enough about him. Today is all about you, birthday boy." She winked, and I felt a flush creep up my neck. I couldn't help but smile at her candor.

"I mean, you were way too hot for him." I blurted out, immediately regretting it. I had no idea why I said that, but it was too late to take it back. Allison just laughed, which eased my anxiety.

"Well, thank you, Tyler," she said, her voice laced with amusement. "I appreciate the compliment."

I felt my face grow hotter, and I looked down, avoiding her gaze. "Sorry, I didn't mean to say that out loud."

Allison's fingers paused in my hair, and she leaned down, her voice low. "Don't be sorry. I like hearing that you think I'm hot." She whispered, her breath warm on my ear. "Now, let's get you looking sharp for your birthday."

She started cutting my hair, her fingers deftly combing through the strands. The clippers buzzed softly, and I felt the vibrations against my scalp. Allison's hands were steady, her touch confident. I closed my eyes, trying to block out the sight of her cleavage, but it was hard. Every time she leaned over, I could see more of her. The crop top was riding up, and her breasts were threatening to spill out.

I tried to focus on the sensation of the clippers against my scalp, the cool metal and the gentle buzzing, but it was hard to ignore Allison's amazing underboob. I shifted in my seat, trying to find a more comfortable position, but it was no use.

My jeans felt a little too tight, and I knew exactly why. Allison's proximity, her touch, and the way she was dressed—or rather, undressed—were all having an effect on me. I hoped she didn't notice, but I wasn't sure how much longer I could keep my composure.

Allison, seemingly oblivious to my discomfort, continued to chat casually, her fingers working through my hair with practised ease. "Sit still, you don't want my hands to slip ," she teased, her voice laced with a hint of flirtation. I swallowed hard and tried to look down but seeing the tiny straps of Allison's thong sticking out over the lowrise ripped jeans wasn't helping my situation. I could feel my heart pounding in my chest, and I was pretty sure Allison could see the bulge in my jeans. I tried to think of anything else, but her fingers in my hair, her breasts inches from my face, and the scent of her perfume were making it impossible.

Then, as she leaned over to grab a new comb, I noticed something new. A small, intricate tattoo peeking out from the waistband of her jeans, just above the curve of her hip. It was a delicate, black ink design, looked like part of a spider.

I couldn't help but ask, "New ink, Allison?" My voice was steady, but my heart was pounding in my chest. I was curious, and I was also hoping to distract myself from my growing arousal.

Allison looked down at where I was looking, then back up at me, a playful smile on her lips. "You noticed, huh? Yeah, I got it two weeks ago. It's a black widow." She leaned back slightly, giving me a better view of the tattoo.

"You like it?" she asked, her voice soft. I nodded, my eyes still on the delicate ink. Before I could say something though Allison then added, "Oh wait you can't really see it all . It's a bit bigger than I thought it would be." Time then stood still as she slowly unbuttoned her jeans, revealing more of her pink panties. I could barely comprehend what was happening as she pulled her pants down further than needed to expose the entire design.

The black widow tattoo was indeed large, and beautiful, with intricate details. My attention, however, was drawn to her ass and the thin strip of fabric between her cheeks as she turned her side towards me. I swallowed hard, trying to keep my eyes on the tattoo instead of the tantalizing glimpse she was giving me.

Allison seemed to notice , a small smile playing at the corner of her lips. “You okay, Tyler?” she asked, with her pants still pulled down.

I cleared my throat, trying to find my words. “Yeah, I’m good,” I managed to say, my voice a little huskier than it should have been. “It’s just...ah, it’s a really nice tattoo.”

Allison chuckled as she pulled her jeans back up.

"You are cute, Tyler," she teased, her voice laced with amusement. "You're blushing like a schoolboy."

I felt my cheeks grow even hotter, and I looked away, focusing on the framed photos on the wall. "I'm not blushing," I insisted, trying to keep my voice steady.

Allison laughed again, the sound warm and inviting. "Sure, Tyler. Keep telling yourself that."

She turned back to her work, moving behind me again, her fingers combing through my hair before starting cutting again.

"So, Tyler," she began, her voice casual, "Sarah told me work has been crazy for you?"

I cleared my throat, grateful for the change of subject. "Yeah, it's been a bit hectic. Lots of demand for contractors right now , and I've been pulling long hours," I replied, trying to focus on the conversation and not the fact that Allison had just shown me her g-string panties.

Allison hummed sympathetically, her fingers working through my hair. "Well, you deserve a break. It's your birthday, after all."

I nodded, trying to keep my voice steady. "I appreciate that. Sarah has something planned for later, but I'm not sure what it is."

Allison paused, her fingers still in my hair.

"You know, Sarah mentioned something about a special gift for you. Said she wanted to make sure you had a birthday you'd never forget."

I raised an eyebrow, curious. "She didn't give me any hints." I said, trying to keep my voice nonchalant, but I couldn't help the curiosity that was creeping in. Why did Sarah tell Allison about it? Was it a surprise party?A weekend getaway? Or something else entirely?

"Well, Tyler," Allison said, her voice calm, "I think you should just enjoy the day and let the surprises come to you." She put down the razor and reached for the scissors. "Let's get this cut finished up." Allison said, her voice soft yet commanding.

She started to work again, the scissors snipping softly as she shaped my hair. I tried to focus on the sensation of her touch, the cool metal of the scissors against my scalp, the gentle tug of her fingers, but it was hard. The scent of her perfume filled the air, and I could feel her breath on my neck as she leaned over to cut the hair at the back. Her breasts, barely contained by the low-cut crop top, pressed against the back of my neck. I couldn't help but wonder if she was doing to deliberately tease me? If so why? I was dating one of her best friends.

I knew I shouldn't be getting turned on by Allison, but I couldn't help it. She was so confident, so sexy, and I was a guy, after all.

"We are getting close to finished ," Allison said, her voice soft. "You want me to leave the sides a bit longer, or keep it short all around?"

I tried to focus on her words, but it was hard with her breasts pressed against me. "Uh, short is fine," I managed to say, my voice a little hoarse.

Allison moved in front of me again, and crouched down to exam my hair lines. I could see the faintest hint of a smile playing at the corners of her mouth. It was taking all my willpower to not stare at her cleavage, so I tried to keep conversation going

"So, what else is new with you, Allison? Besides the tattoo and the breakup, I mean." I asked, trying to sound casual.

"Well I got a new piercing ," Allison replied, her eyes filled with mischief as she got back to work.

"Oh? I didn't notice it," I said, my eyes scanning her body, trying to find any sign of a new piercing. Wait did she have a small nipple piercing? I can't believe I hadn't noticed. Especially since she wasn't wearing a bra.

Allison laughed, her eyes sparkling with amusement. "It's not on my face, silly. It's a bit lower," she teased me back. Confirming my suspicions.

I couldn't resist flirting back . "Lower, huh? Well, I'll have to keep an eye out for it then," I said, trying to keep my voice casual.

"Oh, you will, will you?" she teased, her voice soft. "Or I could just show you." She stood up, her eyes locked onto mine, a playful smile on her lips. I felt a jolt of surprise, but I didn't look away. I couldn't. She reached for the hem of her crop top and time stood still for me. Was she actually going to show me her tits? I coudn't believe it. While it wasn't technically cheating, I imagine Sarah wouldn't exactly be thrilled either.

Allison's smile widened, as if she could see the internal struggle playing out on my face. She slowly began to lift her shirt, inch by inch, revealing more of her underboob. I swallowed hard, trying to find my voice, but no words came out.

Allison's boobs then suddenly popped out the bottom of her top as she lifted it up to her chin, revealing her bare breasts. They were the most perfect pair I had ever seen too - the were huge on her small frame and gravity-defying for their size. With small, hard nipples that were a shade darker than her skin with a single one pierced. I couldn't help but stare, my mouth slightly agape.

"See I got this nipple piercing," Allison said, her voice casual as she pointed to the small barbell that adorned her left nipple. "I thought it was a fun addition to my collection."

I swallowed hard, trying to find my voice. "It's...it's very...interesting," I managed to say, my eyes still fixed on her chest.

Allison chuckled, acting like it was perfectly normal for her to have her tits out. "You like it, huh?"

I nodded, my cheeks growing hotter. "Yeah, it's...it's really something," I stammered, my eyes finally meeting hers. Allison's smile widened as she pulled her top back down, tight over her breasts. I felt a pang of disappointment, but I had seen far more than I expected today - that was for sure.

"Let's finish you up , birthday boy," Allison said, her voice back to its usual playful tone. She picked up her scissors again, her hands steady as she snipped away at the stray hairs around my ears. I took a deep breath, trying to calm my racing heart. Allison's breasts, now safely hidden beneath her top, were still a vivid image in my mind. I couldn't help but wonder what it would be like to touch them, to feel their weight in my hands. I shook my head slightly, trying to clear the thought from my mind. I was here for a haircut, not to fantasize about Allison's breasts.

"Getting close to finished birthday boy," Allison said, her fingers working through my hair. I could feel her breath on my neck as she leaned in to examine her work. "You look sharp, Tyler. Sarah's going to love it."

I cleared my throat, trying to find my voice. "Thanks, Allison. I appreciate it." I was still trying to process what had just happened. Had she really just flashed me? And why? I knew I should feel guilty, but all I could think about was the image of her breasts, the hard nipple with the small barbell piercing.

Allison stepped back, her eyes scanning my hair one last time. "All done," she declared, a satisfied smile on her face.

"You look great, Tyler. She reached for the cape around my neck, her fingers brushing against my skin as she undid the clasp. I felt a shiver run down my spine at her touch, and I hoped she didn't notice. "Just give me a minute to cleanup."

"Sure thing, Allison," I said, running a hand through my newly cut hair. I grabbed my phone out of my pocket to check the time while Allison cleaned up. It was already past three, and I had a feeling Sarah would be home soon. I wondered if she knew about Allison's little... performance earlier. I mean, it was her idea to get my hair cut here, after all. I shook my head, trying to clear my thoughts. I was overthinking it. There was no way Sarah knew Allison would flash me. Right?

I noticed I had a message from Sarah . I opened it, my heart pounding in my chest. I wasn't sure what to expect. I read the words on the screen, my eyes widening in disbelief. "Your birthday present is getting to whatever you want with Allison. Enjoy, birthday boy. - Sarah." I reread the message, just to make sure I wasn't imagining things as never in a million years would expect this kind of 'gift'. I looked up, Allison was smirking as she was sweeping up my hair.

"What's got you so flustered, birthday boy?" she asked in a playful tone. She had obviously knew what was up. "Uh, nothing," I said, tucking my phone back into my pocket. "Just a message from Sarah."

Allison raised an eyebrow, a playful smile on her lips. "And what did Sarah have to say?"

I decided to mess with Allison a little bit for teasing me so much. "She, uh, she just told me to pick up milk on the way home," I said, trying to keep my voice casual.

Allison's smirk widened, and she leaned the broom against the counter, "Is that so?" She paused and took a few steps towards me and called my bluff, "Well, I guess I will have to suck someone else's dick then ." She said it so casually, like she was talking about the weather.

I couldn't help it, I lost my composure and laughed out loud. "You know you almost gave me a heart attack during the haircut, right?" I said, still chuckling, trying to regain my composure.

Allison laughed and rolled her eyes. "I'm sure looking at my tits and ass was soooo difficult for you,"she said as she took a few more steps towards me, her hips swaying slightly. "I mean, you were practically drooling all over yourself."

She was now standing right in front of me, her eyes locked onto mine. I could feel the heat radiating from her body, and I could smell her perfume, a sweet, intoxicating scent that made my head spin. "Well, you did make it pretty hard to concentrate," I admitted, my eyes flicking down to her cleavage before snapping back up to meet her gaze.

Allison's smirk widened and before I could react, Allison climbed onto my lap - her legs straddling me. I wrapped my arms around her waist, pulling her closer. She was warm and soft, and I could feel her breath on my neck as she leaned in. Allison's hands found their way to the back of my neck and she pulled me closer, her lips brushing against mine. I hesitated for a moment out of guilt, but I told myself I had permission, my lips parting as hers pressed against mine.

Allison's tongue slipped into my mouth, exploring, tasting, and I couldn't help but respond in kind. Her kiss was confident, hungry, and I found myself losing myself in it. Her hands tightened around my neck, pulling me closer, her breasts pressing against my chest.

I reached around, my hands finding their way to her ass, squeezing the firm, round flesh. Allison moaned into my mouth, her body pressing against mine, her hips grinding against my growing erection. We had such an intense energy between us. I pulled away from her mouth, my lips trailing down her neck, biting gently on her. She gasped, her head falling back, exposing her neck. I took the opportunity to trail my lips down her throat, my hands now finding their way to her breasts. They were heavy in my hands, the soft flesh filling my palms. I could feel her nipples hardening under my touch, my thumb brushing against the small barbell piercing. Allison moaned, her head falling back further, her hands gripping my shoulders. "Fuck, Tyler, that feels so good," she panted, her hips grinding against mine.

I wanted more, I needed more. My hands moved to the hem of her crop top and I slowly lifted it up, her boobs falling out the bottom. They were even more stunning up close, the hard nipples begging for attention. Allison's eyes fluttered closed as I cupped her breasts, my thumbs brushing over her nipples. Nothing against Sarah, but Allison's were the most perfect tits I ever got my hands on. I leaned in, taking her unpierced nipple into my mouth, swirling my tongue around the hard peak. Allison gasped, her hands gripping my hair, pulling me closer. I sucked harder, my teeth grazing the sensitive flesh, and she moaned, her body pushing against mine.

"Fuck, Tyler," she panted, her voice hoarse with desire. "That feels so fucking good." Allison's voice was a low moan, her body arching against mine as I switched to her other nipple, the one with the piercing. I sucked gently, feeling the cool metal against my tongue, and Allison's body shuddered. She was so responsive, so eager, and it was driving me wild. I brought my free hand up to her other breast, squeezing it, kneading it, as my mouth continued to tease her nipple.

"Holy shit, don't stop" she moaned, her voice desperate. "I think I am going to cum just from you sucking my tits." I felt a surge of pride at her words, and used my hand to pull on her nipple, making her gasp and moan. I could feel her body tensing, her breath coming in short, sharp gasps. I knew she was close. I continued roughly sucking on and pinching her nipples. Then, with a loud moan, she came, her body convulsing as she rode out her orgasm.

Allison's eyes were locked onto mine, her chest heaving with every breath she took. I could see the desire in her eyes, the need, and it only served to fuel my own.

"Sit down," I commanded, my voice low and firm. Allison didn't hesitate, lowering herself back onto my lap, her legs straddling me. I could feel the heat of her pussy through my jeans, and it was driving me crazy. I reached up, grabbing the hem of her crop top, and pulled it off in one swift motion. Her tits bounced free, and I couldn't help but groan at the sight of them.

"Fuck, Allison," I said, my voice hoarse with desire.