The third chapter of a true story that happened to me a few years ago. All names and relevant information has been changed to protect privacy. I would love some feedback in the comments or DM.
“Sorry Man, I don’t have any money” I lied.
I was standing on one of Portland’s trendier neighborhood’s streets, waiting when a homeless person had approached me.
“Have a good day…” he mumbled, wandering off into the evening’s gathering darkness. These people were as integral to Portland’s urban fabric as roses, bikes or beer. In truth, my wallet was straining with cash. I had swung by work after class and picked up my weeks’ worth of tips for tonight. It was date night.
Checking my phone, I saw Alyssa’s message: “Be there in 5! My friend is lost lol”.
“No worries, do you need the address again?” I texted back.
It had been 2 weeks since I had last seen her, our date postponed by a surprise visit from my parents who insisted on dragging me to a family reunion in California. Now we were finally having our second date. A fancy one at that; she had suggested we get dressed up and make it fun, so in the spirit of the evening, I had dusted off my sport coat, collared shirt and cleaned up fairly well.
I smiled to myself as I waited near the restaurant, a bouquet of fall flowers in my hand.
Just as I was starting to feel the October chill, a Toyota Rav4 pulled up across the street and came to a stop. I saw the door open and a familiar flash of black and pink hair popped out. I caught the faint laugh from the driver who then looked at me, smiled and waved before pulling away revealing Alyssa. I instantly smiled; a grin brought on by her mutually electric expression as we made eye contact. She stood on the curb, waiting for a break in traffic to cross. Her hair was pulled up in a tight donut on the crown of her head, her glossy black hair streaked with pink highlights. She wore a black sweater over a silky, shimmery light pink dress that spoke in a simple elegance that balanced exhibition and imagination, it must have been expensive. Her outfit was drawn together with her shoes. Light pink wedge sandals with black trim. This girl certainly knew how to dress herself.
“Hi!” I smiled as she trotted across the road “You look wonderful!” Up close I noticed all the detailed effort she had put into her appearance. Her earrings and necklace complimented each other, glittering in the evening light.
“Thank you! I tried!”
“These are for you, lovely lady” I said with a flourish as I presented my bouquet to her.
“Wow!” her mouth dropped open in shock “These are amazing!” She looked at me with a dewy-eyed expression. “Nobody’s ever given me flowers before…”
I smiled back, proud of myself for thinking of the spontaneous romantic gesture at the last second. “I’m glad you like them”.
Stepping closer, she kissed me hard. Her lips pressing against mine while her hand grabbed the front of my jacket and pulled me in. It only lasted a second but made my heart jump feeling her against me. She stepped back and smiled, flashing her braces. I had been waiting for that moment all week with great anticipation.
Alyssa had driven with her friend to Roseburg to get tattoos, and conveniently been able to get her braces fixed after breaking them the week prior. I hadn’t thought much of it until I had gotten a snap chat from her from the orthodontist office, asking what color she should get while holding a large key ring of all the different colors they offered. I had assumed she’d go with clear again as her braces were ceramic and designed specifically to blend in with the enamel of her teeth. From a distance, one could barely notice them except for the thin steel wire spanning her smile. I had suggested baby blue, partly because I had heard it didn’t stain as easily, but mostly because I thought it would be cute and she wouldn't be so bold as to choose a brighter color. An hour later she sent me another photo announcing she was “all tuned up” while puckering, blowing me a kiss. I had tried to seem nonchalant when asking what color she had chosen, and was teased with “find out on Friday ;)” which had driven me crazy, she was such a tease.
In her beaming smile I saw that she had picked a bright pink that shown almost iridescent in the low light of an October evening. My stomach flipped and I felt a twitch in my nether regions. I was turned on almost instantly. They matched her outfit and complimented her hair. This girl really knew how to accessorize.
“So, where are we going?” she asked, bringing me back to the moment. “I’m so hungry”
I swept my gaze around to the little Italian place on the corner. “Right this way” I gestured, and we set off down the block making conversation about the week.
***
“So, How was work today?” I asked as we sipped sparkling water in the dim light of the restaurant. Alyssa rolled her eyes as she sipped her drink.
“Uhhg” she scoffed “I’m pretty fed up with my manager.”
“Uh oh, what’d he do this time?” I asked as the waiter placed a basket of bread between us with a dish of oil and vinegar. I smiled at him with a nod of gratitude.
She huffed, grabbed a slice of bread a tore it half with an exaggerated motion that conveyed her emotion. She looked cute when she was fired up. Her lower lip stuck out in just the slightest pout and her dark eyes were energized.
“So you know how last week I texted you about what he said to Meghan? Well, she reported him to the owner, and then he came back to us all with this total bullshit apology, saying something like ‘I’m sorry if anyone felt uncomfortable…’ which, one, is not a real apology, and two! She wasn’t even at work when he said it!” her voice was somewhere between a stage whisper and a hiss. “Then literally today, on the day he was supposed to take lead on cleaning after close, he decided ‘he didn’t feel well’” she wagged her fingers in mocking air quotes “and so Jessie and I had to clean out the ovens again! I’m just so over him.” She slumped back in her seat and took a large bite of bread, looking dejected.
“Wow, I’m surprised he tried to apologize without her” Did you tell Meghan that he pulled this stunt on her day off?"
“Yeah, she was pissed. I told her to mention to Marissa next time she’s in that he hadn’t apologized yet.”
“Did Marissa tell Meghan that she’d make him apologize?”
“I don’t know…” she frowned. “I’ll ask on Tuesday. Sorry for the total rant.”
“Don’t worry about it, besides, my work is so boring, I need some drama” I smiled at her, raising my bread in a salutation. “To your manager, may he be fired before the month is out!”
“Lets hope so!” Her smile returned to her face, dimpling her cheeks as she in kind raised a piece of bread and we laughed.
Dinner passed with a laid-back ease that we both could feel; comfortable in each other’s company, our barriers slowly lowering and intimacy growing. I found Alyssa very attractive, physically, but also intellectually. Perhaps this was the beginning of feelings, of emotional intimacy. Something that had conspicuously been absent from my last relationship. Could I dare think that word around her? This was only our second-ish...(third?) date. Though we texted frequently, almost every day, talking about whatever annoyed us at work, fun things we did throughout the week or drama in our friend groups, this was really only the third time we’d seen each other face to face.
I pondered these thoughts and more as we chatted over the seasonal pumpkin pasta with pork sausage, red peppers and a squash-based sauce that somehow blended the flavors of all ingredients perfectly. Alyssa was easy to talk to, fun to be around, made me laugh. I was curious how she felt about me, yet it felt too soon to be asking these questions. For the moment, I was happy, and that’s what mattered.
“Thank you so much for dinner, it was incredible” Alyssa said as we walked down the bustling Friday night sidewalk. “That’s so much better than anything from the dining hall.”
“I sure hope so” I replied, wrapping my arm around her waist, eliciting a giggle “That cook looks like he spent at least ten percent less time in jail”
“Stop!” She gasped in feigned outrage “That’s so mean!” I gave her a look and we both laughed.
“Where are we going next?”
“Well, I had two choices for us picked out. Ice cream or cake?”
“Oooh! Ice cream for sure!” she tugged on my coat.
“Perfect! I hear the October flavors are something exciting!”
The walk to the ice cream parlor wasn’t far, we took our time in the cool fall evening. The sun had set and lights were beginning to flicker on, casting large orange pools of light along the street. Feeling bold in the moment, I reached down and took Alyssa’s hand in mine; her hand flinched at the unexpected touch before softening and interlacing her fingers with mine.
“That was cute” she said with a soft smile, “Very romantic”
“Thanks, I try” I winked and squeezed her hand. She squeezed back.
We walked hand in hand past the closed store fronts, our reflections undulating in their dark windows. A glass shop, a pizza place whose workers were mopping in the dim light from the kitchen, a pet store that filled their windows with posters of smiling dogs eating the newest dog food brands. It was very quaint.
“What kind of dog do you want when you get your own place?” I asked
“Ooooh, that’s tricky… all the dogs?” she laughed “I can’t decide, they’re all pretty cute.”
“Even chihuahuas?” I teased with a raised eyebrow
“Okay… you know what,” she brandished a finger accusatorily in my direction while smiling devilishly.
“What? You said your uncle had several!”
“Yeah, and I hate them! They’re so small and annoying and yappy”
Shaking my head while egging her on I depended my gentle antagonism “I just can’t believe you’d turn on your family like that… tsk tsk…”
“Are you saying that because I’m Mexican?!” she gasped in false outrage “Because I’ll have you know, I’m only half!”
We had stopped at a corner and waited for the ‘walk’ sign as our conversation had continued. Her hair whipped around her face in the wind as a large truck passed. “Half Mexican, and 100% adorable” I teased as I brushed her hair from her face with my fingers, leaning in and kissing her on the street corner. Her hand found my cheek as I pulled her in, our lips softening into our embrace. My arm wrapped around her exposed lower back as her tongue intruded my mouth in a gentle, but firm feeling that I felt down my spine and in my nether regions. With a deep breath we broke apart, I stepped back to see her smiling her soft, ‘doe-eyed’ smile I had seen a few times prior; it was an irresistible look. Her smile revealed her top teeth and though it wasn’t as apparent as earlier, the new color of her braces was visible.
“I like the color you chose” I said quietly, nodding towards her, my eyes flitting down to her braces before resuming my gaze into her deep brown eyes.
“Yeah? It’s a bit more vivid than I wanted but honestly, I think the pink is super cute!” She smiled up at me, giving me a perfect view of her braces, both top and bottom. Her clear brackets were now ringed with a hot pink band that held her wire in place, accentuating her braces from a barely discernible detail of her appearance to a bright accessory.
“And you accessorized expertly” I added as I gestured to her outfit.
“Thank you, I learned it all on TikTok” she laughed as we crossed the street.
“Oh lord, I spend waaayyyyy too much time on tiktok”
“Really? You’re not ‘too old’ for tiktok?” she accentuated with air quotes while giving me the side eye. “What’s your tiktok?”
“No way, I’m only like a year or two older than you.” I replied while I pulled out my phone and opened the app as we walked along. “Here, follow me”
“Okay, but don’t be surprised if I spam you. My friends complain that I send them like five hundred videos a day.”
“I look forward to it. Ooooh, what do we have here?” Her profile had about 30 videos on it, but one of the more recent thumbnails was her in a pretty skimpy outfit, it was clearly a thirst trap.
“Oh God” Alyssa muttered as she covered her gaze with her hand. “I forgot about that. Give me that!” she swiped at my phone.
“No, no, I want to watch this” I teased, holding my phone up above her reach.
The video was short but showed her in a baggy sweatshirt that she pulled into a seamless transition to expose her curvy figure in a black lace lingerie set with thigh high garters as she winked at the camera showing her ample cleavage.
“WHOOAAAAA MAMA” I hooted as she protested, “Muy caliente amiga”
“Oh God, I don’t need this” she muttered as she walked down the sidewalk away from me.
“Where do you think you’re going missy?” I wrapped my arm around her shoulders as I caught up to her.
“To get some ice cream you sex fiend!” she half joked.
“Only for you” I replied and we continued our walk joking and flirting.
A block later as we passed a row of darkened store windows, I spotted an alley up ahead that gave me an idea. As we walked passed, I grabbed Alyssa’s wrist and pulled her with me.
“Ow!” she complained as she was somewhat roughly pulled into the alley and out of the streetlight. “What are you doi-”
I cut her off with a passionate kiss. My hands on her neck, pulling her face to mine, my lips pressed against hers. At first firm but softened as she understood my motivations. I had to kiss her, I mean really kiss her. The combination of her outfit, flirty texting the past two weeks and bright pink braces were driving me insane. My tongue pushed its way into her mouth which elicited an audible moan from her as she gently played with it between her teeth. I was lost in her smell, the sound of us breathing together and her hands on my waist. That changed as I pulled her in, and our bodies pressed against each other, hoping to escalate this, I ran my hand down her back, across her very nice ass and gave it a squeeze as she moaned into my mouth. I felt her arm shift as she moved to mirror me and I felt her hand run across my already hard cock.
“Mmmm” she moaned before pulling away from our embrace.
“Looks like I found something exciting” she said with a wink before moving to reach down my dress pants.
“Whoa, right here?!” I asked incredulously,
She had a devilish look on her face now, a look that hinted at the depravity underneath her well-manicured facade. A desire and hunger I had discovered on our last date when she had let me almost mercilessly fuck her throat. “Why not?” she asked, sinking slowly towards my crotch “Its nice and dark.”
Before I could argue, she pushed me backwards against the wall of the building in the alley, joining an overflowing cardboard dumpster and a stack of produce crates. Kneeling before me, she deftly pulled my fly and grabbed my cock in her right hand, stroking in while looking up at me. “Fuuuuckk… Alyssa….” I moaned quietly in the dark. It was almost impossible to see her. The only light came from the street lights down the alley, illuminating only the closest half of her face in a moonglow light.
“Mmm, I missed your dick” she whispered as I felt a bead of spit slide from her lips to my cock, lubricating her hand and making my knees weak. “I know you missed me too, huh?” she cooed up at me, a fake innocence in her voice egging me on, riling my sexual appetite.
“Oh yes baby,” I smiled down at her, her hand running up and down my shaft.
“What did you miss the most?” she asked in barely a whisper as I felt her tongue rub the bottom of my head, making me shudder.
“Definitely that smile” I whispered back. Both to be sweet, I did like her sunny attitude and the smile that accompanied by it, but in the literal sense I missed the exhilaration of catching glimpses of her braces when she spoke. “And—” before I could finish my thought, she wrapped her mouth around my cock, leaning forward and giving only the view of her bun while she sucked me deep into her mouth. My head could feel her throat as she pushed herself down my shaft.
“God!” I rasped as she began to suck my cock in earnest. Her bun rocking back and forth in the darkness. It was hard to see anything but stars in my vision as her hands worked my shaft, her tongue flailing on my head as I did my best to keep my footing and my legs from buckling. She worked feverishly, taking me deep then backing off and playing with my cock on the tip of her tongue, looking up at me. It was so dark I could only barely see the glitter of the streetlight reflecting in her eyes when she looked up.
“You like my smile?” she finally asked. “You think its sexy?”
“Yes!” I replied, perhaps a little louder than I should have. In a quieter voice, I continued: “It’s so sexy”
“Good baby, goooood” she cooed as her hand pumped my cock. I was hunched, my leg muscles tightening as an orgasm was fast approaching. “I’m glad you like it. Even with my braces?”
“Yes” I gasped “I love your braces”. Oops! My mind was reeling, how had that slid out of my mouth? I started to feel the hot flush of shame in my cheeks. I hadn’t meant to confess that so boldly. My braces fetish was mine, and mine alone. Or at least it had been. Before I could verbally recover from my Freudian slip she had once again plunged my cock into her mouth, sucking hard and making my vision flash, rendering me speechless. This had gone from a flirty make out to a hardcore back-alley blowjob in not 10 minutes.
“Good” she finally replied in a silky voice as her mouth came off my cock. I could barely see the strands of spit stretching from my cock to her mouth. “I like that. Did you like my new color?” Her hand still effortlessly working my shaft in a corkscrew motion.
“Mmm-hmm”
“Did you notice I teased you with it? I wouldn’t show you my braces till now, so you’d have to wait?”
“Mmm-hmm” I strained, I was so close.
“Yeah? I bet that drove you crazy, huh?”
“Yes!” I gasped. “I’m gonna cum!” I was fast approaching an orgasm.
“Yes baby, yes, cum for me!” she beckoned, adding her second hand to my cock. “Fill my mouth with cum!” She had taken complete control of the situation, I wasn’t fucking her face anymore, she was jerking me off. Like an escort in a hotel room she had me wrapped around her finger to a degree no girl had ever done before.
“Or….” She said in the same silky voice “Do you want to cum on my cute… pink… braces?” she punctuated every last work of her sentence as she rubbed my sensitive head on the rough, almost sharp brackets. My eyes screwed shut, I could see in my minds eye what was happening, I doubled over and exploded.
“Oh!” she gasped as I came like a shotgun. I couldn't see anything, I could barely hear my own muffled grunts and strained moaning as I emptied my balls onto her smile. “Nnnnnnnn-hnnnn” she urged through gritted teeth. As her hand pumped my cock, covering her braces in cum. My eyes rolled back as I reached out and grabbed the dumpster to my right for support, breathing like I had run a marathon.
After a minute of silent darkness, punctuated only by my labored breathing, her voice came through the darkness.
“Holy shit, that was so, so, so hot…”
I heard her getting to her feet as I straightened up and tucked my already softening member into my pants before fastening my belt. “Yeah? It wasn’t too much?” I asked tentatively, afraid that my dark sexual secrets were fully realized and I was about to be ostracized.
“Haha, the only thing that was too much as how much you came” Alyssa joked as she kissed me on the cheek. “We should do that again.” I breathed a sigh of relief as we walked out of the alley together, God I was lucky.
“Should we still go get some ice cream?” I asked rhetorically
“Absolutely” Alyssa smiled as we stepped back into the light and on the sidewalk “And then to your place, I have a surprise for you….”