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First Date with my Shy Co-worker

ashwanikobo01
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The average realized release rate over the past 30 days is 7 chs / week.
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Chapter 1 - First Date with my Shy Co-worker

On days when I would space out in the office, my eyes would often drift over to Alyssa. Honestly, she wasn't a bombshell--small breasts, skinny as a rail, with an average looking backside. But she was exactly my type: "nerdy cute"! Her red hair flowed over her shoulders when she took out her butterfly barrette. Her petite figure, emphasized by tight sweaters tucked into her jeans, complemented her reserved personality. The top of her cubicle was decorated with Disney pins and plushies.

I loved how she expressed herself, despite her shy nature. Needless to say, I quickly developed a crush on her--her little quirks, the way she would make eye contact and then quickly look away, embarrassed--she was absolutely adorable.

After a few months of getting to know her through finance team lunches and project work, I finally decided to ask her out. She looked surprised, and her blushing face as she accepted warmed my heart. I suspected she might have had a crush on me too, but this was the first time I felt confident enough to take the leap.

Our first date was pretty light, just mini golf followed by ice cream. From all the horror stories I would hear about first dates from my female friends, I always tried to make women feel safe and comfortable, never pushing the line too far.

She was so shy at first, hardly uttering a word, wrapped in her beige cardigan that hung off her shoulders, and black shorts with a cute little belt to go along with it. Holy shit was she precious! I had to resist popping a boner when I saw her walking to the car. I gave her a hug when she got into the car and the material of her cardigan felt so nice, hinting at her cute body beneath it.

She certainly shouldn't quit her day job when it comes to mini golf, although I still let her win. Our conversations started flowing a little easier with each hole we completed until we were playfully touching eachothers arms and laughing by the time we finished. Ice cream was good too, I did my usual cookie dough on a cone while Alyssa got rum raisin. Honestly, rum raisin might be my least favorite flavor and I hid a cringe when I heard her order it but it was no big deal.

We sat at the table talking for hours while she told me all about the new Disney pin collection that had been released, and how she adored the new kitten she'd soon be adopting. Thankfully I grew up in a home full of Disney loving sisters and 2 cats so this was an easy win for me. I wasn't that interested in either topic to be honest but seeing her talk about the things she loved with passion, I couldn't get enough of it!

By the time I brought her back to her apartment it was already dark out. As I'd always been taught, I walked her to her apartment trying my best to make her feel safe and end the date on a high note. She even let me hold her hand walking up the stairs to her 5th floor room. As she let go of my hands and unlocked the door to her apartment, I was nervous but still decided to make my move.

"Hey Alyssa, I had a really fun time with you today" I said as my palms began to get clammy.

"Me too Ryan, thanks for an amazing first date" she said blushing at me and smiling while tucking her shiny red hair behind her ear and opening the door.

"I'd really like to take you out again sometime" I expressed taking a subtle step closer to her.

Alyssa stepped away from the open door until she was less than a foot from me.

*SKIP*

"I'd love to" she responded softly, leaning into me 10% while I did the other 90 as our lips met. Her lips felt so soft against mine like a perfect pillow. Each kiss produced the perfect smooching sound, and her petite body felt so right in my arms as I wrapped them around her waist.

As we pulled away from the kiss slowly, I got a look at the light in her bright blue eyes. I always loved when I could make a cute girl feel genuinely happy. Knowing how shy and timid Alyssa could be I didn't think about pushing any further than this. I figured she would need some more time before we actually got physical.

"We'll have a good night Alyssa, I'll see you in the office tomorrow" I said as I started to turn around.

"Oh no no no, I don't think so! I've been waiting way too long for this!" She stated with more authority in her voice than I'd ever heard her use at the office.

It all happened so quickly. She grabbed my shirt with both hands and pulled me into her apartment slamming the door behind us. She landed her back against the door with me pinning her and we began furiously making out, her tongue seeking out mine with an uncontrollable hunger. Holy shit was she a good kisser, she did it exactly how I love it. Sloppy, lots of tongue, each break in between with an almost too hard bite of my bottom lip. I'd never heard moans of such desire come from a woman, like music to my ears.

"Pull my hair..." she whispered to me. She didn't have to tell me twice. I grabbed a fist full of her precious red locks and began kissing her even deeper than before.

"Harder..." she whispered to me through her moans. I was shocked but I wasn't going to argue. I pulled her hair almost as hard as I could from the back of her head. Part of me was afraid I would hurt her but my fears were cast aside when I heard her growl out a primal "ohhhh fuuucckkk yyyeeaahhh" as she started to rub the throbbing bulge over my jeans.

I was desperate to touch her body too! This timid, geeky girl turning feral was sending a crazy surge of horny energy throughout my body. I thrust my hands under her top, running them up to her breasts as my heart thumped throughout my body. I was shocked when I felt it, throughout our whole date she wasn't wearing a bra!

I started massaging her cute little a cups hard. She must of loved that as she let out the hottest of gasps. Her tits felt amazing in my hands and her nipples stuck out hard, unable to hide how horny Alyssa had become. I was enjoying myself, yet something felt different. There was a different hardness around her nipple.

Alyssa noticed my shock and produced a seductive look that I didn't recognize. She reached down to the bottom of her cardigan and slowly pulled it up over her head leaving her topless.

"No fucking way..." I said out loud as my jaw practically hit the floor.

"Don't be suprised...I've had them pierced for a long time now" she said unzipping my pants. My eyes were fixated on the silver shaft sticking out with similar colored little balls at each end. I'd never been with a girl that had pierced nipples and the idea of it made my mouth water. "Go ahead..." she tempted me. "Suck on them....i know you want to"

I pressed my mouth to her nipple, teasing my tongue in a slow circle around her areolas before moving to the metallic edges. The shivers through her body as my mouth licked her sensitive, pierced tits caused me to shudder as well. Her heavy breaths and little quivers spurred me on even more. At this point she's pulled my jeans and boxers down, and was teasing the tip, spreading my pre cum with her thumb.

"Mmmm is that pre cum baby?" She asked while increasing the intensity of her teasing.

"It is...I've been thinking about this for so long Alyssa" I said nearly breathless for her.

"Not as much as me Ryan, you're not the only one leaking here" she answered as she undid her belt and unzipped her shorts. I happily took the hint and reached my hand inside, guiding it below her underwear. "Oh my god...Alyssa...your soaked!"

"I can't help it when I'm around you...you're the reason I always...have to pack an extra pair of panties for work...every...day"

I slipped 2 fingers into her and started rubbing her with the old, reliable come hither motion. She closed her eyes and bit her lip hard, whimpering with each thrust of my fingers. Her entire mound and her panties lying on the back of my hand were coated and sticky. It felt like I had dropped my hand into soda syrup as her nectar kept dripping and dripping coating my whole hand. I've gotten to know Alyssa well over the past few months but this side of her completely caught me off guard. God I loved it!

"You like that Alyssa? I love how wet you get for me"

"Ahhhhh ohhh myyy god yes! D-Don't stop!" She cried out as she dropped her hand to the shaft of my cock and started stroking me. The look of ecstasy on her face was driving me crazy. Biting her lip, eyes rolling back, face scrunching like it felt so good she couldn't help it. I was enjoying the view as my fingers filled her and my mouth sucked on her sensitive, pierced nipples.

"K-Keep going Ryan...I'm gonna cum..." she whimpered out, barely audible to me. Her pussy lips were noticeably quivering and her wetness ran down my wrist rapidly as she leaned her head on my shoulder.

"That's it...right there...right there...right there!...AAAAHHHHHHH!" She screamed out, loud enough that any of her neighbors could hear, as her pussy contracted and she bit my shoulder hard using her hands to stabilize her quivering body as the strength was zapped from her shaking legs.

We held eachother breathless as the aftershocks ran through her body. It was a sweet silence, just both together breathing heavily, my wrist sore from the preceding activity.

"Damn Alyssa, I never expected this! You always came off as so innocent to me!" I said shocked.

"I-I'm shy...not innocent...Ryan" she responded to me with an adorable fake pouty face.

"Well thanks for the clarification" I responded chuckling a little. When I did, Alyssa looked up at me, eyes portraying an insatiable lust, with the naughtiest of smiles. She grabbed my dick in her hand hard, no doubt feeling it throb relentlessly for her.

"Let's go to my room...I NEED to cum again...and I wanna cum while you're fucking me...and filling me up with all that pent up...hot...cum!"...

n our frenzied, lust drunk state, we bowled through Alyssa's bedroom door, shedding the remainder of our clothes throughout her apartment. My pulse was thumping through my entire body with anticipation as I pulled her naked body to me, swiftly slamming the door shut. Every inch of her body was like a touch of heaven, every drag of my fingers sending shudders down her spine.

"Let me get a taste for you Ryan" she whispered as she got on her tippy toes and started to kiss softly down my neck...to my chest...to my stomach...until she was face to face with my stiff cock.

"Fuck Alyssa..." I said breathless as she began to swirl her tongue around the tip.

"I can't believe you, hiding this perfect, thick cock from me for so long" she said as she licked her lips hungrily.

Her mouth gave my tip a little kiss before it widened and slid down until every inch of it was in her throat. She gave me one long teasing suck of the entire thing before she looked up at me with those bright blue eyes. "Don't be afraid to be rough with me, the dirtier you talk...the hornier I get...use me!" she explained giving me a precious little wink.

I'd never been the type to be super rough with a girl, but hearing those words come from my supposedly quiet, shy crush from the office awoken something in me.

She thrusted her mouth back onto my cock, taking me deeper than any woman I'd ever been with. I grabbed a fist full of her hair and pulled hard, just like she liked it, increasing the speed of her mouth across my shaft.

"You dirty little whore, I bet you were thinking of this all day weren't you?" I said to her seductively as I pushed the back of her head, increasing her speed further. "I bet you touched yourself all the time at the office, thinking of me fucking your throat!" I said as I began to thrust into her mouth.

"Mmmhmmm" she said enthusiastically muffled by my cock in her throat. Alyssa no longer pretended to be delicate with my cock. The sensual blowjob had quickly turned sloppy with her saliva coating my cock, deep throating me, and her arms wrapped around my thighs for maximum balance. Truthfully, dirty talk was fairly new to me but whatever I was coming up with seemed to be working.

"That's right Alyssa, show me how not innocent you are, show me the cock slut side of you!"

"Mmmmmm!" She purred sending vibrations throughout my whole cock. I was loving it, Alyssa was like my own personal sex goddess. She started sucking even harder now and had brought one hand down to her slit all while I kept fucking her throat. Her horny juices dripped onto the hardwood floor while her mouth did the same as her spit dripped down my dick. The sound of her gagging on my cock rippled through my head pleasantly, as I added my other hand to her head.

Her body started to shudder as she rubbed herself between her thighs, starting to slow down just a little, giving into her own pleasure. Her cute little pierced tits bounced up and down and her body stiffened as she began to rub harder and harder. This sweet, shy Disney pincess was so worked up she couldn't help but touch herself while she slurped my dick. That's when I decided to make my move.

I brought my hands down to her shoulders and pushed her down to the floor on her back. I went down to meet her, breathing hard, her pierced chest rising up and down rapidly in anticipation.

"Ooohhh fuck Ryan, I thought you were a gentlemen. What happend?" She chuckled teasingly as I stared into her horny eyes.

"I am Alyssa, but the sweet redhead from the office wanted to be used!" I answered as I teasingly licked around her nipples.

"God damnnn...plleeassse dooo" she replied as her breath got choppier as my tongue ran down her naked body until I reached just above her aching clit.

"She also has a greedy little pussy...couldn't help rubbing it while my cock was down her throat". My words sent shivers throughout her, forming goosebumps all over her aroused body as my words landed on her sensitive clit. "Let's have a taste shall we?" I said as my tongue began circling her clit while her body jerked involuntarily.

"You're a squirmy one Alyssa, we can't have that!" I stated wrapping my arms tightly around her thighs and going to town on her aching pussy. Her nectar practically drowned me as she ran her hands through my hair. I continued to eat her pussy like it was the first meal I had in weeks. Her bodies jerking movements and her ecstatic moans only motivated me more to devour her dripping slit. If my hands weren't holding her thighs apart there's no doubt I would've suffocated, but I couldn't give 2 shits!

"R-Ryan...if you...y-you're gonna make me c-cum again!" She yelped as her hands left my head and returned to her sides, clawing and leaving scratch marks on the hardwood floor beneath us.

"Cum in my mouth Alyssa, show me how good I make you feel!" I said looking up at her face from between her legs. The adorable scrunch of her face was there and she had bitten her lip to the point a small drop of blood began forming. Her entire body erupted in climax, vibrating violently as her pussy clenched and released a puddle of her sweet juices soaking my face. Her legs had a mind of their own shuddering and shifting haphazardly over and over again.

"Holy shit Alyssa, who would've thought of all people, you'd be a squirter?!" I said lifting my head up, watching her continue to quiver while her mouth released inaudible gibberish. As she caught her breath and her body began to slow its pulsating she responded, "o-only w-when I'm really p-pent up!" She explained collapsing back to the floor, her ass landing in the puddle of her own cum.

"Interesting...I'll keep that in mind" I said. "I think it's time for the main event" I said wrapping my arms around her and picking her up like she was light as a feather.

"Baby...you want me on all fours on the bed?" She asked

I looked deeply into her lust filled blue eyes again. "You told me you wanted to get drilled like a little whore, and that's what I'm gonna do!"

I carried her over to her desk in the corner and threw her onto it, her whole back was quivering in anticipation. I took my cock in my hand and ran it up and down her pussy, relubing it with her nectar over the dried saliva from before.

"Do you want this dick Alyssa!" I asked her teasingly, full well knowing the answer.

"I want your dick!" She stated, the desperation in her voice growing as she shook her ass, tempting me.

I brought my tip to the opening, barely penetrating it. "Are you my little cock slut?"

"I'm your little cock slut..."

"Good girl..." I said as I thrusted my entire length into her and grabbed a fist full of her hair again.

"Fuuccckkk, thank you Ryan! Thank you for this perfect cock!"

I started pounding into her as Alyssa helplessly clawed the edge of desk while my dick filled her needy pussy. With each thrust her arousal dripped more and more onto the floor below.

"You little skank, your little kitty is leaking already!" I say to her as I slap her ass hard leaving a red mark in the shape of my hand.

"Oh my god! Keep spanking me Ryan!" She practically screamed as I continued sending painful ripple after painful ripple through her sweet ass.

Alyssa started pushing her ass back and forth with my cock, trying to get me as deep as possible. "Jesus Alyssa, are you a little pain slut too?!"

"Y...yeah it m-makes it way m-more intense!" She cried out in between her sweet moans and the slurping sound of my cock filling her saturated pussy.

My hand released her hair, landing on her shoulders. I reached around her chest grabbing both her nipples in my thumb and pointer fingers, the rest of my hand pressing into her sensitive little a cups.

"And here?..." I asked

"G-grab from the root...*ahh*...*fuck*...and p-pull as hard as you can!" She begged as I started to pound into her harder and harder. I did just that, pinching and yanking them as hard as I could. The puddle of her wetness was beginning to soak my feet even more as the sensation on her nipples increased her wetness. The intensity of the whole situation was electric and my cock was throbbing, my inevitable climax nearing.

"Choke me..." I heard her whisper through her out of control moans. I wrapped my hand around her neck, lifting her chin up slightly, feeling her drool run down my fingers.

"Harder! I can take it!" She demanded as her pussy hugged my cock tightly. I'd never done this before and again I was worried I would hurt her, but if that's what you want, that's what you'll get... my sweet Alyssa!

I clenched my hand around her neck as hard as I could, forcing pleasant gags from Alyssa's mouth. I was only seconds away from cumming and from her toes standing up and her legs jiggling like jelly, I could tell she was too.

"I'm gonna breed this pussy Alyssa! Do you want it?" I asked pounding into her as hard as I can making her ass jiggle rapidly and delightfully.

"Yes baby!" She said as her knees started buckling and her claws dug deeper into the desk.

"Say it baby! Yes what?"

"Breed this pussy! Give me all that hot cum!"

"Here it comes baby! Take it all!"

"That's it! Don't stop! Don't stop! Don't stop!...IM CUMMING!" she screamed as my cock released its full load into her, in turn her squirting pussy erupted, thrusting it back out, our cum uniting together at our feet.

I lifted her up by the neck and moved my palm over her mouth, muffling her moans and screams of ecstasy. Her entire body quivered in my arms, her legs shook haphazardly, her entire back vibrated, and her abs tightens up again and again as the orgasm short circuited her body. Her pussy lips continued contracting against my cock, not letting a single drop of the warm cum she craved remain in my balls.

As the rippling of pleasure began to fade she put her hands back on the desk, hunched over, her breath heavy with satisfaction.

I picked her up, threw her onto her bed, and proceeded to have the sloppiest make out session of my life, a thank you from Alyssa for making her cum hard thrice!

As I pulled away slowly, a string of our combined saliva dropped onto her chest and smiled up at her.

"You know there's a great Chinese place near here, if you worked up an appetite baby" I asked her as our primal lust faded.

"Dragon house? I fucking love that place!" She responded with glee, her returning sweet, shy girl smile inked on her face.

"I'd kill for some general tso's, ice cream is t really a meal after all!" I responded playfully running my hands through her hair. She shuddered again, her body still sensitive.

"Baby after the pounding you just gave me you can get whatever you want...it's on me!" She responded as she nuzzled into my neck letting out a happy, satisfied sigh.

When I got to the office I felt like I was on top of the world. It was a Friday, beautiful day out, I slept great, and for the first time in years, I came into the office early.

I plopped down at my desk, coffee in hand ready to take on the day. Ok to be honest, like I said, it was a Friday, so I knew we wouldn't be doing jack shit once the afternoon hit. That was fine by me, more time to talk to Alyssa, maybe take her out for a nice long lunch at Panera, get to know her a little more.

I couldn't wait to see her when she got in! I could picture it: her walking up to her desk, catching a glimpse in my eyes, smiling back at me blushing, memories of the night before rushing back through her head. She'd do that precious little hair tuck she does behind her ear. That's what I thought would happen...until I looked on teams. Alyssa had an out of office icon over her name...my good vibes crumbled right in front of me in that instant.

SHIT! I hope she didn't skip work cause of me. I tried not to push too hard with her but things got well...passionate last night. I hoped I didn't embarrass her or make her feel uncomfortable. I thought things went really well. I mean shit, good sex, Chinese food, a little bit of weed and avatar the last airbender. That sounds like an A+ date every day of the year, at least in my book!

I mean she seemed so comfortable last night with me. She was falling asleep in my arms in bed after all. My anxiety was growing, I needed to get in contact with her. I quickly put in to take the afternoon off, and texted her.

"Hey Alyssa, listen I had a really great time with you yesterday and I noticed you weren't in the office. Could I come visit you this afternoon? Just want to make sure everything is ok"

I waited an hour...no response...2 hours...no response, finally as I was fidgeting at my desk, desperately waiting for the clock to strike noon, I heard a buzz from my phone. "Feel free to stop by" appeared on my screen.

Damn it! That wasn't exactly enthusiastic but I needed to see her. My nervousness would not let this go ignored. As soon as that clock hit noon, I jumped up from my seat, not waiting around to make small talk with anyone. I only had Alyssa in mind. I sped over to her apartment complex, completely amazed I didn't get pulled over and rushed up the stairs to her apartment.

As I got to her door with my heart in my throat, I pulled out my phone and texted her. "Here"

"Doors unlocked!" She replied.

I quickly turned the knob thrusting myself into her apartment. No sign of her. I walked over to her bedroom and knocked on the door.

"Hey Alyssa, can I come in?"

"Yes, come in" she replied.

As I opened the door I found her laying in her bed. She was wearing her glasses, a big baggy plain t-shirt with no bra underneath showing her piercings, her red locks were messy and tangled, and she was wearing fuzzy pj pants with stitch from lilo and stitch plastered over them making different funny faces. She gave me a worried smile as she looked up from the Nintendo switch she was playing. It was quite the contrast from yesterday but she was still beautiful in my eyes.

I approached her bedside slowly, anxiety running through my head and my palms sweaty. "Taking a sick day?" I asked as I stared down into her sad blue eyes.

"Something like that" she replied looking nervous. I loved the sex but the nervous shy side of her really is what made me fall head over heels. But in this moment only genuine concern and fear came over me.

"Is everything ok?" I asked concerned reaching out and running my fingers through her hair.

"Yeah I'm fine"

"Alyssa..." I responded knowing she had told a lie.

"Ok fine, I'm not ok. Have a seat" she said motioning me onto the bed. "Promise you won't judge me?" She asked holding tears in her eyes.

"Of course!" I responded laying down and snuggling up to her.

"The truth is I'm not sick...I...I had a panic attack this morning" she said with her tears starting to run down her cheek. I brought my thumb below her eyes wiping her tears. "Why?...do you regret what happend last night? If so I'm really..."

"No! Not at all! Last night was amazing! I...umm...I just...I really like you Ryan, I'm just...scared"

"And I really like you Alyssa. Why are you scared" I said in response.

"I just don't want you to think I was too much...some days I'm ready to jump you like last night...but I don't want to give you a false impression of myself. There's other days where I get really down and stuck in my head. I'm scared if I showed you all of me you would run away".

"Alyssa..." I said tilting my head and bringing her in for a hug. "It's ok, I get in my head sometimes too. I don't think you're too much at all!"

"You wouldn't judge me on days I just want to be held...or days where I'm a little more kinky than last night?"

"Not at all. I like you for all of you!".

"And I didn't come off to intense or make you feel weird last night?" She asked, her tears had stopped flowing but her eyes were still bright red.

"Of course not..." I reassured her kissing her forehead and leaning over her. "You should never be ashamed of your feelings or what feels good for you in the bedroom. I'm not here to judge, I just like being with you!"

Alyssa looked up at me, ridding herself of her remaining sniffles. "I really appreciate that Ryan. You're so sweet" she stated nuzzling into me. I knew I'd never be able to get over how adorable Alyssa was. In that moment, all I wanted to do was protect here and make her feel happy.

"Would you like a big spoon for a little bit?" I asked, rubbing her rosy cheek with my thumb.

"I'd like that a lot actually" she said looking down and smiling shyly, the blush over taking her face.

I laid on my side as Alyssa did the same, scooting her ass into my crotch as I wrapped my arms around her. I feel her stomach rise and fall as she let out a relaxed sigh. I just held her close, periodically running my fingers down the length of her red, wavy hair, leading into a little back scratch as I reached the bottom.

"That feels really nice" Alyssa said with a little shiver running down her spine.

"Good baby, just enjoy it" I responded

Eventually my hand did get tired so I just held her, her hair laying on my face. We stayed cuddling like that for what felt like an hour, just at peace in eachothers presence. The more I looked at Alyssa, cozying up to me, calm and relaxed, the more I fell for her. I couldn't help myself. I saw an opening on her neck and instinctively I started planting gentle kisses across it.

Alyssa flinched slightly but didn't say anything. I could feel her breathing get shallower as she began to make the cutest little moans. "Ryyaann...how did you know neck kisses were my weakness" she asked playfully like a frustrated child.

"Everyone loves neck kisses Alyssa" I said grinning. "Like I said just enjoy it". I could see her back shuddering and her body shifting like it almost felt too good.

"Can umm...can you...touch me too" she asked with the slightest hint of embarrassment in her voice.

"You want me to touch you?" i asked playfully, waiting for confirmed permission.

"Yes please...neck kisses...turn me on. You...turn me on" she said softly through her moans.

I could feel a boner brewing beneath my jeans. I loved the horny, feral side of Alyssa, but I also really loved this side of her. I ran my hands under her shirt and started massaging her breasts.

"Ahhh...ahhh...that's really nice" she responded, her body beginning to quiver more under my touch. I ran my hands over her nipples, feeling the cold touch of her piercings and began to lightly tug. Her whimpers were making me rock hard as I caressed her sensitive little pierced nipples.

"Mmmm...you can t-touch me under my pjs too...if you want" she asked in a precious, almost begging tone. I reached down into her stitch pjs, going underneath her panties, landing my hand directly on her mound. She was completely drenched as her legs shifted, spreading wider for me.

"You're really wet Alyssa" I said seductively continuing to kiss her neck while my hands worked on her other most sensitive areas. I slipped my fingers inside of her, completely coating them in her arousal as I started lightly stimulating her G spot.

"It's your fault...you make me horny" she said shuddering under my touch. I loved how her body reacted to me. All I wanted to do was make her feel amazing.

"See Alyssa...being intimate doesn't just have to be primal and intense. It can be gentle and caring too."

Alyssa's turned her body to me so that we could be face to face. Our foreheads touched as I added my palm against her clit as she released a pleasant gasp. Her moans releasing less than an inch from my face was driving me wild. As if your minds were one, we locked lips and began to make out, just like yesterday, but this time it was slow, enjoying every flick of our tongue against the others, dancing in unison in each others mouths.

Alyssa pulled away, unable to kiss, breathe, and moan at the same time. Her eyes closed shut and she pulled my shirt, balling it into her fist. "Does that feel good Alyssa?" I asked her softly.

"Yeahhh...ahhh...keep going...I'm gonna cum..."

That's when an idea sprung into my head. I pulled my hand out of her PJs, laying it on her waste band, her glistening nectar dripping onto them, and looked at her beat red face.

"Mind if I take these off?" I asked raising an eyebrow at her.

"Go right ahead" she said shyly with a sparkle in her eyes.

I pulled her pants and underwear down and threw them onto the floor. I positioned myself so that I was face to face with her begging pussy and started to slowly eat her out. I took my sweet time licking all over before I started swirling my tongue around her clit.

Her heavy breaths were like a perfect harmony as her moans guided me. I lightly nibbled her clit while I stuck my fingers back inside of her. Her body started rocking side to side, and her thighs were quivering next to my cheeks.

"Oooohhh my god! Ryan..." Alyssa let out as she lifted her shirt and began massaging her bare breasts. "That spots perfect...just like that...just like that" she ordered as I saw her face scrunching and her hands squeezing her tits harder. Her breathing picked up heavier as I knew she was close to the finish line. "Ahhhh Ryan..." she whimpered looking down at me enjoying her delicious pussy.

"I'm gonna cum...I'm gonna cum...IM CUMMING!" She screamed as her pussy leaked onto the sheets below it. I held her thighs to lessen the stress of her quivers and I could feel the precum dampening my boxer as I saw her labia clench tightly over and over again.

She was out of breath, shirt in her mouth revealing her tits, beads of sweet forming in her forehead.

"Alyssa..." I said looking into her eyes, chin on her pubic bone "that was incredible".

Through her heavy breathing Alyssa suprised me with her next question. "Can I...can I...blow you?" She asked with her eyelashes flickering up at me.

"You don't have to Alyssa! I just wanted to make you feel good and help you relax" I responded trying to be polite while my cock throbbed in my pants.

"I want to! You can't expect to make me cum that hard and NOT want to suck your dick" she responded with puppy dog eyes. Alyssa, neck kisses might be your weakness but your cuteness was definitly mine.

I stripped off my clothes and laid down on the bed switching spots with her. Alyssa threw her shirt over her head, leaving her completely naked, gorgeous body exposed. She brought herself over to where I was previously laying on the bed and swirled her tongue, reading my precum coated tip.

"I wanna make you feel just as good as you made me feel" she said erotically with glimmer in her eyes.

She slowly brought her tongue down my shaft, letting no part of my cock go uncoated in her salvia. The feeling of her tongue on me made my body shudder just like she had.

"Ooohhh yeahhh, I love that reaction" she stated as she took my cock into her mouth. Ecstasy ran through me as she looked like she was in heaven with it standing firm in her mouth while making eye contact with me. This blowjob was intense, but yet so sensual. She was really taking her time, reading my reactions like a book.

Seeing her naked body taking my cock, genuinely enjoying herself was bringing me right to the edge. I had to let her know that the inevitable was coming.

"Alyssa...fuck...I'm gonna cum" I said softly as she sucked my cock intensely before stopping for a quick moment.

"Cum in my throat Ryan, I wanna taste you" she said putting it back in her mouth. Her tongue movements combined with her bobbing pushed me right over the edge as my legs lifted, filling her mouth with my seed. The way she let out little "mmmm"s sent ripples of after shock through my body as I balled her sheets in my hands and clenched my thigh muscles.

She looked up at me, opened her mouth, her tongue coated my cum, and with one gentle flick, swallowed it whole.

She climbed back next to me and nuzzled her head into my chest. We sat there for a while, taking in what had just occurred. No doubt contrasting our first night of primal passion to the gentle delight of this afternoon. I hated to break the peaceful silence but there was one more thing I had to ask.

"Hey Alyssa..." I asked, her lifting her head from my chest to meet my gaze. Suddenly I was the shy one.

"Hey Ryan" she responded letting out a little giggle.

"Would you want to be official...you know like...be my girlfriend?". My heart pounded out of my chest as I felt sweat droplets form on my forehead.

Her face became flushed with red again as I saw the playful look on her face turn to glee. You know that scene from Zootopia where the fox, Nick, tells a joke to the sloth at the DMV and his face slowly changes to a bright smile? That's exactly what Alyssa did.

"Nothing would make me happier Ryan" she answered kissing my chest, and wrapping her arms around me, as we slowly drifted into a cozy, tranquil nap.

The knots grip tightly against my limbs, not in a painful way but just enough to be restrictive and make things a little more...interesting.

It's quite a position for someone who considers themselves pretty masculine: tied up, naked, and alone on Alyssa's bed.

You may ask, Ryan, how did you get yourself in this situation?

Well the short answer is that my girlfriend wanted to try something new tonight, but you're not here for the short answer, are you?

It all started off as a typical night for Alyssa and I. Cuddled up on the couch, tipsy off a few glasses of wine, watching a movie. Tonight was Alyssa's turn to pick the movie, now normally, she'd throw on one of her favorite Disney movies, something like Frozen or Moana, but this time she had other ideas.

The movie she picked: 50 Shades of Grey! Now, I remember when this movie first came out when I was a teenager. Most of my friends were saying they were going to see it "as a joke" but I always had my doubts...

I'd never seen the movie before actually and neither had Alyssa. Little did we know the movie would reveal a fantasy she was hiding but had always been too shy to try with any previous partner.

"Oh wow...it's so hot how he controls her" Alyssa commented, fixated on the screen.

"I love how crazy he drives Anastasia, keeping her on the edge, begging to let her cum." she continued.

"Yeah...I won't lie that's pretty fucking hot" I agreed, my boner throbbing against the fabric of my shorts.

Alyssa noticed my raging member and laid her hand on my bulge and began to rub. In turn I did the same between her thighs, our eyes stayed glued to the screen.

My palm was immediately overcome with a sense of dampness through her grey sweatpants. Feeling a bit surprised I peered over to her and ho-ly shit! Sure enough there was a large wet spot on her crotch, and it was only getting larger! My god, how long had that been building?!

"God damn Alyssa! You're like soaking through your these!" I said looking over at her, shiny red hair in a pony tail, nipples poking through her blue sports bra, shallow breaths with eyes fluttering as I rubbed her visible arousal against my palm.

"I know you get really wet, but this is crazy!" I added with excitement.

"Ryannn...don't say that! It makes me self conscious!!" She replied, blush appearing over her face.

I reached into her waistband, and sure enough, immediately my hand engulfed in her desire whenI began to rub her, Alyssa biting her lip and closing her eyes.

"If watching this turns you on this much, imagine doing it for real." I said, looking over at her with a greedy smirk.

"I've f-fantasized about it," she responded through her moans.

"Yeah? You want me to tie you up and tease you like, Anastasia?" I asked, my middle finger entering her to which Alyssa let out a beautiful gasp.

"Other way around..." she said in a whimpery breath.

I was taken back for a second. Throughout our relationship I had always been the dominant one and I figured that Alyssa felt more comfortable being submissive. The idea made my stomach jump, not out of repulsion, but out of curiosity...and excitement. I decided to press her more on it.

"Oh yeah baby? How long have you been thinking about it?"

"I've always wanted to try it. You know, the idea of a petite, shy girl like me, tying you up, controlling your pleasure--begging me to let you cum. It just...it makes me so fucking hot!" She replied.

"I've never been the submissive one before...but I'd be down to try it..." I replied anxiously but also with intrigue....

Slam!

We'll have to cut this retelling short, Alyssa is back! And oh my god I nearly choked on my drool when I saw her.

This isn't the shy, cutesy girl from the office I fell in love with, this is a completely different form. She now wore a red body harness that left practically nothing to the imagination. The red strings of leather forming a star shape above her naked breasts, running down her body to form another stylish pattern right on her abs, her pussy covered by a single strand saturated from her building arousal to go along with a pair of black stripper heels.

"Holy fucckk." I let out under my breath, as the clicking of her heels on the ground grow louder and louder as she steps towards me.

"You like what you see?" She asks, standing in front of me and squeezing her bare tits together letting out a soft, seductive moan.

The piercings on her nipples had been changed out, no longer her signature silver barbells. Now she wore nipple shields that formed a shiny gold circle around her erect nipples with a little diamond pattern around the circumference.

"Do you like my new piercings? Oh why am I even asking, I know you do!" She responds by pulling her nipples tightly letting out a moany squeal.

My cock throbbed so hard that it hurt. I never knew Alyssa would have anything like this in her wardrobe!

"Alyssa...holy shit...you look...absolutely stunning!" I manage to get out under my breath while my body squirms with anticipation.

"That's you babe! Fuck you look so hot tied up like that," she replies, taking my hand and bringing it between her thighs.

"This is all your fault, just look at how wet you made me!" She teases, groaning and lifting her head back as she rubs my hand against her sopping pussy as if it were a sex toy, coating it in her horny anticipation.

She pushes my hand back, her love juices dripping between my fingers as she makes her way over to my cock, placing a single finger on the tip.

"By the time I'm done with you, this cock is going to be begging me for release," she states, running that single finger in circles around the sensitive tip.

"Oh my...looks like you've already sprung a leak...why don't I be a good girlfriend and get that for you..."

Alyssa brings her mouth to my hard cock, hovering less than an inch above it as she stuck out her tongue and begins to lap up the beads of precum. My body reacts involuntarily, fighting against the resistance of the rope.

"Jesus Ryan...it's so sexy when you struggle for me" she says, planting little kisses down my shaft, each one making it contract.

"Uh oh. Don't get too excited now, the fun has just begun" she explains, climbing on top of me, my stomach engulfed in the sticky strings her pussy had produced. Alyssa leans over, placing her hard nipple to my mouth.

"Go on, suck on my nipples while I grind on your cock," she ordered. I happily indulged, sucking on her nipple like it was a straw getting the last bit of a cocktail from a glass. She starts grinding on me, holding my arms down, the sound of her eager pussy causing my breaths to become shallow and choppy.

"Ooohhh yeeeahhh! That's it baby, make sure you nibble on them too...mmmmm yeeesss, like that!" She expresses as my tongue went wild on her hard nipples, Alyssa shifting her other tit into my mouth while she grinds on the guppy pond staining my abs.

I was skeptical of this whole scenario at first but seeing how worked up she was getting made it 100% worth it.

"Alyssa...please..." I beg, muffled through her nipples, the vibration of my voice on them causing her body to shudder.

"Oh my god! Love hearing you beg...." she purrs, lifting herself up, strings of her grool connecting her mound to my stomach.

"Fuck, looks like I'm leaking too...I think I need you to clean it up for me" she continues as she scooched her way up to my face, her wetness dripping onto me as she hovered. Finally after a painfully long amount of time she finally sat down, my mouth engulfed in her delicious folds.

"Yes! Yes! Yes!" She moans, reaching her hands onto my shoulders and straddling against my mouth. I practically drowne in her arousal, if these were my last moments, I'll died a happy man!

"That's it baby...f-fuck your being such a good boy, eat that pussy darling!"

She begins to put her full weight on me, her taste was all over my face at this point, and only building from here.

"That's it! That's it! Work that mouth for me honey!" She moans, running her hand through my hair as her legs bucked.

"You gonna be a good boy and make me cum? Jesus my cooch is gonna fucking drown you!"

My tongue ran wild, flicking her clit with perfect timing each time.

"Yeeeaaahhh...ahhhahhaha you're gonna make me squirt baby. You want me to squirt all over your face darling?"

"Emmhuumm" I utter through her glistening lips.

"Good honey...here it comes...here it comes...haaaaaaahhhh!!" She screamed as her cum rained down on me, running off my face in all directions as her body quivered above me. She breathes heavily as the flow from her pussy slows, lifting herself up, leaving behind more of her delicious strings.

"Good. Boy." She whispered, eyes full of adrenaline as she made her way back down to my cock.

"Well what do we have here...Ryan..." she said crossing her arms as if she was a disappointed parent, "you have precum leaking down your shaft...dirty boy...your tip is absolutely covered!" She said running an open palm up and down my shaft. The slickness of my precum making the friction twice as good, if she kept that up I was gonna explode with cum...and then she stopped.

"Oh not yet darling...I want you desperate for it!" She said pressing my cock onto me and resting her slit on top of it. Once again Alyssa began to grind, the wet sounds of the friction driving me crazy. Her groans began to pick up as she placed her hands on my chest to balance herself.

"Al-Alyssa...Oohh that's sooo good" I replied, more than anything just wanting to grab her waist and increase her speed. She grinded on my painfully slow, coating my cock, before alternating between fast and slow, teasing me. "That's it baby, fight it...don't you dare cum yet" she demanded as she placed one hand on her breast, yanking her piercing and yelping.

"Alyssa...please...I need--"

Instantly she hops off, giving me a devilish smile and wagging her finger. In this moment, I found it strangely wholesome. Alyssa wasn't just horny, and incredibly sexy, she was also having the time of her life and couldn't hide her happiness beneath her new dom exterior!

It must be a freeing feeling, not only to break free from her quiet, nervous day to day experience, but also for such a small, petite woman to be the one in control in the bedroom for once.

She jumps down to my crotch, face to face with my desperately pulsing cock, begging her to take me over the edge. Her tongue runs up the back of my shaft, making my body jerk against the ropes. She looked at me dead in the eye, as she licked the tip of my cock like a lollipop that she had all day to enjoy, my impatience and desperation growing.

"Tell me Ryan..how badly do you wanna cum?" Alyssa asks me, running little teasing kisses all across my cock.

"Really fucking bad..." I replied.

"Ohh?" She replied, starting to stroke me hard in her hand, building me up more and more until I was right on the edge.

"That's it Alyssa! Don't stop, please!"

That's when she pulled away, with those adorable mocking eyes. "Patience Ryan...your time will come soon...no pun intended" she said as she began to lick around my shaft lightly with her tongue. "Who controls your pleasure?"

"You do Alyssa! Please...I need to cum!" I reply, helplessly in a tone I hardly recognized.

"Excellent, cause you know...only good boys get to cum" she said, increasing her stroking speed, myself being just seconds away from shooting ropes of relief.

Once again, when I'm desperate and right on the edge, she pulls her hand away. She continued to do this for what seemed like an hour, building me up, edging me, smiling back at me and licking her lips with gorgeous evil in her eyes.

She kept asking me if I'm her good boy, who owned my orgasm. No matter how much I confirmed and begged, she refused to let me over the edge.

As I drip pre-cum, internally screaming for her permission to cum, Alyssa stood up and walked over to her desk drawer, pulling out a pink vibrator and a little rope before walking back over to the bed.

"Alyssa...what are you--"

"Shhh" she whispers with her finger over her mouth.

"You've been such a good boy, being patient, making me hornier and hornier... I'm gonna let you cum now, but on my terms!"

She gets back on the bed facing me, pushing her ass out until her pussy was in direct contact with my shaft, rubbing up and down, mixing our combined, sticky arousal. She grabs the vibrator and rope and begins to tie it around my quivering cock. It was light, but firm enough to hold it in place.

"I'm gonna turn it on now, Ryan...and we're gonna cum together!"

She turns the vibrator on, sending waves of pleasure running through my shaft. It was a unique sensation, but certainly not unpleasant! She then takes my shaft with the vibrator attached in her hand and places it against her pussy. Our groans of agony fill the room along with the sounds of the buzzing.

ALyssa just holds it there for a few moments while we stare into each others dark, lustful eyes, our orgasms building, arousals dripping off the vibrator onto the sheets below.

I can't help but find it so hot that not only was she controlling my orgasm, but was also using my cock as an extension of her sex toy.

"Ahhhhhh are you close baby?" She moaned out, hinting her next orgasm was imminent.

"So fucking close! Please, just don't stop it!" I begged her.

"Good baby me too, let's cum together on my count baby in 10...9..."

Damn it she was using my count down trade against me!

"8...7...6..."

She was counting so slowly, as if she was trying to fit a ten minutes into these 10 seconds.

"5...4...3..."

Our legs were now shaking violently in unison, our bodies beyond needy for that sweet climax.

"2...1..."

The mix our horny juices were now splashing off the vibrator, both our bodies shuddering like we were stuck in a winter storm, as I wait for Alyssa's final count. Our chests rise and fall rapidly and our heavy breaths are totally in sync just waiting for the grand finale!

"0...CU-uuuh-uhhh-mmm!"

My being jerks and spasms in the craziest movements I'd ever felt, the ropes of cum shooting out of me heavier and farther than ever before, landing on Alyssa's stomach, her face, her hair, and splatter down onto the bedsheets below us. Her orgasm coats my cock, as our legs shake uncontrollably and we unite in a feral shout!

The look of her scrunched face while she bites her lip caused the pulse in my cock to take over as it jerks back and forth on its own,relentlessly cumming again and again.

Alyssa's pussy in turn floods my crotch, contracting hard as she squeezes her small breasts together tightly in her free hand.

Even when she turns the vibrator off our orgasms still continue running through us, our bodies moving haphazardly in salute to the ultimate edging climax!

Once her body finally recovers the minimum strength needed, she shut off the vibrator and jumps up, beginning to release the ropes, her body still shaky, as she fiddles with the knots

Finally she collapses onto me, not caring at all of the mixture of our releases that soaked the front of her body.

"Well...how was that?" She asks, her body to still periodically have her climax after shocks run through it.

"Amazing...I've never cum that hard before!" I replied.

"Same...seeing you desperate like that just woke something up in me"...

"I know Alyssa that was--"

"Shhh" she whisper, putting a finger over my mouth.

"Just enjoy the afterglow, honey. I love you Ryan..."

My eyes bolden and my heart warms hearing her say those words for the first time. I could feel the blush taking over my face as I repeat it back to her.

"I love you too, Alyssa."