Bye Bye Cherry
Katie decides to seduce her boss to lose her cherry
I was still a virgin the summer of 1987, I had just graduated from high school and my 18 th birthday had come and gone. I didn’t want to lose my virginity in the back seat of a Buick to some overzealous jock with no dick control. No, I had big plans for popping my cherry. I had a job at a local fast food joint but had turned in my two week notice as I was leaving for college a couple days after my last day.
My boss, Charlie, was 25 and hot as hell! He was just over six feet tall, had a smokin’ hot body, black hair, and blue eyes. We had been flirting for months but I was always considered to be hands-off: first because I wasn’t 18 yet and second because he was my boss. So the sexual tension grew and festered until I could barely stand to be in the same room with him without jumping his bones!
I had been plotting my seduction of Charlie for weeks by the time my last day came around. I’m not sure which excited me more: leaving for college or finally losing my cherry to Charlie! I spent many nights masturbating to my fantasies. My last night on the job, Charlie and I would be closing together; and alone. That would be my chance to surprise him.
In preparation for the night, I bought the cutest tight pair of pink cotton panties and matching lace bra. I would have preferred something bold and lacy but this was a small town; we had only a few stores that sold lingerie and none of them were Victoria’s Secrets and they were all run by nosy old ladies. So I opted to play up my innocence. I wore my hair pulled back into a high ponytail and my make-up was flawless. Unfortunately I was stuck wearing my ugly uniform but I was able to keep it buttoned low and added a sexy perfume that Charlie had already said he really liked.
The night seemed to drag on. We closed at 10:00 and usually finished with the closing process around 11:00, provided that nothing major broke down. When I had finished cleaning the restrooms and the dining room I stepped into the restrooms to freshen up. I washed away any scent of cleaning products, touched up my make-up, brushed my teeth, and reapplied the sexy scent. Feeling really bold, I stripped down to my underwear and neatly folded and stacked my uniform. I checked out my body in the ladies’ room mirror. I was barely five-six, fit from softball, with light brown hair and eyes the color of dark amber. My breasts were a 32 C, my ass firm and round. Then I walked down the hall to Charlie’s office, where he was running his daily reports.
Charlie’s back was to me and he was entering numbers on his 10-key. “Hey, did you want my uniform tonight or did you want me to bring it back later?”
“Whatever works for you.” Then he turned around in his seat and saw that I was only wearing my pink panties and bra. “Oh.”
I grinned wickedly and said, “I think you should take it now.”
Charlie cleared this throat, “If I do what are you going to wear home?” His eyes greedily drank in my body.
“I have a little sundress in my bag. So do you want it or not?” Charlie looked at me with questioning eyes; I don’t think he was sure which I was talking about: the uniform or my body. I took mercy on him, walked to his desk and sat the uniform on the shelf over his head. Reaching up caused my C cup breasts to brush lightly against his face. I heard him groan. I felt his hands grasp my hips.
My entire body tingled with anticipation. I wasn’t nervous or scared; I was just really excited. I had waited so long for this; had planned it so beautifully; and now, it was finally going to happen!
Charlie lowered me onto his lap but instead of kissing me he leaned his forehead against mine and sighed, “Why are you doing this to me?”
I was devastated, I thought he wanted me too; hell, the bulge in his crotch told me that. So why wasn’t he going for it? “Don’t you want me, Charlie?” I asked in my most innocent voice.
“Fuck, yes! Can’t you tell?” He glanced down at his bulging erection.
“Then what’s the problem?” I brushed my leg against his bulge.
“How old are you?” His voice was strained with the effort to restrain himself.
“Charlie, I turned 18 over a month ago. So you don’t need to worry about that. Also, tonight is my last night and I have clocked out, so you are no longer my boss. In a couple of days I will be off to college and you probably won’t see me again or at least for a long time. So no strings attached; no expectations of love; just two adults who want each other.” I figured with him already hesitant I shouldn’t mention that he would be popping my cherry.
I guess all of my arguments hit home because Charlie didn’t hesitate a second after that. With a groan laced with desire, he grabbed the back of my head and brought me in for a deep hungry kiss. His hot tongue stroked every bit of my eager mouth. I wrapped my arms around his neck and pressed myself against him. I tried to remember everything I had learned from the porn movies and magazines but it was so hard to concentrate when he moved his hand up to stroke my breasts. Charlie slipped his hand into the lacy fabric and teased my nipple to a hard little bud. I moaned in pleasure which only encouraged him to add more pressure to my sensitive nipple.
Charlie reached around me and unclasped my bra; he broke our kiss and began to trail kisses down my neck until he claimed one rosy nipple between his lips. While he sucked and nibbled on one, his hand tweaked and teased the other. I couldn’t sit still. The sensation was like nothing I had ever experienced while playing with myself. Boldly, I reached down and caressed his erection through his pants. Charlie growled his pleasure and sucked harder. My back arched with the need for more.
“Fuck, Katie, I have dreamed about touching you since the day you applied for the job! Your sweet round ass just begged to be spanked!” Charlie rubbed my wet panties, pressing his thumb against my throbbing clit. I could feel my orgasm building, the fire burning deep in my belly and shooting outwards.
“Oh, Charlie, baby, you’re going to make me cum!” I grabbed his head and kissed him as he rubbed my clit harder until I was gasping and moaning into his hot mouth. When the orgasm hit I bucked and threw my head back as hot wave after wave washed over my body. I couldn’t believe Charlie was finally touching me! Charlie lifted me up and sat me on his desk. I let my bra slide to the floor. Charlie began to undress in front of me, taking his time, drawing out my need to feel him in me.
When he dropped his boxers to reveal his beautiful thick seven inch cock I gasped. I wondered if that would fit in me. I worried that he would be able to tell I was a virgin and would stop. I heard Charlie laugh, “Don’t look so frightened, Katie, it’s not going to bite you.”
I giggled, “No but I might bite it,” I winked at him.
“Want to taste it?” He wiggled his cock, already wet with pre cum, at me suggestively. I nodded mutely, licking my lips hungrily. “Good, but you are going to have to wait your turn, Princess, because I have been dying to taste you,” Charlie growled as he stepped closer. He hooked his fingers into the waistband of my panties and began to pull them down; I raised my hips to help him. Charlie propped my feet up on the desk and sat in his chair in front of me. He lowered his seat until he was at just the right height then slowly began to lick his way down my inner thigh until he reached my freshly waxed pussy. He blew his hot breath across my wet lips causing me to shiver and moan. He kissed my outer lips and everywhere but where I so longed for him to. I was aching to feel his mouth on my pussy. When I thought I couldn’t stand his teasing another second, Charlie sucked my throbbing clit into his hot mouth. I screamed as electricity surged through my body. Charlie sucked my clit until I was writhing on his desk. Then he plunged his tongue into my sultry pussy, he stiffened his tongue and fucked me with it before softly licking my inner lips, then returning to my hard clit.
“Shit, that feels so fucking good, Baby! Please don’t stop!” I begged him. Charlie grabbed my hips and scooted me closer until his face was completely buried in my pussy. His tongue and lips worked me into a frenzy and before long I was coming again. “Oh God! I’m coming!” Charlie held me in place as I came all over his face. I had to beg him to stop when he kept flicking his stiff tongue across my sensitive clit. “Please, Charlie, stop, please,” I begged, trying to squirm away.
“A minute ago you were begging me not to stop,” he laughed, sitting up, “so which is it?” A smug smile lit his face.
I wasn’t about to be undone. I may be a virgin but I can give head like nobody else; just ask the class president and the football captain. I slid off the desk and onto my knees in front of him. My eyes locked with his as I grasped his throbbing cock in my hands and began to slide them up and down his shaft. I leaned over and began to lick his pulsing head then slid it into my mouth and gently sucked. I heard Charlie moan and that was all the encouragement I needed. I eased my lips down his shaft, encircling his head with my tongue, building up suction. Then I released his cock, my lips making a popping sound, and repeated this treatment until Charlie placed his hand firmly on my head and held my tight mouth on his throbbing cock. I don’t gag easily and this time was no exception. I took all seven inches of this thick manhood and held it in the back of my throat, sucking as hard as I could. Charlie began to piston his shaft in my mouth, moaning my name as his hips worked faster and faster. I looked up and held his eyes while he told he was going to cum. I held him in place just as he held me and took his steamy load into my mouth and swallowed every last drop. I love the taste of cum.
“Shit, Katie, where the hell did you learn to do that?” Charlie gasped, wiping his brow.
“Either the back seat of a Buick or from watching late night porn,” I said boldly. Charlie laughed.
“You are so fucking hot,” he caressed my face as I was still kneeling between his legs.
“So are you, Charlie, I have been planning this night for months,” I said, resting my cheek against his thigh.
He laughed, “Oh yeah? What else do you have planned?”
“That depends; can we go back to your place?” I knew Charlie lived alone, whereas I still lived at home with my folks and kid brothers.
“Give me ten minutes to put all this away,” he indicated the reports on his desk.
“Make it five and you’ve got a deal,” I jumped up and went to get my things. I threw my sundress over my head, it was short little number, cotton with spaghetti straps, white with tiny pink flowers. It was damn near see through in the sunlight. I gathered my panties and bra up, not bothering to put them on, and shoved them in my bag.
True to his word, Charlie met me at the back door in five minutes. He set the alarm and locked up as we walked to his car. It was a good thing that everything was going as planned because I hadn’t driven to work that night so I wouldn’t have had a ride home if it had all blown up in my face.
Charlie drove a monstrous truck that was jacked up so high that it was going to be impossible for me to climb in without flashing my pussy at anyone that happened to be walking by. Charlie, ever the gentleman, opened the door to his truck for me and offered me a hand up into the truck.
“Nice,” I heard him whisper as he caught site of my pussy, which was still wet from our earth shattering foreplay. I looked over my shoulder and gave him my wickedest smile, to which he reached up and smacked me on the ass.
I squealed and climbed in quickly and shut the door.
Charlie ran around to the driver’s side and climbed in next to me. He leaned over and slid me down on the seat, pinning me against his leather seats. He kissed me with barely restrained passion, his fingers reached under my short dress and caressed my pussy until I began to rub against his hand, moaning, and not wanting him to stop. Which he did, smiling as he sat up and started the truck. I could only continue to lay there with my legs spread, panting with unreleased fervor.
“You’re a fucking tease,” I said, finally able to speak.
“No more than you are, sweetheart.” I started to sit up but Charlie stayed me with a hand on my leg. “No, baby, stay like that; I want to look at that sweet pussy while I am driving.” Oh my God, that made me so hot so I spread my legs a little wider and began touching my moist glistening lips. Charlie groaned, “You keep that up and we are either going to crash or I am going to have to pull over and fuck you on the side of the road,” he warned.
Was there anything that man could say that wouldn’t make my pussy spasm? I moaned and slipped a finger between my folds. Charlie was trying desperately to divide his attention between the road and my cunt. I saw him lick his lips and heard him swear under his breath before his finger joined mine. Charlie helped me to finger fuck my box. I arched my hips to give his finger better access and moved my finger up to my clit rubbing it madly.
Charlie stopped at a red light and became focused to banging me with two fingers. A horn sounded behind him, startling both of us. We dissolved into giggles as he moved forward through the intersection. I didn’t sit up until he stopped in front of his apartment. Charlie lifted my out of his truck, took me by the hand and practically ran with me to his door.
He led me straight to the bathroom and started the shower. Before I realized what he was doing, Charlie lifted me up and set me under the stream of cold water. I squealed and tried to dodge the spray as my cotton dress clung to my hard nipples and curves. The water began to heat up but my nipples stayed hard. I watched as Charlie stripped naked, his wonderful cock already fully erect. He sat on the vanity and told me to start soaping up but to leave my dress on.
I grabbed a shower sponge and squirted it with musk scented shower gel. I knew this scent; Charlie smelled like it, the musky aroma always set my blood on fire. I inhaled the familiar scent and began to run the sponge over my body, across my belly, around my breasts, down my back, over my ass, and down my bare legs. There was something so erotic about washing myself while still dressed. I could feel my juices starting to flow. I looked up and saw Charlie stroking his cock as he watched me slowly lather up my body. Feeling sexier than I ever have, I lifted my dress and began soaping up my pussy, allowing my soapy fingers to slip between my folds. I moaned from my own touch.
“That’s it, baby, that’s so hot,” he stroked himself faster. I turned and leaned against the wall with my wet ass facing him, my dress sitting on my hips, and began to caress my cheeks with the sponge. I loved the feel of the soap dripping down my crack and onto my pussy. I played with my tight virgin asshole before slipping a soapy finger inside. It felt so good I came on the spot, crying out to Charlie.
He climbed into the shower with me and I turned the sponge on him, running it over every inch of his hard body, paying special attention to his throbbing cock, his full balls, and his firm ass. Charlie moaned with every touch; he encouraged everything I did. While I was squeezing the soap over his ass he leaned against the wall to give me access to his tight hole. I soaped it up then boldly stroked his bud with my tongue. Charlie swore but didn’t move away, I took that to mean he was cool with it and kept going. I licked his ass while massaging his balls. Charlie soaped up his cock and started stroking it again. I stopped licking and lubed up my finger again and gently eased into his hole.
“Fuck! Katie, fuck!” He stroked faster, I moved between his legs and took his balls into my mouth while sliding my finger in and out of his ass. “Shit, I am going to cum!” Charlie turned to face me and shot his load all over my breasts and face. I rubbed his cum across my nipples and licked my lips. Charlie pulled me up and kissed me hard; his cum smearing between our wet bodies.
We finished our shower, dried each other off and headed for the bedroom. Charlie lifted me up and I wrapped my legs around his waist, his already hard cock trapped between our bodies, pushing into my belly. He probed my mouth with his tongue; I ran my hands through his thick hair. Charlie walked us over to his bed where he unceremoniously dropped my on my ass before lowering himself over me.
“Are you ready, Katie?” He said looking deeply into my eyes.
“Yes,” I whispered breathlessly. My pussy was dripping wet and aching to feel him inside.
“Say it, I want to hear you say it, baby.”
“Fuck me, Charlie, please fuck my pussy!”
Charlie worked his fingers into my throbbing pussy working my juices around my lips, getting me ready for his entry. He rose above me, lifted my hips to meet him, and slowly eased his hard shaft into me. There was a moment of pain followed by total bliss. “Shit, Charlie, that feels so good!” I clawed at his ass cheeks, trying to pull him in deeper.
“Damn, you are so tight! You feel so fucking good, baby!” Charlie began to thrust harder and faster, I met his every thrust. I knew I was going to be sore after this so I wanted to get in as many positions as possible before we finished.
“Charlie, I want to ride you.” Charlie rolled over, never leaving my pussy and suddenly I was on top. I pictured how I had seen women do this in porn and slowly started to grind against him. My clit rubbed against his hard abs, his cock head rubbed against my g-spot; the combination sending me over the edge. “Shit, shit, shit! I’m coming!” I grabbed Charlie’s hands to steady myself as my juices gushed from me onto him. My body shook from the most powerful orgasm of my life. When I had recovered I began to bounce up and down on his cock.
“Yeah, baby, ride me hard, take that cock in your tight pussy!” Charlie grabbed my hips and helped me impale myself on his cock. Over and over I rose to the tip then slammed myself down to the base of his shaft. “Shit, Katie, you are amazing!” Charlie flipped me over again, this time losing his hold on my pussy. But he didn’t miss a beat. Raising me up onto my knees Charlie slid his pulsing cock into my sopping pussy. He grabbed my hips and slammed his shaft into me hard and fast. I could feel him in the pit of my belly; the feeling was both painful and delightful. He filled every inch of me with his tool. I cried out when he grabbed my shoulders and drove himself deeper into me. “I going to cum, baby, I am going to cum in that tight pussy!”
“Yes, fill me up with your juice! Fill your pussy!”
“It’s my pussy, all mine!” Charlie cried out and began to shoot his load deep into my pussy. This set off my own climax and I felt my juice oozing down my legs. Charlie and I collapsed together onto his bed, his softening penis slipping from my swollen pussy; our mixed juices oozed out of me, our breathing rapid.
Charlie pulled me against him, kissed the back of my hair, and reached up to cup one of my breasts. “Thank you, Katie,” he whispered in my ear.
“For what?” I asked sleepily.
“For giving me the gift of your virginity.” I sat up, somewhat horrified. How did he know? Was it that obvious? Was I that bad? Charlie chuckled, he must have read my mind. “No, Princess, it wasn’t obvious. I actually had no idea until I entered you. I felt you tear and how tight you were and I just knew.” He leaned over and kissed me softly on the lips. “I hope your first time was as good as you hoped it would be.”
Giggling, I kissed my lover back, “Charlie, I think you spoiled me for anyone else. You were amazing!”
Charlie fell asleep curled up next to me under his sheets. The throbbing between my legs told me I was now a woman. The man slumbering deeply next to me told me I was a pretty good lover. The sticky cum sealing my legs together told me I was on my way to becoming a wanton slut. I fell asleep with a wicked smile on my face.