Megan is a waitress at On the Border, she is 5' tall with slender petite figure and small 30B breasts. I was finishing an early dinner, " More coffee, sir?" I looked up at the girl standing next to me, jug in hand, lips slightly parted. I nodded slowly. " Please." I watched as she leaned forward, the neckline of her blouse falling forward to reveal a glimpse of white cotton bra. My eyes raked up towards her face, the full lips, the brown curls that fell around her face. God, she was cute. I had already noted the name scrawled across the badge on her chest. Megan: happy to help.
" Megan, isn't it?" She looked up at me, surprised. " I know you probably get this all the time, but I was wondering if I could take you out sometime?" She blushed furiously.
" I... we... we're not really supposed to. Sorry." She straightened up, smoothing down her pants with her free hand. I smiled. " No, that's cool. Understandable." She almost returned my smile, I noticed -- her lips quirked a little at any rate. I watched her walk away towards the kitchen and took a sip of my coffee. That small ass... I imagined sliding her pants and panties off then sliding a hand over her sweet little ass. Jesus. The things I could do to her.
I drank my coffee slowly, and signalled to another waitress to bring me the bill. I watched Megan run it through the computer, watched her bend and scrawl something across the receipt. She walked across to my table and presented the bill with a barely perceptible nod. I unfolded the paper, noted the figure, and then something else at the bottom -- in what had to be Megan's handwriting, the words " I finish at 6. Pick me up?"
I counted out coins to cover my dinner. I dropped them neatly into the little silver tray, and carefully folded the bill into my pocket. As I left he nodded over to the waitresses behind the counter. " Thanks, ladies. See you later."
Six o'clock and I was sitting in my car in the restaurant parking lot, waiting for Megan to emerge. It has been way to long since I have been with a young attractive woman. The restaurant door swung open and she appeared, a hooded jacket pulled over her uniform, looking around anxiously. I stepped out of the car to signal to her. She ran across and came to a stop just in front of me, slightly out of breath. " Hi." I looked down at her. she was almost shaking. I had not realised before how little she was? I was a big guy, and she was tiny. I towered over her. " Megan. Hi." She smiled. " I don't even know your name."
" Does it matter?" She laughed. " Well, no. I suppose not."
" Have a seat?" I gestured to the passenger side of the car. She nodded and went to get in as he slid back into the driver's seat. " How was the rest of your shift?" " Okay. I suppose. I'd rather not talk about work." " What would you rather talk about?" She glanced shyly at me. " I don't know. You. How old are you?" " Forty-Nine. How old are you?" " Eighteen. Last week." " Do you have a boyfriend?" " No."
"Good." She laughed at that, I leaned across her and in one swift movement pressed my mouth onto hers. She didn't respond at first, after a couple of seconds her mouth moved in motion with mine, and her lips parted to allow my tongue to dip inside. I moved my hand onto her soft thigh, gently squeezing the flesh beneath my fingers. When I pulled away she was blushing again, her eyes locked onto mine. " Would you like to come to my place, Megan?" She hesitated for a moment, and then nodded. " Yes."
I drove to the apartment in Turtle Creek, pulling in front of the building the valet took the car to park, leading Megan up the path to the front door and into the elevator. Entering the penthouse, I watched her slip off her shoes, and I took her jacket from her to hang up.
" The living room's just through there. You go and make yourself comfortable and I'll get us a drink." I paused in the kitchen, I uncorked the bottle of wine and poured out into two wine glasses. When I carried them into the living room she was perched on the sofa, hands clasped in her lap. " Is wine ok?" She nodded, taking a glass from me. " Fine. Thank you." She took a big gulp from the glass as I settled next to her on the sofa, and they sat in silence for a few moments. " It's very nice. Thanks."
" That's ok. Come here." I took the glass from her and placed both glasses unceremoniously on the coffe table Megan inched closer to me. I placed my hand on the side of her face to pull her towards me for a kiss. Her shy little tongue danced with mine, my hand moving to tangle in her hair. My other hand moved to her pants waistband
pulling it down. She pulled away, looking anxious. " What's wrong?" " I... I've never done this before." " Never done what? Do you mean you're a virgin?" She nodded. "And how far have you gone? Have you kissed boys before?" Again, a nod. " Yes. I've kissed. But never... never anything else."
She seemed to be enjoying the kisses, at any rate. Her plump little mouth pressed against me as her arms wrapped around my neck. I couldn't resist, and pulled her sideways so that our bodies were pressed against each other. She pushed me aganist me " No...please." She gasped. My cock throbbing in my pants. " Megan. I want to take you upstairs." She looked nervous again. " I don't... I don't know what to do." " Don't worry. I'll show you." " Well... ok. Yes. Ok." " Sure?" " Yes."
I took her hand and led her up the stairs, into my bedroom, where she lay expectantly on the bed. " Have you ever seen a hard cock, Megan?" " No. Well... no." My hands moved to my jeans, slowly unfastening the buttons there. " I'm going to show you mine. I want you to put it in your mouth." I slid my jeans and shorts down my thighs, a flicker of worry crossed her face, quickly followed by what could only be curiosity. " Come here." She crawled towards me, I place her hand around the base of my cock.
" What do I do?" " Just... open your mouth. Lick it. Suck it. Swallow it." " I can't." She replied. I begin pressing my tongue into her mouth. A shockwave went through her, and she was instantly turned on. She begins kissing me passionately, and we made out for several minutes. " I know you want me, John." Megan replied. " Do you want me?" I asked.
She nodded her head and begins kissing me again. Megan lays on her back on the bed. I reached under her shirt and unhooked her bra. I ripped them both off of her and begin massaging her breasts. I leaned down taking her erect nipple in my mouth, and I sucked on it.
" Mmmmmm, that feels so good" She moaned. I ran my hands up and down her sides as I sucked her breast and teased her nipple with my tongue. She could feel my hard cock beneath my pants, so she begins unfastening my belt and taking my pants off.
" I am so hard for you, Megan. But are you sure you want to do th--?" Before I could finish my sentence, she was struggling to get my briefs off over my massive erection. Once they were off, I laid on my back and Megan got on her knees next to me. Leaning down she
slowly begins licking my penis from it's head all the way down it's shaft. " Ohhhhhhh," I groaned. " Megan..." She took my cock in her mouth and begins to suck up and down ever so slowly, massaging my throbbing balls as she did. ' You look so sexy sucking my cock," I said as I laid my head back in ecstasy.
She begins sucking harder and faster, eventually taking all nine inches of my cock back in her throat. I grabbed her hair and pushed her face further down on my cock and she begins to gag. " Deep throat it, Megan." I moaned. She sucked my cock for five minutes.
" Lay down, I want to taste that sweet pussy now" I commanded. At that, I flipped her over and begin flicking my tongue against her clit. She gasped in excitement, and begins to move her hips to the rhythm of me sucking her throbbing clit. " You like that, John?" She asked. " You like tasting young sweet virgin pussy?"
I begin to suck even harder, breaking to lick her pussy from top to bottom before returning to sucking. " Mmmmmmm," She moaned. " I need you now. I want you to fuck me taking my virginity." I positioned myself on top of her and begin kissing her passionately. I reached down and placed my rock hard thick cock at the tip of her pussy. " Fuck me, John." She pleaded. I pushed into her, I could feel her pussy was lubricated. I could feel a part of her liked it. I thursted hard into her driving the head of my cock into her, “ OMG STOP! STOP! OH PLEASE STOP!” Megan screamed. " Oh! Baby, your so tight. My God, ssssoooo tight!' I pull completely out of her.
Then with the head barely touching her lips again, I drive my hips forward using all of my weight. For a brief, her lips resisted, and then split to allow the hard thick instrument enter her, slamming through her tight vaginal canal and driving itself at least 6 inches in on the first thrust. Young virgins are not meant to be deflowered or stretched like this, so I wasn’t surprised at all when her whole body jerked in response to the white hot pain of the instrument slicing into her small tight young pussy as she emitted a screech " OMG! OMG! AAAAAHHH! ". She screeched " AAAAHHH! TAKE IT OUT! AAAAAHHHH! " Pulling back several inches, I saw lots of blood covering my cock, and dribbling down on to the bed. Then I drive forward again, slamming the head right up against her cervix. I draw back and start ramming the tight young woman as she howled pitifully " OMG! AAAAAHHHH! AAAAAYYYY! AAAAHHHH! ". The feel of her unprepared and tight small virgin pussy milking my cock sent shivers of excitement through my body.
" You are to big John, oh my God! You are hurting me...Take it out...Please Stop John." She screamed. I begin slowly thrusting, giving her my full length hard and deep. " You are sooo tight Megan. Your pussy feels so good." I said as I thrusted in and out. I begin to fuck her faster, harder and deep. " Ohhh John, your cock is stretching and tearing my small pussy" She moaned. " Mmmmm, it's so good." I held myself up with my hands and begin slamming into her like a pile driver. The pain took her by surprise but in a moment she feels my large hairy balls resting against her pussy flesh and she knew she had taken all of me. The feeling of fullness was incredible! In a way she was proud of herself. She had taken all 9" of me. I began to pull out but quickly thrust deep back in . I was building a rhythm gradually taking longer and longer deeper strokes until I had sheathing and unsheathing of my full 9" on each stroke.
Her pussy resisting each thrust, clamping down in a vain attempt at stopping each subsequent penile impalement. Tears were pouring from her face as her tight canal was stretched, scrapped and torn by the sustained ramming I was inflicting on her. Gradually, the continued ramming of my cockhead gave to the back of her pussy caused it to give a bit. It feels great, having her tight young pussy grasping the entire shaft including the base of my cock, convulsing from the trauma, continuely spasming as her whole body heaves
and bucks. I groaned into her mouth as I continued slamming into her like a pile driver. Tears streamed down Megan's. " I'm going to cum Megan. Where do you want me to spill my seed." "Cum inside me, John." She gasped. " I want you to fill my pussy with your hot cum!" " I'm going to fill you with my seed." I pounded into the wailing young woman without mercy. She could feel me begin to swell, I drove all the way in, holding it there as the volcanic explosion pumped my warm semen into her. I held my cock there for a few minutes, feeling her pussy struggling to expel me. After a few minutes, I pulled my cock out and looked at the blood on it, and the blood and sperm dripping out of her split open pussy, as it still twitched from the trauma it had just endured.
She sobbed heavily for a few more minutes, I rolled Megan on to her stomach. I grabbed her waist pulling her up onto her knees, her tight virgin ass in the air begging to be fucked. The feel of fucking a young woman's small tight virgin ass is undescribably.
I slid my hands up her slender legs and rested them on her ass. " You have such a beautiful ass and I bet it is hot, and sooo tight. I parted her legs, tears continue to run down Megan's face. Her legs were now spread obscenely wide, opening her pussy and her ass to me. "That's too far, it hurts", she cried. I looked at this beauty spread naked before me, her ass open, her anus peaking out. I eased between Megan's thighs. " What are you doing" she yelled. " Quiet down and do as you are asked. My hands began fondling her ass. Slipping my hands between her cheeks moving toward her anus." Please not there, that will hurt." My finger reached her anus and Megan cringes in fear as it begins to enter her." Relax your ass and let me have my way."
My finger was dry and it hurt as it entered her. I pushed deeper into her rectum," OOOWWW, that hurts, you're pushing too hard." I pushed hard and my finger plunged deep into her rectum until my knuckles hit her ass." Tighten your ass on my finger. Megan grasped my finger, " Again, you are very tight." Megan grasped my finger again. My finger pulled from her anus with a pop. " Ohhh. Ohhh. Uuhhh. Uuhhh. Ohhh! OHHH! UUHHH! UUHHH! MMMMMMM!" Megan screamed. " OHHH! OHHH! UUHHH! UUHHH!" Megan moaned as I pushed tighter against her. " OMG! OMG! OHHH! OHHH!! UUHHH! OHHH! UH-UH-UH-UUUHHHHHOOOOOOOOO" Megan screamed as I pushed hard into her, the bulbous plum head of my hard popping into her small tight virgin ass. " OHHH! OHHH!! UUHHH! OHHH! UH-UH-UH-UUUHHHHHOOOOOOOOO!!!!" Megan groaned as her body was wracked by pain as my hard thick cock slides in 2 inches.
I stroked her sides squeezing her breasts, "OOOWW, that hurts." That's nothing, wait untill my cock forces its way into your asshole." Megan feels me push up from her body and fist my cock placing it on her anus. " Your lesson is about to begin" and I begin to push the bulbous plum head of my cock into her anus. My cock was well lubricated with blood and semen as I pushed into her anus. It felt like a baseball bat was driving up her ass as I continued to push and pull back and push again, each time gaining a millimeter at a time."OOOOOWWW, it's too big and thick, don't stick it into my ass," she wailed.
I pushed harder and a's anus gave up to the assualt and opened to the head of cock. "AAAAAAAAAHHH, OWWWWWW, its tearing me, take it out, don't push it in," she yelled. You only got the head, wait until you get all 9 inches fucked up your ass. I am going to stretch you open, You better fuck back. I pushed another inch in, than out. The next thrust gained two inches, than back out. Megan's asshole was bleeding from the assualt, adding more lubrication to my cock for me to continue. " Here comes all of it baby" and I pushed with all my might into her asshole. 9 inches of hard cock forced her asshole to open bigger then it ever. Her asshole was stretched and torn to accept the fucking of her ass. I pulled my cock out to the head and than begin the painful journey back up her ass. My cock was gripped tightly by her ass.I begin to fuck her ass hard and fast, riding her. My cock thrusted into her deeper each time, causing her to cramp as it was forced to accept my hard wide cock.
Each stroke of my cock brought a fresh batch of pain to her ass. Megan feels my cock swell as I thrusted into her, I groaned as I exploded in her. My hot cum flowing like lava in her. I collapsed on top of her breathing hard in her ear. Megan was shivering and crying. " Oh God!!" I moaned as I begin shooting my load into her. Megan was still in the throes of her own orgasm of pain and pleasure, as she feels the heat of my sperm filling her. The throbbing of my cock inside her causes her to groan " OHHH! OHHH! UUHHH! UUHHH!" as her orgasms begins abating. Both of us collapsed on the bed breathing heavly and sweaty.
I raise up pulling my cock out of her, Megan laying there gasping for breath. Her thighs covered in blood and semen. I roll to her side caressing her back, " Megan, you are now a woman. That was great sex." I got up to go take a shower.