Older Woman Adventure
Introduction:
Lust and horny
Tonight’s date is with Karen age 33 never married is currently looking for a boyfriend, has been without a boyfriend for three years. She has been dating off and on in the last six months. She was encouraged to ask me for a date by a mutual friend. The phone rang once, Karen picked up breathlessly, I always knew when to call…” Babe, I’ll be there in an hour…let’s go for a nice dinner…” Karen can’t wait – dinner meant good food and possible sex…her favorite combination. This is our first night out together. ” But listen, afterwards we will need to go to my place for the rest of the night. I have early meetings tomorrow.” Karen frowned – was I really going to give up a chance of fucking her just for an extra hour’s worth of sleep! She made up her mind that she would drive me insane from the second I saw her…if I decided after all of that to still go home early then she is determined to send me home with a hard dick in my pants and a night of wet dreams awaiting me.
She rushed to finish her makeup and hair. Just the thought of being with me tonight had made her wet…and she ran to get ready. ” I’ll show him!” She thought! She decided to forego the regular jeans and sweater outfit tonight. Karen pulled on her sheer thigh-high stockings with lace tops, slid on her snakeskin stilettos, and pulled on a short pleated cheerleader-ish skirt. She knew I loved all these items separately, imagine them together! Ha! She pulled off her panties, and checked herself in the mirror…if she bent forward slightly then I could see the lace tops of her stockings, if she sat down it is even worse…God forbid if somebody brushed past her in the tiny restaurant – her whole pussy and ass would be on display! She would have to be careful – they were for my eyes only. Karen wanted to look desirable to me, but without looking like a total slut to everybody else…so she pulled on a demure, flimsy, cream-colored cashmere polo neck…this will do fine…she looked sexy as hell but elegantly so!
Karen can’t wait to show me. When the doorman called to say I was here she grabbed her Burberry trench and wrapped it tightly around her…she wanted to know how long it would take for me to notice she is wearing stockings and a skirt. As she got into my BMW, I glanced at her quickly and smiled. ” Karen – I looked forward to being with you tonight!” I said giving her a kiss. ” Yes, I looked forward to being with you too,” She replied with a hug. I looked sophisticated in trousers, polo shirt and a sport coat, with my hair disheveled and my rectangular glasses on! ” Too rich to care” is the right way to describe the look! We were on our way. I didn’t notice immediately…she supposed the car was dark…but before we reached the end of her block I slide my hand under her coat to her knee and said with a slight smile ” oh…Karen, what’s this?” ” What, I can’t wear a skirt for our date?” She asked me playfully. ” Of course you can…don’t give me that innocent look!” I loved it when a woman is a naughty girl. It makes me horny an gives me an excuse for rough sex later. I kept running my hand along her legs until we parked. Taking off my seat belt I said ” what else…?” as I slide my hand in between her thighs. “..no panties…like THAT Karen huh?!” I said as I lightly grazed her lips and clit with my finger. She smiled coyly and said nothing, just stopped my hand from exploring further and opened her door. Sighing, I stepped out too, and we walked in.
We sat at the bar while we waited for a table – Oh No, bar stools! There is no way she can even perch on these without showing her wares! Karen tried as best she can, sipping her Bailey’s with one hand and keeping her coat around her with the other…I knew how self-conscious she felt and stood my large 6’4″ frame in front of her so she felt better and is partially hidden! It also gave her the opportunity to glance at my huge bulge…while her coat allowed me to stroke her inner thighs…finally we got to our table and she took off her coat! Everybody stared as she sat down – she had probably flashed a little of her stocking tops by mistake! She tried to be as nonchalant as she can. I managed to keep stroking her legs under the table, but neither of us can reach the parts we wanted to reach! I spied the couple at the corner table next to us leaving and quickly asked the waiter to move us! Wonderful! As soon as we slide over she feels my large hand spread her thighs and my index finger probing her pussy…I made it wet with her juices and then spread them up her slit, opening her up for me. ” I’m out to tease me back tonight!” She realized!
With a little smile, I shoved my finger deep into her tight hole, making her wince with pain. She can’t moan, She can’t complain, She can’t do anything but gaze at me beseechingly to stop torturing her. Karen tried to grind her pussy back and forth on my finger but it is too obvious! I grinned, knowing I had her where I wanted her, and pulled my finger out, ” Mmmm…” I said as I tasted her pussy on my finger. Karen wanted to throw everything off the table and spread herself for my pleasure. She feels her wetness seep though down her thighs and to her skirt. I sat back enjoying my Scotch, winking at her. We barely talked during dinner, both enjoying the food, and especially the tension between us. When we got our main courses I slide my hand back between my thighs, pushing 2 fingers into her pussy, I start moving them rapidly around, faster and faster, I knew this would make her come! But she can’t because the waiter is right in front of us, waiting to grind pepper onto our pasta!
Karen shot me a death-stare and removed my fingers. I looked at her and whispered ” what…?” as I put one of my fingers to my mouth and inhaled her scent before sucking on it. I grabbed the back of her head and offered her the other wet finger, I love seeing a woman taste herself on me. Karen licked it enough to satisfy me and then pulled out a pencil from her bag. The tabletop is covered with white paper laying over the linen…She started to write me a message: ” For dessert, I’d like to be bent over and fucked HARD…check one YES _ or NO _” Reading it, I smiled and grabbed the pencil from her: ” HELL Yes…but how hard?” ” Make it HURT, make me BEG you to stop” ” Even if you were to beg me to stop, I wouldn’t listen” This has her pussy dripping. We rush to finish our meal, pay the cheque, and walk as composed as we can to the car. Once I opened the door for her and she sat down, I threw my hand in between her legs and spread them wide over the dashboard. Karen stared at me in disbelief – what on Earth was he thinking of doing?! Without a glance at her, I buried my head between her thighs and start licking her pussy as I stood in the road! We are parked in the middle of a street – there are big apartments on either side of us! Oh God my tongue feels so good flicking around her clit and exploring her slit!
In a minute I pulled back and shut the door. Getting into the car, I unzipped my pants pulling out my hard cock from my briefs. ” I want you to suck me dry” I whispered hoarsely. She made me wait a minute by stroking my thick veined dick and then lowered her head to it. Karen only sucked the head, licked around it, I groaned and pushed myself up into her mouth, but she refused to deep throat me, she wanted my cum inside her. Thank God we were only a few blocks from her apartment. When we got upstairs I watched her undress, but instructed her to leave the skirt and stockings on for my amusement. Her breasts bare, her dark nipples hard, I undressed myself completely and stood in front of her. She led me to the bed, letting her eyes drop from my head and chest to my huge thick cock protruding out. A cock that big deserved a good suck and fuck. Karen lay down as I approached her on my knees, pulling her head up as I proceeded to feed her my big cock. Karen sucked at me hungrily, looking up into my eyes, and then lowered herself further to suck on my balls. They are so delicious she loves feeling them in her mouth while she uses her hand to play with my shaft. She feels me wanting to fuck her face faster. I popped out of her mouth and she squeezed me in between her tits…licking the precum of the head of my penis. I start titty-fucking her, she didn’t want my cum in her mouth, she wanted me to spray her pussy. She stopped sucking and licking me, I let go of her tits, pushing me off her. I lay next to her, and bite her ass cheeks hard. Spreading her legs, I put two fingers inside her, I watched as she moaned and begged for my cock.
” Baby, wait…” I said as I feel her clit circling it with my fingers. One wet finger found its way to her asshole…I pushed it in watching her squirm. When I put my finger into her ass it makes her pussy wetter – it makes her feel like my dirty slut – she starts to drip with pussy juice. Karen thrashing around the bed, trying to dislodge my finger so I can finally give her that hard cock gleaming with wetness from her mouth. ” Baby, I told you to WAIT!” I commanded. She isn’t behaving. I grabbed her arms with my one free hand and held them above her head, giving her a warning glance. Now she is in for it. I resumed my finger fucking to her ass and pussy and then finally gave up. I wanted her too. Lifting myself between her thighs I placed the large head of my dick to her tight pussy. I pushed slightly, putting the head inside. I push hard, with a gasp from her, pushing my length in. I ripped into her. It feels so good, but she wanted more pain. ” Baby, turn me over and fuck me from behind…” I obliged. Spanking her hard, I placed my cock at the entrance to her pussy pushing it half way it. Pulling it out I said ” Suck me again”…She obliged just enough to feel me completely hard before she turned away. I pushed halfway inside her again, and pulled her hips back onto my dick.
I wanted her to do some work! ” Let me see you move” I said with a slight spank and stood still on my knees as I watched her round ass move back and forth, pumping my cock into her wet tight pussy. Karen knew I wouldn’t be able to take this sight for too long – She is right. I suddenly push down on her back, forcing her upper body into the sheets, and lifting her ass higher. I mounted her, leaning over her slamming myself repeatedly into her, spanking her from time to time. I stopped, spanked, restarted, gaining speed. Karen is in heaven – feeling me behind her, taking advantage of her, fucking her pussy until it is sore…She came so hard from feeling my soft balls smack again and again over her clit…it is too much as she screams in pleasure! After her screaming from the clitoral stimulation subsided, I fucked her harder, she feels my cock plunge in and out of her, feeling it deep and hard, and wanted more, she is losing control, ” Baby FUCK ME, PLEEEASE FUCK ME, MAKE IT HURT, HURT ME BABY FUCK ME FUCK ME HURT ME!” Karen begged me. I wanted it too and slammed as hard as I can into her, filling her with my hot sticky cream. I pulled out and lay back, totally satisfied. Karen, on the other hand collapsed into the mattress and is fighting to regain regular breathing! then I got up went to the bathroom, leaving her naked on the sheets. Karen climbed under the duvet cupping her pussy with one hand. It is still wet, she is still horny. She stops at the bathroom hearing a moan, she thought.
She came back into the bedroom and laid face down on the bed. I came back seeing her pussy is dripping with wetness. My cock is still hard, so I moved to her rubbing my cock up and down her ass crack to her pussy, and back and forth again. When I reached her pussy again I plunged my cock deep. ” OH FUCK YES, FUCK ME, FUCK ME John, MAKE ME YOUR FUCK SLAVE.” she screams. I’m slamming my cock into her again, I hear the bed creaking and feel it rocking as I slam hard into her. I’m slamming into her so hard that the bed is moving it hit the wall. I lifted her hips off the bed moving over her and holding her tight as I slam her pussy again when she yells for me to fuck her harder. Sweat is pouring off my body onto hers, I watch the drops roll to the center of her back then down her ass crack. Minutes later she is screaming, she is cumming, and with the first squeeze of her pussy I lifted her hip again plunging in deep as I grunted that I was cumming too. Falling onto her back I can’t move. Twenty minutes later I slowly move off her, taking her hand I help her off the bed to the big shower in the bathroom. Taking the long shower hose I turned it on full blast and slowly move it over her body, stopping at her tit’s and then I moved it between her legs and let it pulse on her clitoris.
” Oh John that feels so good, put your cock inside me too.” she told me. ” Not yet Karen, soon I will take you again.” I said softly. I move it away after a while, and told her to sit on the seat in the shower handing her the hose and told her to do the same thing to me. When she got to my cock I wanted her to roll my balls in her hand while she uses the water on my cock. Fighting for over 10 minutes to stop from cumming I took the hose away and turned the water off grabbing her I pull her into the bedroom again pushing her back onto the bed and crawled between her thighs. Lifting her feet onto my shoulders I moved my cock to her pussy and thrust hard, she is so wet I slide fully inside her. ” SO FUCKING TIGHT KAREN, YOUR PUSSY’S SO FUCKING WONDERFUL, CAN’T GET ENOUGH OF IT.” I shouted, as I slammed my cock repeatedly in her. She reaches down slipping her fingers between my cock and her pussy. As I moved into or out of her fingers tighten on my cock. My mouth suckled her nipples, as I used my hips, twisting my cock deeper. ” OOOOOOOOOOOOOO FUCK!, FUCK ME JOHN!, FUCK ME HARDER!, TAKE ME! , MAKE ME CUM JOHN!, OH MY FUCKING GOD JOHN I AM GOING TO CUM!!!, JOHN, I’M CUMMMMMINGGGGGGG!!!!” she screams, panting hard.
I feel the hot liquid bathing my cock, holding her hips tightly I thrust one last time as my body starts shaking and I feel my cum leaving my balls and traveling up my rock hard cock, and shooting deep inside her tight pussy. Slowly I move her legs to lay at my side, flipping them both over. Her on top of me, still holding her hips I slowly move her back and forth, my cock sliding back and forth until we slowly fell asleep. Waking up with a painful aching from my hard cock. With my right hand, as roughly as I can manage, I pull her ass crack open. Before she realized what is happening, I spread the vaseline across her puckered brown hole, coated both fingers, and jammed them inside up to the second knuckle. ” Aaaunggh!” This time the gasp of pain and groan of pleasure are all rolled into one. I shove my cock as far in as I can and start twisting my fingers around inside her asshole. My cock feels my fingers moving around in her ass as she whimpers repeatedly into the mattress.
As I feel her ass start to relax around my fingers, I slowly start spreading them apart as I resume pumping in and out of her pussy. I pull my fingers back a bit, increasing the spread of her butt hole. She is moaning like a foghorn now — I can’t tell if it is from pleasure or pain, and I don’t know if she can tell the difference either. Now it is time for phase 2. Without interrupting my stroke, I pull my fingers out of her ass. I hear her sigh with relief as I once again pick up the vaseline dipping my fingers in, taking a bigger glop than before. Timing myself carefully, in one smooth motion I pull my cock all the way out of her hot cunt, smearing the vaseline all over it, and shoving the first inch or so straight into her virgin butt. ” AaaaAAAAAAahhhh,” she screams, “Oh my god …oh my god…oh my god. It hurts…It hurts…Holy fuck it hurts…Ahhhh…Ahhhh.” I practically came right then, what with the feeling of her sphincter squeezing the hell out of my dick and her screaming and moaning from the pain. Looking down at her face half-pushed into the bed, I see tears running onto the mattress.
Her breathing slowed, as I feel her asshole relax around my shaft. She opens her eyes and met my gaze. I tilt my head slightly, and she nods slowly, never taking her eyes off mine. I nod back, and then look down to where my dick disappeared into her tight ass. The unexplored frontier. Not for much longer…I pull back until I feel the head of my cock just inside her puckered ring, then push forward again, sliding a third of my dick inside. ” Ummmmmm,” she groans. I realized how much this must be hurting her, and just as quickly noticed how much the fact of her pain is turning me on. I stroke in and out a few more times, slowly increasing my depth, until my rock hard member is buried inside her. Time to add some pleasure into the mix. Keeping my dick pressed all the way in, I reach my right hand down to her pussy. I slip my index finger into her pussy — still dripping wet and hotter than ever — just to get it slippery, then press it against her clitoris and start rubbing. She starts panting, and I took that as my cue to start fucking her ass.
I built up speed, going after her clit as hard as I’m pounding her ass. She starts to alternate moaning and shouting and then finally came, and extra trickle of her juices running down between her thighs and onto my knees. On my next out stroke she leans forward just far enough for me to pop out of her ass and climbed up onto the bed, rolling onto her back. She spread her legs and started fingering herself, gently, and motioned me up closer to her head. “Cum on my face,” she said. ” Please john yourself off and shoot your hot cum all over my face. I want you to cover me.” Still fingering her soaked pussy, her other hand starts pulling on her nipples. Her eyes locked onto mine. ” Please cum for me. Your cock is so nasty, it was in my ass, it was all the way in my ass, and I want you to cum for me, all over my face. You fucked me in the ass, you fucked me so hard in the ass, I want your cum.” All her dirty talk is having the desired effect. Between her nonstop stream of filth, her fingers running in and out of her dripping snatch and over her clit, I’m about to go over the edge.
I swing a leg over her so that I’m straddling her chest and lean in close to her face. What with all the vaseline on my cock, my hand glides smoothly up and down, up and down, up and down on the third stroke I blew my load. It’s entirely possible that I have never cum so hard before. The first shot hit her directly in the center of her face. She grimaces and her mouth opens slightly, just in time for my second jet to shoot between her teeth and hit the back of her throat. She starts choking and instinctively rolls on her side. I shot one last time, across her cheek and into her hair, and I’m done. I laid down on my left side and held her in behind her. She is still coughing as she turns back toward me and came in for a kiss. I feel my cum squishing between our faces as she probes my mouth with her tongue. Pulling away, she said, ” John, I have never been fucked like that in my life. I have never been with a man that can fuck me so many times in one night. I need a shower — care to join me?”
