This happened about two years ago. True story. I was 29 and newly single. I am an average dude, 6′ 160lbs. Fit but no gym rat. I was working as House Manager for a small venue and each performance brought in a new batch of volunteer ushers. Tonight’s group included a woman we’ll call Kim.
The volunteers sign up for shifts online and I never actually meet them in person until the night of the event. Most volunteers are bored old ladies looking for a fun busy night, cheap wine and a free show. Sometimes a cute soccer mom or college student will volunteer which can be fun flirting but nothing ever happens.
I first noticed Kim as I was giving my preshow lecture to the volunteers – house rules, audience size, length of show, etc. Her eyes are locked on me, a small smirk on her face. Short cropped strawberry blonde hair. The volunteers are asked to wear black pants and a white shirt. She’s in a tight pencil skirt and a tight white button up which slightly revealed the tops of her little round tits. My focus was totally thrown and I must have stuttered like a fool.
The night continues, the audience piles in. The venue holds 350 people and I’m in charge of all of them but I can’t focus on anything except this short haired vixen. I admire her body while she’s busy seating audience members. Athletic, tight. Around 5’8″. Under her skirt she wore black nylons with the line up the back and her ankles were slender and she had this walk that knocked me out. You know how some women are sexier by the way they carry themselves? The playful sway that just screams sex. Kim would bring a couple to their seats and the husbands would stare at her as she confidently walked back up the aisle, her little tight ass and slender figure hugged perfectly by her skirt. She was clearly older than me, if I had to guess I would say mid 40’s, but I never asked.
I’m not the most confident person but I couldn’t ignore the urge to get her attention. So what do I do? Stare like a weirdo, of course! Each time we pass each other during the preshow seating we locked eyes, her slight grin flashing quickly before she shyly drops her gaze.
So the lights dim, the volunteers grab their designated seats. I sadly watch her take a seat in the hushed crowd, no way for me to make any contact with the show starting.
I make my way back to the box office and begin my nightly reddit browsing ritual. The first act passes quickly enough, intermission spills the crowds into the lobby and 15 minutes later they shuffle back in. I don’t see her once. Act 2 begins and I start to forget all about her.
Nearly halfway thru act 2 I am still at the box office computer lazily clicking away when my attention is broken by the sound of the opera flooding into the lobby. This happens often, usually a patron with a small bladder using the lobby bathroom. The sound of high heels approaching and stopping at the box office desk brings a flash of instant nervous excitement to my stomach. Slowly my gaze rises from the computer screen to find her standing there looking sexy as fuck, smiling at me.
“Jesus, this is a long one. I should have grabbed a second glass of wine.”” she says
I mumble some sort of agreeable reply.
We start casually chatting about the theatre, different acts that have come thru. I ask about her, she works for the local college and signed up to be a volunteer for the free tickets. As we’re talking I can’t help but notice the looks she is giving me. She’s totally flirting with me and giving serious bedroom eyes. The sound of the orchestra swell and a loud applause breaks our moment – I have get back to work. This is my least favorite part of the night, the crowd lingers, people are rude and I have to be super polite. We head back to the theatre, I make an offhand remark about needing a drink as well.
The crowds clear out in their usually bloated wobbly way and I start dismissing the ushers. I see Kim buttoning her long black jacket and glances in my direction, I smile at her and she walks toward me. I nervously thank her for volunteering and ask if she’s interested in working other events.
“Sure. You have my email, just let me know when you need me or if you just want to get that drink.”
KABOOOOOM! And she leaves looking all sultry and sexy.
I know exactly what I’m going to do before I even finish locking up the theatre. There’s a show next weekend, I don’t need any more volunteers but I could definitely use a drink.
I wait a few days before sending the email. She replies a few hours later. The plan is to meet for drinks a few blocks away from the theatre after I lock up. Hol-y shit.
Saturday night finally arrives and I am a bundle of nerves. Is she really interested in me? The looks she was giving me say yes. Do I want to do this? It’s just drinks, who cares? She was interesting to talk to and that body, like a little sexy nymph.
I grow more and more excited as the hours tick by. I lock up and speed walk to the bar. I’m a little early, perfect, enough time to grab a drink and calm the nerves. Whiskey. Rocks. Now. I take a seat at a booth toward the back with a clear view of the door.
She enters wearing the same fashionable tight black coat with a high fur collar. And that fucking walk. She sees me, smiles and keeps eye contact all the way to the table. I want to fuck this woman and she hasn’t even sat down yet.
Under the coat she reveals a form fitting black and green dress, cleary proud of her athletic body. The dress has a slit up the side revealing black stockings. I notice her narrow ankles and heels, I’m not a foot guy but I fucking love narrow ankles.
We spend the next hour or so being coy and flirtatious and drinking cocktails, and I do my best to be as cool as I fucking can. She’s giving me that same ‘fuck me’ look and my confidence reaches new heights. I feel like somebody else. I compliment her dress and before I know what’s happening she has her shoe off and her foot is pressing slightly on my growing cock. I reach down and caress her ankle and up her leg. She smiles and looks down into her drink biting her lip and looks back at me. A comfortable silence passes.
“Do you have a car?” She asks.
“Yes, I parked in the theatre lot”
“Okay… Do you want to come back to my place?”
“Yes.”
“I need to get my car. I’ll meet you in the lot.”
I’m waiting in my car thinking about what a piece of shit I drive when headlights turn into the lot and a brand new jeep wrangler rolls up. I catch a glimpse of the lacy tops of her nylons. She tells me to follow her.
We drive about 15 minutes. I’m super nervous. Who is this woman? Where am I going? We turn into the driveway of a huge white building. She’s already fishing for her keys at a little side door as I am getting out of my car. We get into her place, which is a cute little apartment carved into an enormous New England home. I have no idea what to do next. I stand inside the doorway like a dumby as she takes off her heals and puts her keys and purse away.
“Want a drink?” She asks.
Yes, thank god. Suddenly my legs work again. She pours two Makers neat and we’re standing in the middle of her small living room. She looks at me over her glass with that fucking gaze and that’s all it takes.
I set my drink down and move towards her and she has a look on her face that says ‘good boy’. I pull her close and we kiss. I start slowl but she’s hungry. Obviously not interested in casual soft making out. She sucks on my tongue and my lower lip, kisses my chin and down my neck. I grab her ass hard with my free hand, almost picking her up, she moans with pleasure and breaks off.
“Grab your drink”
We move to her bedroom and she immediately starts taking my clothes off. She moans again as she runs her hands down my chest and deftly opens my buckle and with one quick motion my pants and underwear are around my ankles. She lets out another deeper groan, more like a grunt, and slowly starts stroking my 7 inch cock while looking straight at me. I step out of my pants and underwear as she, with her other hand, hands me my whiskey. I almost came right there. She hands me my drink as she lowers herself to her knees! She looks up at me, grinning, licks her lips and with a good grip on the base of my cock and balls, kisses and licks the tip before softly sucking the first few inches. She keeps a solid grip on the base which engorges my cock and makes my tip super sensitive. Her tongue swirls around my tip before she slowly starts sucking further down and then takes me all the way to the back of her throat. She doesn’t struggle or gag. This woman know exactly what she wants. I watch her, she’s still fully clothed, dress pulled up her thighs, one hand massaging my balls, her other hand has disappeared under her dress, she is taking my cock all the way down and back in a long slow rhythm like an angel. I end up leaning against her dresser sipping my drink, one hand behind her head as she sucks my cock and fingers herself. I moan and she gets excited and holds me tighter and starts sucking harder and faster. I stop questioning how I got there and watch this beauty bob her little pixie cut head on my cock. A soft moan escapes from her as she slows her rhythm back down. I ask her if she likes sucking my cock as I take a tight grip of her hair. She whimpers a quick ‘mmhmm’ reply, takes my cock out, looks up at me, ‘I fucking love this cock”. With my fingers still tight in her hair I plunge my dick back in her mouth and start face fucking her. I feel her throat resist a few times but I don’t stop. Saliva starts drooling down her chin and she’s moaning and gagging. I feel the first warm sensation of an orgasm so I slow down and she stands up. Her mouth wet and her eyes watery. We kiss and my hand goes immediately up her dress and finds her ass. She’s wearing a thong. I squeeze her bare ass and thread my finger thru her thong and down her ass to her soaking wet pussy. She moans in my mouth.
“Take this fucking dress off.” I command.
She turns away from me and glances over her shoulder. Her dress zips down her back. I take my time, slowly revealing her back which is almost completely covered by a huge koi fish tattoo. Who is this woman?!
“wow” I say
She giggles. “That’s the present I gave myself when I got my black belt.”
“You have a black belt in karate?”
“mmhmm” she purrs
She steps out of her dress and moves to the bed, wearing nothing but a black thong and black knee high stockings with lacy tops. Her body is super tone, not weird like a body builder, but tight. She has a more of a six pack than I do. I’ve never been with anyone super fit – for a moment a flash of insecurity hits me but quickly subsides. She’s kneeing up on the bed facing me, her hand slowly makes it’s way down her stomach to her pussy. Her other hand traces her nipple – her tits are small, a result of 0% body fat. She’s looking at me, waiting. I move to her on the bed and we start making out harder than ever. We lay down, she has one hand pumping my cock the other wrapped around my shoulder – her nails starting to dig into me. I turn her on her back, my cock stiff and aching inches away from her cunt. We continue making out, I move to her little tits and suck on her nipples. My hand moves down to her shaved pussy. She’s incredibly wet. I slide two fingers in and start working her, applying pressure with part of my palm. She moans and squirms. I don’t like the angle so i turn her on her side so her ass is against my dick – allowing me a comfortable angle to her clit. I pull her thong down and she wiggles out of it. I kiss her neck as my hand finds it’s way back to her pussy. She grinds her ass against me as my fingers enter her again. I work her clit softly with my middle finger- slowly teasing her before entering her again (I have really long fingers). She reaches between her legs and finds my cock pressed against her ass and pulls me between her so that the top of my hard dick is pressing against her hot wet cunt.
“Please… Please fuck me.”
“I don’t have a condom”
“It’s okay.”
The great debate goes on in my head. Should I? No. Do I? Yes. (dumb, I know)
I love to dirty talk and I love to tease.
“Do you need to be fucked?” I ask as I move my hand to my cock.
“Please…” she begs
“Say please again.” I start rubbing my cock on her pussy, she’s sopping wet, the top of my shaft is between her lips but I still don’t enter her.
“Please, please fuck me.”
I couldn’t take it any longer. I adjust my hips and my cock slides in. I remember feeling like lights were going off in my head. We both reacted in pure pleasure. She was so smooth and tight. I usually like to tease a woman an inch at a time but I went straight into Kim and she pressed herself down hard on me. We stayed like that for a moment before I slowly began to rock my hips keeping my dick deep inside her. As I get more and more turned on I begin to pick up speed – my dick getting farther out of her before thrusting back. She starts pushing her ass against me. I have one hand firmly on her wet mound, holding her close, applying pressure. My other arm is under her neck, my hand close enough to her face that her mouth finds it’s way to my index finger. This drives me fucking crazy. I hold her tighter and start pounding. She’s moaning while sucking on my finger. I am so turned on I feel my orgasm building again so I decide to switch positions.
I know I won’t last much longer so I decide to move into my favorite position. I sit up on my knees and shift her to her stomach – she moves obediently – then I slide her right leg up, bent at the knee, putting her pussy on full display. I position myself on top of her and place one hand on her bent right leg and the other on her head pressing her face in the pillow. She let’s out a deep moan of approval when she feels my weight pinning her down. I easily slide my cock back into her drenched pussy. I start out slow but she starts begging me to fuck her harder and harder. I keep my weight on her – her face pressed in her pillow. She starts moaning louder and louder and is begging me not to stop. Her moans turn to screams and I feel her pussy tense, I hold her tighter and pound her with everything I have, her already dripping pussy gushes and her body spasms and sends me over the edge. I pull out, quickly turn her over and straddle her face, plunging my cock into her mouth. She takes me all the way in and starts moaning as my cock throbs and I have one of the best orgasms of my life, she gags but takes every drop like the slutty little cougar that she is.
I collapse next to her. She snuggles up to me, clearly pleased. I glance around her room and, for the first time, notice the dozens of karate trophies.
The night doesn’t end there but this is probably way too long already. Needless to say we finish our drinks and continue to get to know each other.
Source: reddit.com/r/gonewildstories/comments/47s818/mind_blown_by_older_fox_mf_long