Hi All, been lurking around here for a bit. Finally decided to post this true story I wrote a few years back. Sent it to Penthouse Letters, but it never got published. I always thought it was pretty good. Tell me your thoughts? It’s sorta long, you need to enjoy reading.
So here I am, looking up for a second at my reflection in the mirror, contemplating how in the fuck I have arrived at this point after 53 years of life. Standing beside my bed, looking down at my cock slicing into the perfectly round, smooth ass of this delectable 21 year old blond, while she pulls mightily on my sheets clutched in her fists, groaning and squealing with each thrust. Amazing. My age and fucking this girl young enough to be my granddaughter. And she’s loving it.
I haven’t always felt so lucky. When my wife of 26 years was diagnosed with cancer life pretty much sucked. She was my perfect partner. A lady in company, a whore in bed. The first one to be naked, a total free spirit. She was more experienced than I when we met as babies, I was 21, she was 19. We grew up together. She loved picking up a girl at a bar, seducing her, then taking her home and showing her what two tongues, four hands, a cock and a pussy could do. We built a great business, a beautiful home, hiked, mountain biked, camped, traveled, had a wonderful life together. When she passed I felt like my life was over. I spent a year trying to drink myself to death, flying down the trails on my bike, hoping I would take out a tree and end the pain. Finally, with the support of some great friends, I pulled myself up and resumed living, getting out and meeting a few women, trying to fill the huge hole in my heart.
In short order I realized how hard this was going to be. The women I met near my age were carrying so much baggage. They were hardened from multiple relationships. They all thought they were sitting on a pot of gold. I live in a smallish town in the mountain west. There are many more available guys than women, and every female has a seemingly unlimited supply of dates. Few of them had taken care of their bodies. My wife and I had worked so hard to stay in shape. She looked as good at 45 as when we had met. I was the same. Working out 3 days a week, long rides in the mountains on my bike, skiing, hiking, had all blessed me with a rock hard body, the only hint of my age being some gray hair and a few wrinkles.
So I dated a bit, meeting some gold digging bitches. Tried dating a few younger women. They came encumbered with kids, ex husbands, and debt out the wazoo. Finally decided to just relax, let fate run it’s course, and perhaps one day love would come back to my life.
One weekend I drove up to Aspen to hang out with a buddy and ski. On my third day there I loaded on the lift with this hot looking woman, about 40 years old. She was in a thousand dollar ski suit, latest greatest skis, $400 dollar sunglasses. I immediately wrote her off as some rich Texas bitch, but soon changed my opinion after conversing on the way up the mountain. Turns out she was from Chicago, self made, owned a home in Aspen, single, out visiting for the week to ski. We hit it off pretty good, and I asked her if she wanted to shoot a run together. She said sure, so we did a fast cruiser. She could ski, so I suggested something a bit more challenging. We ended up skiing together the rest of the day, tearing that mountain to pieces. Bumps, powder shots, through the trees. Whooeee, did we rip it up. She could ski, zillion dollar suit and all. We ended the day at the base, giggling and snorting like kids, and I invited her to have a drink. She agreed, so we locked our skis and clumped in our ski boots into the nearest bar. We spent the next two hours telling our stories, I was thinking whoa, maybe this is the one. Then she lays this bombshell on me. Turns out she is a madam, has this stable of girls that she farms out to guys just like me. Older, successful men who can afford to indulge their desire for some younger poontang. She’s been doing this for 20 years, has made a fortune, and so sorry, but she is a lesbian and totally not into men. Wow, pop my bubble! She could tell I was crushed, she put her hand on my arm and said ‘Look, how about if I fix you up tonight. It’s on me.” I hesitated, having never been with a hooker, then said “What the fuck, why not?” We soon parted, but not before proclaiming our friendship and exchanging numbers, and she said she would call soon with the details of my date.
I returned to my room, got cleaned up, and settled in to watch the news. I had dozed off when my cell rang, and it was her, asking for my room number. She said Natalie would be arriving in an hour, was taken care of for the night, and to have fun. Well let me tell you. When the knock came at my door, and I opened it, my jaw hit the floor. There stood this vision of loveliness. A willowy brunette of about 25, in a short dress and heels, her jacket over her arm. She said “Hello, are you Jack’ I’m Natalie. And I’m yours.” I tried to stuff my tongue back in my mouth, mumbled something, and stepped aside. Natalie came in, closed the door, dropped her jacket on a chair, reached down to the hem of her dress and pulled it off over her head. Standing there in high heels and a smile. A perfect, taut, toned and tanned body with high breasts, puffy nipples, a sleek, shaved pussy. I drank it in. She sauntered over to the bed, sat down, and crooked her finger at me. I walked over, she unzipped my pants, pulled my erection out and started gently licking up and down it’s length. To say my sexuality reawakened that night would be the understatement of the century. We did about everything a man and a woman can do. I felt like a kid again, coming over and over and still able to get it up again. We ordered room service, ate food off of each other, fell asleep, awakened, and did it all over again. Finally about 3:00 in the morning I was done for and fell fast asleep. When I woke, she was gone, leaving a note saying “Thanks so much for a wonderful evening, I would love to see you again”.
I had a room service breakfast and started packing my bag to return home, smiling all the while. My cell rang and it was my madam. She said “Good morning, how do you feel this beautiful day?” I said ‘i feel like a kid again, thanks so much”. “Well, I was happy to do it, I hear you are quite the stud. Keep my number, call anytime you would like some company. And let’s do ski again real soon, OK?” I agreed, said goodbye, and headed out the door with a spring in my step. Realizing all the while that the hook had truly been set. She would be getting lots of business from here on out.
So began a new chapter in my life. I did continue to occasionally date a few locals in my town, but the pressure was off. Whenever I felt the urge, I would make that call, and a day or so later would pick up a drop dead gorgeous woman, never over 30, at the airport. Squiring her around the town, having drinks and romantic dinners, getting perplexed looks wondering where in the hell I came up with these dates. Then driving out of town to my forest home to make love for the entire weekend. Sure it was expensive, but I could afford it. Besides, in reality it was probably cheaper than getting in a relationship with a gold digger. And damn good for the ego as well! And that is how I got really accustomed to doing young women. So now we get back to the beginning of this story. How I ended up with this gorgeous blond in my bedroom. And she isn”t a hooker!
I had gone for a ride on one of my favorite trails. It follows a stream up into the mountains, then climbs high up onto this ridge to an overlook, then you can do a loop or head back down. I had elected to do the loop, which when combined with the ride to the overlook made for about 8 miles of ripping downhill. There was a fair amount of traffic, lots of hikers and other cyclists. Usually there are some hotties on this ride, so I was keeping an eye out. Nearing the trailhead, a glimpse of color moving through the trees in front of me. Closing in, I realize that it is a young woman, my favorite thing in the world! She is running, and I mean really running. She looks like a gazelle going down the trail. My eyes go to her ass, barely covered by a pair of tight, short waisted, short legged lycra shorts. Her ass cheeks are literally hanging out, her butt crack peeking out at the waistband. My God, firm, tight muscles pounding down the trail. Long, lean tanned legs, a slender waist with a small tattoo in the small of her back. A purple jog bra, long blond hair in a ponytail bouncing back and forth. And that ass. Oh my God. I slow down, try to ride quietly so I can take it all in. I get closer, can see sweat trickling down her back into her shorts. Quiet, want to look at this. But I hit a rock and my chain jangles, she looks back and steps off the trail. I sweep by, smiling, saying “Thanks much, good day.”
Another quarter mile to the trailhead. A few people down on the other end of the lot getting ready. I open my car, lay my bike down, start getting my gear off. Thinking ‘Man, I have got to say something to that chick.’ I know I look good in my lycra shorts, tight jersey, helmet and glasses. Younger than I really am. Here she comes. Now I can see her front. Beautiful face, big green eyes, full lips, smallish but nice tits with pointy nipples showing. Flat stomach with a belly button ring. Sexy, what a package. I say ‘You about gave this old man a heart attack.’ She gives me a quizzical look and says ‘I’m sorry??’ I say ‘Those shorts. Sight for sore eyes.’ She gives me a crooked grin. Says ‘Thanks.’ She goes over to her car, opens it up, gets a jug of water out and drinks, looking at me. It spills and trickles down her chest into her cleavage. I look back while sitting on my bumper changing my shoes. She gets her flip flops out, drops them on the ground, looks at me, turns her back and bends over to untie her shoes, pointing her ass right at me. I can see the cleft of her pussy in the crotch with a wet spot right in the center. Her ass cheeks are staring right at me. She takes her time, sort of wiggling it around while pulling her shoes off. I lay my bike in the back, pull my helmet and Camelback off, grab a bottle of water, and walk on over. She has straightened up, I look at her feet. Nice. Smallish, beautifully manicured. I could lick them. Right now. She looks right at my face, I can see her looking at the gray hair, then her eyes travel down to my hard chest, biceps, flat stomach, my bulging quads in my shorts, and my crotch. That’s another place I have been blessed. Really blessed. Her look is not disapproving. She doesn’t seem put off by my approach at all. I decide to go for the gold. It’s gonna work or not. I say ‘Have you ever had a tongue shoved up your asshole?’ just as she takes another drink. She chokes, water spraying out, on me too. Her face turns beet red. Uh oh, blew that one! She coughs for a second, tears coming from her eyes. She says ‘Well, no, and if that’s a come on line it’s rude as hell.’ I said ‘Not a come on line, an offer. You have the finest ass I have ever seen in all my years. I could make love to it until you beg for mercy.’ ‘You’re old enough to be my dad.’ she says. ‘Naw, your grandfather. But you’ll never find a punk your age who will make love to you the way I will.’
She starts to look angry. Starts to say ‘Just who’—-stops. Blushes. Gulps. Says ‘I can’t believe anybody would say that.’ ‘I figured what was there to lose. Wanted to get your attention.’ She says ‘Well you did that, all right.’ ‘Look, it was an impulse thing. Not premeditated. Never done that before. Your ass just drew it out of me.’ ‘You really think my ass is that good?’ ‘Sweetheart, let me tell you. I’ve seen some asses in my day, and that is one mighty fine butt!’ ‘You would really do that? You can’t be serious.’ ‘In a heartbeat, just try me’ I say. ‘Maybe I will, you never know.’ She pulls a notepad and pen out of her car and thrusts it at me. ‘Put down your name and number, I gotta go.’ I do so, hand it back, my hand grazing hers. She looks like she got shocked, her hand jerks. She turns on her heel and gets in her car, I move out of the way and she backs up and drives away without looking at me again.
Oh well, nothing ventured, nothing gained. Never will hear from her I think as I start my car and head home. Hmm, maybe time to make that special call again, she sure made me horny. Got home, unloaded the bike, took a shower, grabbed something to eat, and settled in front of the computer to check my email. The phone rings. ‘Hi, it’s me’says a female voice. ‘Me who’ I respond. ‘Jessica, from the trail.’ ‘Oh, that’s your name, didn’t think I would hear from you.’ She says ‘Are you serious? You know, about what you said?’ ‘Dead serious, I wouldn’t joke about something as nice as your butt.’ ‘Well, I can’t believe I’m calling you, but what you said is making me so horny I can’t stand it. I’m laying on my bed right now rubbing my clit and my asshole.’ I said ‘Don’t waste an orgasm, leave that up to me. You want to come over?’ ‘Yeah, I think I so, how do I get there?’ I give her directions and starting running around picking up the house, making the bed, trying to make it presentable.
I live a ways out of town, so it took her about 30 minutes. I hear a car and peek out to see her little Subaru driving up. Ran down, opened the door and stepped out onto my porch. She sat behind the wheel looking like a deer in the headlights. I walk over and she opens her door, she is shaking she is so nervous. Better play nice here or she is going to bolt. I say ‘Hi, welcome to my home.’ She looks behind me and I can see her taking it all in. If I say so myself it’s pretty spectacular, we built it ourselves, my wife and I. Massive beams, stone, high pitched roof with lots of windows, set in the trees right on the edge of a cliff looking down into the valley below with views of soaring peaks. She steps out and I get to see that body again. Dressed in tiny sweatpant shorts with the rolled down waist. They look like a gust of wind could make them fall off. Firm, tan thighs. Those dainty feet in jeweled flops. A tight, very thin tank top ending at her navel, her dark nipples clearly visible. Yum.
I extend her my arm, she takes it, and we walk inside. She takes in a breath when she sees the great room with the views beyond. I guide her over to the kitchen and offer her a drink. She says ‘Sure, I need something to steady my nerves.’ So I make my signature margarita, the recipe straight out of Mexico. She sips it appreciatively, I ask if she is hungry. She thinks for a second and says ‘Oops, I forgot to eat. I’m starving.’ So I whip up some fresh guacamole and chips, quickly make her a sandwich. She eats ravenously, nothing dainty about her appetite. I can see her visibly relaxing as the alcohol hits her bloodstream and she realizes I am not going to bite her. She finishes and wipes her mouth, lets a little girly burp and giggles.
‘Ready for a tour?’ I ask. ‘You bet’ she replies, standing up, obviously a teeny bit tipsy. I show her around, the decks, the hot tub, the media room, the workout room, the spare rooms, finally to the master. She oohs and aahs, visibly impressed. We end up in the master bath, she loves the clawfoot tub, the mirrors, the huge shower with a bench, multiple heads, and steamer. I offer ‘How about a steam shower?’ ‘Oh, I already bathed before coming over.’ ‘Not like this you didn’t’ I reply. She shrugs, gives the tiniest push and those shorts hit the floor, followed by her top. Amazing. Just the sleekest, smoothest body. No lumps, no bumps. Not a tan line to be seen. Perfect high cone shaped tits with hard, pointy nipples. That flat stomach leading down to the V between her legs, no hair down there. I turn on the steamer and the showers. Peel my clothes off. She takes it in, looking me up and down just like I did her. Approvingly. My cock is swelling to attention, she reaches out and gives it a squeeze and smiles. I lean in and gently kiss her, taking her lower lip between my teeth and running my tongue over it, then drawing back till our lips are barely touching, and breathing into her mouth. She sighs, I feel her melting into me. The water is hot, so we step in. I grab a loofa and begin soaping her down. Paying attention to every crevice, every curve of her body. The room is filling with steam, I stroke her legs, her back, around the front, her tits, belly. She lets out little squeaks and moans. I sit her down on the bench and take a foot in both hands, scrubbing and rubbing it, spreading her toes apart and flexing them. I look up and she is leaning back against the glass, her eyes closed and a contented smile on her face. I rinse her foot and put it up to my mouth, slipping my tongue between her toes and sucking them, one by one. She jerks and opens her eyes, watching me with fascination. ‘Oh, I’ve never felt anything like that. That’s nice!’ I run my tongue over the sole of her foot, up into the arch, admiring it’s delicate form. She giggles and lets out a squeal of pleasure. I do the same to the other one, eliciting the same response.
I stand her up and tell her to bend over, resting her hands on the bench. She looks at me, wondering what I am up to now, but complies. I soap my hands and begin squeezing that butt, rubbing the fleshy globes, admiring how firm and round they are. Slide my whole hand between her legs, spreading her cheeks. Then I flatten my fingers and begin massaging all around her anus, rubbing in circles, just teasing the crinkled center then backing away. She groans and spreads her legs, giving me better access. I tease her hole with my middle finger and it magically opens up and sucks it in. A sharp intake of breath announces her pleasure. She pushes back as I insert a second finger, she groans, then says ‘Oh fuck, that’s good, oh fuck.’ as a third one goes in, stretching her asshole wide. I look down and can literally see inside her between my fingers, I twist them back and forth and watch the soap suds working in and out. I ease my hand out and she looks around, disappointed. I hand her the soap and say ‘Now it’s your turn.’ She gives a devilish grin and reaches for my cock, soaping it’s length, reaching back and squeezing my balls. Then she turns me around and pushes me over the bench, and repeats what I did to her. Stroking my asshole, building up to three fingers while jerking my cock at the same time. I groan, concentrating to keep from coming. It feels so good. She withdraws her fingers and we rinse each other, stroking and caressing all the while. I turn off the water and steamer and grab towels, drying her off while in the warmth of the shower. We step out and I sit her down on the makeup seat and start to lotion her body, smoothing the cream on, starting at her feet. Admiring every inch of her. She sighs and aahs, eyes closed, enjoying the sensation. She tries to do the same to me, but I am impatient and help her, letting her lotion my back only. She does do my butt cheeks, squeezing them like I did hers.
I lead her to the bedroom and push her facedown on the cover, grabbing a pillow and putting it under her hips, elevating her ass. I have to stand back and admire the view. Oh, what a body. I lean over and pull her cheeks apart and look at her perfect little pink crinkled rosebud. Her pussy opens up and I can see her juicy center, small tidy lips and the pearl of her clit. Wetness is oozing out and trickling down to the pillow. I lower my head and scoop it up, running my tongue over her clit, through her pussy, and up to her ass, centering the tip on the hole. She lets out an animalistic howl as I spear my tongue as deep into her bowels as it will go. She humps back at my face, grunting and moaning, making incoherent noises. I bury my face between those glorious globes, fucking her ass for all I am worth. I back away and roll her over, lifting her feet up to my shoulders and spreading her wide. Her pussy is pouring juice and I jamb my face into it, sticking my nose into her gash, rubbing juice all over, putting my whole mouth over her pussy and sucking. She is thrashing around, her feet beating a tattoo on my back, her hands pulling on my hair, trying to get me deeper inside. ‘Oh, oh, oh! Oh God, oh fuck, oh shit. Never, ever, don’t stop! Oh, oh, Gaaaaawd!’ she screams as her body convulses. I have never seen an orgasm like this. She twists and turns, clamping my head between her thighs. I can barely get a breath as she pulls on my hair, her feet thumping on my back. At last her pleasure subsides and she collapses, breathing hard. I manage to get my head out and slide up over her body, laying on her, and kissing her gently. She starts sucking my tongue, then pulls away and licks my face, cleaning her juices off.
‘I had no idea. Nobody has ever done that to me. That was incredible’ she says as we hold each other. ‘Told ya those young punks don’t know what they are doing’ I reply. ‘And that was just the beginning.’ Her eyes grow big as she contemplates the possibilities. We cuddle for awhile but my erection is growing impatient. She starts stroking it and slithers down my body and starts to suck me, tickling my balls and then slipping a finger down to my asshole. She shifts around and pushes my legs back and starts to nibble on my balls, taking them one at a time into her mouth, sucking right to the point of pain. She then delves lower, pushes my legs back to my chest and starts to lave my asshole with her tongue, swabbing all around it, puts her mouth right over my anus and sucks, hard. All the while jerking on my cock and squeezing my balls with the other hand. Her tongue penetrates the tight ring of my rectum and I can feel her licking the inside. Wow, what a feeling. Now I know why she got off so hard. She continues tonguing and jerking and I have to tell her to stop, that I am getting close. She just starts to work all the harder, pushing me closer to the edge. I finally gasp as I can feel my sap rising and she jambs her mouth over my cock as I explode. She gulps frantically as my semen fills her mouth, trying to swallow it all. But it’s too much and some trickles out the corners of her mouth. As my pleasure subsides she comes up and plants a big kiss on me, sticking her tongue in my mouth and giving me a healthy taste of my own jism.
We lay on the bed, cuddling each other. I ask her where she learned that trick, she says just now, she’s a fast learner. We start kissing again, I make love to her mouth, her ears, her neck, work my way down to those remarkable, neglected titties. They are borderline hard, they are so firm. Her nipples are very responsive, perking right up when I suck and lightly bite them. She squirms when I do so. I keep going lower and end up back at her pussy, examining it. There is no stubble, no razorburn, I ask what the heck’ She says she had it lasered. Hurt like hell, but worth it. Did her legs too, never have to shave again. I rub my face on her crotch, it is so smooth. Gently start to nibble on her lips. She has the prettiest pussy, tidy little lips that spring open revealing her pink center when you spread her legs. And her taste, just like honey. So fresh and clean. I start scooping my tongue through that pink gash, drinking it up. She starts thrusting her hips upwards into my face, I end up back at her ass. Just can’t get enough of it. Gently lick and suck at her nether hole. She is moaning again, I roll over onto my back and pull her over on top of me, making her squat on my face. Her weight pushes her asshole down onto my tongue and she wiggles around, seating it down deeper. Her pussy is dripping honey down onto my face. I pull my tongue out and slide it over her asshole, through her pussy, over her clit, right up to her belly button. She shivers and lets out an animal like groan.
‘God, you are nasty. I love it’ she says as she plunks her ass right back down on my tongue. I think she’s getting used to the idea! Smooshes her butt onto my face, humping me. I am in heaven. This delectable creature giving herself up to me. Suddenly she climbs off, spins around, and aims her butt up in the air. ‘Fuck me. Stick that hard cock right up my asshole. I want it now!’ Always one to please, I get behind her and slide it into her slippery cunt. Goes right in to the hilt she is so wet. Couple of strokes to get lubed up, then pull out and aim it at her asshole. I try to be gentle and slow, but she pushes back and impales herself. ‘Uh, uh. So good. Oh, I never knew. Oh, sweet Jesus fuck me please!’
And so here we are at the beginning. My lucky day’and night. Jessica and I spent the next 3 hours pleasuring one another. After my fourth orgasm I was spent, my cock refused to rally again. We fell asleep with our faces buried in the other’s crotch, waking up in the morning encrusted in come and pussy juice, the room reeking of sex. We opened all the windows and showered again and ended up back in bed for a slow, gentle lovemaking session. When she left I told her that I expected nothing from her, our ages are so different. She said she agreed, but called that night asking to come over. We again spent the night frolicking until the wee hours.
We both realize that this is a temporary thing. But for now it works. Jessica is in college, was working three jobs to pay for it. I have happily removed that burden from her, giving her money for tuition and living expenses. She tells her parents that she is my personal assistant, so they are happy. Little do they know how personal she is! She occasionally dates other guys, has actually met one that she has been educating in bed. It may turn into something. She has brought a couple of girlfriends over and we have had some wild times with them. She says that when she graduates arrangements will be made for a successor to take care of my needs.
I actually met a woman the other week in her mid 40’s. She is way into mountain biking, we have tons in common. We have been on several dates and all is going well. She revealed the other day that she is bi and has a predilection for young women. She hasn’t met Jessica yet, but I can’t wait to see the sparks fly when they do. This could be interesting!
J. R. from high in the mountains of Colorado