What is the best sex you have ever had (in detail)?
07.06.2025 20:19
I love that she can’t control her body, but that I can, she’s fully giving herself to me. I’m over her back, my cock pressed in between her asscheeks and she whispers out of the desperation that I very much can hear in her voice, “Oh, God, just please.”
Fuck, she’s hot. Very.
I need to cum. Sandy is making it fucking impossible not to. I barely have time to gasp out, “Babydoll, you’re making me cum!” in as much warning as I can give her. But I think she knows this. She had her eyes closed before as she sucked, but they had snapped open and stared into mine. She has been making muffled whimpers of greed around my cock for the last five seconds before I say that, I’m up on the balls of my feet as she was before. My muscles have been uncontrollably clenching and it’s been making my cock swell harder in her mouth for a second each time I flex. She’s felt that in her pussy and especially while holding still and had my cock completely buried inside her ass. I’m in those moments where I’m at my hardest and biggest before I can’t stop myself any more. She now has a bare three seconds to decide how she wants my cum. I silently beg her to not stop and let me flood her mouth.
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There’s a problem here, Sandy and I are running out of time. Another CNA may walk over to our building to get something they need, or the ambulatory residents have been known to poke their heads around corners if for nothing more but to talk with you a little at 3 AM. While the laundry room is in a corner, the door has been open this whole time. It’s already risky. As Sandy comes down, I gently say “Babydoll, we need to hurry.” Sandy looks at the door and shakes her head yes. But then she looks up at me as I’m standing over an absolute goddess, with a hopeful look and shakes her head no.
The next time I saw Sandy, she was back to normal. Of course, my wife was working that night, so I don’t know exactly if Sandy knew what she did to me or not. But, that show sure as hell was nice, even if it wasn’t intentional on her part. Report gets done, I go home. My wife is flirty tonight, I’m stroking my cock as she’s telling me what panties she’s got on and how she wants to get fucked. My phone dings again. I look, it’s a text from a number I don’t know.
Sandy is waiting, but I don’t answer. Instead, she feels my fingertips of both hands lightly slide up both of her legs, starting at her ankles, over her calves, across the backs of her knees, spreading my fingers across the backs of her thighs, up around the curve of her ass, over her lower back, until I switch to a long lick up her spine and my hands switch to her wrists, caressing down her forearms and back up to her shoulders. I know it’s tickling her but it’s not when done in that intimate way. As I bite the back of her neck, she’s almost bouncing on the balls of her feet, her rings on her fingers making erratic tapping noises on the washing machine, panting very fast.
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Because I am that Satan himself that they say. I take no pride in saying that for this situation. I have cheated on every woman in a serious relationship that I’ve been with. Since ending it with Sandy, I have no more than stayed within my wife’s boundaries as to what is allowed with other women.
I damn well don’t believe in Karma or reincarnation, fate or destiny. Nor gods, or heaven or hell to spend eternity in. If something created us it’s not revealing itself to us and never will.
Absolutely hot as fuck, primal as hell. She was working me up to fill her ass to overflowing when her legs finally gave out and she almost collapsed. I almost missed it, barely caught her, tearing my arm out of her teeth, letting go of her hair and wrapping both arms around her middle. I literally have to hold her up so she doesn’t hurt herself. She’s still on my cock, I can feel her muscles spasming around my dick. Her head lolls back, into the pocket of my shoulder as I adjust our balance together.
I follow Sandy to the laundry room, where I grab her from behind, spin her and kiss the hell out of her. She’s actually panting into my mouth as our tounges tangle, touching, teasing. It’s slow and gentle, but wanton and desperate all the same. She’s pressed up hard against my cock, pushing into it. My mouth slips down to her neck and she lifted up on tiptoe when I bit her. I have an asscheek in each hand, slipping my fingers up and down where they meet her inner thighs. Bit up her neck and sucked on her earlobe. She shuddered and shook hard, moaning and whimpering softly, making me hold her up. It lasts for a lot longer than it should. Girl came just from sucking on her earlobe. Just quivering all over. We haven’t even started yet. Damn.
I watched her gather her clothes and with an adorable peek around the corner of the door, she moved like a cat to the resident shower across the hall.
This is yet another first for me, certainly not in ways that a woman has never played with herself in front of me, but the fact that I’ve had to ask or command any particular woman to pleasure herself under my focus. I have had past play partners, ex’s and my current wife that I can sense their hesitation and given hundreds of webcam shows and phone sex calls with women who I can hear but have never seen more past a quick picture before or after.
I want to slow down a minute to express why Sandy was unusual to me. That question was one. It’s simply not asked in real life, like that, on the first sexual encounter. Sandy was not a porn star making a few grand for having her ass destroyed on camera by some black guy that has a big fake dick.
Not every woman does everything. Matter of fact, none of them readily do it all. If she says yes to some or most things, she’ll eventually say no to one as a hard limit. It’s not her fault. It’s human nature, but as Mr. Jaeger sings, “You caint always get whatcha want, but if ya try sometime, ya might find, ya get whatcha need!” So.
Sandy’s question implies hope that I would fuck her ass, she’s badly wanting me to. That she trusted me with it and that she found true pleasure in it as well. Of the 250+ women I’ve had sex with, none other was like her in the ways we did things together. The real test here is Sandy’s. More on that latter.
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I hear Sandy’s sharp intake of breath and she goes absolutely stock still as I push my tongue into her tight little hole. She’ll later tell me no one has had their tounge inside her and was scared that if she moved, I’d stop. A minute of licking, sucking, tickling and probing and Sandy is starting to impulsively slap the top of the washer with both hands. I stood up, one hand guiding the head of my cock up her thigh getting it covered in her, a quick flick across her clit, slipping so easily into her pussy to get it slick to make it easier for me to fuck her ass. She hisses like a cat, “Oh, fuck you! Don’t tease! as I slip out of her pussy and smear both her juices and my precum at the tip of my cock on her asshole. I push the head of my cock into her as I wrap my fist around her hair at the base of her neck. She’s so tight that I feel the ridge of the head of my dick go past the opening and already being squeezed.
Sandy sits closest to me, as always. She has my full attention tonight and I think she knows it. I’m trying not to stare as she kicks her shoes off her feet.
As she moves her head forward and takes one of my balls in her mouth, she presses a finger on my taint, her other hand moving to press the shaft of my cock to her cheek. That happens to be the side her hair was on and from what she’s doing to me, she just got a lot more precum that just got on her ear and in her hair. It’s so goddamn dirty, I don’t hold myself back from rasping, “Oh, fuck yes, my little slut!” This isn’t a term I use regularly with another woman who doesn’t know that’s my term of ownership, endearment and as a compliment that you are very much pleasuring me. But I now have no foreknowledge of how Sandy might take it.
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She finished and she was simply the most beautiful woman I’ve ever seen. She was sweating, her mascara had run, hair in a tangled, cum sodden mess and draped across her chest and down her belly, her pussylips and ass still swollen, legs still open and trembling from exhaustion. I knew then to go to her, putting myself her and the wall, sinking down behind her, back to my chest, my legs touching outside of hers, my arms crossed around her chest as she put hers the same over mine and she wove her fingers into mine. She breathes as I do, and I could feel her heart rate match mine. We sat in silence, neither of us really needed to say anything, just calming each other.
She unlocks her leg from mine, hands caressing my face and neck. As she kisses down my chest and belly, her fingertips follow with the same light touch I used on her. It’s fair game torture and she’s sending little electric shocks through me, before sinking down into a crouch in front of me, her knees open wide around my legs. This intrigued me because 99% of women sucking my cock are on their knees. Sandy is either going to be getting a suction cupped to the floor dildo in her pussy or ass to ride while I see if she’ll cum with my cock in her mouth. Or if she’ll bounce up and down on my cock as she straddles me so I can watch my cock fucking and cumming in her holes later. Sandy had crouched gracefully too. She’s got good balance, up on her feet and wide open like that.
My wife has referred to me as Satan himself when it comes to my desires and the ability to achieve them. She is not the first person to say something similar. Matter of fact, it’s not rare to hear from a lot of people. Even my Mom has said that. As Sandy sits at her normal spot at the table for report closest to me, I’m on the couch in my usual spot too.
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I’m waiting for her. Again, and again.
I do and she puts me inside her, pushing her hips and ass back to shove me in deep. I don’t want her to go too fast. I back off just a little. I’ve got half of my dick inside her pussy, slowly getting another inch in when I feel her clamp down on my cock and she’s arching her back. She’s cumming already and it’s not even been five seconds.
My body generates more semen by far than average, meaning that where a normal guy gets 3 or 4 spurts, I get 9 or 10. Couple that with frequent masturbating and having sex to help from getting blue balls, I have wicked strong PC muscles and have been known to flip cum about six feet. It’s either a blessing or a curse, it leads to a lot of possible responses.
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I met my current wife in the lifestyle and she has indeed done a good job indulging me of my many fetishes, there are some that are emotionally uncomfortable or physically impossible for her to perform, again, not by any fault of her own. Brief examples of this are anal sex, where I’m simply big enough for a woman who does not find true pleasure in to avoid it with me. Or a latex allergy that her five inch wide stocking tops burned the skin of her inner thighs during our wedding night. Little details turn into big ones. She is also a full ten years older than I. That being said, she does keep me satisfied quite enough that I was neither searching for nor expected to have an affair.
A lot of women don’t take that, some backing off of me if it starts to get painful because of my size. Never Sandy. Not once. She took anything I ever gave her.
Sandy pulls them off and up, stretching them until her knees and quickly tucks her calf and pulls her foot through. She just leaves them hanging from her other knee in her need to both show me all of herself and getting her own satisfaction in that need.
I was in my early 40’s during the economic recession and jobs were hard to find. My wife and I both took the CNA course, passed it and we’re working in the same facility. They would not allow us to work the same shift, with me on second and her on third. My wife worked with a woman her age named Sandy and became friends with her.
I let Sandy break the silence. She took our hands together and gently bounced the backs of hers on the floor to each side of us. She said “Mmmm, damn, the house is yours while I clean up. I want more of you in the future. With that, she bounced her hands twice more on the floor and broke our grip.
I’ve had women laugh of amazement all the way to getting pissed because some hit her face and that was a hard limit. I’ve permanently wrecked furniture or expensive lingerie outfits. I can choke a woman on it if she can’t swallow it fast enough, if she spits, or likes it on her face or body, it’s a pretty big mess. If she wants to avoid it entirely, she needs to point that thing somewhere safe. She’ll either love it or hate it.
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The door closed, but not before I caught her face, whispering “Damn!” I got redressed the best I could, my forearm where Sandy bit me started to sting and ache. Not my first time I’ve been bitten, but the best time so far. I’ll have to tell my wife a resident bit me, it happens. I needed to do a quick round, we got very lucky we had the time we did.
What I didn’t know was my wife was telling Sandy about all of my fetishes. Teaching her is really what it was. My wife was off work for a day, I see Sandy for report. Very long hair down, made up just enough for work, tight pink v neck top, black capri leggings that showed off her previously unknown fantastic legs and ass. She has to walk by me, I can see a glimpse of the seam of her leggings pulled tight against her pussylips. She’s got these little pink leopard print ankle socks on along with her running shoes. If you can’t tell, I’m quite the clothing fetishist. Lingerie especially, but what Sandy had on was sexy as fuck and she looked really good. I’m sitting on the couch away from the table, so I have to look over the back of the couch to see. Which turned out to be exactly the place I needed to be.
This isn’t your average “I had a MFM threesome and it was great, yippee!” type tale either. Hell, it doesn’t even have a good outcome in its ending.
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The report takes three minutes. Sandy doesn’t realize I’ve already cum all over her socks because I fucked her arches and that her toes rubbing the head of my cock drives me crazy enough to cum in real life when I have the opportunity of a getting a foot job with a woman. I have to wait a minute to stand up, or every woman in that room is going to see my dick making a tent out of my pants. I say my goodbyes. Sandy smiles and waves, like always.
My cum is leaking from both sides of her mouth, Sandy actually opens it for me to see that her mouth is full and lets me watch more shoot into it. She loses a lot down her chin before trying to swallow again, the next spurt splattering her nose and closed mouth before it drops straight onto her chest. Sandy swallows and takes my cock in her mouth again. Two or three more spurts and she abandons the idea that she can keep up. She makes both the sweetest and nastiest show that I’ve ever seen as the remaining cum splashes onto her chest and runs down her belly. I can’t possibly imagine trying to match that sight with any other of my previous partners or any one of a thousand porn stars.
But Sandy always gave and continues to give me the certainty that I’ve been with her over centuries. There’s just no way to know how or why that is. And I know from that feeling alone that she knows that too.
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I lowly growl back, an inch from her ear, “You’re mine now, you’ll have anything you want of me, Babydoll.” She doesn’t yet understand that I want this as badly as she does. I kiss my way down her spine, my fingertips brushing along her rib cage and sides. I drop to a knee as my hands move on the curves of her hips, then to cup her ass. Pulling her cheeks apart, I can see her wetness dripping down her leg. I taste her again, licking up, onto her clit, through her pussy lips and up to her asshole, before I suck in and flick my tounge on it like I did with her clit before.
With all of that, it only took her less than five seconds to cum hard again, nearly knocking me down in the process. Not waiting, she pulls me up and turns around, putting her leg up on the washing machine. Her ass in that g-string is sexier than I’ve ever seen a porn star’s look, along with her wet pussylips, open and ready. I fumble with my scrub pants, trying to get my cock out. Her hand is moving between her legs, signaling me to put my cock in her hand.
As I slipped one hand down over her ass and then the back of her leg to hold her, I understand that this woman has just locked herself to me in every way, without a word. As I look down at her, both of us very still, Sandy’s eyes are intently searching mine to see if I comprehend her meaning. Not breaking her gaze, I whisper “I know.” Three more seconds of stillness and she very slightly nods, eyes sparkling, pecks me twice on my lips and says, “Let me.”
I’m taking in hungry eyefuls of her for the first hour, until we’re in a resident’s room. I had to help Sandy get the resident into the bathroom. We’re both sitting on the bed waiting. Sandy kicks off her shoe. Massages her foot. Watching her gets me hard as fuck and Sandy says, “Oh my God.” under her breath. We still wait, Sandy watching me squeeze my cock through my scrubs as I watch her play with her feet. My pants have a pretty big precum stain on them and Sandy hasn’t even touched me yet. Finally finish and get the resident back in bed.
One way to lose a new partner real fast is to give her a surprise mouthful of cum. I ask ahead of time out of etiquette and respect. The other is a medical condition I have called hyperspermia.
Sandy kicks off her shoes, stretches both legs out together as I watch, arches her feet and points her toes. I see the tiniest bit of her smirk as she lifts her ass up and tucks a foot underneath herself. She’s sitting on her heel and almost imperceptibly grinding her pussy on it. I watch her breathing speed up and she’s an absolute master of her control when only I know she’s cumming again. She turns to look at me when no one is looking and actually bares her upper lip and teeth at me.
My phone dings again. My wife. Telling me she’s having fun with Sandy, who’s showing off her ass to some guy she likes in Boston. My wife is telling her she’s making me cum talking about her panties. I get a few more shots, Sandy’s pretty pussy with a landing strip, panties pulled to the side, that fabric tight on her clit. My wife thinks she’s making me cum? Not that time. But Sandy is.
She backs up against the washing machine, pulling her leggings down. She has that G-string on. Literally takes my head and guides it down, putting me on my knees in front of her. Grab the fabric and pull it to the side. I dart my tounge out and tap her clit with it. She won’t take the tease. She greedily shoves her pussy towards me and I respond by sucking her clit into my mouth. I repeatedly flick it with my tounge as I suck, reaching up to slip my fingers inside her. I can feel her g-spot on the front wall of her pussy and put pressure on it, the back of my hand on both of her asscheeks and pushing.
It’s all as she sits on a floor in an open to being discovered environment, frantically reaching her most powerful orgasms she’s ever had. Sandy has two fingers in her ass and her palm over her pussylips and clit, hammering away, her body covered in the cum of a man she barely knows yet somehow knows everything about him and he of her, who’s watching her in her depravity with the intensity they both have needed but never known. I’ve regained all of my senses and I’m getting hard again watching her. I’m well aware of how I want more of her now right fuckin now, but I let her finish. If she had reached out for me, I’d have gone to her. She went through making herself cum 3 more times as I watched, definitely not like she was relearning how, but just had to.
Holy fuck, this girl has gorgeous feet. Really high arches, pretty toes. Super sexy in those little pink socks and she starts to flex and point her toes like they hurt. Roll her ankle around, point. Cross her legs at the ankles and do it with both. Damn. Great legs. I’m watching her thigh and calf muscles flex. My God.
I’m getting hard in my scrub pants, fast.
She’s not the woman on a lifestyle chat site who says she loves anal but you’ll never actually get a finger in her ass, let alone your cock, before she says no. There’s many like that.
The web abounds with women who run OnlyFans or Chaturbate accounts, being paid to perform for you and it is simply never done out of a need for intimacy or derived from a greed of her own pleasure, no matter how well she may act the part. My wife and I have been in that part of the of the industry with the required separate profiles in order to run a couple’s profile. I’ll be the first to assure you there is no intimacy or pleasure found when your wife kicks you out a room to get paid to do things that I wouldn’t ask her to do out of knowledge or respect for her limits and she sure as shit didn’t like me compromising my Alpha’s character for a whole lot of gay guys paying me to act like someone I’m not and that she didn’t either want or love.
I’m both dominant and an Alpha for every minute of my life and in every function I perform, whether roleplay and real life. Sandy is not the masochist that I will take her ass to enforce punishments or simply to use for my own pleasure, no matter if she likes it or not. I can and I do.
If I’m Satan himself, she’s Satan herself. This is gonna be one hell of a rabbit hole road trip. As we head to the parking lot after report, we can’t talk, can’t kiss, can’t fuck or do much of anything without someone else seeing us before we leave. But Sandy still reaches out and puts something she has hidden in her hand into mine, with that same smirk. It’s that leopard print G-string, still wet with us.
I smile and wave. She starts her car, rips out of the lot a little too fast and is gone. Well, shit. This girl even knows my real name without asking.
I very nearly wrecked my marriage and completely abused the trust of a wife who very much adores me to this day, even being caught and having gone back to Sandy twice before it ended. I am not unaware and certainly not hypocritical of my wife’s reasons for staying with me after, I do know that if the situation had been reversed, I would not have stayed with her, even after only the first time.
I go a week, nothing. I’ve got to let her take this at her own speed, even though I’m very intrigued. Then a text, telling me there’s an open shift that I can work a double on with her. Interesting, that’s my wife’s scheduled day off again. I take that shift. Finish my first shift. I’m waiting. Sandy, in those same leggings, pink top and socks again. She did all this damn well on and with purpose.
But Sandy is not a job. She’s a remarkably uninhibited wildcat of a very real and very present woman who is unknowingly opening trapdoors into a world that is so perfectly right for us both and yet one that she’s throwing one motherfucker of a wrench into.
As I walk out, Miss Arlene pops her head out of her doorway, ten feet from me. She’s freakin 92 years old and still sharp as a tack. I stop by her and she has that wise, all knowing look that only a woman of her age can get. I’ve talked quite a bit with her over the last month or so and she had apparently been a bit of a pistol herself in her day. She pokes me right in my chest with an arthritis ridden finger and stage whispers, “What did you do to that poor girl, young man?” She outright laughs at the look on my face and I have not the first clue what to say. She just says, “I would have given you a run for your money in the old days. I’m going back to bed. Good night, young man.” I chuckle. Yeah, she’s a pistol and probably could have. I say, Miss Arlene? She turned back. I held one finger to my lips and whispered Sssssshhh. She laughed again and I helped tuck her in. She got a kiss on her forehead and I said goodnight. Miss Arlene passed in her sleep about six months later. I wasn’t working there any more by then, but Sandy told me. As far as I know, she never said a word.
Some very good ones, but not like that. Hoooly shit… Mmmmmmm! Sandy playfully shoved away from me using my chest, tossing her hair and bending to take her leggings and top off. She stage whispered “We’re not done yet.” She turns and drapes herself over the washing machine, grabbing the back corners, which lifts her up on tiptoe with her long legs apart. I have a full view of her arched feet, calf muscles, soft inner thighs, wet pussy and asscheeks bunched up as only seen when a woman is either wearing very high heels or is very much ready to be fucked. It’s a very sexy view which speaks volumes into Sandy’s submissive side as well. But what she says surprises me, it’s also the sweetest and most hopeful way I’ve ever been asked. She turns her head, with her eyes closed and says, “Would you fuck my ass?
We’re meant to fuck up or fix our lives as we please.
I’m thrilled that it was how she reacted, she’s instinctively responding to verbal triggers that can take a month’s worth of Neural Linguistic Programming suggestions to instill in other subs I’ve had. I also immediately know I can make her have an orgasm without me or her touching herself, as well as on my command. And Sandy doesn’t have a bunch of little five second orgasms that some women think being multi-orgasmic is. Nor does she have that one full body, fifteen second one and done, either. She’s the lucky rare girl that gets the full body, full minute orgasm and can have 30 of them in an hour. And she’s already came four times in the ten minutes we’ve been in that laundry room.
As much as I’m very much enjoying every bit of this spontaneous experience with all of its discoveries of the rarest type of sexual equal I’ve even come close to, another test of Sandy’s arises.
I can hold her like this for hours. And Goddamn, I want to. It takes Sandy quite a while to come down, to stop her tremors, for her breathing to finally slow, gaining enough consciousness back to realize that she still has my cock inside her. When she does, it makes her shudder against me again and she lets out a long, low moan. I think she can stand on her own, so I move my right hand up, between her breasts and feet her heartbeat. Her breathing pattern falls in synch with mine in that way when you’re both so close to being just one person. My mind is drifting, she’s calming me as much as I am her.
I drive home, hard again, a different view of Sandy. Woke my wife up, had her put her little lace ruffled babydoll socks on, fucked her sexy feet and finally made her spread her legs with her feet in the air while I laid in between her legs and pumped her hard, thoughts of taking Sandy the same way making me spurt deep and hard inside my wife’s tight pussy. After the normal snuggle, we cleaned up, but my cock was coated in cum and my wife’s pussy more messy than normal. My orgasm was a damn strong one that time and I was running out of her, down over her asshole and onto the bedsheets. My wife, asks me what the hell that was all about and I told her that I had been thinking about her wearing those socks all night. She made me promise to give her a chance to come too tomorrow before we went to sleep. Promise kept, the next day. Fantasized about Sandy again too.
If anything, Sandy immediately pulls harder on my cock with her mouth, her hands tighten and she fairly screamed around me for the two more seconds it took for my cum to spurt across her tounge and against the back of her mouth. Her cheeks pull in harder again when she gets the first swallow, but by that time, I’ve jetted two more times and the sheer intensity of my orgasm is making my cock pulse so hard that she can barely keep her lips around me.
That’s Sandy.
It’s been almost ten years. In that two and a half years of sharing, exploring and experiencing every single fantasy I’ve ever had with a woman who never, not once, questioned or hesitated at my desires nor did I ever with hers. We held absolutely nothing back. It’s both perfectly beautiful and horrifyingly ugly what Sandy and I did to each other. I didn’t even get to the really good stuff here. You got the tip of an iceberg. And you know what? I don’t really even want to tell you any more. Not when I still fantasize about her every damn day and her loss left that hell of a hole in me. Putting this to words tore that hole even bigger. I didn’t think it would.
She says, “You let me.” Still crouched she cups of my balls in her hand and wraps her fingers around my shaft with her other hand, before she licks the precum off the head and wraps her lips around it. As she slides her mouth down, she starts to stroke with her hand and squeeze my balls, all at the same time. It briefly crosses my mind that my wife may have told Sandy exactly how to make me cum with her mouth, Sandy has already edged me close twice to exploding in her pussy and then in her ass, I’m about to cum the fastest I’ve ever cum with a woman’s mouth.
While performing together on our couple’s profile we simply were good at acting sexual improv with each other and inventive with ways to fake damn near anything the guys wanted to see. While talented enough to make decent money in our various roles, we stopped after our own enjoyment of each other was being compromised by the job. After all? It’s a job.
I’m not even close to knowing how long I’ll go, this is simply the hardest I’ve ever cum and I’m starting to shake, not unlike she did. Somewhere in there I had double wrapped her hair around my hand and forearm, it was a first for me that not to remember doing it. Sandy is losing her balance again from her efforts and I’m basically stopping the both of us from falling in some weird fluke of physics.
She turns away and has her car door open before she adds, “Hey, Daddy?” I tilt my head questioningly. Sandy just says, “Where the hell have you been?”
Another one of Sandy’s sharp intakes of breath, but instead of freezing in place this time, she arches her back, shifts her weight and slams her hips back on my cock. She took it in so fast it nearly hurt me. And took all eight and a half inches long, big around as an empty paper towel tube deep and wide of it too.
I had a two and a half year affair that had some absolutely amazing encounters. To preface this, I’ve been in the swinging lifestyle since I’ve been 23 years old. I’m now 49. This happened to me outside of the lifestyle, though. As I write, the details may have actually occurred almost ten years ago, but I remember them as if they were the day after. I do like to write, the details go long, but I do hope you enjoy.
Sandy has my balls in both hands, rubbing gently. My cock is waving right in her face, but I realize this is the first time Sandy is seeing it outside of tent pole pants form. I’ve taken her in nothing but from behind so far. It’s completely clean shaven down there, a lifestyle etiquette thing. But I think she likes it when she starts kissing the V between my cock and belly, the shaft of my cock now against the side of her pretty face. My precum smears her cheek, but she doesn’t even flinch.
I shove all the way in at that and pump my cock in and out of her while she’s cumming. Sandy was starting to get louder and I put my hand around her head and over her mouth. She actually screamed then, into my palm, then bit it hard and whimpered for almost the minute it took for her to finish. I was watching the way her pussy gripped my cock as I slammed her, all slick with her juices and was amazed at how well she liked it as hard as I could give it.
My balls hit her wet pussylips and clit kind of deep. And it didn’t stop her from pulling almost entirely off of my cock and slamming her hips back again and again. She just didn’t stop, fucking herself on my cock as hard as I’ve ever fucked another woman’s pussy, but never as hard as another woman’s ass. Sandy flailed, reaching for and catching my forearm and hand on her hip. She pulled my arm right into her mouth and bit the hell out of me, now howling through it as she came. She just didn’t stop. More than a minute solid. Threatening to push me out of her the entire time.
Being fairly popular within lifestyle circles, there have been a somewhat decent amount of play partners ranging from the women young enough to be my daughter to old enough to have been my mother and just about every kink that can be sexually expressed. I’ve very much enjoyed each experience with every woman. Each is, of course, unique in her own ways. Even then, it’s important to understand that the further you can go down the rabbit hole, the harder it may be to have recurring fantasies fulfilled and actually be fully sated. It can lead to deviant sexual desires or performing socially taboo acts.
Sandy and I work, always closely together until the first shift comes in for report. It’s been a quiet night and Sandy is proving to be a wicked smart and very caring woman. Just talking with her calms me in ways I never let go. The only other person who can do that for me is my wife and I already know that I’m in one fucker of a lot of trouble.
It’s definitely not misspoken. Sandy starts shaking again, her orgasm threatens her balance, tipping her forward. She grabs my cock hard, now really in her hair as her face goes tight to my hip. Her hand holding my balls as she sucked them shot in between my legs and grabbed at my ass and lower back. Holding me, she stammers out a breathy, Ooooooh God, Fuuuuuuck.”
As any real Dominant does, those questions and qualities are asked of and expressed to new partners in an initial interview of sorts. Even if she’s a professional Dom or sub. Especially as a mark of my character as Alpha. It’s asked. Because of that spontaneity of the situation, again, I have no way of knowing how Sandy will react. I already fell in both lust first and now love with this most amazing of women. That knowledge alone scares me in a world where I fear very little in life.
I’m weaving on my feet and it’s hard for me to focus. Sandy has her hands to each side of her to keep her balance. I have to catch the edge of the washing machine and Sandy crabs backwards to the wall, leaning up against it. Her ass is out a bit from the wall and she spreads her legs wide, bent at the knees and pulling her feet back towards her. They arch and her toes point. I can only stare in fascination of her as she says, “Watch me.” A mature woman very much makes herself look like a salacious teenager as she runs her hand down her cum covered belly. Her hand slicks up fast, as I saw this I realized that she’s glistening with it from her upper lip to the triangle of her G-string, the top soaked from me and crotch panel from her.
Or the one who can’t take it long enough to jet my cum deep up her ass and still cum with me because she loved the feeling.
My cock slowly slips from her ass, half hard. Even though I know neither of us really like it, the feeling is still intense. She lets out another long low moan and my simultaneous growl tells each other that neither of us really wants to be done yet. She turns around, facing me and wrapped her arms around my neck, her wrists crossed and her fingers in my hair. She’s very pleasantly pulling my head down, while she slides her leg up mine, right below my ass, bending her knee and curving her calf around the back of my thigh.
It’s also one AM, who else is out there? Nothing but an attachment and I click on it. A very nice woman’s ass comes up on screen, a mirror shot from bent over, hands pulling her asscheeks apart so that I can see all of a black and tan leopard print G-string. The triangle of fabric is barely covering her pussylips, the string isn’t covering her asshole at all. I’m trying to figure out who this is. I haven’t been chatting with any lifestyle women and even they aren’t this forward. I really study. I recognize her hands, pulling her perfect asscheeks apart for me. Her longish painted nails and the rings she has on most of her fingers.
While I did not have the ability to leave Sandy in the ways I would have ever wanted for her, I destroyed her in doing so. And a fairly good chunk of myself as well. Neither I can ever take back.
I would only see Sandy during the shift change reports, before heading home to masturbate like crazy, oftentimes sexting with my wife before I could finally go to sleep. It’s almost routine. Sandy was not an obvious choice to think about at first. In her early 50’s, no make up, hair always up, loose jeans and scrub top that hid her body’s shape, she didn’t trip too hard of a trigger for me. There was a chemistry between us though, something that when I have it with certain women, it’s always at the back of my mind. Before long, being on third shift during quiet hours, my wife and Sandy began discussing sex and comparing notes who was sexting what to who. My wife would tell me as a turn on. Always a fun game.
Well, holy shit.
I am holding a woman in absolute heat up by my one hand over her mouth and my other arm wrapped around her hips. She’s shaking like a leaf, actually trying to make herself stop cumming. She’s losing that battle, still perched on my cock, buried up to my balls inside her. I finally pull out of her and gently move her leg down to the floor, turning and holding her to me. We’re still half dressed, in a laundry room and she started to gently cry. I still held her. When I quietly asked her what was wrong, she took my face in both of her hands and said, “Baby, nothing is wrong, everything is just right. I haven’t had sex in the nine years since my divorce. I didn’t want or need it until I saw you. I took a chance on that you would want me. I saw it in your eyes how you needed me. Oooh. I’ve never had orgasms like that.