[Threesomes] The Dare

[d7uncan]

Chapter One
It was all about bar food and WiFi. My usual hotel for these business trips was sold out, and the alternative hotel had one of the worst Internet connections ever. I ended up across the street at a bar that not only had the connection that I needed to stream HBO but, happily, also served excellent Buffalo wings. With my attention on the food and the laptop, I didn’t notice as the place filled up. Apparently, this place was also well-known for its selection of fine tequila and I had wandered in on Two-for-One Tuesday. I had pulled out my earbuds while waiting for a new episode to load and a voice behind me said “What? Season three of “Silicon Valley” is out? How the fuck did I miss that?” Without thinking, I blurted out “Too many two-for-one Patron shots, maybe?” and turned to see the speaker. As soon as I saw her, I expected to get shut down. She was way too young and cute to be interested in an average-looking white guy in his 50’s, let alone one watching a video alone in a crowded bar. She said “No, that’s not it; more like the 16-hour days working on the project that I signed off on today.” “Ah, that would explain the two empty glasses in front of you and the two full ones in your hands” I replied and began to replace my earbuds. To my surprise, she spoke again “Oh, the rest of these weren’t for me. I got them for my so-called friends who are now nowhere in sight. I’m already drunker than I wanted to be, I’m tired of this noise and my feet hurt.” Maybe I was mistaken; maybe I missed something on the first impression; at any rate, she had not yet told me to go back to the nursing home and fuck myself. Nope, first impression was correct: cute young thing, vaguely ethnic (Pakastani? Middle-Eastern?), slim with prominent breasts proudly on display in a form-fitting black dress. The cause of the aching feet? Not the stilettos that I would have guessed but high-heeled boots wrapping her calves in tight black leather and straps. Sure, she wore glasses but as tons of Japanese anime proves, glasses can be an asset for the right audience. No wedding ring… What the fuck, I thought, she started the conversation, I guess I have nothing to lose.
“So, I’m guessing that tomorrow evening will be you and your boyfriend binge-watching Season Three?” I said. “You’re half-right” she replied, “I’ll be bingeing. He’s in Miami for another week. In fact, he’s probably burning through the new episodes right now in his hotel room. What about you – what’ll you be doing tomorrow night with no more episodes to watch?” In the spirit of what-the-fuck, I told the truth for once instead of the cover story I usually use. “I have a room reserved at a clothing-optional motel and I expect to be swimming and hot-tubbing naked with a crowd of friendly strangers.” “Bullshit!” she retorted, “If you said hot-springs I might have believed you, but I’ve never heard about a motel with that sort of setup, and I know a thing or two about the alternative scene.” I looked at those boots once again in light of this little nugget of info and plunged ahead: “OK, here’s the deal: I can prove that this isn’t bullshit and I’m calling you out. Here’s the dare: Give me your phone number and I’ll text you the address so you can follow me to this motel in your car right now, tonight. If I’m lying, you will have the satisfaction of putting me in my place. If I’m not lying (and they have an available room for tonight), you will go with me to the pool, no other strings attached. You don’t have to take any clothes off or do anything else, just join me as a spectator in the clothing-optional area.”
“Don’t go away – oh, and I’m Kat, by the way” was her response and she turned away, taking out her phone. Several minutes later, she surprised me by turning back around. “All right, big talker, you’re on the hook. Just so you know, my boyfriend and several other friends now have your picture and the address and are expecting me to touch base. You are going to learn not to lay down a challenge with me unless you’re ready to follow it through.” An hour later, we were closing the door to the motel room after taking a stroll through the pool area completely clothed. Unlike the hot-springs and nude beaches, Kat had been treated to the sight of one couple obviously fucking in the pool and a group of middle-aged swingers languorously kissing and stroking each other while perched on the edge of one of the Jacuzzi’s. I had pointed out to her that there were a small number of single guys scattered about, enjoying the show and keeping a respectful distance unless clearly invited to join in. “I gotta hand it to you,” I declared as the door latched behind us, “Lots of women like to boast about how open-minded they are until they have to prove it. You’re the real deal and my hat is off to you. You kept your part of the bargain; shall I walk you to your car now?” I still saw her as this sweet young thing, a lot more innocent than she thought she was and probably ready to scamper home and play her leather-fetish games with her boyfriend via Skype while telling the story of her big adventure.
Imagine my surprise then when she instead grasped the hem of her dress and pulled it over her head, revealing the lacy black bra cradling those generous breasts, the matching lace thong panties and, joy of joys, the satin retro-style garter belt attached to black stockings. Grinning widely at the obvious surprise on my face, she said simply “I dress like this all the time because I like having a little secret identity. I thought this place would be gross and sad and instead, I feel like I’ve always belonged here. Finally, I’m in a place where my secret self fits in.” I had just enough presence of mind to say “So, are you saying that you want to go back to the pool and let everyone see the real you?” She considered this for a moment and for the first time, I saw anxiety play across her face. Haltingly, she finally said “I liked the way you took charge of the situation and challenged me to take a risk. I want to feel more of that.” It was as if a cool breeze swept across me at that moment and I understood what this was going to be about. I had tossed my backpack into the room when we first arrived, the one with my trusty toys and accessories. In airport security, I always wondered what went through the minds of the TSA agents when they saw the thick leather dog collar and the G-spot vibrator on their X-rays. Kat gasped when I pulled out the collar but did not resist when I took hold of both shoulders and urged her to kneel. I fastened the plain leather collar around her neck and told her “Your safe word is ‘purple’. Use that word if you need me to stop. Otherwise, you are going to follow my lead at all times. I am going to ask you questions from time to time. Answer with the truth, not what you think I want you to say or with some pornstar dialogue you and your boyfriend have seen on Reddit.”
Kat looked up at me, her wide eyes a deep translucent brown. Her voice was throaty as she said “I understand. Purple. I love the way this feels around my neck. You own me until the collar comes off.” and I watched a shiver go through her as she uttered the words. “Good girl.” I murmured as I slipped two fingers under the collar from behind and pulled her gently but firmly first to her feet and then backwards until her calves hit the bed. “Your new friends are going to see you and wonder what happened between our little walk-through and our reappearance. You can keep it a secret, but maybe you won’t want to.” Clipping a thick leather leash to the collar, I used that to pull her backwards again. She half-fell onto the mattress beside me. With “you own me” replaying in my mind, I pushed her over onto her hands and knees. Kneeling behind her, I pushed her knees farther apart and cupped her lace-covered vulva in my hand. She didn’t protest but seemed confused about the lack of preliminaries, her motions tentative. My left hand pushed down on the small of her back (that perfect, smooth brown landscape of muscle and bone), my right hand pulled her up literally by the crotch. She seemed to melt, relaxing into that pose: the young nervous b*tch committing to being mounted. Christ, it was like turning on a valve. Within seconds I felt her panties sliding around in the grool that dripped from her. It was easy to slide the fabric to one side and slip two fingers between the lips. I did not have to reach inside and search for the slippery evidence of her arousal; it was a swamp inside and out, every fold saturated with steamy juice. I took advantage of that lubrication and slowly, inexorably pushed. There was a short gasp as she felt the invasion and then that air all came out in a moan of acknowledgement as I opened her up at my speed, sooner than she expected and none of the considerate little-more-at-a-time routine that her past lovers had used. Before that moan ended, I was palm-deep in her tight pussy with her cervix heavy against the pads of my two fingers and powerful internal muscles twitching against my knuckles.
Instead of pulling out and thrusting back in, as her hips begged me to do, I bounced her cervix and uterus with those buried fingers and was rewarded with another gasp and wonderfully, another generous flood of that hot slippery vaginal drool. Slowly now, I pulled my fingers out until they rested against her entrance. It was like her hips, her pussy were talking to me, grinding back, asking for that penetration again. I teased her for a full minute, only letting her feel the tips of those two fingers. I added a fingertip, pulled the leash tight over her back and stretched her back over those three fingers just as slowly and relentlessly. No sound this time; she caught and held her breath and arched her back. This time, I did not have to move my fingertips inside; her cervix…no, actually, her entire small firm uterus spasmed up into my fingers. “God - Fuck - God - Oh” burst out of her mouth in time with those spasms. “I’m close, Jesus, so soon.”
I smiled and slowly pulled my fingers all the way out. Her pussy chased my hand, unfulfilled, on the verge. I pushed her over onto her back and then used the leash and a hand on her shoulder to pull her into a sitting position on the edge of the bed. “This is how I want those people to see you. The smart ones will see the signs and know that you’re only halfway there. They are all going to want to be with us when I take you the rest of the way. You can try to keep it a secret or you spill your guts about what an obedient little sl*t you have been and want to be. Remember your safe word and be aware that you get to pull the plug if you need to. Until and unless I hear that safe word, I am going to turn you and your world inside out." As I spoke, I watched the initial frustration in her eyes drain away and be replaced by the hooded internal gaze of arousal and discovery. I quickly slipped out of my clothes and wrapped a towel around my waist. I wrapped a towel around her for the walk back to the common area but left all her lingerie and boots as they were, even the soaked panties. I was going to enjoy sharing that outfit and its removal with the couples and single men at the pool.
Chapter Two As soon as we were through the door to the common play area, I pulled the towel off of Kat and led her by the leash to two empty chairs at the far end of the pool. The eyes of all the single guys and most of the couples followed us. I stood behind her, just enough tension on the leash to pull her chin up and arch her back. “See how they look at you” I murmured in her ear, “They all want you and know that you are mine to give or refuse. They wondered who we were before, now they know. They know that you are my dirty little sl*t. They like seeing you in your fuck-me black underwear and high-heel boots and think that I chose them; only I know that the story is even better, that you chose these yourself and then went looking for a real man who would make you live up to them.” Holding the pressure on the leash with my right hand, I reached down and unsnapped the bra with my left and slipped the straps off of her shoulders and down her arms. Beautiful – natural tits, big brown nipples already standing up. I reached under her arms with both hands and cupped them, then grasped both nipples and pinched, just a little. Her knees buckled slightly and I filed that away. I could probably make her cum that way alone, but not yet.
I hitched a finger inside the waistband of the sheer black lace panties and pulled them down her legs until they puddled on the tile floor. Reaching around again, I nudged her thighs apart. She stepped one booted foot out of her crumpled panties and leaned back against me for balance. Her mound and labia were, impossibly, even wetter and slicker than before. To reveal this to our audience, I slid two fingers deep into her and then out, bringing them up to her face and painting her lips and cheeks with her juices. Two, three times more until her lower face gleamed wet in the dim light. “They know how aroused you are, what wearing this collar does to you” I whispered. She melted against me, her ass grinding back against my towel-covered cock. “Open your eyes. Look at them. This is not some role-play fantasy with your boyfriend. You’re my sl*t and you’ll fuck everyone here if I tell you to. I don’t care what you think you can take, little girl; you’re going to find out what it’s like when the grown-ups play.” I had three fingers buried in her pussy at this point and pinched one nipple hard, harder. Her knees buckled again which only served to drive my fingers deeper into her. “Please” she moaned, “Please, more… I’m close again.” “Oh yeah, little girl, it’s time for all of these strangers to see you open and helpless,” I said, no longer whispering. “Keep your eyes open, let them know that you see them.”
All the seats near us had filled up, guys with their cocks in their hands, couples and groups touching in various ways and levels of energy. I settled into a strong steady rhythm, driving those three fingers into her c*nt, the knuckle of my thumb bouncing over clit. “Cum for them, you little sl*t. No secrets anymore. Give it to them. Give me your cum, give it up. Let it out, scream it out.” Her voice rose, strangled, staccato as my hand pounded her “Jesus, yes...don’t stop…oh, oh, ohhhhhhh SHIT OH GOD!” and she bucked against me. For a moment I struggled for balance then widened my stance and gripped her tight as her pussy clamped down on my fingers over and over. My leg muscles were burning but I held on and supported her rag-doll body just long enough to confirm where her eyes had been drawn while being finger-fucked to orgasm. It was the single guys, especially the well-hung ones. Luckily, I recognized one of them, a guy named Richie who sometimes played as a single and sometimes brought his girlfriend. I caught his eye as I steadied Kat on her feet and steered her to the big bed across from the hot tubs.
“Hey, Richie,” I said, “This sweet little newbie was stealing looks at your junk while she was discovering her inner sl*t. Why don’t you join us.” Richie knew the drill; like I would in his position, he waited a second for Kat to blurt out a safe word. Hearing none, he gathered up his towel and other stuff and climbed onto the bed. “There is no sexier sound than a woman being fucked while she has another dick in her mouth.” I said and I saw Kat’s eyes widen. I knew this was a first for her and reveled in the thought. Richie smiled knowingly and lay down across the head of the bed. I pushed Kat down on her hands and knees perpendicular to his body and, grabbing a handful of her thick brown hair, I guided her mouth to his hard uncircumcised cock. He’s a little longer than average and really thick. I loved picturing Kat’s mouth and throat stretching, struggling to accommodate him and I knew an interesting little surprise. Richie is one of those men who gets hard and then, somehow, gets noticeably bigger as he approaches orgasm. Already I could feel the hesitancy as Kat looked at his girth up close and as I urged her down, her lips stripping his foreskin back and her tongue registering the taste of the clear pre-cum oozing from the slit. “Oh no you don’t,” I whispered in her ear, “I know that you were watching all the biggest dicks in front of you when you were showing off like a little wh*r*. You’re gonna learn how to follow through and take that meat, not just tease and then run away.”
Just like in the hotel room, I felt that surrender flow through her muscles and I was no longer having to push her down. She adjusted her jaw, squared her shoulders and sank her face down over his cock, finally stopping with more than half of him in her mouth and gagging slightly as I resumed my pressure on the back of her head to keep her there. “That’s my dirty girl. My little cocksucker. Don’t let this dick out of your mouth until I tell you.” All she could do was gurgle in response. I kneeled up behind her and Richie took over controlling her head, tangling his fingers in her hair and slowly thrusting into her mouth. I tore a condom open with my teeth and stretched it over my erection, wishing that I knew her well enough to fuck bareback but abiding by one of the standard swinger’s rules: safe sex for intercourse, even if your playmates have started with unprotected oral.
I stretched Kat’s ass cheeks open and stared at that drooling smooth pussy one more time as I slid the head of my cock down, across the rosebud of her asshole and then down a bit further to nestle between those hungry lips. She continued to grind up and back and the head slipped easily in. “Richie,” I said “This young thing talks a good game and earned my respect by coming to check this place out, but I don’t think that she’s had more than 3 or 4 dicks inside of this pussy in her whole life. Let’s find out how far this wannabe can fall. Even though she had half of my hand buried in that sn*tch a few minutes ago, I think she’s gonna be as tight as a late-blooming church girl. These young ones snap back so fast…” I spit on my fingers and smeared it all over the shaft of my cock, then pushed slowly and steadily with my hips. Fuck, it was as good as I expected. She had tightened back up and I felt the ring of her vaginal entrance resist and then slip down over the glans. I continued to feel that ring of muscle slip down my shaft as the head of my cock registered every bump, every ridge, every structure that had to stretch or shift to get out of the way of my invading organ. Again, I wanted her to feel owned, claimed, so I pushed in steadily without a break, trusting the copious girl-cum she had produced and my extra saliva to make it possible. As I got about two-thirds of the way in, she started making a muffled squealing sound but did not try to withdraw her hips. She kept Richie’s cock in her mouth as instructed, even though he was no longer holding her head or controlling what she did.
It felt like forever but it was probably only 20 seconds or so until I was buried to the balls in her tightness. I held myself there and felt her start to rock her hips and I pictured what that did inside, the head of my cock stirring her cervix, uterus and other structures from a spot deeper than my fingers could reach. I took up this rhythm and magnified it, grasping both well-padded hips and pulling her back even tighter on my dick. She was now grunting through her nose, her lips tightly sealed and sliding up and down Richie’s erection, “Mmmmf! Mmmmf! Mmmmf!” It was almost too easy, putting together the sexual tells that she had shown me. One little lesson for her in advanced cocksucking and then I was going to feel what it was like to have that exquisitely tight sn*tch spasm around my cock as she came again.
I crouched down beside her so I could see her mouth stretched around Richie’s penis. “Kat, you’ve made a good start and now you’re going to learn something new. You’re going to learn that your gag reflex is nothing to be afraid of and can be managed. In fact, I’m going to love feeling all those pussy muscles spasm extra hard around me when you gag on Richie. You know you can pull up and say “Purple” if you need to. I know that you won’t need to. You were born to suck cock and you are going to surprise yourself. First, take a deep breath” Her eyes opened for a moment and met mine as she raggedly inhaled through dilated nostrils, then she closed her eyes and pushed her mouth down over his thick shaft to the point where he was filling her mouth. “Good,” I coached, “Now drop your jaw and let it gag you a little. That’s it, slow, slow, now just hold it there. That’s going to pass.” She was gagging slightly every couple of seconds but letting Richie sink deeper between each spasm. “That’s right. You’re going to feel a lot of saliva form; let it drip out and down his cock. That is so sexy and it will help. Oh, that’s my sweet little cocksucker, you know you want to get face-fucked, give in, let everything up here relax and let yourself be used.” I could barely control my voice; every time she gagged, it felt like she was grabbing my cock with a fist. I stayed buried as deep inside as I could in that position, my cheek resting on Richie’s thigh and my lips beside her ear. I was sure that she was too deep to breathe at this point, so I said “OK, take it out of your mouth now and catch your breath. Jack him off with all that spit while you re-group.”
She took several long ragged breaths, the tears running down her cheeks, chin covered with thick saliva. Her eyes stayed fixed hungrily on the thick root in front of her and I felt a sense of triumph when, before I could tell her to do it, she bent back down and stretched her lips over his cock again. It was like I could hear my voice in her head as I watched her repeat the same steps without being prompted, fighting through the gag point as she hit that tight spot and then, despite the spasms of her abdomen, adjusted the geometry of her head and throat and slipped him deeper into her mouth. I saw her hit the end of the shiny wet-dry junction marking the limit of her first attempt, pause while one more gag rippled up her body and then she shifted again and a full inch of thick meat slid past her lips. “Oh, sweet one, you are so special,” I said, loud enough for Richie to hear as well, “He’s all the way into your throat now, only a matter of time and practice until you will be plastering you nose up against the belly of every guy you blow and get that ultimate reward of cum shooting straight down into your fucking stomach.”
She backed off again just enough to breathe, keeping the head inside her mouth as instructed. Richie said “I think it’s time to see what she sounds like when she cums properly, not just getting fingerbanged like some high schooler in her parent’s basement. No matter what happens, do not take my cock out of your mouth. Do you hear me?” Kat gurgled “Mm-hm” as he tangled his fingers in her thick heavy hair again. I kneeled up behind Kat and began to stroke full length into her, steady, relentless. Her ragged breathing picked up this rhythm, moans when she was moving air, muffled wet grunts when Richie urged her to take him into her stretched throat. She got louder and more explosive as I shortened the stroke and started pounding her, my balls slapping against her clit each time. She was making noise continuously now and I reached around her with one hand and, capturing a nipple, I grasped its entire length between my thumb and forefinger. I squeezed as hard as I could, merciless. As I knew she would, Kat screamed loudly around the cock in her mouth, a strangled, animal sound, and I felt every muscle in her body go rigid. Both Richie and I stopped moving, savoring the physical sensation of her c*nt and her throat locked around our dicks and, even better, the knowledge that she had given herself to us completely, that we had given her the mind-fuck that she secretly craved. Together we had discovered enough of her secrets already to completely strip away all of her defenses.
A sensible caring lover would have allowed Kat to recover, catch her breath, put her scattered brain back together, maybe even allow her to curl up and fall asleep. Fuck that, this was about showing her what she was capable of. As soon as she stopped jerking like a gaffed fish, I said “Hang on, little sl*t, time for you to give up the rest.” Richie and I supported her limp body and moved her in a shared, hammering pace that echoed off of the tile walls. No protest, no safe word, and I felt the animation return to her limbs. She started squealing again and I knew that she couldn’t believe that her body could snap back so quickly, climbing back up before ever reaching that plateau of drowsy fulfillment. “Again, you horny little sl*t? Now you know, you are insatiable, you have no fucking limits. You’re mine and I could keep you in this condition all night.” I reached up and felt her mouth with my fingers, felt her throat as she struggled to take Richie’s cock pistoning into her face. I could feel that he had grown bigger during the last few minutes and was amazed that Kat had managed to adjust and keep taking him without backing off.
Richie shouted “Fuck! Fuck! Take it” and locked his hips. I felt her cheeks balloon and she made a choking, grunting noise as his load of sperm dumped into her mouth. I felt her swallow and re-extend her neck, twice, three times. That was the final straw for me, knowing that she had taken the thickest cock she had ever seen deeper than any cock had ever been in her throat and then eagerly swallowed every drop of his cum without a moment’s hesitation. Knowing that, soon, someone’s cock was going to be lodged so deep in her face at the moment of orgasm that the swallowing process would be moot. I felt the tide rise inside of me and just had time to reach under her and cup her mound as the cum jolted up my urethra. I felt her swollen clit bulging between my fingers and I felt the underside of my cock pump, pump, pump as the semen flew out of me and deep into that exquisite tight pouch between her firm little cervix and the back wall of her pussy. I don’t know if she was still having orgasmic aftershocks or if she was doing it on purpose, but I could feel her muscles clamp down every few seconds, making me shiver as she milked me, triggering a series of decreasing spasms as I expelled left-over gobs of cum into the condom wedged deep into her. TO BE CONTINUED IN CHAPTER 2 AT A LATER DATE…

[d7uncan]

Wrote this fiction story for a user of Reddit and posted it there first. I drew pretty heavily from my true-life experiences in the swinger community. For those who care, I never really picked up someone in a bar and took them to a sex club. I did have a friend-with-benefits that I first met at a sex club after she accepted a dare to go hot-tubbing nude with a guy she met online. She didn't do anything sexual during that first encounter (with me or with her online date) but she and I did a lot of adventurous things on subsequent nights in a couple of swinger-friendly spots in our city. I would love to hear from others interested in the lifestyle in all its variations.