It had been a few weeks since my boyfriend, Tom, had become the “bull” for Jess and Steve’s cuckold relationship. I had enjoyed watching him fuck her finding it more fun than I ever thought I would. I’ve known Jess for years, but the recent change of our relationship couldn’t be more surprising. Yes, she was an open person, but I had always been reserved around her when talking about sex in order to not cause offence or be rejected.
Her negative response to me telling her I enjoyed anal was probably the main reason for this, so as much as we enjoyed talking about sex it was something I was careful about, making sure to exclude anal group fun, she simply wasn’t as liberal as myself — or so I thought. The Jess I knew was long gone. She’s now obsessed with sex, asking me about everything and anything to do with it. Our Monday afternoon coffee meet-ups had become sex question time. I enjoyed sharing my experiences with her; it gave a great sense of sexual power. Her most recent line of questioning had been all about anal. It was strange talking about it to her; she seemed to have no knowledge of her previous distaste of the subject as she rolled off question after question.
“Does it hurt?”
“Only if you don’t do it right,” I answered calmly. Being asked about anal was something I was simply used to by now, it was as if I had the answers written down on the inside of my eye-lids.
“How do you do it right?”
“You use toys, fingers, lots of lube — you have to get yourself ready for it. You can’t expect to just take it in there straight away you know.”
“Is it worth it?”
“You know I prefer anal, I mean I cum from just having him fully in me, and when he cums! I swear my eyes roll back, it’s heavenly.” My mind drifts off to thinking about our last session. Whenever I speak of anal I’d feel suddenly empty, incomplete, and long for Tom to fill me back there. It was more than a desire, it was a need.
Jess caught the glossy look of lust in my eyes and smiled at me, “I see somebody is going to be requesting a bit of booty loving tonight.”
She broke my daze and I laughed. She was right; I simply had to have him make love to my ass tonight, my body was already tingling in suspense at the thought.
“Maybe I could watch?” she mumbled.
“Watch?” I replied, my lustful cravings making me daring, “No.”
Jess looked hurt.
“But you can join in and help,” I smirked at her.
“Oh I’m not ready to yet,” she answered rather defensively, “I just want to watch you and Tom do it.”
“That’s what I mean, you could help me get ready for him, it’s something he loves watching, two women, you know, being a man and all,” I chuckled.
She smiled at me, her eyes glowing with knowledge that I had let slip the fact it’s something I’ve done before.
“I’d love to. Steve would have to be there though, cheating and a cuckold fantasy are two different things in my books.”
“Of course hun,” I smiled, “Just let me know your limits before hand, nothing ruins a good show faster than someone being uncomfortable and saying no.”
It had been a while since I’d put on a show for Tom, and I was determined to have his cock close to bursting before I even let him inside me. I also thought Jess owed me a few favours, and I had some ideas of how I could cash them in…
We finished our coffee and I pushed my mug away from me. “Right, we have some shopping to do!” I declared. I’d let Jess know what I had planned while we shopped, hoping she wouldn’t say no to too much, my body was already shivering in excitement with ideas. I’m lucky to have such a good selection of sex shops where I live (three of them) and any embarrassment I had about buying such things had long since gone. Jess was new to it though, and seemed like a schoolgirl enjoying the sense of misbehaving. By the time we left our bill was more than excessive and our bags rattled with the sounds of chains.
We went to my place, said hello to Tom, got Steve round, showered, and went upstairs to get ready. I knew what I wanted and was determined to get it done right. Tom and Steve watched a film while we prepared, banished from climbing up the stairs for any reason. I’m sure they didn’t take in a single thing of what they watched as their minds filled with lusty ideas of what was to come.
I had watched Jess bounce around naked on Tom a few dozen times now, and although I had joined in stroking or sucking him Jess had never seen me naked before. She was a slimmer girl than myself. Her breasts and bum looked small compared to my own. Revealing myself to her felt like a big moment, strange considering all that had happened, and as we looked at each other, holding our towels around us I asked rather seriously, “Ready?”
I think we both knew this was going to be one of those moments, where a new boundary would be crossed, as Jess became more and more a part of mine and Tom’s sex life. Jess nodded, and we let the towels drop to the floor. I see her eyes fix onto my large breasts, “They’re beautiful Goey,” she mummers, here eyes still on them. I thank her and we move close together, my bosom pressing against her own, and I kiss her — she doesn’t resist.
“What was that for?” she asks as I remove my lips from hers.
“Simple,” I said, “Men enjoy watching girls kiss, that was the easiest way of knowing if your comfortable with it.” We kiss again, this time her tongue is more adventurous against my own.
I don’t ask, I simply say, “Now my breasts.” Jess crouches slightly and lifts my boobs with her hands, feeling the weight. She has always been a bit jealous of the attention my DDs have got over her own Cs (as pretty and perky as they might be) but the chance to feel them seems to have been a long held desire of hers as her previous hesitations vanish and she hungrily sucks each of my nipples in turn deep into her mouth.
She moves her head back and looks at my chest as they overflow her hands.
“Do you like having big breasts?” she asks, already knowing I do.
“I’d be lying if I said I didn’t” I smile.
Jess gives my pierced left nipple a hard tweak, “And what about this?”
“So why not have both done?” she questions as the palm of her hands support them, her fingers and thumb pinching each of my nipples.
“Two different sensations this way,” I wink at her.
We tumble onto the bed and play with each other’s breasts, tweaking, nibbling and exploring one another giggling away like girls who share a naughty secret.
“Now it’s time for the most important test”
“I said I’d do it in the shop, don’t worry about it!” answered Jess playfully.
I got on all 4s, “Come on then, lick my ass.” Just saying it makes my desire immeasurable.
She moves behind me and parted my cheeks.
“My god Goey, it’s tiny!” exclaims Jess as she looks down at my asshole, her hands trembling slightly with nerves as she holds my cheeks apart. “How on earth does he get it in there?” she asks in disbelief.
“You’ll find out soon enough,” I say rather irritably, “Now just lick it already!” My whole body aches; I simply need her to lick my ass, if she backs out now I’d feel terribly rejected. I feel her lean forward, her breath running across my skin as I shivered in anticipation of her tongue, the wait seemed like forever but then, finally, her wet tongue glides across me, my body tensing and then sinking into the bed in utter bliss, as I let out a deep moan of pleasure.
“Oh wow,” sighs Jess lustfully, “That didn’t taste bad at all, really nice actually.” Before I can speak any words of hurt towards her expecting me not to taste nice she probes my ass with her tongue. “Oh Goey! You taste really good!” comes Jess’s delighted voice from between my cheeks. She was losing herself in the moment, her tongue hungrily darting in and out of my ass I moaned blissfully. Suddenly her face left my ass and I felt her fingers tap against my pussy lips. “Wow, you really like this don’t you?” she asked while pushing her fingers slowly into me, “I mean Christ… you’re so wet!” My body heaves with pleasure as she pushes her fingers deep into me.
“Okay” I said breathlessly, “That’s enough, save the rest for the show.”
Her fingers slide out of me, and she sucks my juices off them without hesitation.
“I was going to ask you to use that for lube…” I say jokingly offended.
“Sorry” she laughs, and spits onto her fingers, and circles her pointing finger around my puckered hole, “Just tell me what to do, we’ll have your bum ready for some back door loving in no time!”
“Not yet” I smile, “We want the lads to watch.” I sit up and we huddle close, like kids plotting of grand future plans. I go through my plan with her. What each of us will be doing, when to use what and what to do if something doesn’t go to plan. She listens closely, both of us losing ourselves in excitement as I build the scenario up.
“You ready?” I ask
“Yeah” she nods
“Okay” I say while sitting up. I reach into the bag and pull out the neck and wrist restraint (known as a half-hog) as she lifts her head, exposing her throat. I fasten the collar around her; a strap laced with D-rings rests down her back. I buckle her wrist restraints on next, for now nothing more than leather bracelets with an unused swivel clip, they’ll be attached to the D-rings later, but for now I want her hands freely movable. She pulls her latex spanking skirt out of the bag and wiggles into it while I buckle my own newly brought collar around my neck. With some help I squeeze into some latex stockings and we both pop on some ridiculously high heels. There are a few other new items in the bag, but for now they can stay where they are. We kneel on the bed facing each other, our breasts heaving against one another’s as we cup the other’s butt.
“You can come up now boys!” I call, and then we kiss lustfully as we hear them march up the stairs.
They sit on the small sofa facing the bed as we kiss, our hands gliding over each other’s skin as we accentuate every curve and motion. I hear Steve gasp as we part our bodies and my heavy breasts bounce freely from the support being pressed against Jess offered. Jess worships my breasts as I had told her too, lifting them to rub her face against them and gently licking and sucking my nipples, causing them point out harshly. I turn and bend over, lowering my front and lifting my bum high into the air. Jess spread my cheeks and begins licking, I hear the men sigh in lust as she uses the full width of her tongue to wet my asshole. She starts pushing her tongue into my ass and I moan in pleasure as I feel it part my hole. Her fingers start to run over my clit; already my wetness is soaking her hand.
“Goey you’re so wet, and your ass is so tight! Why don’t we show the boys how tight you are?” smiles Jess, playing the part perfectly, she looks back at the men and spreads my cheeks giving them a clear view of my wet asshole before flicking it with her tongue, making sure they can see the action. She lubes her finger with the juices from my dripping wet pussy and circles it around my asshole, letting me feel the silky warmth of her finger against every crinkle of my puckered hole, before slowly pushing it in, making my ass look impossibly tight as it disappears into me.
She slowly fucks my ass with her finger while circling her other hand around my clit; I bite my lip as I try to hold back my orgasm, I didn’t want to cum yet, it was too soon, but Jess’s hands and the thought of being watched was tipping me over the edge. I tried to tell her I was going to squirt, tried to warn her so she wouldn’t be shocked but all I could do was gasp as orgasm took me.
“Oh my god Goey you’re spraying on my hand!” I hear Jess cry out, in what I at first think is horror, and then realise is amazement. Her finger slides out of my ass as she removes her hand from my clit and she slides two fingers into my pussy, fucking me ferociously with them, I whimper as I feel myself failing to hold back, I scream out as I fully climax, Steve and Tom sit with their mouths hanging open in amazement, as I gush all over Jess’s face.
I pant deeply as my body gradually floats down from my orgasm, attempting to apologise for squirting but before I can Jess’s hand whips down onto my right cheek and I jump in surprise as the stinging heat spreads.
“Oh Goey you nasty piece of sex you!” squeals Jess, completely overcome by lust as she plunges two fingers deep into my ass, her hand banging against me repeatedly as she plunges in and out.
“I think it’s time to get your ass ready Goey, really ready!” Jess shouts excitedly, still fingering my ass while rummaging in the bag of new sex toys she pulls out the buttplug. I have a lot of buttplugs, ranging from the width of a finger to a pint glass, but this one was different — it was inflatable. A long tube ran from its base to a small hand pump, Jess gives it a quick naughty pump and watches it enlarge a fraction, “This is going to be so much fun!” she exclaims while splattering it with lube. I spread my cheeks, the cool air tingling against my hot moist asshole, and she pushes it in easily, my ass sucking it in as it pops into me, my asshole tightens around the neck as the base rests against my cheeks.
Jess holds up the pump end and looks at the boys, “Steve, this is for you.”
Steve stands up and slowly approaches, as if caught in some kind of fantastic dream, and gingerly takes the pump from Jess. She pulls his head down and kisses him passionately, “You be good to her ok? We want her spread wide, not ripped open.”
Me and Jess roll onto our backs, our knees up and our heads dangling off the side of the bed. We turn to each other and smile, and just as planned and in perfect union we look into Tom’s eyes and ask, as if a daughter asking her father for a present, “Please Tom, please, fuck our faces!” It’s cheesy and a bad porno cliché but it works. As his clothes hit the floor it’s easy to see his cock is larger than usual and I smile knowing we can make it bigger yet.
I open my mouth and close my eyes as he lowers his cock towards me; I take it down my throat effortlessly feeling his size fill me as his balls rest on my face. Jess’s eyes widen as my throat bulges with his cock. He pulls out and points his cock at Jess’s face, she opens wide but I can see the worry on her face — she’d never managed to deepthroat him before. He slowly pushes himself into her mouth; I can feel the bed shake as Steve begins to wank, slowly squeezing the pump, enlarging the buttplug inside of me, as the excitement of watching his wife begin to gag entrances him. Jess splutters after about taking half of Tom’s immense shaft and he pulls out, rubbing his cock over her face as she pants.
He begins alternating between us, plunging his cock into my throat a few times before shallowly fucking Jess’s mouth. I feel my ass stretching, getting more and more full, as Steve pumps air into me. As the buttplug reaches its full size I motion to Jess to get up. We kneel on the bed facing each other, our eyes teary with spit hanging from out fucked mouths, and kiss wildly. Jess’s fingers sink into my wetness as we kiss, her tongue deep in my mouth muffling my moans. As the kiss comes to an end, I fasten Jess’s wrist restraints to the strap on her back, fixing her arms behind her. I reach into the bag and pull out a metal o-ring gag, designed to keep the mouth open. I lift myself higher on my knees to fasten it around her; my breasts gently rub across her face, and pop the o-ring in. She struggles to open her mouth wide enough for it, but any smaller and what I had planned would simply be impossible.
I leave Jess kneeling on the bed, unable to close her mouth or use her hands, and pull out a large metal bar from the bag, with 4 clamps on it — 2 for my wrists, 2 for my legs. I lay it across the bed and position my self onto it, my arms between my legs as I lift my ass into the air. Tom fastens me in easily. I motion for Jess to get behind me, so she can see my ass easily; she walks on her knees, doing well to keep her balance and positions herself in view of my plugged asshole. Tom fastens a ball gag around my head, pops the ball in my mouth, and kneels behind me, spreading my cheeks.
He mutters something to Steve, who slowly pulls the plug out of me. As the plug fully exits my ass I feel the cold air against it. It feels like my gape is huge, easily as wide as a can of Red Bull, as Tom hold my cheeks in place. He speaks to Steve again under his breath, I’m unable to hear what he’s saying, but soon know, as Steve pushes two lubed fingers into my ass. My gape is so large his fingers barely touch the walls as his hand comes to rest against me. He gently fucks me with his fingers, removing them every now and again to apply more lube.
As Tom lifts himself up to fuck my ass, Steve withdraws his fingers. Still spreading my cheeks wide apart I feel the large head of Tom’s cock rest against my gaping asshole, wet with precum, he moves his hands away as he pushes it in. It slides in without resistance, and then as it reaches past the deepness of the plug I begin to violently orgasm. I bite down and scream at the ball gag in my mouth, as my own wetness soaks the insides of my legs, my body convulses, thrashing against the bar restraint, as he sinks his entire length into me. I hear Steve panting deeply and Jess attempting to say “Oh my God” as the o-ring restrains her mouth.
My ass feels amazingly full and stretched; the sensation of his cock buried deep inside me causes my heart to flutter as my orgasm settles. Tom withdraws his dick from my anus and the sudden longing to be filled overtakes me, my eyes water slightly with frustration as my heart pleads for him to use my asshole. Steve moves behind Jess and holds her head in place as Tom faces her. This would be the moment that I really needed Jess to do well. Tom was going to fuck her throat, and roughly. I’d made her be sick before we came back but I was still worried. Steve kissed his wife on the cheek and Tom began to slowly push his dick into her gaping mouth. Her eyes darted around with worry and then screwed tightly shut as she began to gag. Steve stroked her hair as her body lurched forward, her gag reflex rejecting Tom’s size. But the human throat cannot gag forever, and I heard Tom sigh in relief as his length filled her. Her throat bulged with his manhood as she spluttered, long strands of spit hung from her chin as Tom began to slowly fuck her throat, her eyes watering as he dominated her face. She gags, splutters and heaves but Steve holds her head in place.
Jess pants deeply as Tom withdraws from her mouth. He slides his cock deep into my ass and begins to slowly fuck me. I loose count of my orgasms as each stroke of his long rod sets me off repeatedly. My eyes water as my body quivers with the overload of pleasure my well-fucked ass is giving me. He holds my cheeks apart as he slowly withdraws his length. My gape is huge. As Tom spreads my ass Steve pushes Jess’s head down to my wrecked hole, her tongue darts out, tasting my tender passage before plunging in fully. Her tongue spreads wide in my ass, it’s hot wetness causing my body to tinkle as it strokes the inside of my tender hole.
Steve moves Jess away from me. I watch as Tom sits back, his erection pointing proudly in the air, as Steve positions Jess’s mouth over him. Steve pushes her onto her front; unable to support herself she collapses onto Tom’s cock as Steve enters her from behind. She dry heaves as her throat is filled, the gagging sensations of her throat only causing Tom’s cock to thicken further. Steve lifts her head up allowing her to catch her breath every now and again as he fucks her from behind. Each time seems longer apart and I begin to worry she might pass out. Thankfully Steve soon cums, pulling her head back harshly as he unloads inside her. They discard her, pushing her onto her side as she pants for air, Steve’s cum trickling out from her pussy.