Go buy the supplies

So you go and exit the apartment again, now they've switched places, Sid licking Alyssa's asshole. She moans much louder than him, incredibly turned on from what she's been doing this morning.

Once you get to the shop Sid mentioned, you get a message from Alyssa, it´s the list of things for you to buy. The list is long, containing some books on Tantra, a Tantric massage table, various cock rings, a tub of massage oil that the clerk said is safe for "all orifices".

Alyssa sends another message: "Please hurry babe, Sid says I can´t cum until you get back. I'm dying, he's teasing me soooo much...."

You try and hurry for your fiancée, and continue down the list. A waterproof sheet for the bed, a small sofa curved in such a way to make....sex....easier. It's made in such a way that the woman could slide her body down on the man, although it's conducive to many, many positions. The list continues with a bunch of....anal....things, butt plugs, beads, that sort of thing....

and the final piece....

....a chastity cage.

Sid can't possibly have bought this for himself, this HAS to be for you....the size alone speaks volumes, his cock would never fit in this. What the fuck....

Another message from Alyssa, with it comes a picture of Sid between her legs, his done splayed flat on her beautiful bare, shaven pussy, a sly smile on his face: "My pussy feels like it's on fire, please let me cum baby, hurry.....".

The clerk sees you holding the chastity cage, it's a small thing, made of clear plastic. The end has a slit for the cock hole to piss and cum out of, and it locks around the cock and balls.

Clerk: "Ahh, this is our best model, allows the cuck to be locked for months at at time without being let out.....you the bull or the cuck?"

You: "...huh?"

Clerk: "You the one fucking the girl or not? I assume if you're buying a chastity cage, you're in such a relationship...."

You: "oh....she's a virgin...just learning how to be more....sexual with another, more experienced guy....he sent me to buy these....things...."

Clerk: "hahaha....alright bud, I don't mind if you want to keep the roleplay up in here....I guess it's more fun that way....right?"

You: "Roleplay?"

Clerk: "Exactly....anyway, that'll be $1,250. Cash or card?"

This is way more money than what you owe Sid for his....services....but you suppose this is an advance. You pay by card, not really realizing that the clerk actually counted the chastity cage in the purchase. You don't really want to make a fuss about it, so you exit the store and pay for two taxis to ferry all the stuff back home. You have to pay the driver extra to help you carry the sofa upstairs, and he gives you a weird look when you enter the apartment and all you can hear are moaning, sucking, and slapping sounds. You try and ignore him, your cheeks red with embarrassment, that is your girlfriend, now fiancée, pleasuring and being pleasured by another, more hung, older man.

After you close the door behind the driver, you take the bags of stuff and enter the master bedroom, Sid and Alyssa's bedroom, that is.

You: "I'm here, baby...."

Alyssa is on her knees, naked, ass up high in the air and her face smushed flat on the bedspread. Sid's face is buried deep in between her ass cheeks, and seems to be tonguing her asshole. They both look at you.

Alyssa: "ohhmm....hey babe, I'm so glad you're here.....now I can finally cummm....."

Sid begins to pull his face away from Alyssa's ass, and you can now see his impossibly long tongue exit her asshole, leaving it quite splayed open and lubricated, almost begging to be fucked. Her pussy is equally aroused, her labia enflamed and engorged, nectar leaking down her thighs like an impossibly sexy waterfall.

Sid: "You came just in time, any longer and I'm sure Alyssa would have begged me to fuck her brains out...."

You: "She wouldn't....I trust her...."

Alyssa: "Thanks, baby...." she says, her cheeks red and hot, she just lays on her stomach, excited for what comes next.

Sid: "ahhh, yes, excellent.....this is exactly what we needed!"

You: "It was a bit more than we agreed upon...."

Sid: "so?"

You: "So...I had to pay by card, and you owe me for the next two months...."

Sid: "Oh, if you paid by card, just leave my money on the nightstand..."

You look at Alyssa, and she doesn't seem to mind that Sid is basically forcing this money out of you.....then you take out the cash and leave it on the nighstand.

Sid: "Good boy....now, Alyssa....ready to cum?"

Alyssa: "oh my god, yes please!"

Sid pulls out the massage oil and hands it to you: "Wanna oil her up for me, bud?"

You eagerly take the opportunity to rub oil on your naked fiancée, and you enjoy every second of rubbing her naked, aroused tits, her taut stomach, her inner thighs, her lower back and her shapely legs. You are thoroughly aroused by the time you've finished, and you start taking off your clothes. This feels like the right time to finally have sex with Alyssa, finally....it's going to happen.

Once you've stripped naked, and Alyssa is looking at you with loving eyes, her beautiful pussy inviting you in and your cock is rock hard, you start to move onto the bed. Before you can get in, you feel a hand on your shoulder.

Sid: "Woahhh, calm down there, buddy....remember your promise to Alyssa....you can't have sex with her until the wedding night....."

You: "I don't care....I want to have sex with her now...."

Sid: "That's not a good idea, Matt. You need to be more patient, or you could ruin your marriage with the perfect woman."

Alyssa: "I don't mind.....I want to have sex with Matt..."

Sid: "It's only a few months, alright? You can do this, but...since you need help.....did you bring the cage...?"

You feel your cheeks burning, your cock is rock hard just inches away from pure bliss inside Alyssa's pussy, and Sid has now stopped you from enjoying her impossibly gorgeous body.

You: ".....yes...." you say through clinched teeth.

Sid: "You need to calm this monster down inside of you, for Alyssa's sake, for your marriages sake.....you should go get it...."

You look at Alyssa with questioning eyes.....

Alyssa: "maybe.....maybe we should trust him.....babe...." but you're pretty sure she's just saying it because of how horny she is, and she just wants to cum.

So with a deep sigh, you go the bag and take out the cage.

You: "I can't....put it on, I'm too hard...."

Sid: "Go to the freezer and get an ice bag...."

After a minute, you come back into the room with an ice bag, not really sure what it's for. Sid takes it off of you, leads you to the chair in the corner and holds you down with ease, he's much stronger than you. Then he puts the ice bag on your cock and balls, and holds it there. The shock is incredible and you yelp: "OOOWW! SID! STOP! FUUCK!"

Sid: "Juuuuust a bit longer.....you need to learn to control your instincts.....you can't fuck Alyssa....not yet, at least......" You whimper and whimper until you get more accustomed to the cold, still trying to stand up or take Sid's hands away. Sid is so much stronger you can't even move his hands. "Theeeeree.....let's see if you've calmed down....." he removes the ice bag just a bit and....your cock has decreased in size to even less than before you got hard! It's so embarrassingly small, especially compared to Sid's rock hard cock, leaking precum just inches away from you.

Sid: "That did the trick, now put it on."

Not wanting to get the ice bag again, you slide the small cage easily around your even smaller, ice cold cock and balls, and lock the cage.

Sid: "Give me the key...."

You: "Why, can't I keep it?"

Sid: "It's best to trust a third party with these things....you never know....you trusted me with your girlfriend, now fiancée, thanks to me. You can trust me with this...."

You: "You'll let me out when I want, right?"

The key came on a necklace, and Sid smiles with glee as you hand it to him....expecting him to let you out of this just after today's lesson.

Sid: "I'll let you out, buddy, don't worry...now, you left a job unfinished. I also need to be oiled."

You: "P....put it on yourself....I'm not gay...."

Sid: "I totally could, but this is part of the advanced lessons, Matt. I just put a ice pack on your cock and balls, we know each other well enough for you to do this for me.....come on..." he says as he hands you the bottle.

Alyssa: "Do it for me baby, this is all so....hot...." she's now rubbing her pussy to keep herself aroused....

So, you stand up and start oiling this big, old, hairy man's body, starting at the toes, working your way up the legs, but skipping the cock and balls. Then you lather oil on his belly and chest, on which the key to your sexual freedom lies. After you finish oiling his arms, Sid is so oily, and slippery. The whole time Sid's eyes were locked with Alyssa's in a primal sort of passion, nothing was said this entire time but the room was filled with heavy anticipation. After you close the bottle, Sid speaks up.

Sid: "Finish the job, Matt....you have to oil ALL of me...." as he points to his cock and balls....

With a groan, you squirt a puddle of oil on your palm and move it over his erect cock, not breathing while you stare at your hand going to touch another man's cock. Once you touch it, your instincts from years of masturbation kick in and you start lathering up his cock from tip to base, except this cock is so much larger than your own, it's at least twice the size in both length and girth. After going about three trips up and down the shaft, you squirt another puddle in your palm and fondle his balls until they're good and oily.

At this point, Sid and Alyssa are naked, oily, and impossibly horny from edging all day, and the heavy eroticism taking place. Alyssa's breathing is heavy and she's rubbing her pussy with more vigor than before. Even your own cock has warmed up quite a bit and is pressing up against the cage. It doesn't hurt but it's very uncomfortable. You don't say anything for now, since you expect Sid will let you out in a few minutes.

Sid: "There...that wasn't so bad, was it?"

You: "I....guess not...."

Sid goes to the bag and pulls out a vibrating black butt plug with a flared base, it's already charged and ready to go, the clerk said. Sid walks up to the bed and Alyssa instinctively goes to her stomach, and raises her hips up to give him better access to her asshole.

Sid: "This will make sure you cum.....we need to start training your asshole anyway....." he says as he places the tip of the plug against her puckered, but wet and oiled asshole.

Sid: "Juuuust....relaaaax....." he says as he starts pushing the plug in, her asshole is so well lubed from today that it goes in halfway pretty easily.

Alyssa: "mmmff....it hurts.....stop....stoppp..."

Sid: "Relax your muscles, do it for Matt...."

Alyssa looks at you: "I'll...I'll do it for you baby....." she says even though you never asked her to do this....

Sid pulls the plug out slightly and oils it up, then pushes it all the way in: "Theeere....that's a good girl....." then he presses the button on the end to start the vibration. You can hear a faint _MMMMMmmm _sound as the vibrating plug starts pleasuring Alyssa from within her anus.

Alyssa: "mmmfff.....oh my goood......fuuuck......"

Sid: "Hand me a cock ring, Matt" he says without even looking at you, just tugging lightly at the butt plug pleasuring Alyssa even further....

As you do, you say: "You...you can't fuck her either, Sid...."

Sid: "Yeah, yeah....the toys are to help us cum while we grind....calm down...It's not such a big deal if it happens anyway....."

You: "It IS a big deal....I'm gonna be her husband, I should take her virginity...."

Sid: "You've got your eyes fixated on the wrong thing here, Matt....if you make your relationship revolve only around sex, you're not gonna have a fulfilling and long lasting marriage...." Ironic, coming from the man who has been obsessed with sex with Alyssa, your girlfriend, ever since the night you met.

You: "I....I just...."

Alyssa: "I'll....mmm....do what you want me to, baby.....ffffuuu....." she has trouble speaking through the vibrations of the plug deep in her asshole. Her pussy almost looks like it's breathing, hungry for something to penetrate it after a long day of edging.

Sid: "Listen....we're both very oiled up, we're gonna start grinding.....if the scenario comes up that one of us pulls back just a little further than we meant to, and since we're so slippery, my cock would slide pretty easily in her hungry pussy....it would be an accident, right?"

You and Alyssa: "...right..."

Sid: "And there's nothing wrong with accidents, and they're no ones fault, right?"

You and Alyssa: "...right..."

Sid: "And since my cock already slipped inside once, there's nothin wrong with it slipping inside again.....and again....since it already happened, it's no big deal....right?"

Only Alyssa: "....right...."

You: "But....you would be fucking.....you'd be fucking my fiancée at that point...."

Sid: "If such an accident were to happen once, or a few times, let's not think of it as fucking....or sex....this would be....just stimulation....like her mouth, or hands, or tits....for the lesson...."

You: "I can't....stand the thought....it would be your cock...in her pussy.....that's...."

Sid: "We just need to get you acclimatized to the notion. I'll help you, and we can just get it over with, then you can see it's no big deal."

You: "No...please just grind...."

Sid: "Alright buddy....now, please help me put on this cock ring so I can get stimulated as well....I'm too oily....and you already touched my cock just before...."

Sid stands up on his knees on the bed in front of you, his huge cock staring you in the face, and hands you the ring. This ring vibrates, and goes around the shaft of the cock very snugly, and has a rubber band to hug the balls. The clerk said it was to force as much semen as possible out of the testicles on ejaculation. You hold Sid's cock still with one hand as you slide the ring around his cock tightly, causing the shaft to become even more veiny than it was before. "Careful..." Sid says as you reach the base and start looping the rubber band around his ball sack. After you´re done, Sid turns it on, and it starts vibrating his cock at the base, you can see the shaft and balls shaking.

Sid: "That's a good boy, Matt...now watch as I make Alyssa cum, you could learn a thing or two...."

Alyssa is still on her knees, her face on a pillow, enjoying the feeling of the butt plug in her asshole. She played with her pussy while you were putting the cock ring on Sid. Sid turns around and places himself behind Alyssa, and inserts his big, oily, veiny cock between her legs.

Sid: "We can grind here, and my cock ring will stimulate Alyssa's clitoris from below...and since we're so oily, this will be great for both of us...." he says as he starts thrusting his cock in and out between her thighs, bottoming out and staying there for a good few seconds to let Alyssa enjoy the vibrations.

Alyssa: "mmm.....yeahh......fuckk...."

Sid: "Pull the chair up to the side of the bed here, Matt....give you a good view...."

After you pull up the chair, you sit down and look at the two of them.

Sid: "From where you're sitting, it looks like we're having sex, right?"

With Sid's hips pressed tightly against Alyssa's ass cheeks, it surely does look like they're fucking in doggystyle, except for the fact you can see the tip of his cock poking up just under her belly button.

You: "Yes...."

Sid: "We're not, but imagine if we were...." he says as he starts thrusting again, bringing his cock back and forth in between her legs, generating slapping noises as his hips meet her ass cheeks, and making her moan. "You can watch this and not freak out, right?"

You: "I think so...." Your own cock is now trying it's best to be hard, but constrained in that chastity cage, it's just hurting you, you clasp your hands around the cage, trying to get it off, but it just hurts more.

Sid: "Good.....that's good...start imagining that I'm actually fucking her now....get used to the idea....it's hot, right?" he says as he starts thrusting again, without waiting for your answer, and he keeps going for a minute or so while you twist and turn in your seat, watching Sid's cock disappear between Alyssa's thighs, and watching her large, aroused tits swing back and forth, and her face drenched in lust, open mouthed and eyes glazed over. It really does look like they´re fucking, but the only thing keeping you in your seat right now is the knowledge that his cock and her pussy aren´t actually joined.

After a while, Sid stops mid thrust, and Alyssa's mouth opens wider and she lets out a little squeal, or a yelp.

Sid: "Hey, bud. Remember what we said about accidents....they happen, and they're nobody's fault, right?"

You: "What....what happened?" You say as you stand up and look behind Sid. To your horror, Alyssa's tight pussy is wrapped around Sid's cock shaft as he must have accidentally pulled too far back, and in his excitement, pushed inside of her pussy. Sid just took Alyssa's virginity in front of you.....

You: "What the fuck, Sid, take it out!"

Alyssa: "Sorry, baby....." but it's not her fault, you smile at her.

Sid: "Just look at it.....it's beautiful. It's no big deal if I push in further, right?"

You: "No! Just take it out....keep grinding....."

And he does, for a few minutes, but he accidentally pushed inside her again soon after, and then again.

Sid: "My cock is inside Alyssa's pussy again, Matt.....look.....ughh....fuck it feels good."

You: "Oh my god, Sid....stop...." You say as you see his cock stretch her pussy walls out again, almost milking his cock.....

Sid: "It was an accident....but Matt, it's happened a few times now, it's no big deal if we just...ride this accident out.....It's no ones fault, it just...happened...."

Alyssa: "Please, babe.....it was just....an accident...."

Sid: "Just imagine my cock to be your cock....you want to fuck Alyssa's pussy, right?"

You: "Of course I do...."

Sid just looks at you and pushes his cock the rest of the way inside Alyssa's pussy, placing the cock ring's vibrator fully on her clitoris, she moans heavily, deeply, like a wild animal, and orgasms right there, with Sid's cock buried balls deep inside her pussy. You can see the walls of her pussy just convulse around his cock shaft.

Sid: "Ohhhh, that feels good....I can feel your pussy milking me....."

Alyssa: "ommmmff.....fuuuuckkkk........fuck meee, baby....."

And so he does, with all pretense away, Sid starts thrusting his cock slowly in and out of Alyssa's tight, unprotected pussy. Pulling his cock out almost all the way before plunging it back inside her deeply, letting her enjoy the cock ring. Sid's cock is vein-ier than before, now that he's finally invaded your fiancée's holiest place. Alyssa's face is pressed down onto the bed as she arches her back in the perfect way to give Sid the best access to pound her pussy. Her mouth is wide open, and her tongue is out on the bed sheet, drooling all over the place, her eyes rolled up to the back, she's moaning deeply in rhythm with Sid's thrusts.

You: "Sid...stop....please...." but he doesn't he just keeps thrusting with a vigor that belies his age.

Sid: "Don't worry, Matt....this is just.....an accident......sit back....and let Alyssa.....and me....enjoy this....."

Alyssa: "uhnnn...uhnn....uhnn....uhnnn....ughhhh......"

Sid: "My cock already.....entered her.....a few times......a few more.....won't hurt....."

You don't know if it was the cage around your cock, the submission involved in oiling Sid up and putting the cock ring on him, or just the eroticism that surrounded this evening, but you have to concede that he is right. Alyssa seems to be really enjoying herself, and it's just a few more minutes until it's over...."Just....hurry up...then..." you say as you sit back down into the chair, and clasp your hands around your cage, trying to appease your cock that desperately wants to be freed.

Sid: "That's....a good boy..... just sit back......while I make.....us cum...." Sid's words are enunciated with his hips slamming against Alyssa's now red ass cheeks, bottoming his huge cock inside her small, tight, pussy.

Alyssa: "Thanks......so....much.....baby......I...love...you...."

Sid: "Fuck that's good pussy...." he says while paused balls deep inside her....then he starts thrusting again, this time with intent. Alyssa is somehow moaning louder, or more....sincerely now.

You: "I love you too baby...."

Your cock is straining hard against the cage, and your stomach feels like it´s doing somersaults inside of you. You´re watching this older man fuck your fiancée senseless, no condom, no protection. How did it come to this? His cock is so far inside of her their hips are joined at the bottom of every thrust, you´re actually slightly amazed Alyssa can fit all of him. Alyssa´s breasts are now jostling lewdly around as Sid pounds her tight pussy. She seems to really, really like this....and of course Sid is ecstatic about fucking this gorgeous young woman.

The two oiled up and unlikely lovers, joined at the hips in a doggystyle position in front of you, make all sorts of groaning, moaning, slapping, animalistic noises. You bet that the neighbors can hear this, they´re being very loud.

After a while, Sid speaks up: "Fuck....you like my cock, Alyssa?"

Alyssa: "yes....ungh.....yes.....ungh....I love it...."

Sid: "I love this pussy....."

Sid keeps slamming his hips into Alyssa's ass cheeks, determined to make the most of this accident. You can see how careful he is about extracting almost all of his cock from Alyssa's pussy before plunging back in, it's like watching a master at work. Sometimes he reaches down to massage her tits, her nipples are so aroused they could cut glass. As Sid twists them, Alyssa moans harder.

After a few more minutes of pounding Alyssa's unprotected pussy, Sid says through gritted teeth: "ohhh I'm gonna.....cum.....so....fucking....much...."

You: "Wait! Pull out! She's not on the pill....."

Sid says nothing as he grabs Alyssa's hips, and fucks her hard for a few more seconds, then goes on his tippy toes to bottom out inside of her while he ejaculates rope after rope of his sticky cum inside Alyssa's unprotected pussy.

Sid: "AAAAAAAaaaarrgggggghhhhhh......"

Alyssa: "OOOOMMMMMMFfffffuuuuuuuuuuuck......so....much...." She's clearly orgasming again, her mouth is slack jawed and she's grasping the bed sheet while pushing her hips back onto Sid's cock.

Sid: "I'm...cumming inside your fiancée's pussy, Matt.....fuuuckk....."

You: "Nooo! Sid!"

But he doesn't even try to pull out, it's so much cum that it's leaking down from inside Alyssa's pussy, even though it's filled to the brim with Sid's cock. The cock ring is clearly doing it's job to coax out Sid's semen from his balls. The cock ring you bought for him, and then put on him....just before he fucked the ever loving shit out of your fiancée.

After staying bottomed out inside of her for a few moments, waiting for his cock to finish ejaculating all of the cum he had stored, he gives her a few more thrusts for good measure, and then pulls out slowly. As he does, you can see how much of her juice sticks to his cock, and you can see the cum leaking from within her onto the bed.

You: "I....told you to pull out...."

Sid: "I know....it was an accident....nothing to worry about....it was nobody's fault....but Alyssa and I really liked it....right?"

Alyssa just nods with her eyes closed, she´s breathing heavily, enjoying the aftershocks of her massive orgasm.

Sid: "So....we'll try to not make this happen again, of course. But if it does...we know we can all handle it, right?"

You just sit there with your cage around your cock and say nothing, stunned....

Sid: "I'm glad we agree." he says as he stands up, and slaps his oily hand on your shoulder. "Congratulations Matt, you watched me fuck Alyssa without freaking out, that's quite something, she's a lucky woman, and you're a lucky man. I know you'll be perfect for each other."

You nod your head, a horrified look on your face, and then you look at Sid. He´s worked up quite a sweat, and it´s breaking through the sheen of oil you´ve rubbed on his body. His cock is still hard, and leaking actual cum now, the cock ring is still vibrating, and so is Alyssa´s butt plug.

Sid: "I'm busting for a piss, Matt. Take this thing off me." he points to his cock ring. "I'm too oily..."

You silently, and submissively, place your hands once again on Sid's erect cock, carefully remove the rubber band around his ball sack, and slide the cock ring down his oily, veiny cock, slick with Alyssa's pussy juices. You gently remove the ring from his cock, and look at Alyssa. Her large breasts are smushed up against the bed, and there is a sheen of sweat pearling on her gorgeous, smooth, skin. You look at each other and you just feel a sense of love towards this beautiful woman.

Sid: "Thanks, bud. You can remove her plug if you want."

Then he exits the room, and you only feel the desire to fuck Alyssa for yourself, but with this cage around your cock, and the key around Sid's neck, you cannot.