Caught in the Act

As you sit watching TV while your wife gets ready for a girls night out, you are not able to pay attention as you just feel your penis strain against the chastity cage. You had been looking forward to this night all week knowing you would have it to yourself. It was during these rare moments where you could fulfill your girly desires you had never dared share with your wife out of fear of what she would say/do if she ever knew.

As she finishes up, she goes over her plans about getting dinner, seeing a movie, and getting drinks after. She said to not wait up as she would just crash at a friend's place that lived downtown. You are glad about being in chastity because if not it would be very apparent of your excitement at the thought of having the whole night to yourself instead of just a handful of hours. She gives you a kiss and hug goodbye, you feel her forearm rub then press in against your cage which makes you jump a little but she just smiles at you and says not to have too much fun by yourself in a joking tone like she usually does before closing and locking the door.

You anxiously wait till you hear her car actually start to drive away before you scramble to the bedroom. You open the closet door like it is some secret vault. As you move towards the back, the small section delegated for your work clothes, you put your hand out to feel the various materials of dresses she has hung up. You pull back the handful of button ups and suit jackets and grab a large duffle bag tucked away.

You pause for a couple of seconds straining to hear anything, but all you hear is the TV still on in the living room and the ticking of the AC after it shut off. Feeling it is really clear, you move to the bed and begin laying out your items for the evening. A large enema bag, frilly undies, stockings, black, red and blonde wigs, and a variety of dildoes, plugs, and insertables.

Eyeing your own lingerie, you are glad that you are slim enough to wear the same lingerie as your wife so you grab her black corset that pairs so well with your black stockings and thong. You feel annoyed about not having shoes yet, but your feet are a good number of sizes bigger than your wife's, but make a mental note to find shoes somewhere during your next business trip.

The toys are what you eye next. As your collection grows, you always have choice overload. Knowing that you have all night, lay them out from smallest to biggest admiring them all. You pick out a simple 6" dildo, nothing too thick, just over 1" in diameter, but it is one of the very first toys you purchased and now it is the toy you start off any toy session with. Next you pick up one of your favorites, a 9" black dildo that is 2.5" at the thickest part and has a downward curve that makes you feel so good when riding it. Finally you decide to grab a toy you bought while drunk on amazon and have not been able to take it all but hope tonight is the night. You pick it up like it is some sacred idol, a super large glass plug that measures just under 3" at the widest and only tapers back down to 2.5" before a thick wide base.

Excited by everything, you go about cleaning yourself out. You start off with a single quart enema, and by your fourth enema you take a full 3 quart. During each while holding and expelling, you are making yourself frustratedly horny by reading stories, looking through reddit and other sites that were created since tumblr went chaste. Towards the end you focus entirely on hypnos and when you are cleaned out, you have nothing but a want for cum and being filled with cock.

As you get up to get into the shower, you can see long strings of precum that you greedily collected and lick up. You bring the two dildoes into the shower with you. You have some fun with the smaller, but you quickly make your way to the larger that you suctioned to the shower wall. As you lean back against, you let out a long moan as the narrow head widens and you feel your hole stretch. You rock back and forth around the midpoint and pull off to reapply lube. You go back to working the front half of the shaft before taking a deep breath and push back until your ass presses against the shower wall and you can feel the dildos silicone balls pressing against yours. As you do your best to hold it as deep as you can, occasionally sliding off and back on, you shave everything below your eyebrows. There is not a lot to shave anyways, mostly just a few areas of upkeep as you generally keep your body fully shaven, something which you are thankful your wife thinks is sexy.

Once all cleaned off and smooth, you pull off the dildo and dry yourself off. Once dry, you grab the 9" dildo and press it back in as deep as it can just before pulling up your thong to keep it in place while you finish getting ready.

You put the corset on and then sit down to roll up your stockings. As you sit, the dildo presses deeper inside and you let out a little moan as you wiggle your butt a little making you shiver with excitement. You take a deep breath to collect yourself then slowly slide up your stocking as the feeling against freshly shaved legs is just so delightful. You slide the suspenders under your thong and attach them to the stockings.

You then move into the bathroom and see your wife left out her club makeup. You were planning to go a bit simple, but seeing the opportunity, you go a little wild and very slutty. You admire your ability to contour and shape your face without making it look completely obvious it is makeup. Then you finish it off with a very bright red to make your already full lips look full on DSL's. Grabbing your blonde wig and putting it on, you can't help but look at yourself in the mirror and think you are hot enough to attract real guys to fuck your holes and leave your makeup ruined as your drip cum from your ass.

You instinctively try to rub your penis, but let out a sight as you just feel the cage. You can feel the front of the panties are wet from precum and you become very frustrated that you eye the side table where the key to release yourself is located. As you are about to go get it, you see the glimmer of light reflecting off the glass plug on the bed.

Reinvigorated to keep going, you pull your thong to the side and begin sliding the dildo in and out while moaning more and more like a slut. You stop your frantic self fucking and grab the plug. Placing it on the counter in front of you as you go back to fucking yourself with the dildo. Imagining the plug is just a really thick cock you begin fantasizing about being between two guys.

Drooling slobbering off the plug onto the counter while you are now effortlessly sliding the dildo all the way in and out, you catch your reflection in the bathroom mirror and see the crazed look. Your face is red, panting and noticing how restricting the corset is, but you can only think that the dildo is not enough and you need something bigger in your hole.

Unlike the dildos, even in your crazed mind still looks impossible to take. With it fully slathered in saliva, you press it against your hole and maybe take about three-quarters of the way to the widest point. You sigh and feel it drying off, you grab your bottle of lube and glop enough on it and in your hole and have another go at it. A couple of times you assume it's at the widest point but panic clench forcing it out.

You take a deep breath, relaxing your body as much as you can, you think of filling yourself with a huge cock, and then give the plug a hard push. As it goes past the widest part, your body sucks the remaining portion of the plug with enough force to make to stumble forward. You are panting and feel extremely full and kind of panicky if you will be able to take it out now. As you see the precum actually leaking through your panties you feel satisfied and want to continue. You collect up some of your clear nectar and bring it to your eager mouth. Savoring the taste you find so sweet and delectable that you wish you would stop chickening out when it came to eating your own cum.

As you gather your thoughts, you remember that you have all night, and decide to do some self bondage and fantasize you are helpless to some anonymous guy finding you bound to the bed. You and your wife occasionally engage in bondage stuff trying to spice up your love life, but you always felt scared of giving up control and it was usually just you trying her up and then just fucking her after some teasing and tickling. You bought a ring gag to take it a little further, but it was too big for her so the two of you never used it, but you used it by yourself all the time.

You move towards the full length mirror on the closet door, noticing a slight waddle in your step because of the plug, get even more aroused seeing your slutty made up face with bright red lips stretched taut around the ring. Your faithful 9" dildo is too big for the ring, but you go grab a narrower 7" that fits just perfectly through the hole. As you slide the dildo through the hole a couple of times, you go as far as it can go purposely making yourself gag. As you pull it out, you revel in seeing the drool drip down your chin as well as your eyes watering making the makeup run a bit making you look even sluttier.

You open your wife's side table drawer and pull out her instant camera. Snapping a selfie to capture this moment of complete sluttyness, you look at it with pride. Opening up the side compartment of the duffle bag, you pull out a handful of other selfies taken. Each is proof of your feminization that you treasure. You laugh seeing how far you've come in just a couple of years. As you look through the pictures, you remember about the first time you dressed up.

Your wife had been out of town for a week and was not due back for another. Having had a few to many drinks and being really horny even after masturbating a number of times you looked through her modest lingerie collection from when you two first started dating. Seeing a satin nighty she bought and maybe wore once, you slipped it on just to feel the softness against your skin. The erection was instant and seeing yourself in the mirror, the idea sprung to life as if something in you had been awoken from a deep sleep.

Putting the pictures in your bag before putting all your currently unused toys back in it and placing it on the ground. With every step making the plug shift, you are leaking like crazy. Glad the bedroom is tiled, but you take the sheets off the bed and cover it with some towels to not leave a stain before retrieving the restraints tucked under the bed.

Knowing you set up the restraints that would allow your wife to easily escape just in case, you go about applying the cuffs to your ankles. Kneeling on the bed, you take a deep breath before grabbing the blindfold and slipping it on so it is just on your forehead before laying down on your stomach and pulling the cord with the wrist restraints. After closing the restraints, you lower the blind folder and let your arms extend outward feeling the tension of the cable coil back.

You feign to struggle as you wiggle around and moan and drool through the ring gag. In your mid you are about to be fucking and start grinding into the bed feeling like you are actually about to cum. Just as you near the point of climax, you swear you heard the front door. In a panic you try to pull your arms in and feel the tension locks click preventing you from pulling them closer. Damning your idea for the tension locks to prevent retraction if pulled quickly, your fingers blindly fumble for the quick release mechanism on the cuffs. After 30 seconds pass your heart freezes as you realise the mechanism is not there.

Full panic sets in, but you freeze completely as if you know you are being watched. You strain your ears trying to figure out if you are alone or not, but with all the adrenaline coursing through you, all you can hear is your heart beating ever louder in your ears and feel like all your muscles are tensed like it is expecting to be touched by some external force.

You let out a scream as you hear a sound from inside the room. Even before you can think and realize the sound came from the shutter and flash of the instant camera, your heart sinks as you hear a laugh that you distinctly know is your wifes.

"I knew the promise of a full free night and 4 hours would be enough time to catch you in some perverted act, but oh my god, I never would have guessed this. I had wanted to be the dom for once, but you were always so reserved and unwilling, I planned this surprise by changing the locks. I knew you had a bit of a freak flag, but you seemed so concerned about anyone else knowing about. This also explains why I thought my lingerie felt stretched." As she is talking, you can hear her heels coming closer, then her hand stroking up your leg to your exposed balls cupping and caressing them. "Girls clothes is one thing, which you do look very cute in this outfit, but chastity and that looks like quite the butt plug...all I can say is wow, you really surprised me tonight."

You jump as she flicks the plug before she says, "I remember one time after a night of drinking I was blowing you. I had just thought you wanted me to spank you as you slid my hand towards your butt, but now I see you wanted me to explore your backdoor." She gives the plug a little push eliciting a moan from you and a noticeable increase of your already leaking member. "I truly never would have thought you were such a butt slut, that puddle forming is impressive." You feel her hand touch the tip of your cage stroking the tip of your manhood that is pressing hard against the restraint that it probably looks ridiculous.

Her hand gently reaches under your head turning it towards her as you had looked away out of not wanting to look at her even though you are wearing a blindfold. You resist a little, but let her turn you towards her. As she lifts the blindfold you are not sure what to expect. Even though you can see some surprise, it is one that has a gentle warm smile on you that makes you feel safe. You then see the glistening finger covered in your pre-cum and look at it with longing. She moves the finger towards your open mouth which you stick your tongue out to accept the finger. She lets out a soft giggle as you close your eyes and attempt to suck her finger and groan in annoyance that you can't because of the gag.

"Wow, there was no hesitation there, do you also eat your own cum?" Your eyes shoot open and look at her, but then slowly close them again as you shake your head no.

"Well for the number of times you failed to warn me before cumming in my mouth, I feel that is unacceptable, but that is something we can discuss later." She gently caresses your cheek taking a closer look at your face, "you went quite overboard with your makeup tonight, were you trying to go for the slutty whore look?" Your eyes close once again and you shake your head yes.

She looks around the room for a bit before turning back and looking at you. She leans over and kisses your forehead before sliding the blindfold down again. You feel the bed shift as she sits on the bed and begins sliding a finger across your body giving you goosebumps. After a minute of sitting there, you feel her stand back up then the noise of the duffle bag being picked up and placed on the bed. You can hear her moving the items around with the occasional giggle and gasp. Next you hear the side pocket being zipped open and you realize she will find your selfies.

"Again, you are full of surprises, just based on these, you have been doing this for quite some time. Oh wow, this must have been one of the first times based just on your makeup, looks like a teenage girl who never heard of blending and thought the more you put on the better. Don't worry, even though your makeup tonight is all runny, I can tell you have gotten quite good at it." You hear her put them back in the bag while saying, "I added the photo I took of you when I came in, I wanted to add to your collection so you can remember how your wife found you."

You are surprised that you can feel the blood rushing to your face even more.

You hear her heels move towards the bathroom. Your mind is racing as your ears strain to hear anything you can. There is a bit of rummaging noises, but nothing you can discern. It feels like it has gone silent forever, then realize that she must have taken off her heels because the next thing you feel is her sitting on the bed.

"Looking at the dildo on the counter, I can see the distinct lines of lipstick down the shaft, do you like to pretend you are actually sucking someone's cock?" You feel very embarrassed and hesitate, but slowly begin to shake your head in affirmation. As you shake your head up and down you feel the tip of a dildo begin to pass through the ring gag. You pull back with surprise, but then let her stick it further into your vulnerable mouth. She does not press it deep and seems to be appreciating your tongue doing its best to suck and lick as much as possible while letting out little moans. After shallow fucking your mouth she starts pushing it further and further until it cannot go any further and the silicone balls are resting on your chin. As she holds it there you hear her say, "who would have thought my husband was quite the cocksucker, can you breathe with it in like that?" You nod affirmatively. A second later you feel something being pulled over your head and securing the dildo in place. It takes you a second, but then you realize it is a pair of panties, and they feel warm which tells you it is the pair she was wearing.

"Tonight I had just planned to catch you bound, have a little fun with you, give you a BJ, maybe tease you some, and then finish it off with some good fucking. Now my mind is just going wild with ideas I am not sure what I want to do next"

You feel her hand once again stroking your back, moving further and further down. You feel her fiddle with your suspenders then stop and just grab your underwear sliding them down until they are just past your ass. "I am not sure if you are just a natural slut, don't know how it is supposed to work, but the idea that you wore your panties on top of the suspenders is nice as it meant I could take them off without removing the suspenders."

She starts rubbing your ass before her hand starts caressing the inside of your ass cheeks. She slips them past the plug before grabbing your balls. She adjusts herself so that she is straddling your back. As she slowly massages your balls, you feel her weight move forward then her hair touching your legs and her warm breath on your balls. She gives them a squeeze as she grips her fingers to create a ring around your sack. Her tongue begins to flick your smooth balls before sucking on them.

Even with the dildo stuck in your mouth, the moans are becoming quite loud which encourages her further. You can feel yourself about to burst, but she stops and you feel her get off your back and off the bed. You then hear the sound of what you think is paper ripping and then something being put on your chastity cage. "You are leaking so much, now that condom will make sure none goes to waste."

Her hands begin rubbing each of your ass cheeks moving then up and down and spreading them further apart exposing your plugged hole. You begin to push you ass up and back against her hands. You are moaning and pleading in your head for her to play with your hole. As if she heard your thoughts, she stops rubbing and you feel her hand fumble around trying to get a grip on the exposed part of the plug. As soon as she slips her fingers under the base, she tests the plug by slowly pulling on it lightly. As she starts to pull with more consistent force taking it very slowly you feel the bulb begin to expand your hole. As the plug part is just about at the widest part, your wife let out a gasp and let go of the plug, and as it was quickly sucked back into your hole, there is an audible plop noise alongside you lurching forward and mewling along with almost frantic breathing made much harder with the dildo filling mouth.