It Just Knows What Scares You

"It just knows what scares you and turns you on" the woman says as I approach the chair. The restraints look very heavy duty - chest straps, two or three leg straps, wrist and arm cuffs - once I'm in the chair and the headset goes on, I am not going anywhere.

"I mean I trust you but this is a lot of money, it better be worth it." I say to her.

"Oh it definitely is. When I did it, it scared the shit out of me." she replied "the AI just has a way of using your brain waves and your social media to show you exactly what you are most scared of, in a sexy kinda way."

"So what did it show you?" I say taking my sweats and hoodie off and chancing my arm at getting some cheap titillation.

"Well I went in expecting it to show me some sort of sexual assault - cos, let's face it, that is terrifying. But it didn't. Somehow it knew me better." she says sitting my naked body down on the chair "what it showed me has haunted me ever since. Unsatisfying vanilla sex with someone who was fucking beautiful and amazing in every other aspect.   We'd have this amazing house, he was absolutely ripped, he was so funny - he turned me on so much I just wanted to devour him - but then we went to bed and he just robotically slid in and out.   No foreplay, no kink, no words, just the most boring intercourse ever. It was utterly heartbreaking to be so turned on but also so unsatisfied"

"So you guarantee it's going to be sex related?" I say as she fastens the buckles of the straps across my chest. "It's not going to show me dying alone, slowly being eaten by snakes?"

"Not unless that turns you on!" she says as she continues with the ties on my arms and my legs. I do try and think of what turns me on and my cock responds to thought of the good things it could see.

"There's a whole bunch of toys under the chair and in the walls. The chair will use them when it knows you need them." she says as I feel some cold air rush against my unsupported ass "The program will start once I leave the room.   I wholeheartedly recommend that you interact with whatever you see or hear as you get out of it what you put into it, it's interactive it's not a movie. If it gets too scary and you want out you need to say 'blueberry' THREE times in quick succession."

I nod as she fastens the immersive helmet over my face. I can hear my own breath. Every exhale hits the opaque screen in front of me. Five breaths. The woman's voice in my ear says "I'm going to close the door. I'd say enjoy but....."

Her voice trails off. Another handful of breaths is all I can hear. My heart thumps in anticipation.

And then there's a ringing. Like a mobile, or Teams or Zoom. I try and grab an imaginary mouse forgetting already that I'm tied to a chair

"Hello" I say to nowhere "Hello who is this?"

A face appears sitting at a desk looking like they're staring into a web cam.   "Hello this is Doctor Jones" she says.   Her brunette bob is slightly wavy at the bottom.   I know this face from somewhere.   I recognise those cheekbones, those eyes and those red lips.

"Oh Jane!" I say finally remembering her first name. She looks at me blankly.   "I've not seen you in ages - we knew each other way back - through my sister."

I had such a massive crush on her.   She worked in a department store during college, which just happened to be next to the sports bar I had to pretend I liked to go to so I could walk through there and accidentally bump into her.   I didn't always go over and talk to her, sometimes I would just walk through to see her in the distance so I didn't pester her too much.   Her uniform - black tops, black skirts and black tights - definitely started my obsession with legs, tights and stockings.

"You know - Jules' brother - we lived in the house with the red door, we always had that big BBQ in the summer?" Jane still looks at me blankly.

"Oh yeah, it's been ages hasn't it?   Must've been about fifteen or twenty years.   Fancy meeting up with you like this." she says.

There's an awkward pause.   Trying to fill the dead air I say "How's life?"

"Yes good" she replies tersely.   There's more silence.   "OK, so unless you have anything specific for me - I think I'll leave it there."

There's a pause and I smile.   Whilst it was nice to see an old face, and a beautiful one as that, this was not exactly what I had spent all my money on. "Just before I go" she says "Do you still masterbate to that photo I posted on Facebook back in 2012?"

Oh that picture.   She had been doing some sort of crossfit back then and was ripped as fuck.   She was on a night out in a bar wearing these low rise jeans and a crop top.   She was turned to the camera slightly and you could see the indentations of abs on her stomach.   She had that beautiful line that runs down the side of the hips and draws your eyes into her jeans to imagine what it was leading to.   I can see that picture as clear as day.   Or did I actually see that picture?   Did it just flash up?   The mental image of that photo is so clear I can't tell if I'm imagining it or if I saw it.

"You know" she says carrying on "when they asked me to take part in this, I couldn't remember who you were.   They sent me photos, they sent me detailed description as to who you are.   And I had no recollection of you at all."

She said take part?   I thought this was AI generated? This can't really be her can it?   I can feel something gently brushing against my cock.   This is really not the right time to get hard.

"This all must be pretty embarrassing for you?"  she says as the video starts to zoom into her lips "we're not even friends on Facebook are we? So you've searched me out, gone through my photos and kept that for more than a decade and still wank off to it"

A paddle starts slapping my balls. The slaps are light but they are relentless, hitting the same spot over and over. The more the paddle taps the more painful it becomes.

"That's pretty fucking creepy you know.   I mean not as creepy as the way you used to stalk me when I was work." she says "I wanted nothing to do with you then and I don't want to now. I never have."

The thing that was gently stroking my shaft applies more pressure and begins to vibrate. Up and down the underside of my shaft. Faster and harder. The paddle hitting my balls has slowed down it's frequency but has increased it's power and strength.   I groan from the pleasure.

"Are you..... Enjoying this?" Jane says and I fumble a yes as I look at her lips smirking at me as the vibrations increase and focus in on the underside of my cock head bringing me right to the verge of orgasm "That's really fucking disturbing. What sort of person enjoys this level of humiliation? You have to be one of the most disgusting human beings on the planet."

The vibrations stop, the screen goes black and I'm no longer being whacked on the balls. My head drops forward and I shake my cock around, trying to get some sort of stimulation. I need to cum. Why do I want to cum? I've just had one of the most humiliating and embarrassing interactions I've ever had and all I can think about is how turned on I am as I stare into the black void of the helmet.

What's that smell? I think to myself as I'm resigned to not getting that orgasm I need.   It's orange? And lemon? Very citrus. I know that smell. That's just like what my ex Amy used to smell like. Her apartment. The candles she'd burn. I blink a couple of times and I'm in the hallway of her apartment.   I'm walking down towards the living room.   I can hear someone groaning somewhere. I turn into the room and see her boots lying on the floor.

Amy was the woman who made me feel comfortable enough to be admit I wanted to be dominated. She'd wear those boots out on a date and it would be the longest teasing session ever.   As soon as I saw them, I knew full well that once the date was over, I was getting fucked up.   The very worst one (and therefore best!) I remember was when we went to see an afternoon screening of a film and after fifteen minutes, she leant over and told me that she was going to make me regret having a boot fetish.   At regular intervals she'd lean over and whisper a threat to me "Do you think I could kick you so hard that your ball would rupture?", "Maybe I'll take my heel and stab it through your cock".   With about twenty minutes to go in the movie she told me to kiss her boots and said she'd show some mercy on me if I stayed there until the end of the movie.   I was hard for the entire silent trip home thinking about what was to come.   When we got home, she made me immediately strip and lie down.   With my feet braced against the external door, she began dragging her heel up and down my shaft.   It probably took about a minute before cum was dribbling out of my cock as the pain and teasing had driven me to agony and ecstasy.   She made me lie there with cum drying all over my stomach and hips for about a half hour, she walked past me on several occasions, spitting on me, before telling me I should shower.

She was perfect, I was in love, I proposed, she said yes but...... only if she could also sleep with real men.   I thought she was joking.   She was not joking.   We broke up. 4 had months passed since then.

But - I am still in the room.   I'm still looking at her boots. I'm noticing a white blouse on the sofa.   Some tights and a pair of black lace panties on the coffee table. A groan comes from the bedroom followed by her voice. "FUCK ME PLEASE" I can't forget that accent. I'm walking towards the bedroom door. She's obviously in there. And then I see another pair of trousers and a polo shirt. I don't want to open the door. What I see will crush me. I don't want to turn the handle but I have no choice.

The door opens and I step inside, just in time to hear her yell "I'm coming!".   And there she is, on her knees and elbows, head down. She hates doggy, she always said she wanted to see my face. I can hear him slapping his skin against her.   I can't see him.   It's too dark.   The only spotlight is on her.

Her head arches up into the light.   "Well hello cucky." she says.

"Hi" I reply noticing how her arms are more toned, her waist thinner and her smile wider than I remembered.   It had been months now and I was moving on.   But seeing her body, her face and hearing a cock sliding in and out of her cunt is making me miss her.   And it was making me hard.

"I have missed you so much" she said as the sound of skin on skin continues. "I was devastated when you left me, I thought you knew I wanted some real cock.   Did you not want to make me happy?"

I feel a plastic sleeve slide over my cock.   It's well lubricated and it's moving at a slow pace.   It slides over the head of my semi hard cock and the sensation of the little ridges and bumps stimulates the shaft as it slides slowly down to the base.   As it begins to slowly pull back all I can do is moan.

"I knew you wanted me to be happy.   Seriously though, what woman wants a little sissy as her husband.   What do I get from kicking you in the balls?" she says as my balls get a short sharp slap as the sleeve carries on sliding up and down my cock at a frustratingly slow speed "Watching you beg me to hurt you?   What fucking loser does that?"

A cane or a whip appears out of nowhere, and slaps me across the chest.   I jolt in the chair rattling the restraints.   Another and another land.   One from the left, two from the right.   Two more to my thighs.   I yell in pain.   It stings.   The sleeve twists causing a lovely pleasurable senstation on my cock as it slides back down.

"It was always you, you, you!   What did I ever get out of it?   Do you think I enjoyed watching you......"  she says, pausing. Her neck arches back, she looks to the ceiling. Three short gasps of air and long pause. I see her shoulders begin to tremble. She exhales and her head falls back to the bed. The masterbator slides up and down my cock faster and the cane hits me again and again across my thighs. I can feel myself on the edge of cumming.

"Fuck where was I?" she says recovering from her second orgasm in the short time I've been in the room. The sleeve stops rubbing me. "I never came that hard when you were fucking me did I? How could any woman cum hard with a man so submissive he always asks for permission to cum? Do you think this man asks?"

"Look you want me to be happy"  she carries on as the plastic pussy slowly slides down my shafts at a much slower speed "And getting a real man's cock makes me happy. But obviously since this is about my happiness, we'd have to do something about your cock. Chastity? Castration? Hmm.... And obviously my man here may want the occasional blow job, and I'm certainly not doing that, wait till you see the size of this thing. So we'd have to train you up to do that. You'd basically just become like a roommate of mine who occasionally deep throats my boyfriend. Technically we would be married I guess but emotionally, I could never commit to you. I just need more."

I try and look and see the man but can't it's too dark. I love her and I've always wanted her to be happy but having her be pleasured by another man is heart breaking. I could be doing that. I should be doing that. I don't like this.

The sensation in my cock as it's being rubbed and massaged and the stinging in my thighs from the beating they have taken is causing a strange surge of emotions. Maybe I should reconsider? There's something about seeing the woman I loved, or do I still love, enjoying herself. But the emotional pain of it not being me and the thought that I'm not enough terrifies me. The plastic sleeves twists left and right, bringing me back to the edge of orgasm.

"I mean it's not like you'll meet anyone else who treats you as well as me, is it?" she says as the light disappears, the screen goes black and I hear her begin screaming as she has another orgasm. The stimulation on my cock stops. The sleeve withdraws. I have a moment in the blackness to recover emotionally and remind myself that I'm just in a simulation.

Within a second, the screen lights up and I'm in the reception of my office. And my co-worker Zoe walks in.

"Hey stranger" she says walking towards me in her long black leather trench coat. Her pink hair always makes me smile. The blonde and pink curls are so beautiful. "not seen you in the office for a while."

We exchange pleasantries as we walk towards the office door. She stands by the door and coughs. I swipe my card and open the door for her as she gives me a sexy side eye.

"So before you go to your desk, I have a question." she says grabbing my forearm. "Why won't you ask me out on a date?"

"Erm" I say trying to find the right words because I really wanted to but I was still getting over Amy and was very wary of dating another strong, confident and forthright woman. "I didn't really want to ruin our friendship, I value that too much"

"Ha!" she says with a laugh that cuts a little too deep "Seriously? What friendship? I ask you to do stuff and you run around like a little simp getting me coffee and picking up my dry cleaning. Do you think that's going to change if I fuck you?"

I turn to look at her. She's stood there with her arms folded and a knowing grin on her face. I feel something cold pressing against my ass. The plastic head of a dildo, it starts to slowly push apart my hole. The first inch seems to take forever. I can feel myself gradually opening up and accepting it.

"Or are you worried that you're going to enjoy being dominated by a confident woman" she  says as the dildo overcomes the initial tightness of my ass and slides easily inside "or should I say dominated by ANOTHER confident woman. You little slaves are all the same. I could see right through you immediately. Your second day, when I introduced myself and your eyes never got higher than my boots. That was when we knew."

The fake cock is now sliding easily in and out of my ass. The angle of it slightly changes. I feel something I've not felt before from the handful of times I've been pegged. Is this my prostate? The feeling is nice. The plastic cock begins to tingle and vibrate.

"Why are you so worried about us dating?" she says as I look out over the office trying to hide the discomfort of having a vibrating cock in my ass massaging my prostate. She puts her arm around me drawing my closer. The fake leather of her coat smells fantastic. "Are you worried that I'm going to tell the Kate over there by the photocopier that you enjoy having me ram a dildo into your ass? Don't worry because she already knows"

"Are you worried that Joe, the finance guy who knows your cousin, will see the photos I'll take of you eating me out as you make me cum?" she says as the thing in my ass begins to inflate and deflate several times. She has turned to whisper in my ear and I can hear her lips moving "well he already knows you're not a real man - why else do you think he stopped hanging out with you?"

"Amelia over there is just waiting for the moment you're outed." Zoe says turning me to the corner of the office where I can see the HR manager with her legs up on her desk and her bright pink heels dangling off her toes "She loves having her toes sucked. And the moment you are outed, your mornings are starting with licking and sucking her toes as she uses her vibrator"

"Does the fact that I'll show your boss videos of me laughing at you whilst you're bent over double spurting cum all over your face scare you?" she says as the cock goes back to sliding in and out at a much faster speed. I can feel her hair brushing against my neck as she stays really close. "because it shouldn't. She already knows who you are. She told us before you were even hired. You reek of beta energy. Everyone in the office, everyone you've ever met - they know who you are and what you like"

"And I realise, if I'm going to fuck you" she says pulling away from me and once again letting me see her in her full glory. "I'm going to have to take the lead."

Like a subliminal message within an advert, I see a quick frame of Zoe stood there, coat removed, wearing a tight black catsuit and a strap on. I get three fast strokes of the cock in my ass and then it retreats and a logo appears and a robotic voice says "Thank you for booking with us and making your fantasies come true. I hope you've enjoyed your time."

"Right I'm going to remove the helmet," the woman's voice says after a minute or so "We recommend you take your time to reacclimatise while I unbuckle you"

The helmet comes off and as the woman undoes the straps I look down at the welts on my legs and flex all my extremities not realising how still I'd been.

I get dressed and go to leave. As the woman escorts me out she whispers to me "I'm not supposed to say this but what I saw on your headset, that was fucking hot. It's the sexiest thing I've seen anyone experience. I had no idea there were men out there who had such depraved fantasies."

I smile at her as I stumble down the corridor trying to get my balance.   "One more thing" she says "Zoe...... Erm..... She's in my Wednesday Pilates class. I recognised her hair. You should ask her out, she's fun. Obviously I'm bound by confidentiality and can't say anything about what happened here, so your secret's safe."

It's several hours later and it's 2am, I'm lying in bed thinking over what I saw. Should I be fantasising about someone who I've not seen in over a decade? Do I want to be a chaste, bisexual, cuck just so I can be around Amy? Was Zoe right? Does everyone know who I am and what I'm like? Should I ask her out?

And there's a ping on my phone, my security camera has picked something up outside. I open the app and go to the live view and turn the microphone on so I can ward off any potential burglars. There's someone walking towards my house. She's wearing a long black leather trench coat, I can see the reflection of the light. The picture is not good enough quality to see her face from that distance. Then she gets closer and I see it's Zoe. Dressed exactly the same as she was in my vision.

She gets close enough so the quality of the picture is good enough to make out that she is untying the belt of her coat. It parts, showing that she's wearing a catsuit and a strap on. She looks exactly like that snapshot I saw earlier.

Wait? Am I still in the simulation??? "BLUEBERRY BLUEBERRY BLUEBERRY" I say out loud hopping to stop this.

"Oh sweetie, you're not in the virtual reality any more. This is real life" she says looking into the camera "now let me in so I can fuck your ass".