Trans Damsel Stories 01: The Spy

So this is my very first attempt at erotic fiction, hope it turns out well! This is going to be in second person, and will have two alternate endings. Anyone reading this would be more than welcome to make illustrations and turn this into a comic or an erotic hypnosis audio (maybe a more gender neutral one). I really enjoy peril and roleplay stories, especially with BDSM. I hope you enjoy it this!

Story:

Being a secret agent wasn't always so glamorous. You remembered that fact during the taxi ride from the airport. The flight had been uneventful, and the mission went so smoothly it might as well have been routine. Thankfully the intel you collected was incredibly valuable and was well worth the trip. You remembered much more exciting missions you'd done in the past and were almost grateful for the comparative boredom. After all, anyone else would kill for the travel and luxury hotels, with first class flights paid for on the company dime.

The taxi pulled up to the apartment complex, and you grabbed your luggage as quickly as you could to run inside. You liked your home city. It wasn't a gleaming metropolis, but it had everything you would ever need downtown. It also had a very beautiful skyline, and your apartment offered a fantastic view. By all accounts you are an incredibly attractive secret agent, with an athletic build forged by training to complement your perfectly sculpted ass. Your tits are small but firm and substantial, and your beautiful features are mesmerizing. You usually like to keep your hair short to help with more dangerous missions, but since you've done less physically dangerous jobs you've allowed your long dark curls to grow out. You've been mixing business with pleasure much less than you did earlier in your career, but you've had plenty of fun on the job. The part of you that's been most surprising to lovers is your cock. It's not exceptionally large, but you use it well and you've never disappointed anyone with it.

Your sleek modern apartment is clean, just like it was when you left for the airport. You usually take great pains to keep it pristine, but the constant travel had taken a toll on your sleep, and you are simply exhausted. You throw your luggage by the couch in the living room and left your leather jacket on the back of a chair. Slipping out of your boots, you make your way to the room and pick out a bathrobe and a clean pair of white cotton panties. You want to be comfortable, taking off your jeans and your t-shirt before stripping out of your underwear. The shower is delightful, but you don't take long. All you want to do is relax in bed, and you slip on your clean panties and wrap yourself in the fluffy bathrobe. Hotel beds cannot compare to the comfort of your own bed in your own home. After a few work emails and texts, you feel comfortable with finally relaxing for a long weekend. If you were less exhausted you might even pour yourself a glass of wine, but you are content to lay on bed and slowly doze off.

Something was wrong. You aren't sure how long you were asleep, but you can feel something wrong in the room. Someone was in the apartment. You tie the belt of the robe tight and leap from the bed, watching and listening for any sudden movements. Your gun is locked away in a safe in your closet. It was unnecessary for your last mission. You kept the safe with your diverse wardrobe of evening gowns, bikinis, catsuits, pencil skirts, and all assortments of outfits that an agent might wear on the job.

"Anyone there?" You call out.

You know something's wrong; you've learned to trust your hunches from experience. It had grown dark outside, and you can hardly see anything in the room. Before you can hit the light switch you see rapid movement. Almost automatically, your reflexes and training kick in, and you close the distance with the intruder. You're surprised by how attractive she is. She's dressed in a black sleeveless spandex bodysuit with thigh high boots. Her mouth and nose are covered by a black mask and her long black hair is tied back into a ponytail. Her eyes give nothing away, and you can immediately tell she's a professional. You notice an open window and realize she must have climbed into the apartment.

"Who are you?" You ask.

"I have some questions for you." She responds coldly.

You don't even wait for her to finish before lunging at her. You've developed an acrobatic style of fighting that has served you well on your missions before, but this opponent seemed like she knew what you would do. She quickly dodges and slips behind you, grabbing your arms from behind and pinning them together. You use your legs to push off the wall and try to break free from her grip. You both crash to the floor. This seems to work, and you briefly have the initiative. You try to pin her down, holding her by the wrists. Before you can figure out your next move, she's able to throw you off. You then realize how strong she is. She grabs you and throws you onto your bed, then crawls on top of you and holds you down. You struggle as much as you can, but there's no use, she's far stronger than you can imagine.

"Stop squirming, you know you can't win." She says and turns you over onto your stomach.

You ignore her command and keep trying to break free, but it's no use as she pulls the belt from your bathrobe and binds your wrists together. You try to break free by kicking out your legs, sending your bathrobe wide open, but she quickly grabs your ankles and binds them together, no doubt with her own rope that she prepared for the mission. You kick and writhe helplessly, but she just watches in amusement, taking the time to cup your exposed breasts in her hand.

"You're going to be interrogated and tortured like the helpless little slut you are." She sneers. "I know what your weaknesses are, I've read your file."

She flips you over and runs her hands over your body, feeling her way slowly down to your swelling cock.

"I'm going to torment you the old-fashioned way before I take you back, but this incessant squirming and struggling just won't do." She says as you try to wriggle away from your predicament.

Her hand that was groping your cock moves away and she walks towards the window, revealing a thong back on her bodysuit. You try to struggle and succeed in freeing your hands, but before you can untie your ankles, she is back with a wet rag that she shoves into your face. Despite your best efforts, you breathe in the substance and fade into unconsciousness.

You wake up to find yourself tied spread-eagled to your bed, with firm dark ropes binding your wrists and ankles to the bedposts. You're gagged with tape, unable to scream or yell for help. Your bathrobe's been stripped away, and you are naked except for your panties. Your erection faded away while you were unconscious, but you can feel the faint stirrings of arousal despite yourself. The intruder notices you're awake and pulls her mask off to reveal a sadistic smile.

"You should get used to this position. You'll be tied like this for a lot of the night." She warns.

You notice some objects on the end table besides your bed, but you can't quite make them out in the darkness. Your interrogator sees this and turns out your bedside lamp, revealing an array of sex toys, some of which are yours. To your embarrassment, she runs her hands through your assortment of vibrators, flesh-lights, cock-rings, and masturbators.

"Not been getting much action lately?" She purrs.

Glaring at her, you try to break out of the restraints, thrashing and struggling with all your might. You're still weak from the chloroform and the tight bonds are too strong.

"You'll be tortured and made to regret getting in the way of my organization. You see, the thing we do differently is that we like to torture you with pleasure, instead of pain. I'm going to make you beg to join us and switch sides. We have so many gadgets and toys back at our base, but me, I like going old school." She climbs on top of you and begins fondling you, running her hands over your body.

Her hand slides into your panties and grabs your cock, rubbing it until it's rock hard. She pulls down your panties and exposes your throbbing hard penis. She brings her face down to your breasts and begins licking your nipples while she strokes you. Her hot breath on your nipples and the firm hand stroking you has a powerful effect on you. Your struggling starts to slow down as you feel the pleasure warm you. She brings her mouth down and places her succulent lips around your shaft. She sucks you well, making you gasp.

Even under your gag, your breathing is growing heavy, and you can already feel her bringing you towards an orgasm. Sensing this, she grinds her teeth against the head of your penis, causing pain and discomfort. She crawls over you, sliding her pussy against your cock, and reaches for a vibrator from the end table. She turns it on and runs it over the head of your cock, down your shaft, and presses it underneath your balls. She vibrates you while stroking you, bringing you again to the edge of an orgasm before she stops. You thrash and squirm as much as you can, wanting desperately to make yourself cum.

"I love watching you struggle. You're horny and helpless. Just the way I like you. I'm going to watch you squirm." She pulls the spandex covering her pussy to the side, revealing her clit.

The vibrator buzzes to life and you watch as she pleasures herself, arousing you deeply. Precum is dripping off your cock and onto your panties. Despite your best efforts you remain tied to the bed, forced to watch your enemy cum in front of you. If you weren't gagged with tape, you'd be dripping with drool in arousal. You have no choice but to watch as she brings herself to an orgasm. A gasp escapes her lips as she shudders. With her orgasm complete she looks at you.

"Want to cum too?" She asks you.

Despite yourself, you nod vigorously, moaning through the gag.

"Too bad!" She laughs evilly.

She ducks down under the bed and returns with a strange device attached to her wrist. Before you can realize what, it is, she aims it directly at your face, and a mist washes over you, instantly causing you to lose consciousness. You periodically drift in and out of consciousness, almost as if driven by willpower. Even though your body is limp and overcome with weakness, you are hogtied with handcuffs and resting face-down on a cart being pushed by masked men.

Your mind groggily drifts, as you memorize the protocols for being captured. You've done some rescue missions in the past, and you remember encounters with the grateful damsels in distress you saved. On your first mission you fought through a small group of goons, fighting your way into a warehouse to find the captive. You were magnificent in your skintight catsuit. He must have noticed how sexy you were when you rescued him. He was strung up naked, hung up by his wrists. His interrogator, a cruel dominatrix had been torturing him and was just about to kill him. You saved him in the nick of time, fighting your toughest battle, but ultimately coming out on top. After releasing him from the straps, you had one of the most memorable nights of your life back at the hotel.

You're still bound face-down when you drift into consciousness again. You know your agency will come to rescue you, but you don't know how long you need to hold out. You wore a sleek black bikini for your second rescue mission as you had to swim to a remote base in the water. You snuck in to find your fellow agent tied to a chair naked with a vibrator pressed tightly to her clit. She'd no doubt been forced to orgasm over and over again by her captors. You made sure to leave no trace of the base behind when you both escaped, rigging the whole base to blow. The memories of your time with her float by as you fade out of consciousness.

You fully wake up in a strange room, with bright lights shining down on you. You are strapped down to a table, facing the ceiling. Weakly lifting your head, you look around. You feel something strange around your cock and you look down to see a device attached to your panties, which have no doubt been soaked in pre-cum. You also notice wires attached to your nipples and other sensitive parts of your body. They are attached to machines and computers. The room is surprisingly warm, which provides a little comfort to your exposed body. You wonder if it's worth yelling out for help, though you are undoubtedly deep within an enemy base.

The straps holding your wrists and ankles are strong. You still try them, but it's no use. Your arms and legs are held down tight. The door is behind you, and you hear it open, with heavy booted footsteps slowly walking in. You hear mechanical whirs as your table moves to hold you upright, spinning to face your visitor.

"Liking the accommodations?" She asks.

You see a beautiful older woman with jet black hair. She is dressed in a shiny black leather bodysuit with long sleeves, and long boots that looked like the ones on the agent that kidnapped you.

"Welcome to our lair. You'll have a choice to make soon. You see, our organization has been at odds with yours for years now and we've been developing all kinds of new techniques and tactics to neutralize your agents. We admire the skills you have, and we could use someone like you on our side." She offers.

"Never! I'll never join you! And my team will come for me. You'll regret this!" You yell back defiantly.

"Good! I wouldn't want someone who didn't have a backbone. And I'd also love the excuse to torture you. I'm excited to try out this new device." She approaches you and touches the device attached to your panties.

"Who are you? What is this?" You demand.

"Who I am isn't important, but this device is. This is our new compliance device. It makes for exquisite torture. It will start pleasuring you, getting you all hot in bothered and turning you on. It can bring you to the edge of orgasm, then it can turn off. Edging you constantly. Some of your colleagues that I used as test subjects lost their minds after hours and hours of edging. It also serves as an execution device. If turned all the way up, the subject will simply orgasm to death." She is stroking your body as she explains this, running her fingers over your cock and squeezing your nipples.

You try as hard as you can to break free and struggle against your bonds, but it's clear you have no way to escape. She laughs at your helplessness. She snaps her fingers, and a screen automatically drops down from the ceiling. On it you see a beautiful young blond woman strapped to a table just like you are. She is naked except for a device clamped to her pussy, most likely a version designed for different genitals. You recognize her as a scientist you worked with who had recently gone missing.

"Your colleague helped us design this device, but now I no longer have any use for her. You on the other hand, will have plenty of uses for us. You will be edged, and she will orgasm to death. I'm going to leave you here and let the devices do their work. After the scientist is disposed of, you will be given a choice. Join us or die. In the meantime, enjoy." She turns and walks out the door, revealing a thick, round ass as she walks away.

You feel fear, anticipation, and arousal all at once. You squirm in your restraints and try to wriggle out of the device but it's useless. You hear loud mechanical sounds as the device activates. You additionally don't feel much, almost like a light vibration. Your cock has been soft, but the stirrings of arousal and anticipation were starting to affect you as you felt your helplessness. You see the scientist on the screen start to struggle on your screen, as she realizes what is happening with her device.

Suddenly the intensity ramps up and your cock grows rock hard. The electricity is stimulating your nipples, almost caressing them. You feel a warm, almost moist sensation on your cock. It feels as good as sex, and you can't tell if it feels more like a wet clitoris or a pair of hot lips sucking on your shaft. You can feel stimulation in your prostate vibrating and filling you with arousal and pleasure. You can barely pay attention to anything, not even registering the scientist shaking with pleasure on the screen in front of you. You can barely control your muscles, not noticing yourself spasming against the straps holding you down. You can feel the beginnings of an orgasm approaching, you crave a release, you don't care what it takes, all you want to do is cum.

It gets closer and closer, and you bite your lip in anticipation of an orgasm, but then everything stops. The machine grows silent, and all the pleasure stops. You hear the scientist moan through the screen as her device ramps up its intensity but yours just clings stubbornly to your cock. You thrash against the restraints desperate to touch yourself. You can't move. You just watch the scientist in front of you, the sight arousing you despite knowing what will happen. The fear starts to kick in, and the arousal starts to dissipate.

The machine sense this and kicks back into action, sending pulses into your cock and bringing you back to the brink of an orgasm. You realize just how helpless you are.

"Help me!" The scientist yells through the screen.

You want to respond but you know she won't hear you. The machines just go on and on, pleasuring you and the scientist. You're not sure how long the torture's gone on for. It could have been minutes, or it could have been hours. You're not sure when she orgasmed but you glance at the screen and see the scientist is slumped over, and only your machine is making any sound. You would struggle and thrash more, but you have almost no energy left. You start to drift out of consciousness, but you feel a sudden jolt of pain from an electric shock. The machine is keeping you awake.

You're at your breaking point when the guards walk into your room and deactivate the machine. You barely notice as they pull the table you're attached to onto a cart and wheel you through the facility. You can faintly hear screams of pleasure from other rooms as they bring you into an office. The boss who subjected you to your torture is sitting at her desk. She stands up, walking over to you and unclipping the device from your panties, which are completely soaked and on the verge of falling apart.

"I see you've had the chance to enjoy our hospitality. But the time has come to make your choice. What will it be?" She asks.

Ending 1 (Accepting her offer):

You can barely mumble out the words.

"Yes. I'll join you. Please just let me cum." You plead.

She is pleased with this.

"Of course, my dear. Welcome to our side." She pushes a button on her desk and the straps holding you to the table release you.

You can barely stand, weak from all the pleasure.

"Now strip." She commands.

You weakly pull the panties off and stand in her office naked. Your cock is still hard, and small drops of precum drip from it.

"Good." She briefly pauses. "We're going to need your DNA now. Come with me."

She leads you out of the office. You reach a white room with nothing but a chair. You are staggering, the erection fading.

"Sit." She orders.

You step into the chair, expecting cold metal. To your surprise, it is warm and padded. It feels like velvet against your naked body. Straps emerge to bind your hands and feet to the chair. You glance at your new master puzzled.

"Just standard procedure. Now hold still, we're going to need you to cum for us."

She produces what looks like a tube and approaches you.

She strokes your cock, clearly enjoying how hard it is and inserts it into the device. You feel the sucking sensation and shiver with pleasure. It sucks away at your cock, causing you to moan. Your look down at your new master. Her bodysuit is low cut, revealing her large breasts, and she clearly enjoys pleasuring you. Almost within minutes, you can feel the orgasm approaching, the machine is clearly designed with efficiency in mind. You briefly lose control as you cum. Large amounts of semen shoot from your cock. You gasp, watching your cock as it shoots loads into the device. Your master keeps the device on you for a while, making sure you're drained dry.