My first attempt at a F+M non feminization story, This story contains sex bondage blackmail and crossdressing so if you dont like that sort of stuff just walk away now:)
Helen’s Blackmail-Sex Slave
On a sleepy Tuesday morning nurse Helen returned to her office gasping in shock as she entered “My office has been ransacked, I bet it was that Alex Stone he thinks he owns the place†Helen fumed as she tidied picking up a memory card she was sure Alex had dropped popping it in her computer, Helen was amazed as on the card was video of Alex in drag along with a load other video’s she began to watch “My my what a big cock you have†Helen giggled drooling into her lap.
Helen was 37 with hazel eyes long blonde hair kept in a pony tail and d-cup breasts, Helen has a toned and curvy body gained from exercise and healthy eating, Helen has a devious personality always messing with patients to bring herself joy, Helen is an avid lover of bondage usually tying up teenagers to suck there cocks as she was considered a cum slut by all knew her outside of the collage.
Helen wore a white nurse shirt which buttoned up the front, 3 buttons where usually left undone to show off her marvellous cleavage which sent the students wild, Helen also wore a knee length white skirt white stockings matching lace lingerie and 5 inch white heels, Helen looked less collage nurse and more sexy nurse which made her a favourite of nearly all the male students.
Helen made a call across the collages intercom for Alex who promptly arrived looking smug as he scanned the mess “you called for me nurse big tits, you enjoy the redecoration I did for you†Alex scoffed making more mess before Helen firmly slapped him, “why did you do that bitch!!!!, Im so getting you fired†Alex hissed as he turned to storm out.
“I wouldn’t go just yet, you don’t want to miss the show†Helen giggled as she turned on the computer playing his drag video much to his horror, “Before you think about trashing the computer I made back-ups and if you don’t want them to make it to your classmates you will do as I command†Helen said with a smug look on her face.
Alex was 19 with blue eyes shoulder length black hair and 8in penis when erect, Alex has a not quite small not quite average build with small muscles gained from hitting the gym in his quest to impress people around him, Alex is a shy reclusive usually avoiding intimacy with girls as he becomes aroused which leads to some awkward situations.
“I will do what ever you want just don’t post the video’s please†Alex begged as he began to tidy the room frantically as Helen stared on with delight, “How did she get those videos I have the only co-damn I must have dropped the card†Alex thought as he swept the floor.
“I will come around to yours at 7PM make sure your alone or I will post the videos†Helen hissed ordering him out of the room in a hurry, “I knew he would break easily, he never was good around shame and embarrassment†Helen thought as slid the memory card out of computer and into her pocket.
Alex paced back and forth in his living room as the clock struck 7 shortly there after the doorbell rang and he promptly answered “Hello Helen where all alone my mother is away for a few days†Alex said nervously as Helen was still in her uniform licking her lips.
“Ok this will be simple lose the pants, if you refuse I post the video’s†Helen hissed forcing Alex to strip, Helen slowly rubbed his cock till erect watching the look of horror and disbelief on his face, “For today’s exercise I will give you a blowjob, don’t be alarmed I do this to loads of students who deserve it†Helen giggled sliding his cock into her mouth and slowly began to move her head backwards and forwards.
Alex was scared but extremely aroused as the hottest nurse he had ever seen was sucking him off “This feels so good, but she’s blackmailing me and there’s nothing I can do†Alex thought as he orgasmed shooting his hot cum into her mouth, Helen swallowed and began to suck him off again “How long … will you… be doing this….†Alex asked as he came again and Helen once more swallowed.
Helen sucked Alex’s cock for 2 hours before it went limp “I guess that’s your limit for tonight, but I will be back tomorrow and we will be doing exercise 2†Helen giggled as she left the house and the bewildered teenager, “out of the cocks I’ve sucked his was the best, even his cum tasted divine†Helen thought as she planned for the next meeting.
The next day all Alex could think of was what had happened the night before and how good it felt “That was the most intense pleasure I’ve ever experienced, but a part of me knows it wrong and should stop†Alex thought as he finally plucked up the courage to ask out Nina the girl of his dreams “Hi Nina would you like o go out sometime???†Alex asked nervously as Nina thought long and hard about it.
“Sure id love to go out with you but there’s something you should know, I like to dress men in my cloths and lingerie and tie them up†Nina said looking extremely embarrassed only for Alex to confide in her his love to cross-dress, “Your the first person I have told this and im guessing im the first you have told???†Nina asked receiving a silent nod from Alex before they parted ways.
That night Helen arrived at 7pm ordering Alex to lose the pants as she lifted her skirt to reveal her panty-less crotch “Tonight you will take me up the arse, don’t be gentle I like it rough†Helen giggled as she stroked his cock to erection giving it a quick suck to lube it up before getting on all fours, Alex thrust his cock in Helen ass using her breasts as leverage as he thrust furiously “You seem eager to please, is it because of that slut Nina you asked out†Helen hissed leaning back and clutching his balls tightly.
Helen’s grip tightened as a visible anguish appeared on Alex’s face “Please let go it hurts so much, you didn’t say anything about me dating†Alex pleaded as Helen slowly released her grip going back to her original position as Alex continued to thrust his cock into her ass orgasming hard, “Look Nina is the first girl I’ve been close to without becoming aroused straight away, she may be the one for me†Alex grunted as the strain of pounding Helen’s ass began to show.
“I guess you can have your fun with Nina but it better not interfere with our fun†Helen hissed as ordered Alex to lay on the floor as she continued to ram his cock up her ass not once removing it, “once your mother returns we will be meeting at my place understood†Helen said sternly as Alex orgasmed again shooting more hot cum inside her ass.
Helen rode Alex’s cock for 3 and-a-half hours before it went limp “My my you lasted longer this time im impressed, now open wide I need somewhere to collect your cum but don’t swallow†Helen said as she hovered her ass over his mouth letting the cum gush out to Alex’s disgust, Alex’s mouth was now filled with his own cum as Helen locked lipped sucking the cum out slowly probing his mouth with her tongue “Utterly divine as always, I will see you in 2 day at my place you know where it is†Helen giggled licking a few droplets of cum off Alex’s face tidying herself up and leaving.
Alex walked to Helens dreading his next exercise as his cock still ached and he was more conflicted about what he was doing “Me and Nina have a great relationship but Helen gives me something Nina cant, but I see I future with Nina†Alex thought as he arrived at Helen’s knocking on her door nervously.
Helen greeted him with her big tits hanging out turning him bright red as his cock began to throb “Come inside and strip, I will be kinder on your cock today†Helen giggled closing the door before laying on her back on the floor, Alex stood nude before Helen awaiting further instructions “I want you to sit on my stomach and place your cock between my breasts, first thought I must restrain your hands so you so don’t touch my breasts†Helen said producing a pair of silver hand-cuffs cuffing Alex’s hands behind his back with no protest from him.
Helen pressed his breasts against Alex’s throbbing cock and began rub them back and forth giving him a tit-wank “This feels…. Nice!!!!!†Alex gasped as her orgasmed spraying hot cum over Helen’s face and chest, Helen ran to fingers across her chest collecting the cum swallowing it swiftly before continuing the tit wank “I cant keep doing this it will destroy me and Nina, once this session is over im ending it†Alex thought as he orgasmed again this time Helen was ready placing the tip of his cock in her mouth to collect her reward.
After a few hours Alex’s cock once again went limp “My my its seems you preferred taking me up the arse to a blowjob or tit-wank†Helen giggled placing his cock in her mouth to suck out the last drips of cum before standing him up, “Tomorrow you will be here bright and early at 9AM, we will be moving onto exercise 4 so don’t be late†Helen hissed as Alex wrestled with his conscience as he awaited his wrists to be released.
“Im done with this I wont be back tomorrow, Im going to reveal my secret to the school†Alex said confidently as Helen grumbled angrily as she walked upstairs to get the keys, “Helen seems to have taken it better than I had hoped, I guess she see’s how much I love ni-MMMMPPPHHH!!!!†Alex screamed as his cuffed hand where pulled up strappado style and a chloroform rag was forced over his mouth.
“Did you honestly think I would let you after I gave myself to you†Helen hissed as Alex thrashed wildly but he was unable to break form Helen’s grip and slowly slumped unconscious, Helen threw Alex’s body over her shoulder and carried him to her bedroom where he was tied spread-eagle on the bed “No-one leaves me until I say so, you will make a great cum slave†Helen giggled licking her lips as prepared some toys.
Alex slowly regained consciousness a few hours after he was subdued meeting Helen’s gaze “You freaking bitch untie me, my mother will know something is wrong†Alex hissed as Helen slowly climbed up the bed, Alex continued to protest spitting at Helen forcing her to pull a ball-gag from the top bedside draw “Please don’t gag me I wont scre-MMMPPPHH!!!†Alex pleaded as the dirty ball-gag was forced into his mouth silencing him completely.
Helen moved back down to Alex’s waist slowly rubbing his cock to erection as he thrashed and tried to spit the gag out “Calm down your bonds are inescapable and I know your gag tastes awful but it is covered in the drool and cum of my previous victims†Helen giggled as she lifted her skirt to reveal her bare crotch as Alex tried doubly hard to push his gag out, “The gag wont be leaving your mouth so stop trying, just relax and enjoy my warm pussy embracing your throbbing cock†Helen said in an intimidating voice as she slid onto his cock much to his protests.
Alex was fucked for 5 hours all the while protesting and pleading through his gag before Helen grew tired “Im going to get some sleep and savour the cum inside me†Helen groaned wiping a handful of his and her combined cum over his face and gag before leaving, Helen savoured her prize before making a few calls “This is perfect no-one notices him at school and his mother thinks he’s moved out, he’s all mine forever†Helen Squealed as she began to plan his new life.
The next morning Helen fed Alex and let him use the bathroom before retying him to the bed “Im going to by some new toys for us to use later†Helen said in a ominous voice before pulling a hood over his head causing him to thrash and scream. “Don’t do anything to strenuous while im away†Helen mocked as she left him to struggle alone in the dark with no indication of how long he would be there.
Alex struggled for what seemed like forever giving up because his wrists and ankles grew sore and his mouth ached as the ball-gag kept his mouth propped open “Someone will know im missing im sure of it, if not Nina then mother will†Alex thought gaining an erection just thinking about Nina and must to his frustration could do nothing to satisfy his urges, a few seconds later he heard the door open and 2 women talking “I know that voice… its my mother Andrea what is she doing here?? Alex wondered as he screamed into his gag.
Helen removed Alex’s hood as he looked on in disbelief as his mother just smiled “Someone has finally put you in your place, and I cant say I blame them†Andrea hissed grabbing his erect cock digging her sharp nails in causing him to scream in agony, “Me and Helen had a little chat and she own you now, I got 7grand for your worthless ass†Andrea giggled giving him a kiss on the forehead before leaving.
Helen approached Alex holding a bag of new toys tipping them onto the bed “Did you get hard when you heard mummy coming??, I will put that erection to good use in a second but first let me show you your new toys, firstly your cock ring to keep you harder for longer a vibrating butt-plug to keep you stimulated a penis-gag to train you and finally this suction device to milk your cock when im at work†Helen giggled clamping her lips onto his cock and sucking as Alex turned pale with fear at the thought of the items she bought.
Alex orgasmed filling Helen’s mouth but she did not swallow instead she removed his gag and placed his new penis-gag into her mouth covering it in cum swallowing what was left “HELP HELP im being held against my w-MMMPPPHHH!!!!†Alex screamed as Helen shoved the cum covered penis-gag deep into his mouth just short of causing him to gag, Helen was angry at his attempt to signal help grabbing the medium sized butt-plug forcing it into his delicate anus with out lube making him scream in agony.
Helen watched as his cock went limp from the pain “I have another surprise for you, im going to give you a makeover†Helen giggled as she coated his legs crotch armpits and chest in wax strips, Helen began to rip off the wax strips one after the other making Alex thrash and scream “Well only your pubic hair to go, it shouldn’t hurt that much if I pull the right way†Helen giggled ripping the 2 strips off in different directions causing Alex to blackout from the pain.
When Alex awoke he was now tied strappado with his ankles tied together and was shocked to see he was wearing women’s clothing “What the hell has she done to me†Alex thought as he groaned into penis-gag as he tried to get free from his bonds, after a few minutes Helen returned holding a camera and a laptop showing him a website kidnapped trannies dominated sending a shiver down his spine as he knew what the site was “Oh god she’s going to stream herself sexually dominating me to a bunch of freaks and perverts†Alex thought struggling even harder than before.
Alex was now wearing a tight pink dress with a slit down the left side exposing the thigh, Alex also wore pink stocking matching Pink lace lingerie and pink 6 inch stiletto heels, Alex’s bra was stuffed with gel packs to make it seem like he had breasts, Alex’s face was coated in make-up and his hair tied in tied in a ponytail, in his present state even the most observant would assume he was a girl.
Helen stripped nude before starting the web feed which had over 500 viewers and rising “I knew you where a dirty slut Alex or should I say Alexis, but I didn’t imagine you cross dressed†Helen giggled acting for the camera as she slid his panties down revealing his cock-ringed limp cock, Helen began to stroke and lick his cock making it erect causing Alex to yelp as the cock-ring squeezed his cock tightly “My my what an impressive cock you have, I hope you don’t mind if I suck it†Helen scoffed reaching round and switching the butt-plug on sending a jolt of pleasure through Alex.
Alex could only blush as Helen began to suck his cock for her viewers to see sending waves or pain and pleasure through his body as he tried to pull away “Don’t resist or I will have to get rough†Helen hissed as Alex shot his load into her mouth, Helen showed her audience the cum before swallowing and gasping as the viewer count passed 6000 “Your extremely popular, did I forget to mention I sent the link to every pupil in the collage†Helen giggled as she lowered his strappado laying him flat on his back.
“Everyone in the collage is watching!!, I can never show my face in public again not that this psycho bitch is ever going to release me†Alex thought as Helen mounted his cock with her warm pussy sending an even greater wave of pain thought his body nearly bucking her off, Alex’s screamed into his gag as each second brought greater pain “The cock-ring hurts so much im going to blackout at this rate†Alex thought pleading through his gag for mercy.
Alex orgasmed hard filling Helen with cum “How about I share your glorious cum with you†Helen giggled removing his penis-gag forcing her pussy over his mouth forcing him to clean it before forcing the gag back in, Helen turned around lowering her anus towards his cock as he pleaded and protested which had little effect as she forced his cock inside her “Don’t be such a girl or I will do this again tomorrow†Helen hissed as Alex screamed in pain with each rub of his cock.
Alex knew what was to follow as he unleashed a spray of hot cum into her ass “You get to clean up again slut†Helen giggled removing his gag and forcing him to clean her ass for the world to see forcing the gag back in when he was done, “Where nearly finished just 2 more little games†Helen said as she forcefully removed his butt-plug and grabbed a strap-on from the closet sliding it on.
Alex screamed and thrashed as Helen approached reaching down yanking his cock-ring off before flipping him over “This will only hurt for a few seconds and as a sign of mercy I removed your cock-ring†Helen said forcing the strap-on into his tight ass making him scream in agony, after 10 minutes of thrusting Alex no longer noticed the pain and accept what Helen was doing “Don’t get to comfy im done with your ass, now im going to let you suck my strap-on†Helen giggled as Alex’s eyes widened with fear.
Helen checked the site as another 4000 viewers joined in commenting and offering large sums of money for Alex before removing his gag “Please don’t put tha-MMMPPPHHH!!!!†Alex pleaded as the strap-on was forced into his mouth and down his throat causing him to gag and slowly blackout only for Helen to remove the strap-on, Helen did this for 30 minutes before chloroforming Alex and ending her show checking all the comments.
Helen was drawn to an offer of 200000 for Alex and decided to sell contacting the buyer and arranging a meeting for early next morning “There are plenty more cocks I can suck at that collage though I will miss you†Helen sighed as she untied him rebinding him to the bed giving him a shot of Viagra, Helen waited for his cock to harden and attached the suction pump she had bought “I might as well collect some of your delicious cum before leave†Helen giggled as the pump got to work.
Alex awoke the following morning tightly hogtied still dressed as woman as Helen entered the room grinning “You have a new master his name is peter and he will be here shortly†Helen said coldly as Alex struggled to take it all in, Helen tidied up Alex’s make-up and made sure everything was as requested before running down stairs to answer the door.
Helen opened the door and greeted peter “Hi he’s upstairs do you have the money??†Helen asked but was shocked to have a gun pointed at her as she was ordered to strip and cuff her hands behind her back, “What the hell are you do-MMMPPPHH!!!†Helen hissed as a penis-gag was forced into mouth before she was dragged to the trunk of peter’s car kicking and screaming and chloroformed before her ankles where tied.
Peter then ran upstairs to Helen’s room where Alex lay struggling furiously “Your just as requested, you will be my wife’s sex slave but don’t worry Im taking Helen as my slave†Peter said giving him something to feel good about before he was chloroformed and dropped into the trunk with Helen, “Jessica will be pleased with her new toy and Helen will make a nice addition to my sex slave collection†Peter thought as he drove out of Helen’s driveway taking them to there new life as sex slaves.