Its was a typical day in the ac business, all the guys joking around and making the day go by. Today, was no different from any other, but today Kyles life would change forever. At lunch all the guys were sitting around, shooting the bull, eating and betting on dumb things. Kyle decided today he would join in. The guys were betting on who would get a service call first. Carlos said it would be him, since he deals with a lot of restaurants and stores. Scott knew it would be him," I have nothing but office buildings!" Kyle sat there pondering, reviewing contracts and site he took care of. Finally Kyle said," i have processing plants and something is always failing." The bickering went back and fourth a while, finally Carlos said,"lets make it interesting, the first texh to get a service call, has to return to work tomorrow wearing a high waisted g string." Everyone laughs, and agrees. Lunch finshes and the guys go back to work. Few hours later, Kyles phone rings, its Lyndsay from dispatch. Kyles stomach dropped, the guys began laughing and nagging on him. Lyndsay asked what was going on, and Kyle explained. She begins to laugh and tell Kyle that it should be an interesting day tomorrow. Kyle leaves the site, stomach in knots, but also wondering how it would feel in a g string working.
Later that evening Kyle receives another phone call from Lyndsay, she asks if he would come over to her house and fix her ac. Kyle figures why not, hes out and about plus Lyndsay is nice to look at. Lyndsay is in her late 20s, about 5 ft 6in, a chest that men stare at, with a figure of a model. She has long strawberry blonde hair and always wearing sun dresses or clothes to the office that enhance her curves and figure. Kyle arrives, Lyndsay answers the door with a glass of wine in her hand, and a short skirt, high heels, and a lacey top on. She invites Kyle in, and lets him go to work. Kyle notices she her friend on the couch eyeballing him and giggling with Lyndsay. Kyle smirks and thinks she is into him, he thinks to himself. I'm just an average guy, 6ft, nothing special, but women do love my eyes. He finishes his work, and goes to tell Lyndsay what he found. She and her friend invite him to sit and have some wine, and snacks. Kyle figures why not, been a long day, some snacks, wine and beautiful women, what else could a single man ask for. Lyndsay and her friend Katie, scoot closer and begin flirting with Kyle. Kyle is enjoying this, like any man would. About an hour goes by, and Lyndsay notices, the wine bottle empty, she gets up and goes to the kitchen. Katie and Kyle continue conversations until Lyndsay shouts in the distance," Kyle can you come help me, I cant get the bottle open," Kyle hops up from the couch, feeling a little tipsy and with a smirk. He knows this is how most of the porn he watches starts. As he walks into the kitchen, Lyndsay is standing there in a lace bra and thong. Kyle stops dead in his tracks, and looks her over. "Oh Kyle stop it, you've seen women like this before." Lyndsay says bashfully. Kyle tell Lyndsay, "only in movies," with a chuckle. Lyndsay then turns around and grabs a bright pink g string with a see through crotch on it. "About your bet you lost, I picked this up for you, and since Im not in the field, I want to see it on you...we both want to see it on you." Kyles face turns red and he is in shock, with a slight embarrassment.
"You both want to see me in this, the bet was to wear it under my clothes tomorrow, I...I.."
Lyndsay stops him there," listen Kyle, I bought it for you, and I want to see you in it, just this and only this. There is a bathroom down the hall, I left a razor and some shaving cream just incase you want to clean up before coming back out in this cute g string." Kyle gives in, figures what the hell, maybe he will get lucky. He goes down the hall, notices he needs to trim up anyways. A few mintues later he walks out, both Lyndsay and Katie are in their panties and bra, sipping on wine. They see him, and immediately are in awe. Lyndsay snaps a quick picture, " now I can see it over again" Kyle is frustrated, " why would you take a picture!"
Katie speaks up,"nevermind the picture come sit back down and have more wine"
Kyle reluctantly gives in, figures atleast he can hide himself with a pillow and let them talk while he enjoys them barely dressed. Lyndsay hands him a glass of wine, Katie begins to rub his leg while Lyndsay rubs her fingers through his hair. Kyle thinks to himself," this is worth it right now", and goes to drinking. The ladies get a little more touchy feely and begin to kiss him and each other. Kyle is watching in enjoyment, and is in awe. As he is watching with a pillow over his lap, he starts getting dizzy and sleepy. He doesnt know why, he is trying to stay awake, but his eyes get heavier and heavier. He cant fight it anymore and passes out.
Kyle hears giggling and the sound of a camera shuttering, slowly he opens his eyes. Tries to move but cant, tries to speak and no words come out. As Kyle begins to wake up more he finds himself, draped over the coffee table, arms out, hand tied down, on his knees. He goes to move his legs, and cant. He tries to say something and Lyndsay kneels down infront of him,"Ob Kyle, I have you strapped down on your knees, and gagged, dont worry i left your cute g string on. Since your awake and aware now, I have something to say. Ive always thought you were cute, but something was off. So i called you over and got you drunk. While you were passed out, I went through your phone and saw your porn history. I didnt know you like sissyfication. Ive always wanted a girl with a natural something extra. Now i have found one. Your dreams will come true, you will finally get to sleep with me, and become Kylie." Kyle muffeld voice, screams, and Kyle wants to say something. "Do you want to say something? If i remove the gag are you going to scream?" Lyndsay asks. Kyle shake his head no, and Lyndsay removes the gag.
"Why,why me? What are you going to do if i refuse?" Kyle asks.
"If you say no your free to go, but I have pictures of this and will share them with any girl you might date, besides, your hard and i can see it through the g string, which tells me your not going to say no and you want this, is this what you want? Do you want to be my sexy sissy, be able to please me, and let your inner girl out?
Kyle thinks for a few," yes, but what about my career?" Kyle says.
"Oh not to worry, this will take time but I will ask for an assistant and when I do, Kylie will be hired" explains Lyndsay with a giggle. "Now we have to start training you to be more lady like, we need to get that ass trained to take a real man, you didnt think that I was going to keep you to myself, did you? Well I am, but over time your man hood will shrink and we both will need a man to take care of us. Besides you wanted to be a sissy and this is what sissy life is."
Kyle is lost, wondering if he regretted his decision. Wondering if hed rather go through life, lonely then as a sissy.
"Im going to ask once more before i put this gag back in, are you sure this is what you want? After tonight Kyle is no more and Kylie will be transformed. You will learn to be just like me, and will get you your own clothes and make up, some breast implants, grow your hair and nails, and you wont ever want to play with yourself again. So are you sure this is what you want?"
Kyle thinks about all the time he has watched porn and wondered about being a sissy. All the enjoyment from the porn, the times he got off to it, wishing it was him. Kyle agrees and looks up at Lyndsay.
"From now on its yes my dear, and thank you dear, you need to tell say,"Lyndsay make me your sissy girlfriend ""
Kyle swallows and repeats," Lyndsay, will you make me your sissy girlfriend?"
"Well of course honey, now lets put this gag back in, i have one more thing in the freezer." Lyndsay puts the gag back in, and rushes off to the kitchen. She comes back with a frozen chasity cage, that is small and has no shaft area. Lyndsay reaches behind Kyle and he immediately tenses up.
"Dont worry, you'll get use to it, and you'll still be able to cum, just not in ways your use to, now its the sissy way." , she explains.
Lyndsay holds it against him and he begins to shirink from the cold. Kyle can feel the cold on his parts and Lyndsay putting him in it. He hears a key grinding, its Lyndsay pulling the key out of the lock.
"Now that your locked away, and your already on your knees, I think its time to start training that tight booty hole" Kyle notices a inflatable plug and a bottle of lube. Lyndsay reaches for it, lubes him and he feels her insert it. She airs it up and Kyle begins to moan.
"Oh does Kylie enjoy this?" She asks, and kyle nods.
"Good, cause it is staying there and Im going to leave you here with a vibrator placed at your locked self, and leave it on till you stop cumming."
Lyndsay walks away and returns with a wand and a strap. She attaches it places it against the chasity, and straps it to Kyle. Turns it on high, and sits in front of him.
Kyle begins to feel the vibrations, making him squirm and shake, he starts moaning and and clenching his feet. Few minutes go by and Kyle can feel his hot cum oozing down his leg, his eyes rolling back, moaning from ejaculation.
"Oh good girl, thats one! Now we have to keep going till your balls look like little marbles. I cant have your in thongs with your balls hanging out the side."
Kyle is straped down and laying there, listening, feeling the pleasure, thinking to himself,"oh my god, ive wanted this for so long...", he can feel him self getting ready to orgasism again. His toes curl, head trying to lean back, and he begins to moan even loader.
"Thats two!" Lyndsay shouts.
Kyle starts sgaking from enjoyment, and pleasure, he is beginning to feel weak and tired but doesnt want it to stop. Kyle feels his eyes getting heavy, and just lets them shut.
YOU ARE READING
Life of a sissy
FantasyA typical man, with dark secrets is transformed into his true desire. Transformed by woman he was lusting after. He becomes she and transforms into the woman of her dreams.
