tagTransgender & CrossdressersThe Challenge - Wear a Thong

The Challenge - Wear a Thong


There is something deliciously naughty about a boy wearing women's thong panties for a day, after all, the first time you wear a thong all day long, especially on a week day, you will be going about your normal routine. Whether it be to class, to work, or whatever you normally do, you will have it on all day, even when you're not fully sexually aroused. Why do I say when you're not fully sexually aroused, that is simple because you will constantly be reminded that you are dipping your toes in the taboo and for a sissy that alone is quite exciting?

You might be reading this and say that will never happen to me, I only wear panties to masturbate and only until I get off. You might also be thinking, I would never wear them to work, and you may be right. Or, maybe the need to wear your thong all day, to class, or to work, may not have been awaken inside of you yet. My money is on the later. If and when the desire to wear your thong all day finally over takes you, and you give in and do it, I honestly believe you will be hooked.

Honestly, if I were you, I would plan my first day wearing my thong, so that there was at the very least a possibility of some alone time, when you get home from class or work. There is nothing worse than coming home all excited, because you've successfully done it, and finding your roommate has plans for you. Especially, when all you want to do is celebrate a successful and thrilling new adventure, with the palm of your hand in the privacy of your own place. Don't think, I don't understand at all, what your about and what your motivations are either.

I am quite sure that you fascinated about wearing panties, and masturbated many times trying to get the courage to go forward. In fact, the thought of doing it, has been building up inside of you like a pressure cooker and now you can't control it. Sure, you may jerk yourself off, and the desire may calm down, but after so many cycles, you either want the desire to go away, or leave you alone, but it won't, it keeps coming back, stronger and stronger, until you just give in and surrender. Surrendering to your desire and going for it, is the only way to calm the desire.

Still you're unsure whether you can actually proceed and do it, so you start searching for stories about guys wearing panties, but it's all so eroticized. No one in any of these stories lose their job, if their caught, and many times the outcome is extremely erotic. At the end of the story, no one gets hurt, at least not too bad, although they usually don't end with the panty boy or sissy riding off into the sunset with a beautiful woman and living happily ever after, either. You start to rationalize, that it wouldn't be so bad, even if something goes awry and you do get caught. Which by the way, is actually quite accurate, no one is going to care that you wear panties. Sure they might get a laugh over it, but that is about it.

You're a good dresser and you keep the back of your shirt tucked in anyway, and you're getting brave; you keep thinking about it. You're so close to going for it and trying it. Maybe you wake up extremely horny one day and that is just enough to push you over the edge. Perhaps you over sleep, and there isn't time to masturbate, and relieve the pressure that has built inside of you, or perhaps you did masturbate, but the desire didn't go away, and you still can't stop yourself. You put your thong on, thinking maybe, if you just wear it to brush your teeth and eat breakfast, that will be enough! And maybe, that is enough the first couple times you get this far, and you take your thong off before dressing for the day. This scenario plays out several mornings and you think you're the master of your own domain, and can stop yourself from going too far.

But one day, that is simply not enough, you're scared because you realize that there is a good chance, that this day, will be the one day, that you can't get yourself to take it off. Perhaps you think, I have a few extra minutes, I'll put on my pants, my jeans, or my slacks and see how it feels. The problem is the material of your pants rubbing across the cheeks of your ass as you move about, and it feels so incredibly good, and you think of everything you've read. All those articles that have said, the desire to wear your thong to work, won't ever go away. You're tempted to try it, after all it's only one day and if your careful, no one will know.

You don't know why the temptation is so strong that day, but it is, and all you can think about is doing it, instead of why. Perhaps you feel a little under the weather from the drinks you had the night before; perhaps it's that relationship that isn't going the way you want; perhaps it's the head cold that has been bothering you; or possibly it's that aching in your knee that just won't go away. Whatever the reason, your defenses are down, and your feeling weaker than normal, and you simply give in. You walk out the door, get into your car, or get on the bus, and you go wearing your thong. Congratulations, if you've gotten here, you're about to have the most amazing time.

Your constantly on edge making sure the back of your shirt is tucked in, and as you do so you constantly feel for the waist of your thong as you tuck in your shirt over and over. Your infatuated with it, and how it feels. Your scared, but you feel so alive. You stop for coffee, or maybe gas. People have seen you and none of them notice you're wearing a thong. How could they after all you have pants on. You begin to realize you can do it and get through the day, but you know what you're doing and it is a distraction all day. Early in the morning you figure out that when your engaged in your work or talking with others, that you can push your thong out of your mind for a while and it really is only a distraction when you have time to let your mind wander. On break, all you think about is your thong, as you stare into space, and someone asks you, if your all right, because you seem distracted. You don't dare tell them, where your mind is going or has been.

By mid-afternoon you are thinking about what you are going to do when you get yourself alone. At this point if you masturbate wearing a condom, into a baggie, use a sex toy, look at magazines, you will be wondering if you have what you need when you get home. Perhaps you do all of your perverted shopping miles away from where you work, and you realize that you need condoms, lube, a new toy, or a new magazine. The desire to masturbate the moment you get home is over powering, and you start to consider taking the risk of stopping at the drug store, gas station, or local sex shop that is close to home or work. That's it, you'll just hope no one recognizes you. Your panties have you so turned on that your willing to take a risk that you would have avoided before. You are unable to comprehend what your thong is doing to you, you just know, that you have to pump some of that testosterone, out of your body.

Continuing To Wear Thongs All Day

You've done it once and you've gotten away with it, but now you have a new dilemma. You want to do it again, and then again and again. You face the same fear and trepidation but with a little confidence. You've decided to do it again, only this time, you're not so nervous and you start to notice the tiny but distinct differences between male underwear and your thong. You start to compile a list in your mind of all your likes and preferences. The list grows over time as you do it more and more. Your still scared as hell that someone will find out, but you can't stop and the novelty of it wears off.

When you can manage to convince yourself to wear boy underwear again, you swear your done wearing thongs, but you only start the inevitable buildup of temptation to wear your thong again. You push away your desires for days and then weeks, but finally the temptation is too much, and you can't sleep, you lay awake thinking about doing it again. You finally get to sleep, but you awaken early, with more pent up sexual energy than you can manage to dispel from your body.

Simply masturbating it away would take days. You wonder is today the day, I should just give in and do it again? After all, for the past several days you not only haven't been able to concentrate at work, but your body is so tight and sore. You have to run an errand at work and you'll be alone in a car, how much worse can it get. You almost fear being alone, as you know your mind is going straight to thoughts of wearing your thong. You drive across town trying to act as nothing is bothering you, but your heart has convinced your body, that it wants what it wants, regardless of your understanding of the issue. Your heart, and your body gang up on your mind, your mind is almost powerless to stop them. You gave into impulse once and you got hooked, but somehow you got free and thought you were miraculously cured.

But on this day, you realize your thong is calling for you, and you are much weaker than you were the first time, that you were over powered by temptation. Perhaps you somehow manage to continue to try to deny your desires, but they only get stronger. You can't take it anymore, you want to get back to normal, and you think to yourself fine, perhaps if I wear my thong to work again, I'll be able to get back to my old self, and I'll finally be able to concentrate on my work and life again, and you give in and you wear your thong again. Unfortunately for you this is just a delusion; the feelings and desires to wear your thong to work are multiplying and will become a frequent visitor. The more often they visit and have their way, the more often they will visit and the easier it will become for you to let your desire have it's way.

You wear your thong to work more and more. Eventually you seek out more thongs and go shopping again. You become more accustom to women helping you in the lingerie section, you may even give up trying to deceive them and finally you admit your shopping for yourself. It's really not a big deal to the women that work there and you begin to understand what the stakes are. You grow more comfortable being in the lingerie section. You are no longer afraid to pick up a thong and look at it. Although you still take a pass through the store, just to make sure that no one you know is in the store, you begin to get accustom to other shoppers especially girls seeing you holding your selections as you browse.

Your taste branches out and now you're buying every color, even pink and hot pink, even though it increases the chances of getting caught. Even though you know that if just the very edge of your pink thong shows it will be impossible to miss, you begin wearing them because you enjoy taking the risk. You also start to buy thongs made out of different material, and you even start to prefer thongs with lace edges which will be even harder to hide or explain away. Your spending a lot of time stopping at different stores buying panties, sure you have your favorites and your favorite sales associates that tease you, and they have even asked if your shopping for yourself. In fact, it felt so good to admit it your now hooked on the thrill of girls knowing your secret.

As you venture into new stores your eyes and ears are open and you realize that the sales associates are talking about you, you hear them giggle, or mention that you are most likely looking for something for yourself. It excites you that they already have you pegged. Your even more excited as one of them offers you help. You begin to realize you're no longer shopping to acquire new thongs, you're actually shopping to interact with the sales associates. You enjoy women finding out your secret and you find it sexually arousing. You begin to think about the sales associates having sex when you masturbate, but as they know you are a panty boi or sissy, you realize that you are inadequate for such a task in their eyes. So you begin to masturbate thinking about them with their boyfriends or husbands.

Eventually you begin to wonder what it would be like to have a woman see you in panties. And, when something is wrong with your health, and you're going to the doctor, you can't get in at your own general practitioner so you are going to have to go to the walk-in clinic. You've dated or scored with a couple of nurses in the past, and they were extremely kinky girls, and you wonder what they would say at the doctor's office if they only knew. You contemplate if you should wear your thong, but you don't feel good, and so you're not so excited, so you go in the last pair of boy underwear, that you saved should you need them. Sure, enough you need to get a shot, and they insist on giving it to you in your butt. The nurse charged with giving you the shot is good looking and you are suddenly kicking yourself in the ass for not wearing your thong.

You swear to yourself that you won't make that mistake again, and you wear your thong to the doctor every time since. Unfortunately, the need to have a shot doesn't come and you just get in the habit of wearing your thong, as if nothing is going to happen anyway. Eventually, you go to your general practitioner with some illness or infection, and your told you need a shot. Damn you think to yourself, this was supposed to happen at the walk-in clinic where they don't know me, not here. Your horrified as mentally, you are unprepared for what is about to happen to you. You hope to get your fingers in the waist band of your thong and pull it down with your pants, so that she doesn't see it. You have no idea if your successful, as you are facing the bed and the nurse is standing behind you. Nothing is said, and she administers the shot. You're unsure if you successfully at hid your secret, but your hopeful, as she leaves and shuts the door. Suddenly you hear laughter at the nurse's station and the realization that you failed sets in. You hear all their voices, even the cute nurse is laughing. When you go to leave they all wave goodbye and smile at you, which is out of the norm. Usually they pay no attention to you, and barely look at you, but now things are different.

You retreat and go home, unhappy because you failed in so many ways. It feels like the world is going to end, and your life is over, but you awake the next day and your still there, and you feel a little better. You reflect on your experience, in one way you got exactly what you wanted. But, you envisioned it happening at the walk-in clinic, not at your local doctor's office, where they all know you. And, now they all know your secret, and you wish you could do it over. Especially since, they all found out your secret anyway, your disappointed that you even tried to hide your thong. Why didn't you just drop your drawers and bend over. Honestly, there wasn't any need to pull down your thong as your butt cheeks were already exposed. If only you hadn't tried hiding it and your embarrassment, perhaps then she would have commented on how cute your thong was. You become fixated on why she didn't make a comment.

Eventually, you masturbate thinking about all of it. While your masturbating, you realize, it wasn't so bad, as it all unfolded unscripted and naturally. You got the nurses natural reaction and that was more important and exciting than any script or plan. You begin to embrace that your secret is entrusted with the staff of your doctor's office. As you return for more and more visits you begin to realize that it's really not so bad. The nurses are always glad to see you and are much more interested with you. It becomes a relief, that you have nothing to hide from them. After all they are understanding women and they are there to help people.

Now you really have problems

Once you recover from the shock of your doctor's staff all knowing your secret and all works out well, you realize just how good it feels that women know your secret, and you want more. Now you really have problems, especially because it's becoming an addiction. All you know is you want some more women to know your secret. You begin to fantasize and dream up more ways of being seen as a panty boi and a sissy. Right from the start you realize that not only are you dreaming about this now, but you're also scheming and actively planning on carrying through with further exposing yourself. You rationalize that if it felt good to have a few women know your secret that it will feel even better if more know.

The girl that cuts your hair is an obvious target you think. She will be behind you as you sit down in the chair and if your thong just happens to show hopefully she will see it. Your exposure at the doctor's office didn't go quite like you had planned and you want to be sure everything is right with your hairdresser.

You fret and worry, wondering which thong to wear. You wonder should you wear pink, or will that be too much? How about lace? Finally, the day for your hair cut arrives, and you have to make a choice. If you wear simple white, will that be enough to get her attention? Maybe if you leave the tag hanging out the back it will help, you think to yourself. You hope so, and you hope that she mentions your thong.

On your way to the salon you have a little day dream, wondering how it will go. Will she tell her coworkers, and will she tell you, that you've been caught? You get to the salon and she is just as beautiful as you remember. You are so close losing any chance you may have had of getting with her, and you are ready for it to happen. Your penis is half hard and dripping, and you a bundle of nerves as your led to the back.

Your pants have slipped down slightly and normally you'd just naturally pull them up, it takes all the will power you have not to. Where most of the boys look to impress this girl, and get into her pants, you are determined to do the opposite and lose any respect she may have had for your masculinity. You're at the chair, and it's time to put up or shut up. You look in the mirror on the other side of the salon to see your beauty that your so determined to have judge you. You arch your back as much as you dare as you sit, in hopes your t shirt will pull out of your pants and expose your thong to her. You're still looking in the mirror to see where her eyes are. She waiting for you to sit with the cape in her hands, ready to put it around you. She smiles as you sit, and puts the cape on you. You're so frustrated, because you don't know yet if she noticed. It's so uncomfortable sitting there wondering, and not knowing, if she saw, or what she thinks, but you're afraid to ask. So, you sit quietly as she begins to work, wondering and hoping...

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bytaraterry© 1 comments/ 18773 views/ 7 favorites
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by Anonymous

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by Anonymous10/19/17

Been there,love being there!!!!

Reminds me of the thrill of the good feeling in my pants and the thrill,fear,of getting
found out.
I gave my doctors nurse practioner a photo of me as Jackie,and my doctor and a few other people got tomore...

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