It Isn’t Easy Being a Panty Boy


It Isn’t Easy Being a Panty BoyThis is another fantasy piece with bits of my past in it (no I won’t tell which parts). Hope you enjoy, this is a FETISH story about cross dressing in panties so if that is not for you keep searching.“It isn’t easy being a panty boy,” I thought to myself as Ann, my coworker in my office cube said, “are you wearing blue silky panties Larry?” I immediately realized my shirt had pulled out of my trousers as I bent to add paper to the printer. I didn’t answer her question but I am sure my red face spoke volumes as she took a phone call and I hastily tucked my shirt in while fussing with the printer.Ann’s phone beeped and she grabbed the call and began working on a problem with a customer offering me a diversion for the moment. After Ann had gotten off the phone I heard her chair squeak as she turned my way, “Well?” she said and waited. I didn’t think my face could get any redder, but it did. It was like I was having a pre-menopausal hot flash.” I tried to ignore her as if she was speaking to someone else.Ann rolled her chair across the plastic floor mat and was beside me as I pounded on my keyboard. Then I felt it, she was tugging at my panties. In my haste to tuck my shirt in I had tucked it inside the panties instead of my trousers. “I thought so,” she said, “size 8, but I can’t read the manufacturer. But they are very silky, you have excellent taste in panties,” she said and not in a hushed tone.I swiveled my chair and our eyes met. I had no idea what to say and I felt my cock stiffen in my panties with the anticipation that for the first time in my life a woman might just accept the fact that a man can wear panties without being gay and without wanting to be a woman. Ann was setting on the edge of her chair with her skirt half way up her thighs. I knew I should not look down, but I did.She was wearing a very light natural tone panty hose and they had a matt finish that only comes from a high quality hose. She looked around and then casually parted her legs and lifted the edge of her skirt, “mine are minty green,” she said as I caught a glimpse of the top of her panties through the pantyhose. Her thighs were still close enough together so that I couldn’t see the green panties that covered her crotch, which would have probably caused an involuntary ejaculation on my part.And then she turned back to her computer and said nothing more. “What the FUCK,” I screamed in my head, “What the actual fuck was that?” If what just happened was viewed by anyone in the huge office we worked in would have us both fired and I probably would have been listed on some perv list. Yet my cock begged me for more. “Who made the panties, what was the color name, do you have more of that style, are they nylon, cotton, or some blend?” I had a million questions, none of which could be answered by that brief glance and the fact that in this PC world anything I would say would not go down well.So at my lunch break I tore out of the office and decided to get a coffee and try to divert my mind from the office scene and the obvious fact that Ann now had knowledge of my panty fetish. And it seemed that Ann was somewhat provocative and that in itself could easily have a great cost in the office. As much as I wanted to pursue the subject of panties with her in the hopes she would accept my fetish as acceptable behavior I had been disappointed so many times with women that seemed to accept it and then left me flat feeling like some sort of pervert.Now at lunch after a very uncomfortable morning the cute waitress set my coffee on the table and gave me a perfectly framed shot of her tits barely hiding under that low cut top. There was no doubt in my mind that this little peek was an enticement for a bigger tip and my cock hardened in my silky panties.She smiled and putting her middle finger on the glass topped table as she looked into my eyes said, “if there is ANYTHING you need you simply need to ask,” and walked away with her cute ass presented perfectly in her skin tight pink spandex shorts that were pulled up between her cheeks in the most provocative way. “If that wasn’t a sexually charged comment nothing was,” I thought.With the steaming cup of coffee on the table and the delicious tart now out of site I was left with my thought of a minute ago. It seemed my mind was constantly filled with thoughts of my panties or the panties worn by others. I had been a panty boy for so long that the actual start of it was but a blurry image in my head. In fact it was a little like that old Polaroid photograph I kept tucked away in my panty drawer of my early panty fetish. I kept it primarily as a reminder of those early days when I thought I had everything figured out.The warm sun was blocked by the table umbrella and I had the same thought, “It isn’t easy being a panty boy.” Today started like any other day. I would be awake by 6:00 AM, shave my face, and then while in the hot steamy shower I would shave my entire pubic area as well as that little bit that grew above the crack of my ass. I wasn’t an overly hairy guy, “But silky things needed to be against silky smooth skin.” I loved being smooth under my panties and each day was a new adventure in my favorite secret activity, wearing panties bahis siteleri to work.I tried not being predictable with my panty selection for each particular day. Often I would lie in bed as I cleared my head of sleep and run the choices through my head. Would I choose something frilly and super sexy or would I go with a simple brief style in a safe color? Safe colors were dark bold colors, nude, and of course white. I battled with myself every morning and I often thought about wearing 4 or 5 panties at a time just to enjoy knowing all the pretty colors that held my little package in place.“More coffee?” the waitress asked flashing a toothy smile and shifting her hips which drew her shorts up between her legs forming a perfect and prominent camel toe image. My eyes were drawn to that image, which I am sure she knew would happen, and instead of lusting after that mound of sexuality I wondered, “what sort of panty allows such perfect detail?”“No, I’m fine, but can you answer a question for me?” I asked as I placed a $20.00 bill on the table, holding it down with my middle finger, to pay for a $3.00 coffee. I slowly slid it across the smooth glass table where her middle finger again was touching the glass. I know she saw the other $20.00 bill held between my palm and thumb.“Sure, you can ask me anything,” she said with a syrupy smile and a look of satisfaction that she had accomplished her goal of a big fat tip.I leaned across the table as she lowered her head and gave me that money shot down her top again. “What brand of panty are you wearing, I love the way they fit you so well,” I asked knowing I was over the line in this politically correct world.I looked up from her magnificent breasts to her deep green eyes and waited for a change in her expression or perhaps a full hand slap across the face. Instead her fake toothy smile changed to a sweet smile and a softening look in her eyes. “Who said I was wearing panties?” she asked with a teasing smile.“I did,” I said and leaning closer whispered, “I know it is not a thong, I can see a faint line of the vertical center seam and when you walked away I know I saw the faintest hint of lace through your shorts on the backside.”“Hmm,” she said as she pushed her arms together pushing her beautiful breast up a bit, “since you are such a perceptive observer, what color?” She asked.“Pink would be the obvious guess, but no, I know that they must be a dark rose color even though you are wearing a white bra. Your rose color lipstick and nail polish tell me that is your favorite color.”She blushed and whispered, “They are called Flirty Fit, a lacey cheeky panty, and yes, a lovely dark rose color, it has been a pleasure to serve you,” she said as the first $20.00 bill vanished into the waistband of her shorts that enabled me to see the pretty satin bow on the waistband of the lacey panty. She let the spandex snap back and placed her middle finger on the table and slid the next bill her way and asked, “where did you buy them and I am guessing a size small?” and held the bill down with my middle finger as I looked down her top again.“On-line, I got the last 6 of these, they are now discontinued but I am sure if you searched for them you’d find something that suits your taste. Oh and I do I wish I could wear small, they are medium.” And as she finished speaking the second bill vanished with her.“It is remarkable,” I thought as I sipped the coffee that was now cooling off, “I can be so openly sexual about panties with a stranger like this cute little waitress, yet at work this morning I wanted to crawl under my desk.” I had thought of this before, my obsession with panties was just part of me and I did rationalize that this waitress had made an overtly sexual approach to me in an attempt to garner a big tip so I felt some justification to get personal with her.I noticed a young woman seat herself at the table next to me. She was very smartly dressed with a white blouse that had to be silk. It d****d across her perfectly proportioned torso only as silk does. The sun shone through it and although it was not a particularly sheer fabric the strong sunlight let the underside of her breasts show in what was a white lace bra. Just like panties, I loved the details that so many others missed.I thought of my morning dressing ritual. Follow my shower and shave I would lotion my shaved pubic area and then apply talcum powder, you know the sweet scented one intended for diapers. Then after selecting the panty I would stand in front of the mirror and let the morning sunlight shine through my panties as I pulled them on. I never rushed, I loved the feeling of the elastic tugging on my legs and the view of my cute little cock and balls as they vanished behind the somewhat sheer panties.Did I mention I never wear cotton and I avoid lace unless it is a side panel? I want only the finest silky fabric on the front and back, “why would you wear anything else?” I often asked myself. I watch my share or porn and see so much satin but for me that is all about play time. It feels wonderful to the hand and fingers but all too often the inside of the satin does nothing to caress those parts of my body that produce such pleasure.I caught myself staring at the canlı bahis siteleri woman’s breasts through the silk blouse as she selected from the menu. Her blouse was neatly tucked into her skirt but one corner was out just enough to see a hint of red that screamed at me to know more. Then the cute waitress approached her and looked over at me with that knowing grin. She knew exactly what I was thinking about.The waitress took the order and before heading back indoors she stepped to my table, leaned over showing me her breasts again, “Donna Karen silk and Soma sensuous lace, light nude, oh and 34C.” she said as she rubbed her fingers together indicating she expected to be paid.I pulled out two $20.00 bills, “and the panties?” I said as I held both bills at the ready.“I thought so,” she said with a smile, “not matching but Soma sensuous chantilly rio in cherry red, I didn’t ask the size if that matters,” she whispered with a wide smile.“You are the best,” I said as she pulled the bills from my hand.I had just given up $80.00 for the thrill of knowing what the two of them were wearing under their cloths which did nothing for adding to my collection of pretty panties for myself. But my job paid well and life is all about the finer things. That brought my mind back to work and how to handle what Ann started this morning.Out in a public place like this where I rarely ever saw the same person twice it was easy to be brave. But setting next to a woman that happened to be my coworker was another matter. I decided that if I just kept quiet and busy it would all go away by the end of the day.Our call center was always busier after lunch and the fact that Ann had the later lunch would make it possible to keep a low profile. I liked her, she was attractive without being some knock-out sort of woman and she was always smartly dressed. We had exchanged pleasantries when she took over the empty unit in my cubical a few days ago. I rarely tried to get involved with my coworkers because my fetish pretty much defined me privately and when women find out about it things always ended badly.I was not gay nor did I consider myself bisexual. And I had no desire to be a woman, I just love panties and had made a lifelong study of women’s undergarments. I prided myself in know more about them than most women did. Ann left for lunch when I logged back on to the network. She placed a hand on my shoulder as I plugged in my headset and I nearly jumped out of my panties with the surprise. “See you later Larry,” she said and was gone.The afternoon was busy almost to the point of being hectic and then it was 5:00 PM and time to log off for the day. As I put my headset down I heard Ann’s chair squeak again and she rolled up beside me. “I know I made you uncomfortable this morning,” she began, “let me make up for it, let’s go have a beer, I know this cute little spot where my girlfriend works and I am sure you will like it.I agreed only because I wanted the whole thing to go away quietly. We rode the elevator down to the ground floor and before I knew it we were right back to my lunch spot and the very first waitress that walked to the table was the cute one I had paid so generously. I smiled as if to say, “not a word.”But that was not to be. “Well hello again, twice in one day.” And then she turned to Ann, “hey babe, hard day? How about a beer for both of you? Your regular Ann?”“Sure, are you off in a minute?“ she asked as she reached out and held her hand.“Yes about 5 minutes.” She said. Ann didn’t let go of her hand, “grab a beer for yourself and I will pay for them before your shift ends.”The waitress left with a smile that told me these two were more than casual acquaintances. “That is my girlfriend Cara, she is so much fun. How did you meet her?” Ann asked.“I didn’t really meet her I guess,” I said trying to make it sound right, “she waited on me for lunch.”“I knew it,” Ann said, “I met Cara here for lunch and she said she had met the sweetest guy who was a good tipper and so polite. “I was relieved that she didn’t consider me a creep but was still a bit uncomfortable with the situation. Cara returned with three beers and accepted Ann’s credit card, “be right back she said and walked away moving her sexy little hips so seductively. I wondered if Ann caught it and looked over at her, she did and she was smiling.“That girl has the sweetest ass, wouldn’t you agree?” Ann said taking a sip of beer from the frosted mug. It left a little white foam on her upper lip that she gave a quick little lick with the tip of her tongue in the most arousing manner.I didn’t answer but smiled as Cara returned to set with us. “Whew! It was busy today,” she said taking a drink of the beer. “You know Ann there are so many creeps that come here, I love it when someone like your friend shows up and is a gentleman.”“Well we need some introductions, Larry this is Cara my girlfriend, Cara this is Larry that works in my cubicle.” She said as I extended my hand. Cara took it and the soft skin of her hands made me want to never let go.“It is nice to meet you Larry, so there is this question that begs an answer,” she said taking another sip of beer. “I know, let’s make this a truth or dare sort of thing. I dare you to canlı bahis answer my question without hesitation or you will have to accept my dare. Deal?” She didn’t wait for an answer as she continued, “You tell me what color and style panties Ann is wearing and if you don’t answer you need to tell us every detail about the panties you are wearing.”I was shocked at her boldness and glanced around hoping others didn’t hear. But it was the after work crowd and their conversations kept them busy enough to ours wasn’t part of theirs. I looked at Ann, who had obviously told Cara about the incident in the office. Ann smiled, “come on Larry, this is so easy, you know what color what else did you know from that little glimpse? Cara told me how good you were at knowing more than most people would observe.”I sat in silence, my face was red, and although I had been more than bold with Cara I suddenly felt like getting out of the place. Yet there was something about the challenge that was just presented to me and the boldness of the conversation. I had never met a woman that had engaged me in this way and that was gratifying in itself, and now there were two that seemed like minded in this respect.Cara, aware of my hesitation, looked at me with those beautiful eyes and seductive cleavage and said, “I know you seem to be a bit of an expert on the subject and figured you’d enjoy the little game. We don’t want to make you uncomfortable.”I cleared my throat, took a drink of my beer, and looked at Ann saying, “well I don’t know if this is fair, after all you did flash me in the office.”“You didn’t!” Cara said playfully slapping the back of Ann’s hand, “You are so bad girl.”“Well yes, see I noticed Larry’s silky blue panties and I just wanted to make him feel a little less awkward.” Ann said as she giggled nervously.“So game on?” Cara asked leaning on her elbows showing me her deep cleavage and this time I was sure I saw her areola peeking out the top of her bra.“Okay, I will state the obvious,” I said. “Ann said they were minty green but in actuality more of a moss green. They were worn under a very high end pantyhose, I would guess they were by Flake because of the quality, the matt finish, and the lace elastic that obscured some of the details of the panties. How am I doing?” I asked starting to feel like I could meet this challenge.Ann was blushing as I looked at her, “You saw all of that in the 2 seconds? I am now worried that you are aware of my other flaws that barely show such as this tiny scar here,” she said as she pulled her blouse open a bit and I saw the tiny white mark.“Nope, didn’t see that, but if you open the top two buttons I would certainly enjoy seeing more of that camisole you are wearing to hide your bra straps.” I said with a self-confident smile. “Now back to the challenge. I am sure that your panties are a flapper style because of the folds in the panty fabric under your pantyhose. The matt finish pantyhose hid the fact that they are more than likely satin finish and I loved the black trim and the little black bow in the center.”“Ann, you are wearing my panties,” Cara said and slapped Ann’s hand again, “you are so naughty, you wait until we get home babe!”“Well that makes the size easy since I already know Cara wears a medium panty. But the most difficult part is the maker. My first thought is something vintage, you know something from the 1930’s or 1940’s. Which back at that time Van Raalte But the color just doesn’t fit that era. This is tough.” I said.I looked at Ann and Cara looking for a hint in their expressions but found nothing that would help. “Give up?” Cara asked.“Well sort of but as much as this sounds like a wild assed guess I would say they are handmade and you more than likely purchased them to be a bit flirty during some big band dance class you were taking. Mind you, just guessing.” I said and took a swallow of beer as the two girls exchanged looks.Cara turned back to me, “Are you sure Ann didn’t tell you all of this just to prank me?” She asked.“Are you saying I am correct?” I asked looking between the two of them.“Yes,” Ann said, but not for a big band dance class. Cara took some pole dancing classes and loved showing off her panties to the other girls in the class.” And she slapped Cara’s hand, “You were pretty naughty in that class you know?”“Well I met you didn’t I?” she asked and leaned over and kissed Ann on the lips. And it was more than a friendly girlfriend peck, it was a full lipped lots of tongue kiss.“Looks like you two need some privacy,” I said finishing my beer and pushed my chair back.They broke their kiss and smiled in a way that told me the evening was over. “See you tomorrow at work?” Ann asked.“Maybe lunch again, I get lots of interesting customers and your next few guess are on me,” Cara said giving me the little bent finger wave meaning good bye.I stood, took two steps away, and then stopped and faced them. “Early 1980’s Shadow Line in Baby Blue,” I said with a wink and left them to enjoy their evening. I had no idea if Ann would be a problem at work but I didn’t care. For the first time in my life I met women that didn’t judge me for what is part of who I am.NOTE: This is a single chapter story that stated with a phrase that floated through my mind. And that is “It isn’t easy being a panty boy.” I wrote two versions of this because the first one just seemed lame as I neared the finish. So hope all the panty boys out there enjoy this little flight of fancy.

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