She looked back at the painting and I pulled my pants and panties down in a single motion. Then I kicked the bottoms underneath her bed, so that there would be no chance of her catching a glimpse of the red lace that had been on my body for the better half of the day. She looked back at me and said, “It’s cute, isn’t it? I got it at the flea market.”
I crawled on top of her before she could notice the reddish indent where the panties had been on my body. I was no longer wearing the feminine undergarment, but the imprint was just as obvious. She looked down my chest at my cock. “You’re hard,” she said with glittering eyes.
“Of course I am,” I said. And then I wondered if her boyfriend could get hard as easily as me. Maybe he was on a drug trial of his own.
Cassidy reached down slowly and then she wrapped her fingers around my cock. She gasped, as if shocked to feel that it was real. “It really is hard,” she said, still sounding very surprised. She began to stroke it and massage it in her clenched fist. “And it’s warm.” She looked into my eyes. “Can I suck it? My ex never let me suck him. He thought it was gross.”
This ex-boyfriend sounded like a complete weirdo. I wasn’t going to say no to a blowjob. So I crawled up her body and then I planted my ass down on her chest. “Go ahead,” I said. She marvelled at the sight of my erection for a moment before pointing it down and letting it into her mouth. She sucked it with an elated moan, as if she was drinking water for the first time in two long days. She sucked hard and slurped harder. It was only a minute before she started bobbing her head quickly, pressing her lips down hard to arouse my tip, which was already throbbing. It felt good—too good. “If you aren’t careful, I’m going to come in your mouth,” I said.
She let a little giggle slip. “I kind of want to know what that’s like,” she said. “But I also want you to fuck my pussy.” So she spread her legs and let her head fall back onto her pillow. “I’m wet,” she said. And she wasn’t lying. I got back down between her legs, and saw that there was a wet spot on her pink bed sheets, and some warm, clear fluid dribbling down her soft bum cheeks, emanating from her pussy. I rubbed my cock in her rogue fluid before pressing it against her lips. She let out a moan, as if the touch alone was enough to bring her to the edge of an orgasm. I slid my cock up and down and then I got my tip lined up with her hole. I pressed in.
She was tight, but not tight enough to stop me from sliding in deep. She was warm—beautifully warm, and wet. Fluid squished out as I squished in, and then she moaned again. She reached down and began to rub her clit with two fingers. I watched those fingers move in tiny circles for a moment before starting to thrust in and out of her tight snatch. And then I felt a strange sensation buzzing inside of me: jealousy.
Fucking Cassidy felt good, but it looked like being fucked felt better. She looked so happy, and she was so sexy. I wanted to feel sexy like that. I wanted to lie on my back in lingerie while a throbbing erection slid in and out of me.
I took a sharp breath in, realizing what I had just fantasized about. No—I didn’t want an erection inside of me. I didn’t want an erection anywhere near me. Though it was fun to think about being sexy enough to give a man an erection. Surely that must be a nice feeling. I understood why her eyes were suddenly glistening when she saw my cock throbbing and standing tall.
I ran my hands up and down her smooth legs. And then I remembered that my legs were smooth too. My heart stuttered. How had she not noticed? Or did she notice, and she just didn’t say anything? My legs were now rubbing up against hers—surely she could feel that they were bare, like the legs of a woman. Or was she subconsciously having some sort of lesbian fantasy in her mind? Her eyes were closed, after all…
I closed my own eyes and found myself imagining a strange visual: myself as a woman, fucking Cassidy with a big strap-on. And as I had this strange visual pleasing my mind, I swear I could feel a tingling, as if the back of the strap-on was rubbing against my pussy. My legs began to tremble and I let out a long, intense moan. I imagined myself squirting: gushing warm fluid out from my pussy and down my legs. “Fuck!” I groaned, digging my nails into Cassidy’s sides. She gasped and then she suddenly pushed me back. I opened my eyes and looked down. I watched as cum spewed out from the tip of my cock, onto her pelvis—and then I watched as cum dribbled out from her pussy in a big glob.
“You were supposed to pull out!” she said. “I’m not on birth control.” She reached a finger into her pussy to pull out the rest of my cum. But my cock was still discharging. One blast even landed on the back of her hand that was pulling out my creampie. It took a moment for me to snap out from my daze.
“Sorry,” I said. I got off of her bed.
“You were supposed to come in my mouth—remember? It’s fine. We can do that another time, if you want. No pressure or anything.” She stood up and looked down at herself. She was covered in my white load. I couldn’t believe how much was on her. “I need to clean myself up. I’m just going to take a shower. Help yourself to another beer or even some more cookies.”
She walked carefully over to the bathroom, stepping slowly so that the cum wouldn’t drip onto her clean floors. And then I was left alone in her bedroom, with complete access to all of her cute little outfits. I opened the closet and saw that she had lots of lingerie—most of items even still had tags on them. I wondered if she would notice them missing. Surely she wouldn’t notice a single item missing. So I grabbed one of her many pink little outfits.
But that wasn’t enough. I also grabbed a pair of pink panties, a pair of white stockings, and then I found an old pair of black heels in the back of her closet. I snatched those too, along with a handful of tops that I didn’t even bother to inspect. I crept towards the front door and then I slipped on my shoes. “I’m heading back to my place. I’ll see you later!” I called out.
“Oh. Okay,” she said back from within the bathroom. “See you.”
I got out quickly, running across the hall and into my apartment. I brought the haul to my bedroom and hid it all deep in my closet. I was excited to try it all on, but I was also deeply confused as to why I grabbed it in the first place.
CHAPTER IV
I managed to resist the urge to try the stolen lingerie on—until the next morning. I had no plans and it was an unseasonably cold day, complete with snow—a perfect day to stay inside and do nothing, which was exactly what I didn’t want.
But I could think of nothing to do. My crappy car didn’t have snow tires and I had no chores that needed doing, so I ended up in my bedroom, standing in front of my mirror while trying on lingerie. I looked pretty good in pink. I was surprised at how well the little outfit fit me. Even the stolen heels fit me with a bit of squeezing. They were only a single size too small for my feet (which were admittedly small for a man).
But even all dolled up, I didn’t feel satisfied. I knew that my body was shockingly feminine, but I wanted to see just how far I could push the look. There was a drug store attached to my apartment building. I put on some clothes over my lingerie and I went down. It was empty, save for the woman working at the counter and another woman working in the makeup department, which was where I needed to be. I casually walked up and down the isles, grabbing the odd random item. In my mind, I was concocting a lie to tell the employees, so they didn’t think I was buying myself some makeup.
Once I entered that makeup department, my heart started to pound. I held it together, casually looking down the isles. I took out my phone and pretended to be looking at a list from my made up wife. It was only a minute before the employee was at my side. “Can I help you find something?” she asked.
I turned and smiled. “Just picking up a few things for my wife. She’s out with our daughter,” I said before turning back to the shelves.
“Well what’s on that list? Maybe I can help you find what you’re looking for,” she said. My stomach turned. I didn’t actually have a list. My plan was just to grab a few things that sounded like necessities.
; “Oh, that’s okay. I think I can find what I need.”
She stared at me for a moment, cracking a slight grin. My heart skipped a beat. Could she tell that I was lying? Did she know that I was buying makeup for myself?
“Well, I think your wife would really like this foundation. Every girl should have a good foundation. And then this eye-shadow is a must as well—it’s the one I’m using right now.” Her eye shadow did indeed look quite nice.
I cleared my throat. “I think those are on her list, actually,” I said, forcing a smile, trying to act as cool as possible. She couldn’t possibly know that I was shopping for myself. Surely husbands buy makeup for their wives all the time, right?
“And this liquid eyeliner is perfect. It’s brand new—I haven’t heard of one person not liking it yet. And then, if your wife needs lipstick, there’s this great package with five different shades. It’s a killer deal. Individually, these sell for thirty bucks each, but the whole package is only forty-five bucks. Oh, and then she’ll need some blush.” She kept handing me items faster than I could reply. But I didn’t mind. I wanted all of it. I could wait to get it up to my apartment to try it out.
She brought me over to the counter and then she charged almost three hundred dollars to my credit card. Then, I found myself locked in my apartment, in my bathroom, dolling up my face so that I would look as pretty as possible in my skimpy pink lingerie. It was actually kind of fun, seeing how tiny little details could make such a big difference. And it was fun seeing how a little bit of makeup could change me from a man into a woman.
I looked cute, but I still wasn’t satisfied, even after walking up and down my hallway in those tiny heels. I felt like I needed more, but I wasn’t sure how to get it. I wanted some sort of validation, but I wasn’t stupid enough to leave my apartment or start posting pictures on the Internet. I ended up sitting on my living room couch, staring at my own reflection in the window. I saw that I had a big smirk on my face. And how could I not? I really looked like a chick. What was stopping me from going out onto the streets? Maybe it would be interesting to see if I could turn a few heads and trick a few guys into thinking that I was the real deal.
That smile grew bigger, and then it went away suddenly as reality slapped me in the face. I wasn’t actually considering going out, was I? And I hadn’t really just spent nearly three hundred bucks on makeup, had I? Maybe I was losing my mind. Maybe that drug was eating away at my brain. At least my ears weren’t ringing… Was it worth it?
But the boredom of the snowy day caught back up with me, not even an hour later. I ended up on an online wig store. I ordered myself an adorable black wig: long and straight with cute bangs. It was made with real human hair, and it cost me another three hundred bucks. I knew I didn’t have the money to spare, but I still clicked that ‘checkout’ button anyway. I really was losing my mind, and I was apparently losing control of my body as well. It wasn’t even until I got the e-mail confirmation that I realized I’d ordered the wig express, to be delivered next day. And apparently I paid fifty bucks extra for that option.
I felt like an idiot, but a part of me was excited that I would soon have my wig. I spent the next three hours lounging around my apartment, watching television. I was in my lingerie and makeup, and I felt so peaceful. I got excited every time my screen went dark and I saw my reflection. And then I saw an ad on TV for a reality show about cross-dressers. The ad made my heart swirl down into my stomach.
All of the guys in the ad looked so pathetic. None of them really looked like chicks, but they were all convinced that they were hot. Was that me? Was I convinced that I looked hot, but in reality I was just a pathetic-looking loser?
I went to the mirror and stared at myself. I thought I looked good, but maybe that was just the drug. If the drug could make me want to put on women’s clothing, then it could make me think that I looked good. I probably looked ridiculous. If anyone saw me in public, they would probably laugh behind my back. If my parents saw me, they would probably disown me. If my friends saw me, they would probably stop being my friends. I needed to get out of that outfit and I needed to get myself cleaned up. So I took a shower and stuffed all of the girly clothes and makeup into the back of my closet. I threw an old jacket over all of it, so I wouldn’t see it and be tempted to put it on. I needed to get a hold of myself. I needed to realize that this feminization was just a side effect of the drug. And most side effects are temporary. Once I was used the drug, the sissy side effect would surely subside. And if it didn’t, maybe I was better off with the tinnitus. At least I wasn’t humiliating myself on a daily basis when my ears were ringing.
I put an action movie on my TV and then I glued myself to the couch, with a cold beer in my hand. I was a man and I needed to remember that. I couldn’t let myself forget it, no matter how hard the drug tried to push me towards that lingerie and makeup. I had to keep my sanity, no matter what.
CHAPTER V
The deliveryman came right to my door before I left for work the next morning. Someone must have let him out while heading out the front door. “I’ve got a package for a Seth. Is that you?” he asked, holding out the box that contained my very expensive wig, which I told myself I would return and keep off of my head.
“That’s me,” I said, taking the package and putting it down on my kitchen counter before taking off for work. Work was a welcomed distraction from the feminine urges pulsing through my brain—but it wasn’t a cure. I once again found myself staring over at Martha when she came into the office. I looked at her little pencil skirt and thought about how comfortable it must be. That morning, HR announced that they would no longer enforce the female dress code for the office. Martha didn’t seem phased by the announcement. I could tell that she liked wearing little skirts and tall heels. If I was a woman, I would have liked it too.
Men were always staring at her. Our bosses all adored her and obviously wanted to fuck her. I would have liked a bit of attention like that. I could only imagine that it was fun, getting up to get a coffee, just to have five faces following you, wishing they could be with you. It was sad to think that I would never know that simple sort of pleasure… Unless I came to work in my girly guise, and I really was convincing like I was fairly certain I was.
I would probably get a few weird looks at first. Maybe I would lose a few office friends—guys who didn’t want to associate with the weird office cross-dresser. But then, once they got over the weirdness of it all, maybe they would occasionally steal a glance. My ass was just as good as Martha’s after all—maybe it was even better. My legs were surely just as fine, if not better. I knew that my face was cute. At some point, the men would cave and admire me, even if just from behind. Maybe it would be fun…
Or maybe I was letting my head get filled with stupid, humiliating ideas. I knew I had to be careful. I knew that if I let that drug take over my mind completely, I would end up friendless, humiliated, and maybe even jobless. Or maybe it would save my ass. Maybe they wouldn’t be able to fire me if I suddenly identified as a woman. They were only firing men after all, right? Maybe I could tell my friends that I was just doing it to save my career—maybe they would even try to do the same thing.
My heart fluttered. Then I slapped myself on the cheek. I couldn’t allow myself to have these ideas! I was really considering it—and the consideration alone was humiliating enough.
Martha looked over at me. She smiled and I looked away quickly. I wondered how long I’d been staring: too long for sure. It was starting to become a problem. I knew that if I wasn’t careful, I would end up down in HR.
Before going out to lunch, I made a trip to the bathroom so that I could splash some cool water on my face. But I didn’t go to the nearby bathroom; I went to the one far down the hall, near the end of the floor that was being renovated. I needed to be alone. I needed to spend a good minute staring myself in the mirror, trying to pull the pieces of myself together. As I emerged from the bathroom, Martha was standing there, in her little penc
il skirt and white blouse. I tried not to look down at her legs, which looked so cute in her tall heels.
“Hey Seth,” she said.
“Hi Martha,” I said.
“I can’t help but notice that you’ve been staring at me a lot lately,” she said. My stomach turned. Was she about to warn me not to look again? Was she going to give me one last chance before she ratted me out to HR, or to her husband? I couldn’t decide which was worse.
“I’m sorry. I—I’ve been tired. I haven’t been… in the best state of mind.”
“I’m assuming you heard that me and my husband are getting a divorce. I was hoping the news wouldn’t get around the office, but I guess it was inevitable.”
I bit down on my tongue and forced a smile. I shrugged my shoulders. “That’s too bad, Martha. I’m sorry to hear that.”
“It’s for the best. We weren’t getting along. We’ve been sleeping in separate rooms for the past four months. It’s been hell, really. You won’t tell anyone, will you? Do you mind if I ask who told you? I’m not going to go and chew them out or anything—I’m just curious to know how you found out.”
“I, uh, can’t remember,” I said. It was better that I played along, rather than make her think that I was looking at her for another reason. I didn’t mind her thinking that I was attracted to her—at least that made me feel like I was still a man. The last thing I wanted was for her to know that I was actually admiring her shoe choice. “But again, I’m sorry to hear about the split.”
“And you promise you won’t tell anyone?” she said.
“Of course, Martha. It’s none of my business.”
She smiled and bit her lip. She looked back over her shoulder and then back at me. “I’ve been married for nine years. This is so embarrassing, but I’m actually kind of excited to be flirty again. I’m not even sure I remember how to do it.”
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