Thinking With My Dick - Ch4 - A New Routine free porn video

Author's note: This chapter took a little longer, as I keep getting distracted by wanting to jump ahead and write some of the fun smutty bits that happen later on in Jamie's misadventures. Hopefully that means those bits get finished faster when we get around to them, but knowing my luck, probably not. Thanks to everyone who's reading and enjoying this, hopefully this is up to the standards of the rest. ----------------------------------------------- I woke the next morning, showered, and went to work. My painted toes were obvious against the white of the shower floor, accusing, or inviting, I'm not sure which would be worse. I was constantly conscious of the heels in my closet as I got dressed, but did my best to ignore them. Work was perfectly normal, except I had nail polish on. That felt far more consequential than it sounded in my head. That even though they didn't know it, everyone I knew talked to me that day while I had painted toes. I had lunch with Nicole from admissions, and Meghan, another librarian, and was quietly amazed that neither seemed to think anything was different. Everything seemed different to me. The rest of the week proceeded much the same way. I didn't break into the girlie bags, or my hidden box of heels again, but I also didn't take off the nail polish, and I shaved again, the feel of being smooth was starting to grow on me. I tried to tell myself swimmers did that, and some runners did too, but I'm not sure I believed it, after all, that still wouldn't excuse my shaved ballsack. I relapsed on the weekend, and took the heels out of my closet. I wore them almost constantly while I was home and not out on a run or doing errands. It seemed I wore heels easily. Walking in them was never that hard, and by the end of the weekend I'd even started modifying my gait while I wore them as I got used to them. Shortening my strides, with my weight slightly forward and a bit of a sway in my ass as it pushed out behind me, I tried not to think about the fact that it could only really be described as a mincing gait, but it worked much better with the heels and I moved much more quickly around the house with fewer balance issues. They didn't even hurt much, but I wondered if that was because I didn't have a lot of cause to be standing around in my own apartment, and it was easier sitting on the couch with my weight off my feet. That said, by the end of the weekend, I thought I might be starting to develop a small blister on my pinky toes where they rubbed against the toe-strap. For the most part, I just bummed around the apartment, watched TV, played some video games, and browsed the web. I couldn't help browsing women's clothes again, still surprised at how cheap the cheap end of women's clothes are. This must be how girls who like lots of different looks afford it, they mix in cheap clothes that they know won't last long because they'll be on to the new fashion by the time they wear out. Idly I also looked at some size charts, surprisingly if I converted my sizes to women's I wasn't as enormous a size as I expected. Oh, my waist wasn't small for a girl, but short height, a slim runners build, and narrower boy's hips meant I was solidly in the middle of the girl's sizes. Not exactly petite, but I wasn't a plus size either. I discovered that somewhere in the last day or two I'd chipped the polish on some of my nails. I'd always thought chipped nail polish looked really tacky on girls (either wear nail polish and maintain it, or don't wear it at all), and I found I couldn't bear committing the same sin myself. I ended up removing, and redoing the polish on all my nails, and then, for good measure, did my fingers as well. I masterbated constantly. Each time I came a massive wave of guilt rolled over me. I'd clean myself up, and try to go get back into 'dude' mode as best I could, but I started to be lax on some things, a small contrary part of my brain wanting to keep some things ready for the next jerk session. So I even as I got back into jeans and boxers, I would leave my nail polish on, justifying it that I'd waste so much time taking it off and reapplying it later, and I'd strap on my sandals, telling myself that I just wanted to see if they really did start hurting after long wear. By Sunday, I was even wearing Annie's leftover panties most of the time as well, even though I still felt bad wearing 'her' clothes. Sunday evening, dejected after my last jerk off session that I still couldn't keep my deviant kinks under control, I got to work taking off my nail polish for the week ahead, and realized I was running low on nail polish remover. All the soaking that had been required last weekend to get off the glue on nails had used up a lot of the bottle. If I was going to keep doing this, I'd need to get more. Emboldened by my success at buying shoes, I figured it wasn't worth driving all the way out to some remote supermarket like I had last time. Instead, I got in the car and drove to the nearby Target, figuring they'd have remover, and I could get some other sundries for the week while I was at it. I should have known this would be a mistake. Problems started as found the beauty section to grab the nail polish remover before moving on to the other stuff on my list. Turning into the aisle, right beside the nail polish remover, I was confronted with a wall of nail polish. My gaze kept drifting over to it as I picked up a large bottle of remover (I wasn't fooling myself, I knew I'd be using all of it eventually), spotting all kinds of interesting colors: golds, glittery silvers, cherry reds, hot pinks, bold blues. I tried to pretend to be interested in something else on the shelf, but the entire aisle was full of things I shouldn't need to buy. Glancing nervously around the aisle, I saw I was alone, and quickly went to work. A hot fuschia, metallic gold, a classic 50s style cherry red, and a deep brownish maroon color all went quickly into the basket. I hustled out of the aisle, hoping no one saw me. The next aisle was haircare, and I grabbed a bottle of shampoo to try to help camouflage my purchases, it didn't feel nearly enough to outweigh the mass of femininity in the basket. Then I hit on an idea. The washing machine had eaten a hole in a pair of boxers recently, and I was always wearing out socks while running. I'd hit the men's department and grab a few things, nothing would say "Dude" like novelty boxers and athletic socks. That part of the plan went swimmingly. Things started falling apart as I walked out of the men's underwear section and directly into the women's underwear section right next door. Glancing around, I was still shocked at how cheap some of the items were, even compared to the men's boxers I'd just picked up, there were five and ten dollar items hanging every so often on the racks. Then the thought of Annie's leftovers hit me. I did keep feeling bad about wearing her clothes, I could easily get some of my own here. I picked out four pairs of panties, a g-string and three thongs, all with a sheer or lace component, and none with a backside wider than half an each. By then I was getting carried away. Two pairs of cheap sheer thigh high stockings (I'd always been fascinated by them, but none of my girlfriends ever owned any), a pair of tight black leggings, and even a pair of what looked like jeans with some strategic distressed rips but were made of something much more stretchy and were called jeggings on the tag. I guessed at all the sizes, I wasn't mad enough to try them on, going off of what I remembered seeing in size charts during my web browsing earlier in the day. Then I turned the corner and spotted the section of bras. I wasn't that crazy was I, wasn't the basket of girlie clothes and nail polish enough? I answered my own question as I walked towards the bras, pulled along by my perverse desires. I had no idea what my bra size would be, obviously the smallest cup possible, but I guessed from my suit jacket chest size as a starting spot and then went a little smaller. I found a fairly plain white bra, a push-up A cup with slightly padded cups, and a deep plunging front with a tiny bow on the strap connecting the two cups. It was something for a teen just growing into her boobs. It went into the cart too. I pulled myself from the women's section after that. Doing the rest of my shopping, a couple of light groceries, toothpaste, etc. I kept hoping that it would start to look like a man shopping for a household, but it never did. Not that I put any of it back. I brought my basket up to the checkout, sure that the salesclerk could see the embarrassment written on my face, but thankfully she was just as uninterested in my life as the women at the shoe store had been. Thank god for bored retail employees. I could probably have bought a horse without getting a reaction. I got home with my hoard of feminine goodies and unpacked it all, putting away my normal purchases, and lining my girl purchases up on the kitchen table. What had I done? I'd gone out and bought myself women's underwear. What kind of a perv was I turning into. What was I going to do? Apparently the answer to that was, have myself a private little fashion show. I repainted my toes, gold this time, to try out one of my new colors, got out my heels, and started trying stuff on. Everything fit far better than I anticipated, my slim physique coming in handy, or problematic depending on my point of view at the time. If I'd looked more like a big hairy dude, this might not have been so titillating. Instead the girl clothes made me look androgynous at best, feminine at worst. I loved all the panties as they fit snugly up my ass crack, displaying my ass and legs to good effect, with my flaccid tucked penis barely showing a bulge (though as my show went on, this started becoming more of a problem). I settled on one pair for the moment, a pastel pink number in almost all lace, with a wide four inch waistband that rode up my hips towards my waist, a tiny swatch of lace to cover my crotch, and a thin strip that ran up the back, to start trying the other items. The leggings looked good, again benefitting from my toned runner's legs, and were ultra feminine leading down into my heel shod feet. Looking in the mirror, my legs looked just like a style I'd seen girls wear. I hadn't thought it looked all that good for them, but it was definitively feminine, and the thought that it was me in this slightly unfashionable women's wardrobe was making my tuck difficult. Then I tried on the jeggings. For all they had faux buttons and pockets, it was all decorative, they pulled straight up just like the leggings. Getting my heels on, I couldn't believe how the clothes changed the look of my legs. I couldn't help it, I had to see it with the bra. It took a few trial and error cycles to get some of the straps properly adjusted, but then it was on. I was wearing a bra, and what little pectoral muscle I had was getting pushed up in simulation of cleavage, and assisted by the padded cups. That was it, I needed to see if I was even vaguely passable. I'm not sure if that was the feminine part of me hoping that I was, or the male side hoping that I'd see a failure and give this up. I rummaged in my drawer for a shirt, pulling out a band t-shirt for Stolen Pony, and pulled it on. The shirt would give me a better impression of how big, or small, I was with the bra on. Turning back to my mirror I angled it so I could only see myself from the waist down, and it shocked me. I *was* almost passable. My face and hair would never been mistaken for a guy's, but my body just might. Tall heels, skin tight pants, and a casual band t-shirt whose center sported two protrusions as my push up bra did it's work, and pushed me over the edge. I shucked off the clothes, and then lay back on my bed to jerk off over the knowledge that I owned and wore girl's clothes. Coming to my senses again after masturbation and subsequent cleanup, I moved everything back to the kitchen, where I could put it out of sight and out of mind. Work began in the morning, and I didn't need this fiasco with the girls clothing hanging over me. But as much as I wish I was free of it all, I still went to bed with gold toenails, and wearing a pair of pink thong panties. ----------------------------------------- My week started to fall into a routine. I'd spend the workday as a guy, hoping that my activities at home weren't somehow visible to my co workers. In the evenings I'd come home and change into my female clothes, panties, the leggings or jeggings, t-shirt over the bra, and my sandals. I shaved regularly and repainted any nails that got chipped. I masturbated. A lot. During the week I realized that if this was going to keep up, I'd run out of clean girl clothes halfway through the week and was down to just wearing heels in the evening, I'd need a wider selection of clothes, and so I started shopping online. The clothes I'd bought gave me a rough idea of what my size are. I started with the basics, some more panties (all thongs), some stockings and panyhose, additional pants, and some women's tops (though those felt less exciting without a chest to fill them up. I splurged on a second pair of heels, pumps this time, in crimson red. My first order was small, but I was so impatient for it to arrive, I'd made several more before the first was even delivered. The weekend came and went, and as seemed to be becoming my habit, it was spent largely at home, with full nail polish and heels, except now my women's clothes were starting to play a role. Part of me couldn't wait for the week ahead when the first of my packages started to arrive, part of me dreaded it, wondering how I could possible stop myself doing this once the house was full of girl clothes. Throughout the next week, packages arrived, and I played with my new selection of clothes. I with three sets of packages arriving that week, I had more than enough clothes to make it from one laundry day to the next. At that point, my online shopping branched out, first a couple of skirts and a body hugging little black dress (if I to see how girl's clothes felt, I couldn't ignore that), then tentatively a selection of makeup. I got a little of everything, foundation, lipstick, eyeliner, eyeshadow, mascara, concealer, etc. I'd always been fascinated by girls that did themselves up with a full face of makeup. My girlfriends had worn eyeliner or lipstick occasionally, but had almost always avoided things like foundation. But I had always thought it a dramatic change of look, the smooth skin tone look of a girl who'd done her makeup from the ground up to hide any and all imperfections, and I wanted to see what it was like. I also tried to balance things out by trying to maintain my normal routine at least a little bit. Mostly that meant my running, which was becoming my last 'male' activity that I did outside of work. I'd realized I'd worn out the soles on my last pair of running shoes, and needed replacements. This is a pretty common occurrence, I managed to destroy a pair of shoes every three or four months, but given that's the only real equipment you need for running, you don't mind buying replacements regularly, especially with how painful wearing old or poorly fitting shoes ends up being. Once you find a model that fits, you stick with it for as long as you can. Unfortunately, that isn't always that long, as manufacturers stop making styles pretty frequently, and you have to go looking for a new shoe with the old fit, which is what seemed to have happened to mine. But, perhaps because of all my recent browser history, my internet searches turned up that only the men's version of the shoe had been done away with, the company was still making the women's version. Looking at them, I wrestled with the issue. These shoes had been a godsend, I'd had a clear stretch without injuries since I'd been wearing them, and I didn't want to give them up, but these would be for wearing out in public, not just at home. Did I really want to bring all this girl's dress up into my running, my one last sanctuary from the madness. Looking at the shoes online, they weren't that bad. Mostly powder blue with pink highlights. The fit would be the same, I'd just need to get the a higher women's size than my current men's. Plus, blue was a dude color, and lord knows most running shoes don't exactly have subtle men's color schemes (my current pair was a violent neon green). In the end, it's the exercise that mattered, right? Not what you looked like doing it. In the end, I'm not sure if I acted because I wanted the running shoes, or as another step in my apparently masochistic plan to delve deeper into femininity, but, tentatively, I bought the sneakers. ------------------------------------------------ These most recent purchases didn't arrive until almost the weekend, so Saturday morning I got up excited, and tried to apply my makeup. It looked awful, this was obviously not something you fell into doing easily. The foundation looked caked on, the eyeshadow was barely noticeable, and the lipstick looked crooked with uneven lines on my lips. It utterly took the wind out of my feminine sails. Until then, everything had looked pretty good on my slim body, but my face didn't want to cooperate. More than I ever had in one of my post-orgasm moments of clarity, I was disgusted and ashamed at what I'd done to myself. I got back into boys clothes for the first time at home in days, removed all my poorly applied make, and even removed the polish from my nails. I stayed a good hetero boy for all of 28 hours, before the perfectionist (or the girl) in me wanted to figure out how I'd gone so wrong, and I started looking at YouTube makeup tutorials. It didn't take long before I realized what I was doing wrong. Apparently, all of it. I had no makeup brushes, I was applying makeup in the wrong way, almost everything I could do incorrectly I had. Well, that settles it, now I know exactly why I can't make myself look like a girl with makeup. Sadly, knowing didn't settle the urge to get it right. I held out for another two hours before relenting. Going back to YouTube, I found a handful of looks I liked, and then, armed with a shopping list gleaned from videos, I went shopping again, picking up all the tools I needed, and any cosmetics I'd missed in my first shopping session. I tried to keep my streak of man-clothing alive, but I caved on Wednesday evening, repainted my toes (maroon), and got dressed. That day, I also threw in the towel on my running clothes. My old shoes were dead, so my new blue and pink shoes were pressed into service. It was also getting way too hot to keep wearing running tights to hide my shaved legs. I'd have to just risk it. I probably didn't have to pick some of my shorter running shorts to start with, but I did. Looking in the mirror, I didn't scream girl or anything, but I did seem to be falling into a somewhat androgynous range, not boobs or long hair, but showing a lot of smooth leg and slightly girlie shoes. In the end, I was blessed by the fact that most strangers on the street don't give a crap about your hangups, and ignored me while I ran, just like every day I'd gone running before all this started. Following this stunning display of indifference, my bare legs and pink highlighted running shoes became my norm. A few days later the rest of my makeup supplies arrived. Setting them up in my bathroom, now with a significant portion of counter space devoted to cosmetics, brought my laptop in, and started practicing. -------------------------------------------------- Pretty soon, makeup started becoming a staple of my weekends, and even some weeknights. I was still devoting my weekdays to my male persona, but the amount of time I spend dressed as a man outside work was shrinking rapidly now that at least some girl stuff had invaded my running as well. A couple weekends later, playing with girl stuff for so much of the seemed to have primed me to cross another dangerous bright red line. Showering and shaving in preparation for the day, my treacherous brain threw up a horrible, wonderful idea. I'd already tried seeing what my cum tasted like, even if only in the smallest of quantities, if I wanted to know what sex stuff was like for girls, I should try anal stimulation. The sober part of my mind rebelled, no way, that was a bridge too far, I wasn't going to put stuff up my ass. But my adventurous side needled me, gay men do it, and that's not girlie, and it's supposed to feel amazing, it's just another way of masterbating. I looked down at my hands, nails painted royal blue for the weekend. What would it feel like to finger myself? Before I knew it, I was moving. I grabbed my shower gel, as good a lube as I had available, and began to lubricate my butt with it. Then, tentatively, I poked at my asshole with a finger. I always imagined my sphincter as being tight, nothing in or out. But it was easier than I expected to poke my finger up my back passage. It felt odd and good. My cock immediately responded, probably not to any actual prostate stimulation but rather the transgressiveness of what I was doing. Though, whether I was more excited about being fingered, or that my girlish blue fingernails were fingering someone, even if it was me. Eventually I squeezed two fingers up my ass, but not very far, and while it felt intriguing, my fingers didn't get me anywhere. If I wanted to do this, I'd need some equipment. I barely even tried to restrain myself, and before long, I'd ordered an anal training set, in pink rubber, online along with some lube. I hoped I'd never move beyond the smallest, a slim three inch piece of rubber, and certainly not to the largest (a full six inch dildo). I don't know what had possessed me to buy a set rather than a single small toy. It had seemed cheap at the time, a bargain to get multiple toys for a discount, but I was slightly terrified that my subconscious had bigger plans than I wanted to admit. -------------------------------------------------- The training set arrived midweek, but I wanted to save it. If I was going to do this, I was going to do it properly, and that would require more time than I had in an evening. When Saturday rolled around, I got prepared. Shaved and showered, I repainted my nails (all of them) in crimson. I pulled on the pair of sheer black thigh highs I'd bought way back on my first girle shopping trip, and a black bra with a little lace on it, a more recent purchase. Then I went to work on my face, using all that I'd learnt from the tutorial videos. In the end, my complexion was perfect thanks to a layer of foundation. My eyes were had dramatic dark eyeshadow to fit the black of my wardrobe, my eyeliner winged out beyond the edges of my eyes, and my lips were painted with a liquid looking cherry red lip color to match my nails. Finally I slipped on my red pumps, six inches if they were one, with a two inch platform. The stockings made it easier to slide comfortably into them, my skin sometimes wouldn't slide on the leather to easily squeeze myself into the pumps snug fit with bare feet, and I had to pause to appreciate the bright red nails visible through the sheer fabric of the nylon. I had been plotting all week just how I wanted to do this, and had decided if I wanted the full effect, then the more exposed and undignified the better. I got on the bed on all fours, head lowered, and pushed my ass up, as if exposed for some imaginary man. I squeezed out some of my newly purchased lube into my palm, and reached back between my legs. I thoroughly lubricated my ass, fingers dipping slightly into my hole to make sure it got everywhere. Then for good measure, I lubed the smallest dildo from the set as well. Then the moment of truth, I reached back between my legs and eased the dildo into my ass. It wasn't terribly wide, so any stretching was no worse than my previous experiment with my fingers, but it reached much further than I'd managed before. It took a while of gently easing it in and out of my ass to start reaching it's full length. With my ass in the air, wearing black lingerie and full makeup, I couldn't help thinking towards stories and pictures of traps, transsexuals, and crossdressers I'd found online in the last few weeks. Was I turning myself into that? I bit my lip as the dildo reached a little further on this thrust than it had before, I could taste the lipstick. Only girls and sissies do this, I thought to myself, only girls and sissies taste their makeup while having a toy in their ass. Girls, and sissies, and me. I couldn't help talking dirty to myself, or maybe to my imaginary lover, as I screwed myself with the dildo. "Yes, fuck my ass. Spread my girlie ass with that toy. Doesn't Jamie look hot with that tool in her ass, doesn't she look sexy." I'd never gone by Jamie, always James or Jim, but it seemed right for this. "Doesn't her ass look great, and her long legs in those heels. If only she had bigger tits, she's only got small boy tits now. Wouldn't it be fun to fuck Jamie's tits too." That was new. I'd fantasized about my legs and feet, occasionally what the makeup I wore was doing to my face. I hadn't imagined myself with breasts before. But in this moment, in lingerie, fucking my ass with a toy, it felt right. What if this tiny padded A cup bra wasn't just an A cup, and didn't need to be padded. What if it was full with night firm titties that would sway with every thrust I used to push the toy into my ass. The mental image of me, on all fours, with a pair of boobs hanging into my bra cups overwhelmed me. I bit my lip again, the taste of lipstick seemingly overwhelming. I paused my manual abuse of my ass, I wanted to do something about this now, and then it occurred to me, I could. I stood up from the bed, leaving the dildo in, deliciously feeling it fill me, and move with me as I strutted in heels into the bathroom. I'd relocated the remnants of those first girlie bags filled with Annie's leftovers to the cabinet under the bathroom sink. I knelt, knees together, and pulled it out. Picking through it, I found what I'd been looking for. I hadn't touched it since I first found it, and it was still there, untouched, a fresh blister pack of Annie's birth control pills. 28 pills, 21 of which would be full of female hormones. I used my crimson tipped fingers to pop the first pill out of the pack. Holding it in my hand, I looked in the mirror. I looked remarkably feminine, though with short guy hair. My practice with the makeup had really paid off, and my slim physique was somewhere between young and flat chested girl. I might have even lost weight recently as I'd tried to use running as a distraction from all of this. I looked at myself, half girl already, holding the dangerous pill in the palm of my hand. Then I looked my reflection in the eye. "Jamie would be hotter with boobs. Jamie wants them, and she deserves them." My cock was at full attention, and I was acutely conscious of the toy in my ass. Then, deliberately, I said to my reflection, or maybe she said to me, "You deserve to have boobs." "No!" I was screaming inside my head. These aren't hormone replacement pills, it's dangerous to take them like this, plus this was way over the line, the sort of thing I might not be able to come back from, but whoever was running my brain wasn't listening. I picked up the pill, holding it up by my eyeline between red nailed thumb, and red nailed forefinger. "I should have boobs," I declared. I opened my mouth, stuck out my tongue, and carefully placed the pill in the center. I stayed that way for a moment, making sure I could see the pill on my tongue in my open mouth, between two liquid red lips. Slowly, they closed, and as my impotent inner male desperately tried to convince my brain that even now I could still spit it out, I saw my throat move as I swallowed. Then, almost as if taunting my reflection, or she were taunting me, I made a kissing motion with those cherry red lips and opened my mouth to show the pill very much gone. This was too much for me, the pill, my reflection, and my full ass were overwhelming. I'd begun to fondle my penis even as I was swallowing the pill, and seeing my empty mouth pushed me over the edge. I blew my load all over the countertop and sink, almost stumbling in my heels as my legs went weak. And just like that, the male part of my mind, the part of me not turned on at all by any of this was back in control, and horrified. What had possessed me to do that, to wear all this? I pulled the toy out of my ass, and ashamed, tossed it into the sink. This had to stop. But I still cleaned up the mess of my cum in lingerie, because even then it was still titillating. I still kept on my nail polish, and put on panties to sleep in after washing off the makeup and removing my stockings and bra. And the next morning, I still took the second pill in the blister pack while sporting a large erection.