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Please go easy on me, this is my first story! ? I hope you enjoy! ?❤

For context I’m a 5’5″ bi-curious male weighing in around 200 pounds, a little on the chubby side yet still firm. I looooove crossdressing, but am waaay too shy to go out dolled up! Every now and then I get the strongest compulsion to dress up and go to town on myself, and this was one of those times. 

I woke up that morning determined; that night I was gonna treat myself to a date and have a little fun afterwards. My body was still smooth after shaving a couple nights ago, and my toes were painted a lusty glossy black. In the mirror I looked so femme, yet was slightly bummed I couldn’t flaunt it. With a pout I showered up and put on what femme clothes I could; I wore a toe ring on each index toe, a nude thong and nude sheer pantyhose with a cute silver anklet on my right ankle. Over this I slipped on my boy clothes, and headed out the door to begin my day.

Work was monotonous and dull, save for my thoughts on what I would be doing later that night. I already had my outfit planned out. I was gonna do an “ode to spring” with a long, sleek, navy blue sundress with a pair of cute navy blue peep-toe espadrille wedges to match. For makeup I was going with a smokey mascara and eyeliner, with a nude colored lipstick to compliment the nude hose caressing my legs. The whole thing would be completed with a long, wavy brunette wig. Thinking about it made my heart flutter and cock chubby; it couldn’t get stiff being suppressed by a thong. 

Work was done and I rushed home. I stripped out of my boy clothes, then grabbed lube and my anal beads. I pulled my thong to the side, and with a lubed finger I began to massage my asshole. I could feel myself blushing and breathing a little heavy as the massage turned to insertion. Once I was lubed up, I began to lube the beads. One by one I worked them into my ass; small, medium, small, medium, large, medium. Once they were in I breathed a sigh of arousal and with my buns nice and full, but there was still work to be done. I walked into the bedroom and found my sundress laid before me on the bed, with my wedges on the floor below. I felt my face get warm as I picked up the dress and swept it over my head, finding the sleeves and fitting my arms through. It cascaded down, hugging my tits and belly; it flowed just above my hosed feet. I then slipped into the wedges, sighing in delight as I spied my black toes peeping from their holes. I pulled the straps to my ankles, and walked back to the bathroom to do my makeup and don my wig. 

I looked in the mirror and immediately blushed; I looked hot! Sooo hot! I could feel my cock stiffen up and my ass twitch as the beads reminded me of their presence. I watched a movie, drank some wine, smoked some weed, and was ready at long last. I walked back to the bedroom, laid down some towels and grabbed one of my dildoes; it was eight inches long, and about an inch thick. I went to a wall, got on my knees and began to suck that silicone cock. I felt like such a slut as it filled my mouth, my tongue lolling around the shaft as my lips hugged and sucked it. Spit oozed out of my mouth, and I could feel my cock swell with arousal. This went on for about fifteen minutes before I felt ready to move on; I wanted to get fucked!

I went over to the bed and laid on my side, my wedges hanging off the edge. I pulled apart my thong and tugged on the loop of the anal beads. I could feel my ass wanting to hold in the beads more, but it was time for bigger and better things. I tugged again and felt a bead pop out, causing my cock to twitch. I tugged more and more, and the rest of the beads plopped out with each tug. Once they were gone, I could feel my ass wanting more, so I grabbed my smaller dildo and lubed it. It was about six inches and half an inch thick, and I started to press its tip to my anus. It didn’t want to go, but with a few minutes of massaging the hole with the tip, it accepted the full six inches. I sighed in delight as I felt it inside me, each stroke eliciting a bead of precum leaking from my bulge. I gently fucked myself with it for fifteen minutes, then set it apart. My asshole ached with pleasure, yet craved more; so I grabbed the dildo I sucked earlier and began to fuck that. It was longer, and had more curve to it; which was helpful in rubbing my prostate. I felt my face go flush as I moaned in pleasure, I could probably cum like this if I kept it up.

I did not though; I had special plans for how I wanted to cum. I got up, hole slightly agape, and positioned my sex machine toward the bed. On the end of it was another eight inch dildo, but this one was an inch and a half thick. I was breathing so heavy as I got on all fours, inching myself back until I felt it on my hole. I had to slowly work myself onto the tip, doing my best to relax and fit it in. With a sharp gasp the tip penetrated through, and I raised my ass in the air, gave it a wiggle, and sunk my head low as I turned the machine on. To feel a cock penetrate you and not have to use your hands is euphoric, to say the least. I couldn’t quiet my moans, and I started to push back on the machine. I sped it up and was being fucked at a vigorous pace, so vigorous I lost on of my wedges. My face was incredibly red and I felt so incredibly aroused, and my cock slipped out of the thong; it was just about time.

I brought my feet toward the edge of the bed, and leaned back. I slipped my cock behind me and laid it to rest on my exposed nylon heel. With each thrust I twitched, and could begin to feel precum ooze down onto my sole. The wondered of cumming on my own feet coupled with the fucking I was receiving was too much; I moaned even louder as my hole clenched on the dildo. It amplified everything that much more, and with each thrust my cum was fucked out of me, left to fall on my sole below. The machine was unrelenting and I felt my face go numb with pleasure as I felt more and more cum fall onto my hosed sole and toes. My balls were drained and I felt my cock begin to go limp;  the hot cum seeping into the hose, soaking my feet. I freed my cock and fell forward, cummy feet hanging off the bed, asshole gaping, aching still for more. I could not stand it, and ended up passing out for a few hours, dolled up, in a sundress with one wedge.

I’ve got to have solo date nights more often.

NSFW: yes

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