one trapped night

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Status: Finished  |  Genre: General Erotica  |  House: Booksiesilk Classic Group

what would happen if you began to live openly and let go of your secret? for better or worse, max was about to find out.

-If you've read all the way through or enjoyed my story, please feel free to leave a comment.-

Max is the name that was given to me at my birth by my parents, although I have never really liked it all that much myself. Even as a teenager, I never really cut an opposing figure, standing a mere five foot and 4 inches and weighing a grand total of one hundred and ten pounds soaking wet. Looking in the mirror every morning greeted by the same sky blue eyes and angular face of mine, the one thing that always stood out to me, and much to my dismay, was that except for the straggly mop of light brown hair on my head I had no other body hair to really speak of, even after puberty. Now a grown man at the age of twenty-two, I have only grown two more inches, put on twenty more pounds, and still not much in the way of body hair, I give the appearance of a rather smooth and lithe figure of a man.

“Why am I telling you this?” you might ask. Well you see, I have a secret, one that I have kept close to me most of my life and have never really told anyone else and getting a clear concept of myself is an important part of my secret. As fate would have it, after a particularly eventful evening, my secret came to light……and I couldn’t be happier. Now I want to tell the whole world my secret and begin my life anew as a new person. It all began on a boring Friday night inside of my little apartment in the city……….

Comin home after a long day of work, I opened the front door of my small one-bedroom apartment that was settled in the more affordable part of the city. Upon turning on the lights, I was greeted with the familiar sights of my living room. There was the faux leather love seat that I sat to watch my modestly sized TV on most nights, to the left and off in a corner was the computer desk and my computer itself, and rounding off the area was my small dining room table with one chair situated across from an island bar and kitchenette on the right-side of the room.

To begin my weekend, I plopped myself down on to my sofa and turned on the TV. Flipping through the channels, nothing really caught my attention, tossing the remote onto the empty cushion next to me, letting out a loud “ppppft” from my flapping my lips I thought to myself, “well time to shower and get into something more comfortable.” Ambling of to the bathroom, I flip on the light, close the door and turn on my shower. While waiting for the water to warm up, I start to undress and put my work clothes in the near by dirty clothes hamper, then jump in the shower to wash up. Afterwards, clad in nothing but a beige towel wrapped around my waist, I head off to my bedroom to get dressed.

Turning on the light, I head to the dresser and closet to pick out my underwear and wardrobe, laying it neatly across my bed. Removing the towel from around my waist and tossing it aside, I turn to look at myself in the body mirror in the corner. My eyes roaming over my still lithe and hairless figure, down to my rather unimpressive sized manhood of just over six inches, I began to dress. I started off by pulling a pair of black silk stockings over my legs and up to my waist, then reached for a pair of by-shorts cut panties that wear light blue with little pink heart designs. “Ahh, my favorite”, I said out loud to myself, as I tucked my member back and slid them on over my slightly plump but still firm buttocks. Giving myself a light but approving smack on the ass, I continued to dress with a red and blue checkered mini skirt that barely covered the bottom of my buttocks when worn. I finished the outfit off with a lifter bra that gave the appearance of A cup sized breasts, a short-sleeved blue button down blouse tucked into my skirt, a blonde haired wig with long curly locks, and a bit of make-up topped with crimson red lipstick.

Looking at the final product in the mirror, a broad smile splayed on my face, as Max was no more, and Mira-Jane had appeared. I practiced my best version of a female voice in the mirror, which wasn’t all that hard for me, as I had a naturally lilted voice normally.  Afterwards, traipsed back into the living room to begin my nightly routine of drinking a bit of whiskey and taking selfies of my outfit. After a few drinks and a bit of self-encouragement, I decided tonight was the night that I would post a few of my selfies online, just to see how passable I really was. So, I hopped on my computer, went to a singles forum, made an account as a female, and posted the best pics I had taken of me in my outfit. Not long afterwards, I started to hear the pings of incoming comments on the pictures that I had posted. What greeted me was comments that men usually give women such as, “wow, what a beauty” and “hello there gorgeous”, to some even racier comments about my body and things they would do. I was excited that not only did I like the way I looked but apparently other people did as well.

After another big swig of whiskey from my glass, I decided that I would reply to one of the racier comments from a guy with the screenname BigCityMan. The conversation went very well, with a few thinly veiled but harmless innuendos and half-hearted requests for some more revealing photos. Eventually our discussion steered towards giving each other our real names and a request to meet out for drinks tonight. Sitting back in my chair, my heart was pounding at the thought of leaving my house dressed this way, with another shot down, I worked up the courage and told myself, “that you only live once” out loud and then began to type out my reply. I gave him the name Mira-Jane that I liked so very much, and he replied that his was John and that I should meet him for drinks at McCarthy’s around nine o clock. I was familiar with the bar, although I have never been there myself, I often passed by it while out shopping. Looking down at the clock in the corner of my screen, it informed me that it was ten past eight. Taking a few deep breathes, I agreed to the meeting and logged off to get ready for Mira-Jane’s first date. My hands were shaking slightly as I freshened up my lipstick and assured myself that I could do this, I grabbed my wallet and keys and bolted out the door before I could change my mind.

I arrived at the bar about ten minutes before nine, sat down at a stool, ordered a drink and secretly enjoyed more than a few approving stares from the gentleman around me. Not long after, I felt a strong but gentle hand on my shoulder and a gruff voice calling out, asking to confirm my name. Turning around in the stool, I was greeted with the sight of John, standing roughly five foot ten and around a hundred and sixty pounds of a slim but toned muscled body. He had firm features with cropped black hair, deep lime eyes, a short goatee to round off his face, he was quite attractive. I had to quickly shift in my seat, as I realized that my penis was becoming slightly untucked and semi-hard from my arousal after initially seeing him. Motioning to the empty stool next to me with a small wave of my hand, I managed to squeak out “please, have a seat”, to which he replied “gladly” with a wide smile. After about twenty minutes and three drinks in, John placed his hand atop mine, looked me in the eyes and said “you have a wonderful voice to match your beauty”, sheepishly looking away and mentally telling myself how glad I was to pass, I gave out a meek “thank you” in reply.

The night went on without a hitch, with us discussing more about ourselves and John throwing out occasional complements and flirtily touching my hands and forearm, time passed on until it was around eleven at night. The night crowd was wrapping up, as people were drunkenly stumbling out the door to head home, John steered the conversation and eventually posed the question, “would you like to continue this at my place, it’s not far from here” and seeing as I was rather tipsy from the drinks, approaching a drunken state, I hastily agreed and began gathering my things. Out the door and down the street we went, continuing to talk, as John cupped his hand in mine, wrapping our fingers around the others. Another fifteen minutes and we were outside the door to his apartment building, we headed inside and climbed three flights of stairs to stand outside of his apartment. Je unlocked the door, swung it open and motioned with his hand “ladies first”, I stepped inside. Turning on the lights behind me, John welcomed me to his home, it was well furnished and quite spacious for just one person to be living here. With a black sofa and recliner set a few feet away from me and off to my right was a full kitchen and the hall that led to the bathroom and bedroom laying across from the front door.

Not a minute after I had come in, had John laid his firm grasp gently around my waist and pulling my body tight against his, he began to kiss me deeply on the lips with his tongue slightly swirling around mine inside my mouth. Immediately my heart began to bound and my breathes came out short and labored, as my cock began to swell from the arousal beginning to become untucked, but at this point I was too drunk and horny to care. He didn’t notice as he began to kiss me more and his hands began to roam over my body, grasping and squeezing my plump tight ass. Moaning slightly, I began to become more turned on moment by moment until John took me by the hand and begun leading me to his bedroom. Once inside, he began to feverishly kiss me from my lips down to the nape of my neck while he started to undo and take of my blouse, shortly after it and my bra were on his floor as he played with my erect nipples, lightly pulling and twisting them in the tips of his fingers, to which I could only give out a satisfying moan.

He continued to explore my body with his lips, working his way down my chest, caressing every inch with his lips, until he was kneeling in front of me, ready to pull down and remove my skirt. Greeting him was my fully erect dick poking out of from the waistband of my blue and pink hearted panties and silk stockings, I was surprised when his only reaction was a slight chuckle and a reply of  “cute little panties” before pulling them off along with the stockings and taking the head of my small cock in his mouth. He began to slightly suck, sliding his mouth over the whole of my shaft before pulling back and sliding down again while firmly gripping my ass, I responded be clenching the back of his head and letting out a loud and long moan of pleasure.

After a few minutes of sucking my cock, he stood back up keeping it in his hand and slowly stroking it while motioning for me to begin undressing him, to which I happily agreed and began pulling off his clothes until he was standing in front of me fully nude and a hard dick that looked to be about nine inches. With a little apprehension, as I have never touched another man’s cock before, I took it in my hands and gently stroked it from head to base as it throbbed in response to my actions. Falling to my knees, I readied myself to suck my first cock and slowly slide the head in between my parted lips then began to slide it inch by inch down my throat until I was confident that I could take the whole thing, I began to speed up my rhythm sucking his hot throbbing cock faster and faster.

He let me continue for a bit before grabbing me by the arms and leading me back to my feet, then guiding me over and laying me down on his large bed with silk sheets. “Turn around on your hands and knees” John commanded and I could only comply, coming behind me and placing his hands each one on one of my ass cheeks, he pulled them apart and began to run his tongue over and around my bare asshole before pushing it inside and swirling it around. Moments of pure ecstasy began to rack my body, as waves of pleasure had me involuntarily howling and moaning loudly at the feeling of his slick tongue inside of my ass. He suddenly pulled it out and climbed onto the bed behind me, putting one hand on my waist and taking his cock in the other, John rubbed the head against the wet tight opening of my asshole, then without warning began to push inside. I wasn’t sure if it was because of the anticipation and pleasure or the alcohol, but I didn’t really feel any pain as inch by inch of his fully erect cock began to slide inside of me until I could feel the full length of his cock buried deeply in my ass and his balls against my thighs.

More moans of pure pleasure loudly escaped my lips as he began to thrust in and out until my asshole could easily accommodate his full size at a good pace, I gripped and pulled the sheets every time he fully slammed his cock inside of me and I could feel how hot it was and how it throbbed with each stroke inside of my ass. Both of us grunting, heaving and moaning the faster and harder he began to fuck me, until John suddenly pulled out so that we could exchange positions with him laying down and me climbing on top of him. Straddling his waist and grabbing his cock so that I could guide it up to and back into my asshole, I moaned yet again as he slid into my hole and spread my legs so that the whole of his cock could slide inside of me. I placed my hands on the bed at either side of his head and began to rock my hips, starting slowly at fist but quickly picking up the pace enjoying the feeling of him fully inside of me and the bouncing of my own cock with each movement, while he squeezed and smacked my plump little ass cheeks, each one eliciting a loud and contented moan from me as it landed. A few more moments passed before John clenched my ass cheeks tightly and bellowed “ I’m gonna cum” to which I leaned down and gave him a long kiss, looked him in the eye and replied “Blow your load in my ass”. I have never felt such pleasure as I did when the sudden rush of his cum began to flood inside of me, making me feel warm and full like I just ate a whole meal, the full excitement and pleasure causing me to grip the sheets tighter as I shortly blew my own load all over John’s stomach.

Out of breath and fully content, I rolled over to lay next to John throwing my arm around him to cuddle. We lay there for awhile longer, enjoying some small kisses as we talked, and I began to sober up a little. Curiously, I asked him “did you know?” to which he let out a small low laugh and replied “no, not right away” and “I still enjoyed the way it turned out”. Smiling warmly and happily, I laid my head on his shoulder as we both began to drift off to sleep. The next morning, I awoke to the sounds of cooking of in his kitchen, sleepily I rolled out of bed and went off to find his bathroom to straighten myself out and get dressed. A short while later, I joined him in the kitchen where we sat down and enjoyed a nice breakfast together while talking a promising to see each other again. He walked me outside and saw me off, as I walked down the street in the bright morning sun, still able to feel the remnants of his dried cum between my cheeks and down my thighs, I couldn’t help but to smile and exclaim out loud “Mira-Jane is here to stay”.

Submitted: June 27, 2020

© Copyright 2023 MidSyn. All rights reserved.

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Add Your Comments:


Amy F. Turner

What a story! Was not expecting how it to turne out the way it did but was glad the dude was so chill and went with it. Nice that M could be who M wanted to be. Free and find someone to be free with. It makes all the difference.

Sun, June 28th, 2020 10:28pm


Thank you for reading my story and i am glad that you enjoyed it and you are right it does make all of the difference and is important for the happiness and stability of ones mental self.

Sun, June 28th, 2020 8:55pm


This sort of thing always reminds me of that song, "Dude looks like a lady" by Aerosmith.
You should have had that playing in the bar. In any event, I've been to New Orleans during Gay Pride week (quite incidentally - Lord, my eyes were opened a new). There are men down there at whom you really have to look closely to know they are men. They look that good. I'm sure something like your story has happened many times in New Orleans, no doubt with different outcomes, but all the same - that moment of surprise!

Mon, June 29th, 2020 2:47am


Thank you very much for reading my story. The song idea would have been a good nod to the theme of the story, that would have been a great addition. Thank you for the idea, and if you don't mind i may use it.

Sun, June 28th, 2020 8:52pm

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