Androgyny in the Park

I met Andi at the park one hot summer evening. My wife and I were there to have a picnic and take in a show, Much Ado About Nothing, performed on an outdoor stage by a local community theatre company as part of their 'Summer in the Park' play series. We arrived about an hour before curtain (there wasn't actually a curtain, but, you know: theatre), set up our folding chairs (in the shade, thank goodness), and quickly consumed our sandwiches with some chips and a bottle of red wine.

Partway through our meal, a family of four set up next to us, spreading a blanket out in front of a few folding chairs. I watched them set up, making sure they weren't too close (we like our space) but also not so far away that more people would squeeze between us. They seemed like a typical family: mother, father, middle-school age son, and...Andi. When I saw Andi, I wasn't sure what label to assign in my mind and had trouble looking away, curious and intrigued. There was a persistent stirring in my pants as I ran through the possibilities in my head, picturing what androgynous secrets Andi had to reveal.

Andi was a waif-like creature with short, blonde hair styled similar to my own, a soft, feminine face, skinny arms poking out from a baggy t-shirt with the name of a local liberal arts college on it, and short, hairy legs protruding from a pair of loose, black basketball shorts. The hair on Andi's legs was downy, wispy, not the coarse hair I had on my own legs. Normally, body hair would be a turn-off for me, at least for someone I was imagining giving my dick to, but with Andi, somehow, it didn't matter. It only added to the mystery.

I tried to focus my attention on my wife and let the family enjoy their evening, but I kept glancing over at Andi, unable to clear my mind of the cute enigma. When finished eating, my wife and I walked together to the public restrooms, wanting to pee right before the play began so we wouldn't miss anything. The urinals were occupied, so I went into the open stall and did my business, careful not to spray all over the seat, because that's the kind of guy I am. I zipped up, flushed, and unlatched the door, finding Andi waiting outside. I slid past, Andi giving me a quick smile before latching the door shut. I guess I had my answer. Andi was a young man. The urinals were vacant, which cast some initial doubt, but then I remembered the basketball shorts, which are pretty much impossible to manage at public urinals.

My wife and I met back up outside the restrooms and walked back to our seats. Not too long after we sat down, Andi returned with his brother and father. He sat on the blanket with his little brother, legs stretched forward, drawing my gaze. I stole glimpses of his face whenever possible, thankful for my sunglasses obscuring the exact direction of my gaze. He had such a pretty face, a face most young women his age would be proud of, I struggled to not stare at and ogle him, a struggle I mostly lost.

When the play started, things got worse. The sun set, so I had to remove my sunglasses, making it more obvious where I was looking. Andi refused to hold still, legs crossing, uncrossing, dancing in the periphery of my line of sight, always drawing my eyes in their direction.

Then we locked eyes. I was trying to get another look at his face, hoping to sear it into my brain for later recall, and he was staring right at me, smiling, knowing exactly what I was doing. I quickly looked away, but he kept getting my attention, rubbing his bare feet along each leg. He abruptly stood up and bent down to put his shoes on, his small, round ass only a thin layer of mesh and undies away from me.

"I gotta run to the restroom," he told his parents.

"Again? Okay, Andi. Want me to go with you?" his dad asked.

"I'll be fine, dad. I may be a while," Andi replied, trying to ease the concerns of an overprotective parent.

"Stomach?"

"Yeah."

"Good luck."

"Thanks, Dad."

I watched side-eyed as Andi walked off. When he was off the hill and on the footpath, he turned, winked at me, then walked towards the restrooms. I wasn't certain of what he had in mind with that wink, but I figured there was no harm in finding out. I looked at my wife, engrossed in the play, and clutched my stomach.

"Hey, hon," I started. "I'm having a bit of an issue here."

She turned to me, concerned. "Your stomach?" she inquired.

"Yeah."

"Well, you better go now," she said, urgently. "The restrooms close after intermission."

"Okay. I'll try to be quick."

"Sorry, babe. I love you. I hope it's not too bad."

"Yeah, me too."

I excused myself and made my way to the footpath, going the long way around to not get the attention of Andi's family. It was a bit of a walk to the restrooms, and I was trying to seem nonchalant, but I managed to gain a little, Andi only beating me by 10 seconds or so.

"The play boring you?" Andi asked when I walked in.

"There was another show I found more interesting. You?"

"We just did this for my college theatre, so I'm a little over it. Felt inspired to put on my own show."

"If your college ever does Twelfth Night, you would make a perfect Viola/Caesario."

"No sir. Not I!" he quipped. "I'm not sure if I should be insulted by that or not."

"Please don't take offense to it," I urged. "It's just that, until I saw you in here earlier, I couldn't stop wondering if you were male or female. Again, no offense intended. I just couldn't decide if you were the most beautiful boy I'd ever seen or the most handsome girl I'd ever seen."

"And?"

"Obviously the most beautiful boy, given where we're at. Although, I'd like to find out for sure," I answered with a wink.

"Which do you want me to be?" Andi asked, moving close, close enough for me to kiss if I wanted to, and I did want to, but I held myself back.

"Whichever you truly are," I told him, honestly not caring what anatomy lurked under his baggy clothing, hoping I'd get the chance to find out.

He grabbed my arms and roughly guided me into a stall, pushing me onto the toilet as he locked the door behind us. He was over a foot shorter than me, and probably weighed half as much, but the insistence with which he moved made his actions quite forceful.

"Come on, don't bullshit me!" Andi barked. "You're hoping for something! Which is it?" He stood inches from my face, straddling my legs.

"Honestly, it doesn't matter. You are whatever you are, and what you are to me is beautiful. If there's a cock between your legs, it will be beautiful, because it's yours. If there's a pussy between your legs, it will be beautiful, because it's yours. I just hope that, whichever it is, I get to see it...maybe even touch it."

Andi sat on my lap, facing me, and leaned in close. I immediately took the bait and kissed him, pressing my lips firmly against his, sliding my tongue into his mouth as our lips parted. I grasped his back, sliding my hands down over his slender ass, firm yet soft to the touch.

"We don't have much time," he panted taking my hand and guiding it up under the front of his shirt. His chest was wrapped in some sort of tape, but I was still able to discern the swell of small breasts bound beneath. "I haven't had surgery yet, but I've started on hormones."

"You are Viola," I said at this discovery, kissing him as I fondled his chest.

Andi broke our kiss and shook his head. "Cesario."

"Well I hope I get to be Orsino, then, boy!"

With one motion, I set Andi onto his feet and yanked his shorts down to his ankles, revealing his last secret, a thick, blonde bush barely concealing the plump lips of his pussy. Poking out from the top of those lips was the biggest clit I'd ever seen, almost a tiny, little cock tucked between his furry lips.

"I just have one question about all this, boy," I said, standing up, towering over him as I unfastened my shorts, tugging them down to reveal my throbbing erection.

"And that is?" he asked, reaching between us to grab hold of my steely six-inch cock. He clutched it firmly, out of lust or envy I know not which, squeezing me in his delicate hand.

"Do you enjoy having a man in your pussy," spinning him around to face away from me, pressing his face into the stall door, "or do you prefer to take it like a man?" With that, I traced the head of my cock between his round cheeks, noting the traces of hair that had started growing there.

Andi turned back to me, looking up as I loomed above him. "I've been so horny since I started taking testosterone. Then, having you ogling me all night, thinking about what I was doing to you, I need to cum so bad." He rubbed the head of my cock against his enlarged clit, swordfighting with me in the sexiest way imaginable.

I went in aggressively for a kiss, his lips meeting mine eagerly, tongue at the ready to intertwine with mine. I backed him into the door and stepped through his legs, one foot then the other, spreading his legs as I positioned myself in between. My cock was pressed between our bodies, against his taut, flat stomach, balls being tickled by his thick bush. I grabbed hold of one cheek with each hand and lifted him up, pinning him against the door with my weight as he raised up into the air. His thighs hugged my hips, holding him up to provide me access to his hidden treasure. The fuzz that had sprouted on his legs was different than what I was used to; normally when I was about to slide into a dripping wet pussy, the legs wrapped around me had been shaved smooth. These legs had the makings of something stronger, more rugged. Andi was transitioning and was well on the way to becoming a very beautiful man. I considered myself lucky to be where I was in that moment, enjoying that beautiful flower as it was just starting to bloom.

We continued furiously making out as I shifted my hips side to side, lining the head of my cock up with his pussy. I found my way by feeling for the wet warmth emanating from his little, pink secret. My mushroom, swollen with lust, slipped inside easily, his arousal almost as intense as mine, and the rest of my six inches soon followed. His bushy lips swallowed me whole, squeezing me every inch of the way in. When I ran out of cock to slide into him, his clit mashed into my crotch, fucking me as I fucked him.

I began thrusting into him, rattling the door and shaking the walls of the stall as my weight repeatedly drove him against the door. "Fuck, you're tight," I grunted. "You are unbelievable!"

"I've never been with a man before," he grunted, "only boys."

Andi's pussy was impossibly tight, sopping wet, and steaming hot, stoking the burning lust I'd harbored for him all evening, lighting my cock on fire with heavenly friction.

"Your pussy is incredible!" I sighed in his ear, chewing gently on his lobe as I thrust my rock hard cock forcefully into his slippery hole. Every time I pounded my meat into his cunt, I mashed his fat, swollen clit against my pubic bone, making him whimper.

The bathroom was filled with a cacophony of rattling walls, wet slaps of our bodies forcefully uniting, moans, and cries of bliss as I relentlessly fucked him, pinning his tiny body against the wall with violent stabs from my stiff prick. As the quivering within his body intensified, the searing pleasure rising within my own organ grew along with it, each savage thrust bringing us both closer to the inevitable.

"I probably should have asked this sooner," I started, clutching one of his downy ass cheeks in each hand, squeezing the taut flesh, fingers massaging deep into his crack, "but..."

"Andi," he squeaked, biting his bottom lip as climax began to overtake him. "My name is Andi."

The frustration of misunderstanding bought me a few seconds as I kept pistoning my cock in and out of his clenching cunt, fucking him right through his orgasm. "Nice to meet you, Andi," I said without irony. "I'm Justin. What I really need to know, though, is if I need to pull out."

"Cum inside me!" he demanded, locking his ankles together behind me, pulling me somehow deeper inside him. "The hormones will keep me from getting pregnant."

That bit of permission was the relief I needed, and I immediately obliged him with several powerful jets of cum, filling him with my thick cream. I held myself buried inside his pussy, now sloppy with both of our orgasmic releases.

As we both struggled to catch our breath, he began humping against me, grinding his massive clit into my thick bush.

"You need to cum again?" I asked, flexing my semi-hard cock within his tight cunt, squeezing even more cum into him.

"Ye-es," he whispered, pleading, his eyes closed as he focused on his pleasure.

I set Andi down and sat on the seat, watching as a stream of cum followed my cock out of his pussy. I pulled him closer, pressing his pussy right into my face, and began dutifully sucking his horny clit. It was two inches long, about a big around as my pinky, and, judging by his reaction as I took it into my mouth, VERY sensitive.

"Ohmygod!" he groaned with a start as I massaged him with my tongue while applying steady suction. He held the back of my head and pulled me tight against his crotch, unwilling to let me go before getting blown to completion.

I began probing his dripping folds with my fingertip, coating it in our cum. Knowing how much I enjoyed it when receiving a blowjob, I used that fingertip to massage his asshole, then, when he was right on the edge, pushed it in past the second knuckle.

"Oh, FUCK!!!" he cried as he began flooding my mouth with cum, mostly his, with bitter traces of my own deposit I'd made. I swallowed him greedily, my own lust returning already.

Then I did something I'd only ever seen done in porn: I stood up, mouth still sucking his pussy, and spun him around, my hard cock poking him in the face. He immediately took the hint and began sucking my cock. He was good at it, too, especially given the awkward position he was in, being held upside down in a men's room stall.

I devoured his pussy as I held him, helpless, against the wall in a standing 69. His aroma was strong; the masculine musk from his ass mixed with the familiar and unmistakable scent of an aroused pussy. I was drunk on the smell of his sex, lost in how good his mouth felt as he eagerly sucked my cock as only a horny man can, our bodies pressed together, the faint swells of his bound-up tits against my stomach. I kneaded his ass, once again probing a finger inside while sucking his clit like a tiny cock. Catching on quickly, Andi responded in kind, massaging my ass, pulling my hairy cheeks apart, and penetrating me with a slender finger in a progression so seamless I didn't even realize it was happening until his fingertip bumped into my prostate and I saw stars.

"Unghhh!" I groaned, my lips buzzing on his clit as I struggled to maintain focus on the pussy before me. I started pumping my hips, as much to feel his finger moving within me as to feel my cock moving in his mouth.

Intentions aside, the result was the same, I fucked myself onto his finger while simultaneously fucking his face, sliding my throbbing head right into his throat as a steady stream of sweet cream was milked from me. I desperately sucked at his clit, hoping to make him feel half as good as what he had me feeling.

At some point he added a second finger, and both rubbed my p-spot with every thrust, detonating fireworks deep inside. I fucked his fingers and face hard and fast, trying to release the tension he had built within me. So soon after cumming, though, it seemed like a second orgasm was impossible from oral, even the enthusiastic oral he was providing.

I needed to cum, and didn't have all night to enjoy the wonderful feeling of his mouth swallowing every inch of my cock. I released his pussy from my mouth and flipped him onto his feet, pushing him face first against the wall. My cock glistened, jutting lustily towards his sex. His ass was perfect, still the tight, toned ass of an athletic female, despite the few blonde hairs that had sprouted on the underside of his cheeks. I caressed it firmly as I moved myself close behind him.

"You can fuck my ass if you want," Andi relented, pushing his hips back against me, trapping my cock in his tight crack.

My cock twitched at the suggestion, an opportunity no man would pass up, but somehow, I resisted the temptation. "There are countless men I could fuck in the ass if I wanted to," I told him, "but so far, you're the only man I've met who has a pussy for me to fuck."

One well-aimed thrust and I was back balls-deep in his pussy, hammering into him like a man possessed. Indeed, I was as possessed by the need to cum as ever before in my life. I fucked Andi hard and fast, using him selfishly for my own pleasure, at this point caring little for his enjoyment of the experience. I squeezed his right asscheek in my right hand, guiding my thumb into his puckered rosebud, not because I thought he might like it, but because it looked sexy as hell.

"Fuck me hard, daddy!" he bellowed. Somehow, despite my selfishness, Andi was soon cumming, humping back into me even as I drove him harder and harder against the stall wall.

Maybe it was how beautiful he was, maybe it was the fact that he was young enough to be my own son, or maybe it was how wet and tight his pussy felt, but I was well on my way to filling him with a second load. I was vigorously working my thumb in his ass, relishing how tightly it gripped me, when I decided to take him up on his offer and fuck him like a man. Despite my earlier words, no man I'd ever met had an ass like his, and I had to feel it for myself. Who knew when I'd ever have such an opportunity again? Besides, my wife had a perfectly good pussy, but wasn't in the habit of letting me in her backdoor.

I withdrew from both holes at once and immediately pressed my glistening head against his tight asshole, still slightly gaped open from my thumb. My head forced its way through his narrow opening and instantly, the moment I was pressed flush against his cheeks, erupted.

"Fuuuuck!" I groaned, loosing all that remained in my balls into his impossibly tight asshole.

"Ohhhhhh," he sighed, his ass filled in an instant with cock and cum.

I held myself fully within him as my spasms slowed, one hand firmly gripping his hip, the other gently stroking the side of his face. "You're incredible," I whispered into his ear, thankful for the experience we'd both just shared.

"No one has ever fucked me that hard in my entire life," he confessed. "Even when I was a girl."

"Sorry...I guess I got a little carried away."

"Don't be sorry! It felt incredible. I've never felt so wanted before."

In that brief moment of vulnerability, I kissed him. It was firm, but tender, an expression of mutual satisfaction and gratitude, a parting kiss, each of us knowing we were unlikely to ever meet again.

As I let my shrinking cock slip out, I felt a pang of regret, not for what I'd done, but for all the opportunities with Andi I'd never have. I gave his ass one last longing look, seeing the gift I'd just given him leaking from his loosened hole, then pulled my pants up over my soggy dick, knowing the rest of the evening was going to be quite uncomfortable.

Andi pulled up his shorts and unlatched the stall. "Do you come to all the plays?" he asked.

"We'll usually come to each one once," I told him.

"We're at the first Friday of each," he said. "Maybe I'll see you there." With that he turned and walked out, his gait a little off due to the rigorous pounding I'd just given him.

I stayed back a few extra minutes, giving him time to get back so we weren't completely obvious. To pass the time, I pulled out my phone and rearranged my calendar so I'd be free for the first Friday performance of the next production.