Not my first gay experience but it is about the first time I took a cock in my ass.
Hi there, at the time I was in my 18th year. A skinny short guy 5’6″ 110lbs. My hair is slightly wavy strawberry blonde. Back then I wore it collar length. Legal drinking age in Australia is 18 therefore it’s no surprise that this tale starts with me slightly inebriated.
Separated from my friends with no way to get home I started walking. I knew I would have to walk several miles along the a few of the main streets in the city before I could even start hitch-hiking. After several blocks the gaudy lights were fewer and further apart, one place still glowing like a beacon a block away was Player’s. the bare blubs rapid chase around the hording.
It’s a gay nightclub I’d been in there once before; it was a bet from my friends. they said I wasn’t game enough to go inside and get a drink; they put $20 up. As I’ve never had anything against homosexuals and wanted to win the bet. I charged up the fifteen or so steps, walked inside, sat on a bar stool. The bar maid, a guy obviously in drag, smiled at me.
“What-ch ya have sexy?”
“Bourbon and coke thanks gorgeous.”
She fluttered her hugely oversized eyelashes at me as she placed the drink in front of me. Pushing a $10 note across the bar I paid the inflated price. Taking the drink, I stepped over to the doors, looking down the stairway I could see my friends gathered. The astonished look on their faces, when I lifted the seven-ounce glass to my lips, downing it in a single gulp. After returning the glass to the bar, I walk down the stairs my arms above my head in a victorious parade. Stepping onto the sidewalk I demanded my winnings. A whole $10 after paying my bourbon, still a win is a win no matter how small.
As I get closer to the blinking light show I remember that night the atmosphere inside, the alluring women I saw. The sexy crossdressers, transvestites maybe a transsexual too. My cock started to rise as I imagined being with one of them.
From the opposite side of the street, I see an attractive woman walking down the stairs. She’s holding the hem of her long evening gown, keeping the flowing shimmering silver material from tangling around her feet. The split in the side of her dress shows her lace stocking tops, freezing to the spot I can’t take my eyes off the red headed vision of loveliness. She glided out the door, gracefully walking down the street towards the pedestrian crossing. Stopping beside the traffic light she pressed the pedestrian call button. That meant she would be on the same side of the main drag as me. Turning quickly, I covered the short distance to the pedestrian crossing, I managed to meet her as she stepped back onto the sidewalk.
“Hi, I could help myself when I saw you I just had to say… You’re gorgeous.”
Her reply wasn’t what I expected, but it didn’t deter me in the slightest. In a deep male voice completely at odds with the person, it came from, was the half statement and half question.
“You realise that I’m a man in a dress Darling?”
Not sure if it was my horny teenage brain or the alcohol I’d consumed earlier. My reply sounded alien to me but fuck you only live once.
“Wow! I didn’t realise but now you say that I’m even more excited. Can I have a kiss gorgeous?”
I look up at her pleadingly, giving her those big puppy dog eyes.
“Oh, you cheeky Boy. Do you think I’m easy or something?”
I knew she was flirting with me, she was having fun, that meant she might be interested. So, I knew I wasn’t going to be punched, that emboldened me.
‘”No, I don’t think you’re easy, unless you mean “easy on the eye” because you have that covered hands down. you most definitely are something special very special indeed.”
She smiled yes; she actually smiled at me. Disarmed slightly she pushed a stray strand of red hair behind her ear. An unconscious gesture for her but such a fucking turn-on for me.
“So, the pretty boy wants to kiss me, does he?”
Her smile returned but there’s was mischievous glint in her eye to accompany it. Not waiting for me to answer, she pulled me closer, her mouth open covering mine as she forcibly kissed me hard. Grinding her hips into my body as her hot wet tongue invaded my mouth, sparing with my tongue. Her hands gripped my ass cheeks; she pulled me against her as she dictated the terms of our kiss. I groaned into her open mouth as her hands gripped my butt harder, she sunk her fingernails into the soft flesh. Breaking the kiss, she took my hand in hers and half dragging me along the side street towards a carpark hidden between and slightly beside several high-rise buildings. It was secluded but still wide open to the street, leading me behind her she stopped beside a Toyota Hatchback. Opening the driver’s door, she reached in and opened the rear door.
“Sit down Sweetie, Mommy’s gonna show you something special.”
Her voice is mesmerising; I did what she told me to, turned around and lowered myself onto the rear seat, my legs hanging from the small compact vehicle. Lifting her evening gown, she swept it over her arm exposing her black lace Victoria’s Secret panties. A considerable bulge strained the thin material; she stepped between my legs.
“Are you ready for Mommy’s surprise Sweetie?”
My eyes wide I look into her green eyes, I know she wants to use my mouth. Fuck my life would’ve been over if any of my friends had seen me sitting in some cross dresser’s vehicle, mouthwatering as I debated on how long I could hold out before I opened that package looking me in the eye.
“Yes, Mommy. I want to see your surprise. I’m sure I’ll love it.”
Reaching out my hand settled on her black lace covered bulge, giving it a gentle squeeze. Slipping my hands higher I slide my thumbs into the waistband of her Lace panties. I pulled them down around her knees, being particularly careful going over her stocking tops. Her circumcised dick popped free almost hitting my chin, I estimate it was around seven inches long a little on the thin side for my taste now days but as a first cherry popping cock it was perfect.
“Suck it Sissy Boy. Suck Mommy’s dick you little faggot.”
Her cock bobbed in front of me like it had a mind of its own, the sight was mesmerizing. I was on autopilot; my hand wrapped around her shaft pulling her closer. Placing a hand on top of my head she guided me towards her straining tool. Poking out my tongue I greedily swipe away the large drop of pre-cum that had gathered. Pushing the tip of my tongue into you urethra trying to get more of the delicious salty Gurl nectar.
The pressure of her iron like grip guides my movements. I’m not in control of things, I’m not giving her head, she’s using my throat for her own pleasure. Her cock pounds into my compliant mouth, sliding into my throat on every stroke. before long she stops, pulling her saliva coated cock from me. The emptiness is unbearable I wanted her to cum in my mouth and was about to complain when she said.
“Ok Sweetie turn around Mommy’s gonna Fuck your sissy hole ya little slut.”
She hadn’t asked me if she could, no it was a statement she knew she was in control. She was going to fuck me; she stepped back giving me room. I didn’t say a word, I moved like an automation standing up, turning around whilst unbuckling my dress trousers, like a chastised child being readied for a spanking. As my pants pooled around my ankles she pushed me forwards. My hands flew out to stop myself from face planting into the vinyl seat, placing myself in the perfect doggie position. She stood outside the hatchback holding her cock in one hand the other one is firmly planted on my upturned butt, holding me where she wanted me. Rubbing her dick against my hungry sphincter brought a low moan from me while She laughed saying.
“Does the little sissy boy want his Mommy’s cock? Beg for it Fag boy, beg for your Mommy to fuck her little boi’s cunt.”
I wanted her so badly, the only thought in my head was please FUCK MY ASS I’d followed her hoping to be the one putting their cock into the other person. The way she took control excited me so much I was a bitch on heat, her bitch. Twisting my head back so I could look her in the eye.
“Please Mommy, please fuck your sissy boi’s tight virgin cunt. Please Mommy I want you to pop my cherry.”
As I said that she pushed the head of her cock into me, luckily, she’d spit lubed her tool beforehand.
“Oh! Mmmmmmmm, I bet I’m nice and tight for you Mommy. Please push your gorgeous dick deeper, fuck my sissy boi cunt until you fill it with your juicy cum Mommy.”
She slammed her dick into me; her hairy balls slapped into mine. My cock slapped into my waist with the force of her thrusting. Sliding me forward so my head was lower, my ass higher, and at a better angle for her. She redoubled her efforts seeking her own relief, her seven-inch cock flashed in and out of my gripping shitter. Slamming her dick into me balls deep she froze, I felt her dick throbbing in my ass as she pumped her cum into my no longer virgin hole. She grunted in my ear.
“Ugh, Ugh, Ugh Fuck your pussy is so fucking tight, you sissy bitch you fucking drained me.”
Pulling her cock out she grabbed a handful of my hair. She literally pulled me up from the seat using my hair.
“Hey! What the fuck?”
Grabbing my pants I stood, pulling them up and buckling them. Looked at her dumbfounded., I expected an explanation. But again, what she said wasn’t what I expected
“Fuck off fag boy.”
Without another word she got in her hatchback and drove away I never saw her again. I went back to the night club a dozen or more times, it was quite fertile grounds for sexual partners. I met a nice quite kinky 40yo lady whom I had a fling with, several crossdressers and one very cute transsexual.
All the rumors about having a cock shoved up your arse supposing to be painful, well my experience was remarkably different. I honestly don’t remember any pain, just a delightful full feeling then the exquisite sensation of having an experienced top bumping your prostate as they pound away at your willing ass. Just like every good bottom should
I may write about some of the fun the patrons from the night club and I had in another story all depending on the feedback I receive.
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