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Fulfilling a Fantasy

This is a brief tale about Jack meeting a beautiful transsexual, Ava. It's based on a real experience. It's a short, dirty episode. I hope you enjoy it, as well as Jack's journey with Michelle and Brad. Please leave comments if you do!

*

My nerves were frayed. It took a lot of resolve to remain on the train and not disembark at the penultimate stop before Bank. I could've swapped platforms and returned to my comfortable, quiet apartment, a bottle of cold beer, a shower to wash away the nervous odour and begin a long porn session dedicated to the fantasy I was on my way to realise: a date with a beautiful transsexual.

I remained on the train. I distracted myself by reading the adverts above the red handrail where only a few people were steadying themselves as the London Underground train completed its bullish passage. Ava was always at the periphery of my mind, and when we stopped in Bank, she burst to the forefront: brunette, blue-eyed, big-boobed Ava, my black dress-clad seductress.

As soon as the cool air of Autumnal England received me, I knew I would make it to her apartment. I followed the directions she'd given me. I paused outside her building, peering around to see if I recognised anyone -- it was the London metropolis in the wake of the rush hour, so I was obviously insignificant and unnoticed. I took a deep breath and with a trembling hand buzzed her apartment, 4A.

"Hello." I'd never heard her speak before. Her voice was soft and light, placed a register above where it normally resided.

"It's Jack."

"Come on up."

I was actually doing it: I was getting into an elevator to meet a transvestite I'd met on a dating app. We'd swapped photographs. I'd offered her one face picture and an array of the finest penis photography I'd done, all clever angles and dramatic lighting; she'd offered me photographs of her curvy figure inside a classic black dress, one of her big ass and wide hips sticking in the air and two selfies where she'd made herself up and styled her hair. Needless to say, I'd pounded my penis over all of them, swiping between them in a frenzy of masturbatory lust. The picture that I liked to explode over was a selfie she'd taken in her bathroom mirror, her bathrobe fallen coquettishly from her left shoulder, as she looked at her own picture on her screen. The sly and sultry smile on her face would bring me to an orgasmic rush.

As per my request, she was wearing the black cocktail dress from the photographs. Strapless, shape-holding, stopping just below the knee. She jumped behind the door so I only saw a glimpse of her before I entered the apartment. As soon as I did see her, I shook my head at my own good fortune and at my previous anxious self who'd sat trembling on the well-worn seat on the Underground. Now I was here, a winning lottery ticket wouldn't have had the power to the lure me away.

She led me into the living room and I greedily eyed her full, womanly ass. Her tits were smaller than I expected, but they were still there and larger than a lot of the girls I'd been chatting with. Most importantly for me, she was gorgeous, exceedingly feminine, even down to her slightest movements. She'd painted her toe and fingernails blood red, and she'd taken great care with her makeup. A crimson lipstick, that left a trace on my lips when we kissed, was the perfect cheery on the proverbial cake. She had strong facial features and a honey-coloured skin tone owing to her Greek heritage. As we kissed, I felt her heart thudding along as fast as mine. Understanding how nervous she was, helped me to relax.

Holding the tips of my fingers, Ava led me into her living room. She was cultured and well-travelled: heavy literature and ornaments were spread ubiquitously about the room. She'd lit candles and an incense stick. I spied an open bottle of Shiraz and a wine glass with the faint tattoo of her lipstick on the rim. She fiddled with the hem of her dress and brushed loose strands of her long black hair behind her ear: the wine must've been to temper her jangling nerves before I arrived.

"Thanks for coming," she said. "I've been looking forward to this."

"Me too! Nothing could've kept me away," I replied, attempting to sound confident, nonchalant. "You look amazing."

"Thank you. You're not so bad yourself."

"Nice apartment."

"Thanks."

"Have you met anyone before, you know, like this?"

"No. I'm quite nervous. Do I look OK?"

"You look phenomenal."

This was the extent of the pleasantries. During this thirty seconds of conversation, we'd been stroking one another's forearms and edging closer on the leather couch. We kissed. I felt the warm pall of the wine of her breath and tasted it on her tongue. My cock sprang into attention as soon as she probed her tongue into my mouth while her large lips massaged mine.

"God, you're unbelievable," I said.

She giggled. "Would you like a massage?"

She led me into the bedroom where more candles were burning, illuminating the room, bottles of massage oil and a bottle of lubricant. "Strip down and lay on the bed."

I obliged. I took my clothes off and lay on the bed while she went to the bathroom. When she returned, she appraised my body and smiled when she saw my swollen member resting against my thigh. "Very nice," she cooed. We kissed again as she fondly my cock lightly. I lay down and she rested on top of me. I grabbed onto her wide, supple ass and pulled her onto me. The bulge I felt pressing against my hip was impressive. I would have to wait to see it because she told me to go onto my back.

Ava playfully slapped my ass. I pressed my hard cock into the bed as she straddled me and covered my back in oil. She massaged my entire back, my bum and my legs right down to my Achilles. She whispered into my ear to relax. Feeling her hair brush my ear was as agonising as it was pleasant. She stroked around my ass hole and the back of my scrotum, ratcheting up the pleasure and the agony.

When she finished, and I was as shiny as a new car, she rolled me over and kissed her way down to my cock. I was extremely hard, stiffly at attention, pre-cum lubricating my tip. She licked this sweet goblet off my head. Then she sucked me off slowly, sensually. She licked and sucked on my balls and looked into my eyes as she did so. If her hair fell across her fair she would brush it away so she could keep her eyes fixed on mine.

"Mmm, you suck me so well, Ava. You mouth feels amazing."

"I love sucking cock. I love sucking this cock."

"Let me see you," I said.

She pulled the dress over her head. The breasts were smaller than I'd imagined, but they were pert and pretty. What wasn't smaller than I imagined was the cock that had burst free of a skimpy pair of black lace panties. An enormous, viscous-looking head was protruding, no bursting, from her underwear: a glistening pool of pre-cum had collected at the tip. It was the most masculine weapon on a feminine form. The stuff of my filthy dreams.

"Oh, my god," I mumbled unconsciously. "Lay down."

Once she was on her back, I positioned myself above her hips and kissed around the largest cock I'd ever seen in the flesh. It was also the hardest. Whereas mine has a certain dexterity, hers was as rigid and firm as a sprung-loaded length of wood. Pulling it away from her stomach took force: wrapping my lips around the widest part, where it splayed into a meaty midsection, took a moment of readjustment on my part. I sucked her big, beautiful cock and licked it from the base to the tip, a journey that took a few seconds as I tried to cover every inch.

She twisted her hips into the bedsheets and ran her fingers through my hair.

"Fuck me," she whispered while I dallied my tongue across the back of her drool-covered phallus.

We swapped position. I put on a condom, which she lubricated, and then she guided herself on my cock. She bit her lip as it eased into her, and then she began to grind against me, her enormous dong bobbing up and down as she began her rhythm. I took it in my hands and stroked it while she rode my cock. Her ass was tight. She tensed it against my cock so I could feel an extra tightness. She arched her back and began groaning as she explode her inner dimensions with my stiff member.

It only took a few minutes for her to orgasm, but when it came it came with fury. Her rhythm became hard and deep, and she shuddered as I wanked a small pool of cum from her cock onto my abdominals.

Once her orgasm had subsided, she removed herself from my cock. She took the condom off my erection, flung it into the bin and reached for the lubricant. She slathered it over my cock and jerked me off. I felt my orgasm building. The skin of my back became taut and then a fire radiated from my balls, up through my cock and throughout my entire body. She continued to stroke me, teasing me with tight wrapping strokes with both of her hands. I watched the red fingernails twists over my large, veiny member, and I looked at her semi-erect cock laying on the bedsheet, a large deflated balloon. When I came, she smiled and bent forward to receive a spurt of my warm, sweet seed into her open mouth. Two arching ribbons of cum lashed onto her red lips and she licked at it with the joy of a chocolate addict relishing a bar of the world's finest cocoa.

She ate as much of the cum as she could find. Then reached for her dress, the closest thing to hand, and began wiping the remaining cum and oil off my body. I stared at the ceiling and wondered why I'd been so apprehensive on the train; if anything, I should've run from the Underground stop to her apartment. Ava had also relaxed, and her graceful, feminine movements became more natural the more she tended to me and led me through the stages of our sex.

We returned to the living room -- where the smell of cum, ass and sweat wasn't so overpowering -- and we shared a glass of wine.

"The reality is much nicer than pictures," she said. "Don't you agree?" She tied to cords of her dressing gown together, enshrouding her wonderful body with the cream-coloured material.

"Much, much better. Pictures are nice, but this, that, was extraordinary."

We relaxed in our post-orgasmic glow, friends now that we'd ejaculated onto one another. Ava begin to tell me about her transformation goals, the pills she was taking and when she planned to tell her friends and family the extent of her goals. She showed pictures of the outfits she wanted to buy.

"There are some tough times ahead, but I know I'm doing the right thing. I'm Ava now." I complemented her not only for her appearance but for her bravery in becoming who she wanted to be, who she believed she was born to be. This imbued her with more confidence. She kissed me passionately and lay in my arms for a short while.

"You're already more sexy than many of the women I've been with."

She took the glass of wine she'd poured for me from my hand and placed it on her glass coffee table on top of a stack of women's glossy style magazines. She began rubbing my thigh and kissing my neck. Having my neck kissed is the most disarming thing a person can do: I was putty in her hands, the clay for an artist to mould.

"I want to suck your cock before you go! I want to make sure you think of nothing but me tomorrow when you're at the office pretending you watched The Walking Dead last night and weren't being a naughty, filthy, dirty boy with me."

Who was I to argue? She began my parting blowjob by kissing along the ridges of my abdominal muscles, then she slid to her knees and licked along my hard length from the wrinkled folds at the top of my ball sack to my velvety head.

I ran my finish through her hair. I stood up and began thrusting my cock in and out of her mouth, until she made a clucking, gagging sound as my cock entered her throat. All the while, she made eye contact. It was too much. My second orgasm rattled through me. My body jolted as more cum filled her mouth. She swallowed it all, and then squeezed a few more droplets from my cock.

"When can I see you again?" I asked.

She smiled and went to the bedroom. She returned with the dress and began wiping the cum off her neck.

"If you want to see me again, I need you to be a good boy and get this cleaned for me."

"What's that?"

"I need you to get this dress cleaned. Your cum is all over it."

"You want me to wash it?"

"Yes. Tell me you'll clean it, Jack."

"I'll...clean it."

"Good. That's what I wanted to hear."

I dressed. "I need my beauty sleep," she told me. She walked me to the door and placed the sodden dress in my hands. I couldn't believe I would have to go home with a cum-covered dress. In a few mad moments since my second orgasm, I'd become her errand boy. Her confidence had grown to the point where she kissed me and bit my lower lip painfully. I reached for the door handle holding my fingers against my swelling lip. She was completely naked and she didn't move from the open doorway. Her cock lay flaccid between her legs. I reached to touch it, horny autopilot controlling me, but she lightly slapped my hand.

"Clean my dress and you can play again." She smiled. "Yes, miss Ava?"

"Yes, miss Ava."

"Goodbye Jack, and do be a good boy."

"I'll try."

The door clicked shut behind me. I was left in a cold, fluorescently-lit hallway with my transsexual dream woman's black dress, wondering how fast I could get it cleaned and how soon I could get back into her apartment.

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