An Affair with an older married lady... and the aftermath...

[Shrouded]

I eagerly got into the car and started the engine, turning the airconditioning to full blast. Ann got into the passenger side. I sat there in anticipation.

"What are you waiting for?"

"Huh?"

Then I realised that maybe I should remove my jeans. I started unbuckling my belt when she stopped me.

"What are you doing?"

"Getting ready for you to suck my cock?"

"Me? Who said I'm giving you a blowjob?"

"Didn't you ask if I liked blowjobs?"

"Doesn't mean I'm gonna give you one."

"What?"

"Just drive."

I turned on the headlights and drove out of the car park. Maybe she felt that the car park was not secluded enough and wanted to bring me elsewhere.

"Remember the car park opposite the Changi Village Hotel?"

"Yeah?"

"Drive there."

I was puzzled. That car park was brightly lit and rather open. How could we do anything there?

"Why are we going there?"

"You'll see."

As I turned onto the road leading to the car park, I saw numerous scantily clad "ladies" hanging around.

Then it hit me.

"Why are we here?"

"Oh, I'm gonna pay a tranny to give you a blowjob."

I immediately slammed on the brakes. Thankfully there was no cars behind us.

"WHAT THE FUCK??"

"You like blowjobs right? So now I'm gonna get you one."

"Errrr....."

The idea of a guy, or rather half-guy/girl wrapping his/her lips around my cock and sucking me to orgasm was a mix between absolute disgust and curious anticipation.

"Why can't you suck my cock?"

"What benefit do I get if I give you a blowjob?"

"Erm. I'll eat your pussy?"

"Haha. Doesn't sound very beneficial."

"I'll make you cum?"

"Your self-confidence is sky high. What makes you think you're capable of even getting me wet?"

"Well..."

"The way I see it, if I give you a blowjob, you cum, go soft immediately, then fall asleep and I won't be able to do anything else."

"And how would a ladyboy sucking my cock make any difference?"

"Oh I get to watch."

"What?"

"I wanna compare. See if there's any difference in how they do it."

"Are you serious?"

"Don't tell me you don't have the balls?"

I never had the pleasure of being pleasured by a "sister" before, and somehow, I wasn't sure if tonight was going to be the night I wanted it to happen.

"You realise your car is a two seater right?"

"So?"

"So how are you going to watch? Normally they operate from within the car right?"

"Haha. You think that's gonna stop me?"

"I hope so."

"Haha. Wait here."

Ann got out of the car and approached a group of ladyboys and engaged them in chatter. I saw her point over to the car. One of them, tall, slim with enormous boobs waved at me. I waved back reluctantly.

I wonder what was stopping me from just driving off with Ann's BMW.

[cheongseeker]

Nice story so far. Keep going.

[hardworking48]

Great Story TS! Keep it coming!

[jomround]

I was laughing while having an erection reading the story.

Good script!

[1900]

Originally Posted by Shrouded

"Oh, I'm gonna pay a tranny to give you a blowjob."

That's an unexpected twist

[rooneyrocks]

Great story bro

[luvuass]

ts pls continue

[Mangaman]

great story with such twists. anticipating~

[Shrouded]

After barely 5 minutes of talking to the ladyboys, Ann returned to the car.

"Ok. It's settled. Are you ready?"

"Ready for?"

"To get your blowjob."

"By?"

"Oh damn. I forgot to get her name."

"Who?"

"The sister."

"What??? You weren't kidding???"

"Nope. But it won't be in the car."

"Then?"

"Drive over to the hotel."

"Which one?"

"The one opposite."

"Are you serious?"

"You want that blowjob or not?"

"Well....."

Ann placed her hand on my thigh, stroking it teasingly.

"I'm sure you'll like it. She's damn hot."

"Erm. Pre-op or post-op?"

"Oh. Is there a difference? I didn't ask."

"Great. What if she whips out a giant cock and wants to rape my ass?"

"Haha! I would love to see that happen too!"

"You're mad. Sick. Insane."

"Trust me. It will be a night you won't forget."

"The way I see it, it's gonna be a night I don't want to remember."

"Just drive over there and stop being a pussy."

I drove across the street with Ann's hand still on my lap. I sincerely hoped she was kidding.

Her gentle caresses were actually turning me on a little. But I knew that it would not be her that would be sucking my cock that night. Or maybe it was a test for me.

Maybe she was the type of girl who put guys through some sort of test before she decides to sleep with them. Test if their equipment is in working condition before they use it.

After parking the car we entered the hotel lobby. I wondered how Ann would be able to get a room at such late notice.

"What are you doing tomorrow?"

"Nothing?"

"Ok. Then I'll get a room till sunday. I need a vacation."

"You mean staycation?"

"Whatever."

She strode up to the reception while I took a short walk to the Cheers outlet nearby to get a drink.

As I was smoking outside the convenience store, plastic bag with condoms and lubricant in hand, she called.

"Hey. Where did you go?"

"At Cheers."

"Whatever for?"

"Condoms."

"The sister has condoms. But since you are there could you get me a milk tea?"

"Ok."

I wanted to tell her the condoms were for me to use on her but decided against it.

Each passing minute just brought me closer to the realisation that there was not going to be any action for me with her. I was only her companion.

Oh well, I never had a ladyboy blow me before anyway. Who knows. I might enjoy it.

[jomround]

Cliffhanger.

[Shrouded]

I headed back to the hotel reception and found Ann waiting for me at the lift lobby. She peered into the plastic bag.

"Why do you need those?"

"Just in case."

She reached in and grabbed the lube.

"Didn't know you liked anal. I forgot to check if shes a pre-op."

"You're hilarious."

"Yup."

She hooked her arm around mine and we proceeded up.

Knowing her extragavence, I should have expected nothing less than a suite. And I was right.

We entered and immediately I was taken in by the size of the room. This girl had money.

She put her handbag down on the dressing table and came up to me. She sniffed.

"Go take a shower."

"Ok."

I turned towards the bathroom.

"Want to join me?"

She gave me a sly smirk.

"I'll think about it."

I went into the bathroom and stripped. Seeing a bathtub, I decided to run a bath. I wasn't sure if it was a smoking room but I lit up and sat on the toilet bowl while waiting for the bathtub to get filled.

Suddenly the door opened and a naked Ann walked in.

"Oh you're running a bath. How sweet of you."

I just sat there dumbfounded.

While she wasn't supermodel hot, she had curves in the right places, especially her butt. It looked like doggy style would be very satisfying. Her breasts were not saggy, a small B cup that held firmly against her chest even without a bra. Her nipples were light brown and small. Sexual characteristics aside, what really caught my eye was her fair skin. It was creamy white everywhere, even where tan lines should have been. I caught sight of a few stretch marks on her thighs but who doesn't have stretch marks?

"What are you staring at? You've never seen a naked woman before?"

"Just admiring the view."

She came up and stood in front of me.

I ran my hand down her shoulder, stopping to cup her boob, then down the side and along the curve of her hips. She trembled slightly before slapping my hand away.

"Who said you could touch me?"

"You don't like it?"

She put her hands on her hips. I stared at her untidy bush. Eating her pussy might prove a little difficult.

"Why don't you shave or wax?"

"Wax? Hurts like hell. Shave? Lazy. You don't like an all natural woman?"

She sat on me. I felt my cock stiffening under my boxers but tried to stop it. I didn't want her to see how horny I was. I took another puff to calm myself and felt my erection slowly fading away.

She wrapped her arms around my neck and pulled my head towards her neck. It was definitely an open invitation.

I kissed her neck lightly, then sucked a little harder. I ran my tongue down her neck, tasting saltiness all the way down. I stopped at her collarbone, planting kisses on it before arriving at the top of her boobs.

She pushed me away.

"Ok. That's enough."

She got off, walked towards the bathtub, tested the temperature with the back of her hand, before sliding in and closing her eyes.

I lit another cigarette.

[cgha21]

huh.very boring story.Stop writing pls.....

[nuclearkid]

Great writing, bro. Enjoying your story as it pans out.

[HokkienPeng]

Originally Posted by cgha21

huh.very boring story.Stop writing pls.....

Have you wrote any? Fucktard.

[Botakhead]

Support for sharing your pent up frustrations waiting for a great release, cumming next would be more actions.