One of the things that always pleasantly surprises me is how the women who meet me are adventurous – especially when it comes to anal. About 50-60% are keen to give it a go, or at least begins their first steps in exploring their back door via my massages.
For a place as conservative as Singapore, that’s quite impressive.
Of course, these ladies are mostly taking their first voyage into anal and often it just involves gentle probing with my fingers and not the full length and girth of a penis.
But once in a while, you get someone like Emily (not her real name, of course) who takes her first anal experience to a whole new level.
Demure and shy at first
Emily first found me on a forum and seemed a bit tentative when texting me.
“I’m really keen on trying this out for the first time but you seem to like curvy women but I’m not curvy at all. Will you still be keen to massage me?” she asked.
While I have my personal preferences, I don’t discriminate as I’m here to show the ladies a good time – no matter their shape or size. And I do like my slimmer ladies too!
I met her at the hotel and she looked like a regular girl next door. Kind eyes, slim built, a little shy but warmed up well when we started chatting. She wore a long skirt to go with her fitted top but that came off pretty quickly once we were in the room.
Just before the massage, we spoke candidly about what she was looking to try and why she decided to call me for this yoni massage. Emily said that she hasn’t been sexually active for the past couple of years but wanted to get back on the bandwagon to explore her kinks and feed her sexual appetite.
“I’ve always wanted to try a yoni massage and while we’re at it, a little bit of anal stimulation,” she said sheepishly. I was more than ready to oblige.
Teasing her body
Emily laid down and jutted her small perky ass up to me, calling out to me to be squeezed gently. With my hands oiled up, I started with a customary relaxing Swedish massage to ease her muscles.
I need not have worried too much about any tense spots because within minutes, her body was supple and relaxed as she gyrated and cooed with every touch around her neck, back and hips. As I moved my hands to caress her slim thighs, this shy girl parted her legs to allow me access to her inner thighs and view to her lovely snatch.
For a petite girl, she had a plump pussy with an engorged inner labia which looked ready for me. But like a good girl, she had to wait for her pussy to be played with. As I brushed against her pussy lightly when massaging her inner thigh, Emily moaned and motioned her hips towards me.
“Please touch me, daddy,” she lightly moaned. Well this was new to me. I was never called Daddy but I kinda… liked it?
I turned her around to start massaging her breasts and she looked like a different person. Not so shy any more but she held a smirk that was befitting a brat. I was never a big fan of brats because well…. they’re brats. Perhaps it also changes the power dynamic in there but I decided to just go with the flow.
“You sure you can tweak my tits hard enough to get me wet?” Emily teased. I wasn’t gonna let her off the hook. I twisted and pinched her nubile nipples hard to make sure she got what was coming. And you could see she liked it – not just the breast play but me responding to her challenges. She wanted it rough and the only way she could get me to do it was to push me like an annoying little twat.
Her inner demons brat revealed
As I took my time during the yoni massage to play with her labia and wet slit, Emily was goading me to fuck her, that nasty little minx.
“You wanna fuck that wet pussy don’t you? Why dont you just stick your big dick in there now?” she challenged me in between moaning whenever her clit was rubbed.
“You’ll get fucked when I tell you to,” I replied. Her pussy just squeezed up for a moment when she heard that. Two can play that game.
Then it came to warming her hole up for my fingers. I stuck one in and circulated it around her vaginal walls to activate all corners of her pussy. “Oh shit daddy, please don’t stop using your fingers.” She was delirious though I was only using 1 finger.
I slipped in another finger and began curling them up to hit her g-spot. Her eyes lit up but she couldn’t resist challenging me again. “Oh you think you can make me cum?”
Fuck going slow and being teased, she was gonna get what’s cumming to her. I immediately quickened the pace and increased the pressure as I clamped on that rough spot on the roof of her vagina.
“Oh my gooodddd! Daddy don’t stop!”
With my right hand vigorously sloshing in and out of her hole, my left clamped down on her neck with a vice-like grip.
“You’re going to cum for me and I won’t stop until I’m satisfied with how much you’ve cum,” I said to her in the heat of the moment.
Emily’s eyes rolled up to the high heavens and she went quiet. Her breathing deepened and her body tightened up. Before you knew it, her vagina was spasming all around my fingers – tightening up and loosening in waves and waves of pleasure.
I wasn’t going to stop.
“I want you to keep cumming for daddy. Don’t stop until I’m happy”
“Please, it’s so sensitive! Fuuucckkkk!” she cried. I wasn’t going to let up. A couple minutes of vigorous action and she tensed up again with legs shaking from the orgasm. She was having tears in her eyes and I didn’t want to let up. Minutes later her body went limp from ther third orgasm in a row.
I stopped and pulled out my fingers, not because she was spent but because my hand started to ache and cramp up. It was time to move up a gear. It was time to explore her ass, like she wanted.
Anus explored
I’m usually very gentle but I took exception with Emily. She told me prior that she has never had her ass explored and she was going to experience some new things today.
With my left hand free from aches, I dipped one finger into her wet pussy to lube it up. Without too much warning, I plunged it into her asshole with a corkscrew motion.
“Oh my god, fuck fuck, it’s in my ass,” she exclaimed. Immediately I noticed something different about Emily. Her ass was relaxed. It’s not uncommon that a sphincter tenses up when something enters it – even for experienced anal lovers. But Emily…. she felt like she’s been doing it for years.
“Are you sure this is your first time?” I asked.
She giggled. “Yes daddy. Why?” I stuck a second finger and she gasped some more.
“Because your ass feels so relaxed. It feels like it’s ready to take on a huge dick and it has done so for years,” I replied while moving my fingers in and out of her soft asshole.
“Why don’t you stick your dick in there to see how fresh my asshole is?” she challenged me again.
This time, I stuck my 2 fingers from my right hand into her pussy, giving her a double penetration sensation which she never tried before. Her body was shaking from the pleasure.
“Fuck me please, fuck me now” she said.
I did not wait for a second invitation. I slipped my fingers from her pussy but kept the ones from my left in her ass. I turned her sideways and slide my fully erect cock into her gaping snatch. It was heaven for both of us. I gave her long hard strokes while I kept pistoning my fingers in and out of her ass. Her moans and her eye rolls were filling me with ecstacy. I wanted to cum but I knew I wanted to fuck her more.
“Is that all you got? You think that was hard and deep enough for me? Is that all?” Emily said. This twat was gonna get it good.
I pulled out and turned her over to doggy. Her ass was jutting up, an invitation to slam her from the back. With one hand I held her head down and positioned my dick outside her pussy.
“You want it deep?” I asked. She muffled out some words which sounded like “uh huh”. That was all I needed. I moved from the crest of her labia up to her puckering asshole. She was going to feel all 6 inches.
I slid in my head slowly but noticed how relaxed it was in taking it all. Emily’s body was more than ready. I slammed the rest of my dick, balls deep into that ass.
It took both our breathes away. I kept pummeling that ass, pulling out halfway before slamming it all the way in. She was shivering and she forgot about being a brat for a while. That shut her up good, I thought.
She pulled away from me with the eyes of a deranged sex maniac. She pushed me down on the bed and squated over my cock. She plunged it back into her tight hole. Now, the brat was in control. She was popping up and down my cock like a pro. Her ass gripped all over it while her pussy juices rubbed all over me.
“You think that doggy was hard enough for me? I’ll show you how to fuck” Emily said.
She was wild. She switched from her up and down motion, to squatting to just grinding down. She was getting her money’s worth, trying every move she could think of.
“Daddy, do you think you can shoot deep enough in me? Are you sure you have enough cum?”
With my cock still deep in her, I pushed her down missionary style and grabbed her by the neck. “You’re gonna feel my cum deep in your stomach, you’re gonna get it good” I replied.
That smirk flashed across her pretty face again. And before I knew it, I was erupting. Ropes of cum spilled deep into her bowels as I continued to piston my hard member into her soft back door. We shivered as we collapsed on top of one another.
“Thank you daddy for giving me your cum. Was I a good girl for you?”
“You were very bad, but I like giving bad girls a lesson,” I said.
“Well next time, I want to swallow all that cum instead,” Emily said as she starting sucking my nipples.
Damn brat was trying to get me hard again. I guess I can’t disappoint her now………