This story is for a reader who reached out to me with a suggestion recently.
It was a rainy Saturday night. I’d been talking to a woman throughout the week who wanted to meet up for a drink (and more, for a price, she’d implied) at a local hotel. After getting my room key, I quickly found her, sitting at the middle of the hotel bar.
She wasn’t hard to miss. She was already flirting with the bartender, who was eager to be talking to her. In her mid-thirties and with long black hair, she was dressed in tight jeans, black stiletto heels and a flowing, sparkly top, complete with a lot of makeup and big jewelry. She was definitely curvy, which I didn’t mind at all, but still athletic and her hips were highlighted by her tight jeans. I felt a pang I’d jealousy and excitement, as the bartender was clearly into her, too.
I walked right up to her and said “Hi, Jae.” Her eyes lit up and she gave me a kiss on the cheek. She wore bright red lipstick and some dark eyeliner that drew out her big brown eyes. “Hey guy, are you going to buy me a drink or what?”
So, let me pause here: Role play isn’t much of a thing for Jae and I- our sex life is fairly vanilla, but satisfying. This is a true story from about a year and a half ago, where we’d planned to do some light role play.
We opted for the “meet an escort at the hotel” scenario (pretty cliche, I know). We agreed ahead of time to meet at chain hotel a few miles from our place. The plan was to arrive separately, get a drink and just take it from there.
So I bought Jae a drink and we made small talk, trying really hard to pretend we’d just met. It didn’t last long and we broke “character” a couple of times, instead opting to talk about our regular lives.
“So, do you have a room here?” Jae asked, reassuming her character.
“Yeah,” I flashed her the room key.
“Good, do you mind if we go talk business there?”
Leaving the bar and on the way to the room, I told her how hot I thought she looked. She laughed and we both quickly fell back out of character. We agreed that the whole thing felt a little silly and entered our room.
“So, I really don’t think I’d be good at the whole escort thing” Jae said.
“I think you just have to keep them wanting to come back for more.”
“Well, that I am going do.” Jae said, (I think she’d slid back into her role at this point).
I sat up in the bed, sitting with my back to the headboard. Jae stripped down at the foot of the bed, unceremoniously pulling off her tight jeans, heels, jewelry and top.
She’d opted for some simple black brief-style panties and a black bra. I was secretly hoping for something a little wilder, but I was not about to complain. For the first time, I noticed a sparkles shimmer on her smooth, dark skin.
“Is that stripper glitter!?” I asked incredulously. She just smiled and laughed impatiently putting her hands on her wide hips. It accentuated her small cleavage and the shimmer of the body glitter on her torso.
“Alright, that’s enough talk- is your dick hard or what?” Jae asked.
I was and I quickly took off my jeans and underwear. Jae looked approvingly at my erection, doing her best to pretend she’d never seen me.
“Thank god you’ve got a nice dick,” she quipped.
With that, Jae laid down in front of me and started to give the tip of my dick soft, small kisses. I really enjoyed the sight of her hot red lipstick smudged all over me. She then gave me a long, soft, slow lick on the underside of my shaft.
It was incredible; I’m not exaggerating when I mean she took her time. For probably a minute and a half, her wet, soft tongue traced from my balls upward, her hot saliva dripping down me. I throbbed with excitement. She never broke eye contact- confident and sexy as fuck.
I then watched her trace her tongue in slow, teasing circles around the tip. It was minutes of absolute agony, I was practically begging for her to put me in her mouth, which she never did.
“Wait…we’re in a hotel room- why are we fucking on the bed!?” Jae asked suddenly.
Jae sprang across the room, sat on top the desk and removed her black panties. She was surprisingly wet and I quickly slid into her. Jae moaned loudly and I picked up the pace. She actually gasped and screamed as I started slamming into her. I was definitely turned on by the sounds of our skin slapping against each other.
Before too long, I was on the brink of exploding. I took a pause and leaned forward to eat her pussy. She tasted amazing and I slid two fingers into her. Making the “come hither” motion, I kept my fingers working inside her while I licked and sucked on her clit. Jae held tight into the back of my head.
“Ok, ok, my turn,” she breathed.
We left the desk a dripping wet mess. I sat in the desk chair, gesturing for Jae to kneel in front of me and give me a blowjob again. Instead, she turned around, gave her ass a little shake, lowering herself onto my dick. I loved every second of watching my length enter her pussy from behind. Jae knew it, too.
“You like that don’t you,” she muttered.
Her wide hips and curvy ass looked absolutely amazing as she writhed in my lap. She increased her pace and intensity, pushing back against me. She removed her bra and flung it across the room. I held her hips and slid my hands across her smooth skin, grasping her tiny breasts and feeling her hard nipples under my palms. I held on tightly as the chair slammed into the desk, which slammed into the wall.
I reached around to rub her clit and Jae moaned as I did so. I felt her hand reach over mine, pressing my fingers against her, much harder than I’d touched her. She gulped and breathed out “you’re gonna make my pussy cum.” I felt her shaking as she came. She’d slowed to a slow grind and, breathing heavily, she asked me if I was ready to cum.
Somehow, I’d held off orgasm while she rode me- usually the other way around!
“I want to fuck you on the bed again,” I demanded.
Jae laid on the bed on her side. I knelt between her legs and entered her, while she wrapped her leg around me. (We’ve seen the position called “The Pretzel Dip,” and I’ll give up on describing it- just look it up. It’ll be worth your time!)
I pumped in and out of Jae, reaching a great rhythm. The sight of her wide hips was incredible and I playfully smacked her ass. I reached up and played with Jae’s hard nipples and small breasts. “You’re so deep, this feels incredible,” Jae breathed. And that was it for me! I was going to cum seconds after she said that. “And I’m gonna cum,” I breathed. “Cum inside me,” Jae said back. I grunted as I came, not stopping as I felt myself pulsing inside her tightness. When I finally finishing cumming, I leaned forward and Jae and I kissed. Still inside her, we made out for several more minutes, her lips tasting sweet and amazing.
And that was our first attempt at role play- not terribly kinky or hardcore, but we loved every second of it. Hope our readers enjoyed!
Source: reddit.com/r/gonewildstories/comments/fin2n3/jae_keeps_her_client_wanting_more_escort_role
Very hot! Is she your wife?