Today, I was meeting a new client that wanted to experiment. As an escort, I was getting quite a lot of requests like that. Tonight, it was anal play, to be more precise, he wanted me to use a strap-on dildo on him. I got recommended for the job because all the girls knew I liked doing that. It was the ultimate domination, and power was what got me going. We set to meet in a hotel bar and I promised to bring everything we’ll need.
After settling on a comfortable yet stylish ensemble, I took a moment to check myself in the mirror, making sure every detail was just right. My reflection smiled back at me, mirroring the mix of excitement and anticipation. I ran my fingers through my hair, wondering if he'd notice the effort I'd put into getting ready. I wanted to look good for his first time.
As I walked into the hotel, I exchanged smiles with the receptionist and found a way to the bar on my own; all the professional escorts knew this place. My eyes scanned the room until they met his. A sense of relief washed over me as a genuine smile broke across his face, mirroring my own. I approached the table, and we greeted each other. He was quite handsome, and he had a nice deep voice. I couldn’t help myself and tried to imagine how hoarse his voice would sound after hours of moaning. He went to grab a drink for me, and I discreetly watched his arse as he walked up to the bartender. Oh, yes, fucking him will be a great experience. I could see how plump his buttocks were even through the loose trousers.
We talked a bit about his expectations, preferences and agreed on a safe word. We were very compatible, and his eagerness was truly adorable. After our drinks and all the topics covered, we went to his room.
I sat on the bed and looked at him with a flirtatious grin.
“Undress for me?” I asked him, tilting my head to the side.
As a professional escort, I learned all the moves that got men going. I knew no man could say no to that look.
I watched him slowly take off his clothes, he was a bit shy and kept averting his eyes from my careful gaze. He left the underwear on, but I raised my eyebrows questioningly, and he took his briefs off, uncovering the flaccid penis.
“Now, turn around,” I asked him, and after he did that, I added, “And bend over.”
He was very good at following orders, I liked that. His arse was a bit hairy, but firm and plum, perfect for anal. I smacked him lightly, watching it jiggle.
“Lie down on the bed,” I told him and scootched over.
Once again, he listened to me without any protests.
“Do you want to do 69 position?” I asked him, suddenly getting the idea.
“Sure, you can just get on top of me,” he smiled, shifting to the middle of the bed.
I lowered myself over his face and leaned forward to take care of his manhood.
He grabbed my hips, making me fully sit on his face. His tongue started moving inside me, sending shivers through my body. I grabbed the base of his cock and started licking the head, quickly waking it up. I continued sucking him until I could taste his pre-cum in my mouth.
"That’s enough," I said and stood up, "Stay, I’ll go get some toys."
I took a set of butt plugs, put on a strap-on and grabbed a bottle of lube.
“Can you get into a doggy position? On all fours?” I asked him, laying all the toys on the edge of the bed.
He got into the position, presenting me with his arse in its full glory. I knelt behind him and kissed his left buttock.
“Do you remember the safe word?” I asked tenderly.
“Yes, zebra.”
“Great, I’ll start with a little rimming, then fingering, and we’ll slowly work up the size. If you feel uncomfortable, or just want a little break, tell me,” I explained, “I’m here to make you feel good, first and foremost.”
“Thank you,” he said quietly, I could see him relaxing a bit.
I spread his ass open and licked his entrance.
He shivered, and his arse jiggled a little. I liked how responsive he was, it was like a kink of mine.
I started kissing and licking his hole, and then slowly slid my tongue inside. To my pleasant surprise, he moaned. Although very alluring, moans were very rare from men. It took me by surprise how verbal he was, even though I knew that I’m good at it, I ought to be working as a professional escort. I continued rimming him, inserting my tongue deeper and deeper. I was slobbering so much my whole chin was covered in spit, but I didn’t mind, oral sex was supposed to be messy.
Then, I took the bottle of lube and poured a healthy amount on his puckered anus. My finger circled the tight ring of muscles, before gently sneaking inside. His buttocks jiggled again, and I couldn’t help but imagine him twerking. I continued fingering him, but leaned forward to kiss his neck.
"Do you like it?" I whispered in his ear, sucking on his earlobe.
“Oh, yes,” he uttered.
I laughed, wiggling my finger inside him, "We’re only just beginning."
After I could fit three fingers inside him, I switched to a butt plug. I started with the smallest one of the three.
“Bend a little bit more,” I asked him, and he quickly obeyed.
“Push the plug out,” I said, and we repeated the process a couple of times.
I started doing the same with the medium butt plug, at the same time lubing my strap-on. It always felt weird for me, I didn’t mind using a mounted dildo, but lubing it up felt like I was jerking off myself, which was an odd construct. When I moved onto the last plug, I leaned a bit forward and started kissing his arse and these cute back dimples of his.
“OK, are you ready?” I asked when he was stretched.
“Yes,” he nodded.
I took out the plug, rimmed his hole for a while, just to relax him, and then poured more lube on it. Once I pressed the tip of my strap-on against his anus, he tensed up. I was expecting it, but most men have problems with it.
"Breathe in," I instructed him, rubbing his back reassuringly.
One gentle push and the head was in.
"And breathe out," I said, pushing the rest inside.
After the whole strap-on was inside, I used more lube and waited. As it wasn’t my real dick, I couldn’t feel is he was relaxed, but I knew I should wait a while. As a professional escort, I had anal sex before, so I knew how important that was.
He moved a little, fixing his position; that was my cue. I started rocking my hips, slowly fucking him. His sweet moans were like fuel for me, I could listen to this for hours. My thrusts were deep but careful and slow. Only when he started pushing back onto me, I sped up a little. I grabbed his buttocks, my fingers digging into the soft flesh, and he moaned even louder. Once again, I picked up the pace, taking pleasure in watching his sweet hole swallow my colourful strap-on.
“I think I’m going to,” he breathed out.
I wanted to reach out and jerk him off, but I didn’t get to, as he came hands-free.
“Oh, fuck, fuck, go faster,” he begged.
It was thrilling for me how much he enjoyed himself, I loved every second of it. This is a type of client that makes being a professional escort more than worth it.
He didn’t let me lead any longer, pushing his arse deeper and harder onto my strap-on. I let go of his buttocks and watched them clap over my dildo. The view was so attractive, that I reached from under the mount and started touching myself.
“Do you like it?” I asked him, gently slapping his tasty arse.
“Yes, I love it!” he moaned in response.
“How much?” I continued, this time slapping harder.
“The most, I’ve never felt like that!”
I slapped him again, leaving a red mark shaped like my hand.
“Yes, please!”
Another hit landed, this time I even scratched him a little with my nails. At the same time, my right hand was busy rubbing my pussy.
"Come for me," I told him, feeling my own orgasm looming around the corner.
We finished nearly at the same time, and collapsed.
“Thank you,” he muttered.
“My pleasure,” I laughed and kissed him again.
I spread his ass open and licked his entrance.