u/No_Fee5354

I'm an escort, and as such have no shortage of sexual requests from men with unfulfilled dreams.

Recently, I got contacted by a Canadian man who was going to be on a business trip in Munich.

He asked me if I offer service with a Strap-On, which I do. He initially proposed a three hour dinner date, but when anal play is involved, dinner may be a bad idea. So I suggested a two hour date, a drink at the bar and ninety minutes of private time. For the sake of the story, let's call him Hugh. The name is redacted of course.

We had agreed to meet outside of his hotel. When I arrived, he was already waiting for me. We kissed each other on the cheeks and I gave him a hug. I had brought our toys in a briefcase. "Hey, could you deposit this in your room before we go to the bar?" "Oh, of course, let me take that." As he leaned forward to grab the case, I whispered in his ear: "If you want to take a peak, the combination is 6-4-2" and smiled at him.

He grinned. "I'll be right back". He hurried to the elevator. Three minutes later, the elevator doors opened again and Hugh appeared.

We proceeded to the bar and chose a small table by the window. "Did you like what you saw?". He blushed a bit "Actually, I forgot the combination, I'm a bit nervous". I smiled "Relax. Everything is going to be fine. I promise!" and gave him a wink. The barkeeper took our orders and we ordered a couple of Caipirinhas. I noticed him taking a couple of glances at my cleavage. "Do you like them?". He looked like a child being caught in the cookie jar. "Sorry..". I laughed. "Don't be. They will be yours in a few minutes". He gave me a sheepish smile.

We had some more small talk, then I said "Why don't you finish that and let's go upstairs". He took a long draw on the straw and finished his drink. I took my handbag and took his elbow. "Let's go".

He walked us to the elevator and we rode to his floor. I could tell he was really nervous. I caressed his cheek and said "Relax. Everything is fine". He nodded, the doors opened and we walked to his room.

As he swiped the card and the door unlocked, we were met by cool air. He had put another card in the main switch so the AC would keep running while we were at the bar. "Oh, that's clever". "Yes, I hate it when everything turns off when you leave.".

My suitcase was sitting on the bed on the day blanket. I took his hands, moved towards him and kissed him. He put his hands around my waist and pulled me closer. We french kissed and started undressing each other. As he pushed the straps of my dress from my shoulders, my dress dropped to the ground, revealing the red underwear he had requested for me to wear. He grabbed my boobs through my bra and pushed them up. "You have got really nice breast". "Why don't you go ahead and take it off", I said, and turned around. He opened the clasps of my bra, and I pushed the bra against my body as i turned around. Then I dropped it to the floor, took his hands and placed them on my tits. He squeezed them gently and leaned in for a kiss. I grabbed his butt and pulled him close, his half hard cock pressing into my panties. "Let's hop into the shower", I suggested. I dropped my panties, Hugh slipped out of his clothes, and walked into the shower.

The warm water flowed over our bodies. Hugh was taller than me, i needed to look up to him. We embraced and slipped our soapy bodies against each other. I grabbed Hugh's cock and started stroking it. His cock started growing in my hands as we kissed and Hugh squeezed my nipples. We continued this for a few minutes, enjoying each other's touch and kisses. I turned off the water and said: "Let's go play big boy", and led him out of the shower by his penis.

I dried him off with the soft white towels.

"Nervous?" I asked him. "Yeah, a bit" he nodded. "You can always change your mind and we can just have sex you know. Just tell me." "No, I want this. I've waited for this a long time, he responded. I took his hand and led him to the bed. "Let's do it then.

My briefcase was still sitting on the bed. I entered the combination, popped the latches and opened it.

Inside, a strap-on harness, three different sized dildos, lube, cleaner and condoms. "Do you want to start small?" I asked him. "That's probably a good idea" he said. I took the small dildo out and attached it to the harness. I slipped on the harness, pulled it tight and smiled at Hugh. Pulling him close, I kissed him. He flinched a bit when the dildo touched his penis and we had a laugh. We took the sauna towels from the closet and spread them out on the bed. I smiled and told him "Okay, on your hands and knees now please". Hugh did as he was told. I took the tube of lube from the briefcase and sat behind him. "just try to relax, okay?". The lid of the tube cracked open with a pop. I pushed some lube out onto my index finger and gently started massaging his asshole. I could see him clinching his sphincter. "Shhhhh, everything is fine...". Gently circling my fingers around his asshole, I grabbed his cock in my other hand and stroked it gently. Then I put some pressure on his asshole with my finger, and he immediately clenched. "Try to release it for me". "Sorry, it's a reflex. I'm trying". "Go slow, just keep trying. Imagine that you are peeing".

I added more lube to his sphincter and felt him getting more relaxed. Then, a gentle push, and as he relaxed, my finger slid in. "Good boy!" I commended him. I started to gently finger him and tried to get as much lube Inside him as possible. "Are you okay?" "Mmm, yes" he muttered. Slowly I removed my finger, slipped a condom on the dildo and generously lubed it. "It's going to be a bit cold" i warned him. Placing the tip of the dildo against his asshole, I grabbed his cock again and gently stroked it. "Ready?". "Uh huh. Try it".

I pushed gently forward towards him. He tightened up. "Shhhh, just relax.". "I'm trying" he said. "Take your time, just try to pee." He did, and as he relaxed, the tip slid right in. "Ouch!" He tightened up again.

"Good, the tip is in. Let's just stay like this until you get used to it". He nodded and said "okay, okay ".

More lube flowed from the tube onto the dildo.

"Just push back into me when you feel you're ready". I caressed his back with my hand and gently stroked him with my other hand. He was taking deep breaths and trying to relax. "Okay" he said and pushed into me. The dildo slipped in slowly, bit by bit. "Keep going" I encouraged him. With a final push, the dildo slipped in completely. "Just relax like this for a while, allow your body to stretch for a minute. How does it feel?". "It hurts,. but it also feels good". "It's going to feel a lot better very soon".

Hugh said "Okay, I'm ready". I started thrusting, gently, with small strokes. Hugh moaned quietly and tried to match my movements. I grabbed his hips and started increasing my strokes. "Good?". "Yes....yes..... don't stop".

Precum started flowing from his cock. I angled the dildo down at his prostate. "Oh god..oh....ohh..shit.." Hugh moaned. "Does that feel good?" "Yes! Oh god. Uuuh..". I decided to step things up and trusted harder and deeper into him. Hugh was holding his breath and winced with each stroke. Now the precum was just flowing from his cock, soaking the towel below. Hugh reached back to me and wanted to pull me into him? "Harder?". "YES, yes please har....aaahhh". I repositioned my knees so I could thrust deeper into him, then grabbed his hips and started pounding into him. "oooooooohhh gooooood". Hugh collapsed onto his belly as his knees gave out. "Keep going, please, please! Don't stop!" he begged. I did as he asked and kept plunging the dildo into his ass. Hugh had buried his face into the pillow and started making muffled noises. I grabbed his shoulders, pushed myself onto him and fucked him as deep as i could. Then, Hugh moaned into the pillow and started twitching violently as he screamed into the pillow. I reached under his belly just in time to feel his cum shooting out his hard cock. It was already completely soaked in precum, and now ropes of cum shot out of his penis until he collapsed. I heard a muffled "Stop!'. He turned his head sideways out of the pillow"Stop, please, stop, don't move! Please don't move!".

I obliged and laid my body on his, the dildo still buried deep in his ass. I laughed. "Just tell me when you're ready, okay?". He was breathing heavily. "Just give me a minute... it's... it's too much right now ". "It's okay, take your time", I said, and planted a few tender kisses in his neck". We stayed like this for several minutes. I ran my fingers through his sweaty hair, my breasts against his back and caressing him.

"Okay, please pull it out really slow" Hugh said. I pushed myself up and pulled back slowly. "Okay like this?"

He just muffled Mmmh Hmmm into the pillow.

The last of the dildo slipped out, and I watched as his stretched sphincter remained slightly open for a few seconds as it slowly closed. Hugh still laid on the bed, face down into the pillow. I removed the harness, laid next to him and pulled the blanket over us. He turned to me, we pulled each other close and cuddled, exchanging kisses and looking into each other's eyes. "Are you okay?" I asked him. "Yes. That was unbelievable. I came really hard". "No kidding" I laughed and ran my hand through the big puddle of cum between us. "Seems you were saving for this, huh?". "Yeah, I didn't cum for a week before this.".

"Okay, let me do some aftercare for you now" I said. I wiped the cum from his belly with some wet wipes and removed the soaked towels. "Turn on your stomach again" I told him, "it's going to be sore for a day I'm afraid" i said, as i applied some Bepanthenol cream to his anus, gently rubbing it in. "That's okay, it was well worth it". "Well, I'm glad you enjoyed it".

We took another shower together in the time that remained. He wrote me a message the next day, thanking me for the time together. Unfortunately his business trip was a one-off, so he won't be returning again soon.