His Surprise Escort

Yes, Sir

Well within the first hour of my date we had already had s*x twice now. To say my mind was blown would be an understatement. After our adventures in the office, he kept a possessive grip on my hip the rest of the evening. There were quite a few more displays that got me all warmed up again but he waited to do anything about it until we were in the car.

Thank God there was a divider between the front and back. But let's just say there were fingers in places I never thought I would have fingers in. I had a total of five orgasms in the car and got to use my childhood skills of a pogo stick bounding if you catch my drift.

When I finally noticed that we were going father into the city he asked if I would stay with him tonight. I hesitated at first because we were definitely doing date five stuff when this was only date one. After a minute of thought, I figured what the hell.

His condo.... wow. I was pretty sure I had seen it on one of those shows on HGTV where they show off all the million-dollar apartments. He had the whole floor! The elevator came up in the middle of the apartment and on every wall were floor-to-ceiling windows.

There was a massive kitchen with a bar that could easily fit eight people. There was a walk-in wine fridge and I made a note to go in and see his collection some time. Off the kitchen there were actually steps to go down to a sitting area with built-in seating making a giant U shape, so no matter where you sat you got an amazing view.

He said that there was a button he could push and the floor would pop up with a table so this could be a dinner party table, although he has never used it. He didn't seem like the dinner party kind of guy anyway. On the other side there was another bar but this time an actual bar with any kind of drink you could imagine.

Another sitting area with a pool table and darts. You could feel this side was more of a man cave area. This then led into his office which had two doors to either go back to the living room/man cave or go into his bedroom.

His room was amazing! I wasn't sure what I was expecting but this wasn't it. It was decorated in a cool grey color and different shades of blues. His bed was much bigger than necessary for one person let alone two but I'm sure that allowed for room to play... There was another desk in his room and a floor-to-ceiling bookshelf completely full of books.

He then led me into the bathroom. There was an open shower off the side of the room with one of the shower walls being the window. Even in the bathroom, there was floor to ceiling windows. He did say that there was a reflective film on them so no one could see inside day or night. There was a giant tub that could easily fit four people and last but not least a steam room.

By the time he was done with the tour, I heard a ding from the elevator and he left to go check on it. Turns out he had ordered dinner for us and they were bringing it up.

"I hope you like burgers. The place downstairs makes the best ones. I wasn't sure what you likes so I just told them to give us different options for toppings and you can build your own," he said pulling me over to the kitchen.

The smell of them hit my stomach and I didn't realize how hungry I was until then.

"Help your self I'm gonna go grab a bottle of wine," he said walking away.

I decided to go for a plain burger so I didn't get a weird breath. I wasn't planning on sleeping over so I didn't have anything with me. I tossed some cheese and bacon and spread a little BBQ sauce on it as well. They even sent up fries so I grabbed a few handfuls which was a mistake because they were piping hot!

When he came back he set about getting us glasses while I sat down and waited for him. After he was done getting us wine he went and got his burger fixed up and piled it high with different toppings and came and sat down.

Before I went to even pick mine up he turned my chair to face him and pulled me in for a breathtaking kiss. I couldn't help the moan that came out and he deepened the kiss shoving his tongue everywhere. I finally had to pull away to catch my breath. We were both breathing hard at this point but he kept his grip on my neck.

"Thank you for waiting for me," he whispered against my lips.

Boy if that was a "thank you," I will have to remember to do more nice things.

He then turned to start eating. It took me a few seconds to get myself together after that but then I dug right in. He was right it was the best burger I had ever had. Even better than Charlie's but I would never say that out loud.

"Your place is amazing, but how do you get any sleep with all these windows?" I asked him in between bites.

"They are on a timer and the curtains close them selfs during the night so the sun does not wake me up. I like to enjoy the city lights at night," he said.

"That is genius! I really loved your room. It wasn't what I was expecting for you but it fits you somehow," shoving some fries in my mouth.

He just looked at me with a confused look and I just shrugged.

"I expected you to have more of a darker taste when it came to decorating is all," I said

"Well, to be honest, my mom did it all so really it's her fault. But it's grown on me," he sounds almost embarrassed about that.

"That's nice that you have such a good relationship with your mom. It shows that you aren't so big and tough on the inside just the outside," I said laughing.

"Oh really?" he said

"Yeah! Clearly, you are a..." I didn't even have time to finish saying what I wanted to say.

He grabbed my waist and picked my up tossing me over his shoulder.

"What the hell!!" I yell trying to hold in a laugh.

"I'll show you big and tough. I seem to remember that you earned some punishments tonight," he said running his free hand up my legs and under my dress.

I instantly went still and my breath caught in my throat. I was half hoping he forgot about that...

He walks into his room and tosses me on the bed.

"Don't move!" he says giving me a stern look.

He walks away going to a door I didn't notice before and comes back out a minute later with his clothes off except for sweat pants. I notice in his hand that he also has a tie...

Oh, God...

"Take your dress off," he said in a voice that gave me chills, the good kind.

I stood up to take it off and decided to put a little show on for him as well. I turned so my back was to him and I slowly pulled one arm out and then the other letting them fall down. If I was facing him he would see me completely bear on the front.

Then I went for the bottom and decided to leave my thong on as one more thing to take off. Once the bottom was off I could hear him humming or growled I wasn't sure but it made my stomach do flips and all the liquid in my body ran to my p***y.

"Stop!" he said as I reached for my thong.

"Leave it on," I felt like his voice was getting deeper, sexier.

I reached up for the necklace and took that off laying it on the end of the bed. I then bent over to take off my shoes.

His body was all of a sudden against my and he grabbed my arms pulling me back up.

"Leave those too," he said and then nibbled on my ear.

I leaned my head to the side giving him more access and moaned when he followed down my neck.

"Hold your hands out with your wrists together," he said against my neck.

Without thinking I did it and he wrapped the tie around it in different ways bring them tight together. He then spun me around and crashed his lips down on mine bringing a deep groan from me. After his tongue explored every inch of my mouth he pulled away.

"I think you get another two for teasing me," he said making my jaw drop.

"Have you ever been spanked?" he asked.

"No, sir," I said.

I thought for a minute about what he was gonna do. This was big on my dream list from all the books I have read. I knew I at least wanted to try it.

"Oh, my god are you gonna give me a safe word?" I asked with maybe a little too much enthusiasm.

"You read too many of those books. But yes you chose one," he said chuckling.

"Ok. It will be Home," I said with a little giggle.

"Why Home?" he asked with a confused look.

"Because if something ever happened that I would need to use it then that it is where I would want to go," I said.

It made sense to me.

"Well, then that will be a safe word we use only in the bedroom. I don't want to be worried if we are out and about that you will want to leave me by asking to go home," he said with a deep chuckle.

"I'm sorry. Should I pick another one?" I asked.

"No. I like it. It just helped me understand how far I can push your limits," he said turning me around.

"Now, lay on the bed face down and spread your legs," he said with command in his voice.

My legs instantly went jello. The anticipation was putting my body in overdrive.

"Keep your legs apart but come up on your knees,' his voice was sounding huskier.

I could feel his gaze roaming all over my naked body. I did as he said and the anticipation from what was about to happen was making me dizzy.

"You have a luscious ass. I can't wait to bury my d**k deep inside you," he said running his hands all over me.

He pulled on my thong causing it to be tight against my already swollen lips. I couldn't keep the moan back anymore. His words were enough to send me over the edge.

His finger started to lightly probe my back hole again. After the car ride home I was anticipating this even more. I pushed my butt back against his finger silently pleading with him.

All of a sudden my ass was on fire and I could hear him chuckling.

"Don't be greedy, Angel. You will get what's coming don't you worry," he said sending another slap across my other cheek.

The burning was making me gasp for air. It hurt, but God did it feel good. I could feel my body start to buzz and he landed two more slaps. He then rubbed my sore cheeks causing the tingling to spread.

"Oh, God..." I moaned out. I couldn't help it.

"That was only four. You get ten more. Ready?" he asked. I could tell his breathing was getting deeper.

"Yes, sir," I moned again.

He rained down two smacks and then tugged on my thong again. It just about made me come. The pressure building in me was about to explode.

Two more smacks and more tugging on the thong and it brought me to the peak I was needing.

"Oh f**k f**k f**k. I'm coming, I'm coming," my hips bucked involuntarily.

My juices gushed down my legs and he ran his fingers through my folds keeping my orgasm going. Then he switched hands and used the one that was well covered with all my juice and ramed two figures in my back hole without any build-up.

"Oh my god, oh my god, oh my god. Don't stop! Don't stop!" I yelled as another orgasm crashed down on me harder than any I have ever had before.

"Yeah, baby. Take what I give you. You like it hard don't you?" he asked leaning his body on mine.

I wanted so badly to touch him but my hands were still tied up. My hips were still grinding against his fingers. I never wanted this feeling to end!

"Don't think this means it's over. You still have more to go," I could feel his smile as he spoke.

I could hardly wait.

He let my body wind down a little before removing his hands from both holes, causing me to moan or cry I wasn't sure what sound I just made, but it made him chuckle.

He stood up and ran his hands over my butt again.

Four more smacks two light ones and two hard ones had me building up again for another orgasm. I could hear him breathing harder now.

"Your ass looks so good in red. I almost don't want to stop and just see how red I can make it," he said groaning that last bit out.

"Two more, baby. I'm gonna make them good ones," as he said that he shoved three fingers in my back hole and used his other hand to smack down hard on one cheek.

"Oh, Damien! Oh, oh," I yelled out arching my back.

He used his thumb to hook my thong and pull on it all while shoving his fingers in and out. My juices were running down my legs again. There was no stopping what was about to happen. His hand came down again on my other cheek and my body just flew in all different directions.

He kept ramming his fingers in my back hole and used his other hand to find my c**t and pinched it.

I screamed as another orgasm hit before I even finished the first one.

"I need more. This isn't enough," he said and his hands left my body making me cry out in frustration.

"Don't worry baby. I'm gonna fill you up more than ever now," he said while taking his pants off.

He grabbed my hips pulling me closer to him on the edge of the bed. He rubbed his tip against my hole and before I could beg him to do it he shoved inside me.

We both moaned out at the same time. I had never done this before the feeling of being so full was overwhelming. It took my breath away.

"You feel so good, baby. I'm gonna rock your world," he said moving his hips slowly.

My body had a mind of its own now and my hips pushed back to meet each thrust.

"More. Harder. I need more. Please!" I begged.

My mind was blocking out everything. Only this moment matters right now. The pleasure he was giving me was unlike anything I have ever had before. I wanted the pain. I wanted it raw and powerful. I was needy and feeling very much wanton.

His free hand left my hip and went straight to my folds. His finger was like a magnet for my c**t and he rubbed it lightly and inserted his fingers and curled them. He hit some spots I never knew were there and just lost it.

"Holy f**k! Don't stop, please!" I cried as his fingers moved faster.

"Oh, baby. You feel so good. I'm gonna make you gush!" he grunted as he picked up the pace with his d**k and fingers.

The pain from him being in my ass combined with the spot his figures were currently on built my orgasm to an all-time high.

He was right. I gushed.

"Oh, oh, oh, oh my god..." or moans came out at the same time.

His thrusts became slower and he removed his fingers to catch himself so he didn't fall on me.

I could feel m juices pooling at my knees. The bed was soaked now. I knew I should be embarrassed but I was so exhausted now I couldn't even care. My body was soaring. Wave after wave was still coming from my orgasm. He gave one last grunt and I knew he was finished. Filling me with his seed.

He stayed in me for a moment longer trying to catch his breath. His hands roamed my ass and down my back in a soothing motion. When he finally pulled out I was actually sad that it was over even though I was moments away from sleep.

"I'll be right back I'm gonna get a rag to clean you up some," he said kissing my back and walking away.

My eyes were already closed when he came back. A deep chuckle made them pop open.

"Just give me a minute to clean you up and then you can sleep, Angel," he said gently.

After he cleaned up my butt and legs he rolled me over and grabbed my hands. He untied them and kissed each hand and wrist, rubbing them to bring the blood back.

"Hold your arms up, baby," he said and he slid a shirt over them.

I could barely keep my eyes open at this point. He laughed picking me up and carrying me to the top of the bed.

Somehow he got us in bed and wrapped his arms around me. His smell was intoxication. If I wasn't so tired it would have turned me on...again.

"Sleep now, Angel," he said kissing my neck.

My body arched against him giving a tiny moan. The kiss sent a shiver down my spine. I was too far gone to sleep for it to keep me up so I made a quick mental note to jump his bones again in the morning.

I slept so well that night I wasn't sure if I would ever sleep this good again.