Chicago For Two

We had planned this meeting for a couple of months. Chicago was going to be our place to be free to be ourselves without anyone else knowing about us or worrying about running into anyone. He traveled for business there every year to attend this conference. It was the perfect place. And it would be the first time we would be together in person.

We met online. He placed an ad on a site looking for a sub. I answered it. We are both married but our partners were not adventurous. Our connection was instantaneous and we knew we found our D/s partnership.

Our chemistry worked and we enjoyed the same things sexually. We also had common interests outside the virtual bedroom. Jake was a perfect Dom. He made sure to pleasure me and provide instructions that excited me. I wanted to please him. We talked regularly and had several video encounters. It was fun to play this way - it was safe from our spouses and provided many pleasurable ways to tease each other. Chicago was our indulgence to have a chance to play in person.

It was decided that we would fly through Denver so that we could travel the last leg together. He was waiting for me at my gate when I arrived. His stare was powerful and bore into my soul. I knew he really saw me - he knew my body by memory, he knew what I wanted, he knew what I needed, and was willing to give it to me. I walked up to him timidly with my cast downward. I was nervous and had butterflies in my stomach. When I got next to him my body reacted to him, I could tell I was getting wet immediately.

He bent to kiss me and hug me. As he did so he whispered "Samatha I need you to go to the restroom and remove your panties and bra. You will not be allowed to have either for the next 2 days. I want my girl as close to naked as possible."

I met his stare. He was serious so I went straight to the bathroom to remove them.

He was waiting for me when I came out. "Good girl." he said, "I like the white tank top. I can see your dark areolas. That pleases me. And that man over there," pointing to his right, "also likes the view."

I shivered because it excited me. I could feel the tingle down in my pussy.

Our final leg of the flight to Chicago was going to board in 40 mins. Enough time to get a drink. He ordered my drink; a red wine, Merlot. When he pushed it toward me to drink he said, "I can't wait to taste this in your mouth."

Yes, our chemistry was hot.

We boarded the flight. It was first class so just the two of us in our aisle. He had me sit at the window and he sat in the aisle seat. When we were getting our seatbelts on he told me to make sure and billow out my flowing skirt so that he could have access. I was wet and yearning for him as the plane took off for our flight of just over two hours. I didn't know what he would do.

After the flight attendant gave us a fresh drink Jake leaned over to kiss my neck. "You smell so good. I bet you will taste even better."

He placed his hand on my thigh after brushing my breast on the way down. My nipples instantly got hard.

"I think you liked that Samatha." Jake said.

I did. I was craving his touch.

He told me to open my legs as he started to put his hand under my skirt. It was resting on my knee for a moment but started to travel up. I couldn't believe I was going to let this man touch me for the first time in a plane. But I was ready for him. I was ready to give myself to him completely and follow his every direction.

As his hand continued to travel I sucked in a breath. I felt his finger brush against my pussy lips. I wanted more and made sure he knew it. I opened my legs a little more and he pushed inside my pussy lips to touch my clit. He rubbed it slowly, teasing me gently.

Jake let me know he approved of my readiness with a slight nod. "Very good."

I started to squirm because it felt so good but he took his fingers away.

"No, not yet my dear. I just wanted you to get a small taste of what is to come. Why don't you take a rest, you have a big night ahead."

I decided to take his advice and try to sleep a little. It was difficult at first. I was wet. I wanted him. I wanted more of his touch. I wanted to cum. But I knew we would be playing a lot at our hotel. I feel asleep.

Next thing I knew, I awoke to him sliding his hand up my skirt touching my pussy. "Darling, it's time," he whispered.

Indeed it was, the plane was making its descent.

Jake had arranged for a car service to pick us up and take us to the airport. In the car we had our hands on each other's legs and we kissed passionately every so often. We were hungry for each other.

At the hotel we checked in and requested just one key that Jake took. As we went to the elevator he told me that I would not need a key as I would not go anywhere without him. Another shiver of anticipation ran through me.

This man was in control and I loved it.

When the elevator doors closed Jake pushed me roughly to the back of the elevator and kissed me deeply running his hands up and down under the blazer I wore but over the tank top. He settled his fingers over my nipples and started to caress them. My nipples came out and he lightly pinched them as my back arched to meet him. I wanted him to lower those kisses to suck on my breasts. The door opened and he moved swiftly away to start down the hall to our room.

I was breathless and now I knew that going into that room would change my life. I would not be the same woman that went into it that came out of the room in two days. I was craving this man's touch and I was ready for his complete dominance over me. I was ready to give everything over to this man and let him do whatever he wanted to me.

Jake opened the door and let me in.

He went straight to the desk/dresser area to put his suitcase down. He called room service to order whip cream, strawberries, and champagne and looked directly at me when he ordered so I knew a little of what was to come.

As he hung up the phone he started to stride purposely toward me. He commanded, "Take off your skirt and remove your blazer."

I did as I was told and stood there in just my white tank top.

He was in front of me staring up and down at me, my body. "I like what I see. I like it very much. You are a beautiful woman."

He reached over to kiss me and while he was doing that he lifted my tank top to half it so that the edge rested just at my nipple, with a little of the areola peeking through and the underboob on display. Then he pushed me up against the wall and ran his hands along the side of my breasts, tracing the under breast with his fingers.

I sucked in a breath, his touch was electric.

He turned me around so that my breasts were pressed into the wall and started to run his hands down my sides and over my ass. He cupped my ass. "Your ass is beautiful. It's mine now."

Then he put his leg in between mine and pushed my legs wide apart. His hands started to move; one went to my breast to cup it and the other went lower to touch my pussy. The hand at my breast squeezed. As he did that he said, "These are my breasts," and the other hand on my pussy glided over my ass crack to snake around from behind and slide over my slit.

It shocked me how great it felt and my back arched deeply into his chest.

"This pussy is mine."

"Yes sir" I cried. "I am yours. My breasts are yours. My mouth is yours. My pussy is yours."

Before I could say anything else Jake grabbed a fistful of hair and pulled it toward him so my face was near his.

"And don't forget your ass is mine too." Jake said.

"Yes sir, all of my holes are yours." I responded.

He then took my shirt off over my head and turned me back to face him. I was completely naked except for my heels. Again he looked me up and down slowly, his eyes looking deep in my soul. I started to quiver in anticipation of what he would do next. At this moment there was a knock at the door. Jake ushered me into the bathroom and closed the door.

I could hear room service deliver our order. It was a little cold in the beautiful marble bathroom. There was a lovely deep soaking tub. This was not a motel. It was a luxury hotel. I was getting antsy when the door opened and Jake walked in.

"Samantha, I want to give you a bath."

He turned on the tub and started to fill up the tub with warm, steamy water.

There was a jar of bubble bath on the counter and he took a little to drop some of the vanilla scented liquid into the water. It started to foam immediately. He didn't put too much in, just enough to make it pretty and give a little coverage.

Then Jake took my hand and guided me to step into the tub. He pushed on my shoulders to a kneeling position which got my face to his cock level. There was a bulge there waiting for me. I knew I was meant to undo his belt and open his zipper.

I was slow, taking my time dropping his pants then I moved to rub my hand over his hard cock through his underwear. I touched the tip of his penis and it was wet. He was excited for me. I glowed. I continued my exploration by putting my fingers at the waist band and sticking them in. I started to glide his underwear down and when his cock was let loose it popped out right into my face. I licked my lips and opened my mouth. He guided his cock into my warm, wet, and waiting mouth. I immediately started to lick and suck him. He tasted wonderful. He smelled wonderful. I loved the feel of his cock in my mouth. It was a treat to be able to see it in the flesh. To taste and put my hands on him. I knew his body well but in person it was different.

I started to feel a drip going down my leg. I was that wet for him. I reached my hand up to take a hold of his cock and help build some friction while I sucked him in and out. He put his hands on my head and fisted my hair and pulled my mouth closer to take his cock even deeper in my mouth. I heard him moan and I started to suck harder. He started fucking my mouth. That's the only way to describe it. He kept pushing me deeper on to him so that I would deep throat him. I continued to suck and lick. I could tell he was building his climax. As he thrusted toward me and pulled my head to him he came in my mouth. I took all of him and swallowed every drop.

"Now it's time to clean you my dear."

He lowered me all the way in the bath and leaned me to the back of the tub. He took a sponge and dipped it into the water to get it full, then pulled it out and wrung it out over my breasts. The hot water streaming on my breasts felt so good. As he moved the sponge back into the water he put his hand down on my tummy and followed it to my pussy. He took the sponge and started to rub my pussy with the sponge. When it was filled again with water and my pussy juice, he took it out of the bath and again wrung the sponge of water over my breasts.

This time as he moved his hand to my tummy to slide the sponge back down to my pussy he leaned over and took a nipple in his mouth. He sucked on it at the same moment that his fingers found my pussy lips. My back arched toward his mouth. I wanted him inside of me even though this duel attack on my body was messing with my senses. I couldn't breathe and I couldn't think. I just had to enjoy it.

He continued to lick and suck on my breasts, occasionally pinching a nipple with one hand. The other hand stayed on my pussy as he fingered me and rubbed my clit. He was playing with my body as if he had known it intimately forever. He knew what I liked. He knew how to push me to build a climax and then switch the rhythm enough to have to start again. It was intoxicating. I was moaning and whimpering.

"Please sir. I want you inside of me."

Jake responded "Not yet my dear."

He continued to tease my pussy and then pushed a finger inside of me. I thought I was going to jump out of the tub.

"Oh my pussy is ready for me" he said.

I was.

Then he pushed in two fingers. I was just about to go over the edge and he knew it. He slowed just a moment and then decided to push in deeper and flick my clit at the same time. It was too much. I screamed out with pleasure.

"Oh that's what I want to hear, my pet." he whispered, "I want to make you moan. I want to hear you scream and scream for the next two days."

After I calmed down and started breathing normally, he finished cleaning me and pulled me out of the tub. He took a soft, fluffy white towel and started to dry me off very slowly.

It was sensual and sexy. He knelt down to rub down my legs. First down one and then up the other. When he got to the top of my leg he fingered me. Then he went to my back side and started to kiss my neck as he took the towel down my back gently. As he approached my ass he went over the butt and slipped a finger in my crack to trace it down to the pussy. It was heavenly and got me excited all over again.

Then he moved to face me again and rubbed the towel carefully over each breast making sure to caress the nipple lightly and trace under the breast gently. I have never wanted to get wet again to do it all over again like I wanted to at that moment.

That was a new experience for me to be so gently dried off. It was soft, slow, sensual and done with the utmost care and love of my body.

Next he told me to dress in the lingerie he had put on the counter. I hadn't even noticed he put it there. It was green to match my eyes.

He left me to get dressed.

When I put it on it felt amazing and fit me perfectly. It flattered me and I was confident for the next part of the night. It hugged my breasts and flared out from my waist showing off my hourglass figure. It came to just below the curve of my ass. The cups were lace so that you could just see a hint of the areola and nipple. It was classy like me and offered a hint of sex. Well maybe a little more than a hint.

I was ready to go face Jake and whatever the night would bring.

I walked out of the bathroom into the bedroom area. It was almost completely dark and the row of windows was expansive across the whole hotel room wall. The view was beautiful as you could see the lake and the city sky just beginning to light up.

I walk slowly to him as he is standing in front of the bed. I demurred my eyes and lowered my head when I got right in front of him. He lifted my chin to look into my face, searching my eyes to find the answers to all his questions.

Yes, at this time, he has complete control of me. He touches my face and then gently leans down to brush a kiss on my lips. It is sweet and sexy. I instantly start to feel the electric build up in my body. This man moves me. He moves my body in a way no other man has ever done and I know right then no other man will ever be able to like he does.

He starts to gently caress my body tracing around the lingerie. It makes me shiver and gets me excited. His hands glide to my breasts and he traces the circle of each of the barely visible areolas. Then runs his thumbs over the nipples. They pop out immediately for him to pinch softly. I suck in a breath. It's intense and I want more.

He moves his hands to my shoulders and runs them down my arms stopping at the wrists. In one motion he pulls my arms up above my head to meet each other and proceeds to tie them together. I can't help but push out my breasts to his chest to steady myself. The touch of my breasts to his bare chest shoots a fire to my pussy. I am ready for whatever this man is about to do to me.

Jake moves behind me and his hands trace back down my arms as he instructs me to keep them lifted.

He bends down to kiss my neck and runs his hands down to my ass to cup my cheeks. My ass lifted to his hands wanting more. Slowly he pushes me forward to the bed and instructs me to bend over and use my tied hands to steady myself. As I do that he pushes my lingerie above my ass so it's sticking out for his view. There were no panties with the lingerie. I understand why now.

He takes his hand to finger my pussy from behind. It's exquisite torture having him finger my slit and clit. My arousal is building and he can tell so he slows it down. Then he takes a finger and slips it in my pussy and it makes me moan.

I feel empty when he pulls it out and walks away from me. I don't know why but I know not to move.

When he does come back he places a blindfold over my eyes and then removes my lingerie from my body so that I am completely naked. It was a halter top that he could just unbutton at the neck and slip it down my body in a pile on the floor. Oh god it felt amazing.

He pulls me upright and turns me around to guide me to lay down on the bed. I was laying there naked with my hands tied above my head with a blindfold on.

He took both of my legs and yanked them open wide as he says, "I want you open for me."

I thought I felt wetness starting to drip from my pussy.

He starts showering me with kisses at my foot and then travels up my legs, to my thighs just inside next to my pussy, and moves over my stomach to my breast.

He attacks my breast sucking in a nipple. My back arches and I let out a little scream as the pleasure and pain is intense.

Then he goes to the other breast and does it again. This time he moves his hand to my pussy and puts a finger on my pussy lips slowly working my clit. His touch is powerful.

Finally he starts to trail kisses back down to my pussy. I had hoped he would become intimate with my pussy and I was not disappointed. He licks from my ass up my slit to my clit. Then he circles his tongue around my clit. I can't think straight. He works his masterful tongue over my body and my reaction is electric as I move around. I want more. He knows thi and keeps licking, tonging, and sucking. Then he sticks his tongue inside of my pussy hole and places a finger on my clit. I was just about to climax when he pulled away.

"Not so soon, my pet." He coos.

He turns me over to lay on my stomach and again yanks open my legs wide.

He pulls my hips up just a bit which makes my crack open up as I am an instrument he is playing.

I feel his weight leave the bed and it feels like a loss. I want him to continue his attention on me.

My pussy starts to ache for more touching and the cool air makes me aware of how sensitive my pussy is.

It seems like hours before he comes back to me but I'm sure it was only a couple of minutes.

I feel him back on the bed and hear a new noise. The noise was familiar but I couldn't place it until I felt it... the whip cream on my ass.

He licks it off slowly and then starts to place more on my ass but this time on my asshole. Jake was going to lick the whip cream from my asshole? He did and it felt amazing. I was begging for more.

As he licked it off he dipped a strawberry in my pussy and then moved up to my mouth and fed it to me. I had never tasted a sweeter strawberry.

He returns his attention back to my ass and puts another dollop of whip cream on my asshole.

As he licks it off this time, he sticks one finger inside of my pussy and puts his thumb on my clit. I scream out in pleasure. It's almost too much. I need a release. Now.

He puts in another finger and continues to lick my ass and touch my pussy. I let him know that I can't stop myself from cumming and he lets me. The waves are crashing on me over and over again. I can't breathe. He continues to stroke me and it makes me convulse. It's so sensitive and there is a hint of another orgasm but he slows down and removes his hand. I feel empty and filled at the same time. I want more. I want him inside of me. I want to feel him cum.

At this point Jake leaves me again but before he does he removes the blindfold telling me "I want you to see what is coming next."

He moves to his suitcase and brings back two things that he shows me. A buttplug and a lace black sub collar.

He is holding lube and starts to pour it on my ass and the plug. Then he inserts a finger in my ass to start to warm me up for the plug. It feels intrusive and welcoming at the same time.