June 12, 2022

So this is Sunday morning. I worked last night and did some overtime with Mr. Santiago. It was not quite what I expected from my older Italian boss. I did not know there was a furnished apartment above the shop. I worked the busy Saturday night like I normally do. We were slammed. Mr. Santiago told me to stay, saying we had to talk after we closed. The rest of the staff thinks I was going to be disciplined for something I did. I had no idea how right they were. 

We locked up and everyone left. I waited in the office. He came in being his usual grumpy self. 

Being abrupt, “Come with me.” He leads me out the back door and up the steps that are in the back. I had no idea it was still in use. 

He unlocks a door and we enter. He locks the door behind us. There are two doors. One door, on either side of the short hall. He goes through the door on the right. As I look around the room. I see a couch and a large recliner. There are also a few things I have never seen. Something that looks like a saw horse, a large X, and a pole with chains hanging from it. 

There is a small kitchen, a bedroom, and a bathroom. I can’t see what is in the room from where I was standing. 

“Ashleigh, strip. I will discipline you first for having sex in the kitchen. That was very unsanitary. Luke knew better and you should have as well. Everything was on camera. “ 

I swallow and nod. My heart is racing in my chest. His demeanor is different. “You are right Sir. I should have known better. I am sorry Sir.” 

“Thank you. Nevertheless, strip now!” He looks me up and down. Arms crossed over his chest. 

I do as he has commanded and strip. I lay my clothes on a chair neatly. Standing before him naked. He walks around inspecting me. He runs his fingers through my hair and pulls, yy head goes back. 

“While you are in this place you are mine and do all I say, or there will be consequences.” He spanks my left ass cheek hard. It stings.

He grips my neck and leads me over to the saw horse. It is padded. There are pads for my knees and my hands. “Lay on the bar.” 

I do as he says. I am speechless. I have no idea what I am in far. He fastens leather cuffs to my arms above my elbows, then to my thighs. My hips hang off one end and my head on the other. 

I can hear him behind me. He has opened a cabinet. I can’t see him. He rolls a cart next to my head. I can not see what he has on it. I am breathing hard. My heart is racing. I have never been so restrained before. I am exposed and helpless. It is exciting and scary at the same time. 

“I am going to take it easy on you since it is your first time, I think. “ He kneels in front of me and shows me a wooden handle with straps hanging from it. “I will use this flogger on you first, then my hand. “ He stands up, still in front of me. “Look at me.” I do and he strips in front of me. His cock seems a bit bigger than the other night and harder. 

He grabs a hand full of my hair. My lips are made part. He pushes his cock into my mouth. He slides it in. Suddenly I feel the straps land on my back, stinging. I groan around his cock. He starts to slide his cock in and out of my mouth. The strands hit my back again. He spreads it out. My back is stinging and feeling warm.

I am not sure how long he used my mouth and flogged my back. It seemed forever and not long enough at the same time. My head was spinning. He pulls from my mouth. I am breathing like I sprinted a mile. He does not say anything to me. He walks to the cart. I can see him out of the corner of my eye. 

“You did very well. I think you are a natural slut and submissive. I am going to enjoy you.” He grabs my hanging left tit. Fingers knead the flesh.

“Thank you, Sir. This is very different for me. “ I gasp as something is clipped to my left nipple. He walks in front of me and out of my sight. He grabs my right tit and kneads it roughly. He clips something to my right nipple. They both sting a bit, but not overly so. 

I feel his hand sliding over my ass cheeks. Then I cry out as the flogger strikes. The strands cover my ass. He has hit a bit harder than he did my back. I feel my ass getting warm and start to sting. 

He stops. “Ah good. Your ass is all warmed up. Now for the spankings. This is for having sex in a sanitized prep room. Count the swats, saying Sir, after each swat.” His hand was on my ass rubbing it. 

I nod my head up and down, “Yes Sir. “ I tense waiting for the first strike, no idea how many I am getting. 

I cry out at the first strike. “One Sir!” it was loud and stung. He did it again in a different spot. “Two Sir!” He moved his hand and spanked me a total of five times. His hand hits a different spot each time. 

My back is slightly burning and my ass is burning. His hands are on my back. This time he is rubbing a soothing oil into my skin. It feels good. I let out a sigh. “Mmmmm, Sir. That feels good.” It feels even better when he rubbed the lotion into my stinging ass. 

He is using both hands to rub my ass cheeks. “Aftercare is essential. So is this.” He slams into me from behind. He is very hard. 

I cry out not expecting it. My head comes up. He does not stop. He grips my hips hard and starts to pound into me. I had no idea how on edge I was. It was not two minutes and I was cumming. He leaned over my body and reached down to my tits. 

He removed the clips on my nipples and they started to tingle painfully, mixing with the pleasure of the orgasm. It was exquisite. My orgasm got even more intense. 

Mr. Santiago kept pounding into me. His body is on mine. Hands groping my tits roughly. Nipples were being pulled and pinched. I started to squirt. I felt like I was drifting. 

I came back to Earth and he was still slamming his cock into me. He is keeping me on the high. He lets out a grunt and slams in deep. I can feel his cock swell and pulse in me. He erupts and his warm seed coats my pussy. It makes me cum again. My pussy is convulsing milking his seed from him. 

He collapses on my body still on the bench. We are both breathing hard. I lick my lips. “Sir, Sir. That was intense. I had no idea “ 

He pulls from me. Cum seeps from me. “That is BDSM. It can be very intense. It can get even more intense. “ He releases me from the bench and helps me up. He walks me over to the recliner. “Wait right here.” I stand there waiting as he goes to the kitchen. He comes back with a bottle of water. 

He sits on the recliner and pulls me onto his lap facing him. I am straddling his hips. He opens the bottle and takes a drink. We kiss and share the water in the kiss. It was the most erotic kiss I have ever experienced. We kiss like that several times until the bottle is empty. 

He puts his hands on my hips and helps me slide forward. I feel his cock hard beneath me. I reach down and line him up. With his help, I impale myself onto his hard again cock. I hiss feeling him slide into me. 

“Ohhhhhh….oh that feels good. “ I start to ride his cock. He keeps his hands on my ass directing me to go up and down on his cock. My tits in his face. 

He slides his hands up from my hips to my tits. He takes one in each hand. “Move faster kitten. Faster and don’t stop.” I do as I am told. It feels so good. I never thought a man his age would have so much energy. His fingers dig into my flesh. He is rough with my tits. Fingers pull, pinch and twist my nipples. 

He takes a nipple into his mouth. I stop bouncing and start to roll my hips. It changes the way he is sliding in and out of me. I start to breathe hard. God, I am going to cum again. It does not take long and I am. My pussy clenches his cock tight. Juices flowed from me. 

He stops me from continuing to ride him. “Turn around. Your back to me. Ride me until I cum in you again. Won’t take long.” 

I do as he says. I slide off his cock and turn around. I am leaning forward. He guides me down on top of his cock. I am impaled again on his hard dick. “Ohhhhh fuck” I brace on his knees. My feet are on the floor. I go up and down on his cock.

I am going slow at first to get used to the new position. He slaps my ass and growls. “Faster slut. Ride me faster.” He slaps my other ass cheek. I start to ride him faster. His hands stay on my hips. 

When I start to slow down he slaps my ass to make me go faster. I yelp with each swat on my ass. It does not feel the same as the punishment spanks I got earlier. 

He does not let up. I am close to cumming when he says, “Don’t cum until you feel my cum in you. Learn control.” 

I whimper at the command. My voice was shaky. “Yesss Yes Sir. On fuck” I keep riding him. My tits bouncing. I let my head hang. This is going to be a challenge. I needed to cum. 

I ride him as fast as I can. I am needing to cum. He keeps swatting my ass. Like a cowboy does his horse. I finally understand why it is called the Cowgirl. I am about to fail and cum. It is too hard. 

I think he took pity on me. Both his hands slap down on my ass. Fingers dig into the flesh. He pulls my hips down hard onto his lap. I feel him let go and erupt into me. His seed flooded into me. 

I let out a scream and cum. My pussy ripples up and down his cock. Juices coming from me like a dam had burst. He leans forward and wraps his arms around me. I am pulled back against him. His finger takes a tight grip on my tits. I am withering on his lap. He keeps me on his lap. I collapse on his lap. He does the same underneath me. Skin is slick with sweat. 

As Mr. Santiago gets softer, his cock pops out of me. Warm cum flows from me. We both stay there letting out bodies get back to normal. My mind spinning. 

He taps me on the hip. “Get up and put your hands on the wall.” I do as I am told. I see several flashes and realize he is taking pictures of me. “Come here.” I come to him and she shows me the pictures. It is pictures of my back and ass. Stripes across my back. Handprints on my ass. “I will send them to you, so you have a memory of your first BDSM session.” 

I look at them in disbelief that I enjoyed getting the marks. I wonder how far I will go. He lets me get dressed. I then realize we had been at it for a few hours. No wonder I am so worn out. It hurts a bit to sit in the car and drive home. He told me there will be more of tonight. Especially if I misbehave. I have a few ideas on how to do that. 

Ashleigh Madison