June 24, 2022

I have to lay across my bed to write this. I normally sit at my desk, but I am a bit sore. I was disciplined by Mr. Santiago after work this evening. It was very intense. I think he was looking for a reason to have me up in his playroom, as I am calling it. I am not sure how I feel about what happened. Here is what happened,

I worked tonight to cover for Tonya. She called out with a family emergency. Luke is the one that called me and asked that I come in. I agreed. Friday night is usually a busy night. There are usually good tips on Friday. 

I clocked in and greeted everyone. Mr. Santiago came out of the office, being his usual grumpy self. He was going to be the cook for the night. With a couple of exceptions, we got along as we normally do. It was a normal summer Friday night. We stayed busy all night. About an hour before we closed, I was carrying out a tray full of drinks. I was bumped by Kari. She is one of the other servers. It was a total accident, but the tray of drinks was spilled. Soda, tea, and beer went all over, including me. 

Mr. Santiago was at the prep table and saw everything. He barked out, “Get that cleaned up. Now!”

I jumped to it. I got it all moped up and remade the drinks. I finally got the drinks to the table. Fortunately, they were understanding. 

The rest of the night went off without any more issues. We got everything cleaned and were clocking out when Mr. Santiago told me to stay. I was thinking, “Damn, he is going to punish me.”

I was right. 

He told me to go upstairs to the apartment. “Go up and strip. Kneel on the cushion and wait for me.” He was using his Dominant tone. 

I replied, looking down, “Yes Sir.” I did not argue and did as I was told. I knew how to get into the apartment. I knew everything here was being recorded. I stripped and folded my clothes and knelt on the cushion. Legs spread, hands on thighs, and palms up. I waited. He came in twenty minutes later. I was still on the clock. 

Mr. Santiago walked around me slowly. He seemed to be inspecting me. He used his dominant tone. “I am disappointed in you. You were not doing your best tonight. Spilled a tray of drinks. Customers had to wait. What should I do with you?”

I heard him walk away to the cabinets behind me. I knew better than to look behind me.

I swallowed hard. I had no idea what his mood was. Was he being playful? Was I really going to get punished? Our few times together were mostly playful with some spankings and bondage. 

I jumped at his sharp command.

“On the bed, on your knees, facing the headboard. Now!”

I scrambled to the bed to do as I was told. My heart was racing.

“Lean forward, arms spread out above you.”

I did as I was told. 

He put leather cuffs on both wrists. Chains I had not noticed were attached to the cuffs. They went through the post. He attached similar cuffs to my ankles. Chains were attached to them and went off the edges of the bed. I heard a click and a whine. The chains tightened. My arms were pulled tight. My legs pulled up under me and spread. Another click and the chains stopped. I was trapped. I could not move. 

“I like this look. You restrained and at my mercy. I can do whatever I want to you. How do you feel?”

I could feel his hand on my ass cheeks, sliding over them. I was totally exposed to him. 

I answered him honestly. “Nervous Sir. I don’t know what to expect. “ I could feel my body trembling. 

He seemed to be enjoying this. “That is good. That is exactly what I want.” His fingers teased at my ass and then at my pussy. “This will be more intense than anything we have done before. Do you wish to call your safeword?” 

I am biting my lip. I am thinking about the safeword. Saying “Sunflower” will stop everything going on. I have not used it yet.

“No, Sir. I don’t want to use it yet.”

He swats my ass with his hand. It did sting. I let out a yelp.

“Good. Now let’s get started. Why am I punishing you?”

I felt many strands lying on my back. He had one of his floggers. 

My voice just above a whisper. “Dropping a tray of drinks and not doing my best tonight Sir.”

He dragged the flogger over my skin. He was teasing me. Building up the anticipation. 

“That is correct.” The flogger was lifted off my back for a brief second. It struck my back with some force. I winced. I knew better than to cry out. He kept striking my back in different spots, spreading it out. He then struck my ass. He was not being gentle. This was a first for me. Actually being punished. 

My back and ass were stinging. I knew there would not be any blood. We both agreed on that, the night we talked this out. He is pushing my limits. I was just about to call out my safeword when he stopped. I was thankful. 

I could smell Jasmine. A moment later his hands were spreading oil on my back and ass. The feeling was very soothing. I moaned out with slight pleasure. He let me know what I looked like. "Your back and ass are marked with red stripes. I like the look on your fair skin.” 

I was loving the feeling of the oil being rubbed into my skin. I was relaxing. That did not last long. I then felt fingers that were lubed slip into my ass. I let out a startled gasp. 

“I can tell you are no longer a virgin here. A sizable cock spread you open. I am going to have my fun here as well.” He got my ass all lubed up. I could not move. I did not have a choice. Mr. Santiago was not as big as my brother, who took my anal virginity. He was not tiny either. 

I hissed as he pushed into me. On reflex, I pushed back like I was pushing him out,  and he entered me all the way. He is not as big as Braeden, my brother, but it is still intense. I let out a loud moan. He did not pause and started to slide in and out of me. I was at his mercy. 

I heard him growl. “I wanted to do this the first night I had you here. Damn you have a tight ass. I wonder who was your first here.” His hands gripped my hips. He was ramming into me. 

I could feel an orgasm starting to build. I had no idea you could orgasm just from anal. Well, I did. I cried out. My whole body tensed. I pulled on my restraints and came hard. My juices flooded from me, to puddle on the bed beneath me.

“Ahhhh. Fuuuck. Mr. Santiago. “ My head was spinning. 

Mr, Santiago kept thrusting into me as I came. He pulled out of me when my ass and pussy both stopped clenching. I was breathing hard. I felt the bed shift and heard a couple of drawers open and close. Neither one of us said anything. Feeling the bed shift, Mr. Santiago was behind me again. 

“You may find this tight. I think you will enjoy it.” He pushed a hard object that was already lubed into my just fucked ass. It was a bit bigger than his cock. I loved the feeling of my ass being filled. I moaned out. 

I felt his hands on my hips. He placed his cock at the entrance to my pussy. I cried out. It felt really tight now. My voice was soft. “Oh oh, that is tight Sir. So tight. Please don’t stop.”

He didn’t. He started to slide in and out of me. I’ve had two cocks in me before and loved it. He has not asked and I have not told him of my recent sexual experiences. 

Mr. Santiago was pounding his cock into my pussy. My body jiggled with each thrust. I could not move with the way he had me restrained. I moaned and whimpered with pleasure. I was getting so close to cumming. He crushed that.

“Do not cum until you feel my cum in you, my pet.” 

I groaned and tried to focus on not cumming. He changed the rules. He pulled back, just barely in my pussy. All of a sudden the object in my ass started to vibrate. It resonated within my pussy as well. He started to slam into me again. I was not able to follow his command. I came. I came hard. I let out a scream and exploded. I was squirting. 

Mr, Santiago started to spank my ass as he pounded into me. My pussy and ass had both clenched down. I heard him grunt. His cock swelled and pulsed. He flooded my pussy with his seed. He had more cum than I thought a man his age could make. He stayed in me until his cock went soft. Cum oozed out as he pulled from me. 

Mr. Santiago placed a hand on my lower back “How are you feeling, pet?” 

I thought about my answer. I took a breath and gave him an honest answer.

“I am sore, Sir. You fucked me hard. You spanked me hard. I am starting to hurt in this position." I could not move to relieve any of the pain. 

“Ah, I will untie you then.” He did just that, starting at my ankles. I stretched my legs out. My knees and hips both popped. He released my wrist. I was able to move my arms. My shoulders were sore from the position. He rubbed oil onto my legs, starting at my ankles. He worked his way up to my neck. His fingers felt amazing kneading my sore muscles. The sting on my back and ass eased with the oil he rubbed in. He let me turn over to my back. 

I arched my back making it pop as well. The stretching felt good. I think he was really pleased with how the scene went. He rubbed oil into the front of me. He took his time with my pussy and tits. They were both thoroughly oiled. 

To my surprise, Mr. Santiago parted my legs. He moved between them. When I looked down, he was hard again. This was a first. He mounted me and shoved his cock into me. My head fell back, a moan escaped my lips. 

“I am not done with you, pet. I have more.” He leaned over me. My legs went around his hips. He started to pound into me like it would be the last time. I was amazed and surprised he was able to go again. 

I cried out his name. “Ahhh. Mr. Santiago…Sir! Oh yes, please. Feels so good.“

I was lifting my hips to meet his thrusting. My tits were jiggling with each thrust. While my pussy was sore, it still felt so good. I was not going to last long. 

His hands found both my tits. He kneaded my tits roughly with his strong fingers. Who knew making pizza could give one a strong grip?

“I don’t know what has gotten into me this evening. I felt the need to fuck you again.” He never slowed down. He kept up his hard face pace. 

My hands gripped his shoulders. I arched beneath him. I could not help it. I came. I did not cum as hard as before when I was restrained. It was still an intense and very satisfying orgasm. He did not stop until he came. He flooded into me again. He was cumming as much as his son, Luke, did when I was with him.

We did not stay in the playroom very much longer after that. He had me clean up the area and the toys we used. I came home late to a quiet house. 

Ashleigh Madison