Her boyfriend hated her talking to me, and I honored his request at first. I did not want to come between them. But it was obvious she couldn’t stop. She had dark fantasies and like so many women discovered it was difficult finding men serious enough and not afraid to think or do the things she wanted. I surprised her because I have a dark, sadistic side and vivid imagination. Even better, I had actually done these things. Like most women, she didn’t believe me at first, but after seeing a few pictures she had complete faith in what I had done, and what I would do.

Jay was a beautiful young woman. She is a nursing student, working through school, and living with her boyfriend. She is 21 with blonde hair and the typical fit body of a young woman who doesn’t have to work terribly hard to stay thin. If she could fake the right accent she could pass herself off as having Nordic heritage. She found me on a fetish site and we began to chat. It wasn’t unusual for younger women to contact me, but she was different than most I had talked to. She wasn’t exploring, she knew exactly what she wanted. It didn’t take long for her to determine she wanted me to be the one to push her through her ultimate fantasies, and she was serious. The chat’s turned into on-line tasks and demonstrations of what was to come when we met. The only bad thing about Jay was we were not close geographically. Meetings and actual play would take time and coordination to make happen.

She told me about her boyfriend and their relationship, and that they both considered it an open relationship. He had let her play with others, usually with him around. Outside the bedroom their relationship was fine, and I was clear to both of them I had no desire to split them up or steal her from him. I simply wanted to help her with her fantasies, and would let her experience them when we could. Initially, he was okay with us chatting, but that changed when he saw how enamored she became with me. She wanted our first encounter to happen so badly that he became worried and told her she was not to speak with me. She obeyed for a month or two, but she realized she had become depressed at the thought of him taking away or suppressing her fantasies. So she contacted me again, and it was as if we never stopped. The only difference was she now had a sense of empowerment knowing she was doing what she wanted. His young, immature ways had lost out to my distinguished older and experienced confidence.

Our first encounter went off great. She had wanted a CNC type, abduction and torture scenario. I planned things for a month or two and then surprised her. She was not only caught off guard when it happened, but surprised by how intense and realistic I had made it. But that story is for another day. We continued to talk after that first encounter. We spent many chats reliving what had happened, what she liked about it and why. Then we moved into other things and future encounters. There was no doubt it would be rough, extremely rough by most people’s standards. But what happened was going to be a surprise. After she enjoyed the first encounter so much, the idea of being completely in the dark turned her on. She wanted to know nothing. When I had the dates set for my next trip to her area, the planning and scheming began in earnest.

That morning I waited in the suite for her to arrive. She still did not know I was in town, days earlier I had dictated she would make time for me today. I had been sending her tasks to complete much like I had on other days. It had begun at 8:00 AM after her boyfriend left for work. There were a few dummy tasks to keep her from suspecting, but some were for today’s encounter. I demanded she wear a dress and I had her go to a drug store and purchase among other things, a marker and a scarf.

The hotel was next to a park which she had used before for pictures. The online tasks I give her often included pictures for me. Sometimes I play on her fear of exposure and require them to be in public places. The park was a semi-safe area she often used when she was to secretly expose herself in public. I told her today to be at the park at 9:00 AM. She was to write on her thigh with the marker as she had done in the past, “Master Darwin’s Toy.” She would then go to the part of the park near the hotel, and expose that thigh towards the hotel. She gave me updates as required and my excitement grew when I knew she was in the park. I told her that someone, or a few someones, would be watching from the hotel. She would receive a text of a room number and she would go immediately to that room. She was to approach the door and use the scarf to blindfold herself before she knocked.

She was right on time and I saw her walk to within sight distance of the hotel. I had tested it and knew she could not see into the rooms due to the glare on windows this early in the morning. She stood there until 9:00 AM, then looked around and raised the hem of her dress. Her thigh was perfectly exposed. She was a naughty girl and lowered her panties as well. I smiled and texted the room number. She lowered her dress and raised her panties, then reached for her phone. I decided if she was going to be naughty that I would be too. I added another twist, to remove her panties in the elevator. She walked towards the hotel and I could see she was nervous, but she didn’t stop. We had talked in the past about many things such as strangers, whoring her out, and groups of men. I was certain there were many possibilities rolling through her head right now, wondering what was about to happen.

Knowing it would take just a few minutes for her to knock on my door, I made the last preparations. I ensured the camera was set and that the things I would need were near the bed. I grabbed a piece of rope and moved to the door. I heard her outside blindfolding herself and watched through the peephole. As soon as she tied it, she put her hands to her sides and took a deep breath. It was a pretty site. She was trusting me completely and I was going to take advantage of that. We both wanted it that way. She lifted her hand to knock and I quickly swung the door open and grabbed her wrist pulling her in. As I pulled her past me I simply stuck my foot out tripping her. I let her fall to the floor. I shut the door and pounced on her as she was just trying to get up. My body hit hers and my weight pressed her to the floor. I covered her mouth with one hand and held one of her arms with the other.

“It will do you no good to scream, it will simply bring about more pain. I do not intend to hurt you more than you can stand. But I know what you want, and I know you want it to hurt.”

I grabbed her from the floor and threw her up on the bed face down. She struggled a bit but it did not stop me as I pulled her jacket off. The next step was to tie her wrists together. I moved up her body sitting on her upper back. I placed my knees on her biceps to help hold her arms as I tied her wrists together. She struggled and seemed sincerely scared, but I knew she would use her safe-words if she needed to. She may not have recognized my voice yet, but even if she didn’t she trusted me to ensure any man I put her in front of would honor those same words. I suspected she had recognized my voice. I knew she would be focusing on any sound or touch trying to figure out what was happening. That meant the fear she was displaying was due to the surprise and what was happening. Everything was having its desired effect of scaring her.

Once her wrists were bound together I ripped her flimsy sun dress and yanked it off. Weeks ago I had given her a task to try on three different dresses. My favorite of the three hung in the closet having purchased it yesterday. She lay there now, bound, blindfolded and naked beneath me. I pulled my knife and held it to her throat and moved my face next to her ear. “We have discussed many times your virgin ass. You will leave here today with that changed. You know it will hurt and you know I will not be gentle.”

She winced and moaned at hearing my intentions. Many times we discussed her past failed attempts at anal sex. She always stopped when it hurt too much. Sadly, the men she had let try were always too fearful to push on. She wanted it and I knew it. She knew I had been brutal this way before. She knew at this moment it was going to happen.

I moved my free hand underneath her to her crotch.

I stripped and moved in front of her. I grabbed her hair and pulled her head up. She was not quite sobbing but the tears still fell, and she was whimpering. She knew that her tears and sounds turned me on. They made me happy because it was a clear sign I was giving her the realism she wanted. “This is the one time I will ask you, do you remember your safe words?”

She responded with a quick, “Yes Sir.”

I told her she was not to hesitate to use them if needed and that I would never be upset hearing them. We had set upon red, yellow, green as safe words. Red meant to stop everything immediately, yellow was a request to slow down or discuss, and green meant more or harder.

Jay let out a firm “Green” among her whimpers.

I did not hesitate to put my cock in her mouth when I heard it. Holding her head by her hair she opened her mouth and didn’t fight it. My cock was still growing but hard enough to push all the way into her. I didn’t allow her to give me a blow job. Instead, I used her mouth. I was forcing my cock in and out, to the hilt every push. I stopped on occasion to allow her to gasp for air, but went right back to fucking her face. The pace prevented her from swallowing as regularly as she would if she was in control. She was trying to catch air at every chance. Whenever she tried to swallow it would inevitably make her gag or choke. Her spit building up on my cock felt sloppy and good. Pulling it out and wiping her own spit all over her face from time to time felt just as good. A few more thrusts and it was time to move on.

I moved behind her and straddled her legs. I reached one arm completely under her waist and lifted so I could put two pillows under her waist. I groped her ass and slid my thighs along the back of hers until my body was closer to her ass. My cock was lying perfectly between her cheeks. I was now fully hard. The normal color of my cock head, reddened by the rough face fucking, looked wonderful against the pale skin of her ass. I turned my ankles up and over her calves as I knelt over her thighs. I then tucked my toes down and pulled her legs open slightly. She let me open them but groaned in anticipation of what was to come. I knew she was already bracing herself for the pain. I rocked back and let my cock slowly drag down the crack of her ass, past her tight virgin asshole and falling against her pussy. I reached down and grabbed my cock and moved its tip up and down her slit. I smeared her juices all around. I then made a point to move the head between her lips spreading them as I moved it up and down a few more times. By now her entire pussy was soaked as well as my cock head. I moved it back towards the entrance to her pussy and pushed it in.

It was not a gentle thrust, but the groan she let out was from the force of the thrust, not from pain. She was far too wet for it to have hurt. I suspected it was also a bit of surprised relief that I hadn’t tore into her ass just yet. I wanted her wet because that was the only lube I intended on using, and I told her so. I then placed my hands near her shoulders and leaned down and bit the back of her neck. I fucked her like this with several hard thrusts. I held my bite just like an animal would to hold his bitch in place. Her first reaction to the bite was to push her head back against me. When she realized she couldn’t stop me she leaned her head forward and offered her neck to me completely.

I finally released my bite so I could grab her hair and pull her head back. I moved my face close to hers and moved as if to kiss her, but when our lips met it was not for a kiss. I took her lower lip in between my teeth and bit down. She screamed but it did no good. I continued to pummel her pussy and hold her lip in my bite. But the time was coming closer. I released her lip and put a hand on her head and pushed it down into the bed and hovered over her.

“He’s tried to take your ass before but couldn’t. You know I will not stop until I have taken it. No matter how much you scream and cry your ass will be mine soon. I know you and I know you will not want him to touch your ass ever again after I take your ass as viciously as I intend. That weak little boy does not deserve to get what I am going to open up.“

The time had come and she sensed it. I leaned up and put my hands firmly on her ass. I groped her hard once then slid my thumbs down to her little bud. My fingers pointed outward, so as I squeezed my hands, my thumbs could stretch her open. When I did this she knew there was no turning back. Instead of trying to struggle more she braced herself instead. Her hands gripped the mattress in a death grip and her body began to tense. I pushed into her pussy two more times getting ready to switch holes in one move. And then I did it. Pulled my cock out of her pussy and lined it up quickly. I leaned and let my body fall down onto her. My weight helped my thrust force my cock into her ass.

She screamed out loud and I let her. My push was deliberate and her scream lasted as long as it did. I did not put my head in and pause like most men. My cock was now buried and my groin was against her ass cheeks. I pressed her hips into the pillows. She held her body tense for a few moments. When I felt her body relaxing just the slightest I leaned down and spoke into her ear again, “You are my anal slut now.”

When she heard that she exhaled. She tried to speak and I knew the guttural sounds were her attempts at a “Yes Sir.” I drew back until I felt her tight sphincter gripping my cock head. I rammed it in again making her pant and gasp and trying to catch her breath. I began to set a pace and she screamed out, “Oh Fuck, Yes Sir, I’m your anal slut!” She let her head collapse on the bed which just made her ass rise up onto my cock.

It began like that, pulling out slowly and ramming it back in. I repeated this over and over. I grunted louder and louder to let her hear it more than anything. As young as she was her pussy felt tight on my cock, but her virgin ass felt twice as tight. I could not slide into her ass, I had to be brutal and force my way in. Her wiggling made it feel even better. It was not taking long to bring me close to orgasm and I knew it. I fucked her as hard and as fast as I possibly could. I let my force try and get me deeper if that had been possible. I alternated between pushing her head down into the mattress and then yanking her head up by the hair, making sure the look on her face was captured on camera.

To my disappointment, I could hold back no longer. I gathered as much strength as I could and plunged as deep as I could. My hardest thrust yet brought another scream as I pumped the first jet of cum deep into her ass. When I pulled back this time, I pulled completely out letting the second spurt cover her little ass. I watched it as it was already trying to close up. I didn’t stop my rhythm though and pushed back into her. With my cum as added lubricant, I slid in a little easier so I went back to fucking her. Pumping my cum into her every time I bottomed out. Finally, I came to a stop and held still buried in her ass, half collapsed onto her.

She let her head fall and finally eased the grip on the mattress she held the entire time. At my age, it didn’t take long for my cock to start to lose its hardness, and come out of her. I rolled off her and worked my way towards the pillows. Jay looked at me with the prettiest mix of smiling from happiness and wincing from pain. She crawled up to me her legs almost dragging as if she was paralyzed. She looked me in the eye and said; “Thank you, Sir! My ass will forever be yours.”

We kissed for a minute or two until we both realized how tired we were. As she rolled over and curled up, I looked down at the mess that was her ass. My cum was starting to seep from her, over her already bloodied ass.

I moved right in behind her and wrapped my arms around her. I knew Jay had several hours before she had to be home. So we both let ourselves relax. We were asleep almost instantly.