For Greg Pt 1

For Greg, Part 1.

I considered him the one that got away. His name was Greg and the last I heard of him he had moved back east to go back to school. He was the one that got me hooked on erotic stories including spanking and bondage, but I never told him that I would like to try these things. Together we would read about these erotic stories and then we would happily screw each other into the wee hours of the morning. We had a huge falling out over a misunderstanding and we left not talking. Although I knew that it was really my fault, I never had a chance to apologize. I decided that I wanted to try make things right, even if I was unsure were he was. I had thought long and hard about what I felt was a deserving punishment for my misdeeds.

I found were he was and contacted him by email. Turns out things were going well for him and since he was still single and intrigued, he decided to let me come to him and see what I had in mind. I was online and ordered many different things for me forgiveness session. It was only then would he decide if he had forgiven me or not.

I flew to him, knowing that I would get to play out my fantisies with him as my tormentor and lover. I checked into a room asking to be put away from others so that I can get some sleep, I was very tired and I wanted to be in a part of the hotel were I would not be disturbed by others. Really, I did not want to be interupted during my ‘punishment’ session. They were more than happy to comply being off season and having plenty of room.

I went to my room and emailed Greg. I told him that I was in town and which hotel. I did not count on him being online and starting a chat request with me. I being excited and nervous as I had only had light erotic spankings and here I was asking for a real punishment spanking, leaving him to his choice in how to punish me. He said that he would be here by 4 p.m. and I was to leave notice with the front desk so that all he had to do was stop, show id and come up. I was to be waiting submissively for him. Knowing he was always punctual, I quickly bathed and laid out all the implements he had to choose from including medium and large dildos and anal plugs. I put on one of the shortest nighties he used to love seeing me in. I had left word with the front desk as he instructed, but also asked that after he got the door card key for them to call me and let me know he was on his way up. The front desk called up 3:55, not surprising he is still punctual. I quickly inserted the smallest buttplug with lube in my small anus. Really wanting to please him, I assumed a position I knew would get his attention. I readied myself by kneeling just aways away from the door with my hands and forearms on the floor. That way all he would see is the ass that he gets to punish upright and there for him.

I could hear the click of the card key and the door open. He stood for a moment adoring the presentation in front of him. He took in the room, including the dresser and all the implements that he had laid out for me. He did not speak, so I did not speak. He knelt behind me and put his hand on me cool cheeks, knowing we would be so warm, even hot to the touch later. He had come to see if I would really go through with me spanking. Curiousity and his desire to spank the one who had upset him so long ago all led him to meet me today. He went to the dresser and looked at the things I had brought, he picked up the leather paddle, hairbrush and belt. I peeked through my long blonde hair, to see that he had a large gym bag of his own. I was hoping it contained clothes, knowing I was staying the whole weekend and it only being Friday afternoon, maybe I could convince him to stay. I could only hope. He placed the bag near the bed and sat on the end. He knew I was watching him. One thing I knew, he was always clever and smart.

He finally spoke, the only thing he said was, “Crawl over here and onto my lap,” in his firm deep voice. I wanting to be obedient, started crawling with my head down until I reached his feet, I then raised up and placed myself over his lap. My ass right in the middle with my head hanging over. The nightie being loose and slinky slid upward to the middle of my back offereing my whole backside to him. He wasted no time using his hand to start spanking slowly. I laid quietly knowing that my backside was still a very light pink, but would get a lot redder as time moved on. I kept my eyes on the floor and would steal a peek at the impliments he had chosen to use. I gulped, knowing me backside would feel like it was on fire before he was done.

He did not say a word as he started spanking me earnestly about 50 times with his hand. I was kicking and squirming on his lap and trying to do anything I could to minimize the area he was hitting. I was not crying yet, but knew it would be soon. Then he stopped, I knew he was far from done, but I was hoping, just maybe… Nope, he reached over and his movement caused me to see him grab the hairbrush, I knew I was in for it now. He grabbed me up tight and told me that I had really hurt his feelings and that it was time my backside paid the cost for hurting him. Not so much the fight but for not apologizing sooner. With that said he started pelting my buttocks with the hairbrush. It sent a sudden jolt through my whole body and I started really kicking and crying as the brush repeatedly heated up my backside. He would make sure he paid close attention to both sides, striking hard and fast. He did not forget the upper thighs which caused a lot of twisting and crying from poor me. My backside was beet red and I knew he still had the paddle and belt near him. I did not think I could take anymore. I was a mess, but all he could see was this red ass and legs kicking. He continued for another 15 more sharp spanks with the hairbrush. He stopped for a moment, putting the brush down signalling he was done with phase 2 of my punishment. He ordered me up and told me to remove my nightie, I was to stand in the corner nude with my hands on my head. Any rubbing would mean that the punishment was to be extended. I quickly complied, not wanting to endure more than I had already earned and not knowing how much more I could take.

Standing still in the corner softly crying, knowing full well I deserved every bit of what I had already gotten. I kept thinking that I did not think he would really spank me, not as hard as he did. Had I really hurt him as much as he said? Thinking back when we fought last, neither said anything really mean to the other, just that we were stubborn and both unwilling to admit that we were wrong. But I knew that the fight that was started was my fault. He was only trying to help but I just wanted him to listen. All these things were going through my head when I heard him request that I take 2 steps back and bend over. I could either keep me hands on me head or let them hang down, but I was not allowed to rub.