Losing Derek

Derek had been living with me for about six months. He was a former student of mine I just sort of picked up outside the grocery store in the fall. We soon got into a routine. It was getting colder and colder that November, rainy and dreary. He cleaned house for me while I played on the computer, read or watched TV. I spanked him regularly; when he needed to be punished and sometimes just because I felt like it.

This sounds like I was resorting to slavery and I suppose yes, I was. At one point, for Christmas no less, I gave him presents, including a dog collar with DEREK printed on it. At first I thought he would resist or complain, but I saw it flicker through his eyes and go. He knelt in front of me complacently while I put it on him, not too tight.

I spread my legs and leaned back. I truly think he enjoyed licking and eating my pussy immensely. I enjoyed spanking him, out of all I did for him and to him, I really enjoyed that the most.

I know his favorite part as well, and that was lying on my lap or next to me sucking on one breast while stroking and pinching the other. My nipples have always been quite sensitive and love any kind of attention and I think he was getting the suckling satisfaction he'd always yearned for and never gotten from his mother.

The other thing I really liked a lot and that was just playing with his cock. If he were lying on my lap suckling on my titties, I was playing with and stroking his cock. Plus I enjoyed thinking of new things to do to it.

For New Year's, for instance, I gave him another present. He eagerly opened it, expecting, well, I don't know what he was expecting. What he got was a leash. "Oh, ma'am. You aren't going to really put this on my collar are you?"

"Are you trying to complain to me, Derek?" He looked at me so pitifully but said nothing to me. "Come stand over here, darling." He came and stood in front of me. I held out my hand for the leash and he handed it to me. It actually looked like a think leather strap, black like his collar.

I took it in my right hand but as I was sitting in front of him, turned my attention to his eager cock.

Just the sight of the leash in the box made his cock stand straight out. He had an appalled look on his face that told me just the sight of this leather strap had on him.

I touched the head of it with my left fingertips and kissed and stroked his hard cock with my tongue. "You're hard." "Yes, ma'am." "You got hard the instant you saw the leash." "Yes, ma'am." This he said so quietly I barely heard him.

I was pulling his stiff cock into my mouth now as he moaned. I wanted to be sure he was aroused, but didn't' want him to release. "Clasp your hands behind your back." "Yes, ma'am." "Now, back up and turn sideways." He did so, so I could stand and face him a little away from his left side.

I held the tip of his cock with my fingertips and using the leash as a spanking implement, began spanking the shaft of his cock. "Oh, oh," he moaned, but didn't try to resist or pull away. "You are going to wear this for the rest of the day, understand?"
"But it's only morning." "I know what time it is, Derek, are you telling me you aren't man enough to wear this all day?"

"No, ma'am." "That's better." His cock was still pretty hard and now was purple and read as well. "Is your cock throbbing?" "Yes, ma'am." "Is it hurting you?" "Yes, ma'am." "You're going to wear this all day for me, aren't you?" "Yes, ma'am, whatever you say."

I slipped the loop of the leash around his cock and positioned it just under the ridge. It was not going to slip off or move at all. I pulled it, the leash as well as his cock, up until I could clip the leash onto his collar. This was a perfect fit! Now his neck movements controlled how much his cock was pulled up or let down.

"Now come over here, bend forward and put your hands on the side of the table." I'd moved a couple chairs out of the way. He stood a little ways from the table, learning forward so his cock was suspended downward, yet still very erect. His hands gripped the edge of the table and I went to get the paddle. I'd half expected him to move before I came back down the hall but he hadn't.

His ass was stuck out at a nice angle and I have to admit here and now that I almost never let it heal completely white anymore. It always had bruises or light welts from his previous spankings.

I stood beside him and said, "You're going to wear that leash for the rest of the day, understand?" "Yes, ma'am." Swat! "You aren't going to touch your cock at all today, understand?" "Yes, ma'am." Swat! "I am going to look at your stiff cock suspended there in front of you, understand?" "Yes, ma'am." Several swats.

I reached down with my left hand and stroked his engorged head that was standing straight out, the leash keeping it pulled up and away from his body. He moaned.

"You like this, don't you Derek?" "No, ma'am. It hurts." "Don't lie to me, Derek. I know you. It hurts but you like it, don't you?" He said nothing and I began swatting him again hard as my fingertips lightly played across the head of his cock. Several more hard swats. His ass was bright red, his face was also read and tears were dripping down on his cheeks. "Yes ma'am. I do like it."

"Say that again, Derek, I couldn't understand you." "He looked at me in the eye and I saw the love and the yearning and the longing there. "I like it very much." I put the paddle on the table and held him to me as he sobbed into my shoulder.

"I love you, Mrs. M." "I love you too, Derek. Now keep your hands at your side and come with me." We walked down the hallway to my den. It has books and a radio and T and the computer. I put him by the wall facing me and said, "Now you can stand there with your hands down at your sides. You are not going to make any sounds and you are not going to touch yourself."

I sat at the computer, he cannot see the screen, and I just surfed the net for a while. Every once in a while I would look up to see how miserable he looked. His cock still stood straight out and when I would just look at it, it seemed to stand a little prouder.

The month of January is always long it seems to me. But this year was even worse. See, I had found Derek's sister Susan and her husband on people search. The first time I contacted her through email, I just reintroduced myself. She remembered me vaguely. I never had her in class, but she'd know me as Derek's teacher.

I mentioned that I had seen Derek in the fall at the grocery store. She was interested in how he was doing. A few emails later I told her I saw him around the holidays and he was looking well.

When I first contacted her, it was with the intention of telling her I found Derek and he's safely living with me. I wasn't going to tell her the rest, of course. In my mind's eye, I still see her as the five year old getting off the kindergarten bus.

But the longer this deception went on, well, it just ate at me. I love Derek, I loved having him around. I didn't want to lose him. Then as the days turned into weeks, I was too ashamed of myself to tell him I'd found her yet kept it from him.

By late February, I just couldn't stand it any longer. I like to think of myself as a basically honest person. But I didn't want to let him go. His company meant a lot to me during the long winter months.

Ok, I set March 1 as the date I would tell him, looking forward to it as a release of my guilt, yet still scared of his reaction.

We awoke that morning, he as usual at my breasts. How could I give this up? I loved the attention he lavished on them. I know he loved them also, but I told myself I can't back down now.

I'd put the leash and collar away some weeks ago and told myself his spanking last night was his last. We got up and I dressed and told him to dress also, we'd go to town today. He made himself breakfast and I had coffee. We sat at the table and suddenly it was now or never. He put his dishes in the sink, poured both of us more coffee and sat down.

"You have something on your mind." "Yes." "Something you don't want to tell me." "Yes." This is the first time he hasn't called me ma'am or Mrs. M. "You're sending me away." "No! I want you to stay forever but I've been keeping something from you."

I could see the questions in his eyes, but thought I saw love there as well. At least I hoped that's what it was. "I found Susan and Gary. I've been emailing them regularly for some time now." He just looked at me solemnly. "I was afraid if I told you, you'd leave and I didn't want to lose you."

He still didn't say anything just looked at me. "Please say something Derek. I feel so terrible, and you know I'm not used to being this dishonest." I looked down. "Especially not with you."

"Do you still have the riding crop you bought last fall?" "Yes." I'd bought one, but never had the heart to use it on him. "Go get it and let's go down to the basement."

I was relieved I'd finally told him. Relieved, he was still speaking to me, but scared because I was reading what was in his mind.

He took the riding crop, and together we walked down the basement steps. "Take off all your clothes." I did so, he didn't grab me or drag me or anything like that. With his hand under my elbow he just gently guided me to the middle of the large basement room.

From the workbench by the wall he took a roll of packing tape, pulled out a length and cut it, placing this over my mouth.

"I don't' mind hearing you scream but I don't want to alarm the neighbors." Then with a length of twine, he tied my wrists together and slipped the twine over a hook in the overhead beam.

Lots of thoughts were going through my head. How dare he, he's a former student. Plus of course my own guilt. Swish! It hit right across my breasts. Ow! I thought he loved my breasts. Swish, Swish, Swish, Swish! Several more across my breasts. Then he stepped to my side and with a back and forth swinging of his arm, whipped my front and side. Over and over, back and forth. Then to my back side. I was screaming for it to stop in my brain; but of course couldn't say anything. This lasted an eternity and then he was on my other side swinging his arm back and forth, back and forth.

Then he was again in front of me. He was whipping my breasts but I could see his face and he was crying This surprised me. I was being whipped. He was crying.

Suddenly he stopped. He was still sobbing. "My dad left us a long time ago. My mother was never there for us. Then even my sister left me. You are the only person in my life I have ever been able to trust. Please don't destroy that. I couldn't take it."

He lifted my hands down so I could put them around him He took the tape off my mouth and we stood there weeping on each other.

"You'd better pull yourself together. You need to take me to town." I just nodded.

Later we were at the train station. I'd given him Susan and Gary's number and address. I said, "I still love you, Derek, if you can ever forgive me, you are always welcome here."

"I might be back, Cathie. I love you too. But if I do, you'll be the slave and the master will be me!" "Yes." He just turned and stepped up onto the train as it was pulling away.