Teaching Dere

I taught school for 26 years, various ages at different times, ending up at the high school level. Then my husband of 35 years suffered a heart attack in August, right before the start of the school year. I hurriedly put in for a year's leave of absence. One part of me thought the distraction would be good for me, but I didn't have the energy to go. The next summer, the school board offered me money to take early retirement and I took it gladly.

One Saturday afternoon in early fall; I was walking out of the grocery store when I spied a thin, dirty young man sitting on a bench. He looked like he was waiting for a cab or something, on closer look, I recognized Derek, a former student from some years back.

"Derek, is that you? I haven't seen you in a long time!"

"Mrs. M, how good to see you."

"I'm surprised you remember me, Derek. How many years has it been, 4 or 5?"

"Well, I just turned 21." We stood there smiling at each other. I started to turn and walk away but paused. "Are you waiting for a ride?"

"No, I just talked to the store manager. I'm trying to get a job but I got involved with the wrong crowd awhile back and had to do some time for petty theft. No one wants to hire a kid just out of jail."

By this time, we were walking toward my car. I opened the trunk and he helped me load the groceries into it. I shut the trunk, and was walking around to the car door when I stopped. "I have roast beef in the crock pot at home, and I'm getting pretty tired of eating alone, would you like to come to my house for supper?"

He looked like he was about to cry, but then the defensive look came over his face. "No, I'm all right." I said, "Derek, I'm not asking anything from you, I'm just going to feed you."

"Well, ok." He tried to make a show of being reluctant to get into my car, but I've been around kids too long to take it seriously. I've always trusted Derek, and he's one kid I wouldn't worry about taking to my home.

We drove in silence for a while. "I hope you got away from the kids who were getting into trouble."

"Yeah, I had a lot of time for thinking the past year. I can see it was their influence that got me into that mess."

"How are your mother and your sister?" He bristled at this question, but when I'd known him, I also knew his mother was a raggedly alcoholic who worked in a bar, and stayed there long hours even when not working. Derek had been the one to take care of his little sister, Susan. They were not abused, but in my opinion, sorely neglected. He raised himself and then helped raise Susan as well. I used to watch him waiting at the corner for her bus, and then walk her home. He took care of her in the evenings, made supper, and tucked her into bed at night. He finally said, "I guess they're all right. I haven't seen Mom in quite awhile, and Susan married her old boyfriend. They moved to Ohio where he had a job waiting for him." I said, "Then she's ok now?"

"Yes, she's doing fine."

We were almost to my house. I said, "Were you ever involved in drugs?"

He said, "Mrs. M, I couldn't. I had to take care of Susan." Yes, I would expect that of him.

Once we got to my house, he helped bring the bags into the house. "Man! You sure but a lot of food! I thought you live alone."

"I do, but I hate shopping, so I buy enough for about a month, so I don't have to go back very often."

"Makes sense to me." While I was putting the groceries away, I said, "You can walk around and check out the house while I'm finishing potatoes and the rest of supper. He looked up quietly and said, "Could I take a bath?" I smiled. "I was hoping you'd do that. Put your dirty clothes on the floor right outside the door and I'll find something you can put on."

I peeled potatoes and put vegetables on to boil, then walked down the hall after I heard the water in the tub quit. I found an old Beatles tee shirt that was a man's large. Large tee shirts are my favorite things to sleep in, if I sleep in anything at all. I picked up the pile of dirty clothes he'd put on the floor, and left the clean tee shirt. I was thinking, I'm sorry I don't keep men's underwear in my house. Well, maybe I won't be Too Sorry. Then was kind of ashamed of myself for thinking those thoughts about a former student. I have never really thought sexually about young men. I've always been interested in older men, such as my husband. But then reminded myself I am no longer teaching in the school district, Derek isn't my student, and he is an adult.

I involved myself with mashing potatoes, making gravy, setting the table. He must've slipped into a chair behind my back. The house was quiet except for the washing machine humming in the background. He said quietly, "Thanks for bringing me into your house." I said, "Derek, I have always felt close to you. You are one of the few kids I really trust."

"Gee, thanks!" He seemed amazed, and that's as much a show of appreciation I expected from him.

After supper he helped me clean up, somehow forgetting he had no under shorts on. The tee just barely touched the top of his cock. And for some reason, (though I was trying not to look, I couldn't really help it) it was hard and trying to poke out from under the tee shirt. I was trying to be cool and acted like I didn't notice. He was trying to be cool as well, acting like he didn't notice me noticing him!

Later, I took a bath, and just put on a robe. I joined him in the living room, where he was watching TV. I picked up a book but couldn't really get into it. We were both sitting on the couch, and he suddenly turned to me and said, "It seems so weird to be sitting here with you like this. You are the nicest person I know." I said, "That's nice to hear. You always seemed to be so lonely. I found myself wishing I could do something to help you or get close to you."

"Well, you're close to me now." and he just reached his arm around me, pulled me close and gave me a fantastic kiss. I don't know what I expected, but it sure wasn't this. Somehow, though, it seemed perfectly natural and I found myself really enjoying it.

Of course I only had a robe on, and it was easily falling loosely from my shoulders, my breasts were hanging freely, and in plain view. He touched my nipple gingerly and it felt wonderful. My body hasn't had any kind of attention from another human being in quite some time. I stood up, reached for the remote and clicked the TV off, and the light, and led him down the hall to my bedroom.

I guess I shouldn't sound so surprised, but as a lover, he was amazingly attentive, and respective. But he was also as much in need of the human sexual closeness as I was. We fucked hard and fast the first time, and then slow and more measured another time. Lying in bed in the magical moment afterward, when he was holding me in his arms and asking what are my preferences in sex, and I said, just this, nothing more. I said what's yours? He said he always wanted an older woman to punish him. I said you aren't in need of punishing from what I know of your life, you're very responsible. He said, "Yeah, I know, but sometimes I just wish someone would care enough about me to..".... He left it at that, but suddenly I felt like a mind reader! "You want a spanking."

"Yes."

I said, I think I know just the thing. I got up and used the bathroom, then went to the top shelf in my closet.

I turned back to the bed still naked and holding a long, sturdy wooden paddle that had indeed come from the old school before we had to quit paddling students. "Roll over on your stomach." I thought he'd chicken out or protest, but he just quietly did that, folded his arms under the pillow. I knelt on the bed next to him, grasped the handle of the paddle firmly and without really think much about it except that he'd asked me for it so sincerely: Whack! It was louder than I though it would be. I waited only a second in case he did protest or change his mind; but he didn't. Whack! Still no protest, so I just started beating his ass hard with the paddle.

I wasn't' really counting, just kind of lost myself in the moment. His ass was turning bright red and soon he was whimpering, but I just kept right on. Actually I have never really thought about doing this to anyone and especially not such a young man, but it felt perfectly right. And as he started crying, I was really getting into it. I was thinking of all the years spent standing in front of a classroom full of students trying to teach them things they had no interest in learning. All the smart mouthed wise assed kids who never learned respect. Suddenly I realized I have no idea how long I've been beating Derek's ass. But thought maybe I should stop. He had never tried to turn over, just laid there taking it.

I put the paddle on the floor half way under the bed, and pulled back the covers, turned off the lamp and lay next to him. I pulled him into my arms, and he put his arms around me as well, just weeping into my shoulder. I said, "Are you all right?"

"Yes, thank you very much." I said, "Scoot down here a little bit." As he did, I fed him my left breast. He took it into his mouth, holding it and suckling like a baby. I fell asleep not knowing when he slept.

The next morning, I gave him his clean clothes, and when in the kitchen drinking coffee and cooking him breakfast, I said, "Would you like to stay for awhile? Or do you have somewhere you need to be?" He said he had nowhere to go, and had just been hanging on the streets. I said, "Well I can put you to work around here to earn your keep and you can stay as long as you want." I thought he was going to weep, but he put his arms around me and kissed me. I said, "Why aren't you sitting down?" with a twinkle in my eye, I knew the reason.

"I'm still a bit sore, but it feels good." I said, "You realize that's the first time I've ever hit a student". He said, "Yeah, but I'm a Big Student, and I needed it. Still do." I smiled because I was hoping that wouldn't' be the one and only time!

It was one of those dark, gloomy, rainy days. We straightened around the house a while, and I suggested we go to town. He said, "I thought you hate to shop." I said, "I do, but you need more clothes. Not that I mind you running around here in my tee shirts and no underwear." He smiled, and got in the car. I bought him a few things, and he wondered aloud how he would ever repay me. I said, I don't need repaying, but was just so glad for the company.

Back at home, I showed him where he could put his things away and I started supper. He said he should be serving me, and I said, "Well, maybe you should." After we ate, I told him it was his turn to do dishes, I went to the living room, and stretched out on the couch. I didn't get a whole lot of sleep after all. I awoke to a lovely feeling, he was kneeling in between my legs on the couch, my cotton dress was pulled up and my panties off of me. He was fingering, and nibbling and licking my pussy. It was the most wonderful feeling. I hadn't felt this good in a really long time. I feigned annoyance, "You should've at least asked me first. Maybe I'll have to punish you again." He muttered, "I hope so."

I was coming on his face, and at the same time saying, "You know, Derek, that isn't really very respectful." He said, "I know," but I was still coming, and he was moving my come all around the whole area. Finally I said, I think that's enough. He said, "For now, we can do this again later." I said, "Fine, but go get the paddle and come right back here. He came in as I was sitting up on the couch on the left side. To my left there is a chair and I told him to pull down his pants, kneel in front of the chair with the top of his body laying on the seat, grasping the back of it. He did as he was told and heaved a big sigh, but didn't say anything. His bottom was still welted from last night, but I was looking forward to beating it again.

Whack! The first few whacks had him jumping a little and groaning. I said, "Does it hurt?" He said, "Yes, Please hit me again." Once again, I just zoned into beating him and I must admit, for not thinking of doing this before, I was thoroughly enjoying myself.

The next morning, I awoke, went to the bathroom and started the coffee while he was still sleeping. I've never done anything like this before, but had an idea. I came back to the bedroom with a rather large rubber band. Derek was lying on his back sleeping peacefully but his cock was standing straight up into the air. I touched it lightly with my fingertips, a feather-light caress that elicited a moan from him though his eye were still closed.

Kneeling next to him, I stretched the rubber band wide, lowered it over his cock and around his balls, and gently let it encase his entire scrotum where it attached to his body. He moaned and I was suddenly aware he was looking at me, but not resisting. Then I picked up the roll of wide packing tape you use to tape packages you send in the mail. I stretched a nice long piece and cut it, wrapped it on the rubber band, around his scrotum noticing his balls had disappeared, pushed up against his cock. Which, by the way was standing up straight and large.

"Mrs. M, I got to pee."

"Later." I was stroking his cock ever so gently and then put my mouth over him, pulling him into my warmth, my tongue running around just under the rim. I sucked him deeper into my throat as he lay there moaning.

"Please, I have to use the bathroom." Ok, I grabbed a hold of his cock and as he got up, I held onto it like a handle and pulled him toward the bathroom. We stood in front of the stool, stroking his stiff, hurting cock. "Ok, so pee."

"I can't."

"Well, you made me quit sucking you so you'd better pee."

"I can't!" He had tears in his eyes. "Very well, then come back to the bedroom."

I was still holding his stiff cock firmly, pulling him. I stood him leaning against the dresser, picked up his thin leather belt, grasped it firmly in my right hand and held the end of his stiff cock with my left fingertips.

I started spanking his cock with the belt. He was crying openly now. "Did you lie to me? You didn't have to pee at all."

"Yes, yes, I did."

"I was happily playing with your cock and you stopped me."

"I'm sorry, ma'am."

"When I'm laying with your cock, you don't' say anything, do you understand?"

"Yes, ma'am." I stopped spanking his cock. Picked up my robe as he stood there whimpering.

"Make the bed, then you may go pee. Do not remove the tape, understand?"

"Yes, ma'am."

"Then come to me in the kitchen."

"Yes, ma'am."

I sat at the kitchen table sipping coffee and gazing out the window. I am not a mean person, but this was going to be fun. "Could I have a cup of coffee, ma'am?" After you've had your morning spanking for lying to me."

"Yes, ma'am."

"Go get the paddle."