Teaching Tim-F/m spanking fiction

Teaching Tim

The coffee shop was fairly quiet for a Friday afternoon. Tim sat alone in a booth and looked at his watch yet again. Only one minute had passed. Damn the time was moving slowly.

He had arrived early for his appointment, hoping to really make a good first impression on the person he was meeting. But it looked as though she was going to be right on time, if not a few minutes late. He drummed his nails on the table, wondering again what he had gotten himself into.

The mission Tim was on had started several months ago. He was intensely interested in spanking, especially if he was the one on the receiving end. There was also a need in his life for discipline and order so the spanking he was seeking was not purely recreational. Towards this end he had browsed various sites and chatted with women but found most wanted to be spanked and not spank him. While he didn’t mind giving the occasional spanking, he much preferred being on the other side of the lap. He found it exciting, stimulating, and intensely erotic. At the age of 28 he really hadn’t had many spankings except the ones he received as a kid, but he certainly felt the need to have more. Besides that, he wasn’t at all proud of some of his behavior lately. Tasks around the house were ignored until they simply had to be done, and then were usually done late at night when he finally got around to it. Some of this was carrying over into his work life as well and that was completely unacceptable. He was in a position of responsibility and, he was, after all, a grown man. Then why wasn’t he acting like one?

He had run into Samantha online about three months earlier. They had chatted pleasantly at first after establishing they were both spankos. Tim had sighed to himself as Samantha explained she was a sub, but his spirits rose as she also explained she did spank male friends who requested she do so. As they chatted he explained his dilemma and what he thought could help him solve it. Unfortunately they lived about 180 miles apart. Although Samantha was sympathetic, she often found herself in similar situations, that were an awfully long trip to give someone a spanking. Tim then suggested something he had already experienced, getting a phone spanking. He explained that he would self spank according to her directions.

There was a long moment of silence and then Samantha stated quietly that, yes that could work. But only under certain conditions. Without Tim asking she listed them for him. He would have to agree to be totally open and honest with her about whatever behavior issues they were dealing with. She would not play twenty questions, he would need to confess. All decisions were hers to make once they agreed to the terms. There would be no hedging, no complaints about unfairness or the agreement would come to an end.

Tim didn’t quite know how to respond, he wanted this but he hardly knew this woman. Sensing his confusion, Samantha suggested they talk a bit more about themselves. Tim had already told Samantha a good deal and she reciprocated. He found out that she was much older than he was. In fact she was twice his age. She was a teacher and had a grown son about Tim’s age.

Suddenly things seemed to be much clearer in his mind. He really liked the idea of being spanked by an older woman. First of all chances are that she would know what she was doing, secondly, it would have more of a disciplinary aspect to it. He agreed to her terms. She asked him if he was really sure about this. And to his surprise he really was and wanted it right now.

Samantha laughed and said, “No not tonight, you need time to think this over but we will set 10:30 on Thursday night for your first session. They exchanged phone numbers and Tim agreed to let Samantha call him.

Then her voice changed. There was no mean or harsh tone to it, just a sternness that had not been there before. “Very well young man, you have told me some of the problems you have been having. So here are the behaviors you are accountable for. First of all there is to be no procrastinating unless you are truly ill or there is a family emergency. Your house will be in order and your projects at work will be completed on time. Secondly, you are welcome to go out with friends on the weekends but if you stay out late enough and drink enough that you cannot meet your goals the next day you will get spanked for that. Is that clear?”

Tim heard himself quietly stating, “Yes ma’am.”

Again that stern voice, “Thursday evening you have your hairbrush and have two pillows in the middle of your bed. And once again I expect total truth.”

Again his quiet, “Yes ma’am.”

“Alright then I will speak to you on Thursday night but we can chat online during the next couple of nights if you like, especially if any questions come up.” She wished him a good night, told him to behave himself and then signed off.

It was hard falling asleep that night wondering how Thursday would go. Over the phone spankings were usually ok but left him wanting more and always wishing there was someone there to hold and caress him.

So for the next few days Tim tried to do what he was supposed to but the bad habits were so ingrained. Laundry was piled everywhere and housework just was left undone. He fell behind on several projects at work because of not focusing his attention where it needed to be.

In the evenings when he chatted with Samantha the conversations were usually friendly and she answered any questions about spanking that he asked. He wasn’t sure how she could give him aftercare over the phone but she assured him she most certainly could and would.
Finally Thursday came just when he had doubted it ever would. At 10:30 the phone rang and true to her word it was Samantha. The stern tone was back. Tim gulped as he listened. “Well young man, you have told me a little about how the week went; now I expect to her the rest before we go any further.”

Tim thought for a minute, “Well I am sort of behind on a few things.”

“There is no sort of behind Tim, you either are or you aren’t.”

“Well it’s not that bad”, he said optimistically.

“I will be the judge of that, please tell me exactly what you are talking about.”

“Well, I have fallen behind on a couple of work projects, and I really haven’t had the time to get my laundry done. But I tried to; really, I just didn’t have the time.”

Samantha’s voice continued in a measured stern tone, “That is pretty close to a lie. There is no trying, either you do it or you don’t. When you set priorities you make time for what needs to be accomplished whether at work or at home. What do you suppose will happen if this behavior continues at work?”

With a somewhat dry mouth Tim answered, “Well I guess I could lose my job, but I always catch up in time. And I am really good at what I do.”

In a softer tone Samantha continued, “I have no doubt you are very good at what you do, but that won’t help if this procrastination doesn’t stop. And a man your age should not have dirty laundry all over his house. That is totally unacceptable.”

Tim gulped, “Well it’s not all over the house, I mean it’s just in the bathroom and bedroom….and I guess some in the living room.”

There was a short silence. “Tim you have broken the agreement we set, isn’t that true?”

“Yes but not a lot”, his mind raced for excuses.

“The amount really doesn’t matter, the actions do. Do you understand what you deserve for this behavior?”

“Yes Ma’am,” he responded, “I deserve to be spanked.” And in spite of the attempt to get out of it, when he finally said it out loud he realized he not only needed it but oh how he wanted it.

Samantha’s voice took on an authoritarian air, “Yes and that is what is about to happen, right now. Do you have your hairbrush and the pillows over your bed?”

Tim felt a small tremble in his stomach. “Yes Ma’am”.
“Very well, you need to remove your clothes and lay down over the pillows with your bottom up as high as you can get it.”

Tim did as instructed. He had been spanked over the phone this way before but somehow this felt different and he wasn’t sure why. He waited for his instructions.

“Young man, I am so disappointed that you have broken our agreement in a way that can jeopardize your job. And that you care so little for how you live that laundry is just thrown down and ignored. Now I am expecting you to follow every direction I give and make every spank count. If they are not hard enough I expect you to tell me so they can be repeated. Is all that understood?”

“Yes, Ma’am.”

“Now you will start with 25 smacks of that hairbrush hard on the center of each cheek. All in a row, not side to side and about 2 seconds between each one. I will be listening and I will want to hear good solid smacks.”

Tim put the phone down on his bed and turned slightly to one side so he could reach more easily. He smacked his bottom as hard as he could. God it stung! Twenty five times and that was only half way. He took a deep breath and started on the next side. For some reason this hurt even worse than the first twenty five. Man was he glad this was almost over.

It was as though Samantha read his mind. When he picked up the phone and told her he had followed her directions her comment was, “You know we have just begun, don’t you?” The next comment, “They sounded solid, were they hard enough?”

“Yes they really sting, they were hard enough.” Tim reached back to rub just as he heard Samantha say, “No rubbing, not yet.”

“Now young man I want you to deliver 25 solid spanks right in the center of your bottom, on the same spot each time, hard and fast.”

Tim groaned, this was going to burn like hell. He put the phone down and began the twenty five hairbrush smacks. One of top of another in a really sensitive spot. His bottom began to burn and sting. He could feel the warmth of it radiating from his skin.

He picked up the phone once more. “Ok Ma’am, I did as you told me.”

Samantha’s voice was soft but intense, “How does it feel Tim?”

He looked at the phone in disbelief, “It hurts, and it stings.”

“Good, then we are getting somewhere. Now you will spank yourself 25 times at the crease of each thigh where it meets your bottom. These are easier to reach and should good and hard. All in a row, not from side to side.”

He picked up the hairbrush reluctantly and began to spank as hard as he could where directed. As the brush made contact he gasped a bit at the sting. This was the worst spot yet. But as he continued he felt the excitement that had been growing since Samantha had called him. It stung like crazy and he was pretty sure it was getting really red, but it was also causing the same reaction he always got when he was spanked, totally turned on.

As he finished he picked up the phone, “I did as you said Ma’am.”

Samantha’s voice was softer, “That’s very good my dear, and how does it feel?”

Tim reached back and touched his very well warmed bottom, “It stings, really it does.”

“Excellent, then you have done just what I asked. Do you think you learned your lesson this evening Tim? Are you ready to make a more substantial commitment to keeping to deadlines and getting your work done?”

“Yes, Ma’am, I will, at least I will try.”

There was a soft laugh at the other end of the phone. “No there is no trying, you either do it or you don’t. And if you don’t you know what to expect don’t you. But for now your slate is clean. I want you to feel me next to you hugging you and gently rubbing lotion on your backside. Can you feel that Tim.”

It was hard to believe but he actually could. He picked up the bottle of lotion by his bed and rubbed some on himself to make the sensation more real. God he was excited.

Samantha’s soft voice continued talking to him, about rubbing his back, rubbing his legs, and how he had done such a very good job tonight. He closed his eyes and his hand reached down to touch himself. Her voice was everywhere. His bottom was stinging but the sensation was exquisite. Before he could stop, talk, or do anything else his brain cleared and he exploded. He gasped into the phone. Tim could practically hear Samantha smiling; she certainly knew what had happened. “See my dear, I told you aftercare was essential no matter where or how you are spanked. Now experience tells me that you are probably more than a little tired by now. And you have work tomorrow. Sleep well; remember the rules and we will talk again soon. But also remember Tim, each time you break the rules the spanking will be more severe.”

They said good night, Tim hung up the phone, and moved the pillows back where they belonged. Oh man that was more than he expected. But he also found himself wanting more. If he could get a spanking like that over the phone, it would have to be so much better in person.
Samantha and Tim had several more phone sessions and each time he expressed his desire to be spanked in person. She kept reminding him of the distance between them and the doubts she had that he really would be happy with an in person meeting. “Remember I am twice your age, on the phone is one thing, but seeing me in person is quite another.”

Tim always disagreed, “Why do you always bring up your age? I don’t care; in fact I like the idea of being spanked by a more mature woman.”

Then at long last during one phone conversation Tim got what he wanted. “Well my dear, I am coming up to your neck of the woods to visit family. If we can work it out I will be happy to spank you, whether it is for discipline or for being really good. That part is up to you.”

The first word burst out of his mouth, “When? When will you be here?”

Samantha laughed and told him of her plans. They talked for a long time figuring out where to meet and here he was waiting in this damn coffee shop for what seemed like forever.

Tim had seen a picture of Samantha so he knew when she walked in the door. She was an older, somewhat attractive woman. And he was so glad to see a smile on her face. She walked right up to his table and held out her hand, “Well Tim, we finally meet.” Her voice was friendly and warm.

They shook hands and she sat down across from him, putting the big canvas tote she was carrying on the seat next to her. “So how are you, its good to finally meet you in person. The picture I saw of you was so far away it was hard to know what you looked like but you are a very nice looking man.”

“Tthanks,” he stammered slightly. “It’s so good to meet you too…finally.” Samantha looked at him very carefully wondering how ready he was for all this. Being a sub/switch, she knew how intense a spanking could get both physically and emotionally. Some people, though, they felt the need were nowhere near prepared for it. They craved it, that was for sure, but it was very different over the phone and in person.

Samantha ordered a cup of coffee and started talking to Tim about all the aspects of his life, his thoughts, anything she could to get a better sense than she had gotten over the phone. Finally she got to the point, “Tim before I ask the next question, are you sure you want to go through with this? Once we get to your apartment and the door shuts the decision is out of your hands.”

Suddenly Tim was much calmer than he had been all morning, “Yes I am very sure. I have no doubts about this at all.”

“Very well then”, and Samantha took on a serious demeanor. She spoke very softly and intensely even though no one was seated near them. “So Tim, how has your behavior been since your last discipline spanking? And please no hedging, no I tried, none of that, just total honesty.”

Tim took a swallow of coffee, “Well, it hasn’t been terrible but it hasn’t been great either.” At the look on Samantha’s face he started again. “What I meant to say is I have broken some of the rules. I have been late with three projects at work, and I finally got my place really picked up last night because I knew you were coming. But”, he said hopefully, “I haven’t stayed out late drinking even one night.”

Samantha looked at him thoughtfully, “Well I guess we both know that it is a discipline spanking then.” She looked at Tim’s crestfallen face, “One rule that isn’t broken does not fix two broken ones and you already knew that before you told me.” The look on his face confirmed what she had said. “I think Tim we had better get going.” She slid out of the booth, took her bag and waited for him. Tim put the money for their coffee on the table and stood to walk Samantha to the door. They walked in silence. He had told her that he lived very close to the coffee shop so it would just be a short walk.

As he opened the coffee shop door he offered to take her bag for her, it looked kind of bulky. “Thanks Tim, it is a little heavy,” she handed it to him.

“Wow, you aren’t kidding, what do you have in here, bricks?”

“No not bricks, just implements I might need for a very naughty boy.”

Tim almost lost his voice, “Oh”, was all he could think of to say. He looked over at Samantha walking next to him. She was so short, for some reason she sounded taller over the phone. Actually she didn’t really look like she could spank anyone very effectively. He was sure this was going to be one big disappointment. Besides he often wondered if being older meant she wouldn’t be strong enough to really make a difference in the strength of spanking a younger man.

Samantha looked at him silently and smiled to herself, she knew what was going through that busy brain. He had questioned her many times about her spanking abilities. Well, there was no substitute for experience and he was about to have that. They had reached his building

Time unlocked the door to his apartment and stood aside to let Samantha enter first. She carefully looked over the very clean and nicely furnished apartment. “Oh Tim this is really lovely, a very nice place.”

“Thanks Samantha” and he went to put down the bag.

“No my dear, the bag goes in the bedroom and from this point on, its Ma’am.”

The bag was lugged into the bedroom and Samantha followed Tim. “Can I get you anything”, he offered putting the bag down next to the bed.

“No Tim, nothing at all”, suddenly the stern, quiet voice he knew from the phone was there. “I think its time we take care of business.” She sat on the edge of the bed and crossed her legs. For some reason Tim had not noticed until that point that she was dressed all in black. She wore simple black knit dress, black stockings with seams up the back, and black patent heels. Her auburn hair was layered and lay in waves near her face. She looked extremely serious.

Samantha immediately took charge. “Tim, please take off your slacks right now.”

At this point Tim was both so excited and somewhat worried that he could think of nothing but obeying her. “Yes Ma’am.” And he did as she asked. He folded his slacks and laid them on the bed and stood in front of Samantha.

She opened her bag and began removing the contents to lie on the bed next to her. Tim watched in somewhat horrified fascination as she removed a hairbrush, a wicked looking bath brush, a leather strap, a thin wooden paddle, a riding crop, and a small thin clear plastic cane. She smiled slightly, “You never know what you are going to need. Now my dear let me explain a few things. First of all I expect complete obedience. Arguing will only get you a longer spanking. Secondly you may wiggle, squirm and kick your legs, however if you try to get away from me, I will put you in the corner and paddle you red. And that won’t count towards your real spanking. Since this is not a first offense it will be a more severe spanking than I have been able to give you over the phone. And, Tim, there is no safe word. If something is wrong other than with your backside you just tell me. I will know when you have had enough. Now is there anything you have to say for yourself before we begin?”

Tim clutched his hands together in front of him. Suddenly he felt like a very naughty boy caught by his mother. “Yes, Ma’am... I am really sorry for not obeying and, and well I need to know something else.”

Samantha looked up at him, “Yes Tim?”

His voice became hushed, “When I get spanked I get, well, excited, I can’t help it. Is that going to be upsetting for you?”

Samantha looked at him in perfect understanding, “No I won’t be the least bit upset, it’s perfectly normal.” She uncrossed her legs. “And now young man, over my lap right now.”

The authority in her voice brooked no refusal. He lay down over her lap. Once again he wondered if such a little person could give an effective spanking. He didn’t have to wonder long. “Tim I am going to start spanking you with my hand to warm up your bottom, then I will take down your briefs. From this point on you may beg, plead, whatever you like, all decisions are mine.” At that point and before he could utter Yes Ma’am her hand began its descent. She smacked hard and rapidly from one side to the other. While it stung it wasn’t really anything Tim couldn’t handle and again he had his doubts about her abilities. She spanked with her hand for 2 or 3 minutes, stopped and hooked her finger in the waistband of his briefs and pulled them down. Suddenly things changed. He felt so exposed. His briefs were pulled down to his knees. She briefly rubbed both cheeks. “Yes nice and pink, just perfect.”

Tim felt a slight shudder run through his body at her touch. The spanking then began again on his bare skin. Smack! Her hand landed flat across the middle of his bottom again and again. “Shit” this stung. “Hey, hey that really hurts”.

Samantha spoke calmly as she continued spanking, “Yes you are right spankings hurt. Tim I am spanking you for your continued problems especially with procrastination at work. That is nothing (smack) to (smack) be fooling (smack) around with.” He winced at each crack of her hand.

She stopped momentarily and the next sensation was a cool piece of wood moving in circles on his bottom. “Today I hope this has an effect on your behavior so next time I don’t have to punish you.” With that he felt the wood lift and the next time he felt it, there was nothing cool about it. It came smacking down hard on the center of each cheek over and over. The stinging pain was unbelievably intense.

Over and over it descended on his bare skin, “Owwwww hey isn’t that enough?” God why did he ever question this woman’s ability to spank. His feet kicked without his even realizing it. “Pleasee I won’t break any more rules, I promise.” Anything to stop that paddle.

Samantha stopped and rubbed her hand over his skin. She could feel the heat but knew they were certainly not done. Tim shivered as her hand rubbed over the punished area. Oh good, she was finished. “Tim stand up please.” He reached for his briefs. “No you leave them where they are.”

“But, I am nearly naked.” And he watched in silent shock as Samantha took the pillows from the head of his bed and place them in the middle nearest to her. “Lay down over those with your bottom up high” she smacked him soundly, “Right now.”

“Yyyes Ma’am,” She wasn’t done, what the hell was she going to do now. Since he was on the bed he could see all her tools of the trade and almost got up when he saw her pick up the bath brush. Samantha put her hand in the middle of his back and pushed him gently down.

“Now you don’t want to be paddled in the corner do you?”

“Nnnno, no way, “Tim wanted to be sure he was understood. He gritted his teeth and waited. Samantha ran the bath brush, bristle side down over his bottom. It stung but felt good too. In fact he could feel his excitement rising. How the hell could he be excited when it hurt this much.

“Spread your legs Tim,” Samantha spoke sternly. “Right now and no arguing.”

Tim could feel rebellion within him but no way did he want more of that paddle while standing in the corner. He slowly spread his legs apart. God he felt vulnerable. Everything was visible to her. He laid his head down on his hands.

Samantha noted this, checked his backside once more. “Tim I am going to spank you with the bath brush on your bottom and at the tops of your thighs. I do believe you will agree to do a much better job at work on your projects. I also believe this will give you a day or two for remembering the lesson.” With that she lifted the bath brush and he knew he wasn’t going to feel the bristles this time. The first smack made him yelp even though he tried to hold it back. She spanked ten times in a row on each side of his bottom. The spanks were hard and had about two seconds between them.

He squeezed his eyes shut tight; no spanking had ever hurt like this. He felt her pulling up the right side of his bottom exposing the crease between it and his thigh. He grabbed the bedspread knowing what was coming. CRACK! The bath brush landed on the most sensitive spot of his bottom. “OHHh NOOO please stopppp”, he couldn’t help himself but it had no effect on Samantha whatsoever. Ten times the bath brush landed until she moved to the other side and repeated the performance. By that point each spank almost took Tim’s breath away. Finally she stopped.

Softly she spoke to him, “So young man, have you learned your lesson? You certainly have a well spanked bottom.”

“Oh God yes Ma’am, I have truly I have.” Although now that she had stopped and was rubbing the punished skin of his bottom with her hand, the pain was becoming somewhat exquisite in its intensity. Why the hell did he always get turned on by this or even want it. He knew he was in for a day or two of sitting very carefully but he could not deny she had given him exactly what he needed and wanted.

He felt her sit down on the bed next to him and there was the soft voice her remembered from the phone spankings. “Now then Tim, you have a clean slate”, she rubbed his back, “and all is forgiven.” The rubbing was in circular motions and then he felt coolness on his bottom. She began rubbing in a soothing lotion. It stung for a moment and then felt incredibly good. “There now you are my good boy aren’t you?” He felt his excitement growing by the moment. Samantha paid no attention and continued her care of his bruised backside. She leaned over him and gave him a warm hug, whispering in his ear, “I expect much better behavior from you from this point on young man.”

The whisper was more than he could take with all the rubbing and caressing. His body exploded and he went limp over the pillows. “You alright Tim”, Samantha asked in her soothing voice.
“Yes Ma’am”, he replied exhausted and totally relaxed.

She laughed softly, “Punishment is over my dear, you can call me Samantha now. In fact if I ever get a chance to give you that Good behavior spanking you can call me Samantha throughout.”

Tim turned and looked at her. A Good Behavior spanking? “Hey Samantha what’s the difference. I mean this hurt like hell but was pretty amazing.” He rubbed his backside and winced. “I honestly didn’t think you had it in you. I was wrong, that’s for sure. But what could you possibly do to make it better than this.

Samantha looked at him with a big smile, “Why Tim, to find out you will have to behave yourself won’t you.”

He rolled his eyes and she patted his backside gently, “Believe me my dear it will be worth the effort.”

Tim thought for a moment. Damned if he didn’t believe her.

Summer Submission-F/m spanking fiction

Being outdoors on a lovely, mild summer day is such a pleasure. It not only is enjoyable but always sets my mind in fantasy mode. Today was such a day and I was determined to make it unforgettable.

The element of surprise played a large part in my plans. I began putting together a lovely picnic lunch. I found a bottle of our favorite wine, included cheese, fruit, crackers and raw vegetables with a spicy dip that my love enjoyed. For dessert I packed various types of imported cookies and also included bottled water. It was light but just perfect for a summer day.

A number of other items were hidden beneath the soft picnic blanket on the bottom of the basket. I wrapped wine glasses in cloth napkins and included them as well. After smiling at the results I went into the living room. Alex was sitting on the couch reading the paper and finishing his coffee. I put my arms around his neck from behind him and kissed his ear. “Hey have I got a surprise for you!” He leaned back and looked at me.

“Oh you do do you!” The smile on his face was as breathtaking as always.

“Yes, I have packed a picnic for us. I thought we could go out to the preserve and spend some very high quality time together. His one eyebrow lifted as he looked at the sweet smile on my face. He knew I was up to something and I was reasonably sure he wanted to find out what it was. He was wearing khaki shorts and a t shirt; I had on a light summer dress and my straw hat. No need to change, just go as we were.

Of course there were items in the picnic basket that were definitely not food but sustenance of a different kind. But that was for a bit later on.

As we drove out to the preserve Alex kept looking over at me with a grin on his face, one hand on the wheel and one on my thigh. My mind kept going over my plans. I was sure my face was flushed; the thoughts reeling through my head were so exciting.

When we reached the preserve entrance I asked Alex to drive to the area near the western edge that was heavily wooded. It was a beautiful area and very secluded. We had been here several times before, once making love on a blanket under the stars so he knew exactly where I meant. He parked in the closest parking area and we started on foot for just the right spot. Alex carried the picnic basket noting that it seemed pretty heavy. I smiled sweetly and commented that it must be the wine and wine glasses.

As we walked I looked for a likely spot for what I had in mind. We reached a small stand of trees with a picnic table nearby. Absolutely perfect. Alex put down the basket and I began to unpack it. He reached for the blanket at the bottom but I stayed his hand. “Just let me”, I spoke softly. After kissing me thoroughly he looked into my eyes, “Caryn, just what are you up to?” I smiled at him, pulled the blanket out carefully and handed it to him. He shook his head but took the blanket and spread it out near the trees on a soft patch of ground cover.

In the meantime I set out the wine, glasses, and all the food I had packed. I asked Alex if he would go and pick some wild flowers for the table, it would add just the right touch. He protested that if he got caught doing that he would get ticketed.

I gave him a very wicked grin, “Well then you had better not get caught.” Once again he gave me his lifted eyebrow, but set out to find flowers for me. What a sweet man I had. Now was my chance to finish the preparations for my surprises. I had set the food out on one end of the picnic table. Now on the other end I set out the concealed objects. First I laid out a piece of purple satin and on top of it I laid a thin wooden paddle, a lovely oval hairbrush, a purple leather strap, and a thin plastic rod.

I took the long rope I had brought and found a nearby tree with a very sturdy branch. I tested it by grabbing it with my hands and swinging my full weight on it. I threw one end of the rope over the branch. To that end I attached a double wrist restraint. I made sure I could pull the rope easily up the branch.

I returned to the picnic table and laid out two small vibrators, warming massage oil, and aloe vera lotion. I took out a long wand with an ostrich feather attached to it. Satisfied with the arrangements I went off in the direction Alex had headed. In my hand I had a very comfortable blindfold. My mind was racing with the plans I had made and my insides were quivering with excitement.

There ahead of me Alex was picking flowers from a patch of hyssop. I crept up behind him as quietly as possible. As I put my arms around his waist he jumped and almost fell over. He turned to look at me and I saw a scolding look in his eyes until he saw the blindfold, “What are you up to Caryn”.

“Alex, I am shocked at your behavior. You know picking wildflowers in the preserve is against the law. I can’t believe you would blatantly do such a thing.”

He looked from the blindfold to my face and I could see both the excitement and panic in his eyes. “But you told me…”

I shook my head in complete disbelief, “Excuses, always excuses.” Coming up behind him, I put the blindfold over his eyes and waited for his momentary panic to subside. “Now young man we are going to discuss such inappropriate behavior as breaking the law.”

His breathing had completely changed, it was shallow and fast. “Now wait a minute, this isn’t fair. I did what you told me to.”

My answer was one Moms all over the world have used for centuries, “If someone told you to jump off a bridge, would you do it?”

His shoulders slumped, “Well no, but I won’t pick anymore I promise. And I didn’t get caught.” He smiled in satisfaction.
I whispered into his ear, “Oh but you did get caught didn’t you, and by the one person who knows just what you need.”

I reached around in front of his shorts and unzipped them. He grabbed at them before they fell. “Nooo not here. I can’t even see if anyone is here or coming up the trail.”

“But my dear I can see, now let the shorts drop.” He did as I asked. At this point he knew argument would only make the situation more difficult for him and he was in deep enough as it was. Of course the fact that he loved being in that deep did nothing to lessen his anxiety.

So there stood my naughty boy with his pants around his ankles in just his briefs and a t-shirt. I could see the pink color of his face as he realized what would happen next. I hooked my finger into the waistband of his briefs and pulled them to his knees. God I loved looking at his body. I took a quiet moment to admire my wonderful man and naughty little boy.

“Now what happens to bad boys who break the law?”

He gulped hard, “Well they could say they are sorry and get a big kiss and a hug.”

I put my arms around him and hugged him as I kissed him hard on the mouth, “You can always have that my love. Now what happens to bad boys who break the law?”

“Oh God Caryn don’t spank me here please.” Even without seeing his eyes I could hear the pleading in his voice.

My voice was quiet but stern, “That is my choice, not yours and you need a short reminder right now to never break the law again.” I stood next to him, put my arm around his waist to hold him tight, and reminded him that fighting me would result in consequences he would not enjoy. I could see his muscles clench and gave him a hard smack right in the middle of his bottom to remind him that was not a good idea. He got the picture immediately, relaxed the muscles and waited for what was coming next.

As I began to spank him with sharp smacks of my hand I reminded him that breaking the law is never allowed and blaming someone else for your misdeeds is certainly not acceptable. Now even though I have small hands they do give a good stinging spanking and soon he was moving from foot to foot and I was hearing the occasional ouch, or indrawn breath. I noticed with satisfaction the layers of handprints that were a deep shade of pink. It was probably enough for this part of our adventure.

I stopped spanking and began rubbing gently over the skin I had just punished. Before I could say anything Alex had blurted out, “I won’t break the law ever again Caryn, I promise you.” His breathing began to change again as I rubbed his backside and his pleasure with my efforts was quite noticeable.

I hugged him close to me and kissed him softly. “Well now that is a very good boy. However we still have a few things to deal with.” His hand reached for the blindfold and I gently pushed it away. “Oh no young man, I am in charge and that blindfold will help you remember. Now I am going to lead you back to our picnic spot.”

“But Caryn, my clothes”, he knew when he said it that the protest would be in vain.

I smiled as I stroked his hair, “You don’t need them and I will make sure you get safely back. Besides on such a warm day clothes are such a hindrance.”

His sigh told me there would be no further protests. I took his hand and put my other arm around his waist, “Now then let’s get back to our table. I am sure you are getting hungry aren’t you?”

As he reached back to rub his bottom I had to chuckle at the hopeful look on his face thinking perhaps this was all the spanking that would be going on today. Deep inside he knew better. And if he gave it a few moments of thought he would realize just what he had to answer for.

I carefully led him back to the table. I held his waist tightly with one arm and held his hand with the other. As we walked I watched him grow more excited under my control. I leaned up and whispered in his ear, “Only naughty boys get excited about spankings you know.”

“Caryn I can’t help it, its you. How can I not be excited when I am naked in the woods with you?”


“Doesn’t change the fact that you are my bad boy”, I leaned up and kissed his cheek. We reached our picnic table and I led him past it to the blanket in the grass. Once again I hugged him and told him to kneel down. He immediately knelt down and was surprised to find himself on a soft blanket instead of the grass and ground cover. I could tell by his facial expression that he realized he was completely in my control. He reached for the blindfold once more and I stayed his hand.

“No the blindfold stays for now. We are going to have a little discussion Alex.” His face changed at the word discussion, I had to smile. “Do you remember what happened on Wednesday? I would appreciate you telling me what occurred that I told you we would be discussing later in the week.”

“Oh for Gods sake Caryn, that was no big deal. So I bought something without discussing it first. I mean I do work don’t I, it’s not like I am sitting at home doing nothing and spending your money.”

I cleared my throat, “Well that was a rude and uncalled for answer. Yes, you work and so do I. And we have agreed to discuss major expenditures together haven’t we?”
A long sigh preceded his answer, “Yes we have, and I am sorry I was rude but I just don’t see it as a big deal. So I bought a new Blackberry. I needed one, you knew that.”

“However my dear, you did not even let me know you planned to do that. What if I was aware of some other need for that money and it would have been gone.”

“So we would have taken it out of savings, big deal. C’mon Caryn get over it.”

Now this was pretty bold talk for a nude bare bottomed man kneeling on a blanket with a blindfold. But Alex could have his stubborn moments. It was my job to see they didn’t happen very often and when they did he paid the price. “Oh I am going to get over it for sure my dear. As soon as I help you understand you were wrong and I am assured you won’t do it again.”

I took the blindfold off his face and he stood up. I turned him around so he could see the array on the picnic table. “Now look, aren’t you overreacting just a bit. I mean you knew I needed that blackberry. It wasn’t a big surprise that I got one now was it?”

“Alex we have discussed your spending problems before. You know what you did was wrong and you know the consequences.” I stood quietly waiting for his answer.

After a moment of contemplation he agreed, “Yes I knew I should have discussed it with you, I am truly sorry, and yes I know you are going to spank me.”

“And tell me Alex do you deserve this, do you agree this is what you have coming to you?”

I knew this was the most difficult part for him, admitting that setting his backside on fire was what he had coming. He also knew from what was on the table what other activities he could expect. But he also knew the longer he waited the more trouble he would be in. So his answer was subdued but right on time, “Yes I totally deserve a good spanking, I broke one of our agreements.”

I kissed his cheek gently, “Now take the paddle and go back to the blanket please.”

He looked at me sadly, picked up the paddle and walked back over to the blanket. Since he was well aware of our routines he knelt down on the blanket and leaned forward on his hands. Alex was well aware I wanted his bottom up high in the air. I walked over and ran my hand over his bare bottom. A small shiver ran through his body.

I knelt beside him and spoke softly but sternly, “Now I expect you to hold this position and answer any question I ask respectfully, is that clear?”

A very small, “Yes Caryn.”

I put my right hand on his back and laid the wooden paddle on his bottom, moving it in small circles. He moaned softly and I could see the obvious excitement this was causing. I lifted the paddle and brought it down with a resounding smack on his left cheek. He drew in breath and I saw his hands clutch the blanket. I began to smack the paddle back and forth from side to side. The tension in Alex’s back was increasing and I stopped after 20 spanks. I leaned down to look at his face, it was tense but he was alright. “God Caryn I swear I will never do it again, can’t that be enough? It stings like crazy.”

“No my dear we are not finished but you are taking this very well, I am proud of you. You are being such a good boy.” I moved back into position and laid the paddle on his blazing bottom. It was a light red and I knew I would be increasing the depth of color momentarily. The paddle lifted and landed 20 times on his left cheek, then 20 on his right. He began to moan and occasionally cry out. The next 20 were right across the middle of his bottom. Although his bottom became very active in moving from right to left he did not try to get out of position.

“Caryn please no more, I can’t take any more. Please.” The sound of his voice was extremely sincere. But I wasn’t finished. This was an important lesson that needed to be learned.

I put the paddle aside, “Now Alex I am going to prepare you to eat lunch. Then I am going to finish your spanking after we eat. Now lay down on your stomach.”

He did so and I very gently rubbed some lotion into his sore red skin. I could feel the heat coming off his bottom and he groaned as I rubbed but not entirely in pain. When I asked him to stand up the source of his groaning was evident. I shook my head in mock disbelief, “Now look how naughty you are, getting excited over a spanking.” I gave him a playful swat on his bottom and we walked to the picnic table. After a big hug I invited him to sit down on the bench.

His look was utter disbelief, “You have got to be kidding. You want me to sit on a hard wooden bench. Have a heart Caryn.” Well I did have a heart and I smiled lovingly went to the picnic basket and got a small cushion I had brought along. Alex smiled in relief and proceeded to sit down on the cushion. I could certainly tell by the way he squirmed and moved that although it was better than wood it was not exactly comfortable.

I sat down next to him and we kissed and hugged each other as we ate the light lunch I had brought along. Alex leaned his head on my shoulder, “Caryn I really am sorry for what I did. Honest that was quite a spanking, I won’t do it again.”

Now having been into spanking for awhile I recognize a bare bottom promise when I hear one. “Alex my dear, I think you need a reminder of just who is in charge.” I went to the end of the table, picked up a plug and lubricant and returned to him.

“Noooo Caryn please.”

One stern look was all it took and he stood and bent over the table. I squeezed out the lubricant and ran my fingers down the crack in his bottom. I could see sweat on his face and noticed his legs trembling. I lubricated the plug well and very slowly and gently inserted it completely into his bottom. He groaned and clung to the table his butt muscles clenching. “Alright young man sit down immediately.” He did as told but I could see by his face and body position the burning bottom and the fullness of the plug were both uncomfortable and incredibly erotic.

We both sat close and cuddled as we ate the light summer foods. The wine was light and delicious and I could see Alex relaxing against the tingling discomfort he was feeling. He put his head down on my shoulder, “Caryn I really am sorry for not discussing that purchase with you first. You know I am. Can you forgive me for that?” His voice was hopeful.

I held him close, “You will be forgiven, I promise before the day is over.”

I could see he was about to continue the discussion when we heard voices behind us coming up the trail. Alex’s eyes widened in panic, “God Caryn, I have no clothes on.” I reached up to the table and draped the purple satin over his lap. It was still obvious he was nude but nothing inappropriate was showing.

The hikers we heard soon passed by our picnic table but far enough away that I knew they could see little or nothing. Alex on the other hand was ready to panic and head for the hills. With a small smile I could also see how excited he was by the possibility of being seen. I gently lay my hand on his lap, “You are the naughtiest boy in the world I swear you are.”

I watched the hikers go by and saw one woman glance our way and then look back again at us very quickly. She nudged one of her companions who looked over and then I watched her jaw drop. I waved merrily at the group and Alex looked over in the direction I was waving. He groaned as he saw the two women trying to be inconspicuous but staring nonetheless. The group continued on its way as I finished the last of the wine in my glass. I gently rubbed Alex’s back and squeezed his bottom. He turned towards me and took me in his arms kissing me passionately. As our embrace broke I pushed the hair back from his face and gazed into his blue eyes that were smoldering. “Now young man take this cushion and lay over it on the blanket.”

Panic filled his face, “But what if those people come back, what then.” His voice was filled with concern but also excitement. If I knew anything I knew my boy and man.

I whispered in his ear, “Then they will get quite a show and perhaps learn something new.” He shivered in response despite the warmth of the day. Without another word he moved to the blanket and positioned himself stomach down on the pillow. His poor bottom was bright red and the plug was beginning to slowly move out. I knelt next to him and removed it slowly as I caressed his skin.

He moaned very softly and spread his legs apart. My hand reached between his legs and caressed his cock and balls. Then I reached over and put the blindfold back on. I didn’t want him to see what I was going to do next. He did not protest but laid his head in his arms as his breathing deepened. I went to the picnic table and got the rest of the supplies I wanted. Oh how I loved giving him the pleasure he needed and wanted and how I loved the feelings within me. I knelt next to him on the blanket and took my leather strap in hand. I rubbed his shoulders and kissed his burning bottom. “Now my dear, the last part of your punishment.” He held his breath. I didn’t have to swing the strap hard to have it make an impression. He caught his breath and the next snap against his bottom had him yelling despite his intention not too. After ten more spanks with the strap I stopped and lay down next to him holding him close to my body. I could see the tears on his cheeks and kissed them gently away. “Alex you know we have that rule about not buying items without discussion for a reason. We don’t want to lose track of our finances and risk being in any financial trouble. I know a blackberry is no big deal but it still is a considerable expenditure. I do love you and I am almost done. You have been so brave and so good about all of this, I am very proud of you.” The tears continued to fall very quietly.

I sighed as I got up on my knees and picked up the cane. “Alex, you need to stand up and come with me.” He sighed and, without question stood and waited for whatever was coming next. I guided him over to the tree and asked him to put his hands in front, wrists close together. Even with the blindfold on he knew what was coming, but he said nothing. I quietly and gently attached the wrist restraints. After making sure they were on securely I pulled the other end of the rope until my lover’s hands were over his head but not stretched to discomfort. Then I tied the end of the rope around a lower branch. Once again his excitement at being without control was evident. “My dear, the last part of your punishment is the cane.” His body tensed and he unknowingly pulled back from me. I instructed him to stand still, and separate his legs slightly to hold the position. He sighed and did as I asked. I kissed his cheek and then tapped the cane on the very tops of his thighs where I intended the strokes to go. I gave him five strokes at the very top of his thighs. Half strokes that stung but left no welt. He cried out with each one and told me how sorry he was. By the fifth stroke it was easy to believe him.

I immediately released the restraints and put my arms around him holding him close to me and rubbing his back. I walked him back to the blanket and had him lay down on his stomach.

The next step was so necessary to reestablish our connection. I began to rub a cooling lotion on his bottom. I was very gentle and careful. “All is forgiven sweetheart, the slate is clean.”

As I rubbed I heard my love say, “Thank you Caryn, I certainly deserved that, I know I did. I so appreciate how much you care about me and our life together.”

Stretching out next to him on the blanket I took him in my arms and held him very close. He was squirming uncomfortably and I knew the burning on his backside was not the only reason but I was doing this my way as he well knew. We cuddled close to each other kissing and rubbing each other’s backs. I gently rubbed his punished bottom. The blindfold remained in place as I picked up the fluffy ostrich feather on a wand. I began to gently touch his sore backside with it. “Noooooo”, he groaned. But I knew by now when no meant oh God yes don’t stop. Every time I picked up the feather he never knew where it would land next. Each touch of it made his body jump slightly. I love watching him. Then I finally brushed it between his legs and down his thighs. His bottom arched up and I could see how hard and excited he was.

I quickly picked up the lubricant and rubbed it over the crack of his bottom and into the opening I was about to invade. “Oh God Caryn no not out here.” I gave him a brief smack on the bottom.

“No back talk young man.” I continued with the lubricant and chose which vibrator I wanted to use and lubricated it as well.

I gently began to insert the vibrator slowly and then turned it on. As I did so I also reached down to massage his hard cock and tease his balls with a nail massage. I moved the vibrator in and out slowly and continue my ministrations with my hands. I could feel his body start to stiffen and his bottom moved up towards the vibrator. This is what I had waited for. I could feel the hot, wet excitement between my own legs and knew how badly I wanted him.

As I removed the vibrator slowly, I whispered, “Alex I want you so much, I can’t take much more.” I tore off the blindfold and turned over on my back. I could see the passion in every angle of his gorgeous face.

He pushed my dress up knowing I would have nothing on underneath to impede him. My legs separated and he ran his fingers down through my pussy and rubbed my clit firmly but slowly. Now it was my turn to moan.

As he entered me and thrust deep and hard I wrapped my legs around his waist and pulled his bottom closer with my hands

Our bodies moved together and I squeezed his stinging bum with my hands. I could still feel the heat coming off of them. It was as if I had given him the signal he was waiting for. With one more deep thrust he came hard and my body began to pulse around him inside. If felt as if I would never stop coming, wave after wave.

We collapsed into each other’s arms. I brushed his hair back and asked if he was alright. The little boy grin I loved popped up on his face. “Of course I am who could resist a summer picnic.” We both began laughing. Oh he was such delight, the man of my dreams and the boy of my heart.