Back again: Playing the Role!

I have been fortunate enough to be speaking with a very intelligent young lady who is early in her exploration of her submissive side. She has written some very exciting stuff and she referred me to where she posted, which was a very interesting site and I will look into providing a link somewhere on my blogs to give you direct access. During one of our conversations the subject of role-play came up. We thought it would make an interesting and appropriate post. I explained to this girl that beyond the master and slave, I had rarely personally explored much in the realm of role-play because I was always happy to just act out whatever role-play the sub brought to the scene. Submissive girls I been involved with often had their own specific ideas about role-play and I can't say that I had a lot of them. Depending on my mood there were some I enjoyed more than others. Sometimes, when we were just in the mood for a lot of sex, some of these role-plays lent themselves to just going at it for hours. Sometimes, if I was particularly in the mood to punish a slave and she was particularly in the mood to be punished there were some role-plays that lent themselves more to this. So I will discuss some of the role-plays I've been involved in, in these cases, all are scenes that the submissives brought to me though together we worked out the details and of course did not look to script too much of it as we both know what we liked and figured we could do it better spontaneously. Hopefully this will give you some ideas to explore on your own
Now, role-plays are an interesting thing. I've been with teachers who liked to do role-plays relating to being a teacher. But I've been with nurses who found it extremely unappealing to dress like a nurse or involve nursing in any way in their role-plays. They worked hard and thee was nothing sexy about being a nurse to them. Different submissive women I've been with had very different attitudes about what was acceptable even in a role-play. I don't mean when it came to acts, or illegal or immoral things, those should already be covered at the very beginning of the D/s relationship and how to discuss nonnegotiable aspects and limits has already been discussed in these blogs.. I mean things that turn the individual submissive off or that they don't find acceptable to play around with. For example, M and S would never involve the word rape in a role-play. As you'll see in some of M's role-play there was some nonconsensual sex, though this is not something she would ever condone outside of role-play, but she would never call it rape and so you won't find the word mentioned. She did like the phrase “use and abuse me” when she would indicate what kind of night she'd like to lay ahead. So I knew those words were acceptable. S did not like the word abuse either. So you wouldn't find that word around her role-plays. And though it's clear S liked the concept and the acts that in D/s would be called humiliation, she didn't like that word at all and preferred---embarrassment. Then there were subs like K and Kayla, which particularly liked the idea and words of rape, abuse and humiliation for the use in and outside of their role-play. Then there were slaves like C and T, which really didn't seem to have a preference. I have tried to include, in various levels of detail, several different role-plays with several different people and the factors that went in to the kinds of actions and ideas and complexity of those role-plays.
I have decided to make this list in an order that goes increasingly more detailed and complex. You may notice that the more detailed or complex role-play tended to occur with submissive women I've written about more often which are the ones with which I had longer relationships. Also, the younger and less experienced submissives tended to think up more simplistic role-plays. They often started with the scene that excited them, got into the action quickly, and were not looking to make this into a big or drawn out production.
T was the youngest (22) and least experienced of any of the submissives I have been with since I have gained a lot of my experience. When I first met M and S they were of similar age to T but we did not get involved in D/s right away and we were all basically inexperienced at the time. K was older than me when I met her and she was already a little experienced with D/s. Kayla was a similar age to T (23) but unlike T, who had not really thought about these things before I introduced them to her, Kayla was independently thinking about and researching D/s on the web when we met.
T wanted to act out a teacher fantasy. She was to be a teacher that was working at an adult night school in a tough neighborhood for extra money and I was one of her students. It was to be clear she liked me and I was very attracted to her so I offered to stay late to help her clean up and then walk her to her car to be safe. Instead, I grabbed her, ripped open her shirt and played with her very big tits, being rough with them which was a favorite of hers; biting, squeezing, pinching, then I pushed up her skirt and ripped off her panties and forced her legs apart with my own, and then fucked her. I took her hard and fast, which was something she (and M) particularly liked. I leaned over her, face to face, as I drove my cock deep inside her pussy with one firm thrust, and I knew I would meet her sweet wetness to usher me right in. T got wet faster than almost any other woman I knew. As I held her down and drove my cock in and out of her she clearly was getting lost in the sex when suddenly I could see realization spread across her face as she wanted to continue the role-play. Suddenly I was met with mock horror and resistance as she tried to push me off her. When she protested I pulled out of her pussy and pulled her over my knee for a hard hand spanking until she relented. Then I fucked her from behind, her bent over a table, until we both came. As far as the classroom went, the best I could arrange was a large conference room in my offices at the time because neither of us could get the use of a classroom. There aren’t really more details to tell. T’s fantasy was simple and not too involved, either reflecting her simple tastes and desire to get to the sex quickly, or just reflecting her younger age and relative lack of experience.
***
C was not that big into role-play. You will see that she was able to help me in another woman's role-plays, but it was harder for her to offer up her own. Sometimes though when we discussed these things she would offer something that appealed to her. I had been involved in helping C out a lot in various ways and she said her fantasies always took her to a place where we were just friends and weren’t D/s involved. She liked to imagine that I saved her from various travails, such as a physical danger or from financial ruin, and then she would show up at my house unannounced to offer herself for payback. In this particular instance, I awkwardly laughed off her offer, and said she was being silly, but I was obviously acting nervous, and very attracted to her, as well as excited and a little intrigued. Then I offered to go get us some drinks. While I was in the kitchen opening the wine and preparing the glasses, C went through a prearranged pile of my stuff and found some of the books I like: The Story of O and 9 1/2 Weeks, and realized that now that she knew this about me---she was quite willing and able to give me what I really wanted. When I walked back into the room with the drinks I found that C had stripped completely naked and was on her knees. As I walked in she said: “Master please make me your slave.” As you can see, her straight role-play was a lot like I said mine would be! Sticking to the Master/slave theme is wonderful, but since it doesn't fit what I was trying to write about here I will not continue with the details because what I felt was relevant and interesting in this case was the way she role-played to get to this point., Though C’s description ends where the action begins, (how annoying is that?!) because at that point the role play blends into our usual Master/slave--D/s, as I already mentioned she will crop up again to help me fulfill another role-play!
***
K was not much into role play. She was enamored of being a slave and having someone to call Master and/or Mistress. As her Mistress was young and still learning about being a Dominant, she rarely offered role play on her behalf. However, when we were alone K confided a fantasy she had. She said she had not told me about it before because she had made the mistake of bringing it up early in her last relationship with a guy she thought might make a good dominant, to give him an idea of the kinds of things she was thinking, that while pretty intense, she thought was still more mainstream then talking prematurely about a Master/slave thing. Apparently it did not go well as he was not a good dominant just an abusive boyfriend. But as for her role play, she fantasized about going door to door collecting for or selling something and some guy would get her in his apartment, and well…the rest will become obvious shortly.
So, K showed up at my place in a loose fitting sweater with a name tag, a conservative skirt and sensible shoes. She tied her lovely blonde hair back into a ponytail and looked all the conservative young volunteer.
When K rang the doorbell and I opened the door she said: “Hello, I'm collecting to help raise funds for the Professional Strippers Retirement Fund. A lot of people don't realize how big an issue this is but stripping is one of the professions with the least saturation of employer paid or supported benefits.”
“Really” I said, “That is very interesting and disconcerting. Why don't you come in, and we can discuss it while I look for my checkbook.” K entered as I held the door open and then locked it behind her and walked in behind her. “You're very beautiful.” I said. “Have you ever considered stripping?”
“Thank you.” She said hesitantly, “No, no, I could never strip like a professional. if you could just go get your checkbook, I really am running behind schedule and should get going.”
“You probably should've thought of that before you came in.” I approached her ominously and backed her up to the couch. She fell seated on to it, and when she tried to get up I pushed her back down. She looked up at me and said: “What are you going to do?”
“First, I am going to watch you strip. Then I am going to do whatever I want.”
“Please let me go.” She said as she stood up.
“Later.… Maybe.” I said as I pulled a ridiculously fake toy gun out of my pocket!
“What are you going to do with that?” She asked nervously.
“Nothing…as long as you do as you are told. Now strip for me and do it like the whore you know you are!” I demanded.
She stared at me for moments, and then started to undulate her hips as she pulled her glasses off and placed them on the table. K was tall and lean and was made to strip from her small and perky tits to her luscious, round hips. However, she had never stripped for me before this and at first she moved awkwardly. She moved more fluidly as she pulled her sweater over her head, exposing those lovely, firm breasts with no shirt or bra underneath. She wriggled out of her skirt less smoothly and then turned her back to me to slide out of her panties while I stared at that fabulous writhing ass. Now completely naked, she turned towards me and backed up and fell back on the couch, seated with her legs tightly shut, and covering her breasts with her arms. She just looked at me and said, “I did what you want. Please let me go.”
“Of course I had you strip naked for me to now send you on your way, right bitch?” I sneered as I stood up and walked towards her. I said you needed to do everything I said. I am surely not done with you!”
I stepped between her legs and pushed them apart with my legs. She tried to stop me and I grabbed her hands and pushed them away. Then I unzipped my pants and pulled out my fully erect cock and she looked down at it and said “Please no.” I smacked her softly across the face. Pushed her back, and guided my cock for a quick and insistent entry. She gasped as I slid in to her tight, wet pussy. I had barely begun to fuck her when she came the first time! Once she regained her composure she started pushing me off and telling me I was awful and should leave her alone. She started lightly pounding on my shoulders to drive me off. I pulled out of her pussy and slapped her face a little harder this time. I grabbed both her thin wrists in one of my hands and pulled her up off the couch. “I didn't think a hot whore like you would need much convincing, but I’m going to enjoy this!” I sat down on the couch and pulled her over my lap. I spanked her as hard as I could, which for K was just a little warm-up. However, true to her role, she kicked and screamed and begged for me to let her go.
“Let you go!” I laughed, “We’re just getting started. Now, will you cooperate or do you need more convincing?” I loosened my grip and to answer my question she jumped up and started running to the door. I grabbed her from behind and swung her around and threw her onto the carpet. I reached into a drawer nearby where I had already placed some soft rope. I tied her hands in front of her then stood up and pulled her standing by the rope. There are few things more beautiful in this world than a willing, naked and tied submissive! Even though she was playing the part of unwilling! I pushed her forward this time so that she was bent over with her hands resting on the couch. I started to fuck her again and as soon as my cock was slippery I pulled it out and shoved it up her ass. She gasped as I stretched her asshole. “You had it easier before bitch but you wouldn't cooperate.” I said as I fucked her asshole hard and deep. I reached around and started to rub her soaking wet pussy, and as much as I planned on delaying it, she came again right away! I pulled out, and guided her to kneeling on the floor as I checked my cock. I grabbed her face and squeezed her cheeks and pulled her mouth open and then shoved my cock right in. I fucked her mouth as hard and deep as I did her asshole, and told her, “that's right whore, suck my cock, taste your tight ass, and you'd better be nice and careful because this will go a lot easier for you if you make me feel good.” While K wasn't the best at oral sex, this was one of the best blow jobs she ever gave me! Nevertheless, before I came too, I pulled out of her mouth and told her: “your heart isn’t in it bitch. I guess you need some more convincing.” I pulled her up by the rope to standing and then brought her to a hook in the wall and hung her wrist rope on the hook. She was standing with her back to me, stretched naked and vulnerable. I grabbed a heavy and long cat’o nine tails. Traditionally the cat o’nine tails you can buy as opposed to the long supposedly brutal ones you see in old movies, are usually soft and light. As regular readers may now K was not looking for soft or light. However, this was a nice heavy and sharp leather with some braids in it. While still not a fierce whip it was probably the most effective of its type that I owned. I started by whipping K's back moderately. She quite appropriately, but not quite convincingly, cried out and begged for me to stop. I increased the severity and she increased her sincerity! Then I moved down to her ass and swung as hard as I could. Still, with this kind of whip I knew the action wasn't too severe. I stopped the whipping and pulled her head back by her hair and asked: “ready to be my cooperative whore, bitch?”
“I'll do anything you say, please untie me!” She begged.
“I don't believe you.” I said. I put down that whip and picked up a long bullwhip. Since I don't like long whips that I have less control over, I like to double up the bullwhips into a leather loop. I started beating her ass pretty hard with it. Her ass and back had a lot of lovely thin red stripes from the last whip. Now her entire ass was becoming a lovely shade of crimson. She started to beg for mercy, and then finally started to plead most sincerely that she would do anything I said.”
“You going to be my little fuck bitch?”
“Yes, sir.” She answered.
“Then beg me. Beg me to use your pussy like the whore you are, and to fuck you up the ass.”
K looked up at me and slowly and so softly and seductively said: “Please sir, rape your fuck bitch. Use my pussy and make me your whore. Pound my asshole until I beg for mercy. Abuse my mouth and let me taste your cum!”
I pulled her rope off the hook and dragged her into the bedroom. I tied her on her back with her arms above her head to the headboard. I climbed between her legs, having slipped out of my clothes after tying her down. I got on top of her and started fucking her warm, wet pussy while I placed kisses and soft bites all over her neck and shoulders. Finally I allowed myself to shoot my first load of cum into her pussy. I like tying a woman’s hands above her head with one rope around both wrists because it's very easy to put her in many positions without the rope getting in the way and to roll her over and push her on her knees and fuck her from behind, or fuck her asshole, or kneel next to her and fuck her mouth. As we had discussed when she told me about the role-play, K spent the next several hours tied that way while I alternately fucked her pussy, asshole or mouth, until I came at least once in each. She wanted to be tied and used for hours and she got exactly what she wanted.
***
Kayla's role-play ideas centered on her working on the weekend as the office cleaning lady to earn extra money. She wanted me to surprise her by walking in on her on the weekend and find her looking at my porn favorites on my private computer while she was masturbating. Finding her this way, I was then to punish and use her just like they do in the D/s porn she would have just discovered that I enjoy. We set this up but I let her know I was going to try to innovate a little. I didn't tell her how. I knew Kayla was interested in other women, and a new sub I knew, C, was very obedient and had already been with other women, so I decided this would be a good opportunity to get the two of them together.
At the agreed to time I entered our outer office, and then quickly entered into my office. As I expected, there was Kayla looking at my computer screen, her sweat pants pulled down around her knees and her hand between her legs rubbing her pussy. She looked up at me with a smile on her face, but that immediately faded as she jumped up, removing her hand from her pussy, and pulling up her pants when she saw I was with someone; a young and pretty girl.
“Can you believe this? I come here to show my girlfriend my office, and I have to be embarrassed to find my cleaning lady looking into my personal pornography collection and masturbating at my desk!”
“What a little whore!” C said. Kayla didn't know what to make of this. She surely knew this is what I expected so she wasn't trying to defend herself. She just sort of stood there watching and listening.
“If the bitch was enjoying my porn this much, then I guess she should know how I'm going to handle this inappropriate behavior! Do you bitch?”
Kayla looked at me and smiled and said, “I think so sir.”
“And how is that?” I asked.
“I would think you would punish me. And I would think you would fuck me. But I don't know how your pretty little girl friend would feel about that.”
“You don't? I am certainly going to punish you and you're going to work very hard to please my girlfriend and make her feel so good that she won't mind if I fuck the both of you!”
“Yes Sir.” Kayla said.
“You needn't have bothered to pull up your pants slut. In fact you might as well take all your clothes off. As a matter of fact, since you enjoy going through the private files on my computer you can find an appropriate MP3 on it now, and you can do a little striptease to the music for us!”
Kayla, who had a lot of confidence in her striptease ability and had always liked to do a strip for me, did not hesitate to sit down at the computer and find an appropriate piece of music, despite the fact that she would now be stripping for a female stranger whose pussy she now knew she would be eating shortly!
Kayla put on the music and began to undulate. If she did anything wrong it was that she stripped a little too quickly because she was obviously in a rush to get to what was coming next!
C and I were sitting on my black leather office couch and Kayla stood before us naked. I turned to C and said, “The whore looks at enough of my porn to get her wet, but does not learn enough from it to know she should be on her knees in front of us?” Upon my saying that immediately Kayla knelt before us. “You know that closet behind you, whore? Ever look inside it?” I asked Kayla.
She glanced back as she answered: “I've tried sir, because as you can see I’m very nosey. But I could never find the key.”
“I keep that key with me. It is for when I bring over friends like C here. It is not for daily business. Here is the key,” I said as I held it near her mouth. She grabbed it in between her teeth and held it in her mouth. “Go crawl over there and open it now.” Kayla crawled over and then stood up to open the lock. When she opened the door, she already knew of course what was in there as she'd seen it many times for herself, but she was playing the role well. She gasped upon opening it. There were whips, ropes, clamps, paddles and canes hanging. There were vibrators, dildos and butt plugs on the shelf. I went into the outer office and picked up the bag that I brought with me today but had not brought out for Kayla to see yet. “Crawl over here and get this out of the bag and put it on the shelf in that closet for now.” I commanded Kayla. She crawled over and reached in the bag and found a strap on harness with a very large rubber cock attached. As she crawled back to the closet to put it on the shelf I explained to her, “C here is one of my slaves, but because of your undisciplined behavior, you will be slave to a slave and addressing her as Mistress today. She will be fucking you with that strap on. If you are very obedient that big fat cock will spend a good amount of time in your pussy. If you remain undisciplined it will no doubt spend much more time up your ass and in your mouth.”
“I understand sir.” Kayla responded.
“C, what should we do with this bitch first? Use her or punish her?” I could see C looking into my eyes trying to ascertain what I wanted to see first. She must've decided that she couldn't decide because what she said was:
“I think we should put the tightest pair of nipple clamps you own on those big tits of hers, and then she should lick my asshole and pussy because I'm sure you would enjoy that!”
I gave C a kiss and smiled, “I love the way you think. That must be why I brought you along today!” I got up and went to the closet and picked an adjustable pair of nipple clamps. This particular pair had last been used on Kayla and if I remember correctly they were very tight and left that way. I walked back over and handed them to the kneeling slut. “Put these on your nipples.” I commanded. Kayla snapped them on each of her nipples and I could see by the pained expression on her face that they were indeed already set tightly. I turned to C, “Make each one a turn tighter would you?” C leaned over to adjust the clamps on Kayla's nipples. Kayla obediently pushed her chest out thrusting her tits right at C while putting her hands behind her back to show she would offer no resistance. C turned each clamp adjustment a full circle around. Kayla cried out with each adjustment. Before I could order it, C was already getting undressed. She stood over the kneeling Kayla, her damp pussy inches from Kayla's face. Then she abruptly turned around, leaned forward against the couch, then reached back and spread her ass cheeks. “Clean my asshole bitch!” She demanded. Kayla moved closer and began to kiss her ass, each cheek, and her mistress's hands holding those cheeks apart. Then she moved her face between the cheeks and began to run her tongue up and down the entire crease of C's ass. She began to work earnestly on C's asshole; licking and tonguing it and finally driving her tongue as deep inside as she could and wiggling it around. Clearly Kayla was feeling very obedient today.
I could see the pleased look on C's face when I asked her, “How is the whore at cleaning your ass?”
C responded, “She's okay, I guess.” And gave me a smile.
“If she's disappointing you,” I began, “you can tighten the clamps on her nipples and see if that makes her do a better job.” I saw Kayla pause for the slightest second when she heard that. I was sure she doubted she could handle another full turn of that tightness adjustment. But since she continued licking her mistress’s asshole instead of begging us not to do that I can only assume she knew C was just playing with her. I suspect Kayla could tell she was doing a good job on her mistress’s asshole. C finally just stepped away from Kayla whose tongue was still sticking out and wiggling, and sat down on the couch and spread her legs. “Eat my pussy bitch. Make your mistress cum and maybe she'll go a little easier on your punishment!” Kayla moved forward, grimacing every time the clamps swung around from movement. C looked up at me and I gestured acceptance. “I think we will remove those clamps for a while.” C announced, and then pulled them off Kayla's nipples. Kayla grimaced and cried out as each one released the tortured nipple inside. Kayla then bent forward and after kissing each of her mistress's thighs and working her way up, then planting some light kisses on the lips of her pussy, Kayla began to please her mistress, darting her tongue slowly but surely between C’s wet lips. I pulled off my clothes and kneeled on the couch next to C and pulled her face to my cock. She started to suck on my throbbing phallus and then I moved away and got behind Kayla was on her hands and knees with her face between her mistresses thighs. I shoved my cock into Kayla's pussy and began to fuck her hard. She came almost immediately, which was often the case with Kayla but I know was magnified by her fantasy come true of being with another woman at the same time as acting out the role-play she wanted to as well. I pulled my soaking wet cock out of her pussy and started to work the fat head into her tight asshole. With each thrust I pushed her face more into her mistress’s pussy. I started spanking her ass as I fucked it, “Make your mistress cum now bitch! Show her what an accomplished whore you are!” I saw Kayla reach a hand down to her own pussy and start stroking herself as she sped up her tongue's work on her mistresse’s clit. Her tight ass was squeezing my cock and I knew I would cum any second. I could see on C's face she was getting close too. I held back as best I could and let go as soon as I saw C cumming, and as we both came I could feel Kayla reach her second orgasm. As the three-way orgasm subsided we all sort of collapsed on the each other. I surveyed the two lovely naked bodies below me, and was very happy that we had all afternoon and evening ahead of us!
***
S liked the secretary fantasy. When she wanted to role play she would come to my office later in the evening or on the weekend, when I would arrange that we would be alone.
This particular time it was a Friday evening.
She was dressed in snug fitting black slacks and a button down shirt. She wore open toed high-heeled shoes and it was clear she was wearing black stockings of some sort, but I could not tell through the pants whether they were full and sexy or just long enough to cover her ankle.
“I'm here to start the job Mr. S. But may I ask a question first?”
“Of course.” I said.
“Do you always start training a secretary after hours?”
“Yes I do.” I said, “You see, and by the way---training is a very good choice of word,” I smiled, then continued, “Anyway---it would waste time and productivity to try to do it during normal business hours when work needs to get done.”
“I guess I understand sir.”
“You may have noticed that this is a very high-paying job for this position, and that it very clearly stated that travel, unusual hours, and great personal discipline and sacrifice would all be required to be made occasionally.”
“I did sir. I wasn't complaining, I was just wondering. I really needed the job and as you say this is a very high-paying job for its type. I never expected such an opportunity and I will do anything to keep it sir. I am prepared to go above and beyond and do whatever I need to and do whatever I am told.”
“Yes, you were very clear and specific during your interview. That is why you got the position. Your desire to please, your willingness to do anything… and your beauty.”
S blushed and said, “Thank you sir, you're very kind.”
“But also…firm and demanding…as you will see during your training.” I said, “First, I do not tolerate errors or mediocre efforts. There can be no mistakes and everything must be the best you can possibly manage.”
“I understand sir.”
“Maybe, but what you think you can possibly manage may not be as good as I think you can accomplish. I will train you to do better than you ever thought you could. If you make it through my training you will become a valuable and exceptionally skilled and unique administrative assistant always able to get the highest paying positions of this type, in the unlikely event you seek such an appointment elsewhere. But in order to successfully complete this training, you must agree to follow all directives no matter how un-orthodox, uncomfortable or confusing they may seem. Do you agree?”
“Yes sir. I agree to anything. I really need this job, I really need this pay, I really want to become exactly the worker you want me to be. I'll do anything sir.”
“Excellent. A wonderful attitude. Now, you will need to multitask at times here. Sit at my computer. The web browser is already open. Go to my favorites. Open the folder that says training.” She did so and she found there were several links in there. “Now, open a word document and you will begin to type what I dictate, while reviewing those links and putting them into subfolders that you will now create. One subfolder will be online lessons. One will be--- advanced training. One will be--- special duties of the private executive secretary. And one will simply be labeled---punishments.” She looked over to me when I finished listing those. “Problem?” I asked.
“No Sir.” She answered.
“You will go to each link and copy the frames on the opening page, then pull that information into the proper folder based on your best efort. Whenever I start dictating you will immediately switch to the word document and type. To get a good handle on what you're capable, I have turned off auto correction in word. After your training is completed you will have auto correction in your own version of Word as a backup, but you will find you will almost never make mistakes after your training is completed.”
I dictated a long and rambling document with many complicated words as quickly as I could speak whenever I saw she was going to the various links. The links were filled with various nonsense I found on the Internet by purported Doms, about lessons for submissive secretaries, training your secretary, and punishing your secretary. At least the punishments were more on target. When she was done with the letter I told her to press print and bring it over to me. As I began to read it I began to question her,
“How do you feel you did with organizing the favorites?”
“I hope I did well sir. I was unprepared for the content and it was distracting because I was very interested in reading some of those websites.”
“Excellent. You will be visiting all of them as part of your training.”
“I'm starting to understand why you felt training was such an apt term, and also more about what my training will entail sir, at least I think so.”
“I am sure you are starting to understand.” I said as I finished reviewing the letter. There are 11 typos and grammatical errors. This is not bad for a first effort under those conditions, but I'm sure you know that this is not acceptable. Have you gained any insight into how I'm going to correct this?”
“I believe I gathered a little bit from the punishment subfolder.”
“Yes.” I pulled out a thin wooden paddle from my desk drawer. “You're going to receive one firm stroke with this paddle for every error. Then we will move on to some of your executive secretary duties. Now go and bend over the end of my desk.” She dutifully did so without any hesitation or question. Her ass looked fantastic in those snug black slacks. “Those pants will make it very difficult for me to assess your punishment. Lower them!” She lowered her pants and she was indeed wearing thigh high lace topped black stockings! Then she bent back over the desk still wearing her black lace boy-shorts panties.
“Do you think those panties will be any less in the way?” I asked sternly.
“I'm sorry Sir.” She said as she lowered them also.
“You will get four more strokes for not thinking about that, for a total of 15.”
“Yes Sir. I deserve that.”
I stood next to her and brought the paddle down on her ass firmly but not very hard. I did so another time, right after the first. The third stroke was much harder and she grunted at that one. I gave her several seconds after that one before I brought the paddle down again. “You have 12 more strokes coming. Since this is corrective I believe it would be helpful if after each stroke you count the numer of that stroke aloud and then say, ‘thank you sir, this punishment will make me a better secretary’.”
“Yes sir.” She responded and I brought the paddle down much harder. She gasped, and then said, “One--thank you sir, this punishment will make me a better secretary.”
She repeated that after each additional stroke. Afterward, she stood up and began to pull up her pants. “Don't bother.” I said. You're bright red bare ass will remind you of your mistakes and your efforts to correct them.
“Yes sir. But it will be difficult for me to walk with my pants around my ankles.”
“I agree,” I said, “and it wouldn't even be safe you to walk that way. Take off your pants and panties but leave on your shoes and stockings. You needn't be bashful here; I have already seen you with your pants and panties down and this will make everything more accessible during your training should any further corrective measures be necessary. Also, you might as well remove your shirt and bra, as they may prove a hindrance during your training for your expected executive secretary duties.
“Yes Sir.” S said as she removed the rest of her clothing. Soon she was standing there, beautiful with her large and firm breasts now bared and completely naked except for her black stockings and high heeled shoes.
“Go to the file cabinet and pull out some empty files and make one for each of the subfolders you created in the browser.” I demanded. She walked to the big file cabinet and opened the top drawer and could see there were no empty files.
“Surely you must realize I would put them in the lowest drawer.” I laughed.
“Of course Sir, I should've guessed!” She said as she bent over giving me a beautiful look at her well paddled ass. From the bent over position she said, “I'm afraid I still don't see the folders.”
“Of course not. I put them all the way in the back so you would have to get on your knees.”
“Of course sir.” S said as she got down on her knees and reached into the back of the drawer. She came out with the blank folders. “You can put them on the desk for now.” I said. “Your task was not to do anything with them but to go through the act of finding them!”
“I understand sir.” She smiled.
“Come over to where I am sitting.” I ordered and she walked over and stood naked before me. “Training as an executive secretary here at my company is far more demanding than even being a well-paid administrative assistant. Obedience is a must, no matter the task. Are you sure you're up for the additional demands?” I asked.
“As I stand here naked with a red paddled butt I think I am beginning to understand what those demands are and yes I believe I am fully up for them sir. I only hope that I want disappoint you, but I now know that you are willing to teach me to improve, and I am willing to accept all your methods of training and correction.”
“Excellent. Why don’t you kneel at my feet while we discuss this?” She knelt down and waited. “During working hours,” I began, “this place is teeming with competent staff and the work gets done efficiently. People are paid well here, but you are paid exceptionally well, even for their standards, because the work I need you to do is more demanding than mere office work, and I need someone willing and disciplined, or at least willing to be disciplined!”
“I am willing to do anything sir, and I'm willing to be disciplined to be made better at everything I do.”
“Excellent. How is your cock sucking skill?”
S paused a moment, then answered, “I think it is good sir, but I suspect you have very high and demanding standards, and it is possible I will need some training to meet your expectations satisfactorily.”
“Let us see what we are working with. But first, rub your breasts and then pinch and twist your nipples to make them hard.” She did as I commanded and it was a lovely sight indeed. “I think your nipples could be harder still. Why don’t you lick and suck them?”. Because her breasts were so large, S could just manipulate them enough to reach the nipples with her tongue or even to get her lips around them occasionally when she was feeling particularly limber. Watching all of this was all I could stand. “Now, open my pants and take out my cock.” I ordered. She pulled my large throbbing cock free of my confining underwear and slacks. She looked like she was about to kiss my cock when I said, “Wait, first hold your tits around my cock and fuck my cock between them!” She did so and her breasts were so firm and supple that my cock felt like it was encased in a fine, thick silk. It felt so good but finally I could not take it anymore! “Suck my cock!” I commanded. She moved between my legs lifted my engorged phallus and began to kiss and lick the tip. Soon she was completely engulfing my large cock with her mouth and taking me deep down her throat. In actuality, S was one of the best I have known at oral sex. I decided to pull her mouth off me before I was about to cum.
“Did I do something wrong sir?”
“No, actually you did everything right, I was just not looking to finish just yet. We have seen that you figuratively are a very appealing ass kisser. It is time to see if you can do it the way you will be expected here!” I barked as I stood up and turned away from her, my ass now in the kneeling secretary’s face. She started to lightly kiss the cheeks of my ass, planting kisses all over it before innocently asking, “Sir, may I please kiss your asshole and clean it with my tongue?”
“You may…” I answered. Besides her blow job abilities S just has one of the most skilled and pleasing mouths I have ever known. She loved tonguing her Master’s ass and she did an amazing job of it! Finally, though tough to pull myself away from this, I walked inches away from her talented mouth and turned and ordered her to: “Go bend over the desk again.”
“Am I to be punished again sir?” She asked.
“If you were, do you really think it's your place to ask if I choose not to volunteer it?” I asked.
“I'm sorry Sir, it is just that you told me I did a good job, so I was trying to figure out if I was to be punished routinely, perhaps as part of a maintenance program, or if you were just being charitable moments ago when you complimented me and told me I did a good job.“
I see. Actually, maintenance punishments are definitely a part of your position, but you should know that I do not need to lie to you; if I say you did a fine job--- you did, and if you are to be punished for a less than satisfactory performance you can be sure you will know about it! Right now you're not actually going to get punished again. You're going to do a couple of tasks and then you're going to get fucked.”
“I see sir.” She said as she walked back to the desk and bent over.
I moved my chair right behind her. “Reach back between your legs and rub your pussy; masturbate for me!” I demanded. She rubbed her pussy as ordered, alternating between lightly circling her clit, and fucking her pussy with a couple of fingers. Her fingers glistened with her juices as I ordered her to: “now use those wet fingers to play with your asshole and then work them into your asshole, and fuck yourself for me!” Dutifully she worked her fingers between her cheeks and began to rub her asshole before finally sticking her fingers into her ass. She began to work them in and out rhythmically fucking her asshole as I had commanded. “Now, pull out your fingers and lick and suck them.” Obediently she did as she was told. I walked up behind her and dropped my pants. I slowly worked my cock head between her swollen wet pussy lips. I fucked her fast and hard and couldn't hold back from shooting my load inside her. I sat back down in my chair and I motioned with my fingers for her to come over. She walked over and then knelt between my legs, and began to lick and suck her juices from my cock as well as sucking out every last drop of my cum.
“Will I be continuing my position here at the company sir?” She asked innocently.
“I am quite sure that soon you will advance from trainee to being my full-time executive assistant!” I smiled.
***
M, perhaps more than anybody else I have known, really liked long drawn out sexual encounters. A lot of people, men and women, talk about going all night long or spending the weekend in bed, but M was one of the few I have ever known who not only backed that desire up, but at times was very insistent on it. I remember driving back from a long weekend and passing cheap truckstops, and her insisting we stop at one because she thought it would be cool to fuck all afternoon in a cheap motel. Now, M also really liked sex outside--whenever it was practical. Once in the warm weather when work was keeping us both particularly busy and apart, M was feeling sexually frustrated and D/s neglected. She wanted to be used and punished long and hard. She told me what she had been fantasizing about, which was to be playing a Peace Corps kind of volunteer in a remote jungle where she was captured and thought to be a spy. She wanted to be interrogated hard while being used equally hard for the enjoyment of her captors. Up until this point we had only had sex outside in either remote locations, or hidden locations under cover of darkness. Punishment outside had really only been spankings or switchings over my knee or over a large rock in fairly secluded park areas during quiet off hours. For the kind of long and intense scene she was looking for now I would have to figure out a good location because obviously we needed a measure of guaranteed seclusion without interruption. Fortunately it was early in the season and there were still cool nights because when you're having sex outside or you’re tied up naked outside for hours, you really don't want to get a lot of mosquito bites! (I still would bring a large can of yard guard!) I finally found a very suitable location. It was several hours upstate New York. A friend of mine owned some land up there and had built a small cabin. Without it, it would've been a good location but there would not have been a bathroom for miles. Now fortunately we had a nice bathroom with a large Jacuzzi tub and separate shower. He owned hundreds of acres up there and there were no trespassing signs on the outskirts of the property. While he wasn't there often he said his neighbors who are there have never reported any unusual or intruder activity. I had never really discussed my specific sexual inclinations with my friend but I let him know I was with someone who appreciated outdoor physical activities. He suggested that we set up in the house first and make sure everything was in working order and that nothing seemed disturbed and if that were the case then he was sure there would be no unexpected intrusions. So we planned out our weekend and we made our way to the...forbidding jungle.
Everything seemed fine when we arrived so we unpacked and took showers and decided how we would begin and proceed. Once the details had been worked out M went outside to walk around in the woods. I grabbed some soft cotton clothesline rope and watched M from a hidden location several yards away. She was wearing an old tank top, shorts and sneakers. I snuck up behind her and grabbed her from behind. The way her body shuddered I could tell I really did surprise her. I brought my left arm around her neck in a headlock but applied no force; as I also pulled her right arm behind her back with my other arm, holding onto her very firmly but applying no pressure whatsoever that could either hurt her arm or her throat. However, I kept my grip firm as she started to fight against me, and I said to her, “If you fight me you spying American bitch, it will be even worse for you!” She stopped struggling and I released her neck to pull her other hand behind her back. I tied her wrists together. “What are you going to do to me?” She asked.
“We know that your country sends spies in the guise of missionaries and aid workers. You want to crush our independence. What I'm going to do to you will depend on what you do for me. If you cooperate you and I will just have a lot of fun here by ourselves. It gets lonely in the jungle. But if you don't cooperate, I am instructed to do anything I need to, to get the information we require. It will be very hard on you and in the end you will tell me what I want to know anyway.”
“I don't know anything that could be of help to you. I'm only a volunteer looking to help. Please don't hurt me.” M was doing a wonderful acting job and I was duly impressed!
“You, speak like any other spy would speak!” I yelled!
“Or an innocent with nothing to hide!” She cried back.
“You're wasting my time and your breath, if you think any of this will help you.” I started pushing her forward until we got to this big overturned log we found earlier. I pushed her forward over the log, using my arms to support her so she lowered gently. “What are you doing?” She asked. For an answer I just yanked down her shorts as hard as I could. Her panties came with them. I pulled them off over her sneakers as she screamed, “no, please no!” I had already unbuttoned my pants and for an answer to her pleading I reached around and covered her mouth with my hand as I drove my cock straight into her pussy. She screamed into my hand and I knew it was for effect because she was so wet that it could not possibly have hurt when my cock slid right in! I removed my hand and started pounding my cock into her pussy, and though she was doing an amazing job of keeping character, she was no longer struggling or begging but just started to moan. I was going to say something threatening but suddenly everything was going so nice I decided to break character until she got back into it. I reached under her and started to rub her clit while I fucked her hard but slow. I sped up as I could feel she was getting ready to cum and we were able to cum together. I pulled my cock out of her abruptly. As I walked around in front of her she had already regained her composure and was back in character: “please, please, I won't tell anyone about this. You did what you wanted now please let me go.”
“Oh no, beautiful spying bitch, whore! We are just getting started. Now lick my cock clean so I don't get my pants all wet!” She started to lick it clean, then looked up at me, then gave my cock a bite from the side. She didn't do it very hard, but she did it hard enough to hurt a little bit. She started to get up as if she was going to try to escape, but I grabbed her hair and pulled. She cried out as she looked at me, and I said, “I guess it doesn't matter that you hurt me, because I'm going to hurt you, and that hasn't changed. If you give me the names and locations of all the other spies posing as volunteers, you can still avoid much suffering…” I paused then said, “Speak, and then you can just be my fucktoy without the torture…until I get tired of you.” I laughed.
“There are no spies…and being fucked by you is torture!”
“I see. Get up!” I commanded. I started pushing her forward once we had cleared the fallen tree. “My pants!” She yelled. I ignored her and left them on the ground. “You won't be needing them anymore, whore!” I sneered. “Fucking me is torture, eh bitch?! When I am through with you, you will beg to be fucked by me rather than continue to be interrogated. You will learn the difference swiftly!”
“No, please, just let me put my pants back on. Please, I’m sorry, please just let me go”
I pushed her forward, “move along bitch!”
She stumbled as I took her on a circuitous route to a large tree with overhanging branches that was right near the cabin. “That is my house, whore, a mansion, no?” I laughed.
“It’s nice.” She muttered.
“Many pretty missionaries like you have been brought here. They all lie like you at first, but eventually they all tell me anything I want to know, and they beg to be fucked by me…until finally they bore me and are of no further use to me and I am done with them. Then I turn them over to our guard where they are imprisoned to hard labor for many years!” I said ominously.
“Please let me go. I’ll do anything you want and then please let me go. I don’t know anything. I’m not a spy.”
“You lying bitch. See how you will sing a different tune after I…persuade you….” I stopped pushing her in front of the tree. I untied one wrist from behind her back and brought both wrists forward holding them tightly together so she would not even think of trying to pull them away. I retied them in front of her then raised them up and threw an end over a low hanging branch then took the end that went over and tied it to the loops around her wrists. Soon she was tied with her hands above her head, stretched tightly, her body firm and taught.
“Please no, don’t, what are you going to do to me, please?” She begged. In answer I started to roughly tear the tank top from her body. There was no bra underneath and now she was tied tightly and completely naked. I walked towards the cabin. I returned with a large duffel bag. I laid it down in front of her and rummaged through it. I pulled out two sticks, one with a string-like strand hanging from it and I saw the quizzical look on her face because she had never seen this before. And I pulled out a pair of clover clamps hanging together by a chain, along with a handful of clothespins. The two sticks screwed together and then I could see the comprehension on M’s face. This was a new whip! Then the fear returned to her expression and voice, “What are those? What are you going to do to me?”
“These, spy whore, are tools of my trade.” I held up the clamps by the chain, leaving the clamps hanging, “These are clamps that bite into any part of the body on which they are placed. They are terrible when placed on all the sensitive parts of a woman’s body---as you will soon see!” M just stared with a genuine look of fear on her face. “And these clothes pins--- well, I won't be doing any laundry, but I think you will be surprised at what else I can do with these. And this,” I said holding up the whip, “is a lunge whip. It is a type of horse whip. It hurts terribly yet is very light. I could beat you all day with this and still have the energy left to fuck you all night!” I laughed. “But of course, if you don’t tell me what I want to know, I have much worse instruments to use on you. I will break you and soon you will tell me the names and locations of every spy while bending over and begging me to use my spy bitch for whatever I want.” I approached her with the clamps and clothes pins.
“No, please don’t. Have mercy.” She trembled softly. I placed the clamps on her nipples and the clothes pins all over her small, firm breasts, then reached down and lightly brushed her pussy lips. She was so wet her thighs were damp! I picked up the whip then walked behind her swishing the whip through the air a few times for effect.
“The names of the spies!” I yelled and punctuated it with a crack of the whip! She shook a little, startled, then said; “We are not spies. We are aide volunteers.” With that I swung the whip and brought it down softly on her back. Her body stiffened and then I repeated the lash harder across her back. Then twice more even harder. She gasped at the last two strokes. Then I lowered my aim and saved all my hardest strokes for her beautiful, firm, round ass. Five hard strokes one right after the other I gave to her ass. Soon the backside of her body wore a beautiful set of crimson stripes!
I walked right up behind her and pulled her hair, jerking her head back, “The names bitch!”
“I don't know any spies.” M repeated.
“Very well.” I said as I released her hair and stopped a few feet behind her and raised the whip again. Three quick lashes of moderate severity across her back had her grunting at the last one. Then another five hard lashes across her ass. Then I walked over to her and stood in front of her this time. I pulled the chain of the clamps, which tightened the Clover clamps. She cried out.
“Such a pity to be making such a beauty suffer when she could be enjoying my cock!” I said.
“I think you enjoy making me suffer.” She said, and I noticed she couldn't help but smile a little bit.
“And what makes you think so, whore? The big bulge in my pants?” I asked as I rubbed my crotch through my jeans and laughed.
“I will never enjoy your cock. You can abuse me with it but you will never get me to acquiesce. You may whip my back and ass, cane and paddle my ass all day, you may hurt my nipples all afternoon, fuck my pussy, my asshole and my mouth all day and all night, you may even humiliate me, make me crawl and embarrass myself, even make me beg for you to use and abuse me, but I'll never give in!” She said, at this point with her eyes closed, getting lost in the excitement as she tried to give me ideas of all the things she’d like me to do to her the rest of the day!
“It is like you're reading my mind!” I laughed. I went to the duffel and put the lunge whip back in and picked out a short thick leather signal whip. I was never much into long bullwhips because they're hard to wield and when they get moving they can be pretty dangerous. I have seen some videos where well known dominatrix’s have used the bullwhip on the ass and back of their male slaves and they are just flicking it, barely moving it, and they are drawing blood. Firstly, I am not looking to draw blood and do not enjoy drawing blood. Secondly, I like to really feel like I am in control of the punishment and the one dishing it out. I wouldn't like the whip doing all the work! That's why I've never been a big fan of the spanking machine or robo cane videos. While it is true I like to watch a woman punish another woman, even then I prefer it to be at my direction, and still I like the woman to use an instrument that requires hard work on her part to deliver the punishment. Also, as I said, I like the control a short whip gives me to hit just the spots I want. I walked behind her with the signal whip.
“Your tits must be very sore from all the clamps.” I said.
“They hurt terribly.” She moaned.
“Don't worry----- this will take your mind off your tits!” I said as I brought the signal whip down hard across her ass. She gasped in surprise. Then twice more I brought it down hard on her ass, then twice across her back with much less severity. I walked right up behind her and leaned against her, the bulge of my cock through my pants rubbing against her whipped ass as I reached around and tugged on the chain of the nipple clamps. She groaned in pain as I leaned my head on her shoulder next to her ear and said: “Tell me what I want to hear, bitch!” As I said that I released the chain of her clamps and reached down and began to massage her soaking wet pussy.
She moaned as she said, “You can keep this up all day, I'll never talk.” I was not sure if she was keeping up her insistence that she was an innocent volunteer, or if she decided to change character and was suddenly playing the spy who would never give in, but either one would fit and continue to work very well so it really didn't matter!
“You will talk. They always do.” I said then stepped back and brought the signal whip down hard across her ass five times fast and twice across her back. She cried out at each blow but knowing M and her reactions and what she could take I knew these cries were for effect. I walked in front of her and jerked hard on the nipple clamp chain. She cried out with more sincerity that time. “Anything to tell me?”
“No.” She answered stoically not looking into my eyes.
“I feel badly about what your poor tits are going through. I think I will remove the clamps.” She looked at me puzzled because I did not approach her to remove them, but walked to the duffel and put in the signal whip and pulled out a riding crop. I walked close to her and raised the crop. She closed her eyes as I knocked one of the clothespins off her breast with a strike of the riding crop. She gasped as it fell off and already I was hitting another. 2 strikes to get that off and the second one slapped the side of her breast as well. When I had hit off all the clothes pins I said, “This crop will never get off those terrible clamps! What do I have in my bag of tricks?” I put the riding crop down and rooted around in the duffel. I came out with 2--- three pound weights! “Perhaps these will help pull the clamps off.” I said as I walked over to my helpless captive. “Please no sir, don’t put those on, have mercy, I don’t know anything, please don’t hurt me anymore.” She begged as I ignored her and attached the weights. She screamed as each one pulled down on the clamps. Usually she handled the addition of weights much more stoically but she had already been wearing the clamps for quite some time and I thought it best to remove them shortly. “Oh, that didn’t work,” I observed seeing that the clamps did not fall off under the weight, then I looked back in the duffel and pulled out 2--- one pound weights. “Maybe I just didn’t use enough weight!” As I attached the additional weights she started begging me for mercy and when I released the weights she screamed through tight lips. I pulled the clamps off and she screamed loudly. I rubbed her pussy which managed to stay wet during the most intense punishment and was now soaking my hand now that I was rubbing her. “We don’t want to damage your lovely nipples---or what would we play with tomorrow?” I laughed as I stared at the duffel to decide what to do next…but I already knew what I wanted to do next. We both really needed to fuck. I started to walk towards the shed behind the cabin. We had not looked in there but my friend told me what he had in there in case I needed anything or wanted to put anything I brought in there. I came out with a wooden horse. Then I went to the trunk of my car and pulled out a thick comforter. I threw it over the horse. I untied M’s hands from above her head and dragged her by her wrists to the horse and pushed her roughly forward over it. I proceeded to tie her wrists and ankles to the 4 legs of the horse. She offered some resistance but not much. I pulled a short rattan cane and a moderate wooden paddle out of the duffel. I walked over with the cane and gave her five firm strokes across her bottom. She grunted with each stroke. “Anything you would like to tell me whore?”
“I have nothing to tell you.” She replied.
I picked up the paddle and gave her a very hard stroke and she cried out. “I am going to do many things now. If you resist or try to hurt me---you will get another 100 strokes just as hard as that. Your ass will be a mess---but it will buy you no respite. I threw done the paddle and started to work my cock into her pussy. It was wet but not as wet as before, which was often the case right after a particularly hard punishment. It took only seconds for my intruding cock to be met with a flood of new juices though. I fucked her slowly at first, slow and deep, then increased my tempo until I fucker her fast and hard while reaching under her and massaging her clit. She came twice almost immediately, one right after the other, which told me she was indeed getting what she wanted from this role-play. I wanted to cum but I knew she was expecting a more thorough violation of all her holes. I pulled out of her pussy and immediately stuck my cock between her cheeks and started to push my way into her tight asshole. She groaned as I pushed my way in as deeply as I could and moaned as I fucked her asshole hard and deeply. When I felt like I could not hold back any more I pulled out of her lovely ass and checked my cock as I walked around in front of her. “You will lick my cock clean and then to show your obedience you will kiss and lick my ass. Then, when I am satisfied, you will suck my cock some more until you suck out every drop of my cum while I use your mouth for my fuck-hole. Fail to satisfy me, or try to bite me again and the paddle will be your reward. You may show you understand by begging to do the tasks I have set before you.”
She stared at the ground and paused for many moments before softly saying, “Please sir, may I lick your cock clean from my asshole? And when you are satisfied, sir, please let me kiss and lick your asshole . Then would you please fuck my mouth until you shoot your load and I taste every drop of your cum sir?”
“Excellent.” I said as I moved closer to her face. She extended her tongue and gave my cock a lovely tongue bath, taking it inside her mouth to begin sucking only after having licked every inch first as she had been trained. After she sucked for a few moments I pulled out of her mouth and turned around presenting my ass to her. Dutifully she started to kiss the cheeks and soon I felt her tongue lightly rubbing between my cheeks. I reached back and spread my cheeks and she instantly darted her tongue between them and stated tonguing my asshole. Then she pushed her face between my cheeks and began planting kisses on my asshole before really working her tongue deep inside me. My cock was throbbing and I could not take it anymore. I turned around and started fucking her mouth slowly but after a few minutes I could not hold back and I started to roughly fuck her mouth until I shot my load. She obediently sucked out every drop and I did not pull out until I was satisfied that my cock was sucked dry.
I untied her and said, “I think we should take a break and go into town for dinner and a drink because you will really need your strength tonight! I suspect your next bout of interrogation will involve some humiliation as you will be touching yourself a lot and cumming a lot, and I imagine you will be spending the night tied to the bed and fucked as much as I can possibly fuck you, you amazing woman!!”
She smiled and kissed me and said, “That sounds lovely but I think we should cook and I packed a couple of bottles of wine, because I think my nipples are too sore to put in a shirt right now, and my butt does not feel like taking a car ride! No doubt you will make sure I am not in much better shape for the long car ride home tomorrow, but I am sure you won’t mind if I sit naked in the car under a blanket for the ride, and maybe on a nice, soft pillow because if I know you, I am quite sure you are not done with me yet…and that’s good because I don’t feel near done either.”
***