{"loaderData":{"4":{"story":{"id":"5c429a50-4f35-4840-912a-d77e59b09c0f","seriesId":null,"seriesName":null,"currentUserId":"00000000-0000-0000-0000-000000000000","added":"2024-02-10T03:07:46.279Z","title":"Her Son's Best Friend","slug":"her-sons-best-friend","shortId":"duld9VMf","authorNote":null,"disclaimer":null,"type":"Novella","paidUrl":null,"synopsis":"A woman enslaves her teenage son's best friend, whom she lusts to turn into her sexslave. It is a story about control before it Moves to more hardcore domination.","partCount":3,"parts":[{"partId":"d2a8d61d-ba5d-411d-9acb-ebd32cd27ffb","title":"Enslaving Gary","summary":"Her Son's Best Friend\n \nolivercromwell2004@yahoo.com\n \nThis starts slowly. It is a s","wordCount":10359,"readTime":52,"number":1,"state":"Published"},{"partId":"2c0441d1-3edb-413f-866e-630793c0a283","title":null,"summary":" \nHer Son's Best Friend, Part II\n \nolivercromwell2004@yahoo.com\n \n Almost Six Ye","wordCount":6742,"readTime":34,"number":2,"state":"Published"},{"partId":"87e6b480-5168-49ac-8208-b38d56a5d829","title":null,"summary":"Chapter 3: Her Son's Best Friend: Christopher joins the Barron household.\n \noliverc","wordCount":9234,"readTime":46,"number":3,"state":"Published"}],"currentPart":1,"contentTitle":"Enslaving Gary","content":"

Her Son's Best Friend

This starts slowly. It is a story about domination and control, before it is a story about sex. But ultimately it is about an older woman who lusts for the young, physically smaller friend of her son who she wants as her sex slave.

Caroline Barron was an impressive, majestic woman. At 6’1” and 1175 lbs with long red hair, she commanded any room she was in. It was a good thing, too, because as a mother forced to raise a son on her own, it helped reinforce her authority. Raising Doug was always going to be a challenge, the more so since he had a lot of his father in him. He, too, was tall and athletic, and girls swooned over him. The same girls did not seem to have much of an eye for Gary, Doug's best friend, and that suited Caroline just fine because she decided she would have Gary for herself.

For as long as Caroline could remember, she enjoyed sexually dominating the men with whom she had relationships. As her boyfriends of the time would attest, she was a natural. Yet, when she graduated college and her sights were set on building a career and getting married and having a family, that ardor cooled somewhat. As a result, she ended up marrying a man with whom she would play rope and bondage games from time to time but also alternating control. When Caroline took time off from her career to raise her son, her desire to sexually dominate her husband rose greatly while Doug was a toddler and, as a result, her marriage collapsed. Caroline didn't mind being home as a housewife and mother, but it had the perverse effect of wanting to dominate more in the bedroom because she had less control outside of it. Conversely, her husband's career, for which Caroline had sacrificed much, was blossoming but his idea of fun wasn't to come home and supplicate on his knees at night when so many beautiful young things were throwing themselves at him at work.

By the time Doug was nine and Caroline 33, she was divorced. She received a nice settlement, courtesy of her husband's stock options, and regular alimony. Rather than restart a career in a town where her husband was thriving, Caroline moved herself and her son to the outskirts of a city several hundred miles away. She didn't need to work full-time, but found a satisfying job with a non-profit that allowed her to use her skills and keep to school hours to care for her child.

From the beginning, Caroline always thought Doug's friendship with Gary peculiar. They were opposites in many ways. Doug was outgoing and athletic, while Gary was neither. Still, they became fast friends and stayed that way to the present day. Years later Doug would explain to his mother that at the new school when they had first moved, Gary was the only one for a long time who would be friends with the \"new kid.\" It was something he never forgot and would never forget. And through the years, the boys helped each other. Doug grew tall and athletic like his mother and father, smart but not brilliant, weak at math. He was popular and well-liked. Gary's growth stopped at 5'8'. In high school, he was not overly nerdy, though much more bookish than Caroline's son. Ordinarily he might have been a regular target for rough treatment at the hands of the school's athletes, but everyone knew about Doug's friendship with Gary and no ever tried anything with him, at least not for very long. Gary, for his part, year in and year out, helped Doug with math. With Gary, Doug was a B student. Without him, C or D. Gary spent many early evenings, after Doug's daily sports practices, tutoring his friend in math.

Although Caroline dated new men in the new city, she did not develop any lasting relationships. Caroline dominated in most of those relationships but none were especially satisfying, many of the men were actually too needy emotionally.

Gary was 15 when the thought first crossed Caroline's mind that she could dominate him, physically and sexually. He was a cute boy, wiry, not buff, always polite with a seemingly eager-to-please personality. She quickly put it out of her mind, however, scolding herself for thinking about actions that were frankly illegal. At 16, Caroline thought Gary was gay, in light of the fact he never mentioned or talked about girls. When she finally raised this possibility with Doug, he assured his mother that Gary indeed liked girls and was not gay.

\"Just because he doesn't go on about the cheerleaders in front of you, that doesn't make him gay, Mom!\" The truth was that he was simply too shy to try very often to go with out girls and the couple of times he tried, it hadn't worked, Doug told his mother.

When Gary was 17 at the start of their senior year in high school, Caroline decided she wanted Gary, that she wanted to dominate him completely and make him her sex slave. If she did this right, she thought, he would be devoted to her by the time he turned 18 in January and, then, he was fair game to make her conquest of him complete.

Caroline was actually a little surprised at herself, at the fact that her mind was turning in the direction of wanting her son’s best friend, a 17-year old boy. But on the other hand, why not? She had no intentions of doing anything truly serious with him until he was of legal age. It was her age and maturity, unlike the girls of Gary’s age, that saw in him numerous things that they were missing. He was not unattractive, he was a nice and polite young man, he was clearly going to be eager to please and malleable. Unlike some 40-year old male, even a submissive one, she would be able to mold the virginal teenager into her ideal lover. And what is more, she knew that once she was able to take him completely, his age meant he was almost certainly energetic enough and having the stamina to keep up with her demands.

The question was: how to do it? It had been some time since she had tried to seduce someone and two lives ago since she had tried to seduce a teenager. The first step, prior to the start of Doug’s and Gary’s senior year was to simply look attractive and sexy when Gary was around, expecting him to notice her and at least get his mind to think from time to time how great it would be to have her. This was not hard to do. The summer permitted shorts, halter tops or tight t-shirts, and pumps which accented her already long, attractive, and shapely legs. This worked. She noticed Gary's lingering stares at her from time to time, although the guys were always doing things, so he didn't spend much time in her presence for long. Still, it was a start.

Once school began, Gary spent more and more time around the Barron residence, helping Doug with his math, routinely three days a week after sports practice was over, not counting time they spent together on the weekends. It was not unusual for Gary to spend eight hours at Caroline's house during the week, as he often showed up before Gary arrived home on the late bus. It was in those moments, when she and Gary were alone, that Caroline slowly began to reel him in.

At first she would just chit-chat with him, about anything really, often doing things that kept his clearly interested face focused on her sexy body. She wanted to make it easy for him to look at her. Over the course of a couple of weeks, she had numerous encounters with Gary like this, always dressed sexily and revealingly---but not too much. Caroline began to work into her interactions with Gary many small touches and brushes with her hands, legs, and breasts. And the more she did of this, the earlier Gary was showing up at her house. At first, he had been only 15 minutes before Gary came home, but at the end of three weeks of this treatment, Gary was showing up almost an hour early, even volunteering to help Caroline with anything she needed help with.

One day she decided to steer the conversation towards sex. \"So, Gary, why is it you don't have a girlfriend, instead of hanging around an old lady like me? Lord knows Doug seems to have a steady stream of them!\"

Gary turned red a bit at this unexpected turn in the conversation. \"Well, uh, I, uh, don't know. I'm not very good at talking with them beyond school stuff. I'm a little shy, I guess, and girls don't seem to like shy.\"

“Really,\" Caroline replied. \"I've always found it rather cute myself.\" Gary turned redder at this statement but she doubted he knew it. \"You have many desirable qualities, Gary. You're smart, you're loyal, you're kind, you're a handsome young man!. It would seem to me that that is a winning combination.\"

Gary's embarrassment grew at the sound of these words, yet inside he loved hearing the flattery. However, he was a little embarrassed to find himself growing a rather strong erection and made some effort to hide it from Mrs. Barron. He was not completely successful. By now he had had a number of sexual fantasies with the mother of his best friend in mind, especially at home and in bed, so hearing her say those things about him kindled them again. \"Uh, well, thanks. That's nice of you to say but frankly the girls favor Doug's type: you know, tall, good-looking, athletic. It is actually kind of unappealing to see so many of them throw themselves at the jocks.\"

Gary decided to try to regain some control of the situation and turn the tables. \"So, why haven't you remarried or dated more?\"

Caroline was actually surprised at Gary's boldness in asking the question but quickly turned it around again. \"Yes, well, that is a fair question, I guess, after what I had said. Many of the men I meet are either too overbearing and macho or too needy, looking for a mother to take care of them. Bleahh! And so long as man is physically fit, seems to care about himself, I don't care if he is shorter than I am. No, if I really wanted to be with someone, I would look for someone with your qualities, Gary: smart, loyal, someone who respects women, and is easy to get along with.\"

Gary's eyes were glued to Caroline's body as she said those things about him again. The look of lust in his eyes was apparent and he was still trying hard to cover his clearly larger erection. Gary laughed a nervous laugh. \"Well, I guess then it's too bad I'm not a few years older because I would love to date someone like yourself!\"

Caroline saw her opening and decided it was the moment. Gary wouldn't be home for 40 more minutes. Caroline walked over to Gary, who was seated at a stool on the island in Caroline's kitchen. Wearing her four-inch heeled boots, being taller, and the fact that Gary was seated on a stool, Caroline was a head taller than he was. Swiftly she unbuttoned the tight white silk shirt she has been wearing, exposing to Gary's bulging eyes her large, slightly sagging, but utterly beautiful and braless breasts. Because of the exaggerated height difference, those breasts were positioned right at Gary's face. \"Go on, Gary, suck them. I know you want to,\" Caroline said huskily.

At first Gary didn't move. His mind was reeling from this wholly unexpected development, this fantasy coming to life. Exceedingly slowly, as if he was making sure he wasn't in a dream or Caroline wasn't going to change her mind, Gary closed in on the first nipple, mouth open, as if he were about to receive the most succulent treat of a lifetime, which for him it was. Once his mouth connected, however, he began to lick and suck hungrily. First one breast then the other. Then back again. Finally, Caroline said, \"Come with me.\" And Gary eagerly followed her to her bedroom, but as they walked, her hand firmly grasping and pulling on his, Caroline said, \"Don't get overly excited, Gary. I can't make love to you, not yet, you're under age. It would be illegal.\" The look of disappointment on the boy's face was measurable.

“I wouldn't tell anyone!\" Gary blurted out.

\"I am sure you wouldn't but mistakes are made, things are discovered. Look, it is three months to your 18th birthday, we can wait until then and still enjoy each other's company in the meantime,\" she answered, as she drew him into her bedroom and sat Gary down on the bed.

Crazed with lust, but almost pouting with frustration, Gary asked, \"then why did you allow me to touch your breasts and why are we in your bedroom?\" His face seemed confused and yet hoping she was saying one thing while doing another.

\"I said we can enjoy each other's company, and we can. It can include, I think, you worshipping my breasts more, but you must do as I say, and you must exercise some self-discipline and control. It can involve some nudity on your part and pleasure, but do not attempt to push this further than we can. If you do, there will be consequences. Okay?\"

Disappointed but anxious to spend more time with this goddess before him, Gary replied: \"okay.\"

Smiling broadly---it was going so well---Caroline said, \"Very good. Now. When we are together and alone, I want you to call me 'Mistress.' It's a sign of respect for me and you must promise to do as I say. Also, go ahead and strip.\"

“Yes, mistress,\" Gary replied a little uncertainly and proceeded with a full blush Caroline found adorable to strip down to his underwear.

\"Take it all off.\" And Gary took off the last vestige of his privacy, presenting the sight of a naked teenage male before a fully clothed, if open shirted, tall, beautiful woman. His cock had been hard but was now a little limp from his initial embarrassment. She then laid Gary back on the bed, while sitting beside his naked form, and began kissing him aggressively on the mouth. Her tongue forced its way into his mouth, dominating it, exploring every corner, which he accepted. While doing so, she gently rubbed her breasts in a small circling motion against Gary's own chest and nipples. His penis returned almost instantly to a rock-hard state. Caroline also stroked the boy's body with one hand, up and down the side of his chest and leg. This went on for quite some time, with Caroline deliberately making Gary hotter and hotter, knowing he would soon do something he shouldn't.

Sure enough, Gary's arms, which had been around Caroline's chest as she kiss-tortured him, moved down to her skirt and made a slight attempt to take them off. Gary hoped that perhaps Caroline would be carried away in the excitement of their activities and take things further. Little did he understand how much Caroline had hoped he would try but not for the reasons he imagined.

\"STOP!\" she shouted and slapped Gary on the face. \"I told you there would be none of that, for now! I told you, you must do as I say! I told you if you didn't there would be consequences! Didn't I!?\"

Fearful that he had blown the best thing that had happened to him with woman so far in his life, Gary meekly replied, \"yes...mistress. I'm sorry, it won't happen again! Please, I just want to continue to be here with you!\"

Thrilled to hear him begging to stay, Caroline pressed her advantage as she intended. \"Sorry isn't going to be good enough, Gary. I said there would be consequences. I'll give you a choice: you can leave and we would never do this again or\" --- and Caroline paused for a second for effect--- \"you can be spanked for being the naughty boy that you are!\" Caroline did not doubt for a minute what Gary would choose. His cock had weakened again at this fear of what he had done, but otherwise it has been completely stiff all the time they had been together.

“I, I'll take the spanking,\" Gary answered quietly.

Caroline sat up on the bed and pointed to her lap. Gary got up and crawled over and laid himself down in the ancient spanking position of young children. Caroline grabbed Gary's arm, pulling it painfully behind and up his back, and began spanking with the other hand.

However, it was unlike any spanking Gary remembered as a child. Those had been hard and fast and soon over. Caroline was going less hard at first, slowly, rubbing his bottom after each blow, scolding him along the way. By the tenth spank, Gary's bottom was red and he was pleading her to stop. Yet, the more he begged, the more excited Caroline became. By the 20th blow, Caroline stopped, Gary's eyes were watery, and said over and over loudly, \"I'll behave, I promise, I won't do it again! Please stop!' She enjoyed it so much she had a small orgasm, although he didn't know that.

Once she let Gary up and he had wiped his eyes, she said, \"lay back down and we will begin again.\" Surprised, Gary gingerly laid down on his back again, and Caroline started kissing him again, and rubbing her breasts against his chest. After doing this long enough to be convinced Gary wouldn't try anything he shouldn't, she moved her breasts again to his mouth. \"Pleasure yourself, Gary. I told you there would be pleasure in this for you if you could behave. But don't let yourself cum until I say you can.\"

Gary was rock-hard again and could have come in seconds if he wanted to, but he stroked himself lightly enough to prevent that from happening. So lightly, at one point Caroline asked if he was obeying her, and he assured her he was, explaining he would come too soon otherwise. Finally after almost 15 minutes of this sensual torture, Caroline ordered: \"Cum now, Gary! Fast!” The boy immediately trebled his rate of action and brought himself to the best masturbatory orgasm of his life. Once completed, Caroline scooped up a healthy amount of cum on two fingers and put them in front of Gary's mouth. \"Suck my fingers clean.\" Hesitating only a moment, he did so.

\"There now. Was that not fun? Did you not get everything I promised?\"

\"Yes, Mistress.\"

\"Very good. Well, Gary, this is what I have to offer, for now. We can either forget this all happened today or do more of it as the opportunities allow us. It must be between us alone. No one else must know and certainly not Doug. Am I clear? Any hint of this at any time and it's over.\"

\"I would like nothing better than to continue with you---Mistress. I'll never breathe a word about it!”

\"Excellent. But just to make sure we are clear as to where this is headed. You are here to help me, to do as I say, completely. In effect, my young friend, I intend nothing less than to make a slave out of you when we are together. There will be a lot of pleasure for you, but a lot of service, too. And discipline, because I sense you are going to need it and I, frankly, find it very amusing to discipline young males. Doug has gotten too big for it, but I think you can take his place.\"

Turning red of embarrassment of the implied mention of his relative stature to Doug and to her, Gary answered with a mouth as dry as desert, \"yes mistress.\" He was at the moment excited and infatuated with this sexy, mature woman, the mother of his best friend. He wasn't sure what it was going to mean to be a \"slave\" when he was with her, but if it was anything like today, he was all in favor of being completely enslaved. The thought of submitting and obeying one of the girls he lusted after at school did not come quite as easily as the thought of being this beautiful woman's boy-slave. It was actually quite exciting as he swelled to the various imagined activities.

When Gary got home that evening, after helping Doug, who had arrived home a scant eight minutes after Mrs. Barron had told him to get dressed, he greeted his mother who was there as always. \"Oh, Gary,\" his mother said after he came through the door, \"Mrs. Barron called.\" Gary froze, inside in a state of panic. \"She simply wanted to compliment me, and you, for being a well-behaved guest in her house---although she did not mention you briefly acted up for a moment and then settled down after a minor scolding. (Gary involuntarily rubbed his behind.) But she said very nice things about you. Now, you make sure you keep doing what you were doing today. And when you are there, do as Mrs. Barron says. It's nice to hear nice things said about you.\"

Gary just grinned, partly at relief. \"I'll be down for dinner in a few minutes. I just have to use the bathroom first.\" Gary ran upstairs, shocked that Mrs. Barron would make any oblique reference about what happened today to his mother and yet unbelievably excited at this twist to her game. It took him only a minute to masturbate to an orgasm again behind the locked bathroom door.

The Second Time

Two days later, Gary was due to meet up with Doug at his house again to help with that day's math lesson. Doug typically got home on the sports late bus at 5:30. Gary, however, headed straight to Doug's house after he left school at 3:30. When he arrived, he let himself in as he usually did and Mrs. Barron came out from the kitchen to greet him, wearing the same black silk bra, but with black spandex pants, and the same heeled ankle boots as two days earlier.

“Gary, it's good to see you. How was school?\" And before he could answer, she swooped over him, grabbed his head and planted her full, luscious lips on his and began deeply kissing Gary. They pulled each other into a tight embrace and Gary's now surging erection could be felt by Caroline against her leg. \"Happy to see me, I see,\" Caroline laughed.

“Yes, Mrs. Barron---I mean, yes mistress!\"

“Good boy!\" Caroline smiled at her young friend. \"Let's go up to the bedroom, shall we? I want to continue where we were.\" As they entered the bedroom, Caroline ordered: \"Strip.\" Gary knew this time that it meant everything and so it all came off. Standing seven inches above him in her heels, Caroline ran her hands all over Gary's smooth, virtually hairless body. \"You are a handsome young man, Gary. I get wet from excitement just thinking of all delicious things we are going to do together in the coming weeks and months,\" she whispered in his ear, a full erection bobbing ever so slightly at every other words. \"But let's repeat some of last time. I call it conditioning.\" Caroline opened the top four buttons of her blouse, pulling the material aside, letting her braless breasts fall out. She once again drew Gary's mouth to them, ordering him to worship again.

After 15 minutes or so of this, Caroline laid Gary back on the bed again and began to kiss him, passionately and with control. But rather than let Gary embrace her as she had the first time, she pinned his wrists to the bed, arms stretched out. Gary could hardly the stand the raging erection he was having. He desperately wanted relief but knew that he dare not do anything Caroline did not order him to do.

\"You're a good kisser, Gary,\" Caroline told him after some time. \"I very much enjoy it. I must also say you are doing a very good job with that talented mouth of yours in worshiping my breasts. I look forward to your 18th birthday and seeing what else you’re capable of with your tongue!' Gary flushed red in embarrassment, guessing what Mrs. Barron had in mind, and not really sure what he thought of it.

“I want you to get up now and come brush my hair.\" Caroline got up from her sitting position on the bed and walked over to the chair at her cosmetics desk and mirror. She motioned Gary to follow her. She sat down and unleashed her long red hair from its tight bun and handed a brush to Gary, who now stood behind her, as she watched him in the mirror, with his powerful erection unabated. Gary wasn't sure where this was all going, he only knew for sure that he found Mrs. Barron enormously exciting and that if she wanted him to brush her hair, he could certainly do so. For a hundred strokes he brushed her hair as they made idle chit-chat about school, life, Doug, or other subjects.

“Lovely,\" Caroline said once Gary has finished. \"Time for your reward.\" She stood up and guided Gary by the arm back to the bed, his hard-on unabated during his caressing of her long, silky, red hair. \"Now, lay down and pleasure yourself, Gary, but do not come until I tell you that you may. Stop if you must to prevent yourself from cumming.\" Gary began to stroke his cock, slowly, because he was far too excited to hold back for long once a little friction was applied. Repeatedly, he would stop for a while as he felt his eruption build and waited until it subsided. It did not help matters that Caroline frequently caressed the boy's arms and chest while he did so, further adding to his sexual tension, which of course was exactly what Caroline had in mind.

Finally, Caroline ordered him: \"Beg me for it, Gary, beg me to give you permission to come.\"

Gary didn't need to be told a second time. \"Please, please, Mistress, please let me cum! I beg you to let me cum!\"

The sounds of genuine desperation in Gary's voice and the begging made Caroline quite wet. She, too, was ready for some relief. \"Very well, Gary. But you must do exactly as I say. First close your eyes.\" After Gary had done so, Caroline leaned over and pressed her breasts down on Gary's face, making it rather difficult for him to breathe and impossible to open his eyes. \"Do not suck. But make yourself come! NOW!\"

As Caroline clutched Gary's head with one hand, pressing his face into her buxom, she fingered herself with the other inside her pants. Meanwhile, Gary feverishly applied his own hands to his penis, bringing an explosion of cum within just a few seconds. Just as his was ending, Caroline came as well, though she managed to keep herself quiet and Gary, of course, was in no position to see a thing.

Once they were all cleaned up and Gary had put his clothes back, Caroline embraced the boy once more. \"Wonderful. A wonderful afternoon, Gary. I look forward to next time. I’ll see you in a couple of days, again?\"

“Yes, Mistress. We have a math test on Friday, so I plan to come over Thursday to help Doug study for it.\"

\"Lovely. One other thing, however. Do you masturbate when you are home and alone in bed?\"

Gary's face reddened at the question, but he saw no reason not to give a truthful answer. \"Uh, yes ma'am.\"

\"Am I now the object of your fantasies as you pleasure yourself?\"

“Uh, well, yes Mistress, I confess you are.\"

“Don't be shy or embarrassed about it, Gary. I love the idea. I wouldn't want or expect it any differently. We have something very special going right now and with the promise it will soon get much more wonderful and special. However,\" and Caroline gave a long pause for effect, \"you have a cell phone, do you not?\"

\"Yes, ma'am,\" Gary answered, quite unsure where this was leading.

“Good. From now on, when you are home in bed, at night, desiring to jack-off, I want you to call me on my cell phone for permission. We will do it together over the phone. Starting tonight. I know you will want to cum again tonight. Most boys your age cum two or three times a day. Gary certainly does, although he has no idea that I know that.\"

Gary didn't think he wanted to know how she knew that either and made no comment. \"But does that mean if you don't answer the phone, I cannot do it?\" he asked apprehensively.

Caroline gave him a smile and the twinkle in her eye suggested that she was considering this, but: \"No, if I do not answer, you may assume you have permission. If you were 35, I would have said yes, but since you are 17, I have no desire to drive you crazy, at least not yet. But I expect a call every time, regardless. Are we clear?\"

“Yes, ma'am,\" Gary answered with relief. \"We'd better get downstairs, Doug will be here soon.\" As Gary turned to leave the room, Caroline game him a hard smack on his butt.

That night, as he settled into his bed to bring himself off, he got out his cell phone and called his Mistress, feeling a degree of excitement and infatuation he had never felt in his life.

\"Hello?\"

“Uh, Mrs. Barron? It's Gary.\"

\"Well, I know that from the caller id.\"

\"Uh, right. Well, I'm in bed and I was wondering if I have permission to cum?\"

Caroline, who herself had now settled in bed to watch TV as Doug played some video games in the basement, could not believe how instantly excited she became when Gary called. The sense of excitement, thrill and above all power that was coursing through her in this new relationship with her son's best friend was an aphrodesiac she had not experienced before. \"Yes, my young slave,\" deliberately using that term on the phone, \"but do not cum without final permission. I intend to listen.\"

As Caroline heard the rustling on the other end of the line and heard Gary's breathing become more labored, she fingered herself, actually coming before he did. \"Don't forget to beg for it, Gary.\" And several times Gary begged to be allowed final release, moaning into the phone loudly when she finally said yes.

\"Good night,\" and Caroline hung up.

The Third Time

On Thursday, prior to Gary's arrival that afternoon, Caroline went shopping at one of the sex shops downtown in the red light district. The relationship with Gary was going far better than she had dreamed. But when she thought about it, why wouldn't it? She was a sexy, attractive, available older woman. Teenage boys have been having fantasies about such women for time immemorial. Especially ones like Gary, who did not fair well with girls his own age. And why was that, anyway? Perhaps it was her age or maturity, but she saw many fine qualities in Gary and did not understand why young girls wouldn't be interested in him. I suppose he is not what they would consider hip or cool, she thought, but this was hardly the first instance in which woman of her generation would not understand the woman of the younger generation. Their loss, she thought. Gary is my delicious toy and I intend to play with him for as much and as long as I can.

While Caroline owned a number of leather or fetish garments, which she would start wearing when she and Gary were together, she wanted a couple of small items. One was a black leather collar and a long metal leash. Caroline had always been turned on by the thought or image of men in collars and leashes held by strong, powerful woman. Gary would have to submit to that now. And the other was a sex toy. She was going to need all the time between now and his 18th birthday to train Gary in some degree of self-control. It is probably and impossible task, for a 17-year old, but she was going to have fun trying in any event. But the toy was for a little later.

When Gary arrived that afternoon, he virtually burst into Caroline's house. It's a good thing he has been doing this for years, she thought, or some people might get suspicious. Caroline had on a white robe today, but underneath she was wearing leather boots, skin-tight leather pants, and a leather vest that revealed a satisfying amount of her ample cleavage.

\"Hi Gary,\" Caroline called when she heard the door slam.

\"Hi Mrs. Barron, I mean, hello Mistress,\" Gary said as he walked into the kitchen and found himself looking at a white robe.

\"I was thinking,\" she started, \"that you are probably wondering what exactly I meant when I said you would have to be my slave.\" The look on Gary's face told her she was right. \"Well, as you can imagine from Tuesday, you have to do what I tell you to do---or not do something you want to do because I said you shouldn't. I like control, Gary, I like to control the men in my life. It's exciting. It is my greatest thrill. So you will do the things I tell you, when we are alone together, you will even start cleaning for me, but I doubt you will find that unpleasant as you will have to be nude and under my close and watchful eye.\" Caroline smiled at her boy-slave, expectantly.

\"Uh, yes, Mistress. I want to do anything you want me to do.\" In saying that, Gary meant it with the bottom of his heart.

\"Wonderful! Now, we both must look the part. If I am to be your dominant mistress, then I need to look something like this,\" and Caroline removed the robe as she walked from around the counter to stand in front of Gary. Her image took Gary's breath away. Above all, it was the skin-tight leather pants, which Gary suddenly and desperately wanted to feel with his hands. \"Take off your clothes, Gary, now.\"

As he did so, Caroline pulled at the brown bag she had left on the counter. Once Gary was naked she told him to get down on his knees, taking out of the bag, the leather collar and metal leash. Gary turned beet red as she put the collar on her slave, which Caroline never failed to find exciting. After all, giving embarrassment to her young friend was a form of control. She only wished she had opportunities outside of the house to do that. \"There! Now you look the part as well.\" And Caroline had Gary crawl over to the hall mirror where they both looked at both their images and both became excited at what they saw: an older, mature, but incredibly sexy woman in black leather holding the leash of a collared teenage male on his knees before her.

\"Bend down, Gary, kiss my boots.\" He hesitated only a second, now quite used to doing as Mrs. Barron told him to do. He kissed her boots over and over. \"Now lick them, Gary, until I tell you to stop.\" And Gary did so, first working the right boot and then the left. \"Wonderful. Come. You may stand. Let's walk upstairs.\" Caroline led Gary by the leash to her bedroom. She sat in her chair, motioning Gary down on his knees again. \"Take off my boots.\" Gary carefully undid the laces, finally freeing Caroline's feet. \"Make yourself comfortable Gary, because you are going to give me a pedicure.\" For the next 40 minutes, Gary did that, following Caroline's detailed instructions, finally finishing with applying bright red polish, the whole exercise he found surprisingly erotic.

\"You have actually done a creditable job, Gary for your first time. I almost feel bad about what happens next.\" Gary looked alarmed at first, thinking something really bad was going to happen. \"Time for your next spanking.\"

Gary was partly relieved but also a little petulant. \"But I didn't do anything wrong! I have behaved myself!\" he pleaded.

\"Well, that's true, up until that little tantrum right there. But you forget my young slave, I really enjoy disciplining young men. I almost felt guilty when Doug would get a spanking as he grew up, because I secretly enjoyed it so much. Now, however, there isn't the slightest trace of guilt. This is purely for my pleasure.\"

So again Caroline made Gary crawl on to her lap, pinning his arm and clamping his penis between her leather-clad thighs. The strokes that Caroline administered were as erotically delivered as before, even more so. She noticed this time, however, that Gary wasn't growing any softer, if anything, his hard-on was become more hard. And she realized that with blow, Gary's body twitched some, and his penis rubbed between her firmly clamped thighs. She knew it was exciting him, even if he found the spanking uncomfortable. She decided to proceed to see what would happen. By the ninth or tenth stroke, Gary spoke up.

\"Mistress, I am going to cum!\" Caroline was thrilled. Gary was about to come while being in one of the most humiliating positions a young male could be in, while still suffering some moderate pain. Rather than stop, however, Caroline said: \"Oh really, you like this, do you?\" It was more of a statement than a question and she did not expect Gary to answer. He didn't, in large part because she deliberately picked up the pace of her strokes and thus the rubbing of Gary's cock. In three or four more spanks, Gary's breathing increasing, finally saying, \"oh, God, Mistress, please, ah, AAAHHHHHHHHHH,\" cumming violently inside Caroline's thighs. Once he finished, Caroline spanked a few times more, especially hard.

\"Get up, Gary, and clean up this mess,\" Caroline finally announced. \"With your tongue.\" And Gary got down on his knees and licked all of his cum off his Mistress's leather pants and a little that had gotten on the bed.

“I hope you enjoyed that!\"

\"Oh, yes, Mistress, thank you.\"

\"Well, now is the time to pay. I want some fun, too.\" Caroline laid Gary back on the bed, undid her leather vest, pinning Gary's arms, kissing him and having him suck her breasts. Then she repeatedly smothered Gary's face with her bosom, denying him air repeatedly for up to 90 seconds at a time. The utter control she felt, and she knew by now that the control was quite real, for she was clearly stronger than Gary, as well as having the weight advantage over him, was a complete aphrodesiac. Finally, she had Gary cover his groin with his arm, which allowed her to grind herself to an orgasm on it and prevent Gary from being stimulated to another himself.

For her part, Caroline at times could barely stand the wait herself and several times nearly succumbed to the temptation to fuck Gary during their playtime together. But she resisted. She wanted to wait, for the torment it was causing Gary. It excited her to see him so desperate to have her, yet be constantly denied.

The Device

When Gary arrived at the Barron residence the following week, Caroline explained a new conditioning program.

“Do you see this device, Gary? It’s tube with a pump designed to excite men. It fits over your cock and is designed to simulate a woman’s pussy. We are going to start practicing with this so you do not cum so quickly. When you are 18, I want you to last for your first time.” For the next hour and for the next several months each time they were together, Caroline would force Gary to practice holding back his orgasm. It usually did not work.

The Birthday

On his 18th birthday, Gary could barely stand to wait for school to come to an end that day. Nevertheless, when it let out, he played it cool, told Doug he'd see him tonight and headed on his way to Doug's house. He called out as he usually did when he closed the door behind him. As he walked past the doorway to the living room, he did not see Caroline standing there to the side out of eyeshot. She immediately stepped into the hall and grabbed Gary quite firmly around the neck with her left arm. She was wearing long black leather gloves. \"Happy Birthday, Gary,\" she whispered into his ear. \"I've waited for this day for ages.\" As she said this, Caroline ever so lightly stroked Gary's face and arms. She moved her hand down to Gary's crotch and felt his hardness. \"Oh, you're happy to be here, too?\"

\"Yes, Mistress,\" Gary whispered back.

\"I'm so very glad, my young slave, because today I intend to rape you, undoubtedly more than once.\" Indeed, Caroline thought they'd be able to do it three times before Doug got home. Gary was 17---18---after all. \"Today,\" Caroline continued to whisper, \"I make you mine in every way. It will be a joyous union, Gary, but remember you do absolutely nothing you are not told to do.\"

\"Yes, Mistress.\"

\"Now, let us begin.\" With that, Caroline, still gripping Gary tightly by the neck, ripped his t-shirt right off his body. She then unsnapped his shorts and pushed them and his underwear down. \"Kick off your sneakers.\" Gary did so and Caroline was able to push his shorts down far enough until they fell down on their own. She decided to let him keep his socks on. She found him naked but with socks quite adorable. \"Don't move.\" Caroline released Gary's neck and quickly slipped the now quite familiar collar with leashed around him. \"Now, get down on your hands and knees and crawl behind me. Make sure you keep up.\"

Gary did as was told and for the first time saw Caroline in full view. She was wearing ankle-high black boots with four-inch heels, fishnet stockings up to the top of her thighs, very tight, very short black latex shorts, and the leather gloves. Her chest was clearly bare, though he could not see it as he crawled behind her.

Once in the bedroom, Caroline ordered Gary to lie on his back and he got to see her magnificent breasts, nipples firm and protruding with obvious desire. She secured his arms to the two posts above him and cuffed his feet together and then tying them down in the center of the king-sized bed. Gary now also saw that her shorts had a large opening in their center, showing Caroline to be a true redhead. Her bush was neat and beautifully trimmed. For her part, Caroline surveyed her handiwork, reflecting on how long it had been since she first wanted this boy, this young man, so helpless before her. Despite a terrific urge to just jump him at this point, she laid down beside Gary, pushing her breasts against his chest, fondling his balls first (but not his supercharged cock) and then his nipples, pinching and twisting them in a mildly painful, but not unpleasant way, smiling at all times, oohing and aahing every time Gary yelped, feigning sympathy for every mild discomfort she inflicted upon him.

Caroline then spent some time kissing him, slowly working herself on top of Gary's stomach. She pressed her breasts against his face, first to smother him and then to have him use his tongue to worship them as he had so often these past five months.

\"Now, Gary, I've wanted for so long to feel that warm, talented tongue of yours on me,\" she said as she pulled her groin up over his chest to his face, sitting up high to do so. \"You will now lick and suck and penetrate me with your tongue until I tell you to stop.\" With that Caroline dragged her pussy over Gary's mouth and pressed down, gently at first but eventually with more force. Caroline moaned and groaned at the sensations electrifying her body. Her excitement at the moment was almost as great as Gary's when he walked through the door, so it did not take the boy long to bring her to a thundering orgasm, drenching his mouth. \"Wonderful!\" She did not stop, however, although she let up on the pressure a bit, allowing Gary to work her over as best he could for the first time.

Finally, she stopped that. \"All right, Gary, here it comes. Remember to control yourself, hold back for as long as you can, think of other things.\" Caroline nearly came before she began, thinking about she was about to deflower the teenage male. Seducing, taking, and enslaving a teenage virgin male was a long-standing dream come true!

\"Oh, God, thank you, Mistress!\"

Caroline moved down and took Gary's hard cock deep inside her pussy. He held out maybe 30 seconds, which was better than Caroline thought he would do, under the circumstances. He came screaming but so did she. That was okay because she came again as well and was almost as loud. She had wanted to fuck this young man---she liked to think of it as raping him---for months. Once they both had come, Caroline lied down on top of Gary, but otherwise made no move to disentangle herself from his body. For Gary's part, he had wanted nothing more than fuck his best friend's mother for months and actually found himself crying a little at how good, how relieved he felt, and how wonderful the whole experience has been. Caroline was shocked to find Gary shedding tears.

\"Gary, what is the matter?\" she asked, not a little bit concerned.

\"Don't worry, Mistress,\" Gary answered, trying desperately to get control of himself. \"I was just overwhelmed by the sheer joy I felt at the moment. It was unlike anything I have ever experienced in my life. Thank you, thank you, thank you.\"

Caroline smiled at her young sex slave, feeling both maternal affection and lascivious, predatory thoughts. \"I'm glad, Gary. I haven't taken a virgin since I was 16. It's been a real joy for me as well. But we aren't done. Far from it. But first, here, nurse on this, I promise you will feel better,\" offering her breast to him. And Gary did, performing an act of security and intimacy ingrained in young men when they were babies.

After some time after this, with Gary still ensconced in her vagina, Caroline was fully aware that Gary had not softened up much and, to the extent that he had, he was now hard again. Caroline began to move to take Gary a second time. But this time, she was rougher, pinching Gary repeatedly and painfully on his nipples, and as they approached orgasm together again, she pulled Gary's face into her breasts with her hands, smothering him to the point where he couldn't breath for the last minute of pounding on his cock until they both screamed again. She could feel him start to struggle for breath under him but of course there was no escape. His terror excited her. Caroline felt energized by her exertions, particularly as she hurt and smothered her slave in the ultimate act of physical conquest. Gary's mind was a mix sensations and emotions. He was excited, pained, and terrified at the same time by what Caroline, his Mistress, was doing to him. But he did not want her to stop, he wanted to do or let her do whatever she wanted to him that would make her happy and give her pleasure. When they both came, she released him and got off, allowing him to catch his breath.

They both were sweaty, gooey, and reeked of sex. \"We must shower, Gary. Doug won't be home for an hour, your hair will dry by then. Come, we'll go in together.\" She released Gary from his bonds and the boy staggered a bit into the bathroom, where Caroline began running the oversized shower with several heads. She took off her boots and removed Gary's collar. Once inside the glass doors, she handed the soap to Gary and ordered him to wash her body. Gary did so reverently, exploring every crack and crevice of Caroline's body with his soapy hands under the guise of cleaning but they both knew it was more than that. Once they both were clean, however, Caroline stopped Gary from turning off the water and embraced him with long, passionate, dominating kisses. She forced Gary to his knees and then shoved his head into her crotch.

\"Lick me, Gary, lick and suck until I tell you to stop.\" Gary did as he was told, with an enthusiasm Caroline repeatedly praised. She then ordered Gary to lie down and with the water streaming over them, she planted her ass squarely on Gary's mouth. \"Lick it, Gary, you've made it clean, now worship my asshole, any slave of mine must worship me there.\" Gary was shocked at how excited he was becoming by this. Although the image of Caroline's beautiful cheeks right at this eyes, with water streaming down her back and her long red hair all wet certainly helped. As his erection grew stronger, Caroline noticed and eventually began lubricate it with soap and her hands. And once Gary had licked her rosebud long enough, she increased her tempo and brought the boy to his third orgasm of the afternoon.

They the dried off, got dressed, Gary helped Doug when he got home, and then went out to dinner with his parents. At 11:00 that night, he called Caroline for permission to come one more time, which she gave, but ordered him to whisper into the phone his thanks to his Mistress and praise for her over and over. She ordered him to describe what he was fantasizing about as he did it. She knew she was his fantasy and thrilled to hear him describe an almost repeat of their afternoon before hanging up.

From Behind

For the succeeding several weeks, Caroline's and Gary's couplings continued but with less intensity, usually, and more domination. Caroline continued to make Gary work for his pleasure and Caroline loved watching him do it, whether it was her hair, her toes, or her bathroom floor. It ended happily enough for them both, though the positions and details varied each time. Finally, however, she decided she wanted to rape Gary from behind. No act was more dominating by a female over a male than taking a slave with a strap-on dildo.

Caroline planned to do it the next time Gary was going to come by, Thursday. She warned him ahead of time the night before on the phone that she was going to take their relationship to a new level the next day and that he should be mentally prepared for it.

Gary arrived that day with not a little bit of trepidation. He was enjoying his relationship with Caroline more than he ever imagined but knew perfectly well how different it was. His fantasies had never been quite like this, though he did see some resemblance. His fantasies often revolved around having sex with an older women, usually the teachers rather than his fellow students. In his fantasies they always seduced him, controlled the relationship, were on top during sex. Since falling in with Caroline, Gary had read a lot more on the internet about female domination and male submission, admittedly most of it pornography, but he was aware that there were a lot of things they did not do and that he did not want to do and hoped that Caroline would not do them. Still, whatever she came up with, he knew he could not stop. He was devoted to his Mistress and did not want to stop enjoying what she did with him and to him.

After Gary let himself in, he called out to Caroline to let her know he had arrived. \"Come to the bedroom Gary, immediately.\" Caroline's voice was loud and authoritative, she wanted to proceed at once. When Gary saw her, she looked as breathtakingly beautiful as always, dress in tall black patent leather boots, crotchless leather shorts, a leather halter, and gloves. Her hair, unusually, was tied up in a tight bun on her head. It was a severe and powerful look.

\"Strip. Now.\" It was all Caroline said. Gary did so as quickly as he could and was soon kneeling before Caroline's boots with his cock fully erect and already glistening with droplets of precum. Caroline proceeded to put leather cuffs on his wrists and ankles as well as his collar on his neck. \"You may kiss my boots.\" Gary had learned over the past few weeks that \"kiss my boots\" meant exactly that but after an appropriate amount of time also meant that he was to proceed with his kisses to Caroline's crotch and worship her pussy until she came. After she did so, Caroline got up from the bed and began to get some things out of her drawer. First, she laid out a thick and heavy rubber mat across part of the bed, squirting a liberal amount of lubricant gel over its center when she had done so.

\"Lay on stomach on the mat, Gary, with you legs on the floor and your cock square on the lubricant.\" Gary did so, although he found the lubricant rather cold to his initial touch but sooner found his body warming it and the mat up. As this proceeded, Caroline chained his legs to the bed, pulling them far apart before attaching one end to his ankle cuffs and the other to opposite bed posts. She then did the same thing with his hands, until he he was stretched pretty tight, but with half his body on the bed, bent at the waste and the other half vertical from the floor.

\"There. That will do nicely my young slave.\" Caroline lied down on top of Gary's back, pushing his body against the mat and the oozing cream and then whispered into his ear: \"No boy is truly a slave to his Mistress until he has been raped by her with a strap-on dildo. That's what we’re going to do today. I am going to rape you---from behind. What do you think of that Gary?\"

Gary knew it. He did not like the idea. \"I don't think I really like the idea, Mistress.\"

\"I'm sure you don't. I'm willing to listen to you beg me not to do it. I'm always up for some begging.\"

Gary whispered back, with some genuine fear in his voice, \"please, please, please, Mistress, don't rape me with your strap-on, please.\" Gary repeated this several times, until finally Caroline laughed with mock sympathy.

\"I think not. We'll proceed just the same.\" Gary was not surprised and his hard-on had wilted considerably. Caroline got up from the bed and put on her \"cock.\" It wasn't a big one, she did not want to hurt Gary after all and it was his first time. But before beginning, she knew Gary needed a little warming up and encouragement if this was going to be the experience she wanted it to be. First she lubed the dildo and then Gary's ass. But before she began, she stroked and caressed Gary all over, bringing his cock back to life as he involuntarily responded to Caroline's sexual attentions.

And then he heard her say, 'relax, here we go.\" Gary at first felt the pressure on his anus and then felt it give way, somewhat uncomfortably, as the dildo at first penetrated and then found its way all the way in. Caroline went in and out a few times before pushing a little harder and laying back down on top of Gary, whispering again. \"You know what you are, Gary? You're my bitch. Say it for me. Say you are Caroline's bitch.\"

\"I am Caroline's bitch.\"

\"Say it again,\" Caroline ordered as she stood up again and began to thrust into Gary's ass more vigorously. \"Say it over and over again, loud, until I tell you to stop!\"

Gary began repeating his fate, not quite shouting but loud enough that if anyone else in the house had been home, they would have heard him. \"I am Caroline's bitch! I am Caroline's bitch! I am Caroline's bitch.\" As Gary repeated his line, Caroline's thrusting grew to a bit more intensity such that he could feel his whole body move, hearing her body slapping against his butt. But as his whole body moved, so did his well-lubricated cock against the now warm rubber mat. The dildo in his ass was hardly comfortable but the whole experience was exciting him intensely and he knew he was going to come. He knew Caroline meant for him to come as she fucked him. And after about a minute more, he screamed an orgasm and Caroline only stopped thrusting when he stopped moaning.

For her part, Caroline came as well as she fucked Gary in the ass. Her thoughts dwelled on the fact this 18-year old boy was her sex slave and that she was fucking him in the ass with a dildo and the dildo was putting pressure on her crotch with each thrust, leading her to come as well.

After they had cleaned up---Gary needed a shower---they resumed more conventional activities shared between a dominant female and a servile male.

The Future

The school year was winding down and all the students were deciding where they were going to college. Gary and Doug were no different. Doug would be entering a decent, though not top tier liberal arts college about two hundred miles away. Gary had a choice. Of the several schools he had gotten into, he had narrowed them down to two. A good school right here at home. It had the advantage of keeping him in the same town as Caroline or a slightly better school about 300 miles to the north. Ordinarily he would have gone north. His parents had put their house on the market in anticipation of early retirement farther south. They had only stayed as long as they did so he could finish school. His home, in effect, was moving whether he did or not. But he wasn't going to make this decision without Caroline. He knew in his heart of hearts that this relationship was not going to go on forever. He wasn't going to marry the mother of his best friend after all. And he didn't think that he and Caroline loved each in that way. They loved each other all right, but more as lustful, very best friends, rather than as boyfriend and girlfriend. Caroline had always made that rather clear: he was a piece of meat to her, one she was very fond of, but there was no room for cupid. Still, by no means did he want their relationship to end now. He enjoyed it far too much and saw no reason why it could not continue while he was in college. But did Caroline think that way? They would have to talk before he made his decision.

Gary arrived at Caroline's house 20 minutes before Doug was to get home. She was surprised. Gary wasn't due to come today at all and now that he has, there really wasn't any time for them to do anything.

\"Hi Caroline,\" Gary said announcing his presence.

\"Why, hello,\" Caroline said a little surprised. \"I didn't expect to see you today and it is a little late.\"

\"I know. I actually came to talk.\"

\"Oh, what do we need to talk about? Your lingerie chafing?\" Gary turned beet-red at this comment, a reference to Caroline's habit from time to time of ordering him to wear women's underwear under his clothes on some school days as a constant reminder that he belonged to her. It had that effect as well as giving a near constant hard-on if he wasn't otherwise focused on other things.

\"No, no. It's about next year and what I am going to do.\"

Caroline looked at him. \"Look, Gary, I know we've enjoyed our time together but I've always known that you would have to go to college. That is something you must do. You certainly can't sacrifice that to stay here with me. If for no other reason than I have no intention of supporting you for the rest of your life just to be my sex slave.\"

\"No, I understand that. I agree with that. I want to go to college. But what if I went to college and stayed in town?\" Gary went on to explain the choice he had. \"What I want to know is, if I stayed in town would you want to continue? If not, I think it would be best all around if I went north.\"

Caroline was surprised at this turn of events. She had always assumed that Gary would move away to college and, knowing his parents were leaving the area, figured their fun and games would be over. But now the prospect appeared to continue, possibly for years to come! Caroline walked over to Gary, grabbed him and firmly and deeply kissed him. \"Gary, if you stay, yes I would keep you. Our relationship is one of the very highlights of my life. I know eventually that you will have to move on in life, but the prospect of having you around under my heel, literally, for four more years is one I would relish!\"

Gary smiled hugely and at that moment Doug came in. \"Hey dude, what's up? We weren't supposed to study today.\"

\"No, I just came by to tell you---I was telling your mother---that I have decided to go to Elliott, which means I'll be around. But since my parents are moving, I won't be able to save all the money on room and board as I was hoping.\"

\"Why don't you stay here?\" Doug asked.

Caroline and Gary looked at him. \"Hey,\" he said, \"it makes sense. I'm leaving. You could take my room---redo it the way you want---it would save you a bundle. \"It's not like the house couldn’t hold three of us when I come home to visit.\"

Gary and Doug looked at Caroline.

In a split second after Doug finished, Caroline imagined what it could be like. This young man would live in her house full-time and Doug wouldn't be here. It opened up all sorts of possibilities. He could be naked when he wasn't at the college, in class. He would be available to satisfy her sexual urges whenever she had them! She could introduce numerous new games with him. She would increase his tolerance for pain, for example. He could be in bondage for days at a time! Finally Caroline spoke: \"Why that would be a great idea!!\"

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