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Her Son's Best Friend, Part II
(It may be longer than two parts.)
Almost Six Years Later
Caroline knew it would have to come to an end. For the past six years, while Gary shared a room in her house, earned first a bachelor's degree and now almost finished with a master's degree, he was her lover and her slave. Caroline dominated Gary sexually more completely than she had ever dominated anyone in her life. She reflected fondly on the depths of submission and depravity to which she subjected Gary during that time, points at which she had not even imagined six years ago as Gary first succumbed to her designs for his place in her life. When out of the house, Gary always wore female lingerie or chastity belts or both. When at home, Gary was always completely naked except for his leather collar, whether he was with Caroline, or doing chores, or even just sitting and doing his college homework. Gary performed service and sexual activity on Caroline whenever she demanded, which was pretty much daily, often more than once a day. If Gary didn't spend at least an hour a day with his head clamped between her thighs just worshipping her pussy, it was a slow day.
When Caroline had first set her sights on Gary, he knew very little about the ways of women, truly, and what he has learned over the past six years was more than most men knew, but still resembled an incredibly narrow range of women. Caroline realized that she has without a doubt ruined Gary for most other women. He would be incapable of functioning sexually in a "normal" relationship. Caroline regretted this, but in the end she would not have done anything different. She loved Gary as her lover and her slave but it was time for him to move on. Oh, she thought, he could stay with her forever, but that would be a waste of a talented young man with a gift for mathematics who could make a real contribution to the world. Unfortunately, the kinds of jobs and the contributions Gary could make could not be done in this town. He had to seek his fortune elsewhere, without her, because she had no intention of uprooting her life here.
She would have to tell him soon. She was not sure what thought he had given to the idea that he must move on in a few months, but he certainly must suspect what's coming, unless he thinks I am not planning to let him go.
Caroline took some consolation in the situation with the knowledge that Gary was not, apparently, incapable of interacting with the opposite sex outside of her home. In the past year, Gary had struck up a platonic friendship with Heather, a fellow graduate student, but in the engineering department. Heather was about as tall as Gary, around 5'7" and had a deceptively pretty face that was not at all obvious from a first glance, as it was hidden behind not-very-flattering glasses and a bit of late acne. She was the same age as Gary now, 24. Of course, when she came by the house, all was perfectly normal, nothing at all hinted at the unusual relationship Caroline had with Heather's friend.
A few days after Caroline had contemplated her dilemma about what to do about Gary, Heather dropped in, waiting for Gary to get out of classes. They planned to do some studying and, Heather hoped, to grab something to eat.
"Hi Caroline," Heather said as Caroline opened the door, "I assume Gary isn't back from classes yet. Do you mind if I hang out here until he gets back? We're planning to study for Friday's test."
"Not at all dear, do come in."
Caroline wasn't sure why she said what said next, perhaps because it seemed like a natural line of conversation for a 45-year old "normal" landlady. "It's so nice to see that Gary has found such a nice person as a girlfriend." (It was a comment Caroline never would have made in front of Gary, and Heather was almost never at her house by herself.)
Heather sighed deeply. "Oh, I am not his girlfriend. I wish I were, but I am not. Gary has never shown much interest in me, or any other girl for that matter, and has brushed me off the couple of times I mentioned it would nice to be something more than just friends. I decided he is gay but doesn't want to talk about."
Before she could stop herself, Caroline laughed and blurted, "Oh, he's not gay!"
Heather studied Caroline closely now and did not say anything for a long time. Caroline, surprising herself, grew uncomfortable in the silence and under the gaze of this obviously intelligent young woman.
"You said that as if you know it for a fact but yet I have never seen or heard him discuss a girlfriend." Heather finally made this statement as a set of facts, waiting to see if Caroline would challenge them.
Caroline felt that any denial at this point wouldn't be believable, but she tried anyway. "Oh, no, no, I just don't think he is gay, that's all." It sounded lame and both Caroline and Heather knew it.
"Look, Mrs. Barron," ---Caroline noted the sudden formality--- "I like Gary a lot. He is the nicest, sweetest guy I know. Always very generous with time and help, and by far the most respectful of women in the math and engineering departments. I'd appreciate you helping me understand him. You probably know him better after these past six years than anyone else."
Caroline now realized she would have to be more forthcoming, especially since Heather was just the type of woman that Caroline had ruined Gary for.
"All right dear, I'll try to explain. But please don't be judgmental of him. Gary could use friends like you and I don't want to say anything that will ruin that."
"I doubt there is anything you could say that would stop me from liking him." Indeed, Heather thought to herself, I love him. Nothing could be worse than this feeling of unrequited love.
Caroline ventured forth. "If Gary doesn't show much interest in other women, it's, well, because he and I are lovers, and have been since he first went to college."
Heather's mouth dropped open, and then tears glistened in her eyes but she didn't lose herself to her emotions. "Do you love him? Does he love you?"
"Well, it is clear we enjoy each other's company tremendously, but it is a little hard to explain because our relationship is a bit unusual."
"How?" Heather asked, feeling not a little bit of anger welling inside of her.
"Gary. . . Gary is my slave, my sex slave. I love to dominate him and he enjoys submitting to me."
"You mean . . . as in black leather, whips, and bondage?"
"Yes."
Heather continued, slowly winning the struggle with her emotions, "so he really enjoys that or is it something you force on him?"
"Well, I suppose in the beginning I did force the issue. I made it clear as I seduced him---and I admit I did seduce him---that if we were going to enjoy an intimate relationship, it would have to be this way. And at 18, a young male would be willing to do almost anything for regular sex."
"I see." For a full minute Heather said nothing and Caroline didn't either. Finally, Heather got up: "I have to go, Please tell Gary I had to cancel. Give him any excuse you want.
"Heather. . ." But it was too late, she had moved swiftly out of the house and showed no desire to continue the conversation. That night, Gary tried to call to find out why Heather had cancelled but she had turned off her cell phone.
The next day, Heather dropped in to see Caroline when she knew Gary wouldn't be there.
"Heather!" Caroline said in surprise as she opened the door. "I'm so glad you came back. I feel I need to explain more."
"It's okay Caroline. You don't have to explain anything. I came back because I have a proposition for you." Caroline noted the use of her first name, Heather was deliberately making her equal. After they sat down and Caroline poured some tea, Heather stated baldly: "I want to propose a trade: Gary for my brother."
"What?!?"
"You heard me perfectly well. I want Gary. I love him and I'll take him the way you trained him and continue it if that is what he wants. We all know Gary is leaving anyway, but maybe we can do it in a way that sends him into my arms. In return, I'll convince my brother, Christopher, to live here. He is planning on attending college here as well, he just turned 18, and I happen to know he'll love what you will do with and to him. So how about it? The only thing is, to get this deal, you start pushing Gary into my arms immediately. I want him and I have wanted him practically since the day I met him."
Caroline's mind reeled with what she had just heard. "How do you know your brother would love to be dominated, to be sexually enslaved by a woman, particularly a woman much older than himself? I'm 45 now."
"Easy. I more than once came across his stash of pornography he hides from our parents. The one recurring theme over and over in almost everything he had was a strong, powerful woman dominating a weak or submissive male. Stories, letters, pictures, it was all the same. I actually found it quite intriguing myself, but I've never really tried it."
Caroline was now thinking that not only could this work, but how it would work. Moreover, it would be the best possible outcome, to release Gary to another woman willing to dominate him but yet also love him. All of the heartbreak she was sure Gary might have otherwise endured could be eliminated. Heather and Gary are friends. All he has to do is see her as a woman who would love to go with him, and dominate him, and the rest would follow.
"All right, Heather. I like the idea. I will entrust Gary to you even if it doesn't work out with your brother, but I would dearly love another nice young man to do my bidding."
"Oh, he'll be yours all right, the only question I have to think about is whether to put it to him up front, or simply convince him to live here, and then I guess he would easily fall under your sway. You would be like gasoline to his fire."
"Very well. Let's talk about how to make it work with you and Gary. I think the best thing to do is to have you observe us together for a bit, to see what we do, how he behaves, and what he likes. Then, with him blind-folded, bring you into our get togethers. This has happened occasionally in the past when a couple of dear friends from college would visit. I could then leave and let you have him for a while, but you will have to decide when and how to tell him. If you do it right, he will embrace you. I am sure he knows that he and I cannot continue on after this year, but I have not yet told him that directly. I think he wants me to push him out, rather than tell me he has to go. I haven't done it yet."
Heather was nervous about this prospect: it was an all or nothing gamble, but knew she had to take it. If Gary never showed any interest in her because he already had everything he wanted at Caroline's, then perhaps the prospect of continuing on with her would permanently change the shape of their relationship the way she wanted.
Heather stated, "Gary will be here soon. He's expecting us to study. I called him this morning, feigning illness yesterday, and suggest we pick up where we left off today. Do we start now or wait until another time?"
"Let's do it tomorrow. Your test will be over and Gary's coming straight here. Here's a key to the house and you can come after classes. Gary is due home at 4:00, where he already knows we will be "playing" immediately. When you come in, go to my room. You'll find plenty of appropriate clothing in my bureaus and closets. They will be a little big on you, but you must look the part for it to work. Then hide in the closet until I tell you to come out. Have you read enough about this to understand the psychology behind dominating a male?"
"I think so. I guess we'll see."
"In the meantime, why don't you go home and have a conversation with your brother." Heather could see the excitement in Caroline's eyes. She clearly had a desire for fresh meat.
"Okay, but let take of picture you first. I think that will help sell the deal."
Caroline was about to smile when she said: "wait, let me put on some more appropriate clothes." Caroline left and five minutes later came back wearing tall, high-heeled leather boots, tight black shorts, and a tight black t-shirt, accentuating her magnificent breasts. Sexy to the vanilla observer, but sure to turn-on a submissive young male.
Selling the Deal
When Heather arrived back at her apartment, having thought all day yesterday and the way home what she would say, she immediately dialed her younger brother. "Hi Chris. I've got good news. I've found a great place for you to live next year. You'll love it." Only Heather called him Chris, because he hated it.
Christopher was surprised. "What are you talking about? I'm planning on living in the dorms."
"Well, you see, I think you'll like this place better. You would be renting a room in a house, the same room used by a friend of mine whose leaving. The landlady is just your type. You'll like her."
"And why would I want to live in that situation? The dorm has got to be more fun."
Heather warmed to her subject carefully. "Chris, I have a confession to make. I know about you. I know what you like."
Christopher hesitated briefly, wondering if his sister was talking generally or really knew more about him than he wanted her to. "You know many things I like. What are you getting at, Heather?"
"I know about your pornography stash. I have read it all."
After a very long silence, Christopher only said, "oh." And then, "um, so?"
"Look baby brother, I'm cool with it. You like what you like. I admit, I found your stuff exciting, too, but from the woman's perspective. Really, it's okay. I won't tell anyone."
"Well, then, why are we having this conversation?"
Heather chose her next words carefully. "Let's face it, Chris, you want to be dominated, sexually, by a woman. It is what you have always wanted. Some of the dates in your pornography stash date back to when you were 12. Your every sexual thought since you first had them were about being dominated, weren't they?"
"Uh, I guess so." Even so, just having the conversation about domination was giving Christopher a hard-on.
"The landlady who owns the house where you would rent a room, she'd dominate you, she likes bondage and domination, she particularly likes to dominate young men. She's beautiful, here let me send you the picture."
Within a few seconds, Christopher was looking at the picture of Caroline Barron in black books and skin tight clothing. His cock grew even harder.
"And she's tall, Chris, four or five inches taller than you." Heather had noticed the large number of amazon-themed stories in her brother's stash. "This is your opportunity to live the sexual adventure you have always wanted."
Christopher was thinking with his head now, but not the one with a brain in it. "Sh- Shouldn't I meet or speak with her or something?" But then he thought, who am I kidding. I am going to do this. After all, if it doesn't work, I could always leave.
"Tell you what, I'll have her call you, okay?"
Mouth dry, Chris replied, "okay, sure, that's a good idea. Bye."
Heather immediately called Caroline, gave her the details, let her take it from there.
Capturing Gary
When Heather arrived the next day, she was excited about what was coming, but still couldn't wait to ask. "So, did you call Chris?"
"Oh, yes," Caroline replied. "Thank you. He sounds really sweet, I love them that way you know. He was already calling me mistress by the end of the conversation. We exchanged some emails and pictures. He needs someone like me very badly, doesn't he?"
"Yeah, but I expect you won't hurt---I mean, harm---him. You’ll treat him well? He is still my brother, after all."
"Of course, I'll treat him as well as I have treated Gary, the only difference is that I'll be able to move things along much faster with Christopher."
With that Heather bounded up the stairs, her heart pounding in her chest so hard she thought it would break her open.
Heather found among Caroline's things enough to make her look like a totally hot dominatrix. She put on a pair of her boots, two sizes too big, but not unmanageable. A black hat, black gloves, and a black corset she could tighten completed her outfit. She then staked out a position in the closet that afforded her a clear view of the bed area from the crack in the door.
It wasn't long before Heather had someone enter the house. She had left the door to the bedroom open and listened carefully for Caroline and Gary to come upstairs. She heard Gary call a "hi Caroline" and Caroline respond with: "no chores today, Gary, I want you upstairs right away." Gary answered with a "yes Mistress."
A minute or two later, Heather was shocked and titillated by what she saw. Gary had entered the room wearing nothing but a tight-fitting pair of pink women's panties with decorative lace. It could barely contain his clearly bulging erection. Gary immediately dropped to his knees, clearly waiting for Caroline, who arrived about a minute later.
Caroline knew exactly what she wanted Gary to do. It would be a sensual, service-oriented day for Gary. She wanted Heather to get excited by what she was going to see, to want it for herself, rather than be repelled by one of her more intense sessions with her slave. Caroline commanded Gary to brush her hair and give her a massage.
The effect on Heather was precisely what Caroline wanted. Heather was surprised how hard Gary remained doing these things to Caroline. He was sexually excited to be serving Caroline in any way she wanted! It made Heather want Gary all the more, her mind now flashing to what life could be like with him. After about 15 minutes of those sorts of activities, Caroline ordered Gary onto the bed, but out of his panties first.
"Lay back, get in the position." Gary spread out his legs and arms and Caroline cuffed them tightly to the bed's posters. Then she also blindfolded him. Caroline then began a favorite of the two. After a bout of deep-throated kissing, she alternated between having Gary suck on her large, ripe breasts and smothering him with them up to a minute at time. Heather observed how Gary's erection never wavered and remained poking into the air the entire time. After satisfying her desires this way, Caroline moved her bottom up to where her pussy pressed against Gary's mouth. "Stick out your tongue, Gary, and get to work. I want a lot of action here now. I want to feel your tongue inside me."
Gary did completely as he was told, bringing Caroline to two orgasms before she climbed off. She did nothing for her slave, however. "Gary, I have a friend here today whom you will now entertain as you entertained me. You will follow her orders as if they were mine. Are we clear?"
"Yes, Mistress," was Gary's answer, but he was not a little bit nervous and it showed by his suddenly weakening cock. Caroline had on a number of occasions over the years forced Gary to satisfy one of her friends from college or even a relative, but those events always began downstairs and stayed there. They had never gone to a bedroom, he was never tied down when they happened, certainly never blindfolded, and Caroline always remained in the room.
Heather emerged from the closet as Caroline left the room, but not before giving the younger woman an encouraging smile. Disguising her voice just enough so as not to give things away right away, Heather said: "You are a lovely young man, Gary. Caroline has said so many nice things about you. I think we are going to enjoy our time together very much."
"Thank you, Ma'am, Gary said, straining to see something through his blindfold but failing.
Heather ran her hands up and down Gary's body, feeling him in a way she had always wanted but couldn't because it would have been far more than a platonic touch. The gentle voice and the caress of her hand relaxed Gary and caused his cock to return to its previously hard state.
She seems nice, he thought.
Finally, the mystery woman climbed onto the bed with Gary and began to kiss him with an intense passion he found surprising for one of Caroline's friends. Usually they showed little interest in that. It also afforded him the first opportunity to smell her and found her scent familiar but unable to pinpoint why. As they kissed, Heather continued to touch, caress, and stroke Gary all over his body, in a way that was so sensual he began to yearn for this woman to fuck him. This surprised him because usually he did not want Caroline's friends to do that and she did not let them. Oral service had been her limit. And that came here as well. Heather desperately needed some relief from the fires burning in her groin and she soon settled her pussy down on Gary's mouth as well. "Lick me, Gary, lick me until I come."
As he did so, Gary could tell this woman was not of Caroline's generation. She's a younger woman, he thought. The thought excited him and worked hard to please her and brought her to two successive orgasms over the next 10 minutes.
After that, thinking that at least she could experience that much but was unwilling to proceed to intercourse until they talked, Heather dropped her voice disguise, her heart pounding, removed the blindfold. "Let's talk."
"Oh My God! HEATHER! What are you doing here?!" Gary strained against his bonds but they didn't give way. Heather did not remove herself from Gary's chest. At the same time, she observed that Gary's erection was rapidly deflating and the blood from that part of the body was moving to his face, which was now quite red from acute embarrassment.
"Calm down, Gary. I said we should talk."
"I don't want to talk; I want you to get the hell out of here!"
Heather thought that this was not a good start but nothing would be gained by letting Gary go. If she did, she'd never get him back. "No!" she said firmly. "Not until we talk about what happened here!"
Gary finally stopped pulling on his restraints, rested his head back on the pillow and looked with angry, watery eyes. "Fine. Go ahead and talk. What the hell are you doing here?!" Gary never felt so mortified in his life. His best friend from college was sitting here, in Caroline's house, in full knowledge of his secret life of all these years. He wanted it to all go away. He wasn't sure if he was more angry with Heather being there, knowing what she now knew, or Caroline who obviously set it all up. He tried hard to simply not cry.
Even angry he is adorable, Heather thought. She hoped this would work out. "Caroline and I talked, Gary---"
"Clearly!"
"Will you just shut up a minute and listen, or I'll take that whip off the wall and make you truly regret it?" Heather said pointed to one of Caroline's more ominous looking implements.
Looking chastened, Gary simply said: "okay."
"While it wasn't her intent to do so, it came out when we were talking, the nature of your relationship with her. But you both already know that it is coming to an end. You're going your separate ways. And, well, let's face it, you need this Gary, you need to be dominated by a woman. Admit it. And I want to be the one who does it."
Gary paused a long time before speaking. "I admit I will be leaving Caroline for good when we graduate. I admit that I want...I need to be dominated. But so what? It's not like we're going to be together in a few weeks either. And your my friend...I thought."
Now it was Heather's turn for her eyes to well up a bit. "I am still your friend, Gary. And we can still be together. The fact is, you stupid idiot, is...is that I love you. I have loved you practically from the day we met. I want to marry you. We could start our careers together and take what life gives us, together. And if you would want to be ordinary husband and wife, I would love that, too. But, frankly, I would love even more if when you came home at night, you fell to your knees, kissed my black boots and served as my love slave. Forever."
Gary stared at Heather with his mouth open and, he discovered, a growing erection. The thought of what Heather just described sounded wonderful! He needed what she was offering. And if he never thought of Heather in romantic terms it was because he was completely absorbed by Caroline. But now, confronted with those thoughts directly and having a choice to make, he realized that perhaps he loved Heather as well. He had always enjoyed her company in everything they did and shared many interests and many values. He had had few sexual thoughts about her because, well, Caroline was focus of all of his sexual energy, and he did not imagine Heather as the dominatrix type. Looking at her, sitting on his chest in black leather was helping to dispel that notion.
Heather continued to say nothing in the long silence but glanced momentarily behind her to see Gary had in the long silence grown fully erect again. She grabbed his cock gently but firmly, and broke the silence: "Is this your answer?" she asked smiling.
The sound of Heather's voice brought Gary's mind back into focus. "I, I guess it is. Maybe that head understands better than the one on my shoulders. I have loved you so long as a friend, I just never thought about you as a girlfriend. I mean, let's face it, with Caroline in the picture, I wasn't ever thinking about finding one. So now what?"
Heather giggled with joy, with waves of relief and happiness flowing through her but not so much as to reveal to Gary just how desperately she wanted him. "Well, it seems a shame to waste this," she said rubbing his cock, "but I would understand if you want to wait a bit before getting so...intimate again."
Gary looked at the door and saw it was still closed and locked from the inside. He smiled at his girlfriend. "I'll leave it up to you. After all, you're going to be the one in charge, right?"
"Ohhh, yes! I'll command and you'll obey. For the rest of your life." Heather then bent down, grabbed a fist-full of Gary's hair and began kissing him with a passion held in for more than a year. Soon Heather slid her groin down over Gary's penis, lingering for a few seconds and then ever so slowly taking him inside her, at a pace Gary couldn't help but find maddening. She eased herself all the way down his shaft until his envelopment was complete. Only then did she release his lips from hers and begin a slow but increasing grinding motion with her pelvis. As Gary opened his eyes when she did, he saw Heather with hers closed, her tongue licking her lips and clearly in an ecstasy greater than sexual pleasure alone. He closed his eyes again to enjoy the ride. Neither young woman and young man, mistress and slave lasted very long. They came together in shouting match of sexual climax loud enough to bring a smile to Caroline Barron's mouth half a house away.
Moving Out, Saying Good-bye
The succeeding two months were rather hard on Caroline. She felt that she and Gary couldn't continue as they had been now that he and Heather were joined at the hips, as it were. Moreover, Gary was still a renter in her house and was therefore entitled to all the rights and privileges tenants have, such as overnight guests. Heather came over frequently and Caroline's home afforded the two more privacy or, arguably, less of a need for privacy than Heather's, which she shared with two other students. Neither of those girls could possibly understand the new, dynamic and very different relationship Heather and Gary were forging.
And truth be told, Caroline didn't mind. It gave her regular opportunities to talk with Heather, usually about Gary, when he wasn't around, and often when he was. Caroline and Heather talked at length about dominating a male, sexually and beyond, the latter still very new to the practice. Gary didn't mind this either, even if it seemed a little embarrassing and objectifying at times. But, like most guys, he didn't mind being objectified either.
Caroline often got to listen, unbeknownst to Heather and Gary, to the young mistress discipline and conquer her young slave. She had discovered long ago the heating ducts in her house provided very easy listening to Doug's room, which Gary rented, and she could almost hear everything if she listened carefully and very quietly. It was in that way she often headed off some of Doug's more stupid ideas when he was growing up and her son had never quite figured out how his mother was always one step ahead of her. So for the last two months Caroline lived vicariously through Heather's and Gary's antics. She knew Christopher would be moving in about a month after Gary left and that seemed very promising indeed, but having been used to dominating a young man virtually daily for six years, it was hard not to partake in the interim.
Finally, Memorial Day weekend rolled around and Gary, with Heather's help, was packing up and moving out. They were headed west to start their careers and lives together. Both had graduated with honors, with Caroline a guest of them both. The parents of the twenty-somethings each commented to their children after having met Caroline what a good influence Gary's landlady must have been on them. If they only had known, Caroline thought.
Heather and Gary carried the last two boxes down from the stairs. "Well, that's all my stuff, Caroline," Gary said. "The furniture of course is yours, so it is all set for your next tenant." The way Gary said that suggested to Caroline that Heather had never told him who the next tenant was going to be or about the "deal." On the other hand, Gary may not want to dwell on it either, in light of their long relationship.
Heather returned from putting her box in the car and then grabbed the one in Gary's hand. She had thought about this for a long time and while she had some misgivings, thought this was the decent thing to do. "Look, I've a got a couple of errands I need to run. It'll take me a couple of hours. Gary, why don't you stay here. You and Caroline could, uh, you know, say a meaningful good-bye." Heather noted that Caroline's face brightened momentarily and then retreated to her cool reserve and Gary looked shocked.
"Really?" he said.
"It'll be. . .---I'm cool with it," Heather replied. "But after today," she grabbed his shirt and pulled him close to her lips and eyes, "I am your world." She then let him go, choosing not to reinforce the point in front of Caroline with a possessive kiss. "Have fun and, Caroline, no permanent damage, okay?"
Caroline smiled, "thank you dear. That was really very sweet of you."
"See you in two hours." Heather left, closing and locking the door behind her.
Caroline wasted not one second. "Strip and get on your knees, with your head down, Gary. I have hated seeing you in clothes in my house these last two months." Gary did so as fast as he could and within one minute was kneeling down with his forehead touching the floor. Caroline took off her shirt and dress, leaving her standing there in a black lace bra and panties and four-inch pumps. "Now crawl over to me, and begin kissing my feet and legs, work your way up to my pussy, and then lower my panties with your teeth and worship me until I come!"
"Yes, Mistress, thank you Mistress." It felt like old times to Gary, as much as he loved Heather and looked forward to their life together as mistress and slave, Gary always felt overwhelmed by Caroline. Her height, her intelligence, her beauty---she was superior to him in every way and he knew it. That innate sense of inferiority he felt before Caroline always made him want to do anything she desired. The past two months, apparently, had not changed that at all.
Gary kissed Caroline's feet, flicking her ankles with his tongue. Slowly he worked his mouth up each of her legs, finally nuzzling her crotch with his face, a spot that made him feel very at home and a sensation at which he was certain Caroline shuddered. As he began to work Caroline's black panties down just enough to give him access to her pussy, his eyes widened at the sight. Caroline's bush had more hair than he was used to seeing, clearly she had stopped trimming it when Heather entered the picture, but it was beautiful and full, and smelled of perfume mixed with feminine excitement. His hands stroked Caroline's legs, running them slowly up and down, feeling the strength and glory as they seemed to go on forever.
His tongue began to probe through the forest and when it found her labia, he slowly licked up and down. Caroline had missed Gary's touch so much; she gave in to the temptation to push him along once his tongue met her sex. Shortly after the licking began, Caroline grabbed Gary's head and started to control the pace of the action. She forced his face into his pussy while at the same time rubbing herself up and down as Gary struggled to breathe. Gary by this point had grabbed hold of Caroline's buttocks with his hands, in part to steady himself against Caroline's increasing control of his movements. Soon he could feel and hear Caroline come in repeated shudders accompanied by loud groans of ecstasy.
"Don't stop, Gary. Again," Caroline commanded and while she no longer was forcing Gary into her, she did not remove her hands from his head, waiting rather to see her former slave begin on his own where she had left off. Gary took the opportunity to press Caroline against his face, as he stretched out his tongue, entering her vagina with it as far as he could with a swirling motion he learned long ago Caroline loved.
"Oh god, Gary! Deeper! Push in deeper!" Caroline moaned over and over until she felt herself coming again, and she cried out more screams of delight.
Finally she released Gary's head and he sat backward on his haunches, his face glistening with the juices from Caroline's pussy. Pulling up her panties, Caroline declared grinning, "I've missed that! But let's go. Crawl upstairs. I have an hour and forty minutes. I intend to use every one of them." Caroline followed him as he climbed the stairs on his hands and knees, punctuating his movements periodically with the occasional smack on his rear. Once Gary was in the room, Caroline ordered him to lie down on the bed on his stomach with his feet on the floor. Caroline meanwhile put on a pair of soft leather, thigh high but low-heel boots. She wanted to wear them the rest of their time together and sometimes heels get on the way of certain activities. She put on opera-length leather gloves and then strapped on a rather substantial looking dildo. Gary has come a long way since his first time, Caroline thought as she admired her look in the mirror.
She then dipped the phallus in lube and walked over to her prostrate slave. She then twisted both of Gary's arms behind his back as she rested the tip of the dildo on his anus, between his checks. Gary could feel the cold hard object violating him even as his erection grew harder. "You loved being my bitch, didn't you Gary?" Caroline whispered.
"Yes, Mistress."
"Then let's make this one to remember, shall we? Say it!"
"I'm Caroline's bitch!"
"Louder!"
"I'M CAROLINE'S BITCH!!" And with that, Caroline plunged her phallus into Gary's ass and worked the tempo faster, yet still painfully twisting Gary's arms all the while listening to him yell over and over that he was Caroline's bitch. Finally it was all too much and Gary screamed out, coming on the sheets as the abrasion against his cock and prostrate was too much.
After such an intense start, Caroline took it more sensuously for the next hour, allowing Gary his old habits of brushing her hair doing her nails, worshiping her breasts for what seemed like an eternity. By the end of all that, Gary's erection had returned and she wanted to end on a particularly intense note. Using much of her bondage gear, Caroline trussed Gary to the bed to the point of near immobility with leather straps, cuffs and mitts criss-crossing every part of his body, topped off with a bondage hood and gag that left only two small holes through which Gary could breathe. Caroline then sat down on the bed, stroking, lovingly, every exposed inch of her soon-to-be-ex-boarder’s skin, including painfully working the nipples. She sat there, touching and relishing the moment, the complete control she had over this young man. And when she knew it was nearing the end, she mounted Gary's penis, fucking him to one final tremendous climax, which was quite loud even through the hood and gag.
When they were done, Caroline released Gary from her bondage for the last time. "Stand up, Gary," Caroline ordered, but not at all unkindly. She pull him into her, standing eight inches taller in her usual high-heeled boots, bending his head back and gave him a long deep passionate kiss. With tears in her eyes, "these past six years have been some of the best in my life. Thank you."
"Oh, Caroline." It was Gary's turn to turn teary-eyed now. "It was a wonderful, wonderful ride and I wouldn't have traded it for anything. I love Heather, but know that there is a part of me that truly wishes this were not coming to an end and I could stay here forever."
For a long time, both former mistress and former slave said nothing and continued their embrace and gentle caressing. Finally, it was Caroline who broke the silence. "You must shower now. Heather will be back soon."
"Yeah." And Gary left for the bathroom.
Caroline put on some more appropriate clothes and went downstairs to wait for Heather and Gary both. Soon enough Heather pulled up and came in. "Hi," she said a little uncertainly.
"Gary's in the shower. He'll be down shortly," Caroline replied. After a longish pause, Caroline added: "You have a wonderful young man there. I'll admit to you that I will miss him very much."
"I know. I have known that since the day I met him."
"Of course."
After another long pause, Caroline spoke again. "That said, if you ever need any advice or suggestions on how to break him to your will, I'm just a phone call away!"
Both women just laughed.
"What's so funny?" Gary had come down the stairs at that moment. Both women laughed again at his exquisite timing.
"Nothing. Nothing you have to worry your pretty little head about," Heather answered. "Well, I guess were all set to go?"
"Yeah, you have everything in the car. I guess this is good-bye, Caroline."
She gave them both one final hug and said, "do keep in touch. I look forward to hearing from you both about everything."
And with that, Heather and Gary went out the door, followed by Caroline, got into the car (Heather got behind the well) and drove off.
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