2 comments/ 79358 views/ 18 favorites M.I.L.F. vs Stud Ch. 01 By: mrsmillwood This is a continuation of "M.I.L.F. Takes Charge", available in my profile. * Much has transpired since I wrote about my encounter with the young buck who would make me his conquest, while I wished to make him my obedient submissive. Most of what happened, and certainly the most exciting, has transpired over this past summer. I will write a short prologue to this story to bridge the gap between the first encounter and the events of the past summer. I left you, as you will recall, with Derrick suggesting that I become his body building bitch and suck his balls dry every night. I admit, that was a tempting offer. If you saw what it was he had to offer from between his strong thighs, you would not blame me for kneeling before him, wearing his collar. I fell asleep to that thought. I awoke when Derrick was walking back to bed, presumably from just having gone to the bathroom. His long cock bounced from thigh to thigh as he walked through the early morning light that filtered through the curtains. I dozed off for probably an hour, then woke to find Derrick asleep beside me, barely covered with the bedsheet. I saw the bulge of his morning erection resting on his lower stomach. I carefully peeled the bedsheet back to reveal his impressive manhood. I thought seriously about taking it into my mouth and having my way with it until his fresh seed filled my mouth. But then I heard my daughter walking down the hallway to the bathroom. That's when I realized that the consequences of my actions would affect more than myself. By allowing myself to be collared, I am affecting Katye's future as well. Most assuredly, Derrick would have Katye collared and serving his sexual desires as well. I did not raise my children to submit so willingly to a male. I raised both my son and daughter to understand that women were every bit as strong, if not stronger, than males and should stand their ground against them. For Katye's sake, as well as Kyle's, it was important that I not succumb to Derrick's lust; rather I needed to dominate him and collar him to illustrate to my family exactly where a male's place is. As quietly as I could, I rummaged through my closet to locate some necessary accessories. Fortunately, Derrick was a deep sleeper, or perhaps just exhausted from the events of the previous day. Either way, I attached ankle and wrist cuffs to the bedposts, while also attaching a leather collar to the headboard by a one foot long chain. I quickly moved to secure his left, then right ankles to the cuffs. By this time Derrick awoke, but he was too bewildered to resist. By the time he was able to properly assess the situation, I had the leather collar locked tightly around his neck. The boy was far too strong for me to wrestle his arms into place, so it would come down to a test of wills. Unable to sit up to uncuff his ankles, he began work on the collar, while protesting verbally. He didn't quite know if he should be scared, angry, or excited. I think he was all of the above. I nonchalantly sat on the edge of the bed and reached between his spread legs and cupped his ball sac. "You know, a woman can know everything a male is thinking just by observing what is going on down here between his legs. Your cock has begun to shrink a bit and your balls are tight to your body," I noted as I encircled his balls with my thumb and forefinger, pulling them down from his body. "A tight set of balls means that you are either about to cum, you're cold, or you're very scared. I think you are very scared about right now. "Oh Derrick, I'm just having some fun with you. Relax! Listen, I want to lock you up and let you think about how much you could learn if you are willing to submit to me. I can't force you. I can't keep you tied up forever. But I would like to keep you locked to the bed for a few hours, just to give you a taste of what life might be like if you take me up on my offer to be my boy bitch. Why don't you just go ahead and lock the cuff around your right wrist. I'll take care of the left. We'll have a little fun, think about things, and I'll let you go in time for lunch." He looked me in the eye, his cock twitched, and he reached over and locked the cuff around his wrist. By the time I cuffed his left wrist, his cock was as hard as I had seen it. While I was in the shower, Katye knocked on my bedroom door, which was slightly ajar. Hearing no reply, she pushed the door open and peered around the side. "Oh my gawd!" She wasn't expecting to see her friend tied spread eagle to my bed. "Oh Derrick...all right, wow. Sorry, I didn't mean to intrude. Ummm, I'll just wait for my mom to come out. No rush." Evidently, she couldn't resist the temptation. Before I was out of the shower, she let herself back in the room and sat down on the bed next to my prisoner. Without embarrassment, she lightly tickled his ball sac, giggling at him. Then she took hold of his shaft, pulling it straight up. "Damn, that's one hard rod. Oh, look at your balls; they're getting all tight! Don't be scared." She patted him on his inner thigh and left the room. I think that probably cemented his decision. I walked back into the bedroom, still drying my hair with my towel. He didn't need to see my naked body, dripping wet, in order to be excited. He was as hard as I had left him. Dripping hard by now. Over the next four hours, I made my way back in to check on my new toy. Only once was his cock not as hard as I would have liked. Each visit, I took about 10 minutes to stroke his cock, massage his balls, and lightly run my fingernails over his smooth chest. And each time, his ample precum dripped down his long thick cock and beads of perspiration dotted his body. I tormented him to the point that he fought against his bonds and begged for relief, which of course, never came. Then, I allowed him to put that pent up frustration to good use. I straddled his head and slowly lowered my wet pussy lips to within an inch of his mouth. I let his instincts take over. He strained against his collar to lick. I teased of course, but relented eventually. I let him suckle my clit. His eager tongue first licked, then sucked, then upon my orders, dove deep inside my pussy as I sat hard against his face. I smothered him with my sex, and nearly drowned him with my orgasm. Once I regained my composure, I sat up, leaving his face covered with my offering, and him gasping for air. Finally, in the early afternoon, I decided he had had enough. "Derrick, I'm going to release you. You can either let me attach this ball stretcher around balls, then put this on," I said, holding up his skimpy white Speedo, "and have lunch with Katye and myself out by the pool, or you can masturbate in front of me to relieve your pent up frustration and never see me again. I'll leave that up to you." I thought I knew what he would do, but I wasn't sure. He stood, his cock throbbed hard against his belly, but he took the Speedo from me. He looked down at his member which looked back up at him, drooling. He took a deep breath, and with an ever-so-slight look of humiliation, nodded. It took me only a minute to lock the ball stretcher in place before he slipped his Speedo on, and tucked his rigid tool over to the side, barely covering it behind the Speedo. I surveyed his massive display of manhood, and walked with him down to the kitchen. Katye couldn't contain her pleasure at what she saw approaching. She ran her hands over his chest, his perfectly round ass, then of course, over his bulge, barely contained in the stretched fabric. After an afternoon of tanning, it was time for Derrick to leave. "Derrick, I have but one more test. I'm going to remove the ball stretcher, and replace it with a chastity device. If you want to see me again next weekend, you will wear this. It is possible to take it off if you really try, but it will be impossible to put it back on without breaking the lock. I hope you will wear it, and learn from it. You will be surprised at what this will do to your state of mind, and any thoughts of dominance that might still be fluttering around in that pretty little head of yours." "Each weekend that you spend with me, I'll remove it, but I demand that you replace it before you leave for the week. You'll wear it until you are either broken, or you decide that this just isn't for you. Okay?" Again, he just nodded and stood stoically as I removed one piece of hardware to attach another. The problem was that he never lost his erection. And by the time I had the stretcher off, his cock was throbbing, begging for just a stroke. "There's only one solution for this, Derrick. You'll have to believe me when I say this is the best thing for you." I retrieved just the right paddle from my closet and told him to hold his cock straight out. Without hesitation, I administered two quick swats to his over sensitive cockhead. He let out a loud scream that only a male could make when his sexual organ is assaulted, but before the sting had left his cock, it was wilting into submission. I gave him one more good swat for good measure, and had the CB3000 on before he had a chance to recover his hardon. It's amazing what happens to a male's brain when he is denied the ability to become erect or even feel his cock -- for five days. Like an obedient pet, Derrick was on my doorstep at 6 PM on Friday. I fucked his ass several times; I teased him, and I used him. I had never felt such an eager tongue lapping at my pussy as his was. He plunged it deep inside me, nibbled at my clit, sucked me, then drank my juice as I came on his face, leaving him between my thighs to lick my pussy lips as I faded to sleep. I did allow him an orgasm, but I can assure you, it was far from fulfilling. I took him just to the edge then stopped and watched as his cock churned out an impressive puddle of white cum. Each week was much like that one. Some better than others. But with each week, Derrick fell further and further into submission. Now, I will explain what has happened over this last summer, 2009. It has been very exciting, more than I ever thought possible. While I am quite capable of training a male, I received invaluable advice and support from a very dear friend. This friend recognized potential in me and knew that with a little guidance, I could be so much more. He mentored me and truly made me blossom into more than a mistress. With his loving mentoring, I have become a true Lady. Our relationship started out friendly and polite enough, but has developed into something much greater. We have made a special connection that I wouldn't have thought possible thru email, yet we each feel strongly for one another. Please read our correspondence, and enjoy. Truthfully, I have edited it to protect our privacy, but the message remains intact. [Please let me know if you like the email format of this chapter. I have five or six more to post, so if many of you do not like the format or find much of our exchange to be irrelevant, then I will make changes for the proceeding chapters.] July 3: Well now, Mrs Millwood darling, what can I say? Your story is fantastic and made me so horny. I am an author, and something of a master. I shall think about your story and see where I can take it. I find the attraction you describe as incredibly erotic and it offers some interesting sequels. I would love to hear from you, you sound like a very sexy woman. Love M Hello M, I am so glad you enjoyed my scenario. I have had several people compliment the story, but you are the first to promise to continue it. I am looking forward to seeing where you take it. As for the names of my friends, I will give you a few. My dearest friend, well I suppose I have 2, but one is Heidi. She is going to be taking in my son, Kyle. As a side note, Kyle was supposed to be away this summer visiting his father, and that's where he is now, but by August he will be back. I don't want him living here with me and Katye because Derrick has moved in with us, so I plan to have Kyle live with Heidi upon his return. She'll be great for Kyle. She's a very loving woman who will teach him well without being over bearing or stern. My other dearest friend is Maize. She is as off the wall as they come. We tell her it's her Catholic school upbringing. She's the life of the party. She wanted Kyle to stay with her. Any if Kyle weren't my boy, I'd be all about it, but he is my boy, and as a mother, I can't mentally deal with the thought of Kyle being under her control. Oh lord, the things she would do! I have 2 other girlfriends who comprise our group, but I'll leave their names/personalities to you, if you choose to write them in. One of them has a boy and girl, both good athletes in their teenage years. I hope you will post your version of the story on Literotica. I posted a thread about this story with a link on the Story Ideas forum of the Bulletin Board, titled "MILF tries to turn tables on young stud." I hope you post your story on Literotica and add a thread to my original post on the forum, so others will know of it. I have received several emails expressing interest, but you are the only one who has promised to continue the story. If you do not post it on Lit, please send it to me at this email address. I will be posting my version in October, after this summer of adventure is over. You are a Master? Do you have anyone collared right now? As a Dom, I have to ask, do you find it offensive that a dominant woman would take charge of a young male? I have always wanted to ask this question of a Dom, but haven't had the opportunity until now. Thank you for your kind words. I look forward to hearing from you and where you take the story. Mrs. Millwood July 4: Thanks Mrs Tina Millwood, I have a plan in my head for you and I`ll get back to you very soon. I have a lot to say about you, a female Dom (Domna) controlling a male ---- You will like what I have to say but the critic who was very rude would hate me! I have a few suggestions for you also!!! Warmest wishes and keep them all under your thumb!! Lord M M.I.L.F. vs Stud Ch. 02 July 10: Lord M, I am intrigued. I look forward to your thoughts, although, I'm not sure Derrick will! "Under my thumb", Derrick is...at least the vital part of him is. ;) I'm not sure what the critic expected. It was under the BDSM category.. Mrs. Millwood * My Dear Mrs Millwood, I must say I was delighted to see your name in my inbox this morning. Well may you be intrigued for I have many questions to ask and many suggestions to make. I suspect the sub Derek will be saddened at first. However, I do assure you, Mrs Millwood, that if you follow my suggestions Derek will grow to love his role as your sub, perhaps your Alpha sub, and you will experience what it truly is to be a good Domna. In the story Derek was most insistent on fucking you first and you had to use some persuasion to keep the correct line. I would see this as a serious misdemeanour. It is not a serious offense that would require extended punishment. It is, however, sufficiently grave to warrant physical discipline, at the very least 'over the knee -- bear ass -- SPANKING' from his Mistress, Mrs Millwood. I would like to hear your views on this Dear Lady. As for that crank who criticized your story he deserves to be both caned and lashed, something I rarely advocate. Mostly my hand on buttocks, male of female, is quite sufficient. Men always get erections and women gush cunt juice. This man however is too arrogant for his own good. You, Mrs Millwood, are equal to any male Dom. I am sure you see now that I believe in equality between men and women. I would be most happy, however, to be your mentor in such matters, especially with respect to young Derek. Another area I ask about is you daughter and where she fits into the role. I do see immense and very erotic possibilities in many directions. However, my Dear Lady, she is your daughter and my respect for you is immense. For this reason the story I write will reflect that respect. If, On the other hand, you give me permission to write as I see fit, I will happily do so, I see her as either a trainee domna or as a sub. With respect to my story, I have decided NOT to post it on Literotica but to give it to you as a gift, my special friend. Once written I shall send it to you as an attachment and you may use it in any way you like. I look forward to your answers to my questions, especially about spanking and about your daughter. Meanwhile I remain very affectionately, your friend. Lord M * July 14: My Dear Mrs Millwood, I realized today that I have said very little to you about me and my sexual preferences and practices. I am very much a man, a heterosexual man and I love women. I am now retired, so I do not have anyone collared. Mostly I fuck my wife hard and long. The only sexual service a male slave or sub is permitted to give me is to suck me off. I have had several slaves collared, Mostly women of all ages from about 20 to late middle age. Now My preference is for older women. They are less inhibited than most young women and cum so nicely. I have had one male slave, he was amazingly submissive and contacted me at a time my wife and I ran swingers cruises on the harbour. He worked naked as a servant to everyone on board, doing whatever they wanted. He had a very long, even though slightly thin, cock. He loved to wank in front of everyone. Another slave at the time was a woman of about 30, she had the smallest tits I have seen but her nipples were electric! We used to shower together at the end of a session and she would wash every inch of me -- literally -- and swallow my cum. If that male slave behaved badly, or touched his cock without my permission the woman slave would spank him until he would cum. If he did not cum with spanking I would spank him and then the woman slave. Now, my relationship with slaves and subs is more as an advisor to their master / mistress. I occasionally apply discipline f the master / mistress thinks it advisable. One young woman, in her mid 20s would come as soon as I spoke to her. He master was very in love with her and saw her as his soul mate. This may have been why he could never discipline her adequately. I used to enjoy spanking her and fucking her in front of her master. He would wank as he watched and then fuck her. I have two young women, one in her early 20s and the other in her mid thirties, both wanting me to collar them. They are both gorgeous with great bodies and kissable lips -- I love to kiss deeply for a long time. The biggest turn on for me is to make a woman cum, by any means, and for her to keep cumming several times in a long string. Once I hear back from you about you lovely daughter I shall write the story for you. Have fun with your slave, dear lady. Affectionately yours Lord M * Hello Lord M, Thank you so much for filling me in on the details of your life. I am glad to learn more about you. I find your history to be very interesting. You certainly didn't lead a dull life! I very much appreciate a person, Man or Woman, who knows what they want, and takes charge to get it. I think you have done that. I am sure your slaves have appreciated your confidence and sure hand, as well. I am sorry for taking so long to reply to you. I was logging in now to write to you when I saw this email. I took a long weekend and am only now responding to things I should have taken care of last week. I do not want you to feel that I don't appreciate our correspondence. I very much do. I hope to use Derrick much the same way you used your male slave. I want Derrick to grow from a sub into slave so that he will perform in any capacity that I wish, without hesitation or reservation. How old was your slave boy? I am impressed with your ability to make a girl cum, just by speaking to her. Quite a voice you have, Sir. A little bit about my daughter, Katye. I raised her to be a strong girl, certainly an equal to her male classmates. In our household, she and her brother had to perform chores around the house, but I made sure her tasks were not specifically the 'woman's work.' Kyle cleaned the kitchen as often as Katye. I made sure Katye stood up for herself and understood that success was hers for the taking. She has leadership potential, however, I have always hoped that she would take life by the balls, but so far, hasn't. Like many of her friends, she seems to be in the punk phase. Black hair, interesting choices of fingernail polish, and all of the other accouterments. Her leather would fit right in to the domme stereotype. That said, I had no idea if she would be sexually dominant. The summer is young, but she has taken to having Derrick with us as a submissive. She was very accepting of the idea of Derrick serving us domestically, and me physically. Katye thought it was a great idea. I think she has come to see the advantages of having a male submissive around the house. So far, she hasn't asked to use him for herself, and I'm glad as I don't like the idea of sexually using the same boy as my daughter, but I think she's formulating some plans of her own. Katye no longer treats Derrick as her old friend, but as an inferior, someone who is there to wait on her. It's interesting that she no longer talks to him as an equal anymore, ignoring the time they spent together growing up. I like to think that she looks upon him as something less than herself, a mere sexual object. I oftentimes wonder if I did something to cause Kyle to be so submissive. I always expected him to be respectful of his sister, and other girls, for that matter. But I don't think I did anything deliberately to turn him submissive, however, that is exactly what he is. I say that proudly, as I do not see it as weak for a male to have a submissive heart. I just find it interesting that my daughter has a very strong personality, while my son is strong physically, but submissive in spirit. Concerning your story, Lord M, I would have to say that I do not relish the idea of sharing a sexual experience with my daughter. I can easily see a scenerio in which I allow her to use Derrick for her personal pleasure, but not at the same time as me. I certainly do not see her and I pleasing each other sexually. That said, I will respect your imagination, as I have opened it up for a wide interpretation. I will follow this up with another email in response to your ideas for disciplining Derrick. With warmest regards, Sir, Mrs. Millwood * July 15: My Dearest Mrs Millwood, Thank you very much, dear lady, for your emails. You have certainly not rambled on too much. On the contrary I have received much pleasure reading your letters. As for enjoying my two girls, I certainly shall -- and I shall think of you as I do so! In fact, my dear Mrs Millwood I do believe I would enjoy an interlude or two with your good self! Distance however is too great at this time. That said, please allow me to offer my sincere congratulations on your amazing progress with your sub -- soon to be slave -- Derek. Your discussions with Derek on discipline are most pleasing. There are some points where I would like to make some adjustments, especially early in his training. Your plans, however, are exceptionally fine. Well done dear lady! Thank you for your words on both Katye and Kyle. I am taking them on board and I promise to give careful consideration. If you wish to really progress in your lifestyle you will need to stretch you expectations and boundaries, but there is no hurry and certainly there must never be pressure that YOU do not want! I shall always respect you, my dear. What is absolutely clear is that your delightful, albeit 'punk for now' daughter is definitely a sexual dominatrix! I shall give serious thought to this because she has a wonderful opportunity right now with her equally delightful mother. I shall not push you where you do not want to go. I shall however encourage and guide, in a loving way, so that both you and your loved ones -- all of them - gain as much as possible. The important thing to remember is to always have respect in every direction in sub -- dom relationships. Your decisions must be guided by love as well as seeking pleasure or punishment. On the topic of punishment. The fact that Derek asks NOT to be spanked. I believe that at times you must do so. Perhaps a cupped hand (much less painful -- quite sensual in fact) as an introduction. I also suggest you get your daughter involved in applying this. Now I have rambled on a bit. Give my best wishes to your daughter, dear, Mrs Millwood, and continue the firm hand on that boy! With much respect and deep affection, and not without attraction Yours Lord M PS: feel free to address me as 'My Lord" or 'Your Lordship' as is appropriate and the mood takes you. Your Lord mentor and friend XXX * July 20: Hello Lord M, How have you been? I look forward to hearing about this trilogy of yours. I'm intrigued. As for the handling of my sub, Derrick, I think I will be using my hand on his bare ass tonight. We had a disappointing weekend, but not one that was unexpected. I would also like to get your feedback on this, My Lord. Friday evening, my girlfriends were over, and I had Derrick serving us drinks in his speedo. He hadn't had an orgasm in about a week, and he was complaining of blue balls, so I thought it would be nice if he were to masturbate for our viewing pleasure. I had him on his knees naked, leaning backward, his back arched so that his upper body was supported by his elbow. His other arm was busy working his shaft. It was so nice watching his bound balls bob up and down in rhythm to the motion of his hand. Finally, we allowed him to cum, and cum he did. He ejaculated all over his chest and stomach. It was such a beautiful site, Lord M! Well, after he cleaned himself up, he continued to serve us naked throughout the evening. It was apparent to me that he was no longer 'in the mood,' so to speak. He never came close to getting hard again, and he didn't have that submissive spirit that we have all enjoyed. Don't get me wrong, he did as he was told, but his heart wasn't in it. Then next morning, we talked, and he admitted to slipping into a 'vanilla mood' right after cumming. I know it happens, but he needs to be able to overcome that. I decided to give him the weekend off to go play with his friends and clear his mind. He stayed overnight at his friend's house Saturday, and was back Sunday night. I only asked that he wear a cock ring around his cock and balls, and wear his leather necklace that I bought for him. It's the'collar' I have him wear when we are out in public. It's merely a thin leather strand with a small ring on it. I have him wear that tight to his throat. Anyway, this was the 3rd time he has gone vanilla on me in the last 7 weeks, and it's always after he's allowed a very fulfilling orgasm. I have decided to severely limit his emissions. I will only allow him to cum once every 3 weeks, at most. And when he does cum, I will not allow him a fulfilling orgasm. I will stroke him for the foreseeable future, and I will be sure to stop stroking just after he climaxes, thus giving him some relief, but not as enjoyable as he would like. This should have him back 'in heat' very quickly. I also think he's simply going to have to deal with his blue balls. That's simply a consequence of being a male. Tonight, I am going to have Katye work his balls over. She seems to have taken to inflicting pain upon his testicles. It's amazing how a drumstick tapped lightly against testicles for about 30 minutes, will drive a boy nuts with pain. Such little effort, yet so much agony! Then I plan to keep him in his chastity device as punishment, stripping him of his ability to even feel his cock. 3-4 days of that will have him thinking straight, I do believe. All in all, we have learned from this episode. A slave needs to be kept 'in heat' in order for a domma to reap full benefits and rewards. As I said, a spanking will accompany his testicular punishment. A good red ass will drive the point home well. Any other suggestions, Lord M? With warmest regards, Your Lordship, Mrs. Millwood * My Dear Mrs Millwood, I simply must send a brief reply immediately. Your description of your handling your slave boy is magnificent. I am proud of you my dear lady. I am also proud of your daughter, the novice Katye. I am delighted that you have taken to spanking. I do believe this must be severe and perhaps the young novice, your delightful Katye, should warm his ass in readiness for your noble hand spanking! His blue balls is a consequence of being collared. If he complains -- keep up the spanking. Your writing is wonderful and I find both the writing and indeed thinking of you to be very very erotic. Fortunately for me I do not need to suffer blue balls!!!! I shall write properly very soon and tell you all about my trilogy. Meanwhile you and Kayte work closely together. The more exposed flesh with the two of you together in front of the slave while he is denied pleasure the better With deep and sincere affection my dear lady and novice, Lord M M.I.L.F. vs Stud Ch. 03 July 14: My Dear Mrs Millwood, I realized today that I have said very little to you about me and my sexual preferences and practices. I am very much a man, a heterosexual man and I love women. I am now retired, so I do not have anyone collared. Mostly I fuck my wife hard and long. The only sexual service a male slave or sub is permitted to give me is to suck me off. I have had several slaves collared, Mostly women of all ages from about 20 to late middle age. Now My preference is for older women. They are less inhibited than most young women and cum so nicely. I have had one male slave, he was amazingly submissive and contacted me at a time my wife and I ran swingers cruises on the harbour. He worked naked as a servant to everyone on board, doing whatever they wanted. He had a very long, even though slightly thin, cock. He loved to wank in front of everyone. Another slave at the time was a woman of about 30, she had the smallest tits I have seen but her nipples were electric! We used to shower together at the end of a session and she would wash every inch of me -- literally -- and swallow my cum. If that male slave behaved badly, or touched his cock without my permission the woman slave would spank him until he would cum. If he did not cum with spanking I would spank him and then the woman slave. Now, my relationship with slaves and subs is more as an advisor to their master / mistress. I occasionally apply discipline f the master / mistress thinks it advisable. One young woman, in her mid 20s would come as soon as I spoke to her. He master was very in love with her and saw her as his soul mate. This may have been why he could never discipline her adequately. I used to enjoy spanking her and fucking her in front of her master. He would wank as he watched and then fuck her. I have two young women, one in her early 20s and the other in her mid thirties, both wanting me to collar them. They are both gorgeous with great bodies and kissable lips -- I love to kiss deeply for a long time. The biggest turn on for me is to make a woman cum, by any means, and for her to keep cumming several times in a long string. Once I hear back from you about you lovely daughter I shall write the story for you. Have fun with your slave, dear lady. Affectionately yours Lord M Hello Lord M, Thank you so much for filling me in on the details of your life. I am glad to learn more about you. I find your history to be very interesting. You certainly didn't lead a dull life! I very much appreciate a person, Man or Woman, who knows what they want, and takes charge to get it. I think you have done that. I am sure your slaves have appreciated your confidence and sure hand, as well. I am sorry for taking so long to reply to you. I was logging in now to write to you when I saw this email. I took a long weekend and am only now responding to things I should have taken care of last week. I do not want you to feel that I don't appreciate our correspondence. I very much do. I hope to use Derrick much the same way you used your male slave. I want Derrick to grow from a sub into slave so that he will perform in any capacity that I wish, without hesitation or reservation. How old was your slave boy? I am impressed with your ability to make a girl cum, just by speaking to her. Quite a voice you have, Sir. A little bit about my daughter, Katye. I raised her to be a strong girl, certainly an equal to her male classmates. In our household, she and her brother had to perform chores around the house, but I made sure her tasks were not specifically the 'woman's work.' Kyle cleaned the kitchen as often as Katye. I made sure Katye stood up for herself and understood that success was hers for the taking. She has leadership potential, however, I have always hoped that she would take life by the balls, but so far, hasn't. Like many of her friends, she seems to be in the punk phase. Black hair, interesting choices of fingernail polish, and all of the other accouterments. Her leather would fit right in to the domme stereotype. That said, I had no idea if she would be sexually dominant. The summer is young, but she has taken to having Derrick with us as a submissive. She was very accepting of the idea of Derrick serving us domestically, and me physically. Katye thought it was a great idea. I think she has come to see the advantages of having a male submissive around the house. So far, she hasn't asked to use him for herself, and I'm glad as I don't like the idea of sexually using the same boy as my daughter, but I think she's formulating some plans of her own. Katye no longer treats Derrick as her old friend, but as an inferior, someone who is there to wait on her. It's interesting that she no longer talks to him as an equal anymore, ignoring the time they spent together growing up. I like to think that she looks upon him as something less than herself, a mere sexual object. I oftentimes wonder if I did something to cause Kyle to be so submissive. I always expected him to be respectful of his sister, and other girls, for that matter. But I don't think I did anything deliberately to turn him submissive, however, that is exactly what he is. I say that proudly, as I do not see it as weak for a male to have a submissive heart. I just find it interesting that my daughter has a very strong personality, while my son is strong physically, but submissive in spirit. Concerning your story, Lord M, I would have to say that I do not relish the idea of sharing a sexual experience with my daughter. I can easily see a scenerio in which I allow her to use Derrick for her personal pleasure, but not at the same time as me. I certainly do not see her and I pleasing each other sexually. That said, I will respect your imagination, as I have opened it up for a wide interpretation. I will follow this up with another email in response to your ideas for disciplining Derrick. With warmest regards, Sir, Mrs. Millwood July 15: My Dearest Mrs Millwood, Thank you very much, dear lady, for your emails. You have certainly not rambled on too much. On the contrary I have received much pleasure reading your letters. As for enjoying my two girls, I certainly shall -- and I shall think of you as I do so! In fact, my dear Mrs Millwood I do believe I would enjoy an interlude or two with your good self! Distance however is too great at this time. That said, please allow me to offer my sincere congratulations on your amazing progress with your sub -- soon to be slave -- Derek. Your discussions with Derek on discipline are most pleasing. There are some points where I would like to make some adjustments, especially early in his training. Your plans, however, are exceptionally fine. Well done dear lady! Thank you for your words on both Katye and Kyle. I am taking them on board and I promise to give careful consideration. If you wish to really progress in your lifestyle you will need to stretch you expectations and boundaries, but there is no hurry and certainly there must never be pressure that YOU do not want! I shall always respect you, my dear. What is absolutely clear is that your delightful, albeit 'punk for now' daughter is definitely a sexual dominatrix! I shall give serious thought to this because she has a wonderful opportunity right now with her equally delightful mother. I shall not push you where you do not want to go. I shall however encourage and guide, in a loving way, so that both you and your loved ones -- all of them - gain as much as possible. The important thing to remember is to always have respect in every direction in sub -- dom relationships. Your decisions must be guided by love as well as seeking pleasure or punishment. On the topic of punishment. The fact that Derek asks NOT to be spanked. I believe that at times you must do so. Perhaps a cupped hand (much less painful -- quite sensual in fact) as an introduction. I also suggest you get your daughter involved in applying this. Now I have rambled on a bit. Give my best wishes to your daughter, dear, Mrs Millwood, and continue the firm hand on that boy! With much respect and deep affection, and not without attraction Yours Lord M PS: feel free to address me as 'My Lord" or 'Your Lordship' as is appropriate and the mood takes you. Your Lord mentor and friend XXX July 20: Hello Lord M, How have you been? I look forward to hearing about this trilogy of yours. I'm intrigued. As for the handling of my sub, Derrick, I think I will be using my hand on his bare ass tonight. We had a disappointing weekend, but not one that was unexpected. I would also like to get your feedback on this, My Lord. Friday evening, my girlfriends were over, and I had Derrick serving us drinks in his speedo. He hadn't had an orgasm in about a week, and he was complaining of blue balls, so I thought it would be nice if he were to masturbate for our viewing pleasure. I had him on his knees naked, leaning backward, his back arched so that his upper body was supported by his elbow. His other arm was busy working his shaft. It was so nice watching his bound balls bob up and down in rhythm to the motion of his hand. Finally, we allowed him to cum, and cum he did. He ejaculated all over his chest and stomach. It was such a beautiful site, Lord M! Well, after he cleaned himself up, he continued to serve us naked throughout the evening. It was apparent to me that he was no longer 'in the mood,' so to speak. He never came close to getting hard again, and he didn't have that submissive spirit that we have all enjoyed. Don't get me wrong, he did as he was told, but his heart wasn't in it. Then next morning, we talked, and he admitted to slipping into a 'vanilla mood' right after cumming. I know it happens, but he needs to be able to overcome that. I decided to give him the weekend off to go play with his friends and clear his mind. He stayed overnight at his friend's house Saturday, and was back Sunday night. I only asked that he wear a cock ring around his cock and balls, and wear his leather necklace that I bought for him. It's the'collar' I have him wear when we are out in public. It's merely a thin leather strand with a small ring on it. I have him wear that tight to his throat. Anyway, this was the 3rd time he has gone vanilla on me in the last 7 weeks, and it's always after he's allowed a very fulfilling orgasm. I have decided to severely limit his emissions. I will only allow him to cum once every 3 weeks, at most. And when he does cum, I will not allow him a fulfilling orgasm. I will stroke him for the foreseeable future, and I will be sure to stop stroking just after he climaxes, thus giving him some relief, but not as enjoyable as he would like. This should have him back 'in heat' very quickly. I also think he's simply going to have to deal with his blue balls. That's simply a consequence of being a male. Tonight, I am going to have Katye work his balls over. She seems to have taken to inflicting pain upon his testicles. It's amazing how a drumstick tapped lightly against testicles for about 30 minutes, will drive a boy nuts with pain. Such little effort, yet so much agony! Then I plan to keep him in his chastity device as punishment, stripping him of his ability to even feel his cock. 3-4 days of that will have him thinking straight, I do believe. All in all, we have learned from this episode. A slave needs to be kept 'in heat' in order for a domma to reap full benefits and rewards. As I said, a spanking will accompany his testicular punishment. A good red ass will drive the point home well. Any other suggestions, Lord M? With warmest regards, Your Lordship, Mrs. Millwood My Dear Mrs Millwood, I simply must send a brief reply immediately. Your description of your handling your slave boy is magnificent. I am proud of you my dear lady. I am also proud of your daughter, the novice Katye. I am delighted that you have taken to spanking. I do believe this must be severe and perhaps the young novice, your delightful Katye, should warm his ass in readiness for your noble hand spanking! His blue balls is a consequence of being collared. If he complains -- keep up the spanking. Your writing is wonderful and I find both the writing and indeed thinking of you to be very very erotic. Fortunately for me I do not need to suffer blue balls!!!! I shall write properly very soon and tell you all about my trilogy. Meanwhile you and Kayte work closely together. The more exposed flesh with the two of you together in front of the slave while he is denied pleasure the better With deep and sincere affection my dear lady and novice, Lord M July 21: My Dear Mrs Millwood, You, dear lady, remain very much in my thoughts. I woke early and have had some thoughts I wish to pass on. These we need to consider over our next few letters to each other. I have been thinking about your daughter Katye and her growing role with you in the training / breaking in of the slave boy. While she is your daughter and that makes this a special situation, she is clearly your novice. This means you become responsible for how she develops as a Domna. To assist this I shall from now on address her and refer to her as 'MISTRESS KATYE'. I believe that Derek must do the same! This will form a large section of what we share and I would dearly love for Mistress Katye to write to me herself. I am happy for you to see our correspondence, but I believe it will help. The third issue is more personal and most important. We have focused exclusively on your role as Mrs Millwood to the exclusion of the sexy woman Tina Millwood. I wish to change that and discuss your needs and wants as a woman so that everything remains in a state of balance! You are a very dynamic and attractive person and a most attractive woman. Finally, I would be very happy, dear Mrs Millwood, if you would write to me describing how the spanking of the slave boy went and, most importantly, how he reacted. I suggest that Mistress Katye should spank him as a warm up on a regular basis. Perhaps in front of your girlfriends! I shall give some suggestions as to how this may be done. I send you my very warmest and fond wishes, dear Mrs Millwood, and with thoughts of care and support I am always yours. Lord M July 23: Hello Lord M, How are you today? Thank you for asking about Derrick's service to me. I have neglected to share in this regard. Yes, I have had Derrick pleasure me, and he is doing a very good job. I have complimented his 'eager tongue.' Since he has moved in, I have only recently allowed his cock inside me. I felt it important to train him to use his tongue for pleasure. Something about a pretty boy's face between my legs, licking me just makes me wet! He says he has never 'gone down' on a girl before, but he is doing very well. I have given very little instruction about how/when to lick, nibble or insert his tongue. It must come natural to subs. ;) Recently, I have ridden his cock, but I do not allow him to orgasm inside me. In fact, I do not allow him to orgasm at all after I use him in this manner. He needs to learn that his cock is a mere tool for my pleasure, not his. He has found this frustrating, to be sure. To help stave off an orgasm, I fit his cock with a tight rubber ring at its base. It allows him to become quite hard and engorged because it cuts off circulation out of his shaft. It also has a numbing effect upon him, making him last longer, much longer. It really does frustrate him to have to tuck his erection back into his underwear and fix me a drink. :) Yes, Derrick does pleasure me well with his mouth and tongue. He has very tender kisses. He is learning the art of foreplay, also, kissing my inner thigh, fondling my breasts, and using his tongue on my nipples as well. I certainly have no complaints about his tongue. He is learning that there are other erotic places on my body besides my pussy. He has enjoyed finding these areas, and using them to make me wet. I have also enjoyed sleeping with him. It had been too long since I have had a male sleeping next to me. As a reward, I allow him to sleep thru the night in my bed whenever he pleasures me sufficiently. Other nights are spent at the foot of my bed. As long as he is not vanilla, his domestic service is excellent, for the most part. He gets my clothes ready in the morning, and has breakfast ready for me, also. We're still working these details out, but when he's 'in heat,' his service in this regard is fantastic! I do enjoy watching his erection bounce back and forth as he scurries around. Katye, who usually is lifeless in the morning, has shown much more life now that she has something to entertain her in the morning. She enjoys taking a swat at his shaft as he sets the table and brings us our orange juice. Katye has been pestering me to allow her to use his tongue on her also. She hasn't asked to use his cock yet, I'm not sure why, but she is eager to have his mouth between her own legs. I haven't allowed it yet, and I do not wish to supervise, as I, a mother, do not wish to share my daughter's sexual experience. I am going to have to relent soon, and allow her to take him, otherwise, I'm afraid she'll bring some boy home of whom I would not approve. Perhaps I should allow her to use Derrick because I know she'll learn what to expect from a true submissive. She has participated in his discipline and supervision of his chores. I suppose she should be rightly rewarded. But for the longer term, she will need to find her own submissive. We cannot expect Derrick to service us both, and I am afraid there may be some friction between mother and daughter if we continue to share. Good male subs are so hard to find though. Your thoughts on this, Lord? I have more thoughts to share, and will write again soon. Hello Lord M, Unusually slow at work today. I thought I had better write now, because at the beginning of August, I will be away for about a week at a conference and will not have much time to write. I plan to take Derrick with me as well. This will be our first trip together. Should be fun! I will be honored to have the opportunity to read a private summary of your trilogy. I'm sure I don't need to say it, but I will, of course, not discuss or forward the summary onto anyone else. Concerning Katye, I think it is a good idea to have Derrick address my daughter at Mistress Katye. I hadn't thought of it, but think it's an appropriate idea. To be honest, when the idea of Derrick moving in first crossed my mind, I rejected the idea because of Katye. I didn't know how she would respond, and I didn't want to influence her own sexual growth by forcing this situation upon her. That notion seems foolish now, especially considering how I raised her and Kyle. I think I was just being a little too motherly, too over-protective. I have a few more thoughts to share concerning how I raised my children. Your correspondence has made me pause to recall their upbringing. My household has been more 'progressive' than most households, I believe. I have always been open with my children about sexuality, and have never tried to push them one way or another. I have allowed my daughter to go topless at our pool for the past few years, as long as there weren't boys around. I have sunbathed topless, (without children around) but outside of my close friends, I couldn't name another mother who would do that. I have also encouraged Kyle to be open about his body. I have not wanted him to grow up with the idea that women should be objectified more than boys. I had him grow up wearing a Speedo around our pool and over the past few years, he has worn Spandex shorts around the house. In fact, he usually wears those as his swimsuit now. M.I.L.F. vs Stud Ch. 03 But I think it's healthy for him to be on display every bit as much as Katye has allowed herself to be on display. She is used to seeing him dressed so, and has seen him at his wrestling matches wearing a singlet during his high school years. Now, she can feel good about how she displays herself, knowing that males are looked upon in the same manner. I am sure it has helped them mature, also. As they have grown up like this, both are accepting of the other without undo embarrassment or teasing. They have accepted it as normal. It goes along with what I mentioned in a previous email about the household chores. Both are equal in chores, too. Katye has taken to the domination of Derrick very well, and I have to admit, I am not nearly as self-conscious about it as I thought I would be. She is fine with the notion of me taking a young boy as my submissive, and has enjoyed him as eye candy. Slowly, I am allowing her more freedom in handling him. I have allowed her to take the responsibility of disciplining Derrick for minor infractions around the house. This usually consists of the drumstick to the testicles, her personal favorite. My Lord, I do hope you will not take offense, but I wish to keep Katye insulated from any outside influence right now. I may take her with me to a dungeon party sometime, but for now, I wish to keep our correspondence between you and me. I am sure I am being overly protective, and in time, I am sure I will permit her to correspond with you, but for now, I ask that you remain my special friend. I hope you will understand. Derrick did take his spanking very well. I have been using a Cat-o-nine tails on him as part of his growth as a submissive, and I have also been spanking him, so when I spanked him as punishment, it was not a total shock to his system. He didn't become completly hard, but was at half mast by the time I was finished. I did not have Katye spank him, but I do like your idea of having her spank him as a warm up. Thank you for that. I have not allowed Katye to grant him orgasms because I think she would do it for fun, and as I mentioned, Derrick too easily slips into vanilla moods. I can tell that she needs more education on exactly what orgasms mean to a boy and how drastically it affects them- to have an orgasm and to be denied an orgasm. You should have seen Katye's face when I applied the Ben-Gay to Derrick's penis. Her expression was priceless. She was so shocked, then nearly doubled over laughing at the poor boy's reaction. I had him tied down to a lounge chair and he fought the ropes, and had that chair bouncing all over. I find it amazing that he remained quite hard the entire time (about 20 minutes). Agonizing yet erotic, I guess. I must run now. Warmest Regards, Lord M, Mrs. Millwood M.I.L.F. vs Stud Ch. 04 July 26: My Dearest friend, Mrs Millwood. Thank you do much for your emails. I am very pleased with the progress in your stable, especially your slave boy. I am also delighted with the novice Mistress Katye. If I may make a suggestion about Mistress Katye, and I agree that you should keep the sex play for her within the stable, it is extremely important that as a novice mistress she have frequent and powerful orgasms. I do have some thoughts on this but would like to hear your ideas. Be aware that with the erotic nature of her environment. I a sure she is aware when the slave is pleasuring you, dearest Mrs Millwood and that is how it should be! You need to be frank with her and encourage her to be open about her sexual behaviour. Also my dearest, be aware that she needs your direst guidance. Sharing the slave could, in fact, make your relationship with Katye even stronger than it clearly is! Now dear lady, I wish to share some thoughts I have about you and your pleasure. While the slave can pleasure you whenever you so order, and order you must, there are other issues to your womanhood. I know full well that you are very turned on by the slave's youth. I often watch my wife on the verge of an orgasm when she sees young men, especially their bottoms! However, I would like to send some special correspondence to you as a mature man, an aristocrat and a master. Remember I am NOT your master, our's is and must always be a level one. I simply have been around longer and have a long family history with servants (spanking across a wine barrel is superb!). I think about you very often and my thoughts are very erotic. My preferences have grown with maturity and the best turn on id a woman in continuous orgasm, especially with my face between her thighs and my tongue buried very deep. If you would like me to write such letters please tell me because I would never make such an assumption. Related to this, I totally respect your wishes about Katye and I am honoured that you wish me to treat only YOU, my dear Mrs Millwood, as my very special friend. I will write more when I have more time to myself. I have much to say about your novice and your slave and, indeed, possible new blood for your stable! For now, dear lady and very special friend, Mrs Millwood, think of what I have said. I would love to write in this way! My thoughts are with you all. With deepest affection, Lord M July 29: My dear Lord M, I had hoped to correspond earlier, but this week has been crazy. I can write now because a meeting was put off, freeing some time for me. I am going away for a week, next week, and I have much to prepare. Also, I cannot promise to write much next week while I am away, but I will certainly check my inbox in hopes of seeing a letter from you. Oh, in addition to being busy with work, I have to concern myself with Kyle. He's coming home Saturday night. I may have told you, I'm not sure, that he was supposed to remain with his father for another month, but since he lost his job, Kyle's summer stay was cut short. I thought I had my ex talked into keeping him for another week while I am away, but I guess he changed his mind. (Typical!) My original plan was to have him stay with one of my girlfriends, but naturally, she is also going to be away. She's going on a 2-week vacation. Could things align for me any worse?! I suppose there won't be a problem since I'm taking Derrick with me. It will just be Katye and Kyle here. That's fine. I'm just concerned with what to do when I return with Derrick in tow. I have thought, perhaps not as much as I would like, about what you wrote. You have some wonderful points. Honestly, I hadn't considered it, but yes, I believe it is important for Katye to experience very powerful orgasms early in her Domma training. She will learn the value of the submissive and want expect nothing less than that going forward. She has been brought up to expect only the best of herself and others. To ensure this, I understand your comment of having me supervise her sexual experience. Up until now, I have been very conservative in this regard, which is funny, considering that I am far from conservative, otherwise. I think it's a stigma I need to work through. The problem is, your Lordship, I simply haven't had time to think about it. I will consider it while I am away. Yes, Lord M, I think I might enjoy some "special correspondence" from you, if you are so inclined to write. I must confess to you, My Lord, I am trying to sound experienced and knowledgeable, but I am very much a novice myself at training subs. I am relying on my girlfriends for guidance as well as you, of course. Of all of my friends, you surpass us all with your expertise. I think you would look at us and consider us a half dozen bored old women who decided they had nothing better to do but collar young boys! :) Well, perhaps we're not that bad.. I hope to be able to write before I leave on Sunday, but I cannot promise. I hope all is well with you, Lord M. How was your getaway with your wife? How is your trilogy coming along? Thank you again, My Lord. I must go. I am frazzled here at work. Thank you for giving me a place to vent and escape! Back to it now, though. Warmest Regards, Mrs. Millwood My dear Mrs Millwood, It was such a supreme pleasure for me to read your correspondence today. Thank you. I am extremely happy with your progress, and for this email I wish to focus on YOU, my dear friend. Mrs Millwood, I want you to know that I am very aware that in training Mistress Katye you are yourself a novice. I also wish you to know, dear lady, that you are superb. As for your relationship with your girlfriends, you are totally wrong in how I view that scene. I find you all to be very exciting. I consider you a very, very special friend and one who I would make a lover were we living closer than opposite sides of the world! Indeed, dear Mrs Millwood, there is one thing that saddens me a little. It is that you have a tendency to put yourself down. I believe this is changing for the better and will change totally. This is evident in the manner of your address to me today: My dear Lord M. I did enjoy seeing this and ask you to continue! This suggests that you are becoming sufficiently comfortable with me to begin expressing affection. This pleases me a great deal because I do, indeed, feel much affection for you, dear Mrs Millwood! As for the situation with the return of Kyle, while I do see that it appears to be most unfortunate timing with you girlfriend being on vacation, I believe it may be what my dearest mother would have called 'a blessing in disguise'. Permit me, dear lady, to explain. Mistress Katye is wonderful. You, my dear friend, have done and continue to do a magnificent job. It is precisely because of the skills you are developing and your preparedness to extend yourself that I recommend your involvement in the sexual training of Mistress katye. She could not have a better teacher. It is because you are her mother as well as her Novice Mistress that your love will guide you as intimacy develops. Mistress Katye is, I am sure, more than prepared to do whatever seems fit with young kyle in your absence. I am equally sure that she is well aware that should she go beyond any boundaries you set that her own pretty bottom will feel your hand. That, my dearest friend, is an absolutely essential part of her training. Having said that, I do suggest, dear Mrs Millwood, that you set those boundaries fairly wide. Both Mistress Katye and Kyle are familiar with the sight of each other's bodies. Allow that to continue, even in your absence. This may be a big leap but I urge you to take it. As for your delightful self, I keep thinking of you sending the email to me before writing it because you felt some excitement. I also picture your slave lapping your love juices. To be frank, dear lady, you have turned me on towards you. I remember once talking on the phone with a sub. Her husband was in the same room as her and both she and I had the phones on speaker. She had the most amazing orgasm from how I spoke and her husband was delighted. The orgasm must have lasted 20 to 30 minutes and left her exhausted. As I think of you I so much want to be down there with my face between your sweet thighs. I want my tongue to explore those pussy lips and to find your clit and take it very slowly into my mouth. Then as I bite gently on your pussy lips and clit, with my hands lifting your lovely bottom high, my tongue would deeply enter you hot cunt. That, dear lady, is something of an entrée. I shall write more personal material for you later as something special for you! This email, my dearest, has focused on you, on your feelings, and what I perceive as some trepidation over the return of Kyle. I sincerely hope that I have helped, that I have eased any anxiety you may feel. I shall write more later and focus on the needs of Kyle, I think that is dominant right now. I shall also focus on the issue of Katye and HOW you should proceed in her deeper sexual advancement. I shall write several times while you are away, if only to remind you that I am her thinking of you, my dearest friend. I understand that replying to my correspondence may be difficult. I would appreciate something however, a couple of words to say 'hi' to me, even another email without words (I am smiling at that one!) For now, Dear Mrs Millwood, try to relax and enjoy your week with the slave boy! One last word. You have made great advances. You are a novice at the training side and dealing with your children in this context. You will know that you have graduated beyond that when my address to you changes. I believe you will enjoy what I have in mind! With much love and deep affection I am always Yours Lord M August 4: My Dear Mrs Millwood, I trust that you have arrived safely and are enjoying your time at the conference and your time with the slave boy Derrick. I hope all goes well for you this week and provides some respite from the usual day to day work. I hope all is well with Mistress Katye and her time with her brother Kyle. I am very interested in how things are with them. Take care, dear lady. Enjoy your week away and know you are very much in my thoughts, I am as always your dear friend and confidant and I send you much affection, Lord M Hello Lord M, Yes, I am enjoying my time away. It is nice to see some old collegues. It would seem that I have acquired a new nickname, "Cougar T." My closer collegues are having fun with it. A few others are enjoying it,but won't comment for fear that I might snap them in half, I think! ;) I have never seen such sour-puss faces on a couple of my female associates as when they saw Derrick at my side, while we were going to dinner. I felt so good Derrick has seemingly become popular around the pool area with the bored wives who have tagged along with their husbands. Those husbands are none too fond of my arm trophy. I have created quite the stir. I have to admit, I really do enjoy it! I may have to lock him in his chastity device!! ;) I hope all is well with you, my Lord M. I appreciate knowing that you are thinking of me often. I admit, my focus has wondered to our conversations while in the mid-day conferences. Warmest Regards, Cougar T. August 7: Hello my Dear Lord M! I had to take this moment to write. As I type, I have my sub, Derrick underneath the desk, naked and hard, wihth his face buried in my pussy, licking the juice that flows! Oh my god, Lord M, this does feel so good!! I have always wanted to do this, rwrite a letter describing what is happening to me as i hav e aboy eating me out. pauase pause.... His tounge is workign my clit. OH jesus. Oh.........Oh that boy has a tongue to fucking die for! I know my spellings a bit off, but at the moment iam typing wne hand whilethe other isd pushing his fucking head as hard into my clit as i can i am grinding hard on the cocks chin. oh fuck, I just lost teh bet. I was sure I could hold off from cumming while I wrote teh email. He was sure he could make me cum all over his face before I finished. I guess I lost. Losing has never felt so damn good. His reward is for me to ride his cock tonight. He won't be allowed to cum inside me, but it's been a long time since he's even been ridden. Excuse me while I fuck his ass. mrsmillwood My Dear Mrs Millwood, What a sexy, horny woman you are, dear lady!!! I love your description of your slave boy licking out your hot pussy. You made me so horny too, dear lady. You mad me rigid instantly! It is very clear that you have trained the boy very well so far. I trust he enjoyed your strap-on up his posterior and that you enjoyed it too. I must say I have been picturing my tongue buried deep inside you, my teeth pulling on your cunt lips and my throbbing cock then filling you balls deep! I trust that the slave enjoyed riding you and, more importantly, that you came many, many times. I must tell you that I could t4ell from your writing, and NOT just from the spelling, that you were approaching and feeling that tipping over the edge sensation. I trust you gave his bottom some sexy (not punishing) spanks and his balls some sexy squeezing. You are giving me some interesting thoughts about where to take all this. I shall give serious thought to the matter and then write in detail. With much affection and a very hard Cock Your Lord M M.I.L.F. vs Stud Ch. 05 Call it Mother's Intuition, I guess. I decided to come home one night early. I talked to Katye and Kyle nearly each night by phone, and I could tell that they weren't telling me something. There was just something in the tone of their voices. So, I didn't tell them, but I rented a car and had Derrick drive through the night to get us home Sunday morning at about five AM. Actually, we drove to the airport where I picked up my car, and came home from there. The house was quiet, but there were obvious signs of a party. Beer cans and a few empty liquor bottles strewn around the house. I was glad to see there was no one passed out anywhere, but still, I was pissed off. I made sure Derrick and I left no signs of our early arrival, save for the car in the garage. We went straight to my bedroom, where we took a little nap. I let Derrick continue to sleep while I went out to the patio off my bedroom to think things over. It happens to overlook the pool and deck area, but is still secluded by shrubbery and an assortment of small trees. The pool looked fine. I didn't see any bodies floating in the water...you never know. Well, I had a newspaper to read, and I had grabbed some fruit from the kitchen before retiring to my room, so I ate that. At some point, I dozed off. I was jolted awake by a girl yelling, "Hey K, the little bitch is out here." It's amazing how many thoughts can go through the mind in a split second. Before I had even opened my eyes, I was sure that she was referring to me, and I was quite offended, ready to go at it with her. I opened my eyes to see this tall, very fit black girl, wearing only a pair of skimpy boyshorts, lifting a blanket off the futon less than 30 feet in front of me, revealing a slumbering boy hidden beneath, sprawled out, also completely naked, and yes, sporting quite a morning erection. One second, I was relieved that she wasn't referring to me, then the next I was back to being shocked when I recognized the boy on the futon as my son. I was close enough that I could see that his shaft was a very deep shade of purple and very large. He had a cock ring tight around the base of his shaft, and must have had it on all night. The girl held his shaft and seemed to stare at it for a second, and that's when I noticed something metallic at the head of his cock. She reached down with her other hand and pulled at the metallic head to reveal a stem that was inserted inside Kyle's penis! She fucked his penis with it a few times before re-seating it fully into his shaft with only the head displayed. It was a cock plug. I recognized it because I bought one for Derrick off of Stockroom.com. I shared this site with Katye and showed her the items I had purchased when they arrived. I checked later in the day to see if she had taken some of Derrick's 'toys' to use on Kyle, but they were all still there. She must have bought that thing on her own. The other item I noticed was the sizable ball stretcher he had locked around his testicles. It was large, and it kept his balls good and tight, but he seemed to handle it okay. Kyle was stirring, but not quickly enough for the girl, so she gave his bound balls a good slap. That immediately brought him back to life. He sprung up out of reflex, and that's when I noticed the black collar around his neck. The girl latched a finger onto the ring at his throat and pulled him up from the futon. Could they have done anything else to him? My god! Kyle stumbled forward, still in tow, wiping the sleep from his eyes. I only had a partial view of his penis as his back was towards me, but it seemed to be bouncing all around, unable to remain upright because of the tight ring at its base. My best view of him was of his backside. Admittedly, he has a nice muscular ass. Just before they became blocked from my view by the corner of my bedroom, this girl landed a nice smack to his left butt cheek. I heard an "Ahhh!," and "a little faster. That's better," before they entered the kitchen. The whole time, I don't think I moved a muscle. I didn't know what to do. My mind was racing. Part of me wanted to run back into my bedroom and try to erase my memory, another part wanted to run out there and kick that girl's ass for treating my boy like that, and yet another part wanted to just sit there, too petrified to move. It took me a few minutes, but I did finally get up and scurry back into my bedroom, making sure to take all of my things with me. I wanted so badly to creep down the hallway to listen to their conversation, but there's a point in the floor where it creaks, and I couldn't take the chance of blowing my cover. I could, however, watch from my bedroom window. I rustled Derrick from the bed and had him come watch with me. Not even his morning erection would distract me from what my kids were up to. We couldn't see into the kitchen from my window, but we could see the patio quiet well. We waited for nearly 10 minutes until the black girl came out, this time fully dressed with a top, but still in the boyshorts and flip-flops, and said "...all right. See ya later," and left through the back. A few minutes later, Kyle came back outside, his cock had wilted some. Now it was curving downward, but still full. I found myself fighting the thoughts that I was feeling as I saw him. I felt my pulse race when I saw his manhood again, and for the first time, I got a good look at his balls which hung freely between his legs. They had removed the stretcher. From the length of his ballsac, I'd say the stretcher had done a good job. Kyle began to fill a trash bag with the cans, bottles, and plates that were left out after the party, when Katye finally made her appearance. She had come out to help Kyle clean up. She came out in her bikini, which is more than Kyle was wearing. They seemed to be focused on the job at hand when Katye sneaked up from behind and wrapped her arms around Kyle and began assaulting his cock. They were again facing me, nearly in front of my window. I froze and could only hope that neither one would look up and see me staring. It occurred to me then what she was doing. I had shown her earlier in the week that a boy could cum without being hard. A cock in the rubbery state, long but soft, can easily be stroked and squeezed like an utter to produce boy's milk. I demonstrated that for her last month with Derrick as the test case. He didn't realize he could have his 'boy milk' taken from him so easily. I think he was a little humiliated by that, but Katye was enthralled. So I think what I was witnessing was her own attempt on Kyle. His cock was in the perfect condition for this milking treatment, long but soft. He didn't last more than a thirty seconds. I could tell that he was more surprised by what he felt, and knew was about to happen than Katye was. I could hear his orgasm mounting within as he was powerless to fend his sister off. Katye let go, and bounced around to the side to watch him fight with futility against his rising orgasm. His cock was still pointing downward when his semen streamed out the end. His cock bounced a few times as more of his cum slowly streamed out. Amazingly, he fought the urge to stroke himself to a more fulfilling orgasm. The anguish on his face told me that his orgasm was flowing through his body, demanding that his cock receive more attention before it left him completely. I can only assume that Katye was warning him not to touch himself, which he didn't. They both, well, actually, all four of us (Derrick was present) watched as Kyle's cum pooled between his feet right in front of us. I heard Katye exclaim, "YES! Told ya I could make you cum without being hard! Ha! Clean it up, little brother." To be honest, I was so proud of my daughter. I was proud that she took the initiative to try the experiment, and I was also proud that Kyle didn't take his penis in hand to finish himself off for a more robust orgasm. I can only guess that Katye taught him this discipline. That said, I was shocked by my own reaction. I should have been horrified and gone out to stop it, but I didn't it. At that moment, I was simply a voyeur. Kyle was well drained, but not fulfilled. His cock remained full, but his balls hung low, as if empty. Then it occurred to me that I should take this opportunity to have Derrick go move the car while they were both outside. As soon as they took the trash out to the garage, they would see the car, and realize I was home. But if Derrick were fast enough, he could get the car out without them hearing him, as long as they remained outside by the pool. I told him to just throw on his shorts and go. I'd call him later when it was safe to return. For a moment, I thought I should join him, but I was too intrigued. I had to watch these two. Then I started feeling guilty for coming back early and spying on my grown children. I didn't know if I should wait in hiding the entire day until they hopefully left, or if I should walk out like I had just woken up and didn't see a thing, or maybe I should confront them both and demand an explanation. Before the sex incident, I was prepared to confront them and demand an explanation. Now however, it was I who felt as though I had invaded their privacy in a conniving manner. And the other thought was what if they came into my bedroom for whatever reason? I hurriedly made the bed and put our suitcases in my closet, sure that they wouldn't find them there. Derrick made a clean escape, as Katye and Kyle both remained outside to clean up the pool area. Kyle remained naked, and I don't think that he even asked to put something on. I could see that they were talking, but it was very difficult for me to hear anything. I had left the patio door open, but they weren't anywhere near it. At some point, I am pretty sure that Kyle complained about the ring at the base of his shaft, because I saw him move it around a little. Katye came over and seemed to grant him permission to remove it. He took it off with great care and obvious relief. They did a good job of cleaning the outside, and moved inside to clean. I was actually disappointed to see them leave. I was enjoying the show. I was a little less apprehensive about watching them by this point, but still concerned with how to proceed. I sat quietly in my room, a prisoner in my own house, intently listening for the alert from the creaky hallway floor. It never came. I started thinking about where Katye got the cock toys. It took me a while, but I remembered that I had a box full of sex toys hidden away in the attic. I hadn't looked for the box in years, and never considered using the toys on Derrick, as I wanted to start with new toys on him. I couldn't check the attic at the moment, but I was willing to be the box would be empty. Then the question begged to be asked, 'just when did she find the box?' I never mentioned it to her. Did she just get it out after I left last week, or has she been in possession of these things for a lot longer? And that made me wonder, 'if she had them for longer, how long has she been using them on Kyle, assuming he was the intended boy?' After about thirty minutes, I became bored of watching a lifeless patio, and I was getting hungry. I called Derrick and had him pick me up one street over. After giving the room one last check, I quietly exited out my patio and around the back of the house. My biggest fear now was that a few neighbors might see me, but I think I made it out safely. After devouring a chicken Caesar salad, Derrick and I made our appearance at the expected time. I really had no idea of what to expect, even from myself, when we walked into the house, but it certainly wasn't what I got. They had a surprise 'welcome home' party for us. I couldn't have been more surprised. One party wasn't enough, or was last night just a warm up for them? We came in through the garage into the kitchen, and were met by Kyle who was preparing some drinks. There were hugs and kisses all around. Maize, and my other girlfriends were there (except for Heidi who was on vacation) in their usual places near the pool. I was a little surprised that Cynthia was there with her three kids, but there they were. (I must confess that in a previous post, I told you Cynthia had two kids. I didn't mention the third because I never felt she would be involved in any scenario, but ironically, I have to mention her in my story now.) There were a whole group of girls there who I had never met before. As it turns out, they are friends of Katye's, or friends of friends. Things were too festive to try to address the unauthorized party of the previous night. I also didn't sense that either Katye or Kyle had any idea that we had actually been home already. So, I just decided to enjoy the evening and see where things went. My older friends and I moved inside where we could have some piece and quiet. We let the kids have the pool area to play around. I even let Derrick go play with them, as he had served me admirably over the previous week. It was getting rather late; I was in the laundry room, which is near the kitchen, when Lori, Cynthia's youngest, came scampering into kitchen, out of breath, and holding a dripping pair of boardshorts which just happened to belong to Kyle. She handed them to me saying, "Here Aunt Tina," still catching her breath but with a big smile on her face, "I'm supposed to hide these somewhere." I was very surprised, to say the least. "How did you get these?" I could see that the girl saw this as a very fun game. "I pulled them off Kyle!" She said, looking back out towards the pool. "You pulled them off Kyle?" I repeated, not believing my ears. "Yeah, all the girls are dunking him, and they were trying to take his shorts off. I jumped in and started tickling him, and then when they had them down around his feet, I was the one who pulled them off. And he didn't have anything on underneath. Laticia told me to go hide them," she stated proudly, still with a smile from ear to ear. She took a quick step back towards the door when I grabbed hold of her. "No, I don't think you should be going back out there with a naked boy in the water." "Well, he has, they called it a ball stretcher on." "Oh my god, you saw that?" "Yeah. It looks funny. I want to see it again." "Oh no you don't. In fact," I said bending down to her level, "how about we just keep this between you and me. Your mother really doesn't need to know about that. Are your brother or sister out there too?" "Yeah, they saw too." "Okay, well, I'll talk to them, but let's just keep this between us, all right?" "Okay, but I want to go back out and help dunk Kyle." "No, I don't think that's a good idea. You did your job, now stay inside with us. I think your mother is ready to leave anyway." She was disappointed, but she followed my direction. I went out and found her siblings, Brandon and Jessica, who had already begun to dry off. I didn't ask them what they saw, and I only caught a glimpse of the continuing horseplay in the pool. By this time, Kyle had extricated himself from the girls, but I couldn't tell, and didn't really want to know, if he were naked. I only asked the two kids that they keep this all quiet from their mother, as they would be unlikely to ever come over again after having been exposed to that scene. They both agreed, but I could see that their minds were working overtime, having never seen something like that before. I would have to do damage control with them at a later point in time. After I walked my departing guests out the front, I immediately made a B-line to my room where I could spy on the pool scene undetected. To my surprise, most of Kyle's and Katye's friends had left. I saw them close the fence gate behind them, and I heard Derrick walking down the hall, which left only Katye, Kyle, and Laticia in the water, in very close proximity. Laticia was nearly nose to nose with Kyle, her hands below water. She had an evil grin on her face. With a nod from Laticia towards the futon, Kyle jumped out of the water, and made his way there, with full erection, and yes, wearing a ball stretcher. I gasped. He flopped himself down on his back as Laticia sauntered over to him, standing above him dripping onto his face. She seductively slipped her bikini bottoms down her smooth slender legs and let Kyle get a good look at what was coming his way. His cock throbbed. Laticia said something to Katye just before straddling Kyle's face, settling down with her pussy right over his hungry mouth. She began to slowly grind her pussy on Kyle's lips, raising herself at times to let him lick her lips gently. She was facing me, but I was pretty sure she couldn't see me, as the lights were off in my room. I stood, watching from my window, the same window as I had spied on them before. She continued to grind, holding Kyle's head in her hands, arching her back, feeling the orgasm build within her. I knew he was doing a good job when she gasped. I assume he was nibbling at her clit. In the meantime, Katye had taken up position behind Laticia, and I think was stroking Kyle's cock. Laticia looked back at one point, saying something, I assume telling her not to let him cum. Katye then repositioned herself, placing Kyle's left leg over her shoulder and I believe, began fingering him. His body seemed to jolt at what I suppose what the intrusion. He relaxed a bit once he became used to it. I'm really not sure how long this went on, but Laticia couldn't hold the orgasm off any longer. I could see the muscles in her arms flex as she squeezed Kyle's head up to her pussy. She ground her pussy into his face harder than I have ever seen before, and tried hard to subdue her cries of pleasure. Once her orgasm finally swept through her, she kept her position on Kyle's face, catching her breath. She raised up slightly to let him breathe, I think, and to let him lick her swollen wet lips once more. My heart nearly stopped when she abruptly looked up, straight into my window, raising her pussy inches from Kyle's face, smiling as the last of her juice trickled down into Kyle's open mouth. I am sure she knew I was there. I'm just sure of it. She didn't change her gaze at all, even as Kyle extended his tongue to tickle her lips. I was frozen. I couldn't move. Laticia stood, faced my direction again, as she pulled her bikini bottom on. I must say, she did have a wonderful ass. I can understand why any boy would want it in his face. Katye had taken a seat on the ground next to the futon, nearly ready to pass out, I'm sure. Laticia turned, bent down to the resting boy on the futon and slapped his balls, causing him to come back to life, if only briefly. Again she turned in my direction and smiled and said something, but I couldn't make it out. There are some people, not many, who command respect and...fear. (Not sure fear is the right word.) I must confess that I was intimidated by her at that moment. I hadn't met her before, and just from watching her early in the evening, there was something about her that demanded I respect her. I think it was the way she carried herself. Very confidently, I would say, especially given what little she was wearing. This nearly six foot tall woman was not shy about strutting her stuff. She strutted around like a model would. And I must confess, she does have a wonderful body. She plays on the university basketball team. To play on that level, you would have to be very self-confident. I recall being that self-confident when I was in competing as a body builder. I can absolutely see that she has dominance over Kyle, and probably Katye, too. She had cum all over my boy's face, left him hard as a rock, and made sure that I knew. At nearly six foot in height, I'm sure Kyle, several years younger and at 5'10, feels like she towers over him and is dominant to him, even though he is a well-toned boy. M.I.L.F. vs Stud Ch. 05 Laticia gathered her things, put her sarong back on, and let herself out through the back gate. I was left, much like my children were left: having felt used. A few minutes later, Katye regained her senses and roused Kyle to move inside to his bedroom. I watched as he made his way over to the pool, knelt down and dunked his head in the water to wash his face clean of the remnants of the girl's orgasm. I have to admit, I admired his full cock and balls swinging between his legs as he did so. As he walked back towards the house, water dripping down his chest, I did truly admire his body. Perhaps I too, had had too much to drink. I thought about intervening at that point, and now I wish I had because when I awoke in the morning, Kyle was already gone. The effects of the alcohol on me were worse than I had expected, and it was nearly noon before I made my way out to the kitchen. I found Katye and Derrick in the kitchen, rehashing the events of the previous night. I asked to talk with Katye and her brother in private, and that's when she told me that Kyle had already left. I was crestfallen. I excused Derrick, and sat down to have a private conversation with Katye. "Yeah, he got up at about the same time as me, and he was so embarrassed. He said that he remembered what happened and what Laticia said." "What did Laticia say?" "Well," Katye looked quiet uncomfortable, but I needed to hear all of this. "She said 'nice bitch you got here, Mrs. Millwood. He's my bitch now.' That made him think that she was talking to you, which meant that you must have been watching. Were you?" I was caught off guard. "Well, yeah, I did see what happened. I didn't think she saw me though." "I think Kyle was totally humiliated. I told him just to go to bed and don't worry about it, but he was still feeling bad this morning. He wanted to get out of here before you got up. He's too embarrassed to face you." "Well where did he go? When will he be back?" Katye looked down at her coffee. I don't think he's coming back. Laticia has been trying to get him to go live with her off campus. A bunch of the female athletes have a house, and she said he could stay with her rent free. She called him her 'houseboy.' I didn't think he'd actually do it, but I guess he did. "Houseboy? Is he going to be their maid?" "Actually, yeah, I think so. If he helps keep the place clean, he can live there for free." "Oh my god, she's just going to make him her bitch, just like she said. Who else lives there? Isn't there some sort of adult supervision? Is this a sorority?" "It's not a sorority, it's just a bunch of woman soccer players, basketball players, and I think a few swimmers who all live in this one big house. They do have a housemother, but it didn't sound like she does too much there. I've met her once. She seemed kinda lazy to me. They, like, get away with all sorts of shit." "How do you know Laticia?" "I just know her through Kimberly. She was the red-head here last night. We're friends, and I had gotten to know Laticia and a few other girls through her. They came over a few times last week and met Kyle then." "So you had parties while I was away?" "No, we just had a few friends over, that's all." "Oh, so Saturday night wasn't a party? The beer bottles and trash were all for effect?" Katye was taken aback by that. You should have seen the look on her face. "Oh shit, how did you find out about that?" "It doesn't really matter right now. I just want to know how well they all 'got to know' my son?" "Uhhh...pretty well." "So Friday night was representative of all of last week, right?" "Well no, at first, it was just five or six of Kimberly's friends. Friday night is when a few more people came over." I was getting rather angry, as you can imagine, by this point. I nearly bent her over my knee and gave her bottom a good hard spanking, but I thought that could wait. With as angry as I was, I was afraid I might draw blood. "So you let these women, who look like their in their mid-20's, come over and use and abuse your brother, who is still a teenager, then you don't stop him when he runs off to live with them. Jesus Christ, Katye! What's wrong with you?" "It's not my fault! He's an adult! He's going off to college now, ya know. He's a big boy, in case you haven't noticed. He can handle himself all right with a house full of girls, I'm sure." "He is a big boy! That's the problem! A big eager boy who wants a lot of attention. And you know damn well he is very impressionable. He's submissive; we've talked about this! Laticia is a dominant. She's like a hawk looking for new prey. I know most girls aren't like that, but Laticia is a very different woman. Yeah, Kyle has a well toned body, but that just makes him more appealing to someone like Laticia. He's an easy conquest, obviously." "Well so what? You wanted him to go live with a dominant woman!" "But Heidi is someone I know and trust. This Laticia is someone I do not trust. How do you know what they'll do to him? You think there won't be some men coming over? Think they might not like a few minutes alone with a cute white boy?" She didn't know what to say to that. I think I finally go through to her. I continued, "Can you go over there and try to talk him into coming back? There's nothing to be embarrassed about. My god, he has to know about my relationship with Derrick." "Yeah, he does, and he doesn't really know how to process that. And, he just doesn't want you to know about what he does sexually. You know, you're his mom." "Oh Christ. He doesn't know that I know he's a submissive, that he likes being dominated? Please, just go over and try to talk some sense into him. But before you go, I want to know exactly what they did to him last week. I have to be ready." Katye had been very forthcoming but she clearly didn't want to divulge that information. I had to ask again, a little more forcefully. "Let's just say...he isn't a virgin anymore... I mean up the butt, too." I didn't know what to say to that. "Laticia had her way with him?" By the look on her face, I could see something was wrong. "It wasn't Laticia?" I asked. "It was...but it was more like a gang-bang. They all took their turns." "Oh my god." I thought for a few moments and stated the obvious, "She's right. He is their bitch." I fought back a few tears. I was too mad to cry. "Ok, don't...don't talk to him right now. This is something he has to do. Hopefully, he'll get tired of being a bitch for those bitches, and he'll get the hell out of there. "Are you sure he's not coming back? Did he pack his things?" "He already had things loaded in his car before I saw him. I know he packed his duffle bag and backpack. That's all I saw." "Did you take the ball stretcher off or was he still wearing it?" "No, Laticia has the key." "I can't believe he lost his virginity to her, of all people. I had actually thought that maybe you had claimed it. Katye looked at me in shock. "Are you kidding me? No!" "You mean, you never...had him?" I asked. "No, I mean we did a lot of things, but I never used the strap-on on him." "I know you – or at least I think – you used those sex toys on him for a while, right? Friday wasn't the first time he had had those on, right?" "Yeah, we found those a few years ago when we were looking for hidden Christmas presents." "Oh, well, that was quite a find." "Yeah, at first, we didn't really know what they were, other than something for sex. But there was a magazine in the box, and well, a picture's worth a thousand words..." I just nodded my head, "Yes it is. How long have you been sexually active with him?" "He never fucked me, if that's what you mean." "I just mean...okay, he never fucked you. That's good. I thought he probably had." Katye thought for a few minutes, probably deciding whether or not to say anything more. Again, she wouldn't look up at me. "Well, we fooled around a lot. It was mostly me getting him off. I liked watching him get hard at the pool. He wore the spandex because he knew I liked it. And some of my friends did too. That's when we realized he was an exhibitionist, I guess. He liked having girls check him out. "Then we decided to experiment with the toys we found. He was big enough for that stuff by then, two years ago I guess." "You're sure you didn't use the strap-on on him?" "No, I swear I didn't. I thought about it, but I didn't." "The plug?" "Yeah, I talked him into that. He liked it, though. He liked the cock rings the most, though. He always had one of the larger ones around his cock and balls. He even wrestled with it on. He liked how it pushed his package out further. He said he got a lot of stares from the mothers in the stands. More than a few phone numbers too. Last year, his balls were big enough to keep the stretcher on without coming off. I made him wear that when he pissed me off. I think it worked, too." "What do you mean?" "I mean, he like, chilled more. It settled him down. He did what I said." "He became more docile, more submissive." "Yeah, totally." "That's what it's supposed to do, besides stretch him out a little. The strap-on will do that too. That's why I'm concerned that Laticia and the others took him with a strap-on." It became harder to hold back the tears, so I got up and walked out onto the patio. I had Derrick fix me breakfast. I tried to get Kyle out of my mind, but of course I couldn't. I had Derrick give me a complete body rub down, and I even rode his shaft to an orgasm, but only alcohol helped me escape. Well, I suppose he's going to learn an invaluable lesson. I just hope he survives. Oh, what shall I do? My boy is now becoming, not a man, but I guess a submissive. I don't think of him, as a submissive, as any less than a man, just different than a man. I was on the fence about training him as a sub. Now, I wish he were here, because I would absolutely teach him this important part of his life. Why shouldn't I be the one who trains him? After all, I know what's best for him. I love him. This Laticia will use him and spit him back out when she's had enough. M.I.L.F. vs Stud Ch. 06 I have received some email asking for some background on Katye and Kyle. And based upon where this story is headed, I thought a little background on Kyle might be a good idea. I have asked Katye for some help in writing this since she was a vital part of his sexual awakening. Readers, please remember, my kids did not exist before the age of eighteen, when they spontaneously existed of-age. ***** Katye: I guess the first thing I want to write is that I love and adore my little brother, Kyle. Even though he's big and strong, I still think that I need to protect him. God, he's just so beautiful that I don't want anything bad to happen to him. I guess that's just the big (dominant) sister coming out in me. I guess I started working out to get in shape for competitions a few years ago. Mom let me take some 'supplements' to help me get bigger. She said that a girl has to if she wants to win, and it would help me be on a more even footing with my brother, if he were to get into competitions. I think Mom wanted me to get bigger so Kyle would feel compelled to get into competition level shape. He worked out with me, but he didn't have the drive to get big enough to win anything. Kyle was well defined, but not at all bulky. Mom didn't want him to get bulky, but he needed to have that drive, that desire to win, in order to compete. Mom's best friend, Maize, came over one Saturday, as she normally did, but this time she had presents for us. I had a competition coming up in a week, so Maize got me a new competition bikini. It was awesome! It fit me perfectly. It pushed my breasts up, barely covering my tits. And the bottoms fit low on the waist and looked more like a thong than a Brazilian cut. The directors of the competition were relaxing the rule that juniors were not allowed to wear thongs, but I would be one of the first to take advantage of it. Then Kyle opened his gift. It was a competition bikini as well. The look on his face was priceless. He was used to wearing tight revealing clothing by this age, but this took things to a whole new level. The piece of fabric didn't seem any larger than mine. Kyle began to object, but both Maize and my mom made him go try it on. He came out looking amazing. The black silky fabric was stretched to the max. Kyle was well developed between the legs, and I'm still not sure how that bikini held him in place. The front waist band of the thong was cut similar to mine. Instead of the band going straight across his lower abs, the band had a pronounced V-shape in the front. The cut dipped down from his hips towards his penis. He had to tuck himself down over his balls. Otherwise, his penis would have been completely out the top of this thing; that's how low this thing was cut. The style in the back was also a thong cut. The back strap was lost between his hairless muscular ass cheeks. I knew he would be the first boy to wear something like that in competition. Kyle began to protest, but Maize cut him off. "Listen. You haven't worked out nearly enough to win a competition solely based upon your build. So this bikini is going to put your best attributes on display. It'll get you the votes, I promise you. Male or female judges, I don't care. They'll all admire what you've got." "Yeah, as long as he doesn't pop out the top," I added with a laugh. "I've got that covered," Maize countered. Maize worked quickly. She reached out and pulled the bikini down mid-thigh, leaving his cock to swing half hard. "Hey, hands above your head, boy," Maize ordered. Kyle quickly complied, clasping his hands behind his head while she did her work. "You know better than that." Maize worked a small ring around the base of his cockhead, which made it look more like he had a noose around the thing. Then a second ring, attached by a leather strap to the smaller ring already around his cock, was worked around his balls. This forced his cock to remain tucked down over his ball sac in a nice tight package. There was no way he was going to spring free, no matter how hard he got. Maize pulled his bikini back up and tucked his manhood back in place. She gave his butt a smack, letting him know she was done. My god, his bulge looked amazing! His cock and balls were larger than most guys to begin with. These rings made it all seem so much larger, if that's possible. I was speechless. I thought I looked good in my bikini, but he was putting me to shame. Fuck! Maize grabbed his cock and gave it a shake to make sure it was secure. "Yeah, that'll work. Kyle, sex sells. What can I say? You just have to get used to being controlled like that," Maize noted. "Yeah, hon, it's time you started wearing something like this anyway," my mom said. You're at the age of eighteen and you need to be harnessed. Trust me, boys need restraint. You can't be trusted to remain in control over your sex. Boys are too weak. I've kind of talked to you about this before, babe. It's all part of growing up. Once you can control your erections and desires, then we'll talk about taking that thing off, but for now, I'd like for you to wear this for all athletic competitions and whenever you're out at the pool. In fact, you may as well wear it twenty-four/seven for a while to get used to it." "Even at night?" my brother asked. "Especially at night," my mom countered quickly. What neither my mom nor Maize realized at the time was that Kyle and I had stumbled upon a box full of sex toys similar to this about six months ago (when Kyle, who is younger than me, was 18 years and 1 day old) when we were snooping around for Christmas gifts. We had experimented by putting the cock rings around his cock and balls. There was one ring in particular that was nearly a huge problem. The ring was medium sized and made of metal. I made Kyle squeeze his balls through it. It took some work, but he finally succeeded. The problem was he couldn't get it off! It hurt too much to squeeze his balls back through the ring. Kyle ended up wearing it for about a month before he realized that some lubricant might help get it off. I thought of the lube shortly after he put it on, but I enjoyed watching him deal with it too much to offer the suggestion. Even with the lube, it hurt him like hell to pop the first nut back through the thing. I was hoping his balls would grow enough during that month that he would never be able to get it off. Came close. Anyway, Kyle was somewhat used to wearing these rings, but he didn't let on; nor did I. A little later that evening, Kyle and I were in the kitchen by ourselves when he walked by me. I reached out and grabbed his package, bumped my body against his torso and leaned into his face. I said, "You know, if you'd actually grow a pair and work out hard to get into great shape, you might actually win." It was so totally spontaneous. I didn't come close to holding his package in my one hand, but I did manage to get one of his nuts between my thumb and ring finger. I squeezed until I saw on his face that I had his attention. "Damn it, Kyle, you've got the looks and you've got the body, so just get in the god-damned competition or you may as well just give me these things so I can use them." He was fighting the urge to double over at this point from the pain I was causing him, but he had to pretend to be strong. I gave him my 'mad-as-hell' look then shoulder checked him before heading back out to the patio with Mom and Maize. From my peripheral vision, I saw Kyle holding his balls. I was really hoping that would get his attention. It did. Kyle came out and declared that he had changed his mind and would enter the competition and would workout with me every chance he had to get into shape. He asked mom if he could take some 'supplements,' but my mom wouldn't let him. She wanted him to be all natural. She also didn't want him to be big and bulky, just defined. She didn't really even care if he competed. She just wanted him to have a little more muscle and to work out with me so I could get used to giving a male direction. At the same time, Kyle would continue to get used to taking orders about his body from another girl. "Repetition is imperative," Maize said. We had to beat it into his head. TINA: Well, that's my daughter's recollection of the event that she thought was the turning point in Kyle's life. I'll pick the story up from there. About six weeks later, both Katye and Kyle were in a Juniors Body Building competition. Kyle had put on some muscle, but was still far from bulky enough to win solely because of his body. But he had his beautiful boyish face, and...well...the way he filled out his bikini. To our surprise, Kyle made it to the top ten. We were all so proud. As Katye, Maize and I were talking with Kyle off to the side just after the competition ended, one of the judges, Sotoya Clifton, joined us unexpectedly. After introductions, Maize and Katye went on their way. "Mrs. Millwood, you must be very proud of both your kids. I think Katye is a rising star if she sticks with it. And I understand this is Kyle's first competition. Nice job, young man," Sotoya said, reaching out to put her arm around his waist. I vaguely recognized her, but I couldn't quite place her. She was probably a woman I competed against in my younger days. She had the look of a woman who competed. She was in excellent shape still. "Thank you. I am very proud. Please, call me Tina." "Well Tina, if your son is interested, I run a private club for training. I specialize in juniors. I'm not training anybody right now, so I could take him on. Katye too, if she's interested." She tucked her card into the side of Kyle's waistband. "Can you tell me how you might help Kyle?" "Well, first off, I want to say that the choice of bikini was excellent. He wouldn't have finished top ten without it. It shows off his glutes very well." She ran her fingertips over the curve of Kyle's ass to further her point. "But let me be frank with you, Tina. Your boy is never going to medal without some coaching from one of the judges, if you know what I mean. He doesn't have the bulk to get there on his own. His package will get him to the top ten, but he's going nowhere from there." On one hand, I suppose I appreciated her candor, but on the other much larger hand, I was completely offended by her insinuation. Her entire demeanor rubbed me the wrong way. I think down deep, I knew I was being out dommed. I still considered Kyle and Katye to be under my control, and I had much to teach them. I was not going to let this woman lay claim to my boy like this. "And just let me be clear with you, I am not going to let my boy be 'coached' by you, or whatever you want to call it. I know how to train the boy to win. It's not all about size, I know that. But I am not going to allow him to become your little slut." I thought about it all afterwards. I should have been expecting the dommes to be coming out of the woodwork once they laid eyes on my boy. We can all sense a submissive. Kyle isn't an Alpha, and we can all smell it. They will all want to get their claws into the boy. I grabbed Kyle by the arm, told him to put his varsity jacket on and we marched out to the car. I could feel Sotoya's glare burning a hole through the back of my head as we left the gym. I had promised Kyle a double cheeseburger once the competition was over, so I pulled up to the drive-thru window to pick up our order. I couldn't help but notice the stare of the girl working the window. She couldn't seem to take her eyes off Kyle who was in the passenger seat beside me. I was still fuming from the confrontation with Sotoya, and I was about to lay into this girl as well. "Was this pimply faced geek going to try to make a move on Kyle as well? Damn," I thought. But before I cussed her out, I thought I would look over to see what had her so mesmerized, just in case it wasn't Kyle. I think I audibly gasped. It was Kyle all right. In my haste to leave the gym, I had given Kyle his jacket to wear, but that only covered him to his waist. What I failed to give him, and he must have been too afraid to ask for, was his sweatpants. So here I had this teenage boy sitting next to me, his jacket open and only wearing his bikini bottoms. He had walked through the crowded parking lot at the gym on display like that. Luckily, there was no one in the parking lot under the age of eighteen. And now, this girl who had surely never been so close to a male so well-endowed was getting an eyeful. I can only imagine what she must have been thinking. I pulled the car over to a parking spot. He had to get dressed before we went any further. "Hurry up and put on your sweatpants," I ordered. "But they're in the trunk," Kyle responded. "Well get them!" I was in no mood for this. "Fine!" he said. It wasn't until I happened to glance over at the restaurant that I saw why Kyle didn't really want to get the sweatpants himself. A hoard of high school girls, who all looked well over the age of eighteen, from what looked like a cheerleading squad were staring, mouths agape, at Kyle as he fumbled through his gym bag in the trunk to locate his pants. A few of the girls managed to snap a few shots with their cameras before my boy was able to better cloth himself. "Sorry, hun," I offered when he climbed back into the front seat. I was unable to attend Kyle's next three competitions, but it seemed that he was making progress each time. He finished tenth again, seventh and then fourth. I was so proud. But at the same time, I was puzzled. How was he able to improve without really having gained any muscle? I mean, he does sport a nice bulge, but that can get a boy only so far on the body building stage. I was walking back to my bedroom when I noticed the laundry basket sitting just outside Katye's door. It was Kyle's responsibility to wash, fold, and put the clothes away, so I knew he had to be in talking to his sister. I pride myself on trusting my kids and never snooping, but for whatever reason, I stopped to listen at the door. "So what do you think? She's not so bad, is she?" Katye asked her brother. "No, she's cool. I mean, she's stern, like Mom. I still don't see why Mom blew up at her when we first met her," Kyle responded. "Oh, it's a control thing. Sotoya should have talked to Mom privately first. And sometimes, when two people with the same personality traits meet, it doesn't go well. They're both used to getting their way, that's all. But I do think she's giving you good advice" "When she's giving me advice, I'm so glad that Maize makes me wear the rings. I couldn't control it otherwise." "I know! I can tell you're getting hard when she's touching you." "Oh fuck! You can tell?" "Oh totally. I mean, you're already big, but the head really swells." "Oh shit. Well, Sotoya hasn't let on that she's noticed." "Yeah, well she's a professional, so she understands. But I think you should try to spend some time with her. She'd do you a lot of good...in all sorts of ways." That's when I broke in. I couldn't listen anymore. I rapped my knuckles on the door and then opened it. Katye and Kyle were lying on her bed. Kyle's jeans were unzipped and partially pulled down from his waist. His T-shirt was pulled up enough to expose his right nipple. Katye was propped up on her side, fingering Kyle's 'happy trail' down from his navel to where it disappeared behind his microfiber Unico underwear. I was glad to see that he was still restrained. He looked full, but his penis was still arched down over his bound testicles. "Hey Mom," Katye said. "Oh hey. I saw the basket out here and wondered what was going on. Looks like I walked in on an Abercrombie photo-shoot." "Yeah, right. No, we're just talking about competing," Kyle offered. "Yeah, I'm trying to get this boy to do more ab work," Katye said, playfully rubbing his taunt six pack. Kyle laughed and rolled off the bed to his feet, allowing his jeans to fall to the ground. "And take that nasty shirt off. Throw it in the wash with those jeans." "All right, all right," Kyle responded. He whipped off the T-shirt and stepped out of his jeans. I was pleased with how well he had developed, standing there before me. "Kyle, I know I'm being tough on you, but if you'll listen to me, I know you'll medal every time. A boy your age needs to learn control of your entire body. I think it's already paid off. I just want to make sure you know that I have your best interests in mind. I don't want you listening to that judge. She has ulterior motives; I'm sure of it." "Yeah, I know, Mom. I'll get through it." "Okay, break time's over. Let's get these clothes put away." Kyle grabbed a handful of panties and bras from the basket. "And you need to fold my thongs right when you put them in the drawer. I don't like the way you do it," Katye said to her brother. "Oh please," I said, rolling my eyes before moving down the hall to my room. KATYE: "Hey, get your bulge back here. I wasn't done talking to you," I said to my brother. Kyle plopped back down on the bed beside me again. "There's one thing that Sotoya disagrees with Mom about. She thinks you need to be allowed to have an orgasm a few days before each competition," I offered. "No fucking way! Really?" Kyle leaned up on his elbows. I returned to playing with his trail. I saw his cock twitch, trying to break the bond that has held it in place for weeks. I totally felt sorry for Kyle. Mom had completely taken Maize's advice about Kyle's orgasm schedule. She believed that he should only be allowed release the night after a competition. But Sotoya believed that that makes a boy like Kyle too jittery up on stage. An orgasm two days before a competition would take the edge off but still give him time to recover, so to speak. I let my hand drift down over his cock. I gently squeezed and caressed it. Kyle moaned and let his head fall back. "Yeah, and she wanted me to take care of your needs. But I don't know what to do about this ring. You're too big to get it off your cockhead." But I soon found out that didn't matter. As I continued to stroke his bent shaft through his silky smooth underwear, Kyle arched his back and moaned loudly. His torso twisted slightly then he bucked his hips. I felt the first surge of hot cum spurt out his cock and through the thin fabric. My fingers were covered with Kyle's pent up juices. I was amazed at how much he had. He kept coming and coming. I had to scoop his cum up from between his legs before it hit my bed sheets. I wiped my hand on his chest before doing it again. "Fuck! I didn't know you could cum without being totally hard." "Yeah, if I need it bad enough, I can." "Okay, well fuck! You came a lot. You better get a good night's sleep to get your energy back. Maybe Maize was right." "No, I needed that. I'll be all right." "Don't let Mom see you like this. Take these off and get your lacey pair out of my dresser." Kyle removed his soaked underwear to expose his cum-covered balls. "Damn! Wipe your balls off too before you drip all over the floor." What a nice sight that was. Our Abercrombie stud was still seeping thick globs of milky white cum as he walked to my dresser to look for my favorite pair of underwear of his. I liked it when he had to wear this lacey pair that had fringe around the waistband. I liked the contrast of the feminine lacey panty on the defined, smooth, and masculine male body. He wore them well. Kyle tucked his spent cock and balls inside. The lace did little to his organs from view, but did hold them out from between his freshly shaved legs. "I'll let Sotoya know that you took her advice. We'll see if she notices it in your performance." M.I.L.F. vs Stud Ch. 06 After my cute - but spent- brother went on his way (chest covered with dripping cum), I texted Sotoya a snapshot of his Abercrombie ass as he walked out of the room. I told her that we were following her plan. I could only hope that it would help him. As it turns out, it did help him. For the first time, Kyle took a bronze medal home that weekend. Oh, and after two weeks of finishing in second, I walked away with the gold! TINA: After leaving the kids, I just couldn't help but wonder if Katye might take her brother too close to the edge. I didn't mind her toying with him, but he hadn't had release in nearly ten days, so it wouldn't take much for the inexperienced boy to go over the edge. I don't think Katye would give him release on purpose unless I gave her permission, but it could happen accidentally very easily. Maize had suggested that I have Kyle sleep in a chastity device to eliminate any temptation to masturbate, but I had decided against it. Kyle had proven to be obedient and resisted the temptation so far. But I saw the look in his eye as his sister was playing with him. He just might talk her into doing something she wouldn't otherwise do. I walked back down the hallway when Kyle came out of his room wearing something different than he was wearing when I left him only a few minutes prior. He was wearing the French cut panties that I would sometimes have him wear while doing housework. The French cut back rode up his ass very nicely, covering only the top of his muscular ass in a V-shape. But I had to wonder why he was wearing these instead of his Unicos. "Stop right there, young man. Turn around." Reluctantly, the eighteen year old teenage boy turned around to face me. He held a small pile of clothes in his hands, which he put down to his side. "Nice to see they still fit you," I commented, testing the front pouch for its elasticity. They still held to his body without a gap. "Why did you change?" "I have to do chores today, and I know you like to have me wearing these when I do them," Kyle responded nervously. Something wasn't right. I asked to look at the clothes he was holding, the jeans, T-shirt and underwear he had just been wearing. I picked up his white Unicos and discovered the problem. His underwear was covered in his semen. "Oh my god, boy! How many times did you cum in these?" "Just once." "This is just one load?" I asked, lifting my cum covered fingers from the underwear. "Yes, ma'am." By this time, Katye had come running out of her room to see what the fuss was all about. "Katye, did you have anything to do with this?" "No, it was just me. She wouldn't help me so I did it in my room," Kyle said before Katye could answer. "You march yourself into my bedroom right now!" I growled. "I want you standing in the corner, hands clasped behind your head. We'll be back in one hour! You have some time to think about what you did." I needed an hour to get my temper under control and to let Kyle recover. I wanted to take this opportunity to teach both Kyle and Katye a lesson. I returned in exactly sixty minutes with Katye in tow. I ordered my boy to strip and lay across my lap. Reluctantly, he complied, letting his bound sex rest against the outside of my left thigh. I removed the restraint to allow his sex to hang free for the first time in over a week. With one hand, I held my boy steady by the neck, and with the other, I spanked his bare ass as hard as I could until his cheeks became crimson red. He was screaming with each slap by the time I was done. When I finished, I held him there, caressing his back. I listened to him quietly sob. I spread his plump ass cheeks apart with my right hand and pressed the middle finger of my left hand against his anus. I listened to his sobs turn to a moan. I massaged his opening for a moment before entering him. He gasped and his cock began to grow against my leg. I made sure Katye was positioned well to view his reaction. I pushed one finger in followed by my index finger. Slowly, I massaged his prostrate. It was not nearly as full as it had been an hour ago, but I was still able to coax a fair amount of precum out. "See Katye? Fingering a boy makes him hard. This is how you milk a boy. Ah, there we go. Look at the flow," I said, referring to the free flow of fresh precum from the tip of his over-sized penis head. It dripped in thick long strands before snapping and pooling on my hardwood floor. "It gives him some physical release while still denying him the mental pleasure of an orgasm. In time he'll become used to this form of release. See how it calms him, too?" I stroked his sweat covered hair and upper back. "That's my boy. You're doing great, Kyle." I reached between Kyle's legs and cupped his testicles in the palm of my hand. I massaged his large eggs to help quiet him. I looked Katye in the eye to make sure she understood the enormity of the situation. She seemed to be fully engrossed, standing with her legs crossed and nervously biting the necklace she wore. "Kyle, I have to impress upon you the importance of you not having an orgasm whenever you want it," I explained. I gripped his testicles firmly until his body seemed to freeze under the pressure. I needed to have his full attention. "I understand these require release on an almost daily basis. But you need to be strong enough to overcome the urge to release. And if you can't do it by yourself, then come to me for help. I don't want to have to do this again." "Yes, ma'am," my teenage boy grunted through the pressure in his testicles. "Is the urge too great?" I asked. Kyle sniffled then nodded. "Yeah." I reached a little further and took his penis in my hand. He was almost completely hard. I squeezed it and felt it surge to its full length. "What I'm about to do, I am doing for Katye's edification. Katye, I want you to watch back here as I take him to another orgasm." I pulling on his organ like a farmer would the utter of a cow. I could tell by his gasping and the heaving of his chest that his orgasm was near. "I want you to see how quickly a boy his age can recover with a new load." I stroked him for nearly five minutes without success. His testicles were holding onto their load. I alternated between massaging his testicles roughly and stroking. Finally, he gave up and released his limited load. "A boy can usually recover within an hour with a new load, although it won't be nearly as much. And now he's completely spent. Kyle, hun, why don't you go take a nap. You can finish your chores tomorrow." The spent teenager, who is naturally over the age of eighteen, wearily lifted himself and walked from the room, his long limp cock smacking each thigh as he left the room. He had learned his lesson. KATYE: OMG. By the time I made it back to my room, the insides of my legs were so fucking wet. I got my vibrator out and took myself to two of the best orgasms I had had in ages. I didn't know Kyle could churn up another load that quickly. It wasn't nearly as much as what I got out of him, but it was decent. Mom had me go wake him up two hours later. "Hey, bro, time to wake up," I said quietly as I sat on the edge of his bed. I lifted the bed sheet off his body. I stroked his thigh as he came to. I lifted his balls in his wrinkly ball sac. "Hey, thanks for not ratting me out. It could have been me across her knee." "Yeah, no problem. I needed what you did for me. It was worth it," he responded. "Well, we'll see. You should put on those small boy-shorts she likes. Can't hurt." I watched as my brother stuffed his cock and balls into the tight which square cuts which were barely long enough to reach his inseam. He looked nice. He looked very nice. TINA: I didn't make it to the next body building competition until it had just ended. I guess the awards had just been made and people were dispersing. I watched from a safe distance as Sotoya approached Katye and Kyle. It was then that I realized Kyle had a yellow ribbon attached to his thin waistband. And Katye had a blue ribbon! Sotoya was much more hands on with Kyle this time. She feigned interest in his ribbon, allowing her fingers to dip inside his waistband and graze the base of his shaft. I saw the reaction on my boy's face. He felt it. She held her hand there, even with Katye standing beside her! She was talking intently to him, face to face. She had moved in front of him, blocking my view, but I could tell by Kyle's expression that her hand had most likely moved further inside. He nodded a few times and then swallowed nervously. Katye was biting her lip, listening. Surely, Katye would tell me later what was said. Sotoya's hand reemerged to stroke his arm as she stepped back. It was then that another competitor joined the group. I guessed that it must have been her son. His back was too me but I was surprised to see that he was wearing a beige square cut instead of a bikini. I must admit, it did go well with his black skin tone. He leaned in and gave Katye a kiss. I had seen enough. I needed to break this up. Sotoya's son stepped to the side as I joined the group. Sotoya and I glared at each other. She had her defenses up. Katye tried to diffuse the situation. "Mom, hey, this is Tyrone, Sotoya's son." I was ready to lay into Sotoya but I glanced at Tyrone first. I could not take my eyes off his body. It was so finely sculpted. He was absolutely beautiful as well. Our eyes met, and I felt the connection. There was just something about his eyes...and those lips. My heart thumped nearly out of my chest. I stammered for something to say. I broke the gaze by looking down the rest of his body. I then understood why he didn't wear a bikini. The snake that lived between his legs was much too large for any bikini. While Kyle was well endowed, Tyrone was even larger. Sotoya looked at me with an air of superiority. She had given her son more than I had. I was beat. I didn't bother to lay into her with a tirade. I just left with my two kids, a red face, and a fluttering heart. I made it clear to Katye and Kyle that as long as Sotoya was a judge, they were forbidden from competing. This woman wanted more than to help them win gold. I saw it in her eye. She was dangerous.