tagBDSMM.I.L.F. vs Stud Ch. 03

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


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


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.

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