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