Spanking habits
I have liked being spanked for quite a time. Not to the extent of real pain, but a stinging bottom and red cheeks are very acceptable. For a while I was seeing a lady who did exactly this and then provided a happy ending.
She loved high heels and fully fashioned nylons and I so enjoyed her pulling up her skirt and then being put across those nylons to have my bottom spanked.
But I now see my Mistres s on a reasonably regular basis and felt it was not appropriate to see another lady. But there are some occasions when my Mistres s will not be available-holidays or working.
So I broached the possibility of seeing this lady to my Mistres s.
She has agreed so long as I get her permission, for each visit and take with me a letter from my Mistres s. This explains the basis on which I am permitted to be spanked and pleasured. It also requests that this lady calls me by my femme name-jane. I attach a portion of it below.
"Dear Annie, (I do hope you do not mind me addressing you in this familiar manner)
You may know me as Jane’s ********, Mistres s Natalie. I am grateful for you using her feminine name, as I gather you were not aware of it previously.
I am writing this note to explain my intentions regarding how I am training Jane.
I think that you have known her longer than I, as our relationship started in 2017, when she visited me and my partner, who also cross-dresses, for a mutual dressing session. This proved most enjoyable and my partner is content that Jane visits me for erotic lesbian encounters, with her submitting to my dominance.
We have visited coffee shops, garden centres and many ladies dress shops, with Jane dressed completely en femme. Jane finds this very erotically stimulating as I do myself.
I enjoy dominating her and have her completely dependent on me. Our sessions do end with a sexual conclusion, usually involving me penetrating her with a double ended dildo. She always adopts a submissive and female position.
Now, I only see Jane, no one else and I am attempting to assist her in her feminisation journey. As an example I have let her assist me in massaging a male friend, concluding in Jane and me giving him a happy ending.
I am conscious that Jane is thinking about what it would be like to have anal sex, and have been warning her about what that might lead to and the possibility of it endangering her marriage. However, if she really wishes to try, then the friend I mentioned could assist and Jane could be gently introduced and able to opt out, with me being present, to ease her in, as it were!
Now, as to lingerie training, Jane was turned on by black lacey lingerie and black stockings.
However, I do believe that this obsession with very sexy underwear, should be countered, as most women do not wish to be dressed in such a manner all the time. I am very conscious of her approach to lingerie and, indeed, the words she uses to describe each item. She likes the word “panties” so I am beginning to counter this by the use of “knickers” and indeed “nylons” rather than “stockings”.
To that end I am now, sometimes, dressing in white lingerie and tan stockings when she visits.
As I am deliberately developing a foot fetish in her, she will contentedly suck on my white or tan stockings for a few minutes, as soon as she enters my house. I am occasionally dressing Jane in a similar manner so that she becomes aroused by these day to day items, just as much as lacey and black ones.
In particular I am getting her excited and aroused whilst wearing cotton full panties. I ensure that she orgas ms into the pantie itself and this is proving very successful.
It is this that I would very much appreciate your continuing. I will permit her to travel in red nylon/lacey panties and black stockings, but I would very much like you to get her to change into her cotton ones and tan stockings to receive your delightful spanking.
And when you wa nk her, please keep her panties covering her clitty-and if you could take a photo of her soiling her panties and her before and after changing her lingerie.
For your information and amusement, I have included a sheet of photos of Jane when she is en femme with me, so that you can understand the nature of our relationship.
Kindest regards, and warmest thanks Mistres s Natalie"
I have liked being spanked for quite a time. Not to the extent of real pain, but a stinging bottom and red cheeks are very acceptable. For a while I was seeing a lady who did exactly this and then provided a happy ending.
She loved high heels and fully fashioned nylons and I so enjoyed her pulling up her skirt and then being put across those nylons to have my bottom spanked.
But I now see my Mistres s on a reasonably regular basis and felt it was not appropriate to see another lady. But there are some occasions when my Mistres s will not be available-holidays or working.
So I broached the possibility of seeing this lady to my Mistres s.
She has agreed so long as I get her permission, for each visit and take with me a letter from my Mistres s. This explains the basis on which I am permitted to be spanked and pleasured. It also requests that this lady calls me by my femme name-jane. I attach a portion of it below.
"Dear Annie, (I do hope you do not mind me addressing you in this familiar manner)
You may know me as Jane’s ********, Mistres s Natalie. I am grateful for you using her feminine name, as I gather you were not aware of it previously.
I am writing this note to explain my intentions regarding how I am training Jane.
I think that you have known her longer than I, as our relationship started in 2017, when she visited me and my partner, who also cross-dresses, for a mutual dressing session. This proved most enjoyable and my partner is content that Jane visits me for erotic lesbian encounters, with her submitting to my dominance.
We have visited coffee shops, garden centres and many ladies dress shops, with Jane dressed completely en femme. Jane finds this very erotically stimulating as I do myself.
I enjoy dominating her and have her completely dependent on me. Our sessions do end with a sexual conclusion, usually involving me penetrating her with a double ended dildo. She always adopts a submissive and female position.
Now, I only see Jane, no one else and I am attempting to assist her in her feminisation journey. As an example I have let her assist me in massaging a male friend, concluding in Jane and me giving him a happy ending.
I am conscious that Jane is thinking about what it would be like to have anal sex, and have been warning her about what that might lead to and the possibility of it endangering her marriage. However, if she really wishes to try, then the friend I mentioned could assist and Jane could be gently introduced and able to opt out, with me being present, to ease her in, as it were!
Now, as to lingerie training, Jane was turned on by black lacey lingerie and black stockings.
However, I do believe that this obsession with very sexy underwear, should be countered, as most women do not wish to be dressed in such a manner all the time. I am very conscious of her approach to lingerie and, indeed, the words she uses to describe each item. She likes the word “panties” so I am beginning to counter this by the use of “knickers” and indeed “nylons” rather than “stockings”.
To that end I am now, sometimes, dressing in white lingerie and tan stockings when she visits.
As I am deliberately developing a foot fetish in her, she will contentedly suck on my white or tan stockings for a few minutes, as soon as she enters my house. I am occasionally dressing Jane in a similar manner so that she becomes aroused by these day to day items, just as much as lacey and black ones.
In particular I am getting her excited and aroused whilst wearing cotton full panties. I ensure that she orgas ms into the pantie itself and this is proving very successful.
It is this that I would very much appreciate your continuing. I will permit her to travel in red nylon/lacey panties and black stockings, but I would very much like you to get her to change into her cotton ones and tan stockings to receive your delightful spanking.
And when you wa nk her, please keep her panties covering her clitty-and if you could take a photo of her soiling her panties and her before and after changing her lingerie.
For your information and amusement, I have included a sheet of photos of Jane when she is en femme with me, so that you can understand the nature of our relationship.
Kindest regards, and warmest thanks Mistres s Natalie"
Spanking habits
I have liked being spanked for quite a time. Not to the extent of real pain, but a stinging bottom and red cheeks are very acceptable. For a while I was seeing a lady who did exactly this and then provided a happy ending.
She loved high heels and fully fashioned nylons and I so enjoyed her pulling up her skirt and then being put across those nylons to have my bottom spanked.
But I now see my Mistres s on a reasonably regular basis and felt it was not appropriate to see another lady. But there are some occasions when my Mistres s will not be available-holidays or working.
So I broached the possibility of seeing this lady to my Mistres s.
She has agreed so long as I get her permission, for each visit and take with me a letter from my Mistres s. This explains the basis on which I am permitted to be spanked and pleasured. It also requests that this lady calls me by my femme name-jane. I attach a portion of it below.
"Dear Annie, (I do hope you do not mind me addressing you in this familiar manner)
You may know me as Jane’s Mistress, Mistres s Natalie. I am grateful for you using her feminine name, as I gather you were not aware of it previously.
I am writing this note to explain my intentions regarding how I am training Jane.
I think that you have known her longer than I, as our relationship started in 2017, when she visited me and my partner, who also cross-dresses, for a mutual dressing session. This proved most enjoyable and my partner is content that Jane visits me for erotic lesbian encounters, with her submitting to my dominance.
We have visited coffee shops, garden centres and many ladies dress shops, with Jane dressed completely en femme. Jane finds this very erotically stimulating as I do myself.
I enjoy dominating her and have her completely dependent on me. Our sessions do end with a sexual conclusion, usually involving me penetrating her with a double ended dildo. She always adopts a submissive and female position.
Now, I only see Jane, no one else and I am attempting to assist her in her feminisation journey. As an example I have let her assist me in massaging a male friend, concluding in Jane and me giving him a happy ending.
I am conscious that Jane is thinking about what it would be like to have anal sex, and have been warning her about what that might lead to and the possibility of it endangering her marriage. However, if she really wishes to try, then the friend I mentioned could assist and Jane could be gently introduced and able to opt out, with me being present, to ease her in, as it were!
Now, as to lingerie training, Jane was turned on by black lacey lingerie and black stockings.
However, I do believe that this obsession with very sexy underwear, should be countered, as most women do not wish to be dressed in such a manner all the time. I am very conscious of her approach to lingerie and, indeed, the words she uses to describe each item. She likes the word “panties” so I am beginning to counter this by the use of “knickers” and indeed “nylons” rather than “stockings”.
To that end I am now, sometimes, dressing in white lingerie and tan stockings when she visits.
As I am deliberately developing a foot fetish in her, she will contentedly suck on my white or tan stockings for a few minutes, as soon as she enters my house. I am occasionally dressing Jane in a similar manner so that she becomes aroused by these day to day items, just as much as lacey and black ones.
In particular I am getting her excited and aroused whilst wearing cotton full panties. I ensure that she orgas ms into the pantie itself and this is proving very successful.
It is this that I would very much appreciate your continuing. I will permit her to travel in red nylon/lacey panties and black stockings, but I would very much like you to get her to change into her cotton ones and tan stockings to receive your delightful spanking.
And when you wa nk her, please keep her panties covering her clitty-and if you could take a photo of her soiling her panties and her before and after changing her lingerie.
For your information and amusement, I have included a sheet of photos of Jane when she is en femme with me, so that you can understand the nature of our relationship.
Kindest regards, and warmest thanks Mistres s Natalie"
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