“Dear Jake,
Please forgive the informality, be assured I think of you as Sir at all times, but I wanted it to be clear that David Baxter your former boss is writing to you personally to crave forgiveness for my past appalling and inadequate behaviour as your supposed superior and seek to thank you for many kindnesses you are currently extending to me.
Firstly thank you for taking my part in Jane’s sex life. I have always been useless as a lover it is not just that my p_nis is really tiny and that I more often than not have a premature ejaculation during foreplay but I am always too quick and insensitive for a wonderful woman like Jane. My mind always fills with submissive thoughts when I am aroused and this makes it impossible to play a manly role at all. I know you are wonderful with her and I hear you night after night having wonderful sex with her in what was our double bed. How I wish, no long passionately, to be able to do that with her; but please understand that although natural envy and frustration rages inside me when you have her time and time again I know as a true sissy this is what I must endure. To be your cuckold is an honour a just reward. Please believe me when I say I love her and want her, but I know my impotent anger is just a wonderful and proper fuel for her sexual happiness. You must enjoy her even more, secure as you are, that I am denied those pleasures I yearn for.
You know that I have been a secret baby for years but now all that is being exposed to all and sundry, friends, family and the great world outside. My shame is utterly complete. Being forced to dress as a baby is bad enough but I have to behave like one all the time. This reinforces my degradation, I have to appear willing to wet and mess, to wear such ridiculous baby outfits, to lisp and s_ck a dummy, to be changed several times a day; the whole routine degrades me and takes away my manhood and makes me so dependant on you and Jane. Even knowing that such behaviour is so humiliating, and believe me so hard to do, I still undertake wholeheartedly to try my utmost to play the baby sissy role even better in future so you and Jane can derive even more pleasure from my sissy baby status.
As a sissy one of the greatest pleasure of all was to play with my willie when it was safely encased in a soft warm nappy that was often wet. Babyish shameful thoughts ran through my head in luxurious sexy profusion often for hours on end. It was a secret passion, hugely enjoyed and rarely did I lose control and have a premmie. As you know Jane let me continue to play with myself when I was her baby which made all the shame somewhat worthwhile. You have now so rightly stopped that pleasure of mine absolutely. The chastity is totally effective; I cannot get hard, I dare not think sexy thoughts. Simply put it really hurts if I do. You have taken away my sexuality completely. The key is literally in your hands; I only have frustration. As yet I have to learn to come to terms with this, but please believe me when I thank you for being so strict with me. I now have to be a sissy baby cuckold without any sexual pleasure at all. I consol myself with the thought that I can now concentrate on being a pure baby and completely under your and Jane’s control. I am trying to learn that all my willie can do is provide a flow of wee wee into my nappy. I wanted to be a baby well now I am a step nearer to that reality as true babies do not have sexual feelings.
Thank you so much for the sissy baby bonnets. The make me look so babyish and pathetic. I am really ashamed that I have to wear them but at least I can tell everyone that you, Jane’s lover, gave them to me! Of course the very thought of making such an admission makes me squirm with embarrassment.
Please Sir accept this letter as a humble apology for my hopeless inadequate self and be assured I will do all that I can to humiliate myself in front of you, Jane and anyone else you command me to. I shall try as hard as I can to be the best sissy baby possible. You now know that no sexual pleasure comes to me from this.”
Before signing off he called for Emma and asked for her comments before he finished, hoping against hope it would be found adequate.
As she started to read it he watched her face intently. She smiled slowly as she saw how far he was prepared to go; as ever he had humiliated himself more than she thought possible. She hardened her look as she realised she must always be the Dom, the Cruella, the Bitch to her little baby slave.
“Marilyn what about Marilyn your former secretary? You must beg him to show the letter to Marilyn!”
Emma tossed the letter down.
“Don’t think you can get away with silly mistakes like that; corner time NOW!” She shouted.
Crestfallen he toddled to the corner and pressed his nose right in; standing really still in a shamed acceptance of his punishment. Corner time was infantile, humiliating and boring.
He had really hoped that the grovelling letter would satisfy Emma so that she would not bother to continue with the game but clearly she had other ideas. The very idea of Marilyn knowing he was a baby was awful. He was totally in denial that she might know already but the idea of her seeing this grovelling baby rubbish was just so hard to bear. He had always lusted after her; she was a sexy tease and knew it well. Short skirts, hot pants, black stockings were her stock in trade; she was always beautifully turned out and had from the outset had David round her finger. With all the confidence of a loud Essex girl she was one of the characters in the office and regularly used her simple charm and outrageous dress sense to get David round to her way of thinking. She was always sure to ask him for favours when she had the sexiest outfit on. David’s feebleness with her lowered his standing in the office, a fact he was ineffectually aware of, but seeming incapable of doing anything about it.
David secretly longed for her in a submissive dog panting way, summoning up images of her standing proud in stockings and in scanty briefs as a teasing dominant or a nanny berating him for wetting his nappy when he played with himself secretly. He half thought that she read his submissive thoughts as her behaviour towards him became more lewd and condescending over the months she worked for him. Now though he did not want to think of bringing this fantasy to reality, not least as she was one of those people who knew everyone and more besides, knew all the gossip, and was the centre of the office if not the industry grapevine. His baby secret would be well and truly out if she knew about it. He could not imagine her reading such a letter.
From deep in the corner he started to whine;
"Pleath Nanny not that Pleath pleath nanny I will be a thpethial thpethial baby for you, take me out and change me in public but pleath don make me wite that. Mummy doethnt want her to know."
Emma loved it! A grown man dressed in a sissy baby outfit, standing in the corner, was pleading and begging with her inviting more humiliation to be heaped on him. Suddenly a further inspiration hit her; she knew Jane’s mind in this and a nasty little trick occurred to her.
“So you think Mummy will object and I am wrong do you? Well let’s ask her shall we? Let’s see what she says. If I am wrong Jake will not to show it to Marilyn and you can have ice cream for tea but if you are wrong you have been both naughty and cheeky and will have to be punished severely. So you will have to ask Jake tonight to take down your plastic pants, take off your nappy and put you across his knee and smack your little bare botty till it really hurts’; understand?
Deep in the corner David flushed even redder at the thought of Jake spanking him, the shame of it let alone the pain sent shudders down his spine. But he did not really understand how far Jane was prepared to go, what was to him a seething humiliation involving Marilyn was just a part of the fun for Jane. Especially as she knew that Jake had told her quite a bit anyway.
Emma was already keying in Jane’s number on her mobile.
“Hi Jane, no don’t worry no problems, he is writing that letter to Jake and has a question to ask you, here he is” punching the loudspeaker key she held the phone close to his face which remained pressed in the corner.
“Helwo Mummy”
Hello sweetie are you OK. Being good?
Jutht in the corner for a lickle while coz I got it wong”
“Dear dear you never Learn do you, what do you want to ask darling?”
“Mummy Mummy Nanny saith that I mutht ask Uncle Jake to thow the letter to Marilyn.pleasth Mummy don’t thay he can pleath Mummy, Marilyn wiwll thow it to evferyone and evferyone will know I am a thissy Baba; pleath Mummy pleath thay no.”
There was a pause; Jane felt a surge of lust. She realised how much David would hate Marilyn knowing about him. Frankly she thought Marilyn was just a coc-ky sexy tart, but David had always had this thing about her, now he would feel perhaps even more shame than he had when he met Jake for the first time. Oh what a lovely sexy thought, the greater David’s shame and embarrassment the more she liked it. It would turn Jake on as well; another night of pure sex heaven was in prospect.
“Of course you should have Jake show the letter to her you know how you liked her why don’t you want her to know you are my sissy baby?
Peath mummy I tho athamed!
Jane heard the wail and could not stop herself from pressing her soft, now wet quim harder onto her chair
“Silly baby you know I am not interested in how ashamed you feel. You should have thought of that when you started seeing those nasty tarts in New York; by the way I hope your letter to Jake explains what you used to be up to on your business trips.” Now pass the phone back to Nanny.
“Emma you heard all that?”
“Oh yes Jane I had already said as much but he insisted on talking to you even after I told him it was disobedient to query my judgement, so he will have to punished again so that he learns to do as I say. I thought it might be a good idea to have Jake smack his bare botty tonight?
Jane giggled loudly, “You are such a strict nanny aren’t you?”
“Fine Emma but I have another idea; get David to write and ask for his spanking both for misbehaving whilst he was Jake’s boss and also for today’s indiscretion. You know a real grovelling letter that will amuse Marilyn as well! Get him to apologise for taking all that baby stuff with him on business trips. I assume the loudspeaker is still on and he can hear me?”
Emma looked at the figure tight in the corner, it seemed to shrivel.
“Oh yes he can hear you all right”
“Good I will get Jake to come round early tomorrow so you can watch, He has been itching to redden David’s bum for ages. I expect David has secretly longed for it as well. So that will make him happy, well until the second smack then he will start to regret it for the rest. I think Jake has more stamina than either of us and he is certainly stronger so it should be rather amusing.
Bye Emma I must rush, Bye Sophie sweetie you have something to look forward to now for nearly two whole days! Love you” she cried.
David started to sob; real tears ran down his face. Write all that to Jake, Marylyn was to see the letter and then a hard horrid hurtful spanking from Jake as well; he knew he would let himself down completely by hollering and shouting, begging for forgiveness. What could be worse? Of course a whole lot of things and deep deep down he knew he would discover them before Jane had finished with him.
Emma prodded him to make changes here and there and add the paragraphs that Jane wanted. Eventually the letter was finished; it was quite a masterpiece in crawling self abasement!
“My Dear Jake,
Please forgive the informality, be assured I think of you most respectfully as Sir at all times, but I wanted it to be clear that David Baxter your former boss is writing to you personally to crave forgiveness for my appalling and inadequate behaviour as your supposed superior at Davenport Systems Ltd and to thank you for many kindnesses you are currently extending to me.
You must have wandered why I appeared so tired on many of our foreign business trips, the reason was that I spent most nights in the hands of some professional nanny being babied, dressed up and beaten or caned. I was always worried that I would smell of urine as I had always wet my nappy the night before. I have sat through many a meeting with a very sore bottom either with nappy rash or from a beating and sometimes both. I also know you were always irritated that I had hold luggage that delayed our way through airports whilst you managed with a small carry on. This was because I carried a full range of nappies, plastic pants, nighties, sweet little dresses and other baby paraphernalia in my bags. My nightmare was that somehow you would become aware of them and my shameful secret exposed; of course you are now to an extent I could never have imagined back then.
I think you will agree that a simple letter of apology is not nearly adequate expression of my remorse. Please be so kind to give me a really hard bare bottom spanking across your knee on Wednesday evening in front of Jane and my Nanny Emma. The thought of your strong masculine hands slapping my lily white baby flesh makes me cringe with shame and humiliation but I know I richly deserve it. Please make it really hurt, ignore my cries; just think to yourself as I shout and holler how much I deserve to be soundly spanked.
I really want to thank you for taking over my role in Jane’s sex life. I have always been useless as a lover; it is not just that my p_nis is really tiny and that I more often than not have a premature ejaculation during foreplay but I was always too c-umbersome, too quick and completely insensitive and unimaginative for a wonderful woman like Jane. My mind always fills with submissive thoughts when I am aroused and this makes it impossible to play a manly role at all. I know you are wonderful with her and night after night you are having wonderful sex with her in what was our double bed. How I wish, no long passionately, to be able to do that with her; but please understand, that although natural envy and frustration rages inside me when you have her time and time again, I know this is what a true sissy must endure. To be your cuckold is a very great honour. Please believe me when I say I love her and want her, but I know my impotent anger is just a wonderful and proper fuel for her sexual happiness. You must enjoy her even more, secure as you are, that I am denied the marital pleasures I yearn for.
You know that I have been a secret baby for years but now all that is being exposed to all and sundry, friends, family and the great world outside. My shame is utterly complete. Being forced to dress as a baby girl is bad enough but you know I have to behave like one all the time. This reinforces my lowly state. I have to appear completely content to wet and mess myself and suffer the indignity of being changed several times a day and I know Jane expects me to eventually lose what little control is left. I must enjoy and be proud to wear cute pretty baby clothes appropriate for a toddler girl that look utterly ridiculous on an adult, to lisp like a baby when I talk and s_ck a dummy; the whole routine degrades me and takes away my manhood and makes me so dependant on you and Jane. Even knowing that such behaviour is so humiliating, and believe me so hard to do, I still undertake wholeheartedly to try my utmost to play the baby sissy role even better in future so you and Jane can derive even more pleasure from my sissy baby status.
As a sissy one of the greatest pleasure of all was to play with my willie when it was safely encased in a soft warm nappy that was often wet. Babyish shameful thoughts ran through my head in luxurious sexy profusion often for hours on end. It was a secret passion, hugely enjoyed and rarely did I lose control and have a premmie. As you know Jane let me continue to play with myself when I was her baby which made all the shame somewhat worthwhile. You have now so rightly stopped that pleasure absolutely. The new chastity is totally effective; I cannot get hard; I dare not think sexy thoughts. Simply put it really hurts if I do. You have taken away my sexuality completely. The key is literally in your hands; I only have frustration. As yet I have to learn to come to terms with this, but please believe me when I thank you for being so strict with me. I now have to be a sissy baby cuckold without any sexual pleasure at all. I consol myself with the thought that I can now concentrate on being a pure baby and completely under your and Jane’s control. I am trying to learn that all my willie can do is provide a flow of wee wee into my nappy. I wanted to be a baby well now I am a step nearer to that reality as true babies do not have sexual feelings.
Thank you so much for the sissy baby bonnets. The make me look so babyish and pathetic. I am really ashamed that I have to wear them but at least I can tell everyone that you, Jane’s lover, gave them to me! Of course, as I write this, the very thought of making such an admission makes me squirm with embarrassment.
Please Sir accept this letter as a humble apology for my hopeless inadequate self and be assured I will do all that I can to humiliate myself in front of you, Jane and anyone else you command me to. I shall try as hard as I can to be the best sissy baby possible. You are assured that no sexual pleasure comes to me from this.
Please also show this letter to Marilyn as I feel that she should know my true nature and what a pathetic sissy baby she worked for. I apologise to her unreservedly for all the lustful glances I gave her, the naughty disgusting thoughts I entertained about her underwear especially her panties and the fact that I used to do pathetic spurties into a nappy thinking about her. I hope she finds this confession a great laugh. No doubt she will tell all her friends; I cringe at this thought but she has every right to do so.
Please always call me by my baby name of Sophie in future.
Most respectfully yours
David Baxter aka Sophie”
David felt so miserable sitting at the cramped uncomfortable desk but was relieved that at last after several attempts the letter writing ordeal was over. Its contents did not bear thinking about and he kept on shuddering at the thought of Marilyn reading it but at least Emma seemed satisfied with it.
Emma soon had him the high chair and was feeding him mashed vegetables with lots of brown rice; this will keep you good and regular she thought! As she shovelled in the food quickly as they were starting to run late she began the preparation for the visit to Marie’s and the really humiliating session at the hairdressers she had planned.