From Alpha to Sissy Pt. 01

This is my story and is also published elsewhere.

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Dear Mistress,

First of all let me thank you for potentially giving me the opportunity, with your help, guidance, humiliation and discipline, to fully realise my core nature of being a cuckolded, sissy faggot worthless to any woman sexually, but rather a loving, supportive partner in anything a woman chooses.

To truly understand that my small penis and beta male ways are not suitable for sexually satisfying any woman, but rather to be locked in chastity and that the only way I could please a woman sexually is by supporting her to find a real man capable of giving her the sexual satisfaction I can't. That only my oral skills should be made proficient to offer her some release when her lover is unavailable or to orally clean her vagina after her lover has deposited his seed inside her. And accept that her humiliation of me (privately or publicly), her pegging me, her inflicting pain on me and her disciplining me are all ways I can please her.

And to learn to appreciate that, whilst I am straight and will always find women sexually attractive, because I'm unable to satisfy a woman then my own sexual pleasure will only come from my being anally penetrated by dildo, strap-on and a real man's penis and will be turned into a sissy faggot so that I concentrate all my sexual desires and fantasies around cock not women. Any masturbation will only be to gay or sissy porn, or femdom porn so that I associate my sexual pleasure with being used by men or dominant females; or masturbating as I watch my Mistress being satisfied by a real man as I'm cuckolded.

To accept that I will be milked, not masturbated (unless in above instance), to release any build up of semen, thus denying me any sexual satisfaction from orgasm, and that I must always lick up and eat any semen I produce to ensure I grow to love the taste of a man's ejaculate for those times when I will either be eating creampies from my Mistress's body/pussy/ass or sucking any men who require it of me to orgasm.

To learn to take corporal punishment, accept CBT (cock and ball torture) and endure any punished my Mistress requires of me either for my education in obedience or for the pleasure of my Mistress.

Now I appreciate thst whilst this isn't a conclusive or definitive summary of my needs it is rather comprehensive so, with that in mind and, as requested, the following gives some background and experiences that have led me to this desire and need to be cuckolded, dominated,humiliated and sissified into an obedient, cock craving, pussy whipped pathetic beta male. And, at the end, I'll give you an insight into the kind of relationship I'd like to have if I was lucky enough to meet a woman.

Until my marriage (aged 27) I was a sexual active Alpha male. I took great joy in pleasing women sexually and had no complaints in that department. Indeed I was often complimented not only on my ability to pleasure women, but to ensure they were sexually satisfied before I gained my own release. With each subsequent woman I would endeavour to be the best lover they had experienced and was often told that I was. I took pride in knowing I could please a woman and my ability to control my own orgasms helped enormously in ensuring I wasn't the typical '5 minute wonder'.

Then I met and eventually married a woman and, due to my own stupidity, things began to change. You see I was found out having had a short-lived affair. Without boring you with the details, suffice to say my wife wasn't pleased and gave me an ultimatum. I was to ask my best friend if he would like to have sex with my wife or the marriage was over.

Julie, my wife, had fancied Pete, my best friend, for as long as she'd known me and we both knew Pete fancied my wife. Julie said she could only forgive my indiscretion if she could 'even the playing field' - her words, and that as she fancied Pete and he fancied her he would be the ideal person to 'give you a taste of your own medicine'. Again, her words.

It wasn't an easy decision I had to make, lose my marriage (we had a child at that time) or ask my best mate to 'please' have sex with my wife. What complicated things further was the fact Pete and I, apart from being best friends since age 11, were also business partners - we worked with each other most days as well as drank together for an hour or so after work. However, I assumed Pete would say 'no' if I asked him anyway. It's one thing to fancy your best mate's wife, quite another to sleep with her - even if asked by her husband. I was sure our friendship meant more than a tumble between the sheets.

Unbeknownst to me at the time however, my wife had already spoken with Pete regarding the situation and had convinced him that it was my idea they should have sex with each other. I (much) later found out from Pete that Julie had visited him at our business premises when I was taking a day off (due to a tummy bug) and had asked him if he would be ok having sex with her because she wanted to fullfil a fantasy of mine - that of watching my wife being fucked by my best friend. I hadn't had any such fantasies of course, but Pete didn't know that. He told me later that my wife had convinced him it was my idea after she told him that I would not only ask him to fuck her, but also say 'please' when I did. And, to reassure him that my wife was ok with it too, she had given my best friend a blow job right there and then in my office.

Anyway, to cut a long story short, I did, with my wife present (at her insistence), ask my best friend if he would 'please have sex with my wife'. I didn't want our marriage to end and felt confident he would say no. He didn't. Instead he asked me why. Julie had told me to say to Pete it was my biggest fantasy to watch her with another man and that he would be the safest choice, being best friends etc. When I told Pete this he said I was a bit of a pervert, but that he'd love to fuck my wife, if she didn't mind. Julie, sitting between us at the time, said if it's what I really wanted then she would be happy to help fulfill my fantasy.

It wasn't my fantasy! I didn't want to watch! It was my wife's way of getting back at me for having a fling, but I couldn't say that to my best friend.

Pete, however, said he'd need to fuck her alone first before letting me watch so that he wouldn't be put off with my watching as he'd never had sex with another man present before. Before I could object, my wife said that would fine as she too felt awkward having sex for the first time with another man, let alone in front of her husband. I said I'd cut this short so, in summary, they ended up in bed together 15 minutes later and continued to have sex with each other for the next 3 years. I watched once. It was enough for me. Pete was considerably much better endowed than I was and Julie loved the sex with him.

During those 3 years my wife became more dominant towards me. She and my best friend had sex at least 3 times a week, more often 5 or 6 times a week, and my own sex life was eventually reduced to masturbating as they made love in our bed. Initially Julie and I still had sex, but only a few months into her affair with Pete I was 'allowed' only to have sex with my wife after she had been satisfied by Pete. I grew used to 'sloppy seconds' and was encouraged to orgasm quickly as Julie grew less interested in sex with me.

Pete eventually found a partner of his own and the affair ended. I sold my half of the business to him at this point - our friendship had waned during the years he was sexing my wife and I needed to try and put it behind me. My wife, however, was really upset the affair was over. We did try to resume normal sexual relations between us, but I had been conditioned to orgasm quickly over the last two years and, combined with the knowledge my wife preferred sex with my best friend than with me, I could find the motivation to try to please her. Her constant reminders of how much she missed Pete's large cock didn't help either. Soon our sex life consisted of me furiously fucking her for a couple of minutes then bringing her to orgasm orally. This was my initiation into eating my own cum. I didn't know the term cuckolding then. That knowledge came a few months later.

Then Andy came on the scene. It was only after my wife and him having an affair for 8 months that I eventually found out. Julie had become careless, or uncaring, because one evening, after she had just come home from a 'girl's night out', she said she felt horny. This was new to me since Pete was no longer on the scene. Laying on the settee she pulled her knickers to one side and told me to 'get in and hurry up and cum' so that I would then bring her to orgasm orally. As sex had become infrequent I didn't argue and, as was by now the norm, my wife just lay on her back, spread her legs and put her arms by her side as l entered her. I commented on how incredibly wet she was, unusual since she only got wet when I went down on her and she'd not felt this wet since my sloppy seconds sex after Pete had cum inside her many months previously. Julie said I should count myself lucky and to hurry up and cum. I tried to, but she was so wet and loose that, when I hadn't cum after the usual couple of minutes, she started to urge me on saying hadn't I cum yet? and to hurry as she needed to cum badly. Her impatience, combined with the lack of any friction due to her wetness, dampened my ardour so I faked my own orgasm.

Thinking I had cum my wife quickly pushed me back on the floor and straddled my face, something she had never done before. Usually I would just withdraw, slide down the bed or settee, and bury my face in her sex. This was new. Julie was sqatting over my face, her hands on the settee as she looked down at me between her spread legs. She then said I must have cum a lot because she felt flooded and to open wide to ensure my mess went in my mouth not on the carpet. Although I knew I hadn't orgasmed at all, let alone 'cum a lot', that didn't stop a torrent of semen pour out of my wife's pussy and into my mouth. It certainly wasn't mine. I've never produced the amount of semen that I was now swallowing and it tasted different too. I knew Julie was watching between her legs as she said she never knew how much it would turn her on to watch cum dripping from her into my mouth and seeing me swallow it all. Then she did something else she hadn't done before - gripping the sides of my head she pulled my face into her pussy and orgasmed without any stimulation from me.

This started a new chapter in our sex lives. I hadn't let my wife know I knew it wasn't my ejaculate I had just eaten. I don't know why I didn't tell her, maybe I feared the consequences or maybe it was because Julie had stated it was the best orgasm I had ever given her. Regardless, things began to change between us.

You may be wondering why I allowed my wife to have an affair with my best friend for 3 years when my own, short-lived affair lasted only a couple of weeks. Well after the first few weeks of her affair with Pete I asked her if she hadn't paid me back for my indiscretion yet. In reply she asked me why I had stopped 'fucking someone behind her back'. I answered that I realised it was a mistake and that it was simply an itch I had to scratch and the excitement of sex with someone else that had enabled me to act so foolishly. As soon as the novelty wore off I stopped. Julie responded that as soon as she realises having sex with another man is 'a mistake' and the 'novelty' wears off then she too will stop. Until then, like I had done, she will continue to enjoy the 'excitement' and let Pete 'scatch' HER 'itch'. Well, as you now, it was three years before Pete ended the affair and I assumed that was that.

However, after eating another man's cum from my wife over a year after that affair ended I knew my wife hadn't 'realised her mistake' yet. I also knew she had taken my silent acquiescence of that event as a green flag because our sex life changed, perfunctory as it already was.

Two nights after the event described earlier my wife came home after 'another girls night out' and said she needed my oral skills. But instead of laying on her back as was the normal routine she asked me to lay on my back on the floor. Thinking she was going to sit on my cock I lay back unzipping my jeans as she removed her knickers. Instead, Julie knelt, straddled my face and, taking my cock in her hand began masturbating me. I didn't have time to say anything because, as I looked at her pussy inches from my face, I only had seconds to register it was obvious she'd very recently had sex before cum started to ooze from her. Looking at me between her thighs she said 'open wide' and furiously masturbated me and I had little choice but to swallow the copious amount of another man's cum drooling out of my wife's pussy. As the final large globule of cum slid into my mouth I orgasmed, my wife masturbating me expertly. Immediately she sat on my face and ground her sex against me until she too climaxed.

This became the 'new norm' for my sex life with my wife. I rarely had sexual intercourse with her after that time, instead she would masturbate me, or, as became more frequent, I would masturbate myself as she straddled my face after having sex with Andy. Julie would, more and more often, come home after her 5 nights a week visits to the gym and declare she was to tired after her workout to masturbate me. She would simply say, "It's time for your cream clean and cum Chris", and I would assume the position on my back as she either squatted or knelt over my face, pull the crotch of her leotard to one side and literally feed me another man's cum from her pussy as I masturbated myself. She didn't even bother with her own orgasm anymore, simply watched as I licked her pussy clean, encouraging me to cum quickly as she wanted a shower.

I didn't know his name was Andy until a year or so later. Apart from our sex life, things continued as in any other marriage. Julie was becoming more dominant in any decision making - or was I simply becoming more acquiescent? Probably both in hindsight. But we trundled along, now with two children in our little family. Then, one evening (it was my 35th birthday), my wife initiated sex. Not the usual 'straddle my face as I masturbated' sex, but the 'wine, dine and bed me' sex of our earlier years together.

Julie was like her old self with me that evening. She cooked a lovely, light meal for us, played some of our favourite songs and was really very romantic. She asked me if I would like to make love to her like we did "before I found out about your indiscretion" - her words. I said I would love to and, taking my hand, she led me to our bedroom. As we kissed we undressed each other and my wife looked fantastic in a new set of lingerie I'd never seen before; her visits to the gym had kept her in really good shape. I was already erect when Julie released my penis from my boxer shorts and, sitting me on the edge of the bed knelt on the floor in front of me and slowly masturbated me as she started to speak.

Mistress, I realize this email is already rather long and I am conscious of taking up your valuable time. I've tried to be concise, however it's not easy compressing into a summary my journey to contacting you.

If you would like to hear (in similar summary) the conversation that would, ultimately, result in the end of my marriage and to bring you up to date with where I am now and what I hope for the future please let me know.

Yours respectfully

....