The transformation of my husband into my perfect sissy

Posted by: Madam Sadie in Chastity on Print 

A number of people have asked how and why I transformed my husband into a sissy etc and so I have outlined here some of how and what happed but will elaborate on specific areas another time.

I have a sister whom my parents adopted as a baby when I was two years old. Our parents were very liberal in our upbringing and encouraged us to explore our sexuality. This was mainly due to our mother being a gynaecologist and therapist and my father a GP and psychologist.

My husband on the other hand had a stricter upbringing due in part that his father often worked away from home and therefore his mother took charge of him and his sister.

My first lesbian experience was when my sister and I were travelling through Europe on holiday and one cold night we found ourselves stuck in a flea bitten Hotel where each of our single beds only had one blanket each. Being sisters we decided we would be warmer if we both slept in the same bed with the two blankets on top.

I don't recall who kissed who first, it just happened, but the kissing became more passionate and soon we were fondling and exploring each other's body and ended satisfying each other orally in a 69.

I mention all of this to give you a background as to how the feminisation of my husband started.

Since that first instance I have had a number of sexual relationships with both male and females as has my sister who although now married still does and my sister and I still have sex together, sometimes this will be a threesome with her husband or other men or women.

My boyfriend and I (now my husband) had a flat in Chelsea and as he often travelled, my sister would come over and stay when he was away.

One day though he returned early and thought his luck was in as he would be in for a threesome with my sister and I as he had done before.

However, we told him that we had planned a girly night out and so he was not included.

For the rest of the day he mopped around whinging and whining as to why he could not join us.

In the end my sister suggested he could join us by being an honorary girl for the night but that this meant he would have to be dressed as one.

Believing he would get to have sex, he agreed.

We dressed him up in my underwear and padded the bra out with cotton wool, then we put him a short skirt and blouse and fitted a fancy dress wig I had on his head. The only problem was shoes as we both had smaller feet, but succeeded in the end by squashing his feet into a pair of sling backs. We then painted his nails, fitted him with false eyelashes and layered on foundation cream and makeup until we were confident he would pass as a girl so long as it wasn't too light or no one got too near.

But the problem was the bulge in the front of his skirt making it obvious he had an appendage a girl didn't have. So I told him to take his panties off and go for a pee whilst I went to the freezer and wrapped some ice in a towel, which I applied around his cock. Then once it had shrivelled up, I quickly tied and wrapped string around his cock and balls till I had a tight neat little package and once he pulled his panties up again the bulge had disappeared.

So now we had our honorary girl and the three of us could go to the pub as planned.

Luckily it was night time and only a short walk to the pub as he had problems keeping his balance and obviously the shoes were painfully uncomfortable. But once in the pub we quickly ushered him into a corner booth and made sure we would be able to sit either side of him.

As the pub filled up and people began to drink more, we were approached by two men intent on trying to chat us up. When they asked for our names, my sister being quick thinking responded for my boyfriend, saying her name is Chloe (since then the name has stayed) and that she had a throat infection so was unable to speak. Fortunately they weren't interested in Chloe and I can't blame them as she wasn't the prettiest girl on the block.

Later in the bar I slid my hand up his skirt to fondle his restricted cock, only to find my sisters hand already there. It was obvious this was causing him a great deal of discomfort which only encouraged us to do it more.

Eventually last orders were called and we made our way back to the flat. Obviously the walk back for him was even harder with his now restricted erection.

Once back, he asked me to undo the string, but my sister and I responded that he was still our honouree girl and this was not possible. But we told him he could take off his clothing and put on a nightie I got out for him whilst my sister and I slid out of our clothes. After some more drinks, all three of us retired to bed and my sister and I started playing with each other. He again asked to be untied  so he could join in, but we told him that girls don't have cocks and so he had to pleasure us with his mouth.

He brought us both off that night and had obviously hoped we would reciprocate but instead we just turned over and went to sleep.

After my sister had left early the next morning, I untied his cock and he immediately rushed to the toilet where he peed for ages before returning to the bedroom where I rewarded him and we had the most fantastic sex.

Before and after our marriage we would often reinact that time, sometimes with my sister and sometimes without. But I did get him a CB2000 to replace the string.

After our marriage we joined a number of swinging clubs and continued to have sex with other partners and in threesomes or foursomes. The only part of this that miffed me was when another woman was involved, he would expect me to orally pleasure them but if another man was involved he wouldn't even touch them. However the sex was great and the only stipulation was that we would always tell one another about the sex and it would remain casual sex with others.

As time went by my business grew and grew and as I was making more than enough money and my husband was getting tired of travelling, we decided he should stay at home and look after the house etc.

All was fine for the first couple of months, but gradually I noticed he was often tired when I got home and not only were none of the chores done but he appeared to be going off me. So I got a private detective to watch him for a week and found that he was seeing another woman each day. I confronted him with the evidence and he admitted he was having an affair with her but tried to blame me. I was furious at this and we had a flaming row. The outcome was he still loved me and begged for my forgiveness. I told him I would forgive him, but in order for him to regain my trust he was to remain in the house and to insure this I locked away all his clothes and he had to be dressed as a woman instead. I also locked him in his CB2000.

This worked fine as he was now attentive to all my needs and the housework was always done as being dressed as a woman he was unable to leave the house. Also our sex life was fantastic.

However, after time I missed having sex with other men and women and told him I would start going out again. He of course assumed he could do likewise, but I told him he still hadn't regained my trust and so would have to remain at home.

Of course I would always tell him what I had done and it was obvious that he would get excited as I would graphically tell him about the sex. Sometimes we would have sex together afterwards, but mostly I was too tired and instead would remove his CB and allow his to masturbate.

One night I returned from after having really great sex with two guys and as I recanted the story it really turned him on and he begged me to allow him to have sex. I thought about it and eventually agreed but that he would have to lick me clean afterwards. He protested that this meant he would also be licking out the other two guys cum as well. I told him it would be no different from the time he had licked me clean of his cum, only more of it and besides he could take the offer or leave it. Obviously he was desperate and agreed. The sex was nice but I really had the biggest climax when he licked me out.

I had now set a new bench mark and after coming home from a date, I would always make him lick me clean, whether it was from my pussy or my ass. Sometimes I would allow him to have sex with me, but more and more I would only allow him to masturbate.

Around a month or two of this, I started bringing dates home to have sex and I would make him introduce himself as my sissy cuckolded husband before sending him to his room whilst my date and I retired to the marital bedroom. Once my date left, I would call my husband in to lick me clean then send him back to his room for the rest of the night. It was during one such occasion I decided I would love to see my husband suck another mans cock (possibly it was pay back for all those times I mentioned earlier where he wanted me to orally pleasure another woman but he wouldn't so much as touch another man)

Anyway, I told him what I wanted him to do and he really flew into one, saying he was not a homosexual. Once he calmed down though, I explained, one, he was already proficient at sucking my strap on and a cock was no different, two he was already swallowing other men's cum when licking me clean, three I didn't want him to suck them off, only make them stiff (I lied) four this way he would know the mans cock was clean for his wife, five if he didn't do it I wouldn't unlock his CB and allow him to masturbate any more and six I knew he wasn't homosexual, but he was a sissy and that's what sissies do for their wife's. Thus he had no option if he ever wanted sexual relief again, but to agree.

The first time I made him suck cock I only had him suck the guy stiff as I told him but the next time I told the guy I wanted him to cum in my husbands mouth and make him swallow and so at the crucial moment the guy who I had chosen for his strength held my husbands head firmly in place and shot his load down his throat. My husband was completely caught off guard and sounded as if he was drowning as he gagged trying to not swallow but of course he did as he had no option.

Again another bench mark had been achieved and I would more than often make him suck them off completely.

The next thing I decided is that I would love him to have little titities instead of the prosthesis in fills that were used to pad out his bra.

This took quite a bit of planning on my part. I told him I thought it would be a good idea if we took a holiday to Portugal together and alone, as I was now growing more trustful of him. I chose Portugal as there was clinic I found there who would put breast implants in a man with no questions asked.

The first week at the villa I had rented, I allowed him all the sex he wanted with me and to act out all his fantasies. I also allowed him to be dressed as a man and we even had a threesome with another woman.

During the second week I told him how much I wanted to get back to how we were before but that I was also very turned on when he was dressed as a woman and fantasised about him having breasts that I could suck on a play with when he was fucking me. I kept on this tack over the next few days and gradually brought in about him having really small breast implants. Not much more than man boobs I proclaimed.

Of course he would have none of it, but I kept on and on and without going into lengthy details (I will come back to this another time), one debauched night he agreed and before he knew it I had him in the clinic the next morning and the job was done.

After staying in the clinic for a couple of days and recuperating for a further two weeks at the villa, I decided to treat him and allow him penatrive sex, telling him it was the best ever. I even arranged for a further couple of threesomes with the woman I had met earlier and I also got her to tell him how fabulous the sex was with his new titties.

However, once back in the UK I soon had him back in the old ways of being my sissy cuckold.

Before that though, I took him to the local department store for bra fittings and new underwear. They had seen him dressed as a woman plenty of times before, but they were absolutely enthralled by his breast and took great pleasure in making model different outfits.

Anyway, as I have said I soon had him back to being only allowed to orally pleasuring me and sucking cock. The men especially enjoyed playing with his titties whilst he sucked them off.

I now had to move him up to the next level of being penetrated by men.

So I sat him down and told him that as his penis was so small he was unable to satisfy women by penatrive sex and so he was not a man and as the only way he could satisfy a woman was the same way another woman did and that was orally or with a strap on. But he was not a woman as he had a penis even if it was tiny. That is unless he wanted it removed which I guess he didn't. So if he was not a man and he was not a woman, then he was a sissy and as a sissy he not only had to pleasure men as well as women. He did ask me why women including myself had told him he had a big cock in the past. I told him that they and myself had only said this so as to not hurt him but the truth had to be told. He then asked what I meant by pleasuring men as he was already sucking their cocks for them. I told him that men also had other needs and this included penetrative sex and so as a sissy it was his duty to offer himself to men for this. I also told him that I wanted him to do this so he too could feel the pleasure of having his pussy stretched by a big manly cock, feeling that cock fill him so he could take no more and feeling a man pumping his seed deep inside him. He then enquired as to where the men would penetrate him as he didn't have a pussy. I told him as a sissy his pussy or fuck hole as it is now called is his ass.

He didn't raise any objections and at the time I was mystified as I had expected a strong protest from him. But after speaking with my father, he said it was because with the breast implants he had obviously resigned himself to doing whatever I commanded of him.

However, as he hadn't raised and objections, I went the whole hog and told him that he shouldn't just expect men to fuck him but that he would need to ask and even plead with them on occasions to do so.

No sooner had I finished telling him, I was on the phone and setting everything up for the weekend with Glen, one of my lovers.

That Saturday evening Glen arrived and gave me the most beautiful bunch of flowers. After a drink we enjoyed a meal cooked and served by Chloe who was dressed in a pretty little maid's uniform I had purchased for the evening.

Once we had eaten, Glen and I settled down and watched a movie whilst Chloe cleared away and cleaned up. When the movie ended Glen and I retired to my bedroom where shortly after Chloe knocked at the door as usual and asked if she could also retire for the night and if there was anything we wanted before she went to her room.

I told Chloe my husband that I wanted her to give Glen a blow job first as I wanted the sex to last a long time.

My husband then went round to Glen's side of the bed, knelt down and took Glen's semi hard cock into his mouth. Very soon Glen came and shot his cum into Chloe's mouth. As per normal, my husband opened his mouth to show me Glen's cum before I ordered him to swallow it.

Chloe then did as I had told him and asked Glen if he would be so kind when he had the time, if he would penetrate her sissy fuck hole with his manly cock, so she could feel the same sensation as a woman does when she is stretched and filled with a manly cock and filled with a real mans baby seed. I was very impressed and proud by my husbands appeal to Glen as he had done as exactly as I had told him to. Glen replied he would consider the appeal and Chloe retired for the night.

In the morning Chloe knocked and entered with two glasses of orange juice for us and asked if there was anything else we needed. I told her I needed cleaning. She got onto the bed between my legs and kneeling down buried her head into my pussy and commenced to lick me clean of last nights cum.

Glen then rose and also got onto the bed behind Chloe. (The rest is what I saw in my mirrored ceiling and wardrobe doors, what Glen told me and what I could feel) Glen then lifted my husband's skirt (as instructed Chloe was not wearing any panties, nor did she have her but plug in) and spat onto Chloe's ass. He then took two fingers and pushed his spit into Chloe's ass and commenced fingering her, to which she responded with a gasp. Then removing his fingers he spat onto his hand and rubbed it into his cock, which he then placed against my husbands now open fuck hole. At first he gently pushed his cock into Chloe's and again I felt her gasp. But then once half way in, he rammed his cock into Chloe till he could go no further. This time Chloe my husband really gasped and moaned.

Glen then began to repeatedly withdraw his cock half way before pushing it home again, causing my husband to more and more frantically eat me out.

Next Glen put his left hand round the front of Chloe's skirt and ran it up her inner thigh, past her stocking top and found her clitty cage and exposed ovaries. He then closed his hand around her ovaries and commenced simultaneously squeezing and pulling on them. This produced even more moans and groans from my husband and caused him to lick me clean even more frantically than he had ever done before.

Glen next leaned over onto Chloe's back forcing her mouth deeper still into my pussy. Then with his free hand he reached round to the front of my husband's blouse, flipped open the buttons and allowed his titties to swing free. He then took one into his hand, holding the nipple ring between his knuckles and commenced also squeezing and pulling on it. Apparently this was causing my husbands fuck hole muscles to contract and expand the same as a woman's vagina muscles would do, thus in effect Chloe's fuck hole was sucking on Glen's cock. My husband was now really licking and sucking on my pussy as if his life depended on it. He was also moaning and writhing so much that Glen and I both laughed and said my husband must like being fucked in the ass as he is moaning as if he was a whore on heat.

I then  felt Glen shudder as he pumped his spunk deep into my husbands ass and I also seeing what was happening and with my husbands intense licking and sucking on my pussy, I shuddered into the most intense and prolonged orgasm I have ever had.

Afterwards, I instructed my husband to put the orange juice tray on the floor and squat over it with his back towards us. We then watched as globs of Glen's cum ran from his ass. Once the flow had stopped I ordered him to lick the tray clean, and then suck Glen's cock clean, before dismissing him and continuing to have sex with Glen.

As I have said, this is an outline and if anyone has any specific questions then feel free to ask me.


Comments (4)Add Comment
written by cros, November 27, 2015
Hey everyone.
My Mistres asked me recently to start HRT and later when my chest will grow a little do a boob job.
I am a closet sissy, nobody know about me in my life besides my Master. I really want to be a sissy and undergo this changes but on the other hand I am afraid of the consicquences and how it may effect my life.

My best results is a chest that will be feminine, but also unnoticed when I'm wearing clothes(baggy clothes or multiple layers). Do you think I can pull this off? Because If I can't I might as well consider a big chest like DD.
or put the breast implant

Sissy Lolita
written by Sissy Gabriella, July 17, 2010
Dear Mistress Sadie
I never saw this blog before but are aware that it is not new but it is such an amazing story and i hope my Goddess will do the same to me, even i am sure i need a lot of forcing but a Powerful women like my Goddess and You can do such things to their sissy slaves.
Courtsey in deep respect
sissy gabriella
great writings
written by toilet, February 25, 2009
as a hetero slave i hate forced engagements with men. but i guess that is why Madam Sadie and Mistress like to force us slaves to do them so much. it is an honor if it is their will.
written by shovelhead1978hd, February 24, 2009
That was one a the best told stories I have ever read Thank you Mistress

Write comment
You must be logged in to post a comment. Please register if you do not have an account yet.