How she deflower the sissy slave in me

A beautiful woman and a male slave in a cage lying side by side

Her sissy, her object, her wife

I don’t know if it was part of her master plan, or whether it was simply a germ of an idea that, over time, has evolved into a lifestyle. It is certainly a lifestyle that has turned the traditional male/female roles upside down. She controls the money; I do the laundry; she makes all the decisions; I simply obey; she wears the pants; I wear the skirts (or whatever she tells me to wear). I clean the house while she watches television, or does whatever she wants. If she wants something, she calls on me to get it for her. In short, I am the traditional “woman” in our marriage, and I must wait on her hand and foot (literally).


Strong women to keep you in line near

One day, I guess she recognized how my role had evolved and decided to formally emasculate me by forcing me to wear “sissy” underwear. From that point on she started calling me her wife, or her “Little Sissy”. Sometimes, she looks at me disdainfully and says “I wear the pants in this house”. She then adds with a laugh “You wear the panties. Don’t forget it my Little Sissy” And that was only the beginning. But I’m getting a bit ahead of myself here.

In the bedroom, she makes the rules. She always has at least one orgasm. On the other hand, I am only occasionally allowed to cum. And, on the rare occasion that I am allowed to cum, she ensures that I lick up every drop. She wants no icky mess in the bed or on the floor, or anywhere (except on me sometimes).
Actually, it was in the bedroom that she started us on the path that lead to me becoming her “wife”.

I will wear a chastity device to show my love to you

When we were first married, we made love in the traditional vanilla way. Generally, with me on top, we seemed to make love all the time. In fact, looking back I guess we both had an insatiable sexual appetite. Then one day, after about 10 years of marriage, we had a serious conversation, and Fiona said that she was frightened that I would lose interest in her. For whatever, reason she was worried that I would start looking for a lover. I assured her that I love her and I would never do anything like that. It was a couple of days later that she dropped the bombshell. Fiona told me that her best friend’s husband had run off with a younger woman and that she was devastated. She then told me that she wanted me to wear a chastity device whenever I leave the house. At first, I laughed because I thought she was joking. I could see that she was annoyed at my response, so I reassuringly said “Look! Fiona, if you can find such a device, I’ll wear it any time you want, because I love you Fiona and if it will ease your mind then that’s fine with me.” Although I truly meant what I said, I didn’t fully appreciate what I was committing to, nor what it would lead to.

Sure enough, a couple of days later while I was drying off after my shower, she walked into the bathroom with the device in her hand. At first I didn’t even know what it was she was holding in her hand. She looked up at me, and smiled and said: “ are you ready for the chastity device?”

I guess she took me aback, and it must have shown on my face, because she smiled and said “You did promise”

I said “Sure go ahead, put it on if it will ease your mind”.

I guess it helped that I was quite small after my shower because it only took her a couple of seconds to slip it on and lock it in place. She then pulled me close to her and we shared a long sensual sexy kiss. It was the type of kiss that really gets me going. It always gives me a hard erection, and of course nature was trying to take its course, but the device was doing its job. Fiona, then laughed and quickly left me there in the bathroom trying to understand what was happening to me. I was as horny as hell but I couldn’t get erect because of the device. It was truly frustrating. After a couple of minutes, I gained some measure of composure and was able to pull myself together enough to wander nonchalantly into the bedroom. When I entered the bedroom, Fiona was dressed in her sexiest lingerie. She walked up to me smiling and pulled me to her, and we kissed again. This time it lasted longer, and our hands started to wander all over each other. Again, I was dealing with total frustration, and this time Fiona seemed determined to press every button I had to get me aroused. I felt her hand cupping my testicles, and then she started feeling the device. She then suddenly took a step backwards and looked at me. She laughed and said “That’s great! The device is working”. “Tell me about it” I responded. She then said: “I have one more request, and then you can go off to work.”

Challanged into denial

I said “Sure what do you want?”

She replied “There is one little sexual fantasy that I’ve had that you can satisfy right here and now.”

Well, now she really had my interest. I guess she’s going to take the damn contraption off me and we’re going to make love. Thank God I thought.

She sat down on the edge of the bed and she said. “I want you to get down on your hands and knees, and beg to go down on me”

She added “If you beg properly and sincerely, I’ll take the device off you tonight, and we’ll make love”.

I immediately dropped to my knees and said “Please Fiona may I go down on you. I’m begging you, please.”

With that she said “ it’s not bad for a start. You may crawl to me and remove my panties with your mouth, but keep your hands behind your back. At no time are your hands to touch me. Do you understand? If a hand so much as touches me there will be no lovemaking tonight.”

I thought to myself this is kind of strange, but who am I to question someone’s fantasy. I then started to crawl towards her. I could see that her panties were very wet from our kissing and petting. I tried to pull her panties down with my teeth, but of course it wasn’t possible to pull them off, and after a couple of minutes, and without thinking, I simply took both hands from behind my back and pulled them off, and Fiona also helped by wriggling out of them. She then pushed my head into her moist wet pussy, and I started to gently use my tongue on her. She was pulling my hair drawing me closer and she ordered me to probe with my tongue deep into her vagina. She then ordered me to suck on her clit. It wasn’t too long before she started to moan quietly. I realized that she was guiding and controlling my mouth and tongue by pulling my hair to guide my head and commanding me where, when, and how she wanted me to service her. Soon she came. It was unlike any orgasm she had enjoyed previously. I guess it was the first time she had been in total control.

After a couple of minutes, she looked at me and said “That was wonderful, Darling. Unfortunately, you disobeyed me. You touched me with your hands, so no sex tonight is your punishment. Now, you better give your face a bit of a wash and head off to work. We can talk tonight.”

Over the next couple of days, I realized that she was in fact taking over control of our sex life. I didn’t yet understand that it was more than our sex life that she was taking control of.

After the first two nights of chastity she told me that I had been a good boy and that I could cum. However, she said that I would have to allow her to tie me to the bed. Her rationale was that I could overpower her to get the key. By tying me to the bed she could go and get the key without fear of me following her. So I agreed to let her tie me up, and from that point on, bondage was a part of our lifestyle.

She had obviously planned this in advance because she produced some cuffs and chains, and before I knew it I was lying naked on my back with each arm attached to the top corners of the bed, and my feet tethered to the corners of the foot of the bed.

Some bondage will surely help me focus on her pleasure

After a couple of minutes she returned with the key, but instead of unlocking the device, she started teasing me. She started kissing me and running her hands all over me. She was driving me crazy. It was pure torture, and she was enjoying every minute of it. She then sat on my face and told me to kiss her pussy through her silk panties. Her panties were wet by now, and I felt her wetness on my chin as she sat on my face. After a couple of minutes, she removed her panties and then ordered me to use my tongue on her pussy. And just like the previous morning, she assumed total control of my tongue and mouth. I began to sense that she was using me like a sex toy. This time however, she stopped before she climaxed, and reached down and at last removed the chastity device. She then sat back on my face and began barking out orders on how I was to proceed servicing her. She began stroking my penis. I was almost instantly hard, and after the days of teasing and denial I was almost ready to ejaculate immediately. She then stopped touching me and told me to concentrate on her. She then got back to using my mouth and tongue on her pussy. I could hear from her moaning that she close to coming. But then she stopped, got off my face and moved over my still rock hard penis. She then gently lowered herself over my penis, drawing me deep into her vagina. I came within a whisker of ejaculating while she was sliding me into her very wet vagina. She looked at me, smiled, and said, “Here’s the rules darling. I am going to come with you inside me. But, you are not allowed to cum while you are inside me. I want you to cum after I get off you. If you come while you are inside me you will be punished. Do you understand?” I mumbled “Yes Fiona”.

With that she started to move her hips on me, and she began bucking up and down, deliberately sliding up and down my shaft. I tried hard not to cum, but by the third stroke I shot my load. It was probably the most intense orgasm I had ever had in my life. There was no doubt that days of denial made for a very intense orgasm. Meanwhile, she kept grinding and she came very soon after me.

After, a couple of minutes we both regained our composure. Foina laughed “One week of chastity is your punishment. Also, there’s one more thing that you will always do from now on”

She then got off me carefully and stood over my face and laughed “have some cream pie!”

With that she sat on my face and placed her pussy, dripping with my semen, over my mouth and said “Clean me! I don’t want one drop of that icky stuff left inside me when you’re finished. Do you understand?”

At that point, I didn’t know how I was going to last a whole week without sexual release. I certainly wasn’t going to risk making things worse. And for the first time in my life, I tasted what women around the World have been forced to taste since time immemorial, male ejaculate. In this case, it was my own. And at this stage I didn’t care, I had at last had an incredible sexual experience, and although I was now well and truly her sex slave, I was happy and content. I actually thanked her for the incredible experience, and I began licking her pussy clean, tasting the saltiness of my own ejaculate.

Setting the rules

So our new life together began. She became ever more sexy, and ever more unattainable. She started wearing the sexiest lingerie she could find. She also started wearing leather pants, and leather skirts, and silk blouses. After 10 years of marriage she knew how to push my buttons. She did all sorts of things to get me aroused sexually. Then she would leave me high and dry. She would promise me that I could cum if I did the washing, and the vacuuming, and the laundry. Before I knew it, I was doing all of the housework.

For the next few months I found myself adjusting to our new lifestyle. I have always loved my wife dearly, but now I found that I was falling ever more deeply in love with her. It is not something that I could rationalize, or explain. I guess love is strange, or at least it can be.

One day, while Fiona and I were enjoying a morning cup of coffee together, I asked her if she could explain why it is that I actually enjoy being denied any say in our sex life. I told her that I didn’t understand how I could possibly enjoy being kept in chastity. She smiled and said “It’s because you are submissive. It’s just a part of your nature, and it’s a part of your nature that I love, because I am dominant in nature. After all, you must admit that when I do let you cum, you really enjoy it. Don’t you?”

I smiled and said “Yes, you’re right. You have taken me to new heights that I never thought were possible.”

I then added “You know Fiona, I find that by being denied the opportunity to climax, I spend a lot of my day thinking of you. I picture your beautiful round bottom, or those breasts that I love to suck, or your pussy that I love to use my tongue and mouth on. In fact you haunt my mind, and I become totally enchanted by the thought of you. That’s why I end up doing whatever you ask of me.”

Fiona laughed and we embraced and started kissing, and without giving it a second thought, I picked Fiona up in my arms and carried her through to the bedroom. I then gently placed her on the bed, and we carried on kissing.

She then pulled away and looked at me and said “You realize that you are my sex slave.”

I smiled and said “Well I hadn’t thought about it, but I guess you’re right.”

She then said, “if you are my slave then you better start taking orders.”
I was a bit surprised by that comment, and I said “I thought I was doing a pretty good job at following your orders. After all, I am so desperate to cum, you know I will do anything that you ask.”

She then laughed “Anything!?” and I realized that I had walked into a bit of a trap, so I said “Well, I guess so, within reason.” She then looked at me quite earnestly and said “What do you mean by ‘Within reason’?”

I said “well, I mean I am not going to break the law, or hurt anyone, or do anything that’s dangerous.”

She then looked at me with a feigned hurt expression on her face and said “I am upset that you would even think that I would ask you to do anything that would break the law, or hurt anyone. After all, I am a lawyer”

“I’m sorry Fiona,” I replied, “I guess I was wrong to qualify my comment like that.”

She smiled and then said “so that means you’ll do anything I ask, right?”

I looked into her beautiful green eyes, and said “Of course Fiona, I have total and absolute trust in you, and I will do anything that you ask.”

She smiled and whispered, “It sounds like you are agreeing to be my slave.”

I realized that this was not a decision to take lightly, but I found the thought of being her slave absolutely enchanting and exciting. I gave her a kiss and said, “If you want me as your slave Fiona, it would be an honour.”

She smiled, and again we kissed. This time it was a long sensuous kiss. Our tongues gently explored each other’s mouths while our hands explored and caressed every erogenous area of flesh that we could find. I was, once again, starting to feel the frustrating sensation that had by now become all too familiar.
I expected that Fiona would very soon be asking me to go down on her, or perform some other sexual function that would result in her having an intense orgasm. But, to my surprise she pulled away and said “Now slave. I want you to remove all of your clothes right now.”

So like an obedient slave, I started to remove my clothes, and I put them in a neat pile on the bed. I was then a bit surprised when she went to the drawer and pulled out the cuffs and chains, and this time cuffed my hands in behind my back, and then cuffed my ankles, so that I could only walk by taking very short shuffle steps. She then gathered my clothes together and walked out of the room with them. I was hoping that she would return with the key to unlock the chastity device, but unfortunately, she came back empty handed.

At this point I was standing beside the bed with my hands tightly secured behind my back, and my ankles chained together. The only other item I was wearing was, of course, the chastity device. She stood in the doorway and seemed to be inspecting me, I could see her mind working. She then approached me and reached out and held my plastic encased penis in her hand and said “Poor Uncle John.” She then added “I guess as long as your hands are tied up behind your back there is no need to keep Uncle John incarcerated. Is there?” “Not at all.” I replied quickly.
She then marched out of the room and came back shortly afterward with the key in her hand. She then removed the device and started stroking my penis. To the surprise of neither of us, my penis responded to her gentle touch immediately. She started flicking my penis with her finger and she said “You know. Now that you are my slave, this penis belongs to me.” “It may be attached to your body, but otherwise it is really no different to any other sex toy that I have.” She then leaned forward and gave it a lick. She then drew it into her mouth and started sucking it. Inside a minute I was very high, and true to form, she stopped and walked away. I was totally frustrated, but at least this time I was able to enjoy having an erection, which is a sensation that was denied me while I was forced to wear the chastity device.

She came back a minute later and started to remove her clothes. She did it slowly and sensually, and from time to time she would interrupt the process to rub herself against my naked body, and stroke my penis. Finally, she removed her bra, and laughingly she hung it on my erect penis. She then went over to the chest of drawers, opened her lingerie drawer and took out a 3 feet long red cord. She walked toward me with a menacing smile on her face. She then smiled and said softly “It’s time for Uncle John to experience the joy of bondage.”

She removed the bra that she had left hanging on my erect penis and started stroking my shaft until I was close to cuming. It didn’t take long at all because I was very high before she even touched my penis. She then took the cord and started to tightly tie up my penis and scrotum. It wasn’t painful, but it was a bit uncomfortable. She had tied the cord tightly around the base of my penis, and then looped it around each testicle to separate them, finally winding it around the shaft and tying it securely just underneath the head of my penis.

Goddess is her name

She then pushed me back onto the bed and I lay there feeling completely helpless. I was lying on my back with my hands tied behind my back, my ankles were also bound, and now my penis was fully erect and very tightly bound. Never before had I felt so totally powerless. Fiona then got up on the bed and stood over me. She was naked except for her black panties which I could see were wet at the crotch. She looked down at me and said “Now slave, tell me exactly how you are feeling right at this moment.”

I felt that she probably already new the answer to the question but I replied anyway “I’m feeling extremely helpless Fiona. In fact, I have never felt so vulnerable in my life.”

She then said “Well slave, I have never before felt so powerful. I have complete and total power over you. You are my property. You are to serve me and make me happy. As my slave, you no longer have the right to call me Fiona. From now on you must call me Goddess, because from this point on I am your Goddess. Do you understand slave?” “Yes Goddess.”

I replied. She then continued “Now slave I am going to ‘Queen’ you. Do you know what that means, slave?”

“No Goddess. I have no idea” I replied. She smiled and said “I am going to sit on your face and use you to achieve sexual gratification. You are to use your mouth and tongue as I command. Do you understand slave?” Again I replied, “Yes Goddess.”

Now it was very strange, because although I was feeling very vulnerable, I was also feeling highly aroused sexually. It is a response and sensation that I simply couldn’t make sense of, but happily I didn’t dwell on it. I decided to just go with the flow and enjoy the experience of being a slave to this woman who had, through her intelligence and force of character, turned me into her slave and herself into my Goddess. As I was thinking these thoughts she lowered her wet panty clad pussy onto my mouth. This time however, she grabbed my head and pulled my head firmly into her bottom so that my nose was pushed into her anus, and my mouth was covered by her pussy. I was intoxicated by the sensation. The feel and the scent of her womanhood had me highly aroused and then I suddenly realized that I couldn’t breathe. A few seconds later I started moving my head in an attempt to get some air, but she held me firmly and I couldn’t move or do anything about it. I decided to relax and rely on her to not let me suffocate. After all, I had agreed to trust her. She then moved forward and allowed me to breathe through my nose. She then said “Remember slave, although I hold the power of life and death over you, you must always trust me to look after you.” She then removed her panties and she commanded me to suck her clit. By now I was an expert at sucking her clit. It had reached the point where I knew by every little movement of her hips exactly what was expected of me. Faster or slower, gentler or harder, I could suck her exactly as she wanted. In hindsight, it was the first thing that she had trained me to do. It didn’t take long before she came. It is probably because she was very high before she mounted my face, but she had a very intense orgasm. I felt my face being held in a vice like grip between her thighs as she came. And she came in an explosion of feminine nectar that I found absolutely intoxicating and highly sensual. I continued to lick up her juices, and to my surprise her hips started moving again as she had a second, very intense orgasm.

After a few minutes she got off me and lay on her back on the bed, and just relaxed. It was about 10 minutes later that she finally spoke. She said “Well slave you did well, and you should be rewarded. However, it will have to wait until tonight because I have to shower and go to work for a couple of hours, even though it is Saturday.” With that she got up and walked toward the bedroom door. Before she could leave the room I spoke up. “Excuse me Goddess, but shouldn’t you untie me?”

She looked around and said “Oh yes I almost forgot to tell you, a slave is not allowed to speak unless he is asked a question.” With that she grabbed her soiled panties, wiped them against her pussy and shoved them into my mouth. She then left the room and had her shower. I lay there for another half hour to contemplate all that had happened.

Starting the sissyfication

She came back and started dressing herself for work. I still lay on the bed trussed up where she had left me. She started talking, and with her panties still stuffed into my mouth I could not join the conversation. She said “I am going to have some simple rules that you will have to follow. To start with, you will only wear clothing that I allow you to wear. I have locked away all of your clothes except for those that are needed when we have to appear vanilla. And even those are under lock and key. The only clothing that you free to wear whatever you want are woman’s clothes. Starting right now you are only allowed to wear feminine lingerie. Your male underwear has been thrown out in the trash. You will wear panties, stockings and garter belt under your work clothes. You will also shave your legs regularly. I will be inspecting you. So you’ve been warned. Do you understand?” She then reached over and removed her panties from my mouth.

I replied “Yes Goddess.”

She then went over to her lingerie drawer and pulled out a pair of pink silk panties and walked towards me. I immediately had a sense of horror. She’s not going to make me wear those is she? I thought. Sure enough, she removed the cuffs from my ankles and started drawing the panties up over my legs. She had me stand up, and she continued to draw them up over my penis, that was still firmly tied up. She then started to untie my penis and, remarkably, it became instantly erect again. She then laughed “Well what do you know? I married a sissy boy.”

I was deeply embarrassed and ashamed, and I turned red in the face. She laughed again “Oh sissy boy is embarrassed!”

At this point I didn’t know what to do, and this was exactly the response that Fiona was hoping for. “Who would have thought that my macho husband, who was too masculine to even be seen in a pink sweater would be turned on by dressing as a sissy girl.” she laughed.
She then looked at my penis and said “Well, sissy boy we really have to do something about that erection if I am to get you back into the chastity device, and I am definitely not going to let you cum all over those pretty panties.”

She then told me to bend over the end of the bed. she then removed the belt from the leather pants that she was wearing and started whipping me with the belt. It stung quite a bit, and sure enough after about 3 or 4 strikes I was completely flaccid. I guess she was watching because before I knew it she had put the detested chastity device back on.

Finally, she removed the cuffs from my wrists and headed towards the front door as I stood there dumbfounded at all that had just transpired, wearing nothing but a pretty pair of silk panties, and still frustrated but aroused, and unable to do anything about it.

And, as she walked out of the door she said “Be sure to shave those legs before I come back.”


Find a mistress in

And that was the start of it all. From that point on, it became more than just a sex game. I also found that Fiona, would find new ways to control me. She would find new ways to ensure that I could not back out of this arrangement, although so far, I have never had the desire to back out. If anything it has been the opposite. The deeper she has drawn me in, the more I have enjoyed it.

Last Updated on