Sissy Cuckold

While many people may look at sissy cuckold as a fantasy or role playing expedition, it is actually more of a lifestyle for people who are serious about it. This is a lifestyle that both straight and gay couples engage in, with few differences.

The definition of cuckold is simply that a husband or boyfriend wants to see his wife or partner having sex with another man, and enjoying it. It is not a threesome in that all three are participating in the sexual action. The partner or wife, and extra man are actually having sex, while the husband/boyfriend or partner watches from the sidelines. Cuckolding may also involve the wife or partner going out for the express purpose of having sex with another man, and coming home afterward to tell her partner all the details. The partner is the “cuck” and is almost always faithful to his significant other. Cuckolding means the wife is having sex with another man. The partner is also known as the “hot wife.”

Now, let’s look at how this fits in with a sissy cuckold. This is a part of the world of cross dressing. Many members of this particular culture also think of themselves as “sissies,” or “sissy cuckolds.” These men (if indeed they ARE men) have given up their masculinity to their wives or partners. This includes their personal right to a normal sex life. Many of these sissy cuckolds have not had normal sex with their wives or partners in months or even years. Some men in the sissy cuckold lifestyle are so devoted to it that they know they will most likely never have normal sex again.

A sissy cuckold is not entirely sexless. Most of them are allowed to take part in the sex lives of their wives or partners to some extent. However, this is done, for the most part, by them watching their wives or partners having sex with another man. This is not as bad as it may sound though. You see, most true sissy cuckolds LIKE seeing their wives or partners getting a lot of sexual pleasure from another man. They live to please their significant others, and will agree to anything that makes that happen.

While this is a much different sort of arrangement between couples, and may not seem “fair” or “right” to most main stream couples, you must remember that everyone enjoys different things. Each individual has his or her own sexual preference, and is entitled to live whatever lifestyle they choose, as long as they are not hurting anyone. Simply put, everyone should be entitled to live the way that makes them happy, without being subject to others passing judgment.

Now, you may wonder just how a lifestyle of this sort actually begins. It can start, as so many other things, as an initial thought or fantasy. At the beginning of a relationship, someone who is a sissy cuckold at heart may have seemed like a “real man.” However, he is actually harboring these thoughts and ideas of what it would be like to live as a sissy, to be feminized, and to only serve his partner, to make her or him happy.

One of the mainstays of this lifestyle choice is that the sissy cuckold agrees that his partner is allowed or entitled, to receive pleasure from a real man. This is a huge part of the deal, and involves his partner bringing these real men home so that he can watch while his partner is receiving pleasure.

While others may not agree that this is a wonderful sort of relationship, couples who choose this way to live are usually quite happy with the entire arrangement. Oddly enough, a sissy cuckold usually starts out with a quite normal relationship. He and his partner have regular sex on a normal basis. As time goes on, however, he starts to have fantasies of his partner receiving pleasure from other men. When he becomes brave enough to reveal his fantasies to his wife or partner, that is the time for a serious discussion on whether or not they can both agree to give this lifestyle a try. BOTH of them must be satisfied with the arrangement, though, or it will not work.

Some of the things a sissy cuckold starts to think about include the fact that his wife or partner deserves “more” than what the sissy cuckold is providing. This is also usually when he begins to doubt that the size of his penis is what it should be. Most sissy cuckolds think of themselves as being inadequate with regard to their penis size. Penis humiliation is often a part of the sissy cuckold fantasy. He starts to doubt that his penis is large enough, or hard enough to give the pleasure his wife or partner is worthy of. This is about the time that he starts to spend a lot of time thinking about what it would be like knowing his partner was being sexually satisfied by a real man.

To decide if you are a sissy cuckold, there are some questions you can ask yourself. First of all, do you find yourself thinking or dreaming excessively of other men sexually pleasing your hot wife? While you may also be a bit jealous, are you still immensely excited by the thought? You know that it would be humiliating, but do you also find that humiliation exciting? If you answered yes to these questions, or even a couple of them, you just might be a sissy cuckold.

Now that you are reasonably sure that you are a sissy cuckold, what should you do next? That is going to depend on your personal situation. Do you think your wife or partner will go for it? This is a very important question to answer before approaching a discussion about it all. If you have already been delving into the area of things like cross dressing or other feminization techniques in the bedroom, this may be easier than you think. That door has already been cracked open just a bit, so it may not take that much more to throw it wide open. It will simply make the transition to full scale sissy cuckold that much easier.

What do you do if you are worried about your wife or partner not enjoying this idea? Let’s look at some ways to ease into the discussion. First of all, if you are with someone who is already a bit on the controlling side, then things may be a lot easier than you think to take it a few steps further. Your partner may already enjoy playing the part of the dominant one in the relationship. This may set the stage for the humiliation and feminization that you crave. Hint at the idea that your penis is not adequate in either size or hardness, and that you feel you don’t have the ability to satisfy her or him. You can actually work this part into any type of domination fantasy the two of you may be engaging in.

That’s a great way to begin. Your partner just may pick up on your need to be humiliated and made to feel like the worthless piece of garbage that you are. You may start to get your wish of being told that your little penis is not worth the time of even looking at. As this part progresses, you might try getting permission to wear a pair of panties or other feminine attire. Seeing you dressed up like a little sissy might actually result in some excitement for both of you.

Suppose that you are now getting what you want with penis humiliation as well as being allowed to dress up as a sissy. This is going well, so far. You may even be able to encourage a higher level of both of these practices. Once you see that your partner is actually enjoying these things, it might be the time to broach the subject of you becoming a sissy cuckold.

It is surprising the number of people who harbor these thoughts and feelings, yet have no idea that there is actually a name for it. There are still many others who have never heard of this lifestyle and don’t know that it exists. So, when you sit down to discuss this with your partner, you might find that she or he has no idea what you are talking about. However, if you have already been experimenting with the idea of penis humiliation and cross dressing, it should not be too difficult to explain.

Once it is out in the open, there will be many questions to answer and details to iron out. That is, of course, if your partner is agreeable to trying it out. Assuming everything is a go, the two of you will need to decide just how far you want to take it. Will it be a “sometime” thing, or more of a radical lifestyle change? It might be best to start out with an occasional foray into the area of full sissy cuckolding before deciding if it is right for you as a couple.

Let’s look at how an experimental adventure into the world of sissy cuckolding might be conducted. Suppose you and your partner have discussed the idea of giving it a shot, and you are trying to set up something for your first time.

You will help your wife or partner get as gorgeous as possible before going out. Of course, you already have a “hot wife,” so this won’t be too much of an issue. You may be dressed in a cute little maid’s uniform for this part, as you assist your partner through a bath, make up, dressing, and hair styling. You are at your partner’s beck and call. Once she or he is ready to go out on the hunt for a real man, you will make sure everything is perfect.

While waiting for your partner’s return, you will be engaged in such things as cleaning the house, or anything else that you have been instructed to do. Everything needs to be absolutely perfect when your partner returns home. He or she will most likely be quite tired after spending hours having sex with a real man, and will want to be pampered.

Now, on this first time out, you and your partner may find it better if you are not watching the sexcapades right away. So, you will wait patiently until your partner has returned home. Then you will do whatever you are told to do in order to make her or him more comfortable and relaxed. This might include drawing a bath and bathing your partner, drying her or him off, applying lotion or a massage. While you perform all of these tasks, your partner will tell you, in great detail, everything that transpired during the evening and night.

This is the part where you will find out if you are truly a sissy cuckold. You are about to hear all the details of how the love of your life spent hours having sex with another man, a REAL man. Brace yourself because this just might turn out to be more than you can bear. Your partner is going to tell you how they kissed, touched, how big his penis was, and how it felt during sex. You are going to hear about every kiss, touch, stroke, and whatever else they engaged in.

Now, if you find that you are becoming totally jealous, hurt, and depressed while you listen, then stop right now. This is truly not the lifestyle for you, and should remain only an occasional fantasy that is played out between you and your partner. There is nothing wrong in just wanting the fantasy and not the reality. In addition, you will at least know how you really feel.

On the other hand, if you find yourself becoming more and more excited as your partner tells you of these details, and you are hungry for more of them, then you are most likely a true sissy cuckold. You are going to want more of this experience in the future, and you may even desire a total lifestyle change.

Since it is only your first time out, your partner will probably allow you to relieve yourself through masturbation while she or he watches. You will continue to hear more details of how well your partner was satisfied as you stroke yourself. Your partner will probably also throw in a few humiliating comments about how inadequate your penis is compared to the real man she or he was with the previous evening. All of these things will most likely only serve to increase your excitement, and you will be allowed to orgasm to this. Of course, you must also understand that you are going to be expected to clean up any mess you make from it.

You need to understand that if you choose to make being a sissy cuckold your lifestyle, you will be giving up a “normal” sex life with your partner. From the moment you make that decision, you are making your partner available to whomever she or he chooses sexually. If you are a true sissy cuckold, this will be perfectly alright with you, and even exciting for you to think about.

If both you and your partner decide that this is the lifestyle for you, as a couple, you may want to start making plans for your partner’s next excursion. The next time your partner goes out for a night of wild sex, when she or he gets home, you may want to add to the experience. Your partner will arrive home, and you will do what is required to help her or him relax. This time, though, you may be allowed to clean your partner. If you are with a female partner, this will give you the chance to experience a “creampie.” For those of you not familiar with what this is, it is the act of orally cleaning up another man’s ejaculate from his partner’s vagina. If you are with a man, this may be a bit difficult, but can still be done. You will simply be licking whatever ejaculate is left on the head of his penis, or on other areas. If he engaged in anal sex, you will be given the privilege of orally cleaning the ejaculate from his anus.

These are all steps to getting prepared for the “main event.” What, you may ask, is the main event? If you have passed the other tests up to this point, you and your partner are going to venture into another area now. Everything will be the same as far as preparing your partner for going out and hunting. You will also be performing your same sissy cuckold duties, such as dressing up as a sissy, cleaning the house, etc, but this time you will be turning the bedroom into a den of seduction. Depending on whether or not the man your partner brings home is willing to be watched, you will prepare a place to watch, either in secret, or from across the room. As this is your first time actually bringing a real man into your home, you will want to be prepared for either preference.

What will you do when your partner has returned home with the real man in tow? Let her or him take the lead in this. You will be waiting out of sight in the bedroom. Your partner should come in and let you know whether you should go to your secret place, or if you will be allowed to view the action in full sight of the real man. If you are told to hide, then you will retire to your secret watching place. On the other hand, if this real man does not mind an audience, and wants his prowess to be appreciated, then you will set yourself up in your part of the bedroom.

As your partner leads the real man into the bedroom, you will be able to watch them undress each other. You will get to enjoy watching them kiss, touch and fondle each other. Some sissy cuckolds really love watching their partners perform oral sex on the real man, as well as watching the real man do your partner. You might be allowed to masturbate as you watch the events unfolding, but will most likely not be allowed to orgasm.

This is the time to let the real man sort of take the lead. He may not mind being watched, but will not let you join in. Or he might like the idea of being serviced by you. Servicing them will include being the clean up person. You will be allowed to “clean up” the ejaculate left in or on your partner by the real man. This usually encourages more arousal for everyone, at which time you will retire back to your viewing spot, and watch as they engage in yet more sexual activity.

Another, more direct way, you can be involved is by preparing the real man for your partner. This means that you are going to be used to get him excited. Normally, this is done by performing oral sex, or manual manipulation on the real man. This process is also known as “fluffing.” It is something that is done a lot on the sets of porn movies. There are women or men who are hired to keep the male actors excited and erect during short filming breaks. That would now be your “job” to keep the real man excited while your partner rests a bit.

Some sissy cuckolds involve other fetishes in this lifestyle. One such fantasy seems to be sissies who enjoy watching his “hot wife” with a real man of another race. This usually involves a white woman or man engaging in sex with an African American man, who also has an enormous penis. Sissy cuckolds enjoy watching their “hot wives” being thoroughly satisfied by a penis that can get the job done, and done well.

Some of the largest part of the pleasure involved in a sissy cuckold lifestyle is the preparation for your “hot wife’s” night out hunting for that perfect real man to be with. The sissy cuckold is usually very excited about helping his “hot wife” become even hotter by assisting with the bathing, shaving, moisturizing, applying make up, and all of those things involved in the art of primping. All the while performing these tasks, your “hot wife” will be taunting you by telling you about the real man she or he will be hunting on this particular outing. You will most likely also be told how inadequate you are, how small your penis is, and how you could never measure up to the kind of real man who has the ability to thoroughly satisfy someone.

A large part of being a sissy cuckold is following instructions and performing any task that they are given. It does not matter what this task is. It can be anything from wearing sissy underwear at work, to masturbating each morning and night followed by licking your hands clean. It totally depends on your situation. This is another reason why there is the necessity for setting rules well ahead of time. You may both have your limits or boundaries, and they need to be respected. It is highly likely though, that as a sissy cuckold, your boundaries will not be many. Your strongest desire will be to do whatever your “hot wife” instructs you to do.

One way that a sissy cuckold can work his way into the lifestyle is through a shopping expedition. You will be instructed by your “hot wife” to go shopping, most likely for feminine items. Your list will consist of everything from sexy underwear and lingerie, to feminine items such as tampons and feminine washes. As you go down the list of your items, you will be instructed to ask for assistance from people working in the various places you visit. This is designed to put you in your proper place as a sissy. The cuckolding will come later when those items you purchased will be used to attract the next real man.

Sometimes you will be instructed to dress up and accompany your partner on the hunting expedition. You will be wearing your sissy little dress, as well as whatever else your partner instructed you to wear. While your partner goes into the bar, club, etc., to land the next real man, you will most likely be instructed to wait in the car, which you will do no matter how late she is. Once she appears with the real man, you will most likely be told to drive them both back to your house. You should have already prepared the house and the bedroom for this special event. Therefore, the real man will feel welcome and comfortable when he enters the door. As your partner and the real man get the action started in the bedroom, you will be preparing snacks and drinks to serve them later. You might just be wearing your cute little maid’s uniform now, which would only be appropriate in your role as a sissy cuckold who is also serving.

Other tasks for you, as the sissy cuckold, may include turning down the bed covers for your partner and the real man. You may even be allowed to undress each of them before retiring to your corner of the room to watch as your partner is sexually satisfied over and over again by a real man. Be sure to have soft, clean towels on hand to clean up any messes left on the bed sheets. The bed sheets may even need to be completely changed by you in between each sexual encounter between your partner and the real man. You are expected to be ready for anything your partner requires or demands. She or he will not want to be kept waiting.

Some sissy cuckolds are instructed to repeat mantras each morning upon rising, and each night before going to bed. These can include such things as “It is right that I wear panties.” “My penis is so tiny and worthless, it is almost a clitoris.” “It is my sole purpose in life to serve my “hot wife,” and see to her every need and desire.” These can be repeated either in front of a mirror to yourself, or on your knees at the feet of your partner. Doing it this way is deemed very appropriate, as you are reaffirming your dedication to keeping your partner happy. However, you will have to wait to see what your partner prefers in this. Repeating these mantras daily will also keep first and foremost in your mind what your purpose in life is.

There are also some punishments to be handed out to a disobedient or mutinous sissy cuckold. You will never question a decision or demand made by your partner. If you even so much as ask “why,” you are setting yourself up for some severe punishment. Depending upon whether you and your partner enjoy physical punishment, you may receive a very intense spanking. If this sort of thing is not part of your lifestyle, your punishment will be more in the disappointment area. For example, if you have displeased your partner in some way, the next time she goes on a hunting expedition for a real man, you will not be allowed to be a part of it. Instead, you will be made to sit all alone at home, while your partner goes to the house of the real man for amazing sex. Not only will you not get to watch this, you will most likely have even the details withheld from you. There will be no cleaning up, nor will you get to hear about how your partner was thoroughly satisfied by the real man. You will basically be ignored until your partner has decided you have learned your lesson. Forgiveness will be forthcoming, but for this particular night, you just might have to sleep on a blanket in the corner of the room, while your partner rests in the comfortable bed.

Another way you may be punished when you are a disobedient sissy cuckold is by not being allowed release. Your partner will share some details with you about the night spent with the real man. She or he may even be sexually explicit in a visual sense by touching her or his sexual parts, showing you the ejaculate that still resides there. You will get to hear all about what took place, while your partner basically torments you by not letting you do anything except sit and listen. You may grow aroused, your penis becoming erect, yet you will not be allowed to touch it. Your partner’s goal at this point will be to punish you by creating almost unbearable excitement with no promise of release. There will probably be a great deal of teasing as your small inadequate penis tries to become erect. Then when you are fully erect, the teasing will only increase, as your distress is noted and made fun of. The punishment here is that you will not be allowed to even touch your penis, much less orgasm.

If there is a real man who is familiar with you and your partner’s lifestyle, he may be invited to be a guest in your home. What this means for you is extra cleaning and cooking, along with being ready to serve him and your partner. The maid’s uniform is appropriate for this, as are other sissy outfits, such as school girl uniform, or a slut outfit. Either way, your role for the evening will be to do the bidding of not only your partner, but the real man as well. This includes serving dinner, being ready to refill wine, and, of course, the clean up that follows. Once your partner and the real man have retired to another room, you might be instructed to serve dessert and coffee to them there. By now, there should be some active flirtation, as well as a small amount of foreplay. You will be witness to your partner and the real man laughing together, kissing and even touching each other in a sexual manner.

At some point in this evening, there may be the order to ready a bath for the two of them. You will be responsible for making the atmosphere for this as sexy as possible. Tasks may involve bathing each of them, and being on hand to dry each of them off with big, soft, fluffy towels.

The bedroom should be as seductive as possible. There should be candles and flowers, possibly even some rose petals on the silk bed sheets. If you have performed all of your duties to the satisfaction of your partner, you will be allowed to take your seat across the room and watch as the real man works his magic. It is also possible that you will be allowed to stroke your inadequately small penis as you watch. However, it is highly unlikely that you will be allowed to orgasm during their sexual play. That is reserved only for your partner, and should you slip up and do this, there will most definitely be a punishment in store for you.

There are no set rules in being a sissy cuckold beyond the ones that are made by you and your partner. Make no mistake. These rules are very important before becoming active in the sissy cuckold lifestyle. Both of you need to be happy with what is transpiring in this. Therefore, be sure to talk everything out before ever taking that first step. In this way, no one is unpleasantly surprised by anything.

Let’s talk about what happens if you try this and find that it is not for you or your partner. This can go one of several ways. You try it and you don’t like it, but your partner does. Or you try it and you love it, but your partner is not really into it at all. Either one of these can present a few problems ahead, especially if the one of you who likes it is REALLY into it. There are ways to compromise. While it may not totally satisfy you or your partner, a compromise can be a way to inject a little bit of difference into your sex life, yet not committing to a full lifestyle change.

For example, you have found that you totally love being a sissy cuckold, but your partner is not comfortable with it. A good way to deal with this fairly might be for you to dress up as a sissy on occasion, and have your partner tell you a “made up” story about how she or he and a real man had sex. Your partner can tell you all the things they did together while you sit and stroke your inadequately small penis. However, before you are allowed to orgasm, you will be made to service your partner and make sure that she or he is fully satisfied.

A scenario like that may help you to gain a bit of satisfaction in the part of you that feels you would be the perfect sissy cuckold. It is not a lifestyle for everyone. However, it is a very popular fantasy for some couples. Living out the fantasy may be all that you need to fulfill this side of your personality. There is a lot of information available regarding sissy cuckolds, and you may want to investigate some of it. You may find other suggestions for you and your partner to try, and some of these may work, whether she or he is into turning you into a sissy cuckold or not.

Above all, enjoy your fantasy. It may sound strange, but to those individuals who truly want to become a sissy cuckold, it IS an enjoyment. Hopefully, you will find your partner is a willing participant in making your fantasy become reality.