Sissy Cuckold Stories

There are numerous reasons that people love cuckolding, including being able to watch a partner or friend get pleasure. Getting pleasure from other people is a natural feeling, and the desire to watch others can be as well. For people who are looking to open up and get into this sort of lifestyle, there are many entry points and tips. Starting conversations with other people is essential, and doing it in a tactful way is ideal. Learning about cuckolding and sissification is also essential for these types of conversations.

Sometimes, however, pornography and erotica are a way that people can introduce fantasies and fetishes to others. The Mistresses here are also excellent for fulfilling your desires. Using Sissy cuckold stories, you and your partner or Mistress can read them to each other and use them as inspiration. There are many different genres of erotica out there, with sissy cuckold erotica being more common than most people think. It is natural to have fetishes, and this website is a top spot to get more information about them. You can also explore with the Mistresses found here.

Sissy Cuckold Stories

Cuckolding is when a person watches another person who they are in a relationship or sexual partnership with getting it on with another person. In many cases, it is watching a wife or Mistress fucking or doing things with another guy. Also, this fetish can be explored in other ways, including through erotic stories, Skype BDSM sessions, and more. People love it when other people are enjoying their lives, making Skype cuckold sessions and other types of Internet interactions quite common. Tons of people have turn-ons about watching other people have sex, and large numbers love to be watched as well.

Are you fascinated by the cuckold phenomenon? Many people combine it with sissification. Sissification is when a Mistress, wife, or sexual partner has their partner dress up in panties, dresses, and more. Sometimes makeup is also involved. This feminization can add some roleplay humiliation elements to sexual experiences, which are also common due to both people enjoying them.

People Enjoy Different Things 

Being able to have sexual experiences with a wide range of people can add to the excitement of having sexual experiences with them yourself. Both partners can learn more about what each other enjoys, what others enjoy, find new sex positions, and connect in their enjoyment of watching their partner be pleased. In many cuckold situations, they are taking pleasure that is psychological and mental/emotional pleasure too. What they get out of the experience is in some cases physical too, however. Many people find that having sex with their own partner after a cuckold experience leads to more intense orgasms overall.

My Sissy Cuckold Experience

The experiences I’ve had with cuckolding and with sissification started as two separate things. Since college, when I lived in a coed dorm and chatted with a newer close friend about how pretty her clothes were, she asked if I wanted to try them on; jokingly. I have been fascinated with the beauty of panties, stockings, dresses, and more. When I got married, I put some of these experiences aside. Talking about sex and sexuality made me nervous, particularly with such a unique fetish. Cuckolding itself came a little bit later, about five years after we had gotten married. We still had a healthy sex life, and as we watched a movie that had a cuckold scene in it, I found myself getting turned on. Communicating my openness to trying it out was a little nerve-racking, but it also opened our communication sexually and began her journey to new adventures.

About six months later, we had found and met a person who seemed like a good match. They had done cuckolding before, so it seemed natural. Finding a drama free person was essential in cementing what has now become our regular lifestyle. He had large muscles and a massive dick, one that was much bigger than mine. As I sat down in the bedroom and watched her moan from the pleasure she would occasionally glance over at me and look into my eyes. While we had not talked about me masturbating during the experience, I could feel my hard cock filling my pants. After all was done, she and I had some of the best sex we’ve had in our lives up until then.

After, I recounted my experience with my college friend. My wife and I were about the same size, and I modeled her panties for her. After doing more research, we decided to enter into a little bit more of a BDSM style relationship, at least in the bedroom. She would dress me up in my panties that she bought me and compliment my feminine body. Eventually, we moved on to makeup and full outfits. The idea of combining both of them together came to me while watching the pornography scene one night. After sharing the scene with my wife, we decided to give it a go.

It had been about six months since we had seen our sexy cuckold friend, though we had had other cuckold experiences since then. I was a little more nervous, however, as this would be the first time we had communicated with somebody about me touching myself, and it would be the first time anyone had saw me as a sissy since we began. When he came into the house, he smiled. After some mild humiliation, I was set down in my seat and ready for the show. As he slid his large stick into her, I began touching myself. I had been instructed not to cum; my wife wanted me to do that inside of her afterward. I had to slow my strokes way down to prevent myself from cumming just from watching her. It was like being a woman and watching porn at the same time. There was a beauty in her form, and the feminization and subtle humiliations made it even hotter. 

Since then, we have expanded, and I also have Internet fun with a Mistress I enjoy a lot. Being able to open our sexuality up changed our marriage. Even though it was already fantastic, it is even more so now. The biggest lesson of all is on how to tactfully find ways to communicate your fantasies and fetishes with your partner if you have them. People are most often more understanding than one would think, and expressing yourself is both a relief and a blessing.