Experimenting with Role Play, Role Reversal, & Penetrating the Foreskin

Guest post by Lady Jane

Readers, we here at BetterSexEd pride ourselves on being as open minded and progressive as possible regarding everything sexy, so when we come across something new, shiny, and exciting, we just have to share it with you and your sexual curiosities in mind. We realize that not all kinks, scenes, and sexual fantasies are the same for all people, however, we feel that exposure to less traditional, off the beaten path sexual behaviors can lead to conversation, experimentation, and who knows, perhaps the opening up of some of your own wild, secret, and closed sexual doors. You don’t have to necessarily walk through the door, but consider for a moment the possibilities that await on the other side… I always encourage safe exploration, the gentle pushing of boundaries, the path to your ultimate pleasure, communication, communication, communication, and remind you to not be judgmental of yourself or your partner(s) if you discover a new kink that really tickles your pickle.

So I have this new boyfriend who loves role play, which is a good balance for me because I love role reversal (the two often go hand and hand). He’s an intense and passionate person in real life so naturally, he’s an intense and passionate lover. He enjoys being dominant, giving commands, and being in control which is refreshing for me as someone who isn’t particularly submissive or dominant and as someone who gets easily bored in the bedroom. With this dom/sub model, I enter a role as a submissive and he momentarily takes on a dominant role during certain sexual encounters.

We don’t use any formal “yes sirs” or “please sirs,” it’s more like rough handling, boob slapping, and the occasional gentle pressure at the base of my neck, on my upper chest, just below my collar bone.

The added amount of slight pressure near my throat adds an intense feeling of loss of control in a totally controlled way that just about causes instant release when I’m finally permitted to take the next breath in. There’s something about the power exchange, total trust, and deep rush of breathing in after quick seconds of holding the breath that just drive a lot of us absolutely wild. Everything about it is sexy. The intense build up, the abruptness, the rush and slight panic that occurs when you realize someone is taking control of you, and the sound of air pushing out of your mouth in that moment is just unspeakably hot. Proceed with great care, caution, and an open mind.

I’m surprised that I like this so much since I usually don’t like people touching my face or head. It’s amazing what a little consent to boundary pushing can do with a person you trust and are intimate with. If this is uncharted territory for you, but something you would like to try, definitely have a long conversation about this BEFORE you do it and please, please, please, be safe.

I’ll add a caveat here that breathplay is something that shouldn’t be taken lightly. It should only be done after safe, consensual boundaries have been established and done by someone who knows what they’re doing. I’ll also add that there are cases of breathplay leading to death so everything from rules, to safe words, to verbal permission, to when it’s going to happen, to when it’s going to stop, needs to be discussed BEFORE anyone’s hands go anywhere near your neck.

I’ll admit, it’s fun to let someone have their way with you, almost as if they were playing a part in a dungeon scene porno. This is the fulfilling world of role playing that so many people love so much and it’s easy to see why. I’ll also admit that it’s somewhat new to me and is definitely pushing my boundaries in a great way. I also find myself becoming more intimate and trusting of my partner because exploring sexual boundaries as a team can be a wonderful thing.

On the flipside, I mentioned role reversals going hand in hand with role playing. For example, I especially like the reverse spooning position where the smaller of the two partners holds the other one. My boyfriend had never experienced this before. Often we see a traditional spooning where the “bigger man” cuddles up behind the “smaller woman,” however, I’m proposing you swap the norm and go with something a little more radical where the tinier of the two snuggles up behind the other. One thing is for sure, no matter how big or small, most of us humans like to be held. Just for a moment, release your ideas of traditional gender roles and mix it up.

Like this morning, we discovered a great new role reversal where I, the female identified, penetrated my male identified partner’s penis.

Technically, I penetrated his foreskin, but it’s all the same structure, just the same. Now I don’t usually get the urge to penetrate someone (though there was that one time in the hot threesome with the French couple where I genuinely wished I had a penis), however, I have experimented with women and find it very pleasurable to explore a vagina with my fingers every once in a while.

Using my fingers to stimulate the head of my boyfriend’s penis under his foreskin was totally new for both of us and I had never heard of or done anything close to this before so I’ll talk you through it so you can give it a try. It’s a little like manually stimulating a woman’s vagina, vulva, and clitoris in that you are striving to stimulate the most sensitive, specific areas while at the same time, giving good pressure to the surface area as a whole.

Of course, your man has to have a foreskin in order for this to work, although you could simulate a foreskin by cupping your hand around the head of the penis and inserting your finger between your cupped hand and his cock. Begin by gently massaging the top of the foreskin, gently pulling it up and over the head of the penis. Circle around it with your smallest finger taking care not to move too quickly lest you stretch something that needn’t be stretched.

Next, when you think he’s hard enough (you’ll need a semi-erect penis to provide stability and structural support for your finger), insert your finger underneath the foreskin making sure the foreskin doesn’t roll back. You’d be surprised how flexible, soft, and expandable foreskin actually is since it needs to expand to accommodate the penis as it changes size during an erection.

The real pleasure button comes from making a “come hither” motion (just like stimulating a female g-spot) just under the rim or the glans of the penis. This is the most sensitive area for a lot of men with foreskins because it is the least exposed part. You can run your finger along the underside of the rim, give the head of the penis more of a massage, or flick your finger gently along the line of the glans to the font of the penis or frenulum. Go all the way around with your finger inserted underneath the foreskin.

Keep the foreskin rolled up around the head of the penis (it’s okay to use your other hand to keep it gathered at the top) and you can gently insert another finger if he’s ready. Granted, I have small fingers, but do what feels best. Next time I’ll try to get my tongue in there which will hopefully be equally well received. Have fun exploring out there (and in there, too!) and as always, be safe!