I have a lot of guys contact me who are beginners and want to know what a beginner session would involve.  I generally take some time to work out what sort of session they are after. Regular sex? Kinky sex? Playing with toys? Giving up control?

The first point is that I don’t play without a safeword. Generally I use the word “RED”. If the boy says that then the session stops immediately – and won’t be restarted that day. When the safeword is used, the boy is untied, unchained (or whatever!), they dress and leave. They can absolutely come back on another day. The point of a safeword is to protect both the top and bottom. But using it means the fun is over. This means that the top has an incentive not to push the boy too far and the bottom has an incentive to take a little more than he might otherwise be comfortable with.

I don’t use ‘slow down’ words. The problem with having a word like ‘orange’ to slow the session down is that it means the boy ends up in control. You end up with a ‘more, more, more…orange… more, more, more…orange…more, more, more…orange’ situation. Which is essentially the boy being in control. So I just use a single safeword.

The first choice is whether to be blindfolded on arrival. Some boys love to be blindfolded and only meet me afterwards. Other wants to meet and have a drink first. Either approach is fine. It depends on how excitement the boy is prepared to accept.

Generally I’ll blindfold a beginner during a session. I don’t use a hood or anything else that obscures the face of a beginner – I want to be able to monitor their reaction to a range of things to make sure that they are having a good time. I generally strip them extremely slowly – lots of skin contact. Running my hands up inside their shirts and caressing their bare chests or running my hands up and down their spine. I love to tease boys by putting a single finger into the waistband of their underwear and running it around their stomach. It’s fun to slowly take off their pants with your hands caressing and feeling their legs as they do.

One of my techniques is never to touch the cock of the boy. I’ll caresse and play with their balls, squeeze their ass cheeks, suck on their nipples but not touch their cock. I like it when a boy starts to leak precum without any dick stimulation at all.

The first session will generally involve some level of restraints – nothing too full on. It’s about getting a boy used to someone else being in control. It might be as simple as having his hands in leather cuffs clipped behind his back as I slap my cock across his face while he is on his knees blindfolded, collared, in a harness.

Generally some skin games – either running a singe ice cube over his body, or a feather, or a fur lined paddle. Something very sensual – perhaps with a little bit of a sting.

Normally then into the sling for some gentle ass play. If the boy relaxes, and it’s normal for a first time boy to be a little nervous, then we might go further and I can slip my cock into his ass.

The session generally ends with the boy experiencing the unique experience of being made to cum while entirely helpless.

Sound good? 😉

A photo of Sissyboy