Masturbation Coaching...

A guide to sessions with Libby Sheppard

Is your masturbation routine boring, habitual and unsatisfying? You’ve probably never been more acutely aware of this than you are right now. Many of us are in lockdown, isolated, working from home, unemployed or on furlough. We’ve got more time on our hands and fewer accessible distractions. We’re disconnected from our partners, our lovers and our massage therapists. It is now entirely down to you to satisfy and pleasure yourself.

Compare pleasure and sex to food: if you were used to eating out in different restaurants every night (pleasure supplied through sex with different partners), or even in the same well-loved restaurant (in the case of monogamous relationships) you may now be realising ‘oh wow, I have absolutely no clue how to cook for myself!’ Many people are becoming aware of this opportunity to learn new ways to touch and pleasure themselves, in the same way they now need to learn how to cook their own dinner…

Maybe some of the following statements resonate for you:

  • ‘I am isolated and away from my partner at the moment therefore my sex life is only existing through self pleasure. I’ve realised that my relationship with masturbation is quite boring. I would like masturbation to be more pleasurable for me as now it is just a stress relief or something I’m doing as a distraction.’
  • ‘I want to use this enforced isolation time to learn how to access my full arousal and orgasm for myself, to understand better what turns me on and become more familiar with my sexual self.’
  • ‘Porn gets boring quite quickly and I am really noticing how it desensitises my experience of pleasure.’

Here are some ways that my masturbation coaching sessions are able to support you:

  1. Pleasure – you might need some right now in your life! To have an hour for yourself, focussed on your own body and doing something that is loving and delicious might be just the ticket!
  2. Inspiration – suggestions for new ways that you can self-pleasure with touch, breath and movement, getting out of the rut and ‘routine’.
  3. Healthier habits – putting in place a healthy structure for masturbation if you are slipping into unhealthy patterns with porn use and masturbation.
  4. Feeling more, thinking less – ways you can physically get your body moving right now that are gentle, not ‘punishing’, but will mobilise and get you grounded in your body when the mind becomes busy and over-active: my personal training background is really helpful here!

What exactly is masturbation coaching?

Firstly, some people are not actually looking for coaching right now. It’s really important to understand that masturbation coaching is not an ‘entertainment’ service; it’s not a mutual experience where I (your coach) am also masturbating, or a role-play situation where I’m the ‘strict teacher telling you what to do’, or a one-off experience without structure or integration. There is absolutely nothing wrong with wanting those kind of experiences, it’s just not what I’m offering here.

Coaching is a process that you commit to – I recommend a minimum of three sessions – that leads to change in your experience and relationship to a subject or situation. It focuses on the ‘here and now’ rather than on the distant past or future (a therapeutic process, for example, is often more focussed on your past experiences). A coaching process is designed to help and empower you to improve and change your own experience.

Before we embark on our masturbation coaching journey together I’ll ask you to fill in an intake form. This gives me some background on you and your current relationship to sex, masturbation, arousal and your body. It also helps you to start calibrating why you want to commit to the sessions and what you want to get out of them. From there we have an intake call: 20-30 minutes to ‘say hello’, for you to ask any questions you might have and for me to begin to get a sense of you, and what we might actually include as content. This call doesn’t involve any nudity or masturbation and is held on Zoom, a video call platform. All calls are confidential, not recorded and accessed with a secure meeting ID and password (given only to you and me). This is the same platform and process we use for the actual coaching calls. After an intake call we will agree a date and time for your first coaching session.

Why don’t we just do the masturbation and witnessing straight away after the intake form?

Two factors: impulse control and building a rapport. See my previous points about what masturbation coaching IS NOT… Rather than impulsively diving into a one-time ‘masturbate on screen’ fantasy, I’m encouraging you to commit to a learning experience. This involves building a sense of trust in me, your coach, and the ‘container’ of the sessions. Many clients say to me on an intake call that they feel nervous, apprehensive, over-excited or uncertain about the process. Getting that out of the way, and having some time between the intake call and the first session, means you can be a little more relaxed as we move into more intimate, vulnerable learning experiences.

So, what happens in a virtual masturbation coaching session?

During a typical first coaching call we usually begin with a simple ‘check-in’ – how you’re feeling that day: anything that you are aware of in terms of physical or emotional sensations in your body. I then introduce a ‘warm up exercise’ – this might involve things like…

  • focussing on your breath and trying out some different ways of breathing
  • or exploring different types of self-touch in a non-intimate part of your body like your arm or chest
  • or exploring some simple movements to help you relax tension and tightness

These exercises vary from client to client are dictated by what I believe will be helpful to you based on your intake form and our intake call. We chat about what you notice during these exercises: how it feels, what kinds of sensations you are aware of in your body etc. We then spend anywhere from 20-30 minutes in ‘masturbation witnessing’.

What is masturbation witnessing?

Before you begin we agree on how long you will spend on the practice – it might be just 5 minutes to begin with. You then set up your space (usually your bed, a sofa or some cushions and blankets on the floor) and get comfortable. It’s helpful at this stage if your laptop/phone camera is placed far enough away from you so that I can see most of your body and get a full impression of the position you adopt, how you move and how/where you touch yourself. The space and position you are in should be as accurate a representation of your usual habits as you can give: it’s not a performance and there isn’t a ‘right or wrong’ way to do it. So if you usually masturbate under your duvet, that’s how you should set up. If you usually masturbate sitting at your desk that’s the position you should be in.

Once you’re comfortable you can begin: enjoy your masturbation experience as if I were not even there. I don’t interject or guide you during the experience, I simply witness and observe. Do whatever you would usually do: if you usually watch porn then include it in this practice, if you usually use toys, lube or oil then include them in this practice, if you usually orgasm or ejaculate then that’s welcome in this practice.

I will let you know when the agreed time is coming to an end. When the practice time is up I will encourage you to take a few moments just in stillness and quiet to let the experience install. Afterwards you can share what you felt, how the experience was for you, what you enjoyed, what was challenging or distracting etc. I then offer feedback and suggestions, based on what I have witnessed, to help you shift out of the habitual or try something new. This then forms your ‘homework’ – to try out the new elements I’ve suggested during your ‘mindful masturbation’ practices between our sessions.

Masturbation homework...

This is an important part of the process, and probably the best homework you will ever have been set! Sustainable change in habits and behaviours comes from gradual adjustment and regular practice over time. If you are willing to do your homework and commit to a daily ‘mindful masturbation’ practice you will experience far more effective change in your relationship to pleasure and masturbation. It’s really the same as learning a musical instrument: if you just have one piano lesson a week and do no practice on your own it will take you much much longer to become a proficient pianist!

Subsequent sessions are structured in a similar way to an initial session: they will often include a portion of the call spent in ‘witnessing’ so I can continue offering reflection and new options for you to explore. You will probably notice that you become more aware of your habits and patterns just through the experience of being witnessed – you will pick up on things you are doing/not doing without me having to specifically name them. This self-reflection and curiosity are valuable tools to take into the rest of your life. The more you are able to be mindful and aware of your actions and choices, the more freedom you have to make those choices based on the ‘here and now’ rather than your historical conditioning.

Here’s what some clients had to say about their online coaching sessions:

‘I began learning about Tantra 6 years ago when I retired. With Covid, my trips to in-person Tantra teachers stopped, and I went on line to learn more. Then I found Libby. Having worked with other practitioners, I must say Libby is among the very best, even with the ‘unusualness’ of an online setting.’ – Bob, New York, USA

‘Libby listens, and watches, and then makes wonderfully helpful suggestions. She is sincere in her interest in your success. She has so improved my experience of bliss. She took me from where I was a moved me well down the path of true pleasure. I experienced sensations and touch I never dreamed possible, and wish all humans could experience such joy, pleasure and happiness.’ – Simon, Paris, France

‘I highly recommend that anyone who is interested in experiencing more pleasure, more juiciness, more happiness, an improved relationship with a partner, and a connection with their body and the universe, should consider sessions with Libby.’ – Emily, West England

If you’re interested in these sessions please get in touch via email ( with your completed intake form (CLICK HERE) and any questions you might have.

With Love,