Dear Alice,

I have a friend who moved away for college whom I have kept in touch with. We are very open with and trusting of each other, and we've started to communicate in-depth about sex (fantasies, masturbation, but we're both virgins). We've had cyber sex through text but lately we've moved on to the idea of using video chat to watch each other masturbate. I'm excited about the possibility, and he seems to be, too, but I have some concerns:

Am I being naive and letting too much of my guard down? Is this kind of experimentation natural and healthy? Should I "prepare" in any way (shaving, "practicing" in some way)?

Thanks for any advice you can give me!

-Adventurous Virgin

Dear Adventurous Virgin,

You’ve asked some great questions about venturing into the arena of video sex. Exploring your sexuality and sexual interests is definitely natural and healthy. It also sounds like you have found someone you feel safe with and the two of you are learning together — here are some tips to help maintain that open and trusting relationship and tackle some of your concerns if you decide to go live:

Check in early and check in often. Concerns about letting too much of your guard down may be alleviated by talking about boundaries and desires in advance. Ask yourself some questions about what you want, don’t want, and even what you’re unsure about. Then, bring your friend in on the conversation so you both can be on the same page. Here are some questions for you and your friend to consider:

  • What type of ground rules do we both want for our sexual relationship and our friendship?
  • What about other people? How do we want to handle communicating about potential relationships/sexual encounters with others?
  • What about a safe word? Safe words are typically established to alert partners to slow down or stop during sex play. Use a word or words that won’t be confused with the sexual content of the moment — like “red” for stop, “green” for keep going, or “yellow” for slow down. Safe words can also be integrated into your sexy communications via text, phone, or video chat.
  • What are your turn-ons or turn-offs?
  • What can make us both feel safe, respected, and comfortable as we consider our on-screen debut?

Answers to these questions may shift over time — try to be up front with your friend and touch base from time to time to discuss if either of you feel differently or have changed your mind about your initial agreements.

Consider cyber security. The reality of the internet includes computer hacking, viruses, and other avenues that may lead to your private time becoming more public than you intended. Consider talking about ways to secure your exchanges. Some issues that you may want to discuss:

  • Try to avoid showing your face and your body on screen at the same time — it’s harder to identify a person without the whole picture!
  • Check out the security settings on the program you use to communicate with your friend — some may be more secure than others.
  • Saving your chats and/or videos? Consider saving them with a file name that will remind you not to send them to the wrong recipient, e.g. “do not send to anyone other than XXX”. Also consider saving them on a private/personal computer and using document or folder security option might also prove helpful.
  • Consider the security of your internet network, too. Using a password protected personal network provides more security than a public network or a network without a password.

Prepare to be prepared. There are lots of ways to get ready for a video debut — and preparation can be a great way to relieve some of the nervous anticipation leading up to a new adventure! Here are some possibilities:

  • Talking about how to prep may even build additional excitement for you both!  Since you’ve already established an open dialogue, you may want to discuss aesthetic options like shaving and what clothes to wear (if any).
  • Consider recording yourself ahead of time or use a mirror to plan for positions, angles, or even just to get a sneak peak of what your friend will get to see. That said, sexual adventures are often somewhat unpredictable which can certainly be part of the excitement! So, it might be best not to worry too much about planning your every move.
  • Want to learn more about masturbation (solo or with a partner)? Check out stores like Babeland or Good Vibrations for helpful books, guides, and toys. You can also peruse the Go Ask Alice! masturbation category.

In your question, you ask if this type of exploration is normal and healthy. For some, this type of dynamic found within a friends with benefits situation or other types of uncommitted or non-romantic sexual relationships can be liberating and exciting. They may also be more common due to the number of available and semi-anonymous forms of technology at our finger tips — like photo sharing, video chats, and texting. Exploring your sexual self with a particular distance afforded by various types of technology may allow for unique understanding and expression.

Considering new sexual acts or interests may also bring up unexpected questions or feelings. If you’re feeling unsure about the nature of your relationship or even the type of activities you’re considering, talking it out with your friend or another supportive person in your life may be helpful. Many people also begin to understand their sexual selves more fully with the guidance of a counselor or sex therapist. You might also be interested in speaking with a sex therapist through the American Association of Sexuality Educators, Counselors, and Therapists.

No matter what you decide, Adventurous Virgin, try not to rush yourself — it’s perfectly healthy to allow yourself the time and space to explore any questions or reservations fully before/if you decide make plans for your video date. Hope you have fun on your sexy journey!


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