Side-by-Side Self-Pleasure Challenge

The Recipe Rules of the challenge Both of you are lying or sitting next to each other. You must focus on your own pleasure: the goal is to enjoy your own body and touch without worrying about pleasing the other...
24 Jun. 2026
Couple ChallengesIntermediate
Side-by-Side Self-Pleasure Challenge

The Recipe

Rules of the challenge

Both of you are lying or sitting next to each other. You must focus on your own pleasure: the goal is to enjoy your own body and touch without worrying about pleasing the other person. Hands stay strictly on your own body. No penetrative sex allowed. Of course you can talk or watch your partner. You also use sex toys if that makes self pleasuring more enjoyable!

What you need

Tips

  1. If you feel shy try it first in the dark. Just hearing the sounds can be incredibly hot.
  2. Start fully clothed. Slowly removing your clothes builds anticipation
  3. Talk about what you’re doing. Describe your sensations or what you wish you could do to your partner, it keeps the tension high.
  4. Position yourselves intentionally. Side-by-side, facing each other, or sitting across from one another, whatever feels hottest.
  5. Don’t rush your pleasure. The whole point is to enjoy your own touch, without pressure to perform or “do something” to the other. Make the challenge last as long as you can.
  6. Use lube. It makes everything smoother.
  7. Journey before destination. This is about pleasure and connection, not orgasm.

 

 

Are you curious to see how it went for us? Watch the video of us taking on this challenge here.

 

Rating

What James loved

I usually love watching Lola pleasure herself. I get to see her taking care of her pleasure exactly how she likes. I love watching that and learning from her own touch. In the beginning it was incredibly frustrating, I just wanted to jump on her and have sex. And because I am more visual than her it seemed like a lot more of a challenge for me! But then I realised I could tease her just as much: by talking to her. So I started to tell her in details what I was feeling, how hard I was, what I would be doing to her next if we weren’t doing this challenge. It was so hot.

Why Lola loved

What I loved about this challenge is that it removes penetrative sex and instantly changes the dynamic. It brings variety without needing anything complicated. Seeing how turned on James was just by watching me pleasure myself was a reminder that desire isn’t only about doing things to your partner, but witnessing their pleasure can be just as powerful. It also quietly teaches your partner how your body really works: what puts you in the mood, what feels best, what builds pleasure. And the teasing, the frustration, the “you can look but not touch” part is incredibly playful. It made me feel deeply desired, not because of what I was giving, but simply because of my body and my pleasure. And that’s an incredibly empowering feeling as a woman. It gives me more confidence in our sex life.

Our Experience

We thought about this challenge while spending a few days in our wooden house in Portugal. We don’t go there often, but when we do, everything naturally slows down. There are fewer distractions and not much to do expect adapt to the stillness around us . It was summer, warm outside, and we had no real plans for the day. We wanted something different from our usual sex while keeping things simple and easy.

Slowly getting in the mood

We lay down on the bed next to each other, still clothed (well, as clothed as we are in summer at home 😅). We talked about the rules and, once we agreed on the “keep your hands to yourself” one, I was already thinking about all the teasing I was going to do to James. We took a few minutes to connect, kissing and settling into the moment. Then I lifted my T-shirt, and things immediately started to heat up.

Getting one of my favourite toy
I had recently bought a new toy, the Enigma Wave by Lelo. It’s an insertable vibrator that stimulates the G-spot through both movement and vibrations, with an air-pulse head that sits on the clitoris. The combination is pretty intense, so I don’t usually use it during sex — when we’re together, I tend to prioritise external toys so James can penetrate me at the same time. This challenge felt like the perfect moment to use it, since penetration wasn’t an option anyway. I grabbed it and started playing with it in front of James, who bent the rules a little, occasionally touching my nipples or caressing my leg while he was stroking himself.

An ending that didn’t go as planned

With the toy inside me, I started describing what I was feeling and how much I wanted him. Seeing James touching himself only made it harder to stick to the rules, and I caught myself openly telling him how badly I wanted his dick. At some point, I started begging him to break the challenge and just fuck me. He resisted at first, taking the rules seriously, which only made the tension stronger. Eventually, I managed to convince him and we both failed the challenge. Knowing that penetrative sex was off-limits made us want it even more, and we probably pushed the teasing a little too far…

 

 

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