She replied to my post interested in figuring out why she hasn't orgasmed during partnered play. She's 28, single, has a semi-regular FWB (once or twice a month), and occasional hookups. She's having a good time with partners but always ends up finishing herself off at home with a vibrator soon after. She was curious to unblock what might be holding her back and refine her FWB or future relationships with confidence in her own pursuit of pleasure.

The research

We chatted for a few days about what she enjoyed and fantasized about during her 3x weekly self-pleasure sessions, what brings her the most pleasure during sex, and when she feels like she has been closest to reaching orgasm. Sometimes there is a mental block from overthinking, other times it's about finding a good groove and sticking to it. We soon realized she had been going through the motions of various sexual positions but had never really explored the specifics and variations she really liked. By diving into specifics we theorized she might enjoy riding a cock similarly to the cone vibrator she used at home. She also learned about vibrating cock rings and other ways of integrating toys into the sex she's already enjoying.

In practice

She now had the confidence to demand more of her partners in pursuit of her pleasure. It soon became obvious one FWB wasn't interested in her pleasure or wants and he was dropped. A date turned into a hookup and went further than expected but she ultimately didn't get what she wanted (other than confirming her sexual appetite and refining her desires). It was time for a more considered approach to her pleasure.

Hands on

I offered to meet and she accepted. She wanted to receive a massage that would allow her pleasure to slowly build whlle she focused and allowed her to tune in to her emerging pleasures. She laid down on my bed, received a thorough massage, and enjoyed some fingering. i could tell I had found a good rhythm and continued the same strokes. She was both surprised and overwhelmed when an orgasm started rippling through her.

The orgasm confirmed a more fun version of partnered play was possible, she just needed a shift in partners and their interest in her pleasure. She could start to demand more as she dated in hopes of finding a relationship. She was freed from believing reaching orgasm was impossible.