I have sweet memories associated with this position I started dating a girl in the military in my early 20 s . I learned a few weeks into dating that she was a virgin at 20 yo . We took our time over the next couple months getting comfortable and building up our relationship . It turned out that not only was she virginal , she hadn ' t yet had an orgasm in her life , how is this possible ? I still don ' t understand . I insisted that she let me teach her how to masturbate . So one fine morning , we assumed this position resting against my headboard , and I held my hand over hers as we stimulated her . She ended up squirting ! She was horribly embarrassed , though I assured her that this was a fine result . We dated for nearly two full years before I rotated out . and one of the highlights of my sexual career