Stories on this site about humping caused me to remember this activity from my younger days...
I have long enjoyed the look and feel of pretty, silky lingerie on my lovers and on myself. I started trying on feminine clothing when I was quite young, long before I learned to masturbate. It was only later that it became connected with any sort of sexual activity.
I learned early how nice the silky panties and slips that my family members routinely wore felt and I loved trying them on whenever I could when alone long enough in the house to play.
After my first actual sexual feelings, I began to associate wearing pretty lingerie and other feminine things, too, with the feelings of sexual excitement. By the time I had passed puberty, I had learned how nice it felt to have my erect penis rubbing against silly panties within a silky slip. The wonderful feeling of these garments sliding against each other were a small slice of heaven!
I learned how enjoyable it was to be fully dressed as a girl, routinely putting on a bra, panties, girdle, stockings, slip and dress or skirt and spending time walking around, feeling the movement of my skirt around my legs. Practicing sitting, crossing my legs, and imagining what it must feel like to actually go out dressed in such finery was grist for the mill of my imagination.
The humping part was just wonderful. I loved lying on my tummy in my dress, slip, panties, hose, etc and feeling the slippery friction of my erection against the panties sliding along the slip.
I would do this while building my fantasy in my mind of myself as the girl wearing such things and doing whatever I had her doing in my mind. The problem was when the slip would inevitably hike up as I humped within my skirt. I would suddenly lose that silky, slippery feeling as the friction increased instantly.
I would have to get up and reach under my skirt to pull my slip down to continue with my delicious fantasy. It could be interrupted many times during a session and was very frustrating.
I hit on the solution of putting a slip on a pillow and humping it. I could keep my panties on and keep rubbing against the slip and keep it under control. Besides, the slip on the pillow began to resemble the shape of a woman's hips and thighs in my imagination, adding to my fantasies.
In any case, it worked out pretty well and I had a lot of very nice orgasms that way,
Hmmm... I think I'm going to slip into a new outfit that I just bought... A slim black pencil skirt, pink sweater, stockings, heels, and a pretty half slip under my skirt. Makes me quite hard to think of what a wonderful time I will have humping a pillow and remembering other times...