In elementary school my main tickling interests were aimed at girls my age, but from time to time I fantasized about adult women. Why? Mostly because of the role clothing plays in my tickling fantasies. I was, and still am, infatuated by the idea of women wearing clothes that feel ticklish. At that early stage in life the only label I had to define the kind of fabrics that caught my interest was "silk." It was much more common to see adult women in silk that pre-teen girls, and that explains in part my occasional interest in what were then much older women.
Another angle not to be overlooked is the typical boyhood crush on a female teacher. "Teacher" is too constricting -- sometimes with me it was not really a teacher, but what was always a factor was the role of mother-like care giver. What comes to mind specifically were some Cub Scout den mothers. Never MY den mother (too close to "home?").
One specific fantasy I created while still in elementary school, say around the age of ten, involved a teacher who was relatively young, with a great figure, very loud and fun and outgoing, and best of all single. She never wore silk, but I had no trouble imagining her in some. The other key player was a bright, ugly, snotty girl in my class. The one who always got straight A's and who whined about anything anybody did that offended her. Dennis Mitchell's Margaret. Nobody liked her.
One day she falsely accused someone of some minor infraction of the rules and demanded punishment from the teacher. When enough people vouched for the accused our teacher decided that this girl needed to be taught a lesson. Her punishment was to be tickled in front of the whole class.
Here is where my preferences differ so much from the "mainstream" tickling community (if one can make a claim that there is such a thing!). I did not picture her held down while the class took turns tickling her feet, or tied to a chair even. No, my feverish brain has always devised far stranger methods, and as unlikely as they may sound to you they are the stuff that whips me into a sexual frenzy.
In the scheme I concocted our teacher was a devoted tickling enthusiast, and for this occasion she decided to apply her knowledge of tickling to punish this terribly obnoxious girl. She owned a dress that she enjoyed wearing at home, a dress made out of the most wonderful silk, the kind that felt unbearably ticklish. It was a simple sleeveless knee length sheath with elastic in the waist. A pure, brilliant white. It's most outstanding feature other than the fabric was that it was pleated. The pleats were about a quarter of an inch deep and ran from the neckline to the hem. I actually patterned it after a number of such dresses I had seen women wearing. When this teacher was in the mood for a good tickle she would strip naked, slip on the dress and walk around the house while the pleats brushed against her skin until she couldn't stand it any longer. In my young but highly imaginative mind I pictured the sensation a being extremely ticklish, so intense that she could never stand it for more than five or ten minutes.
(Fantasies have lives of their own, and in this case I sometimes made the teacher's outfit a jumpsuit rather than a dress. The feature the jumpsuit added was better access to the teacher's cunt. What I find strange is that I have no recollection of seeing such a garment until I was in college; can you imagine my reaction? Anyway, the dress made the fantasy a bit more realistic, while the jumpsuit made it more exciting even though, as you will see in a moment, it presented a problem with the cotton underwear idea. The illustration I have drawn depicts the jumpsuit.)
On the day the punishment was to be carried out she brought this dress to school. With it she brought a simple cotton slip, several lengths of rope and a cotton smock for the girl. Her plan was to use the dress to tickle the girl while wearing the cotton slip under it to save herself. The plans she had for the girl required some assistance, and I was one of four boys she called upon to help. She met with us to explain the plan, and it was while she was briefing us that I saw an opportunity for some fun that I could not resist.
At the appointed time our teacher and the girl went off to change. When they returned the teacher was wearing the pleated silk dress with only the cotton slip underneath. (She had explained to us that she was not going to be wearing a bra or panties as this would intensify the girl's suffering. Why? Who cares! It was an expedient to make my fantasy work!) The girl was wearing only the loose fitting cotton smock.
The whole class went out to the playground, to where the tether-ball poles were. My first job was to shinny up one of the poles and thread two long ropes through the eye-bolt at the top. We tied the teacher's wrists together with one of the ropes, then pulled it tight until her arms were drawn up tightly over her head and her back was to the pole. Next we brought out the girl, tied her wrists together with another short length of rope, and hoisted her up and placed her arms around the teacher's neck so that the two of them were face to face. Still following the teacher's plan, two of us held her there while two others tied the ends of the other rope that passed through the eye-bolt around the girl's knees. When we were finished she was dangling against the front of the teacher with her chin about level with the teacher's shoulders and her legs drawn apart.
The next step in the plan called for me to use a pair of scissors to cut away the girl's cotton smock. This would bring the whole front of her body in contact with the teacher's pleated silk dress. Best of all, her wide spread legs would allow the pleats to brush against her cunt, which even at that young age was for me the ultimate place to tickle a girl. I loved to dwell on the prospect of the sharp edge of a pleat working its way into the poor girl's slit, which I believed would feel very good yet excruciatingly ticklish.
The moment I pulled the girl's smock away she let out a shriek and began to shake with laughter. The shaking only made things worse, as that caused the pleats to brush against her bare skin even more. The whole class let out a whoop of joy at seeing this snotty beast suffering so exquisite a torment.
I let things ride for several minutes, then decided it was time to play my trump card. I stepped up to the teacher, wielding my scissors, and her eyes grew wide with fear.
"What are you doing?" she demanded.
Without saying a word I gently lifted the strap of her silk dress, slipped the scissors under the strap of her cotton slip and sniped it.
"Oh no!" the teacher cried. "No! You mustn't do that!"
Still silent, I went around to her other side and cut the other strap. By this time the teacher was struggling mightily, but while it was impossible for her to free herself her gyrations did much to intensify the girl's torment. Sensing success in my grasp, I reached down under the teacher's dress and yanked down her slip.
Now it was the teacher's turn to let out a shriek. Hers was not so much one of surprise as of dismay, for she knew only too well what to expect.
The synergy of the two made the scene much more exciting. The girl's uncontrollable shaking caused her chest to rub against the teacher's breasts, flooding the woman with tickling far more intense than she had ever felt just walking around in the dress. The teacher's own struggles fed right back into the girl. The sweetest part of all was the way the girl's crotch rubbed against the soft mound of the teacher's belly, forcing the pleats deep into her slit. When I concocted this scene I did not know much about sex, but I knew I liked to rub my cock and that girls felt something similar in their cunt. After I knew what an orgasm was I liked to add that in, imagining the girl coming over and over from the pleats flicking against her clit.
I never bothered to work out an ending to this fantasy. I just ran the scene until my cock throbbed and drenched me with pleasure. If anything, I imagined that when we at last cut them loose the two of then fell in a heap onto the grass, still laughing but now at the unexpected but very much appreciated turn of events.
In closing, may I remind you that while such scenes are fine as fantasies, nothing remotely like that should ever be condoned in real life.