I got accidentally caught just once by my gran while wearing her knickers after that it was always deliberate.
In my early pubescent years, in the 1960s, I got fascinated by sneaking peeks up my gran's dress whenever I had chance. It was an irresistable question - what was she wearing today Was it her big pink bloomers that covered half her thighs, or was it a standard pair of white knickers - what we would now call full briefs - with their tight, white gusset and allowing a view of her girdle with stout suspenders holding up her stockings
To give myself the maximum opportunities, I used to visit gran regularly and offer to do chores for her. It was surprising how many chores could be found that involved working near ground level in the vicinity of my gran!
One day, when I was sixteen (gran would have been about seventy), gran fell asleep in her chair while I was cleaning the windows indoors. I took my chance and slipped into her bedroom. After a few moments, I'd located and was exploring the contents of her underwear drawer. It was like an Aladdin's cave. Here was one of her girdles, a pair of her bloomers and several pairs of her knickers - not to mention stockings, bras and slips (petticoats, as we called them then).
I was trembling with excitement as I handled them, and overcome with a desire to wear these most intimate of my gran's garments. I must have been crazy but I quickly slipped out of my clothes and pulled on her girdle. I took a pair of stockings and was thrilled by the sensation as I pulled them up my legs and fastened them with the suspenders. Then I selected a pair of her knickers and put them on too. Oh, the feeling of having my balls caressed by the gusset of her knickers - that most intimate part of her most intimate garment - that piece of her clothing that spent so much time in direct contact with her sex.
My cock was straining under the tension of her girdle and I had to release it. It formed an impressive (if I do say so myself) protrusion in the front of her knickers, forming a little damp patch as it seeped pre-cum. I desperately needed to wank, so I lay down on gran's bed and started to beat the meat.
I'd been going for a couple of minutes with my eyes closed, visualising gran wearing the clothes I was now wearing - her old cunt where my balls were in her knickers. Then the unthinkable happened - cutting through the fantasy running through my brain came gran's voice. "What on earth do you think you're up to young man"
I might well have leapt about a foot in the air with fright! My cock deflated at once as I tried desperately to say something - anything - to gran, who was standing right next to me with a look like thunder on her face. After what seemed like an eternity, I decided that honesty was the only possible way out, so I told her how I'd been so turned on by looking up her dress and that I'd been unable to resist getting up close and personal with her undies.
To my amazement, she immediately softened her attitude towards me. "That's just like your grandpa. He could never resist either. It's been a long time but perhaps I should try to handle this the way I always did with grandpa." With that, she climbed onto the bed, lay down next to me and took my flabby cock in her hand.
As she gently began to rub my cock, it quickly did it's usual thing and took on a life of its own. Within a minute it was back to its former self - stiff as a rod.
"So, you've been looking up my dress, eh It's obvious you enjoyed what you saw. Why don't you find out what it feels like under there too"
Nervously, I reached for the hem of her dress and began to slide my hand under it and up her nylon clad thigh. I already knew she was wearing normal knickers, so I was not surprised to come to the top of her stockings and feel her suspender pulling so tight. As my hand moved from nylon onto bare skin, gran's pace on my cock started to increase.
A few moments later my hand made contact with her knickers. She immediately parted her legs a little and her suspender lifted the leg of her knickers just enough for my fingers to slip underneath. I could now feel the light fur that covered her mons and my finger soon found the little dip that marked the start of the essence of her femininity - her cunt slit.
A little more exploration with my finger and gran started to groan quietly and deeply. She began to move her hips slightly, matching the rhythm as my finger began to move over her slit and back again. Her pace on my cock increased again. The tip of my cock felt as if it was on fire and I just managed to say "Gran, I'm going to ..." when my boyish baby batter erupted into the air. String after string of the stuff splashed over the girdle I was wearing and dribbled down gran's hand.
"There, that's better", said gran. I couldn't argue. I couldn't speak! "I'll clean you up, then you'll have some washing to do. I expect all my clothes to be cleaned and back to pristine condition before you go today." I somehow manged to say "Yes gran." and then added "That was wonderful." To which she replied, "Well, don't let me catch you like that again. Next time, just ask!"
Guess what Over the next ten years or so, I did ask - and regularly! And each time I asked, gran would deliver. More exactly, she would cause me to deliver - mostly in her hand, sometimes in her love tunnel and, just every now and again, in her mouth (best with her teeth out, by the way). What a woman!
NOTE: Did you remember to bookmark this page so you can find it again?