I remember this story so vividly, it remains to this day a memory I masturbate to frequently. I was extremely shy as a boy of about twelve. Unexpected and inappropriate erections were commonplace for me and I was constantly using my books or a jacket or untucking my shirt to conceal the bulge that would appear at the front of my slacks whenever I entertained a sexy thought or caught a glimpse of a sexy girl, which was pretty much all the time.
My family was going to attend a wedding and my mother took me to buy my very first suit. She left me alone at the store with a saleslady while she continued shopping in the mall. The saleslady was about 40 years old, wore a business suit that barely contained her large breasts whose nipples were erect and showing through her blouse and jacket.
Needless to say, my erection was throbbing and pushing against the front of my pants, which I covered with my baseball jacket, the moment I saw her eyes gaze down at my middle.
She just smiled and told me to take the suit she and my mom had picked out into the changing room and that after I'd put on the suit, to call her and she'd come in to make markings for alterations.
As I lowered my pants, I could see that my penis, which was tenting my white BVD's obscenely, was already leaking precum into the cotton, darkening it and revealing the shape of my circumcision clearly.
Pulling up the suit pants, I tried re-adjusting my penis to a less prominent position and zipped up just as she knocked and entered.
'A little long,' was all she said, and for a moment I wasn't sure what exactly she was referring to, the pants or the bulge my penis made next to the fly as she knelt down with a sliver of soap which she proceeded to use to mark the hem of each pant leg.
From her kneeling position, she brought both hands to the waistband of my slacks and gave a slight yank away from my belly to test the fit, her closeness causing my erection to throb and twitch quite visibly.
'You'll have to take these off,' she said, her face a little flushed. 'I need to see if these slacks belong to this jacket.'
'Take my pants off in front of you?' I asked.
'You're wearing underpants, aren't you?' I nodded. 'Well,' she continued, 'you mustn't be embarrassed. I've seen far too many boys your age in their underpants for it to be anything to get upset about. It's just part of the job.'
'You want your new suit to fit nicely, don't you?'
I didn't have a good answer, so I put my hands down to my sides as she unbuckled my trousers and lowered them to the floor, my erection pointing straight at her, poking against the white cotton exactly at eye-level.
She acted non-chalant about it, but the way she was squatting now, I could see up her skirt to her thin, flesh colored panties, her pink thighs and the garter-belt that held up her stockings.
It was all a bit much for me and, as the heat rose to my face, I looked down to see that the wetness from my precum, had so soaked my underpants that they had become almost transparent and the redness of head of my penis was visible.
Reaching for my pants by putting both arms around my legs, she seemed to be checking a tag along the seam. 'Nope,' she said, 'these are the matching pants.'
Once again, she slowly raised the trousers, her breasts brushing against my drippy underpants in the process. I was so close to ejaculating, I reached out and held on to her shoulders to keep from losing my balance as she hugged me to her breasts for a brief moment.
'Th-thank you,' I stammered, not knowing what else to say, but at that moment I saw she was staring intently down the front of her blouse. I followed her gaze and to my horror, noticed the big stain my wetness deposited in a six or so inch smear on her blouse between her breasts.
'Hmmm,' she mused, 'it looks like someone has a big problem.' with both hands resting flat on my thighs, she proceeded to slide them up towards the tent made by my erection in my underpants.
At first, I thought she was going to take them off or slide them down, but instead, she just held me through the soaked cotton, her fingers wrapped around the outline of my shaft, her thumb rubbing round and round the head.
I wanted her to take them off while at the same time, I was terrified we'd get caught. As it turned out, she had no such intentions and must have been thinking the same thing.
But that didn't stop her from her ministrations and within seconds, I was gasping for air and groaning as the first contractions of my orgasm began to swell the head of my cock as she stared at it, her face just as red as mine must have been.
Her other hand held my buttocks and suddenly I became aware that she was rubbing the crotch of her soaking wet panties against my shin as she watched my penis twitch several times and then the semen bursting through as it pulsed against the fly of my undies with each spurt of my ejaculate, spreading wetness across my whole groin at the very moment her own orgasm began, her groans added to mine in the small, hot room.
There's more to this story, but at the moment, I'm going to have to masturbate, this always happens when I think back to this incident.