I've been fortunate to have had experienced these sorts of phenomena twice!
The first time, it was my final year in secondary school (Senior in High School) and my English teacher had the habit of discreetly pressing a hip or a breast against me at opportune times. She was an athletic redhead in her early 50s, with a nice hourglass figure and soft C-cup breasts shaped (fascinatingly enough) like bananas. She seemed to wear low-slung demi 1/2-cup bras, so her breasts would occasionally jiggle and wobble ever so slightly without being obvious.
There were times where myself and other students would be standing with her behind her desk whilst she demonstrated some writing technique. Inevitably, she'd arrange things so I'd be standing on her left. She would point out something specific and would suggest we all lean forward to get a closer look, at which time she would "innocently" shift her footing and press her curvy hip against me.
This happened several times over two semesters. The final time, instead of her hip, she pressed her left breast into the back of my right arm. I could feel where her breast was bare under her dress, and where the lacy top edging of her low-slung demi bra started. Whether it was her hip or her breast, she would just continue pressing against me for what felt like a full minute as she continued with her informal lectures.
On occasion, she liked to use an overhead projector for presentations. I habitually sat in the back, and she always set up the project at the empty desk next to mine. Whilst other teachers would stand at these projectors in the middle of the class, she liked to sit at them in the back. As she was lecturing in a darkened classroom, she would start performing the sexiest shoe-dangling and barefoot flexing. She caught me countless times, out of the corner of her eye, ignoring the lesson and ogling her sexy performance which only seemed to encourage her! She is the primary reason I now have a foot fetish as well as an attraction to older woman.
Nothing ever came of it all, but I fantasised countless times of having a May-December romance with her. I never understood what she saw in me. I assume it was out of pity as she was trying to help a painfully shy student out of his shell.
~~~
The second time, which was a little over a decade after my teacher encounters, something similar occurred to me with a co-worker. There had been many months of innocent flirtations between us, and much of it was more like a genial sibling rivalry. We were both married to other people, so nothing further was in order. I came to realise things were more serious for her, which caught me off-guard completely. Things seemed to change a little between us, when she teasingly raided my break-room locker for embarrassing contraband. She found plenty in the form of a stack of library books about sexless marriage and vaginismus, which I usually studied whilst alone during lunch. Obviously embarrassed, she apologised and returned the books to my locker.
She was a zaftig blonde with a curvy, sexy shape just like Mandy2335 here on OCC.
https://forum.oneclickchicks.com/member.php?u=1711210 This lovely lady had DD-to-F cup breasts. I confess that's estimated as I never had the opportunity to see them
sans vêtements.
Perhaps a week after the locker incident, we were all standing as a group back in the storeroom, listening to a lecture by our boss. Out of habit, I always stood at the back of the collection of employees. Behind me came my favourite co-worker. She sneaked up behind me and discreetly pressed her huge right breast against my back. It surprised me, and I turned to look at her. She ignored my glances as if nothing was happening, and peered intently on what our boss was demonstrating. I returned my gaze back to the demonstration. But her lovely huge breast continued to press against me. Then she'd adjust a bit and her breast was pressed against the back of my left arm. Her breast was so soft, like the softest pillow in the world. She adjusted her breast again to my back. Her single pressed breast must have been 25-30cm (10-12 inches) in diameter. OMG! It was heavenly!
This went on for a good 5 minutes. The boss ended the lecture, and I felt that glorious breast leave my back. We all dispersed and went back to work. Nothing was ever said about it, and nothing similar ever happened again.
Upon intense recollection years later, I suspect it was her way of saying "I'm really attracted to you, and even love you just a bit. But we're both married and I have children. So this is my gift to you, given your marital difficulties. Keep your mouth shut about it, right!"
I confess that you good folks at OCC are the first to hear about this. No one else knows, besides her and myself.