I pedaled a local daily newspaper during 1958-60, my last two years of high-school. Every other Saturday afternoon I'd 'collect' my route. And I was a horny seventeen year old boy at the time this experience occurred.
Mrs. Smith lived in the two-story yellow house on the corner behind the football field concession stand. Her husband had died five or six years earlier, her sons were grown and gone, and she was alone now. She'd always treated me nicely, and had always paid her newspaper bill on time.
On this particular hot Saturday afternoon in July she invited me into her foyer as she hunted for her newspaper payment card. Her house had A/C, quite uncommon at the time, so I was more than happy just to stand there and cool down for a few minutes.
Mrs. Smith was a vey pleasant 50-55 year-old somewhat chunky lady with a nice smile, and a very friendly 'mom-type' manner. I'd never really thought of her in a sexual way, but I surely did this day. Mrs. Smith had very large and pendulous breasts that were on that day covered only with a thin but tightly-stretched man's sleeveless white t-shirt. I never seen them with such clarity, and I'd never seen her bra-less. The t-shirt clung to her so snugly that it seemed she was almost naked. It was tight enough to clearly display her large nipples and her almost saucer-sized areolas. Although she was still searching the dining room chest for her payment card, what I'd seen in the foyer had instantly hardened my adolescent penis so much that it had poked its way through the fly in my briefs and was now tenting my satin baskball shorts directly!
Mrs. Smith recognized my situation instantly and smiled at me as she returned from the dining room with the payment card. She stared at my satin tent, as I stared at her monster breasts through her t-shirt. She blushed, and I expect that I did also. We both seemed quite embarrassed.
To break the ice on this subject perhaps, as well as to cool things down a bit, she offered me a glass of lemonade. I accepted, and we sat down facing each other in straight-backed chairs that we'd pulled away from the dining room table.
Ms. Smith's beautifully heavy hanging breasts bulged out her t-shirt as they rested on her stomach, and my own 'post' held up the satin tent in my lap. We both looked at these parts of each others bodies. I was generating so much precum that it had soaked through my satin basketball shorts and formed a large wet-spot right there in my lap for her to see. My embarrassment had passed somewhat, however. I felt almost glad the enlarging precum spot was there so she could see how she'd excited me. I was almost proud of it. This was a strange new feeling for this young fella!
'Tom, I see you're perfectly normal. Please don't be embarrassed. My sons are grown and gone now, but when they were your age they were constantly aroused by almost anything, even these big milkers of mine. They frequently had to relieve themselves several times a day. Sometimes they spent so much time locked in the bathroom that I thought something was medically wrong. It was only later that I learned that teenage boys, like yourself, have to masturbate several times a day to relieve themselves. Your young bodies make so much semen that you have to have frequent release. And, since my husband has been gone, I've longed for the sight of a man taking care of himself. You're obviously excited by my breasts. I could show you my breasts, in fact I'd like to show you my breasts, and you could take out your penis and show it to me, and how it works!'
Talk about excited! I'd never ever seen real bare breasts before, and this lady with her huge breasts was telling me that she'd show them to me and let me jerk-off to them. I either grunted or nodded or both in response to her offer, I honestly can't remember.
Mrs. Smith reached down to her waist and pulled up the white t-shirt until it covered the lower part of her face. Then she straightened up in her chair and held her chest out toward me. I'm no expert, even now many years later, but they had to be at least 44-46 DDs or EEs. They were absolutely massive. They hung below her navel as they flattened out across her chest somewhat. My eyes were glued to them. 'That's ok, Tom, that's what they're for, enjoy yourself, look all you wish!' Her nipples were fully erect, and her areolas were thick and dark. Here and there on her beautiful breasts were fine blue veins like those on a road map.
'Well, Tom, say something, or do something, I'm showing you mine, now please show me yours.' My satin basketball shorts have large leg openings, and since my penis was already out of my briefs, I just reached up inside my satins and pulled out my penis. She looked at it and smiled and told me how long and thick it was, and how beautiful the head was. She commented on the precum being smeared all over it and said, 'Look what I did!'
I looked at her big bare hangers and told her how beautiful and big they were, and that this was my first time actually seeing real live bare breasts. I told her that I wished I was her baby so I could nurse at them. She smiled and nodded at that. I told her that I just wanted to look at them and rub my penis until I ejaculated.
'You're young, Tom, and I know you won't last long. You're welcome to stand up here in front of me and squirt your semen all over my breasts when you cum. Don't worry about a mess, we can wipe it up. I really want to feel your warm semen spurting out on my breasts.'
I stood up and leaned over toward her, pointing my penis at her wonderful titties. The head of my penis was not more than a foot from the part between her lovelies. 'I'm gonna ejaculate, Mrs. Smith, my stuff is gonna come out.'
'That's fine, Tom, that's what I want. Milk it out on me. I want to see it and feel it. Let it come out, it's okay.' That did it for me, right then and there. With three more strokes of my right hand, my semen flew out over her beautiful bare breasts in six to nine streams of warm whiteness. She smiled up at me all through it, peeking out over her raised t-shirt. She thanked me when it was over. Then she wiped my semen from her breasts with tissue from the dining room table, and we both sat there and rested just a bit. She paid her newspaper bill, and I left.
Although I saw Mrs. Smith two times a month afterward for newspaper collecting purposes, we never once mentioned that July afternoon when she showed me her sweet breasts and invited me to masturbate to them and on them! But I'll surely never forget the experience. Even today, large pendulous breasts are my very favorite.