Loving an Older Woman

For as long as I could remember, I’d imagined that she had big boobs, but now that I could see for real, I knew that she did. Big, soft, rounded boobs with pale, almost white skin and pink nipples as thick as a finger, but only as long as one of my fingertips. Around them were pale pink areolae, as big as brandy glass but faint and smooth, barely discernible despite her untanned skin. But the most wondrous thing was that her nipples didn’t sit at the end of her breasts, hanging downward, but sat high above the fuller curve, pointing almost upward, straight towards my eager lips.

Her hand reached for mine again, lifting them back until I cupped her breasts, held them and felt their weight.

“And now? Are they what you expected?” There was something in her voice, an edge, as if she expected me to be disappointed.

“Better, wonderful, the best, magnificent,” I gushed, lifting my hands one at a time and watching the way the curves changed, feeling the weight and then pushing upwards until they formed the high cleavage that the bra had created.

“Saggy without the bra. It’s all underwire and padding that you see in the dress. That’s a lesson, what you see is often not what you get.”

“No, it’s better, far, far better. They’re, you’re, beautiful.”

Di blushed, it as if the compliment surprised her.

“You like them, old and saggy?”

“Their not old and saggy, they’re magnificent. Can I suck them?”

She nodded, and as I lowered my head, dipping my knees slightly, she gasped as I sucked a nipple into my mouth. I’d kissed nipples before, briefly, but this one felt larger, purposeful, as if it was there to be sucked, not just for ornamentation. I was eager now, trying to devour her tits, sucking as much as one as I could into my mouth, savouring it, then turning to the other, sucking that too with an open mouth, before relaxing, to lick and suck at her nipples gently, whilst I squeezed and fondled her breasts.

“Wow! That’s enough,” she said her hands touching my head lightly and pushing me away. “You’ll get me going.” There was a breathlessness in her voice, an eagerness, and hint of desire that seemed to surprise her. As I stepped back, she scooped up each boob in turn, eased it back into the red lace of her bra cups and guided the straps back to her shoulders. Suddenly her cleavage reappeared just as her magnificent boobs vanished from site. Through the lace of the bra, I could see the rise of her nipples. I reached out and touched them, a single fingertip touching each erect nipple ever so lightly through the red lace. Di sighed, a long drawing in of breath with her eyes closed.

Suddenly her eyes opened, and she looked up me, stepped forward and placed a hand on the front of my trousers. Unfailingly, she had landed with the palm of her hand on my erect cock and I felt her fingers curl around it, measuring its girth. Without another word, she moved closer, moving in until her lace-clad breasts pressed against my shirt. Her other hand joined in now, the two of them covering my complete length, fingers wrapping trousers and underpants around it as she squeezed the thick shaft.

“That’s not a disappointment either,” she whispered. Without warning, her hands gave a couple of sudden, quick wanks, and then it was all over. Di hung to me, her hands holding my cock as it pulsed and pumped spunk into my underwear. It seemed to go on forever, pumping, pulsing as my balls were drained dry.

I must have been about nine when I first saw Di. I didn’t know her as a person then, to me, she was just the woman who had moved in next door. Another adult that would come and baby sit me whilst my parents went out on as Saturday night. I guess she’d have been about twenty-two then, but that just made her another adult to me, in the same age group as my parents. Old but not as ancient as my grandparents.

I don’t remember even considering what she looked like, she was just another adult, some were fat and some were thin, some were old and some were very old. I guess I categorized her, if I did at all, as thin and old.

By the time I was in my early teens and starting to get interested in women, she was still old, but old and good-looking. She had long dark, red hair. Not ginger, not brown, but a deep reddish that was quite unusual. She was also pretty and frequently dressed in tight jeans that showed off her wide hips and tight arse. Normally a tight T-shirt did nothing to hide the fact that she had big boobs. Not massive, not sagging, but heavy, a good bra-full that pushed out her sloganized T-shirts. I remember one of those; it was two ducks, one rammed into the back of the other, and ‘Fly United’ as a slogan. Took me years to get the joke.

About the time I started to get erections and learnt to wank, she became one of my fantasies, along with a certain school teacher, who taught English and was tiny and cute. Then there was a presenter of a television pop music show that my mates and I all agreed was worth giving one, although we weren’t actually certain what ‘one’ was. But Di remained my personal favourite fantasy, especially after I looked out of my bedroom window one afternoon and saw her pegging washing out on her line, wearing just those tight jeans and a red lacy push-up bra. It might have been a bikini top, but to my eyes, it was a push-up bra, in red lace. She probably had red panties on as well, well, that’s what I imagined as I jacked off into half a box’s worth of tissues.

She didn’t babysit so often now. My parents rarely went out but when she did, I’d try to stay up as long as I could get away with just so that I could look at her close up after my baby sister had gone to bed.

Di had a husband, Shaun, but I don’t ever remember seeing much of him, except perhaps once or twice. A big, brooding bulk of a man with dark curly hair, that was big of muscles and short of words, at least that was how I characterized him.

Then I went to college, moved out of home, and discovered girls my own age. There were those that I liked, those that did, and some even wore red bras, just like my favourite wank fantasy.

I’d grown up myself now. I wasn’t broad and strong, and I wasn’t interested in sport, but I did enjoy cross-country running. I could run for hours, so I guess my stamina was pretty good, although I never got to test it during the few quick couplings I had with the few drunken girls that did.

Then came the Christmas when I went home and my parents had a cocktail party. It was for their friends, and neighbours. My sister and I were both there, and so was Di. She was much smaller than I remembered, but wearing a dress that showed off her incredible rack. I sidled and said ‘Hello’.

“Jamie! Ooh, haven’t you grown?” She looked up into my eyes as I looked straight down into her cleavage.

“A bit,” I stammered. “How are you?”

“Well, thank you, and up here.”

I lifted my gaze and realized she had the deepest blue eyes that I’d ever seen. I’d never seen eyes that blue, they were gorgeous, like the rest of her.

“I’ve not seen you for a while,” she asked, her voice a soft, contralto that made my stomach churn with desire.

“I’m at college,” I muttered, my gaze dropping back to the curves of her breasts that seem to be infinity interesting.

“And what subject?”

“English Literature.”

“Oh, I’d have thought you’d have been doing Maths, you know the study of curves and hidden areas.”

The joke went over my head. I glanced back at her eyes and saw that she was smiling. She looked down at her cleavage and shook her shoulders almost imperceivably slightly, but enough to make the lifted curves of her breasts seem to slosh from side to side. My mouth dropped open.

“You’ll catch flies,” she laughed, and her boobs jiggled with her joy. I looked up again and realized that she was playing with me. Her voice dropped to a barely audible whisper. “Where’s your bedroom? I assume it’s empty.”

“Top of the stairs, first on the left,” I replied.

“Thanks, Jamie, I’d love another,” she said clearly, and then emptied her glass and passed it to me. “Leave it a couple of minutes and then follow me,” she hissed, smiling. She turned and left. I stood there like a lemon, holding two empty glasses as the hum of other peoples’ conversation seemed to flood back into my ears, and Di’s pert arse vanished towards the hall stairway. It waggled seductively under the thin cloth of her dress.

I turned around. Nobody seemed to have noticed that we’d even been talking, so I walked into the kitchen, put our empty glasses down and then stared out of the kitchen window into the dark backyard. Had she really told me to follow her to my bedroom, or had I misheard her? Was she trying to seduce me like a modern Mrs Robinson? She’d known that I was staring at her tits and hadn’t been annoyed. Either that or this was some sort of trap to embarrass me and teach me a lesson. The girls I knew got really annoyed when they caught you staring at their breasts, even when they were almost hanging out in a most provocative way. I swallowed hard, rearranged my hardening cock in my underpants, and headed up to my bedroom.

The door was closed when I got there, so I quietly twisted the knob, opened it as little as possible and slipped inside. The second I closed it behind me, the beside light switched on. Di was standing beside the bed and, I noticed, the curtains had been drawn.

“Come here then,” she cooed seductively.

Unfreezing, I walked slowly towards her. As soon as I was within reach, she took hold of my wrists and lifted my hands, placing them on her breasts, so that I could feel them through the cotton of her dress and the lace beneath it.

“That’s what you wanted to do, isn’t it?” she asked.

I nodded, completely wordless, and squeezed gently. Her eyes closed, and she sighed as if she actually relished the sensation. We stood there for moments and eternity, and then her blue eyes opened again, and she looked up at me.

“Do you like doing that?” The question was clearly a taunt.

I nodded again, still lost for words.

“Best feel the real thing then.” Her hands lifted and pushed her dress from her shoulders. As I lifted my hand in shock, the bra straps followed, and as her fingers pushed them down her upper arms, her breasts lowered, their weight pushing the no-longer-supported cups downward. Finally satisfied that the straps were low enough, one at time, she slipped her fingers into her bra, cupped a boob and lifted them up and over the lace, to hang free and naked before me.

“Wow!” was all I could say.

I’d held her actual breasts, naked, in my hands, sucked and kissed her nipples, and now, with the touch of a few seconds, she’d made me cum like never before. The world swam before me and I swore that I would never settle again for anyone less wonderful than her.

“You’ll make some woman very happy with that,” she said, snapping me back to reality. Was that a hint of sadness in her voice? “Once she teaches you what to do with it, and how to slow down,” she continued, the advice not being lost on me.

She stepped back now, lifted her dress back to her shoulders, wriggled everything back into place and then walked towards the bedroom door, leaving me drained, wet and open-mouthed.

“Would you teach me?” I managed to ask as she opened the door.

She laughed. “I’m married. Clean yourself up.” The door closed and she vanished from sight.

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