Caught Mid Wank By Older Cleaner

* Note: everyone in the story is, of course, over 18 *

It was a Saturday morning. My parents were away on business, due back tomorrow. I'd had a long week of college, and last night I'd been studying hard for my exams. That morning, I'd woken up late, and as usual I had morning wood -- I was a teenage boy, after all. I always slept naked, so I didn't even need to slide my underpants down. I just pushed the covers to one side, stretched out across the bed, star-shaped, and then I took my cock in my hand. I started tugging slowly on my dick, thinking about my mom's friend Trudy. Now, Trudy was not an attractive woman, by any means. She had a slightly overlong face, and intense, severe features. But we'd all gone swimming recently on holiday, both families, and I'd been surreptitiously checking Trudy out in her swimming costume. At this point I liked slim, skinny women, with small breasts and tight bottoms, and Trudy was definitely that. While talking to me in her bikini, Trudy had taken an involuntary glance down at my trunks, as if checking out whether my cock had stiffened in reaction to her. That quick little glance had really fuelled my imagination. As I gently tugged on my dick, I thought about her taking a shower after a swim. I pictured her small tits, erect nipples, and (I imagined) clean-shaven pussy. My balls tightened, I sighed loudly, and I started settling in for a relaxing and (in my judgment) thoroughly well-deserved wank.

And then something happened that changed my life forever.

The door opened.

It was our cleaner, Barbara. She was in her late sixties; a cheerful, weighty woman, with big breasts and an even bigger smile. Barbara had always come on Mondays... somewhere in the back of my mind, I suddenly remembered that she'd changed her day this week. And I'd forgotten. And now, she was standing in the doorway, mouth open. Her gaze immediately locked on to my cock. She gasped.

"Oh my goodness!"

I was so shocked, that it took my brain a moment to catch up. I actually continued pumping my engorged cock for a few seconds, staring at her, before I came to, and scrabbled to pull the covers over my naked body. I could feel my face immediately burning with shame. My cock shrivelled and shrunk.

"Oh god Barbara, I'm so sorry. I've got no excuse."

Her mouth kept the O-shape for a few seconds, then she laughed. It caused her big breasts to jiggle, and she smiled at me warmly. "Oh don't be silly. I was just surprised! You're a young man, with all of those physical urges young men have. I'd be more surprised if you didn't have a good wank every day."

Hearing her say the word 'wank' was really quite arousing. I felt my cock tentatively stiffen again.

"I... I guess so. But still, I'm really sorry you had to see that."

She laughed. "See what? A handsome young man naked, tugging on his lovely big willy? Believe me, that was the highlight of my week!"

My cock stiffened even further at this, now approaching its full length.

"I... you.... You really don't mind?"

"Darling, of course not, I don't mind at all. We all do it! Even at my age, I like to give myself a good rub down there every now and then."

I pictured her touching herself, and the image, to my surprise, caused my cock to viscerally ache. She was still flashing me her warm smile.

"Now -- my late husband used to say that there was nothing worse than stopping mid-wank. He said it gave him something called 'blue-balls', whatever that is. So why don't you carry on, darling? Don't stop on my account."

She reached up to the top of my wardrobe, and started dusting. My eyes ran over her big bottom, as my mind raced. Was she seriously saying I should carry on wanking? Literally in front of her?

It all seemed a little surreal. Nevertheless, I started lightly stroking my dick under the covers, while I watched her clean. She wore one of her usual flowery dresses -- not too tight, but it didn't do anything to hide the shape of her body underneath. She had little 'love handles' at her waist, but most of her extra weight was around her hips and bottom, and of course her huge boobs. I suddenly realized I found her really erotic. Really sexual. Her dress was low cut around the bosom, exposing a fair amount of cleavage, and with the morning sun streaming through my window, I could see through it -- not fully, just slightly. Her bra was lacy, and expansive, and she wore a pair of what we used to call 'granny panties', which covered her entire ass. I wondered what she looked like naked, and as the images flooded my mind, I started tugging on my prick again. By now, it was once again fully erect, and I adjusted the covers to create space.

She glanced over at me again, and smiled encouragingly. "You know, you might as well pull back the covers, it'll be easier."

I stared at her. "You... you really think I should?"

She laughed. "Only if you want to, darling! But I've already seen your equipment, and I've seen you working on it. It's not like I'd be seeing anything I haven't seen before."

I thought about this. My cock was literally aching now. And I had to admit, now that I'd gotten over the initial embarrassment, the thought of her watching me wank felt really erotic. Still in a half daze, I pulled back the covers, tentatively, exposing my dick and balls to her. She smiled, encouragingly. "That's it! Now you can take care of yourself without all those covers in the way." I took my penis in my hand, and started tugging gently as she watched. She smiled even more broadly this time, putting her hands on her hips. "Go on luv! Don't be shy! Give it a good blast!"

I laughed, nervously. Then I looked down at her huge tits, and started wanking faster. She smiled at me, seemingly entirely at ease with the attention.

"That's better. Now -- I'd better get on with the cleaning."

She reached up to the top of my wardrobe and busied herself with dusting, while I carried on jerking my cock. I looked at her broad bottom, imagining what she might look like naked. I started to imagine pressing my hard dick against those big buttocks, and reaching around to grip her huge boobs. Occasionally she would look back at me, and smile warmly while looking down at my hand as it pumped my dick. Then she walked over towards me.

"I'm going to have to lean over you, dear, to get to the windowsill. Don't feel you have to stop, it won't take me a moment!"

As she leaned over me, I stared at her tits, while I quickened the jerking of my cock. A couple of her buttons were undone, and I was able to see clearly down her dress. There was some wrinkling at the top of her cleavage, but her boobs were magnificent, with big erect nipples that poked through the fabric of her bra. I swallowed, and my breathing quickened.

"You've got the most amazing tits, Barbara."

She looked down at me smiling. "Oh, thank you! My husband always liked them, too. He always said he loved a nice pair to grab hold of."

I stared at them, gripping my cock tighter, movements speeding up. "He was a very lucky man. They're beautiful."

Her smile broadened even further. "Oh you're so sweet!" She leaned in, and kissed my gently on the forehead. Then she rested a hand on my chest, and looked down at my cock. "And I have to say, you do have lovely big balls, and a gorgeous willy."

I stared at her, and swallowed. "You... you really think so?"

She beamed at me. "Oh yes! It's so much bigger than my husband's was, god rest his soul. You're going to make some young lady very happy." She patted my chest, then she drew back. "Now -- let's do some dusting under this chest of drawers." She turned around, and bent over, facing away from me. Her big ass was in the air, and I studied it as I wanked. Her dress was riding up, and I could just see a hint of the base of her big silky white knickers. I could see a light covering of cellulite on her thighs, but it didn't bother me at all; if anything, it made the sight of her gently swaying ass even sexier.

By now, I could feel my orgasm approaching; I imagined pushing up her dress, and pulling down her panties, to reveal her naked buttocks and tight pink asshole. I imagined what it might be like to fuck her from behind; to ram my dick into her pussy, slapping hard against those big ass-cheeks while I reached around to squeeze those lovely big soft boobs. She looked back at me then, studying the movement of my hand on my cock, her eyes twinkling.

"I wonder what you're thinking right now, you naughty boy!"

She shook her bottom playfully. The movement caused her dress to ride up even further, now fully revealing her knickers. They were riding up the crack of her ass slightly. The gusset of her knickers was too thick for me to see through, but I could just get the sense of the shape of her lips underneath. I could also see a few rogue grey hairs, peeking out from the sides of her knickers. By now, I was so turned on, so close to orgasm, that I unthinkingly blurted out the truth.

"I'm.... I'm imagining..... what it would be like to fuck your gorgeous cunt.... Aaahhhhhhh!"

I groaned loudly as my penis spurted four huge loads of cum, in thick ropes, landing first on my chest, then on my stomach, then over my hand. Barbara stood, stepped over, and rubbed my arm, smiling down at me as I ejaculated. She sighed, still smiling.

"That was so lovely to see, dear. Look at how much there is -- you must have really needed that! Now wait there, I'll be right back."

She walked out. Maybe twenty seconds later, she came in with a flannel in her hand. She wiped it first around my chest and stomach; it was warm, but not hot. She'd clearly put it under the mixer tap, carefully checking the temperature. Then, she wiped my hand, my balls, and finally my cock -- finishing by circling around the ridge of my bell-end, something that made me gasp. She stood back, and surveyed her handiwork.

"There -- nice and clean. I bet that was a relief! Now I'll go and put this in the laundry, and you have a lovely snooze." She smiled her broad smile again, looking at my spent penis, almost wistfully. "I'll be back on Tuesday. And if you're feeling horny again, you can wank as much as you like -- OK?"

"Thank you, Barbara. I'm... sorry I swore, when I... when I came."

She beamed again. "Oh darling, don't think twice about it. You were just about to empty your balls! My husband used to say all sorts of rude things when he was giving me a good seeing to, there's nothing to be ashamed of."

My cock twitched slightly. 'Giving me a good seeing to'. I really liked the sound of that. But I was suddenly nervous again. "You promise... you won't tell my mum?"

She winked at me. "It's our little secret, dear. See you on Tuesday!"

She glanced down at my spent cock one more time, her smile never wavering. Then she turned and walked out, closing the door behind her. I lay back on the bed, trying to compute what had just happened. It had been the most erotic experience of my life. Having this weighty but attractive older woman watching me wank, knowing that I was imagining what it would be like to fuck her? It was incredibly exciting. And the sight of her cheerfully wiping the semen from my balls and cock was almost heartbreakingly sweet. I knew in that moment that I'd never give a second thought to skinny, austere women like Trudy again. I would forever be a fan of cuddly, cheerful older ladies, like Barbara.

I tentatively stroked my dick, and felt it stiffen slightly. I wondered how much further Barbara would go. She didn't seem to mind me looking at her. She didn't think twice about wiping my cock and balls with a flannel, either. I wondered if she'd let me feel those big, soft tits? Or maybe squeeze her broad bottom? My cock, amazingly, was now almost fully erect. I thought about having another wank -- but I quickly decided no. I remembered her saying how impressed she was by the size of my load, so I decided to save my semen for her.

Staring up at the ceiling, still holding my dick in my hand, I started hatching a plan...