Penny For A Farthing

"I'm going to start paying back my arrears soon Mr. Farthing, I promise I am. I'll be getting a pay raise at work next month, and I'm trying to pick up more hours," Penny assured me, her voice dripping in sincerity and her eyes pleading as she looked at me through the screen as we video chatted.

"I'm sure you are, my dear. But right now that doesn't solve the problem of you still owing me lots of back rent does it? So, shall I come around at the usual time?" I asked, giving her the semblance that she had an option in the matter, even though we both knew she did not.

I could see the revulsion in her expression, plain and clear. She tried to hide it from me, but it was still there. Even after months of my regular visits, Penny still felt that same shame and repulsion. In truth it turned me on, knowing she hated it so much. It gave me a sick sense of power and excitement to be in control of her actions and make her do things that she really wouldn't normally willingly do in other circumstances.

"My daughter is home, I can't see you for a few days at least," Penny said, lowering her eyes. Her voice was changed perceivably now, the sincerity gone and replaced with humiliation.

My attention perked up at the mention of Penny's daughter. Jessica was all of eighteen years old and a damn sight more attractive than her mother, although she was still an attractive lady even at thirty-eight, especially to a self admittedly fat fifty-five year old like me. It's just a matter of fact that a mature woman can't compete with her teenage counterpart, no matter how hard she tries. Sorry if that sounds crude, but that's how it is.

"That's not good enough I'm afraid my dear, you see I will be out of town with my wife from tomorrow until Monday, and due to that it has to be today. So, shall we say 4pm?" I asked with a raised eyebrow, again making it seem like she had an option.

"Mr. Farthing, please," Penny started to beg and I saw the look I'd seen so often in her eyes since we'd come to our little arrangement about how she'd solve the issues with paying her rent. That mixture of hopelessness and self loathing which filled her blue eyes, making her look so beaten down and lost.

"Don't start all that Penny, I'm a very busy man. Now, if your daughter is home as you say, well, you'll just have to send her somewhere else for a while won't you?" I said with a chuckle, my jowls wobbling.

Penny looked wretched as she realised I wasn't taking no for an answer, and I felt a thrill pass through my whole body. I loved having this power over her, and seeing my tenant so uncomfortable as she contemplated her situation only served to make me more aroused.

"Mr. Farthing..." Penny began but I cut her off before she could say any more.

"Penny, all I want to hear from you is 'yes Mr. Farthing, 4pm will be fine' and then we can both get on with our day," I said sternly, giving her a harsh look that brokered no argument.

"Yes Mr. Farthing. I'll see you at 4pm today, I'll get my daughter out of the way somehow," Penny said, defeated. She couldn't even bring herself to look at me via the camera now, and I could see the tears wanting to fall from her eyes onto her cheeks.

"Good, now I must go, I have got lots to do. But I look forward to seeing you soon, oh and wear something skimpy my dear," I said with a twisted smile, just to rub in the humiliation for her and give myself another little surge of excited pleasure.

Penny didn't reply and I ended the call before she even could, feeling the familiar sensation in my chest. A different part of me much lower had its own familiar sensations too, as I thought about her slim body clad in some flimsy lingerie whilst she waited for me to arrive.

I laughed to myself as I started my car and prepared to head off towards my appointment with my bank manager. Now I'd organised my fun for the day, I would go discuss transferring my money to a new higher interest account and then eat at my favourite restaurant. I kept hearing that there was a cost of living crisis going on in the UK, but honestly, for me life had never been better.

The next few hours passed by without incident, for me at least, and I felt as happy as an overweight, middle aged man who soon would be fucking a beautiful woman possibly could. I had a broad smile on my jowly face and a skip in my step as I went about my business. I did make a conscious choice to not be checking my watch every ten minutes though, as they say a watched pot never boils.

In truth I didn't have much business to conduct, just a few phone calls to make mostly, which was good because I was somewhat distracted for obvious reasons. Mostly I spent my time in town doing a bit of shopping.

I'd promised myself a new suit, and thanks to my rather more than average proportions, I always have them tailor-made. My thinking is if you can afford it, why not? Besides, off the rack suits just aren't made for men who are five-feet-eight-inch tall, with forty-six inch waists.

After the fitting was done, and whilst the suit was getting made, I went across to the jewellery department and found a gift for my wife Edith. She is such an elegant woman, and I've spent a very happy thirty years married to her, with I hope another thirty to come yet, too.

It had been a good month or so since I'd last bought her something nice, so I chose a rose gold necklace with matching diamond earrings. They were expensive, but she's worth it for putting up with me being away so much. And I always get a lovely reward for my generosity of a big home cooked dinner, and a deep blowjob afterwards. That was something to look forward to when I presented her the gift in a few days. Today, however, I had something else to look forward to.

Those few hours between the video call with Penny and my arriving at her house passed by slowly for me as I shopped, although I'm sure for my tenant it only seemed like a few minutes before I was knocking on her door. Three quick raps followed, after a pause, by a forth as was my signature, letting her know it was myself who was calling on her as per our appointment.

It was 4pm on the nose when the door opened and I was greeted by the succulent sight of Penny wrapped in a thick fluffy bathrobe. It was pink with roses down the front which I found adorable, and I took a moment to look her over, admiring the swell of her breasts for longer than any other portion of her body. They were my favourite part after all.

"Good afternoon, my dear. I trust your daughter has found some way to entertain herself and you are alone?" I enquired with a smirk, my eyes finding Penny's own after I'd finished gazing at her shapely, but hidden, form.

I could see the discomfort written large on her face. Her eyes were downcast and her lips tightly pursed, her cheeks were also flushed slightly. I found it all very exciting, and it brought about a huge sense of power and enjoyment within me.

"She went out with friends," Penny said curtly, her voice low and unhappy. Still she wouldn't meet my gaze directly.

"Ah it's good to see there are still some young people in this world who actually meet in person, not just on social media," I smiled and licked my lips hungrily as I let my eyes fall back to Penny's chest again.

She didn't reply, but she obviously felt my eyes on her because she reached up with her right hand and clasped the robe, holding it shut. That made me want to laugh, especially given that she was just minutes away from removing it all together. It's amazing how ingrained some actions and responses are in people, so much so they do them without even thinking.

"May I come in?" I asked, then pushed past Penny without giving her any opportunity to invite me, or deny me entry. We both knew why I was there after all. Besides it was always best to remind her just who was in charge in our little dynamic from time to time.

Penny looked like she wanted to say something but she held it in check as I entered her home and walked straight towards the stairs leading to the second floor, where I knew from past experience the bedrooms were located. I didn't bother looking to see if she would follow me.

"So here we are again, my dear," I grinned when she entered her bedroom a few moments after I had, to find me sitting on the edge of her bed which had groaned in protest as my weight had settled on it, the mattress sagging alarmingly under my ample buttocks.

"Yes Mr. Farthing," the mature woman said with her head hung low and eyes on the floor. It made my cock swell to see her looking so wretched.

"Did you dress how I instructed?" I enquired with a cocked eyebrow, looking at Penny expectantly as I started to grope my crotch with my left hand, feeling my cock growing by the second as my head filled with the filthiest thoughts imaginable.

"Yes Mr. Farthing," Penny said quietly, and I could hear the humiliation in her voice. That turned me on most of all.

"Well don't keep me in suspense, my dear. Come on and get that robe off and let's see," I chuckled and with my free hand, the one not groping my now hard cock in my pants, I pulled my tie off and dropped it on the floor before unbuttoning the top few buttons of the shirt under my flabby double chin.

Penny hesitated for a moment, internally wishing she wasn't in this position no doubt, but she knew there was only one other option. She either endured my monthly visits or she and her precious daughter became homeless, and as she had each of the other times I'd been in this bedroom, Penny made the right choice.

I watched eagerly as she untied the belt and shrugged the robe off her shoulders, pulling her arms out of the sleeves and letting the garment drop to the floor around her bare feet and exposing herself to my scrutiny, and I whistled admiringly as I took in her body, clad in a skimpy and very revealing black teddy and garter set. Penny had certainly not disappointed in her choice.

She stood only five-feet-four but she packed plenty into her small frame. Her breasts were plump and rounded, they weren't pert any more given her age and having a daughter, but they were full mounds of flesh topped with big dark areola and nipples that got hard at the slightest stimulation. Weekly gym visits had helped her maintain her body to a degree, and whilst she was never going to win a bikini contest she had a nice hourglass figure that I liked.

I'd seen that body naked multiple times, and knew just how good it felt to caress her plump arse cheeks and squeeze those big breasts whilst she rode my cock. Today though, Penny's curves were being enhanced by exquisitely sexy lingerie that were driving me mad with desire. I especially found her stockings and garter belt exciting now I could see them, although there was a lot to be said for the French cut knickers that covered her crotch too.

I've always been aroused by women in lingerie. There is just something about seeing the female form hidden like that which both fascinated and intrigued me. Even when I was a young man in my late teens I would beg my acquaintances to dress up for me, even offering to buy them the garments out of my own pocket, and that was back in the dark days of the 1970s when money wasn't so freely available. See, I've always been generous!

Penny kept her eyes on the floor, and I could see how uncomfortable she was to have my eyes roaming over her lingerie covered body. She kept fidgeting a little, having to control her urge to cover her chest and crotch with her hands and arms as I admired her pale flesh where it contrasted against the black of her garments.

"Very nice, my dear. You have excellent taste in underwear, as well as men," I praised her with a grin, my lips curling up at the edges as I saw a shudder pass through her body at my words.

Penny didn't say anything in response. I hadn't expected her to either, and actively enjoyed her silence. I didn't need her to talk, just perform what was expected of her, and the quieter she was the more it gave me license to make her feel filthy.

"It takes a special kind of woman to wear stockings and suspenders, not everyone can pull them off," I said sweetly as I looked at the mature woman's legs clad in sheer black silk. They were a little thick, but nicely shaped still.

Again Penny was silent, but I couldn't fail to see her cheeks flush red at my compliments. She may find me a somewhat repulsive, dirty old man, but like all women she couldn't help feeling flattered and grateful for warm words about her body.

"Speaking of pulling something off..."

I left the suggestion hanging and grinned like a wolf at my tenant as I simply unzipped my pants and leaned backwards, placing my hands on the mattress either side of my ample girth as I waited expectantly.

Penny's head came up, her eyes meeting mine for a split second, before they fell to the bulge in my crotch and the open zip. She shuddered a little and I felt myself throb as she pursed her lips and swallowed, but, without any more prompting from me, crossed the space between us and dropped to her knees.

By now she knew the drill well. The first few times, in the weeks after we'd come to our debt repayment settlement, she'd been more hesitant, needing to be cajoled and reminded of her situation. But the last couple of visits, well things had changed subtly. Gone was the arguing and holding back, and in its place was acceptance and, more surprising to me, she had even started to moan more and buck her hips occasionally when I was inside her.

Sure Penny still despised me, and resented what services she had to perform to remain living in my property, but she had since rationalized internally that if she was going to degrade herself, she could at least enjoy the pleasure that getting fucked brought. She could always just hate herself for it afterwards, I guess.

I let out a deep chesty grumble of delight as I felt her hands pull my trousers down with a hefty pull to get them from under my flabby backside, before she rested her palms on my thighs and slid them up towards my crotch. The left held steady in place about three quarters of the way, but the right continued until it touched my bulge through my underwear and caressed softly, just the way I liked.

"Oh yes, that feels good," I groaned as Penny's warm hand gave my hard cock a quick squeeze, before it began to rub up and down again. Due to my belly being so ample, I couldn't actually watch whenever Penny - or indeed my wife - played with me. It was simply too big to see over, so I leaned back more, listening to the springs of the mattress protest vigorously and sag beneath me, and merely closed my eyes to focus on enjoying the feeling of her touch.

It was exquisite. With the palm of her hand she caressed my length, base to tip and back, through the fabric of my white Y-fronts, her pace slow and deliberate. Every two strokes, she'd close her fingers around my shaft and hold me, and when she did that I let out a deep moan of approval, confirming for Penny her actions were what I wanted.

"Oh! You are feeling frisky today, my dear!" I exclaimed with a grin when I suddenly felt her hand slide into my underwear through the opening on the front and her fingers caress my bare shaft.

I couldn't see Penny, but I heard her whimper from between my thick thighs, and without a single word from me she wrapped her hand around my cock and jerked me a few times, skin on skin, before extracting me via the way she'd entered my Y-fronts.

I heaved a huge sigh as my cock was released and throbbed in the warm air of the bedroom. Penny's hand was still around the lower half of my shaft and I listened as she breathed in the manly scent of my balls deeply, and let out a just audible moan as she took in the musky odor.

Her hot breath bathed my sensitive skin and I knew she must have moved her face closer to my crotch, no doubt to take in more of the smell more easily. I got a huge thrill from that. When I'd first starting fucking Penny several months ago, she hadn't hardly moved and definitely hadn't made a sound, now though she was openly stroking my cock without prompting, and eagerly taking in lungful after lungful of my sweaty balls.

"Don't be a tease and make me wait too long," I scolded mockingly as I pushed myself up as best I could again, my belly moving forwards until I felt it touch the top of Penny's blonde head.

Again I heard a moan from below, and felt hot breath bathing my balls and shaft, causing it to respond with a jerk in Penny's hand, which tightened its grip a little before it relaxed again and started to slide up my length.

"That's a good girl," I said approvingly as I felt her soft touch move along my six inches until her palm found the tip. Penny paused there for a moment and her fingers deftly played with my foreskin, rubbing it gently before she took a hold of me just below the bulbous head and eased her hand down, peeling back the covering and exposing the purple mushroom below.

Again I heard Penny take in a deep breath of my musk, and then without any warning I experienced the indescribable feeling of her lips closing around my exposed head of my thick, old cock. Fireworks exploded in my brain at the warm, wet softness that had enveloped me. I groaned loudly, and not for the first time wished I could see over my belly to watch as this very attractive woman sucked me.

"Your mouth was made for this, my dear!" I exclaimed as I felt her lips slide an inch down my shaft, and her tongue move over the head. The slightly rough sensation of her taste buds rubbing against my ultra sensitive slit, sending a jolt of pleasure coursing up my spine.

I was in heaven. There truly is nothing like a beautiful woman's month worshipping your cock, and I closed my eyes to focus entirely on the sensations as the soft lips around my shaft continued their downward trajectory until I found Penny's throat. She paused for the briefest moment and then pulled her head back, almost gagging as she did, from the invasion.

After a quick moment to settle herself, Penny started to suck me again, this time holding the base with her hand and bobbing her head quickly, taking only the first two inches into her mouth, but slurping noisily as she worked eagerly to please me.

I could feel her saliva on my skin. The warm wetness was so good it made me groan, especially when Penny took a deep breath and sank her mouth down my length again until her nose touched the cotton covered pouch of fat that sat above my cock after a good ten or twenty seconds of her excellent sucking. That represented the limits of how much I offered, and my little fuck toy was taking all of it right then.

This time, instead of allowing Penny to pull back when she gagged, I moved my hand quickly and placed it on the back of her head, holding her in place as I savoured the sense of power it gave me when she suddenly realised she couldn't breathe again easily, and started to choke on my cock.

"Oh yes! Oh, that feels good!" I said loudly as I felt Penny struggle. She was desperately trying to pull her head back, and I felt her gagging around my shaft, the sounds just loud enough to be audible to my poorly working old ears.

After a few seconds more of enjoying the power I wielded, I relented and removed my hand. Penny instantly pulled her mouth off of me and coughed, kneeling back away from me and looking up over my belly with hate filled eyes at my face. Tears were streaming down her red cheeks, and I could see saliva covering her chin. She looked so adorably filthy as she took ragged breaths.

I grinned at her. I was having the time of my life, just as I always did on my visits to collect the rent, and things were only just beginning.

"Something wrong, my dear?" I enquired with a raised eyebrow and a knowing smile.

Penny wiped her chin with the back of her right hand, the swell of her breasts heaving under the gorgeous black teddy she was wearing as she took in much needed air. Her eyes were blazing, but there was a little bit of something else there too, and seeing that turned me on. It was the contrast that I enjoyed most, hate and lust are only a sliver apart.