Renter's Insurance
Chapter 1

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Reluctant, Coercion, Blackmail, Humiliation, Anal Sex, Exhibitionism, Voyeurism, BBW,

Desc: Sex Story: Chapter 1 - A young tenant behind on his rent tries an alternative method to get caught up with his landlady

It had started out innocently enough I suppose. I was living on the ground floor of a 1960's vintage apartment house near the downtown area while I was finishing the last few semesters of college. I was working my way through, so money was naturally tight but the resident manger, Bonnie, had been lenient on more than one occasion and things always seemed to work themselves out in the end. I wasn't sure about this time though, I was a good six week behind, and there weren't a lot of prospects for incoming cash.

I sat on my garden level deck about 11:00 A.M. contemplating these things sipping a beer and watching some of the buildings residents splash around in the pool.

It was the Labor Day weekend and Bonnie was busy preparing for her "End of Summer" building pool party. She had thrown a party like this at the beginning of the summer and it had been a great success giving many of the residents a chance to get to know each other. The buildings population was as diverse as the neighborhood we lived in. They were mostly older and single with a smattering of couples. The gay couple on the third floor and Nina, the single women in her mid-thirties who lived above me were the closest to my age, so until that previous party my socialization with most of them had been limited to passing remarks by the mailboxes. I had spent the bulk of that party trying to get close to Nina, not because she was all that attractive, but I had learned through some alcohol induced conversation that she had suffered from a gum disease in her early twenties which had required the extraction of all her teeth. The prospect intrigued me and while I had woken up in her apartment the next morning, my fully clothed status and splitting headache confirmed the fact that nothing had happened.

Bonnie emerged from her apartment struggling with a small table, and eager to ingratiate myself with her, I scrambled over the railing and grabbed one end of it.

"Oh, Thank You, Sweetie." She said as we began placing chips and assorted snacks on the table.

"Sure thing Bon. It looks like it's going to be a nice day for it."

"Yes it does. I hope more people show up, it was so much fun last time."

"It really was. I'm looking forward to it."

She made her way back to her apartment, and I hopped back over the rail to mine. I wanted to get a couple of more beers down before I had to socialize with all her old maid friends.

Bonnie got her wish, and by 12:30 there was probably 30 people in the pool or around it and all seemed to be laughing and having a good time. I was feeling pretty mellow and floating around the pool on an inflatable raft.

Bonnie and the core of her friends were in sitting and standing near the edge of the pool talking among themselves, and I was sure that I was the topic of discussion more than once. Bonnie was standing next to the table, her thick legs still amazingly white this late in the summer. She was wearing a summer top that was more appropriate for one of the co-eds at school than a 65 year-old apartment manager and her fat rolls were blatantly obvious through it as they were pushed out at the top of her severely out-dated terry cloth shorts. Now and then the top would ride up exposing her flabby midriff, but she continued to laugh and chat while pulling it back down with one hand.

Now and then I would glance over and they would all be looking in my direction as they talked. While I really didn't appreciate the fact, I was sure that Bonnie, an uncontrollable gossip was sharing my arrearages problem with them. In any case, I certainly wasn't in a position to confront her about it, so I busied myself with Nina hoping to make further inroads towards a gum-job.

The alcohol flowed freely and the sun was warm and the alcohol flowed freely, so by 3:30 or so when the afternoon thunderstorms rolled in, many people had already had their fill and made their exit. When the first few raindrops began to fall, the party was officially over, and after a few cursory attempts at cleaning up, most of the items were undercover in the building entry way and all had made their escapes. While the pool area was free of clutter, I realized the Bonnie was still left with a monumental cleaning task eager to solidify my standing I began helping her out, carrying things into her apartment, loading the dishwasher and, so forth.

"Thank you Sweetie," she said somewhat drunkenly, "but you don't have to. I can get the rest of this."

"I wouldn't dream of it Bon. You've been so nice to me, it's the least I can do."

Her protests were short-lived, and after another 45 minutes or so of cleaning, and a couple of more glasses of wine on her part, she had clearly had enough.

"Bonnie," I said leading her to a chair in the dining room, "Just sit down and let me finish this up."

There was no protest this time as the sun and alcohol had taken their toll on her so she sat in the chair and attempted conversation as I finished up.

After a while, her tone became more serious, and I knew what subject was coming.

"Honey, you've really got to come up the rent, Jerry's really mad and he's talking about eviction."

"I know Bonnie" I said in as meager a tone as I could muster "I have some cash coming in at the end of the week. Do you think you can hold him off that long?"

"Well... I think so, but you've really got to get caught up."

"I know Bonnie, and I will." I said putting down a dish rag and walking over toward her "and I really can't thank you enough for helping me out."

I didn't know how this was going to play, but I was eager to change the subject so I moved behind her with the intent of rubbing her shoulder.

"You really wore yourself out Bon, here, let me work out some of those kinks." But when I placed my hands on her shoulders, she winced in pain and heat radiating from her skin told me why.

"Wow, I'm sorry Bon, you really got cooked. Do you have anything to put on it?"

"Oh don't worry about it Sweetie, I've got some lotion that I will put on before I go to bed."

"It's no problem." I said walking to her bathroom for the lotion and not waiting for a protest.

"You really don't have to." She said without conviction "You've probably got a lot of other things to do on a Saturday evening besides rub lotion on a fat old sunburned lady. Besides, I think I'll just go to bed anyway, it's been a long day."

"Don't be silly Bonnie," I said warming some lotion in my hands "this will only take few minutes, then we can get you to bed."

I began rubbing the lotion into her back and she closed her eyes and even moaned a little.

"Oh, that does feel good. I never would have been able to reach back there."

I continued with the lotion on all the exposed skin, even gently rolling the spaghetti straps of her top down her shoulders. She sank lower and lower in the chair as I covered her arms, neck and even her chest as far down as her top would allow. Surprisingly, I wasn't repulsed as I gently kneaded her soft flesh. To the contrary, I actually started to become aroused wondering what it would be like to knead those huge flabby melons of hers.

She was now on the edge of consciousness, still moaning softly at my touch when I gently grabbed her elbow saying "Come on now, let's get you to bed."

There were no protests, and she staggered slightly as I led her towards her bedroom. I pulled all the covers down and she flopped on the bed on her stomach. I was going to cover her with just a sheet and make my exit, but as I stood with the sheet in my hands, I stared at her huge, flabby ass, and something got the better of me. I laid the sheet back down at the foot of the bed then retrieved the lotion from the dining room. She was almost asleep now, and I hoped my next move would have the right effect. I warmed some more lotion, then gently began rubbing it into the backs of her thighs.

The moans came a little louder and more pronounced. As I continued to work the lotion into her legs, my hands moved higher and higher on her thighs with my thumbs working the insides and creeping ever closer towards her pussy. As my hands moved higher, I noticed that her moans were becoming more intense, and for the first time I realized that they were more from her arousal than from the relief of her sunburn. With this in mind I became bolder and my fingers began to creep under the leg-bands of her terry cloth shorts while my thumbs worked ever closer towards my ultimate goal. Still not knowing if Bonnie was asleep or just feigning it, I decided it was time to go for broke, after all, what was the worst thing that she could do to me, evict me?

With my finger up under the leg-bands of her shorts, I worked my thumbs into the moist, sweaty gap between her thighs. They brushed her pussy lips which elicited the loudest moans yet, and I knew I was home-free, she wanted this as much as I did, may be more. With out further prelude, I pushed my thumbs into her aged cunt and to my surprise, found it quite wet and inviting.

Working them in and out, the moans became even louder and steadier, and soon she began pushing back with her hips. When her ass was raising almost completely off the bed, I suddenly gripped her waistband with my fingers and began pulling them down. Her hips raised in cooperation and in seconds I had slipped them over her feet exposing her huge, fleshy ass.

I began kissing the inside of her thighs and started licking my way higher.

Her legs spread farther to accommodate me and some grunts began to accompany the moans. I grazed her now exposed pussy lips with my tongue, and she bucked back against my face. My nostrils full of her heady scent, I grabbed her flabby hips and jammed my tongue in her cunt as far as it would go.

"Oohhhh, yess" she moaned bucking back against my face.

I couldn't begin to imagine how long it had been since she had been serviced this way, but I wanted to be sure not to disappoint her regardless. I sucked her fat clit between my lips and assaulted it with my tongue. Alternating with a few quick jabs into her pussy, she soon began to shake and in minutes, her thick thighs squeezed against my head as convulsions shook through her.

I relaxed my assault, and when the trembling had subsided, raised myself on one elbow and deftly removed my shorts with the other hand freeing my throbbing cock. I slid up onto her back, and guided my cock towards her pussy. When she felt it against her cunt-lips, she pushed back against me and I felt myself slide into her warm, wet tunnel.


I kept a slow steady pace at first but her reactions came faster and faster.

I grabbed her flabby hips and pulled her to her knees, her cunt gripping me surprisingly hard. I jammed into her faster and faster sending shock waves rippling across her fleshy ass. I felt her tense and her cunt gripped me even harder as her second orgasm racked her body. It was more than I could take, and I slammed hard into her as I jettisoned a magnificent load of cum into her wizened old cunt.

I collapsed onto her back, then rolled off to one side with my dick falling out with a slurping sound. The alcohol and sun now took it's toll on me, and I remembered seeing a shimmer of sweat glistening on her back just before I drifted off.

I awoke to the sensation of a hand gently stroking my cock to hardness. As I came to full consciousness, Bonnie realized that I was awake and smiled at me while continuing. I had no Idea how long I had been asleep, but I could tell it was completely dark outside. The rest had obviously done wonders for her as she couldn't wait for another round.

"That was so gooooood." She said emphatically "It felt like the first time"

An evil thought came to mind.

"Do you REALLY want it to feel like the first time?"

A quizzical look came over her face, and I didn't give her time to think about it. I rolled her over on her stomach again and straddling her legs, reached for the lotion. Lubing my cock generously, I began to work it up and down the crack of her ass.

"Ohh No" she began to protest as she realized where this was going "I couldn't... I mean I've never"

"Shhhh." I whispered, "Trust me. You'll love this."

I pushed my cockhead against her asshole, and the head slipped in. Slowly, I pushed farther up her poop chute saying "Tell me if it hurts."

"Oh... Ohhhh, OOOH... Wait."

I stopped momentarily and let her get accustomed to my size, then pushed a little farther. Soon I was buried to the hilt, and I waited. When I felt her relax, I began to stroke slowly at first, then a little faster, and a little faster yet.

"Ohh yes. OOOOHHH Yesss. DAMN I never though this could feel so good, YESSSS."

Now I was slamming into her and her asshole was gripping me tighter and tighter. Her flabby ass jiggled with the shock. I grabbed her by the hips and pulled her up on her knees. I pushed her top up from the bottom and she struggled to pull it over her head freeing her saggy milk-bags which dangled and swayed with every stroke.

I had never really considered myself any kind of a stud, but I was pretty proud of the women I had coaxed into my bed. They were all young and trim with firm tits, but as Bonnie's ass gripped my cock, and I reached around and squeezed one of those, huge, flabby mammaries, I had the distinct feeling that there was an entirely different world of sex out there that I had been turning a blind eye to.

As she squeezed her huge ass cheeks together and raised to meet my thrusts, I felt cum boiling up in my balls. She shuddered and convulsed again, and I slammed into her spraying my cum up her ass.

This time as I lay recovering, she dragged her nails across my chest lightly.

"Consider your back rent paid." She said. "do you want to pay this months?"

"Bonnie, I don't think I can..."

"Oh, No, Silly. I've had more than enough... for now, but mine isn't the only head you've turned around here. No, if you want to pay the rent, all you have to do is answer your phone."

"I don't think I understand."

"You will," she said, "You will."

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