This is how I ended up losing money and dignity, but it was my fault for being so weak! As usual, I went to every flat in the building I managed in the cheap end of town to collect the rent on the first Friday of the month. All went as it always did until I got the last flat on the list, the one rented by Dean and Ruby.

I knocked on the door, and it took a while before Lily opened up. She was just tying off a dressing gown and stared at me as I stood there. “What do you want now, Tony? We don’t have loud music on, so can’t turn it down!”

Dean always paid the rent, so I asked if he was in.

“No! The fucker is out to earn some cash as he blew £200 at the bookies!”

Ruby was quite scary to me. She is a curvy woman with lots of tattoos and very loud, the type of girl who would have been a school bully and likely into S&M, I reckoned.

“Well… the rent is due … £450 … Today….” I stammered.

She looked at me blankly for a moment, looked me up and down, and then wandered off, leaving the door ajar. I heard her open drawers and fumble about, then she shouted, “Hang on, Tony, I’m looking for it.”

Ruby came back to the door with a tatty envelope in her hand, which she passed to me with an apologetic tone stating it was a bit short. I counted it out in front of her, and it was £200 short. I asked her if she was going to pay it today, and she asked for a moment to see if she had it elsewhere. Then, again, she wandered off, and I heard her shifting things about but returns empty-handed, inviting me in to wait while she looked, so I stepped into their untidy flat, and Ruby pushed the door shut behind me.

“Soooooo…” Ruby started. “I’m a bit short as my dickhead boyfriend spent it at the bookies!”

I said this was now 5 weeks in a row that they were short, and I was going to have to kick them out if they cannot get back on track. Ruby was looking at me and fiddling with her belt, her dressing gown becoming loose, and her tattoo-covered skin coming slowly into view.

“Is there any way you’d give me a discount this month or let me off this month?”

It was said with a husk and tone that put a sexual twist into the encounter. I stuttered and stammered as Ruby opened the gown to reveal her naked but for a pair of sexy panties, such perky tits pointing right at me, the shiny metal of the piercings catching in the light, twinkling and catching my gaze. I couldn’t help but look as she stood there in front of me with a huge grin on her face, one hand moving to caress her tit as she opened the other side to reveal her other pierced nipple, and the gown fell to the floor as if in slow motion.

“I was actually feeling a little horny and was about to play with myself, Tony. So why not watch a little? Think of it like a show you’d pay to see but that you’ve already paid for!”

As Ruby said it, she moved towards the sofa and knelt on the edge so that her rear was pointing at me, and she looked over her shoulder at me.

“You can leave if you feel uncomfortable, Tony,” Ruby offered, but I was cemented in place as this younger woman in front of me had my full attention.

Ruby turned and got comfortable, then pulled off her underwear to reveal a totally shaved mound, the pink of her pussy glimpsing in and out of view as her legs went wide, closed, and opened again. Ruby shuffled forward and started to use both her hands to spread her pussy wide, dipping her fingers in and finding her natural lubricant, which she spread across her clit. She really exposed her pussy to me as her legs went back and over, and she spread the lips wide open, her deep scary eyes looking at me as I looked on, taking brief glimpses into her eyes and then longer ones at her gaping pussy.

I took a step closer, almost involuntarily; I guess the caveman part of my brain hankering for a better look as Ruby continued to play with herself. She was definitely playing to the audience, I felt; she wanted me to see her every crevice and not hide any part of her body from me. It was like watching porn, only live!

“You’re very quiet, Tony. That Irish twang of yours seems to be lost….”

I looked on as she reached for her panties, and I thought the show might be over as I reached into my trousers to realign my erection, which had grown a little uncomfortable over the last few minutes.

The show most definitely was not over as Ruby begun to stuff the garment into her pussy. She pushed it in and spread wide as she did it until just a tiny piece of the black fabric was poking out from her sex. Ruby left it there as she again rubbed at her clit with renewed vigor, her fingers almost a blur as she did it but after a minute or two she slowed right down, her other hand reaching for the tuft of hidden panties which she slowly pulled out of herself. Once out she threw them in my direction, and my gaze followed them as they landed at my feet, and I noticed both of our eyes ended and the front of my trousers where a tenting was visible.

“You can jerk it if you want, Tony, I don’t mind….”

I was thinking about it but just too embarrassed to do it. What if Ruby laughed at the size of my dick and told everybody else in the building, or what if I shot my load after just a few seconds? I’d be mortified! Seeing I wasn’t going for this, Ruby stood and walked over to a set of drawers where she pulled out a huge realistic dildo. She flopped back where she was before and used one hand to stuff her pussy full of it, using the other hand to rub frantically at her clit again. I watched her doing this as if it wasn’t me in the room, but like earlier, and I was watching porn in my own flat.

Ruby seemed to be really getting herself off, and soon she cried out an orgasm, a squirt of liquid shooting into the air, and I flinched as it caught me off guard. This girl was clearly a bit of a dirty slut and had no problems showing off to a relative stranger! She took a moment to calm herself as the dildo slowly slid out the final inch, but she didn’t move from her totally exposed position.

“Wow…” I ended up saying to break the silence.

“Wow, indeed, my Irish friend,” she replied as she got up and put her robe back on, but not bothering to tie it closed.

I must have looked a bit dumbfounded as she walked past me to the nearby table and picked up her phone, noticing it was weirdly resting on its side. She fumbled with it for a bit, then smiled and tied up her robe, hiding her tattoos and piercings behind it.

“OK, Tony, I have to admit to being a bit of a bitch here…” Ruby suddenly sounded different, like she was in a courtroom-passing sentence. “I took the liberty of videoing on my phone what just happened, and it looks to me like you, the money-grabbing landlord, has taken advantage of little old Ruby. You’ve made her do dirty sexy things instead of rent.”

I protested more than I’d protested anything as she looked at me with a shit-eating grin across her face.

I think, Tony, if the other residents saw this, they might think differently, don’t you?”

I told her she was to blame and that it was tantamount to blackmail! She said it most definitely was blackmail, but there was a way out of it.

Ruby explained that she wasn’t going to ruin my life. That wasn’t her style. She just wanted me to let her off the £200 rent and get her own back on seeing her naked, exposed, and MORE. I was silent a bit too long as I computed it in my mind, and she shouted at me to decide. I asked what she meant by ‘get her own back,’ and I almost wished I hadn’t. She told me I was to strip naked and get myself off while she watched and gave instruction.

“What do you mean … Instruction?” I asked.

She told me I was going to obey her every command until I had shot my cum for her! She even had the nerve to tell me I’d likely enjoy it and be back for more another time! I must have looked like the rabbit in the headlights as she came right up to me and looked up into my face as I looked down at her.

“STRIP…” she yelled.

I didn’t move at first, but she commanded again, and I went into autopilot as the younger woman took control of me, and I didn’t feel I had any choice but to do as she commanded.

“This is all for the revenge, Tony. I’ve no desire to fuck an old balding, overweight guy like you, but watching you squirm like this is going to be great.”

She berated me more as I stripped down to my underpants and stood there meekly looking around the room, but not sure what I might see that might save me.

“Lose those too, Tony, and I didn’t keep my knickers on, so you cannot have yours.”

I was almost scared of her now, and she could see I was hesitant, so she just tugged them off me herself, my hands covering my semi-hard five inches as the underwear snagged at my knees.

“Tony, this is gonna get real bad for you if you don’t stop being a pussy and do as you’re fucking told!”

She pulled at my hands, and I didn’t resist as my penis came into view. Ruby laughed at me and wiggled her little finger in my face.

“That it?”

She laughed.

“You’re gonna have to work a lot harder now to please me, Tony, with that little thing.”

I looked down, and I was getting harder again, back to full erection.

“Wait there…” she demanded. I waited, and she came back with oil and a black piece of rubber. “Put this on,” she said and handed me a thick rubber ring thing with two holes, one bigger and oval, one smaller and round.

Seeing I had not a clue, Ruby told me it was a cock ring and explained how to put it on, offering to do it for me. I decided to try myself, smothered my cock and balls in the baby oil, and squeezed my balls into the larger hole. Once done, the rubber device made my balls swell while adding pressure to the base of my cock. It actually felt quite nice, and Ruby took a moment to peer down at it, so close I could feel her breath on my shaft. Then, Ruby stood and pushed me to the sofa until I fell into it. She told me to move myself down and open my legs so she can see it all, to which I obeyed, still on autopilot.

“Okay, Peewee, let’s see you jerking that thing.”

I was now 100% in her control and started to stroke my oily shaft for her. She looked on with a big smile as I stroked myself, naked but for my glasses and baseball cap. She gave me a range of instructions, changing hands, spitting in my hand to add a wet sheen to the oil. It went on like this for a couple of minutes, and I was getting close, so I made Ruby aware.

“STOP!”

I instinctively stopped as ordered, and Ruby ordered me to swivel on the sofa. I was confused, so she grabbed at my ankle and swung me around. I was put into a position doubled over with my legs in the air and my head hanging off the sofa where my backside had been a minute before.

“Do you know what happens next, Tony?”

I shook my head, she moved my hand back to my hard dick, and I felt my balls swollen and ready to pop.

“You’re getting a face full of your own cum, matey!”

I looked Ruby in the eye, and she saw my fear.

“Don’t panic, you sad little fucker. You’re getting to eat your own cum so accept your fate.”

I was still stroking, and as I turned my head, I realized that my cock head, in this position, was pointing at my face. I began to panic a little and slowed down my strokes to an almost standstill.

“Don’t you fucking stop, Tony. You’re getting a face-full, and I’m going to count you down from ten. So here’s a present to keep you hard.”

As she said it, she opened her robe and straddled my face, her pussy inches away from my eyes. I felt my cock jerk with the visual stimulation, and she must have noticed calling out “TEN….”

She moved away and covered up, kneeling next to me, and I heard, “NINE….”

I didn’t know if I’d make it to one at this rate, so I slowed a bit but still kept my stroking constant.

I kept it up, and when she goes to, “THREE….”

I knew I could match pace with her. I was peeking into her gaping gown at those pierced nipples, and so she roughly turned my head to catch the impending explosion from my balls.

“TWO…”

She pulled me over hard, so my cockhead was even closer, and I exploded. Cum was already shooting out as she squealed, “ONE….”

My eyes closed, and my mouth opened in an involuntary groan as I came. My balls, swollen by the cock-ring had me squirting under a pressure I’d never before experienced. A fast-shooting glob of cum hit me on my cheek, quickly followed by another that hit my nose and slipped into my mouth, which I swallowed involuntarily. More was shooting out of me than I expected, and it flew with such force, glob after warm glob splashing me in my face and neck.

“Don’t stop now,” Ruby bellowed. “Keep milking every last drop of your cum for me, Tony.”

I was slowing as the post-orgasmic pain was starting to hit me, but Ruby wasn’t letting me off, and she put one hand over mine to make me keep on stroking. I again opened my mouth wide in pain, and I watched but didn’t resist as she scooped up cum from my face with her free hand and deposited it on my lips. She let me suck her fingers in between my groans as the pain was becoming worse, and I began to resist her actions. Clearly, now every drop was gone.

Ruby let me stop, and I was getting a head rush from my orgasm and my position on her sofa. She used her phone to snap a couple of pictures of me as I lay there exhausted, too spent to fight her doing it. She stood up again and started to laugh as I clumsily fell from the sofa to the floor in a haze of not knowing what to do next. My engorged cock and balls encased in the rubber cock ring were now sore, and I asked Ruby if it needed to come right off now. Again, she laughed and said she’d check for me. I sat on the edge of the chair and opened my legs, the sensation of my cum sliding down my face and neck onto my chest quite odd, the salty aftertaste a new sensation I was still deciding on. Ruby got down close and roughly yanked the cock-ring off, pulling and squeezing my balls which made me groan in moderate pain, but that was strangely satisfying once they were free from the device.

“Okay, Tony, you can fuck off now. Consider that and the full envelope payment. Perhaps the same again next month?”

I was helped up, and she practically threw me out of the flat naked, my clothes following right behind me. The door slammed, and it was over. What will happen next month was now my only thought as I dressed, wiping my remaining cum on the hem of my T-Shirt.

The End.