Cougar Condo 2

~~~ Chapter Notes ~~~

This piece is part of a series. The story will make more sense if you read it from start to finish.

All of the chapters in this series have been completed. They are submitted to Literotica as a bundle. They should appear at a rate of one per day.

~~~ Day 4 - continued ~~~

Once we had recovered, Helen asked me to help her get Hannah into the tub. I rolled to the edge of the bed and easily picked her up. I carried her into the master bathroom to find a specially-made Jacuzzi tub. There were two bench seats. I sat on one, holding Hannah. Helen took the other one. She closed the little door and started filling the tub.

I joked with the two sisters that I was going to have to get a tub like this in my room. We got a little naughty while we were bathing but we mostly behaved ourselves. I caught sight of a clock on the wall and realized that I was needing to keep things moving. Helen saw where I was looking and nodded.

We all got cleaned up and then I helped Hannah get dried off. She groped my cock, giving me a wicked grin. She tried to pull the towel away as I dried myself. I gave her a kiss and told her to behave. She snorted at me.

I got her into her chair - which Helen had brought from the front room - and wheeled her back out of the bathroom. I gave my two lusty lovers another hug and kiss and headed for my mother's apartment.

~~~

"How did it go?" she asked.

"Good, I think," I told her, giving her a hug and a kiss on the cheek.

"You think?" she asked, with a smirk.

"They both got a pussy full of Cream of Mark," I told her.

She raised her eyebrows at me - and then shook her head, smirking, and went back to her meal preparations.

I sat down to spaghetti with homemade meatballs and that garlic bread that comes from a box but tastes oh so good!

I discovered that I was starving. The two sisters had really taken a lot out of me!

"If Helen schedules another session," I told mom, "try to get her to pick 10pm."

"I'll text her," mom said. "If you spent that whole four hours fooling around, I'm sure she'll want to schedule you again. She struggles a little, finding stuff for Hannah to do. It went okay?"

"Ask her," I said, smirking.

"Fine, I will!" she retorted, grinning.

She fired off the text as I finished my food and started cleaning up the dishes. A few minutes later, her phone pinged.

"Oh!" Mom gasped.

"What?" I asked, snickering.

"She said that she forgot to give you a donation," Mom replied.

"She doesn't have to ...," I began to say.

The doorbell rang.

"That's her, isn't it?" I asked.

Mom nodded - and shooed me out of the kitchen to answer it.

Out of the corner of my eye, I noticed that she was following me. Curiosity killed the cat ...

I opened the door to find Helen standing in the hall - with Hannah at her side.

"Can we step in for a moment?" Helen asked. "I'm worried about what Hannah will say in a public hallway."

She glanced up and saw mom.

"I'm not sure you'll want to hear either, Martha," she said.

Mom waved away her concerns.

I stepped into the hallway and let the two sisters enter, pulling the door behind us.

I knelt next to Hannah's chair.

"Hey, sexy," I purred.

She tried to hand me a wad of money.

"Nope," I said. "I don't want your money. I should pay you for fucking me so good."

Hannah cackled with laughter and looked up at my mother.

"He made my pussy so happy!" she gushed.

"I'm glad to hear it, Hannah," mom said, trying not to blush.

I stood and looked at Helen.

"I was just telling mom that - if you guys want to schedule another session - we should do 10pm," I said. "That way I can just spend the night."

"Spend the night in my pussy!" Hannah cheered.

I chuckled and leaned down to kiss her cheek. When I stood back up she shoved her head at my groin and tried to nibble my cock.

"Hannah ...," her sister warned.

"I want some more," she complained.

Mom snickered.

"I'm only rescheduling on the condition that you take Hannah's money," Helen informed me. "She was adamant."

I knelt down beside the wheelchair and Hannah shoved the money at me. I pulled the $20 bills apart. There were a bunch of them. I took one and handed the rest back to her.

"There," I said.

"No!" Hannah snarled. "You made my pussy happy!"

"It's fine, lover," I told her.

"Have you given anybody else's money back?" Helen asked me.

"Geneva," mom said.

Helen glanced over at my mom and then looked back at me.

"I'll give you that one," she said. "We, however, can afford to give you a little gift - and Hannah won't let me sleep tonight if you don't take it."

I knelt back down next to the woman with the pigtails. She scowled at me.

"If I take this," I told her, "then that just means I have to come spend the night sometime - and you're not allowed to give me any more money."

"I'll shove it in your ass!" she barked.

She cackled with laughter.

I leaned in, kissed her mouth, and took the money.

"No more money," I told her.

I stood back up.

She stuck out her tongue at me and then laughed. I pinched her tit and she laughed harder, lunging at the tented front of my pants.

I leaned down - put my mouth to her ear - and whispered, "Next time, I want a blowjob - and I'm gonna suck your pussy so hard you scream."

"Yes ...," she purred softly.

I took down the Mason jar, popped the money inside, and showed it to Hannah.

"Happy?" I asked.

She nodded and said, "Yes! A whole jar of happy pussies!"

Mom gave a snort of laughter.

I gave Helen a hug and a kiss - as her sister groped my crotch again.

I opened the door and the two of them slipped back out of my mother's apartment.

I turned back from closing the door to find my mother in front of me. Her arms went around me and her lips pressed against my cheek.

"That was so lewdly adorable," she snickered.

"We had a lot of fun ...," I told her.

"I kinda got that feeling ...," she giggled.

I slipped past her to go change my shirt and head to my next appointment.

~~~

At 6pm, Esperanza gave me a foot-job. She was actually pretty damned good at it. I'd had one or two before and they're not as easy to pull off as you might think. She was as enthusiastic as she was talented and I blew my load all over her lacy white ankle-socks.

At 8pm, Sophie and I fucked on the sofa and then ate homemade ice cream.

Kaia took me out for a 10pm jog and then - when we were both good and sweaty - we returned to her apartment and fucked in the shower.

I slept in Mom's bed and we talked about my day as she teased her fingers through my hair. I didn't dare tell her how hard my cock was. Messing with my hair is a big turn-on for me but Mom has done it since I was a kid. I don't think it's some kind of Oedipus thing - but it really gets me going. I faced away from her to make sure she wouldn't notice my stiff cock. I fell asleep in her arms.

~~~ Day 5 ~~~

Mom and I had breakfast together and then I moved furniture while she vacuumed.

At 10am, Zola had me meet her at the gym. I helped her with weights and things as she worked through her routine. She kept rubbing her ass up against my crotch. Her skin-tight leggings were looking fabulous and she leaned in and whispered that she wasn't wearing panties - which had me looking more closely at her tight little camel-toe.

She worked herself into a sweaty mess and then - when she told me to try the bench-press - the other residents suddenly disappeared. I pinned the weights, laid down on the bench, and brought my hands to the bar. Zola stepped across my body and straddled me. I heard cloth tear as she hooked her fingernails into the cloth of her leggings and tore a hole at the bottom. She fished my bulging prick out of the leg of my gym shorts and impaled herself on my shaft.

I glanced around the room and spotted two or three security cameras. My heart raced as she rode me - worried that we were about to be kicked out of the place. She fucked me faster and faster, and I gave up watching for a guard to appear and reached up to pinch the nipples that were poking through her thin sports-bra. She shuddered and then her pussy clamped down on me and I groaned as my balls exploded.

When she could move again, she slid my cum-slicked cock in and out of her pussy a while longer - relishing the feeling of our gooey mess turning to a foamy froth inside of her tight cunt. She leaned forward, pressing her tits into my palms, and kissed the fuck out of me.

She stood, quickly sucked me clean, and tucked me back into hiding. She stepped back and I could barely tell that there was a jagged hole torn in her pants - since the tear was pointed towards the floor.

She dragged me to her apartment where she sat me on a kitchen chair and rode me for the rest of our time together - getting herself two more orgasms.

~~~

I showered when I got back to Mom's. I smelled like sweaty sex. She giggled at me as I plopped into a kitchen chair with a sigh.

"Do I need to cancel the morning sessions?" she asked with a snicker.

"No ...," I moaned.

"Well, tomorrow's Sunday and you don't have any sessions until after lunch," she reported. "You going to chapel with me?"

I gaped at her.

"What?" she snickered.

"I feel like I've fucked half the women in this building ...," I said.

"Not even close ...," she replied, grinning.

"I'm not sure I can sit in church with them," I finished.

"Nobody will say anything," she assured me.

"We'll see ...," I said, noncommittally.

We finished eating our light lunch and then I headed for my next appointment.

Amirah (my 1 o'clock) wanted to be fucked missionary - and then we just lay there and chatted.

At 3pm, Khloe wanted to 69. As soon as I got her to cum, I rolled on top of her and plowed her until she got the creampie that she'd requested.

After dinner, Maya and I played handball and then I mashed her up against the wall of the court and fucked her from behind as she moaned.

Zaniyah told me that she didn't want sex - she just wanted to sleep in my arms. I texted Mom and told her that I wouldn't be home. She made me promise to be home before 10am so that I could go to services with her.

~~~ Day 6 (Sunday) ~~~

In the morning, Zaniyah and I slept in, fucked in the shower, and then ate breakfast in the diner. Afterwards, she gave me kisses, thanked me for a lovely night, and sent me home.

I changed my shirt, shoved Zaniyah's donation into the Mason jar, and waited for mom to finish getting ready.

The service didn't last too long. I felt like I knew half of the women in the little chapel but Mom assured me that my count was off. She DID admit, however, that - by the time the next week rolled around - the number of women in the room who'd had my cock between their thighs was probably going to break the 50% threshold. I shook my head at her as she snickered.

At 1pm, Morgan and I jogged down the street - to a park with trails. I leaned against a tree while she bounced up and down on my cock until she drained my balls. After that, we jogged back to the apartment building and showered together.

At 3pm, Emmaline laid herself spread-eagled on the kitchen table and I plowed her hard and fast. When she had recovered, we sat on the couch and cuddled - with my penis still safely wrapped inside of her cum-filled twat.

I got home, showered, and changed my shirt. Marianna had offered to take Mom and me to dinner before our "date".

She and Mom seemed to be pretty good friends and I was getting a little nervous, the longer they visited. Mom rolled her eyes as her friend snuggled against me and her hand disappeared under the table to tweak the head of my dick.

"Such a handsome boy, Martha," she told my mother.

"You're evil," Mom told her, grinning broadly.

"I wonder if he's as good of a kisser as you," the woman said.

I felt my eyes grow wide.

"She's fucking with you," Mom assured me, shaking her head.

"I tried to get you into my bed," Marianna told her.

My eyes shot to Mom's.

Mom laughed and said, "You were drunk. You don't even remember that night."

"You sure blushed when you told me later though," the woman replied.

I laughed as Mom's cheeks pinked.

"I'll pay double if I can have you both," the woman told her.

"No," Mom said quickly - and firmly.

"My loss," Marianna sighed.

She paid the check and we dropped Mom off at the 5

th

floor before heading to the penthouse.

Marianna pushed me onto her sofa, pulled my pants and boxers off, and settled between my thighs. She stroked my cock and began undressing.

"Your mother is a beautiful woman," she said quietly. "I wasn't as drunk as she thinks I was."

I moaned as she leaned forward and forced my cock between her tightly-clenched lips - forcing me to fuck my way into her mouth.

She pulled off of me and looked up.

"Grip my hair in your fist and fuck my throat," she ordered.

She took my hand and pressed it to her head - shoving my fingers into her thick, black wavy locks. She slid her face back onto my cock - more and more - until I was buried in her throat. She reached back and swatted my hand.

I moved too slowly and her teeth clamped against my shaft. I jumped and she pulled her teeth back. I pulled her hair - pulling her face off of my cock - and then slid her head down again - until her nose was once more buried in my pubes. She purred - so I did it again.

It felt good and I sped up a little. She purred more - catching a breath of air each time her throat was clear.

"Faster!" she gasped.

I went faster.

"Harder!" she ordered.

Soon, I was holding her head firmly by her hair and slamming her face onto my cock - ramming my prick down her throat like it was a pussy instead of an esophagus.

Marianna's face was glowing. I'd never seen a woman so happy to be face-fucked.

I suddenly realized that my orgasm had crept up on me. I buried my cock in her throat and groaned as my sperm began rocketing down her throat. I heard the gush of fluids hitting the carpet and looked down to see that she had squirted all over the floor. Her hands were on my knees. She wasn't even touching herself. She had cum just from me cumming down her throat!

She pulled off of me, climbed onto my lap, and slid my saliva-covered cock into her dripping cunt. She moaned and writhed as she rode me.

"Pull my nipples!" she ordered.

I pulled - and then pulled harder - and then harder - as her keening grew louder and louder.

She squirted again - this time all over me.

It was too much. I grabbed her hips and yanked her down onto my cock just as it began exploding inside of her.

I was exhausted.

I laid my head back - against the back of the couch. A pair of soft breasts pressed against my face - and arms wrapped around my head. I was in Heaven.

I thought the woman might keep me overnight but she kissed and cuddled for a bit longer and then sent me home.

I showered, changed into my bed clothes, and climbed into my mother's bed.

"She told you she wasn't that drunk, didn't she?" Mom asked.

"Yeah ...," I replied.

I started to tell her how it had gone but she covered my mouth with her hand and just pulled me against her. I relaxed in her arms and was soon asleep.

~~~ Day 7 ~~~

Elizabeth @ 10am - cowgirl.

Milan @ 1pm - doggy.

Paige @ 3pm - reverse cowgirl.

Rhianna @ 6pm - kitchen counter - followed by shower.

Grace @ 8pm - alley behind the apartment building - while a homeless whino watched us as he settled in beside the dumpster to spend the night.

As 10pm rolled around, I got a text from Mom.

"You're staying at Angelina's tonight," it said. "I'll see you at breakfast in the morning."

I arrived at the apartment and was met by a woman with an overnight bag in her hand. She ushered me inside where there was a woman who didn't look much older than me sitting on the couch. Her curly brown hair was bobbed off just above her shoulders.

"Mark," the woman said, "this is my daughter, Angel. Her father did not treat her like an Angel and now she has a poor self-image - which has allowed a selfish young man to steal several years from her. I've talked to some of the others from my building and I know that you know how to treat a woman. I'm staying at your mother's tonight. I would desperately love for you to show my little girl that she's a beautiful young woman who deserves to be treated well and that she shouldn't settle for some man who gets his jollies and then makes fun of her because she didn't get off."

"Mother ...," the young woman said.

"You're welcome to make love to her wherever the two of you want," she said. "Don't worry about making a mess. I just want you to make my little girl happy."

With that, she turned and left the apartment.

The door closed and I stood there, silently, for a second as the woman stared at the floor.

"Can I sit?" I asked.

"You don't have to stay," she said.

"I'm pretty sure she's sleeping in my bed tonight," I replied, with a grin.

She looked up, saw my expression, and snort-laughed.

"Want to go for a walk or something?" I asked.

"There's a little convenience store - a block over - that has CBD," she offered.

"I don't ... uh ... but I'll walk with you," I offered.

"Let me get my wallet," she said.

She went to the smaller bedroom and returned a moment later - pulling on a hoodie.

"You got a keycard?" I asked.

She spun on her heel and went back to the bedroom again, reemerging a second later.

"Thanks," she said. "That would've sucked."

Her smile was nice. I chuckled. She gave a little giggle.

I offered her my arm - which she took - but then we had to separate long enough to slip out of the door. I made sure it latched and then we headed for the elevator.

She took my arm again and I looked at her. She was short. The top of her head barely came to my chin. She was dangerously thin - like she hadn't been eating or something.

"I won't bite," I promised.

"What if I want you to?" she asked, with a smirk.

"I could probably be bribed," I said, smirking back.

She snort-laughed and then shook her head.

We rode the elevator down, walked to the front of the building, and headed outside. It was a lot darker than I had expected. The air was thick and hazy.

We walked to the end of the block without seeing anyone - but there were a few people wandering about as we got closer to the little all-night convenience store.

I was studying the people under the streetlight down by the corner and missed the guy behind the bush until he had stepped into our path. I froze in my tracks.

Angel squeaked and yanked her hand from the pocket on her hoodie. I heard a hiss and a burst of peppery spray caught me in the hairline as Angel tried to step back away from me.

"Fuck!" the guy yelled - at the same time that Angel yelled the same thing.

The would-be attacker stumbled back into the brush between the buildings as Angel stepped in front of me to face me.

"I'm so sorry!" she gasped. "My finger caught on my pocket as I pulled out the pepper spray. Are you alright?"

"I think I'm okay," I said. "It's not in my eyes. I just need to wait to see what's burning. I don't want to rub anything."

"Stay here!" she gasped.

She took off towards the store.

"Angel!" I called after her. "It's okay!"

In seconds, she came sprinting back out of the store - with an angry Indian fellow running along behind her. She had a bottle in her hand. She wrung the lid from the top as she approached.

"Lie down!" she ordered.

I lay down on the sidewalk.

"Hold your breath!"

She began pouring cold liquid across my face. The burning lessened almost immediately. I held my breath as long as I could and then shoved my hands at her - motioning for her to stop pouring. As soon as she did, I took a breath.