Rich Guy 1 - Cover

Rich Guy 1

Copyright© 2019 by Dark1

Chapter 9

Coming of Age Sex Story: Chapter 9 - Direct Sequel to the Rich Kid Series. Carter's life changes with his unexpected inheritance. Now in control of millions, he struggles to find himself and identify his own desires, while unraveling secrets of his father's past. His relationship with Candace takes several turns and meetings with her mother & sister Cassie will shake up all of their lives. Old relationships are re discovered and new ones are born while Carter explores the world.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Blackmail   Coercion   Drunk/Drugged   BiSexual   Cuckold   Sharing   Wife Watching   Sister   MaleDom   Humiliation   Rough   Group Sex   Harem   Orgy   Swinging   Anal Sex   Analingus   Double Penetration   Exhibitionism   Masturbation   Voyeurism  

We reached an equilibrium after a week of strangeness. In reality, it was just an expansion of what we had already been doing. Though, now, I didn’t give a shit about schedules. Candace would come home on her late day to find Cassie bouncing on top of my cock while we sat on the couch in the living room and Cassie found Candace on her knees in the kitchen several times, happily slobbering on my cock. I had to restrain myself from inviting Cassie to join. I had little doubt that she would be down for it, but I was pretty sure that Candace would not be.

What I wasn’t expecting, however, was the growing competition between the sisters. My suspicions about Candace’s jealously were slowly being solidified as her antics increased.

On an afternoon that I had finished working out without Lindsay’s presence, Candace walked into the gym’s shower, totally naked. Wordlessly, she dropped to her knees and began pleasuring my cock with her mouth. Cassie came into the gym, dressed in spandex for her workout. She saw Cassie sucking my cock, shrugged and then stepped onto the elliptical machine. I stared at Cassie’s tight ass as I faced fucked Candace to completion.

Later that week, I returned home from running some errands to find Cassie on my bed.

She was naked, save for a blindfold and some cuffs around her ankles and wrists. A metal bar was attached between her ankles, keeping her from closing her legs. She had managed to tie herself to the headboard of my bed. Beside her was a folded piece of paper.

I picked up the paper as I kicked off my clothes. It simply read

“Use me however you would like Sir.”

Cassie began to whimper in anticipation as I climbed onto the bed behind her. She sucked in a deep breath as I fitted my cock against her cunt.

“You’re a bad girl, huh?” I asked, teasing her pussy.

“Yes Sir.” She gasped.

I grabbed her hips and shoved my cock all the way into her with one push. I slipped in easily, seeing that she was already extremely wet. I humped her hard and fast as she shoved her ass back towards me, restricted by her bonds.

“Oh yes. Oh yes. Fuck me. Fuck me.” She moaned, arching her back in an attempt to get me in deeper. The spreader bar provided an interesting opportunity to me and I pulled my cock out of her slick cunt.

“You know, your ass is really amazing.” I commented, smacking it lightly.

“Thank you Sir.” She moaned, wiggling her ass happily.

“Good thing you’re not afraid of a cock in the ass.” I replied, fitting the head of my cock against her anal pucker.

“No Sir.” She gasped as I pushed in.

The bar kept her legs apart, spreading her ass cheeks open and allowing me to reach depths that I’d never been to before. She made noises that I’d never heard come from a woman before, which only increased when I blew an enormous load of cum straight into her colon.


Candace apparently took this as a challenge. While she was growing used to anal, it still wasn’t her favorite activity. However, she did know other ways to get into my good graces. On her ‘early’ day from school, I got a message from her.

“Hey, can you come down here?” She asked. It was funny that I’d get a text message from her. I was in my office and I knew she was in her bedroom.

I stood up and wandered downstairs towards her bedroom. As I turned into her doorway, I came to a stop.

Candace was lounging on her bed, completely naked. She had a huge grin on her face.

Kneeling on the floor in front of her, facing me, was Anna. She had on a tiny red thong and a red ribbon around her chest, tied in a bow between her small breasts.

“I brought you a present. I hope you like it.” Candace said seductively.

“Oh yeah? Where did you find it?” I replied, playing along.

“She was a stray on the side of the road. I couldn’t just leave her out in the wild. Can we keep her? Please?” Candace teased.

“I don’t know. Is she going to be a good girl?”

“Oh, she’s a VERY good girl.”

“Show me.”

“Come up here sweetie, show Carter what a good girl you are.” Candace called out, leaning back on the bed.

Anna stared at me for a moment and then turned around and crawled up onto the bed. As she lowered her head down to Candace’s crotch, her perky ass went up into the air. I admired it for a moment and then realized that there was something between her cheeks, barely covered by the string of her underwear.

I moved onto the bed behind her and pulled her panties out of her crack. As I had suspected, she had a butt plug inserted into her rectum.

“What’s this?” I asked, looking down at Candace, who was already squirming on the bed under Anna’s work.

“That’s another present for you, if you’d like it. She’s been practicing for you. She’s all lubed up and ready to go. No waiting.” Candace smiled.

“Is that so?” I asked, grabbing hold of the plug.

“Uh huh. Feel free.”

“You ready for this?” I asked.

Anna lifted her head up from Candace’s pussy and turned around towards me.

“I think so.” she replied nervously.

“Aww, isn’t she adorable. Be nice to her Carter. You might kill her with your big cock.” Candace giggled as I kicked my pants off.

“I’ll consider it.” I replied as I reached for the plug in Anna’s ass.


I had to get the two sisters together. I just had to. I knew that Cassie would go for it. With Candace’s growing jealously, I suspected that she would be willing to do to go along with it, if nothing but to not concede more of my favor to her younger sister. I just wasn’t sure how to get the stars to align to make that all happen.


The three of us were enjoying an increasingly rare weekend off together. Both sisters’ social lives were picking up steam and it was pretty common for one or the other to be out late on a Friday or Saturday, or occasionally not come home at all.

We were hanging out in the hot tub, as was usual. Candace’s breasts were floating on the top of the water and Cassie was reclining on the edge of the pool, showing off her tight body in a tiny white bikini. We’d rapidly finished one bottle of wine and were ready for another.

“I’ll grab it.” Cassie announced, sliding out of the water. I watched her perky ass bounce away down the hallway.

“She’s got a great butt.” Candace commented unexpectedly.

I turned towards her. She had a distant look on her face as our eyes met.

“Yeah she does, but so do you.”

“Her’s is really tight. I know how much she likes anal sex too. I’m trying to get used to it.” Candace replied, her voice slightly strained.

“I know you are. Trying is half the fun. Besides, you keep bringing hot little sluts home and I’ll be happy.”

I had sodomized Anna so hard the last week that she had difficulty walking out of the bedroom, much to my delight.

“Yeah? You sure?”

“I mean, any time you wanna offer up your ass for some practice, you just let me know.”

“Or, you could just take it.” She said seductively but with fear in her voice.

“That too.” I grinned.

“Hey guys.” Cassie called out, walking back out into the patio with a bottle of wine in hand.

“Heya.” I grinned.

“Hey, so, that door on the wall next to the wine cellar. Where does it go? I’ve never been in it.” Cassie asked inquisitively.

I paused for a moment, mentally visualizing the door and the area.

“You know, I have no idea.” I replied.

“Seriously? Don’t you live here?” Cassie giggled.

“Yeah, but I never had a key to get in it. Wait a minute, I do now!” I exclaimed.

“Yeah?” Cassie said, perking up.

“Yeah. Come on, let’s go on an adventure!” I called out, pulling myself up out of the water.

“Yeah! Let’s go!” Cassie exclaimed loudly, her drunken state slipping through a little.

I ran through the house, dripping water all over the floor. I dashed up to my bedroom to retrieve my keys and when I returned to the mysterious door, Cassie, still holding the fresh wine bottle, was waiting.

Candace, clearly curious but less enthusiastic than Cassie, strolled up as I began fitting keys against the door.

“Come on! Come on! Hurry up!” Cassie giggled.

“If this is the bat cave, I’m totally gonna shit myself.” I said as a key finally slid into the lock.

“Oh my gawd, that would be so awesome.” Cassie exclaimed drunkenly.

I turned the key and opened the door.

“Lemme see!” Cassie shrieked, pushing past me and into the dark room. I took a step inside and as I began fumbling for a switch, dim red lights came on automatically.

“Woah.” I said.

“What is it?” Candace asked, pushing past me into the room.

“This is totally better than the bat cave.” Cassie exclaimed.


Inside was what only could be described as a sex dungeon. I’d seen enough kinky porn to recognize several of the items. In one corner was a large, padded, red leather cross. Next to it was a huge wall filled with all sorts of leather straps, cuffs and whips.

Hanging close by was a sex swing, which I’d seen once before.

The opposite wall was mirrors from floor to ceiling.

On the far wall was another door.

There were several low, padded tables spread around the room and in the opposite corner was the biggest bed I’d ever seen.

“Oh this is fucking awesome!” Cassie shrieked before settling the wine bottle down and taking a flying dive into the middle of the bed.

“Wow.” Candace commented.

“You can fit, like 30 people in this bed!” Cassie screamed, rolling over and bouncing up and down in the middle of the huge mattress.

“Probably.” I commented.

Cassie flipped over and stuck her ass up in the air.

“Dick and pussy everywhere!” She exclaimed.

“What is all this stuff?” Candace asked, walking over towards the cross.

“Seriously? I thought you were kinkier than that!” Cassie exclaimed, jumping off the bed and skipping over towards her sister.

“I am! But I don’t know what all this stuff is for. I mean, spanking and stuff, but what’s all that?”

“Well, big sis, let me show you!” Cassie grinned.

I slowly strolled over towards the corner as Cassie grabbed an assortment of straps off their pegs and began attaching them to Candace’s wrists.

“Uhm, I don’t know about this.” Candace stammered nervously as Cassie pushed her backwards against the padded cross.

“You scared? Come on it will be fun. Won’t it Carter?” Cassie asked, grinning at me.

“Yup.” I grinned, sitting on one of the benches to watch.

Candace stared at her sister nervously as Cassie attached her wrists to rings on the cross with the confidence of someone who clearly had experience.

“Not your first time I take it?” I asked.

“Nope.” Cassie replied happily as she knelt down and attached Candace’s ankles to rings.

“That’s a story I need to hear.”

“Later. There we go, all done!” Cassie announced triumphantly.

“So, what do we do to her now?” I asked.

“Anything we want.” Cassie replied seductively.

“Show me.”

Cassie spun around towards the rack of toys and walked back and forth in front of them as if selecting a weapon. She finally grabbed a blindfold and turned back towards Candace.

“Here ya go. Let’s start here.”

“Cass, I don’t think that this...” Candace stammered.

I cleared my throat hard. Candace looked up at me and then slammed her mouth shut.

“It’s gonna be fine!” Cassie giggled, slipping the mask over Candace’s head.

“Now what?” I asked.

“Now, we torture her.” Cassie grinned, spinning back towards the wall. I watched as she pulled a large fluffy object off a hook and slipped it over her hand.

“What’s that?” I asked as she turned back towards Candace.

“Shush, you’ll spoil it!” Cassie scolded. I watched as she placed the fuzzy item on Candace’s side and slowly drug it up her body.

“Oh gawd!” Candace exclaimed, shivering.

“Uh huh, isn’t that soft?” Cassie asked, running the glove all over Candace’s chest and neck.

“Oh that feels so good.” Candace moaned.

“Try it on her nipples.” I suggested.

Cassie reached behind Candace’s neck with her free hand and tugged on the string holding her bikini top together. The fabric fell away, exposing her breasts. Cassie quickly began to gently tease her sister’s breasts and nipples with her fuzzy glove.

“Oh gawd. Oh gawd oh gawd oh gawd!” Candace cried out, pulling against her bonds.

“Are her nipples hard yet?” I asked.

“I dunno, let me check.” Cassie replied, leaning down. As I watched, Cassie opened her mouth and sucked one of Candace’s nipples into her moth. Candace moaned loudly as Cassie gently suckled on one and then the other.

“Please. Please don’t. Please.” Candace begged as Cassie shoved her gloved hand between her sister’s thighs.

Cassie spun around and walked back towards me, pulling off the glove. She grabbed the bottle of wine from me and took a long drink, and then stepped back to the wall of implements. She shoved the wine bottle back into my hands and then pulled off a rubber ball with straps hanging out of it.

“Is that...” I started to ask as Cassie turned back towards Candace happily.

“Yup!” She replied, thrusting the ball into Candace’s mouth. Candace began to thrash around as Cassie buckled it behind her head. She then pulled the blindfold off her head. Candace’s eyes were opened wide in fear as she looked from Cassie to me.

“That’s hot. Now what?” I asked.

“Let’s see what else we got!” Cassie replied happily. She returned to the wall of toys and then knelt down to several plastic drawers underneath.

“Holy shit, you’ve got a sybian! Fuck me, you have two sybians!” Cassie shrieked.

“What’s a sybian?” I asked as Cassie pulled out a low rounded device that looked like a stool. As I got closer, I saw that the ‘stool’ had a dick sticking out of the middle of it.

“You sit on it and then go for a ride at a hundred miles an hour!” Cassie explained.

“You’ll have to show me later.”

“Oh you bet your ass I will! These things are like a thousand dollars and you have TWO of them!”

“Pays to be rich I guess.” I shrugged.

Cassie nodded and pulled open another drawer.

“This will work for now.” She said, standing up with a grin. In her hand she was holding what looked like an oversized microphone.

“What’s that?” I asked as she bent over and plugged it into the wall.

“This is a Thunder Stick!” She grinned.

“What does it do?”

“It gives back massages.”

“Oh, that’s not very sexy.”

“It also makes girls cum like a bazillion times.” She giggled, rolling a dial on the handle. The toy came to life and I could see the top part start to vibrate.

“Oh, I get it.”

“Yup, now watch this.” Cassie said, turning towards Candace. Her older sister’s eyes opened wide as she moved the toy downwards towards her crotch.

The sound changed as Cassie pressed the toy against Candace’s covered mound but Candace immediately began moaning into her ball gag. She jerked wildly, yanking her limbs against her restraints.

“Oh yeah. Oh yeah that’s hot. You’re all mine now babe.” Cassie said happily. She fumbled with the handle for a moment and then I heard the speed of the toy double.

Candace shrieked and her whole body jerked hard enough that the cross shook.

“Oh yeah babe, isn’t that nice?” Cassie teased.

“Uh huh. Uh huh. Uh huh. Uh huh.” Candace moaned, mumbling against the gag.

“Good, here, hold it for me.” Cassie giggled. I watched as she pulled Candace’s bikini bottoms outward and then thrust the toy inside the fabric.

Candace’s eyes opened wide as Cassie backed away.

“See, its hands free! Just stay there a while, I’ll be back.” Cassie giggle, spinning around on her heel towards me.

“That’s awesome. Where did you learn all this shit?” I asked as Cassie walked towards me.

“I know people. One of my friends is a professional dominatrix.”

“Is that so? So, are you?” I asked as Cassie grabbed the wine bottle out of my hand and took another long drink.

“I know how to be on top, but I really prefer to be on bottom, if there is someone strong enough to take me.” She replied seductively.

“To take you huh?” I asked.

“Uh huh.” She grinned.

I stepped forward, pressing my body against hers and forcing her against a table. I leaned down to kiss her, but she jerked away.

“Come here bitch.”

“Make me.” She grinned, taking another big drink from the wine.

We stared at each other for a while, sizing each other up. Out of nowhere, Candace shrieked, snapping both of our attention. Cassie turned towards her sister, grinning. My eyes flickered towards the twitching girl on the cross but then I saw my opening. My hand shot up, grabbing the back of Cassie’s hair.

“Nuhnnnhh! No fair! I wasn’t looking!” Cassie gasped as I pulled her head backwards. Her arms flailed around and she dropped the wine bottle on the floor. It tipped over, spilling a little.

“That’s just too fucking bad.” I growled, pulling her hard enough to make her walk backwards. Clearly off balance, I shoved her forward, forcing her over one of the padded tables.

“Oohhff!” She gasped as the edge of the table dug into her stomach. I ran around to the other side of the table and I spied a conveniently placed roll of rope underneath it. I picked up the roll and quickly wrapped it around Cassie’s wrists, then attached it to a ring underneath the table.

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