Double Dipping Ch. 06

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Jim has one erotic adventure after another, and finally makes Amy a woman.
5.3k words
4.68
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Part 6 of the 6 part series

Updated 10/06/2022
Created 03/09/2001
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Erlikkhan
Erlikkhan
3,988 Followers

Jim, recently divorced, visits Deb, a female friend from high school and her daughter. Her husband is out of town. After a few glasses of wine they end up having oral sex and finally fucking. The next day innocent daughter Amy teases Jim and ends up with cum all over her. Deb comes home and gets fucked again and again. Amy continues to tease Jim and ends up with a cock in her mouth. Their neighbor invites Jim over and they end up in an oily fuck session followed by some wild oral and anal sex in the shower and bedroom. Jim meets Amy's friend Jenny and introduces her to oral sex. Deb continues to make demands on his overworked cock as does her neighbor. To get away Jim decides to visit their local office.

I showered, dressed and decided to go by our local sales office for a brief visit. Sitting behind the receptionist desk was a young, absolutely stunning brunette with big brown eyes and a nice rack poking out of the tight green top she was wearing. Her name was Rachel. When she stood to escort me back to the Dan's office, I couldn't help but stare at the yellow micro-skirt she was wearing which barely covered the rounded spheres of her shapely ass.

"So what do you think of the new receptionist?" asked Dan when she had closed the door. "She's only nineteen, but the customers love her. And she doesn't mind going the extra mile to help close a sale, if you know what I mean."

Dan was a typical crude salesman, but effective. I assumed if she was fucking customers, Dan was getting more than his share, and probably others in the office as well. I could only wonder what it would be like to fuck a sex goddess like Rachel. My cock started to stir at the thought.

"I know what you're thinking. God would I like to sample a piece of that but I'm from corporate so I have to be on good behavior. Well, shit, Jim. You got to let your hair down a little. I tell you what. I'm going to ask young Rachel to come back in here and be extra nice to you, okay? The rest is up to you."

I should have said no. This was the type of thing that I could lose my job over, or at the least get blackmailed with. But my cock was doing the thinking so I just sat on the couch while he buzzed Rachel back into the office and told her to close the door. "Rachel, honey, Mr. Riley here is from corporate. He's real important. But he's been kind of lonely lately. His wife left him a few months ago. I thought maybe you had some ideas on what we could do to cheer up Mr. Riley."

"Oh, you poor thing," Rachel sympathized looking at me with those big brown eyes while she squatted in front of me and put her hands on my thighs, "Just relax, Mr. Riley, and let me give you a massage."

Rachel climbed onto the couch and straddled me with her knees. She put her hands on my shoulders and began kneading them with her strong hands. Her large tits and erect nipples were poking through her top inches from my face.

"Go ahead, Jim. Suck on them there beauties. Believe me, they taste as good as they look. You wouldn't mind if Mr. Riley sucked your titties, would you Rachel?"

"You can suck my tits, Mr. Riley. I'd really like it."

Rachel pulled her top up over her large melons and unclasped the front hook bra. Two well rounded grapefruits capped with large dark brown nipples bounced freely right in front of my eyes. Rachel erased any second thoughts I had by feeding me the nipple of her right tit. I sucked it into my mouth and flicked my tongue over the nipple. I started pinching the other nipple, rolling it between my thumb and forefinger. Then I switched to the other nipple. Rachel was moaning as she pulled my head tightly to her tits.

"Oooohhhhh. Mr. Riley. oh god that feels so good. oooohhhhh. put your hand between my legs, Mr. Riley. I need something there. please, Mr. Riley."

I slid a hand up between her thighs and quickly discovered Rachel was not wearing panties and was shaved except for a small patch above her pussy. My fingers spread her cunt lips and two fingers slipped inside her. Rachel began to gyrate her ass against them.

"Oh, Mr. Riley, I need you to fuck me. I need you big cock up my hot pussy. Please, Mr. Riley, fuck me with your big cock."

I fumbled with my trousers until I was able to free my very stiff and throbbing fuck pole. I rubbed it across her juicy gash until it slipped inside. Rachel pushed down against me until her hot cunt was fully impaled. Then she started riding me hard, grinding her pussy and rotating her ass as she lifted up and slammed down on my engorged cock. I sucked her nipple back in my mouth and nibbled on it with my teeth. Rachel was gasping and moaning and screaming obscenities.

"Now, sweetheart, that's a real pretty ass bouncing up and down on Mr. Riley's cock. I think I'll come over there and fuck it. Would you like that, Rachel?"

"Oh yes. please. I want you to fuck my asshole while Mr. Riley fucks my pussy. I want to feel two cocks going in and out of me and then squirting cum in me."

Dan moved in behind Rachel and slowly worked his cock into her ass. This caused Rachel to tighten her pussy around my cock. The pressure felt incredible. I wasn't going to last much longer. Dan started fucking her asshole hard and fast causing her pussy to squeeze against me as it slid up and down my cock. I couldn't hold back anymore. My balls uncorked and I started spraying hot sticky cum into Rachel's belly.

"Oooohhhh. Mr. Riley. yeessss. shoot your hot cum in my pussy. oh god, I can feel it squirting against my cunt. oh, Mr. Riley, I'm gonna cum. oh god. here it cums. uuuunnnnggghhhh. aaaaahhhhhhh."

Rachel was thrashing about as her orgasm consumed her. A mixture of cum and cunt juice seeped past her stretched cunt lips and drooled down my cock. Just as I was finishing, Dan pulled out of Rachel's ass.

"Rachel, baby, why don't you finish me with your mouth. I want to cum all over your face and titties, sweetheart."

Dan climbed up on the couch and dangled his cock in Rachel's face. She didn't hesitate to gobble it into her mouth and down her throat. She wrapped her hand around the base and attacked it aggressively with her mouth and tongue. About a minute later Dan grunted. Rachel pulled his cock from her lips and aimed it at her face. Gobs of thick white cum splattered her eyes, nose and hair. She pointed him at her tits where he dumped the rest of his cum. I was still in her cunt and had slowly deflated while she was getting splattered. When I finally pulled away, the front of my trousers were a mess.

"That was real nice, Rachel baby. You made Mr. Riley feel real welcome. Now go clean yourself. Mr. Penske and his lawyer will be here in an hour."

As I was leaving Dan told me I could come back for more of Rachel anytime I wanted. As much as I hated him, I knew I would be back.

I returned mid afternoon. Amy and Jenny were out by the pool with two boys about their age. I assumed one of the boys was Tim from the way Amy flirted with him and the other was Scott because Jenny was sitting on his lap. They were wearing bikinis, although not as skimpy as the one Amy had worn yesterday.

I decided to watch from my room where I couldn't be seen. Things might get interesting. Well, things got interesting quickly when I pushed open the door. In the middle of the bed was a third young couple. A well-built young man was wedged between the uplifted legs of the girl below him with his swimsuit pulled down his thighs. His ass was rapidly moving up and down as he repeatedly thrust his cock into his partner's hot cunt. She was moaning softly with her arms wrapped around his neck. I stood and watched.

"Oh shit, baby, I'm getting ready to cum," he declared after several minutes of hammering her.

"Not in me. please."

"Okay, then let me cum in your mouth."

"I don't know... of god it feels so good. I guess. aaaaahhhhh. okay."

He pulled his nice sized young cock from her slimy cunt. She slid down between his legs until his cock dangled in her face. He grabbed the back of her head and began fucking her mouth. Her ass hung over the side of the bed. She had her feet on the floor and her legs spread wide. I had a perfect view of her young cunt open wide and glistening among a sparse patch of dark curls. It was a very tempting sight. Then I thought to myself, `Why not. It's my room. Besides, she might like it and I doubt he would notice.'

I got on my knees between her spread legs and reached out with my hand until my fingers brushed lightly across her pussy. I pressed a fingertip over her clit and started rubbing it in circles. Her body responded by gyrating against me. I slipped two fingers inside her steamy cunt. She humped against them as they slid in and out of her juicy pussy. I leaned forward until I was able to flick my tongue across her clit. Then I took my fingers from her cunt and clamped my mouth over her pussy, driving my tongue deep inside her. She started humping my face furiously. The intensity of her muffled moans and groans increased as she became more excited.

The young man with his cock in her mouth didn't know I was there. I'm not sure she did either, she just knew something incredible was happening to her pussy. I decided it was time to fuck her if she would let me. I quickly shed my clothes and bent my knees to position my throbbing cock at the entrance to her steamy treasures. I heard a deep grunt as the young man she was sucking started to cum in her mouth. I chose this moment to shove my cock up her cunt. She was tight but juicy enough that I buried myself in three quick strokes She let out a muffled cry as I was going inside her, which caused the cum spewing cock to fall from her mouth. He started spraying her face with globs of sticky white goo.

I was already thrusting my cock in and out of her tight pussy when he finally finished and collapsed forward, rolling off her. Her pleading eyes stared at me, but she made no attempt to push me away as I continued to fuck her pussy. Her face was covered with cum which drooled down her cheeks. I reached down with my thumb and began rubbing her exposed clit poking out between her puffy cunt lips. She closed her eyes and let out a small sigh of pleasure.

As I continued to fuck her, she began pinching her nipples and squirming against me. I finally pulled out and rolled her onto her stomach, then lifted her ass and slipped my cock back into her steamy cunt. I reached around and cupped her tits while I hammered her from behind. She started to gasp and moan in a way that told me she was nearing orgasm. I glanced at her previous partner and saw a look of panic on his face as he watched us fuck. I also noticed that his cock was still hard.

"All right, kids, we're going to do a little three-way. Honey, I want you to suck his cock while I continue to fuck your sweet little pussy. Get in front of her, son, and feed it to her, okay? Good. Okay, now hold on. I'm going to fuck you hard until I get ready to cum. Then I'm going to squirt it all over your pussy and ass."

As I started slamming into her she had the first of a series of intense orgasms. She kept losing the cock in her mouth as she screamed out. I told him to grab her head and shove it deep. She gagged at first but finally figured out how to open her throat and hold him there. I felt my balls shrink and my cock swell. I barely cleared her pussy when the first burst of cum sprayed along her cunt lips and up the crack of her ass. I proceeded to dump several more gobs of goo all over her pussy, asshole, thighs and cheeks. When I was finished, beads of cum were streaming down the inside of her legs.

The young man in her mouth didn't last much longer. He was buried deep in her throat when he started cumming. This time she didn't gag and proceeded to drain his cock and lick him clean. She finally collapsed onto the bed and looked back at me.

"Sorry for the interruption. I'm staying with Amy and her mom, and you guys were in my room. I just couldn't resist your pretty little pussy when I saw it staring at me. I hope you didn't mind sharing."

"Um. well. I. um. it was. oh god. um. I don't know. What do you think, Greg?"

"Hey, I came twice. And don't pretend you didn't love it, Sarah. Everyone knows you'll fuck anyone, anywhere, anytime. It's not like you have a reputation to keep or anything. A threesome was really cool. I'm sure Sarah's done it before, but it was my first. But, Jesus, you did scare the shit out of me. I thought you were some kind of geezer pervert and might kill us all after you got off."

"Hey, I'm not like that," Sarah protested, "and I've never been with two guys before. well, not both in me at the same time. Besides, I was a virgin until I met Tommy last year. And Greg, I just let you fuck me because I felt sorry for you. I have to admit, though, doing it with two guys was a real turn-on. I've never cum so hard."

I looked out the window and saw that Amy and Jenny were in the throes of a heated make-out session with their partners. Amy and Tim were standing with their bodies pressed together. His hands cupped her ass cheeks. Amy had a leg hooked around his and was humping her pussy against him. Jenny was in Scott's lap squirming against the bulge in Scott's suit while his hand massaged Jenny's well-formed tits. As I was watching, Amy slipped her hand into the front of Tim's trunks and wrapped her hand around his hard cock. Sarah, still naked, joined me at the window while Greg went to pee.

"Wow. Look at them. God, I can't believe they're still virgins... or at least that's what they say. I think Amy is going to get a sticky hand if she keeps it up."

Scott removed Jenny's top without any resistance. He squeezed her two free hanging beauties and pinched her nipples. Jenny broke the kiss and threw her head back, biting her lip as she reacted to the pleasure surging through her body. Scoot kissed down her neck to her tits and began sucking on her nipples. His hand moved between her legs, and he started rubbing her pussy through her bikini bottoms. Jenny's face was all scrunched up like she was about to have an orgasm. She spread her legs wide to accept his probing fingers.

I reached down under Sarah's ass and rubbed my fingers over her pussy. She spread her legs and tilted her ass up to give me better access. Two fingers quickly sunk deep inside her. Once they were well lubricated, I took my index finger and pressed it against her asshole. She looked over at me uncertainly, but never said anything as I rotated the tip of my finger up her ass. She bit her lip and gritted her teeth as my finger went deeper and deeper until it was completely buried. I began digging it around inside her. She rotated her ass against me indicating pleasure at what I was doing.

"God, that feels really good up my ass like that. oh yes."

Outside we watched as Amy dropped to her knees and pulled Tim's swimsuit down exposing his rock hard cock. She wrapped her hand around it and stroked him a few times before leaning forward and licking the tip with her tongue. She opened her mouth and let him slide between her lips. Amy started using her expert oral skills with which I was quite familiar.

Tim didn't last long. When he started to cum, Amy pulled him from her mouth and hosed down her face and tits, then put him back to swallow the rest of his load. She had a hand inside her bikini bottoms and was frantically fingering her cunt while he was spraying cum all over her. Just as he was finishing Amy started shaking and convulsing with her own orgasm.

"God that's hot. Amy's been. oooohhhh yes. practicing. mmmmm."

Greg returned and couldn't help but notice my finger up Sarah's ass. Sarah reached out to him with her hand and started rubbing his semi-limp cock. I slowly worked a second finger up her ass, which caused her to squirm and moan even more. I told Greg to get the bottle of baby oil from the bathroom. I had him squirt it all over his cock while Sarah continued stroking him until he was fully erect.

Outside Scott had worked his fingers under Jenny's bikini and was thrusting his fingers in and out of her cunt. Jenny rolled off Scott's lap until she was lying on the lounge chair with her knees in the air and her legs spread. He shifted with her, keeping his fingers buried up her steamy fuck hole. They started kissing again as he pumped his fingers rapidly in and out of her cunt. Jenny grabbed his head and started pushing down. He stopped briefly to kiss her tits, but she kept pushing until his head was between her legs. She threw her legs in the air, ripped off her bikini bottoms and pulled his mouth to her hot little pussy. Scott must have figured out what to do because Jenny began squirming and thrusting her pussy up into his face.

"Sarah, I'm going to take my fingers out of your ass. Greg, I want you to get behind her and press your cock against her asshole. Then I want you to fuck her ass until you cum inside her. But don't do it until she asks you to. Go ahead, Sarah, tell him what you want."

"Um. I don't know. I mean, your fingers feel good and all but. well, maybe."

"Now Sarah, that's not anyway to ask. Tell Greg what you want."

"Um, I guess. well, okay."

"Okay what, Sarah. Tell Greg what he can do."

"Put it in my ass. You can put it in my ass, Greg."

"Put what in you ass. Do you want him to or not?"

"Yes. yes, you can put your cock in my ass, Greg. I want you to put your cock in my ass."

"And do what to you, Sarah?"

"Please. please, Greg, shove your cock up my ass. Fuck my asshole. Please."

"That's a good girl. Now grab his cock and guide it where you want it. Good girl. Go slow, Greg. That's it. Now start pushing deeper. Relax Sarah. Let him go in. Good. Push it deeper."

Greg slowly worked his cock all the way up her ass

"Tell him how much you like it, Sarah."

"Oh god yes. I love your cock up my asshole. uuuuhhhh. oh Greg, slam it in me. fuck my ass. mmmmpppphhhh. make me cum."

I slipped between Sarah and the window and began kissing her while rubbing her pussy. My cock had grown hard from watching Greg fuck Sarah in the ass. I bent my knees and guided it to the glistening lips of her cunt. I stared into her desperate eyes. My cock slowly inched its way inside her.

"MMMMmmmmm. oooohhhhhh. God yes. eeeerrrrr. I'm gonna cum. AAAAHHHH. UUUUNNNGGGHHH. OOOOOHHHHHH."

Sarah was totally out of control as Greg and I hammered her pussy and ass. Her juices were pouring down my balls. I could feel her tight cunt grab my cock as it slid in and out of her. She kept cumming and cumming until she seemed to lose consciousness, whimpering wistfully. We kept her limp body wedged between us as we continued to pound her pussy and ass. Greg finally grunted and blasted a load of cum into her bowels. When he pulled out, I propped her back against the window and continued fucking my cock into her lifeless body. Her eyes were open but glazed over as she stared at me with her arms loosely draped over my shoulders.

I looked out the window and saw that Jenny and Scott had traded places. Scott was sitting in the lounge chair with Jenny kneeling over him bobbing her head up and down on his cock. Her bikini bottoms were half way down her thighs. Scott had his arm around her ass and was plunging two fingers up her cunt while he was getting his cock sucked. Amy was sitting in the other lounge chair with her legs spread wide and sticking up in the air. Tim had his face buried between them as he licked and sucked on her sweet nectar. From the look on her face he was about to get drenched with pussy juice.

Sarah began moaning softly and then looked up at me with glassy eyes. I was hammering my cock into her and lifting her off the ground on each thrust. She put her hands on my shoulders and pulled closer. Her pussy was soaking wet and making smacking sounds each time I drove my cock into her. Sarah started gasping and moaning as she neared another orgasm.

Erlikkhan
Erlikkhan
3,988 Followers
12