My Fiancé Courtney Helps Ch. 04

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Double Penetration

Friday and Saturday’s events were fresh on my mind as I woke up next to Courtney Sunday morning. It was such a phenomenon to me – seeing my beautiful, angelic fiancée sleeping peacefully next to me, looking as innocent as could be, but at the same time knowing how slutty she had been the last couple of days, swallowing mine and our landlord’s loads and even fucking her while she sucked his dick. Thinking of this of course made me unbearably hard, and so I put my arm around her as we spooned to pull her closer, gently nuzzling her neck to wake her up. As she started to wake, I grabbed her hip and rubbed up and down her thigh, moving closer to her pussy. She gradually became more awake and as horny as me, her pussy becoming wetter. I kissed her from her neck down to her sensitive nipples, then down her tight stomach and to her pussy where she gladly welcomed me with open legs and a gasp as my tongue flicked against her pussy and tasted her sweet wetness. She moaned as I lapped at her pussy, grabbing her perfect breasts and pinching her nipples. Her hand moved to my wrist and gripped it hard and she arched her back and let out one last loud moan before shuddering into a blissful orgasm.

“Mmm that was a good morning,” she purred.

I moved back up to lay next to her and gave her a kiss, and she moved down to return the favor for me, eagerly taking my cock into her mouth and taking it all the way to the base. After only a couple times taking my whole length, I erupted down her throat, of course with the help of again envisioning the previous night’s events of her sucking Chris’ big fat cock while I fucked her from behind.

“Yes it is a good morning!” I joked. Courtney moved up and we cuddled in bed, sharing the post-orgasm relaxation. “I woke up hornier than usual,” I informed my fiancée.

“Yeah I could tell, you got me going pretty fast too. Last night was pretty crazy, huh?”

“I sure was a surprise waking up to you and Chris. Not a bad surprise though,” I confessed. “It got me really hard, and that was really hot fucking you while you sucked him.”

“Mmmm I liked it too. A lot. It was hot being filled from both ends. I never thought this would turn me on so much but it does.”

“Believe me, me either!” I exclaimed. “I thought you’d be repulsed by Chris. I mean, he’s not exactly in the best shape or the best looking.”

“I know. He’s fat. A lot older than me. And just sloppy. But something about that makes it naughtier and turns me on more,” Courtney admitted.

“I think I know what you mean. This whole scenario is so forbidden that it turns me on even more. And knowing that he must love being with such a young, gorgeous, sexy girl like you,” I complimented her. “He’s probably never been with anyone like you, and especially now with him being all old and fat.”

“Thanks baby. Yeah something about it just makes me horny. I feel like I should be repulsed, but I don’t know. He’s bossy and I like that, and his cock. Oh my god, I’ve never seen one that big! I never would have expected that on him!”

“Haha I still don’t know how you get it down your throat, he’s like twice my size.”

“I just try to concentrate on making him feel good,” she explained, which sent a surge through my dick and got me thinking.

“I wonder why he’s not here now. I thought he’d be here when we woke up, or I’d wake up to you two like last night.”

“Maybe he’s busy?”

“Yeah, maybe… Why don’t you go down to his room and see if he’s there?”

“You really want me to?” she asked me.

“Yeah” I said with a dry throat. “Do you want to?”

“Mhmm,” she purred. I reached down to her pussy and could feel her pussy still soaking wet. Obviously she did want to.

“Get dressed and then let me know how it goes whenever you get back,” I told her and kissed her forehead. “I’ll be waiting here.”

With that, I watched as my beautiful blonde fiancée got dressed for the day. She quickly threw on some yoga pants and a top and straightened her hair before putting it into a ponytail. She told me she’d be right back and gave me a kiss before heading out the door. I lay in bed, wondering if Chris was even home or not. After waiting five minutes and Courtney not returning, I figured he must be home and wanted the company. My mind was racing just imagining what was happening, and I started to jerk off picturing Courtney on her knees for our landlord. I blew my load on my stomach, and then waited for her to return. I waited for about 15 more minutes until I drifted back to sleep.

I woke up when I heard the sound of our door closing, and Courtney walked in the room. Her hair was disheveled and her mascara was a little smeared. I looked at the clock and she had been gone for about two hours, which was much longer than I had thought she’d be gone. Courtney removed her clothes as she got closer to the bed, revealing bite marks over her perfect tanned breasts, and red hand prints on her ass. She got in bed next to me under the covers and immediately began kissing me. pendik escort

“I need fucked hard, baby,” she begged.

“Mmmm tell me what happened,” I ordered her.

“I knocked on his door and he was surprised to see me there, but he welcomed me in. He asked what I needed and I just started taking off my clothes and got on my knees in front of him and pulled down his sweatpants and started sucking his huge dick. It was pretty hot surprising him like that and I could feel my pussy getting wet.” Courtney started stroking my hardening dick while she continued. “I gave him head for about 15 minutes before he pulled out and came all over my face and tits, and they were covered. I don’t know how he cums so much. I asked him if he liked the surprise and he said he loved it, and I started to get my clothes to leave and come back to you, but he told me to stay. He had me fix him breakfast and clean up around his place naked, and then had me give him head again while he did some work and talked on the phone with some potential renters. In between doing work, he’d occasionally slap my ass really hard, or pull me up and suck on my titties and finger me. I was so horny that I orgasmed when he started fingering me and he kept calling me dirty names and made me keep sucking him. After he came the second time, in my mouth, he said I could leave because he was going out, but he’d stop in later. Oh yeah, he also asked if you had work and I told him that you do at 6pm, and he said he’d probably be stopping in sometime around then. I’m excited, his cock is so big and he cums so much. I can’t get enough of it. Now fuck me baby, I REALLY need it!”

Needless to say, I was rock hard by this point, and she climbed on top of me and easily impaled herself on my dick. Apparently recounting her story made her incredibly horny as well as she was soaking wet and was able to take it all in one stroke. She rode my dick with such enthusiasm that, coupled with her retelling of what happened earlier, I came in just five minutes, even though I had already cum twice before. I embarrassedly apologized, and made it up to her by flipping her on her back and eating her out until she came with a violent orgasm.

We relaxed the rest of the day until I had to get ready for work. I kissed her goodbye and told her to have fun, knowing Chris would be stopping over shortly. Work again seemed to take forever, and I eagerly rushed back to the apartment when I clocked out. Chris and Courtney were both on the couch naked, playing cards and taking shots of liquor. They both seemed to be in good spirits and greeted me as I came in.

“Come join us, James!” Chris offered. Before I couldn’t stand him, and he always seemed so morose, but he was cheerful as of late, and I can guess why. He was a lot more likable now though; he didn’t just scowl when passing in the hallways, and we’d actually greet each other. I joined them and we half-heartedly played poker, focusing more on drinking and conversing. It did seem a little strange, my fiancée and my much older landlord sitting comfortably naked next to each other, as if it was normal. But the alcohol loosened me up too, and we were all having a good time. Chris shared some stories of horrible tenants he’s had in the past, which actually made me understand where he was coming from when he first gave us the ultimatum. I saw Chris in a different light, and we got along, which I thought wouldn’t ever happened. Courtney must have really sparked a fire in him and brightened him up.

“You know James, Courtney told me that it was your idea for her to come down and surprise me this morning. So, er..thanks.”

It sure was a change hearing Chris use manners. “Yeah, I figured you’d like that. And she was pretty horny this morning so I knew she’d enjoy it too,” I explained, glancing over to Courtney who blushed.

By 1am, we were all pretty drunk and slurring our words. I was surprised Court had stayed up this late and gotten so drunk since she had class in the morning, but I didn’t want to ruin a good night by bringing it up. Chris, still sitting next to Courtney, grabbed her breast and told me, “You’re a lucky guy James. You got a sexy slut for a girlfriend.”

“She’s been real slutty lately, haven’t you babe?” I directed toward her.

Courtney was drunker than both of us and just nodded with her eyes closed and her head leaned back. “Mmmmmhhmmmm. I loooovee taking care of my mennn,” she slurred. Without being directed, she grabbed Chris’ big cock and started stroking it to hardness. I got up and walked in front of her and offered my dick to her mouth, which she greedily accepted. I could see her pussy glistening with wetness so I got behind her on the couch and had her arch her ass up. Chris scooted back on the couch and lay back. I sank deep into her wet pussy and she moaned then started bobbing up and down on Chris’ fat dick.

I fucked her like that for about 20 minutes, eventually cumming inside her right as she had her orgasm. Chris still had yet to cum, and in my post-orgasm maltepe escort state with the alcohol taking its toll on me, I sank down into the couch opposite them and watched as Courtney worked to make him cum. Finally Chris bucked his hips and emptied his load into her mouth, which turned out to be the fifth load of the day that he gave her. I found out later that while I was at work, she had blown him twice. We all drifted off into a deep sleep.

I was the first to awaken, feeling the terrible hangover. I looked toward the opposite couch and Courtney was lying on Chris’ big chest, which was a strange sight to see. Up until then, I had only seen her doing sexual acts with him. Now I was looking at her sleeping peacefully on his massive frame, which dwarfed hers. I made some coffee for us all, and woke them up when it was ready. Chris thanked us for the coffee and for the fun before parting.

“See ya,” he said to me, and then kissed Courtney goodbye.

“How’re you feeling, hun?” I asked my stunning fiancée.

“Like shit,” she groaned. “You?”

“Same. Maybe you should just skip class today and nurse the hangover. I know that’s what I’ll be doing before work tonight.”

“Yeah, I think that’s a good idea,” she chuckled.

The rest of Monday was uneventful. We stayed in bed for most of the day, taking naps and Advil every couple of hours. When I came back from work that night I was kind of surprised, and admittedly a little disappointed, to find out that Chris had not visited. I figured he must have been sleeping off his hangover too. Court and I made love gently that night before falling asleep. Tuesday through Thursday we were back to our normal selves, and the routine picked up where it left off. Courtney and I fucked like rabbits, and Chris stopped over frequently for some oral relief. Wednesday and Thursday morning Courtney visited Chris and gave him a proper ‘goodmorning’ before coming back and riding me while telling me about it. Thursday night he spent the night again, knowing it was his last night before I got my paycheck and paid him back. I lost count of how many times she swallowed Chris’ load or took it all over her face and chest those last couple of days. Our sex life was through the roof and I was reaping all the benefits of Court taking care of our landlord’s needs.

However, Friday soon arrived. I stopped in at work to collect my paycheck and there was enough money in it to pay the rent for last month and this month. I cashed it, and stopped at Chris’ room on the way back to ours.

“Hey Chris, here’s the payment for last month and this month. Um..thanks for giving us a little time..” I awkwardly said to him as I handed over the envelope with the payments.

“Yeah, no problem..” he responded.

“See you around,” I said as I left his room. I made my way back to my apartment and found Courtney on the couch reading her textbook.

“Hey babe, I just paid back Chris, so we’re all good on our debt.”

“Oh, great!” she replied, but something seemed a little off in her response, as if she feigned excitement.

I admit, I too wasn’t as thrilled as I had imagined I’d be a week ago. Everything was so exciting and wild. But it was for the best. We were getting married in some months, after all. Life was back to normal.

However, the next couple of days seemed a little different, as if something were missing. I thought maybe with school on her mind, Courtney was a little stressed. We still had sex, but it wasn’t as electrifying as before. Our sex life was still healthy, but it was lessened from what it just was. Courtney hadn’t orgasmed from me fucking her since the last time with Chris, and I felt I was just not cutting it.

Friday evening, a week after we had paid our dues, I called down to Chris’ room. Besides passing him in the hallway for short greetings, this was the first time we really talked.

“Hey Chris, it’s James.”


“Can you come up here and take a look at the window? It’s not shutting all the way. It’s letting cold air in.”

“I’ll be up in a minute,” he responded.

About five minutes after I hung up, Chris knocked on the door and I let him in.

“Which one?” he asked me. I pointed to the one in the living room. He walked over to it and studied it for a second before turning back around and facing me. “What’s wrong with it? It’s closed, there’s no air coming in.”

Just then, Courtney came out of the bedroom in her sexy lingerie; decked in stockings and a tight nighty.

“Hey daddy, I’ve missed you,” she purred at him with a sultry tone.

Chris looked to me as if to question what was going on, but I cut in before he could answer.

“We talked last night, and we both think that as oddly as it sounds, our sex life was better when you had your visits with Court. And she wants to keep seeing you. Also, we’re okay with you going further with her than just oral. I don’t need to mention that it’s obvious you’re a lot bigger than me, kartal escort and I haven’t been able to make her cum or last as long as I wish, so maybe you could help out. If you want, of course.”

The expression on Chris’ face looked like he had just hit the lottery. He composed himself and replied, “Fuck yeah. Come here you little slut, I missed you too.”

Courtney went over to him and they made out for a couple minutes, and I could see Courtney was getting really into it. She really must have missed servicing our old fat landlord. And no doubt she was excited and nervous to experience what it felt like to have him inside of her; the only other person beside me to do so. I was very excited and nervous as well. We moved to the bed and Courtney sucked on his fat dick while he lay on his back, and I got in between her legs and lapped at her already-wet pussy to get her ready. Once Chris was nice and hard, Court stopped sucking him and then got up and straddled him, resting her hands on his big belly. It was the point of no return. Using one hand behind her, she grabbed hold of his monstrous dick, and guided it to the opening of her hovering pussy. I switched my gaze between her face and her pussy, watching in amazement as she slowly lowered herself on his huge cock, impaling herself. The look on her face was what really got me; her eyes were closed and she had an expression as if it were the first time she were being fucked.

There was a hint of pain, but mostly pleasure as she went deeper and deeper on his big, thick cock. Moans and short breaths were escaping her mouth as she finally lowered herself completely on his massive member. She rested on the base for a while, and then placed her hands on his big belly and retracted her pussy, coming all the way back up until the head. I watched in amazement and wondered how she could fit that huge thing in her tight little pussy. She lowered herself all the way back down, a little faster this time, and this repeated until she got into a rhythm. Not even two minutes later, she was slamming her pussy down on his cock and cried out in the loudest orgasm I’d ever heard. I was jerking off watching my sexy blonde fiancée riding this old fat mans big cock, and erupted in a massive orgasm that coincided with hers, covering my stomach and hand with my cum.

After she came down from her orgasm, she lowered her body onto Chris’ and he grabbed the back of her head and made out with her while she moved her hips up and down on his cock. In no time, I was hard again watching them in action. Chris grabbed onto her and flipped her over in one motion, remaining inside of her. His massive body covered her tiny frame, completely hiding her from view except for her arms and legs wrapped around his torso as he pistoned in and out of her tight pussy. After she came again, they switched positions and she got on her hands and knees facing me and he got behind her, holding up his belly and placing it on her ass as he entered her from behind.

“Fuck yeah daddy. Fuck your little girl. I missed your big cock. Oh!”

Chris slapped her ass intermittently. “You just couldn’t stay away from my big cock, could you?”

“No, it’s all I kept thinking about. I couldn’t wait to have it back in my mouth and feel it in my pussy.”

“Show him what a slut you are,” I encouraged her while moving up and offering my dick to her hungry mouth.

“Mmmpphhh,” she moaned onto me while getting fucked hard by Chris, only taking her mouth off my dick to talk. “You fuck me so good daddy, I want to make you cum. I want to make you both cum!” She put her mouth back on my dick. Every time Chris pounded into her, it propelled her forward and my dick slid down her throat.

“Fuck I’m gonna cum in your tight little pussy. You want it, whore?” Chris grunted.

“Yeah give me your cum! Cum in your little slut!” she urged.

All three of us seemingly came simultaneously. My first spurt filled her mouth, but her orgasm caused her to release my dick and so my next three spurts covered her face, and Chris filled her pussy up with his cum. After we had all come down, Chris sat back, plopping his softening cock from her pussy. She turned around and said “Let me clean you off,” then plunged down and sucked his dick. With her ass now facing me and her back arched, I could see just how much Chris filled her up. Her pussy was gaping from his fat cock, and it was absolutely leaking with cum. Seeing this made my dick refuse to go down, and I scooted behind her and sank my dick into her slippery pussy. I slid in all the way easily, and could feel her pussy wasn’t as tight as I was accustomed. My loving fiancée continued bobbing up and down on Chris until he was hard again. I watched her sexy little tan body and blonde head move up and down on his shaft while I pounded into her from behind, wondering if she really even felt me.

Nevertheless, this previously unknown sensation of a slippery pussy got the best of me and I was emptying myself inside her soon, adding my cum to Chris’.

“Let me feel that little pussy again. C’mere back on my dick,” Chris ordered her after I fell back. I watched my sexy blonde fiancée ride his dick again to orgasm, and then make out with him until he came for the second time inside of her.

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