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My girlfriend Chloe is a big scaredy cat.
It was a bit unexpected coming from a tall blonde goddess who could carry me around if she wanted, but it really didn’t take much to freak her out. She was fearless if it was something involving anything outdoors or related to sports, but ghosts and monsters got to her. It was pretty cute in a way: finding a little vulnerable side when she was normally so confident.
One time we had been sleeping together a few weeks after we started dating. We were both naked and had drifted to our own sides of the bed during the night in the hot room. It was around 3 in the morning when I woke up to a high-pitched scream from Chloe.
“What’s wrong?” I sat up at full attention, looking over at her in a panic. She was breathing fast with those lovely breasts jiggling as she did so, looking around the room frantically. She didn’t even respond right away; instead her hand started feeling around to my side of the bed. It landed on my chest, and she kept fumbling around as she searched for something lower and lower on my body. When she reached my penis, her hand wrapped around it and held on tight. The way she sighed in relief and laid back down made me think of a dog who’d just been put under a cozy safety blanket.
I was confused, to say the least.
“Uhhh, what’s going on?” I asked, laying back a bit myself as I realized there didn’t seem to be any immediate danger. “Did you have a bad dream or something?”
Chloe’s breathing slowed down more and more as she lightly fondled my balls and cock like a fidget toy. “Ugggh, it was so scary. There was a huge spider chasing me around, and I kept looking for you everywhere, but you weren’t there.”
I sat silently for a few seconds to let her catch her breath, but I couldn’t help myself. “And why was grabbing my crotch your reaction to that?” The amusement was evident in my voice, and she squeezed my balls a bit as a response.
“I was really scared, okay? Don’t make fun of me!”
“I still don’t get why holding my dick was the solution…care to explain?”
She kept holding my cock with one hand but planted her palm on her face with the other. “It’s really fucking embarrassing now that I think about it.”
“Hmmm?”
Chloe sighed, realizing I wasn’t going to drop it. “Ok, I know it’s going to sound really stupid, but when I was looking around for you in my dream, I just felt like I needed a man like you to protect me. So when I woke up, that’s all I was thinking. ‘I need a strong man to keep me safe right now.’ And the fastest way to hone in on the strong man in the room is…”
“To grab his penis?”
She giggled a bit as she realized how silly it sounded coming from a strong woman like herself. “Yeah, that’s about it. It was pure instinct. And that monkey brain was probably thinking ‘He’ll definitely protect you if you make his penis really happy.’” She gave it a few light strokes, and I moaned in pleasure.
“Well, it might be stupid, but I think it worked pretty well,” I said.
“Yeah? You’re always going to protect me?” Chloe asked in a low, sultry voice. She rolled over now to lay on top of me, lining my hard cock up with that pristine, tight pussy of hers. “Promise?”
“I promise.”
—
I had tried to avoid taking my girlfriend to my grandpa’s house for a while. I still couldn’t get the image of the sunblock incident out of my head, but I still knew she hadn’t intended to do anything unfaithful. Even so, visits with my siblings or parents were much less nerve-wracking than with the horny old bastard. When he suggested a movie night, it sounded innocent enough; at least he wouldn’t have a good excuse to be butt naked in front of my girl again.
Chloe was looking sexy as usual. She was wearing some denim shorts that had me tempted to give her ass a nice smack whenever I could get the chance. Couple that with all the cleavage from her crop top, and I was once again going through some breathing exercises so I wouldn’t get hard just walking up to my grandpa’s door.
This time we were greeted by a different sight than my horny grandpa.
As we were about to get to the door, it was already opening. Chloe and I found ourselves looking at a young woman who couldn’t be any older than 25. She had a cute, mousey face and glasses. That slightly dorky vibe she gave off went away quickly as I found my gaze dropping a bit. One look at the huge tits barely contained in her tiny tube top was all I needed to realize why she was there. I had never seen my grandpa with a girl who had anything less than DDs. Looking down a bit further, I was greeted with a tiny pair of booty shorts complete with a thong riding up a bit; she’d be sporting a whale tail right above those cheeks. In short, with that outfit and the heels and the thigh-highs, she looked like a bookworm who’d decided to try out prostitution.
The girl’s face suddenly went red in embarrassment, and she tried to pull her tube top a bit to cover more of her tits. It’s not like it wasn’t obvious what she had been doing; she still looked super disheveled. Hell, she even was missing one of her thigh-highs completely as she did her walk of shame.
“H-hello,” she managed to squeak out. “Sorry, I was just leaving.” She walked as fast as she could in her heels past us, pulling up her shorts a bit too to attempt to hide her ass crack.
Chloe and I just stared at her for a second as she left before turning to each other in disbelief.
“Oh my god,” Chloe broke the silence. “I think we just saw one of your grandpa’s fuckbuddies…”
I tried to keep calm as I processed that. ‘Fuckbuddies.’ My old ass grandpa had a gorgeous young fuckbuddy and had just finished fucking her silly before we had gotten there. That insecurity welled up inside me again.
“I swear, he’s like a horny old dog,” I said, shaking my head while we entered the house. “All he can think about is fucking.”
“Can you blame him?” Chloe asked. “Like, have you seen his balls? They’re so big and heavy that it has to hurt if he doesn’t get them emptied. I’m glad he’s still getting taken care of.” She didn’t elaborate more. She had just tossed out that casual observation and went on to chat about the movie night. Of course, I’d keep thinking about what she’d said all night as usual.
—
“What are we watching Lucas?” my grandpa asked as he met us in the living room and sat down. I had expected him to be in his own chair as usual for the movie, but he had decided to sit on the couch, still wearing just his underwear like usual, dong flopping. I was suddenly very aware of the fact that my girlfriend was in the middle sandwiched between us. My grandpa Jim looked over at my girlfriend, “This kid is a huge movie nerd. Well, he’s a nerd in general, but he’s had his eyes glued in front of a screen watching movies for as long as I can remember.”
“Oh believe me Mr. Tucker, I know,” Chloe said with a grin. “I love all the little rants he goes on about movie trivia. Like, it’s so cute I could listen for hours!”
“Right, so cute,” my grandpa said sarcastically, but she didn’t seem to notice. “And stop calling me Mr. Tucker, makes me feel old. Jim is just fine.”
“Grandpa, you’re literally closer to 100 than you are to 50,” I chuckled a bit. It felt great when I got the chance to poke fun at him instead. “I think Mr. Tucker is fitting.”
“Okay smartass,” he said, managing to scoot a bit closer to Chloe. “If you want, I can have her call me ‘Daddy’ instead.”
“Stop it you two!” Chloe said playfully, giving each of us a light swat on the arm. “You’re both so silly sometimes. And don’t worry Jim, you’re definitely not old. We saw how your… friend looked when we got here. I think men half your age would have a hard time keeping up with you!”
“You got that right,” my grandpa said smugly, and part of me wondered if he’d wanted us to see his latest fucktoy. “Hell, I’m three times older than her boyfriend, but he’s the one on cleanup duty tonight.”
Chloe’s eyes flicked over to Jim’s crotch, and I held my breath for a second thinking about what was in her head at that moment. For me, it was the crazy realization that his fat cock was probably still slick from stretching out a cheating pussy.
I coughed a bit and quickly changed the subject. “Ummm, I think I have a good movie to watch. It’s a bit scary, but I feel like it’ll fit the mood with the storm tonight. Have you ever watched Lights Out?”
—
Chloe had a lot of bravado when she said she could handle the movie, and I believed her. We hadn’t watched a horror movie together before, but I hadn’t seen her freak out from anything aside from the nightmare that one night, and that had happened a while ago. Lights Out was a movie about a shadow creature that could only move around in the darkness, so it was probably less spooky than a realistic phobia like spiders.
I was pretty wrong about that.
“Baby, are you sure you’re ok? We can watch another movie if you want,” I said, looking over at my girlfriend who had gone burrito mode in her blanket.
“N-no I’m fine. It’s not that scary!” Chloe said, her voice trembling a bit. She really was stubborn sometimes.
The movie was actually scarier than I remembered; I think it was partly due to my anxiety already being through the roof with my grandpa’s stupid cock just hanging there next to us. I wanted to wrap Chloe in my arm, but I was so on edge that I couldn’t stop slightly shaking. I was trying to calm down a bit so I didn’t seem like such a pussy in front of my grandpa.
A streak of lightning lit up around the house right before a major jumpscare in the movie, and that was enough to make Chloe and I both jump in our seats.
“That got me a bit, not gonna lie,” I chuckled, before looking over at my girlfriend. My breath faltered from what I saw. Chloe was clearly scared out of her mind from the last scene, but that wasn’t what had me starting to spiral. She had instinctively curled up against my grandpa, pushing up close with one arm wrapped around his chest, shivering while she cuddled up with him.
The tense scene wasn’t even over in the movie. The monster was still stalking the main character with eerie music in the background. Even though her face was buried in my grandpa’s chest, Chloe was clearly anticipating the next loud jumpscare.
When that jumpscare came, I wasn’t even looking at the screen. My eyes were fixed on my girlfriend as she acted instinctively. Her fear response was once again reaching out to the strong male in the room. Her hand slowly worked its way past my grandpa’s waistband, and I knew exactly what was happening when I saw her breathe out a sigh of relief. She had found it: the big fat penis of the most masculine man in the room, and she wasn’t letting go. I watched in horror as she started to stroke, nice smooth movements up and down his shaft as a reward for being her protector that night.
Chloe seemed to realize what she was doing all of the sudden, and she glanced over at me. I didn’t even know what to do. Was I supposed to call her out for getting spooked and giving my grandpa a handjob? How the fuck would that conversation even go? I decided to plant my eyes forward on the screen a bit, suddenly intently focused on the movie to avoid what was going on.
When I finally glanced back over at my adorable girlfriend, it was more of the same. She was being *thorough*. Her hand worked up and down his shaft, pausing for a few seconds now and then to give the glans some nice thorough stimulation. Her other hand slid down into his underwear as well, helping out with a comprehensive ball massage session. My grandpa groaned from the pleasure. He didn’t even bother to look over to check if I had noticed.
It was hard work milking a dick that big, but Chloe was persistent. From the looks of things, she was ignoring the movie completely by now, and her breath was quick and shallow. She was horny as fuck. The wet sounds of the handjob intensified as it was lubed up with the precum combined with the pussy juices from his earlier fuck session.
My grandpa finally groaned in pleasure once more as he erupted in his underwear. And it was a fucking eruption. Glob after glob of thick jizz squeezed out of his dick, filling up that underwear with his nasty nut sludge. Chloe’s full attention was on his crotch. She was gazing down in the darkness at his bulge as best he could, fascinated from the sheer amount of viscous liquid coming from that massive fuckstick.
My grandpa finally leaned back into the couch, one arm still around my girlfriend. He raised it up to rub her head as if rewarding her for what she’d just done.
I felt dizzy from all the mixed emotions in my head. A small part of me thought that seeing my girlfriend give a handjob like that was the hottest thing in the world, but everything else was spiraling out of control. Jealousy, anger, and anxiety all hit me like a truck while my girlfriend continued to give him a post-orgasm ball massage.
Just then, another huge streak of lightning blazed outside the window, and all the power in the house died.
“Oh god, I think I’m gonna pee my pants…” Chloe’s voice trembled.
“Calm down, it’s probably just a tripped breaker,” rumbled my grandpa’s voice. There was a faint bit of light through the window onto the couch, but it got much darker through the rest of the house. “There’s a panel right past the kitchen over there Lucas. Why don’t you go check it out?”
Part of me wanted to yell at him to check it out himself, to ask if he enjoyed getting his dick milked by my girlfriend. But another part of me was morbidly curious; she had already betrayed me so easily, so what would she do if I left the room?
“Fine,” I said, getting off the couch and walking off into the kitchen. I thought about turning my phone off but decided against it. I doubted anything else would happen if they knew I was still there watching.
I heard a shifting on the couch, but it was still too hard to see at first in the darkness. My eyes were still adjusting, and I struggled to figure out what the hell was happening between them. The sounds I started hearing were unmistakable.
You see, kissing was one of the things Chloe loved most. Out of all the possible positions and lewd acts we could do, a simple tongue to tongue makeout session often got her insanely horny. She’d even been close to cumming from just kissing from our prolonged cuddling, kissing.
That’s how I knew those tiny moans and sloppy lip sounds immediately. I knew exactly how passionately she was pressing her mouth into that fat bastard’s lips. She was snaking her tongue in with each smooch, working it all around with his desperately. I heard her cute “Nyom” as she wrangled his tongue between her lips, sucking on it like she was claiming it as her own.
My eyes finally adapted to the darkness. Chloe was straddling him with her juicy thighs pressing down on either side. Her crotch was flush against his, his underwear and her shorts the only barrier between them. My grandpa was letting her do all the work with the sloppy kiss session, but he wasn’t idle. His hands found their way to her ass, groping her through the tiny denim shorts. It was a tight fit, but he managed to start working the shorts down a bit. It was an amazing sight when he finally got the shorts past her cheeks; he punctuated his small victory with a nice smack on her cheeks with both palms, kneading her bubble butt and pulling her in tighter to violate her mouth with his own tongue.
I don’t know what sent her over the edge. Maybe it was the rough, dominant way Jim handled her. Maybe it was the taboo of the whole situation. Maybe she was just needy as hell and I hadn’t taken care of her enough sexually enough. Whatever the reason, this simple makeout session was enough to get her ass shaking as an orgasm pulsed through her body. It lasted for a bit before she finally slumped down onto my grandpa in bliss.
I was seething and horny at the same time, teeth clenched in rage while my dick throbbed in my shorts at the sight. It was all too much for me as my grandpa gave her another firm slap on each ass cheek. My little dick erupted into my underwear, shooting out my weak seed uselessly into the fabric while my grandpa had just gotten his milked out by a goddess. So much came out and flooded my underwear that it felt like I was pissing out cum.
That snapped me back to reality pretty quick, and apparently Chloe had come to her senses a bit as well. She pushed back on my grandpa’s chest a bit, looking him in the eyes before swinging her legs off his lap and getting back into her seat next to him. She looked down at his briefs in a panic, likely realizing how obvious it was that he’d blown a massive load of jizz in there.
Chloe started helping him remove his underwear, and I caught just a few words, asking him frantically where she could find a clean pair for him. The last thing I saw before heading off to the breaker box was her running off to his bedroom to find a clean pair for him.
I had to wait for a bit more after I’d reset the breaker. Luckily the room was still dark aside from the glow of the tv, so I was able to watch from the shadows a bit longer as Chloe pulled up the new set of underwear onto his junk. He reached down to pull her shorts down a bit and slap her ass again, but she reprimanded him quickly so as not to get caught. She pulled the denims back over her cheeks and sat down next to him, fixing her hair.
I was too drained from the orgasm and emotions to confront the two of them, so I sat down like nothing was wrong, and we finished the movie.
—
As we drove home in silence, I figured there wasn’t much of a point to even bringing this up to her. Chloe had just given a nice long handjob to my grandpa and then kissed him until she was creaming on his lap. It didn’t get much more straight-forward than that. I would just send her a text tomorrow telling her we were breaking up, and it’d be easy enough. It’s not like we were living together anyway.
“I fucked up,” Chloe said quietly. I looked over at her for a second but said nothing before glancing away. She looked over at me with tears in her eyes. “I fucked up bad tonight babe.”
I didn’t respond immediately. I just kept looking at the road. “Tell me how,” was all I said. She seemed to realize then that I knew exactly what she’d done.
“I-I haven’t been able to stop thinking about your grandpa these past few weeks,” she said, clutching at her thighs. “Like, all the time, that stupid cock has been in my head. It wouldn’t go away no matter how much I tried to distract myself.”
“And then tonight…I jerked him off. I didn’t even realize I was touching him at first, it was like an instinct. Then I got so fucking horny and couldn’t help myself. I jerked him off until he finished. I sat on his lap and kissed him when you left the room, and I even had an orgasm during it. I’m so fucking filthy…I’m so sorry babe. I really am”
If I could stand the sight of my girlfriend sobbing, maybe this would have all turned out differently.
I slowly exhaled and thought for a while before responding. I probably could’ve just told her to fuck off then and there, but I also could’ve stopped this at any number of points in the night. She had outright cheated on me, but she decided to tell me the truth of her own volition.
“Damnit,” I said. “You’re right, you really did fuck up baby…but I know what kind of person you are.”
Chloe perked up a bit.
“So if we’re going to stay together, I need you to promise me one thing. What you just did, sneaking around behind my back…I need to know you’ll never do that. Ever again. We’re going to be honest about everything.”
“Oh god Lucas, I promise!” She said, leaning over to give me a kiss on the cheek. “I’ll be honest. I’ll do whatever it takes to make up for it!” She kissed me again while rubbing my thigh. I gave her a little smile and kissed her back.
“Well now that we’re being honest,” I said sheepishly between the kisses. “We need to get back to my place fast.”
“Why’s that?”
“Because I need to fuck you so badly right now.”
—
We had a monumental marathon of makeup sex that night. I came in her mouth and on her tits and on her face and filled up condoms in her pussy until I could barely move. She was still that same loving golden retriever of a girlfriend that I loved, even if she had made a terrible mistake that night.
And honestly, she made up for it. She texted me all the time with updates on how she was feeling. She turned on her shared location to show me she wasn’t fucking around, even though I told her I had already started trusting her again. We didn’t bring this up with my grandpa because it really wasn’t worth the shitshow that would follow, and Chloe had made the first move anyway. She made it clear on subsequent visits to his house that flirting and being handsy with her weren’t tolerated, and he begrudgingly backed off.
We lived happily ever after.
—
Or rather, we might have lived happily ever after. The regret from that one bout of cheating was enough to bring back Chloe as the loyal, doting, perfect girlfriend. That much is true.
The thing is…Chloe isn’t the only girl in this story. She has a sassy, bold, slightly brooding best friend named Blair. The two of them should’ve been like yin and yang, but they blended together in a prime example of opposites attract.
And I was about to inadvertently introduce this gorgeous goth vixen to a pleasure that could tame even a spirited, rebellious girl like her.
—
(I like some emotional evisceration in my cucky/cheating stories. There’s going to be a lot more of it going forward.
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