This story is a continuation of My Girlfriend Asks Me to Suck a Cock. If you don’t want to read it, here’s the summary:
Free cuckold community
Sign up now!
The main character’s girlfriend wanted to see him give a blowjob to another man in exchange for anal sex. The main character reluctantly agrees, and the couple meets with Julius, an old friend of Carly’s. the main character finds the experience more arousing than he had imagined, even as Julius and Carly had kissed above him.
This story has cuckoldry, straight-to-gay themes, humiliation, bisexuality, and more.
————
“Be gentle, baby,” Carly said while looking up at me. She stuck out her lip in a cartoonish way.
I rolled my eyes and smirked. “You’ll be fine.”
“You asshole,” Carly said, shifting down on the bed and raising her hips. We were laying down in missionary. Both my cock and her asshole were lubricated, and as they touched, I began to feel anticipatory chills travel through my body.
For years, I had wondered what it would be like to try anal, and today, I was finally going to learn.
Carly closed her eyes to focus as she relaxed her muscles, letting the head of my dick push past her entrance. She winced, but I could see a shine of arousal on her pussy.
God, she was tight.
Her pink, puffy nipples were swollen on her freckled chest, and her massive red hair made a fiery halo around her flushed face.
I moaned, feeling my cock pulse with precum.
Carly stayed like that for a moment, breathing deep as she let her ass take shape around my member.
My cock was just below average size at five inches, and it wasn’t too long before she began guiding my hips, letting me slip deeper into her.
I groaned again, trying my best not to cum. I was only a few inches in her, and I was already on edge.
Then, unexpectedly, Carly spoke. “Did you like sucking Julius’ cock yesterday, baby?”
What? What did that have to do with this?
Carly guided me deeper, flexing her ass so it squeezed my shaft.
I shivered. “Um,” I said, “yeah, I guess.”
“I'm just trying to turn myself on, baby,” she said, sticking out her lower lip again. “I’m sorry.“
“No,” I said. “It’s fine.“
Carly sighed as she pushed her hips farther up, taking my cock to its base.
I gasped as Carly whined.
“You looked so good with that big dick in your mouth, hon,” she said. She moved her hands from my hips, grabbing the bottle of lubricant from the nightstand with one hand and moving the other to her pussy.
Immediately, I could hear how wet she was.
She uncapped the lube and let a stream of it flow between us. It landed on my cock as I slid out of her. It was cold on my skin.
“Hearing you gag and choke on him had me absolutely gushing,“ Carly moaned, letting her fingers slide over her clit.
I shifted uncomfortably, distracted from the pleasure of having Carly wrapped around my cock.
“You don’t have to pretend you didn’t like it, baby. I saw that little erection of yours,“ she heard.
Little? I screwed up my face at Carly. She knew I was sensitive about my size.
“I’m just teasing, babe,” she said, beginning to bounce on me, “but you know you fucking liked it.”
It was true, in spite of my awkwardness surrounding the situation, I couldn’t deny that it made me incredibly hard at the time. I had done my best to avoid thinking about it until now. Just the thought of his cock in my mouth sent a rush through me.
“Keep fucking my asshole,“ Carly said.
I hadn’t even realized that I had stopped. I started again, and with all the new lubricant Carly had applied, I was now able to easily work my dick in and out of her.
Carly bit her lip. ”Fuck my ass like that baby,” she said, looking up with her big green eyes, “be a good boy and fuck my ass.“
My muscles shook, and I let out a low, even groan. Her insides were so hot, and watching her begin to slide her fingers in and out of her cunt as I filled her ass was becoming too much.
I closed my eyes.
That was when I felt Carly‘s other hand.
As she had been applying lube, she let some fall onto her fingers, and when I’d been fucking her ass, she had been spreading it along her fingers, evenly applying lubricant along their surface.
I opened my eyes right as her fingers touched the curve of my ass, and I made eye contact with her as she slipped the tip of her finger past my cheeks and into me.
I’m ashamed to say that I moaned again.
This wasn’t the first time that Carly had put a finger inside of me, so I didn’t think too much of it. There were times when she had sucked my cock with a finger in my anus, massaging my prostate as she choked on my dick.
It always felt good, but now it seemed different.
Previously, when she had fingered my ass, she had kept her progress slow and steady, moving with the rhythm of her mouth.
Now, while she wasn’t exactly ramming her fingers into me, her pressure was even and relentless. As I parted my lips and stared into her hungry gaze, she easily slipped a full finger into my asshole as I fucked hers.
“I loved seeing you with Julius, my sweet boy,“ Carly said. Her voice was sultry and breathy. “Watching him pump his load into your throat was the hottest thing I’ve ever seen.“
I opened my mouth to protest, but I couldn’t catch my breath. Carly’s exploring finger had become my whole world.
“If you wanna cum in my ass,” Carly said as she began to finger fuck me in earnest, “I want you to agree to see him again.“
What? What was she on? I had told her it was just once.
I shook my head.
She raised an eyebrow, and she stopped moving her hips and hand. A moment ago, it had felt like my very soul was being turned inside out, and now she stopped every sensation. She wrapped her legs around me so I was completely buried in her. I couldn’t move in or out.
“Don’t stop,” I gasped.
“Say you’ll see him again,” she said, once again, pouting. This time, the innocent bratty move had much deeper implications.
I broke, giving a half nod.
That was enough for Carly. She didn’t start to move her hips again, but she began to piston her lubricated finger in and out of my ass, making sure to angle toward my prostate.
I didn’t even have time to thrust; just her finger was too much. Without another movement, I came into Carly’s ass as she fingered me.
The next night, she invited Julius over.
I was pacing back-and-forth in our kitchen.
“I just don’t know,” I said. “I just don’t know.“
Carly sat at the counter, lackadaisically dragging a pen over a Post-it note. “He’s already on his way over,“ she said. “ If you want to send him home once he’s here, that’s okay, but there’s no point in calling if he’s only a few minutes out.“
I pursed my lips and stopped. “Have you ever fucked him before, Carly? Be honest with me.“
It was strange to call her that. When you’re with somebody for a long enough time, you stop addressing them by their name. It made the sentence sound unfamiliar and clinical.
Carly stopped moving the pen and stared up at me. Her brow was furrowed, and she spoke dispassionately and frustratedly. “If I had already fucked Julius,“ she said, “I would’ve told you. You know that.”
I clenched and unclenched my fist. Now I was accusing her? This wasn’t like me.“Just…“ I said, “you kissed him.“
“And you blew him until he came down your tight throat,“ she said, standing. “I think we all got a little lost in the goddamn moment.“
“That was… That was just because you wanted me to,“ I said.
Her expression softened.
Carly sauntered around the counter, swaying her hips with each word. “And. You. Would. Do. Anything. I. Wanted?”
With her final word, she now stood only inches from me. I could smell her flowery perfume as I looked down at her. She was a full head shorter than me, but I still felt like the small one.
I opened my mouth to respond, but I couldn’t find the words. What was I supposed to say? No? I would do anything for Carly. It was only now for the first time in our relationship that I felt any level of insecurity.
She raised a hand and put it on my chest. It was a still presence against my fast beating heart.
“I have never fucked Julius,” she said. “The other night was the first time I’ve ever seen his cock, and it was just as much a surprise to me as it was to you when I saw it. You are the man I love, and I find you amazingly sexy.“
My racing thoughts started to slow at her words. Carly always knew how to soothe me, take care of me. I closed my eyes and breathed out, and I felt her other hand touch my waist.
“However,“ Carly said in the same calm tone, “now that I know what he’s got, part of me regrets never taking him for a ride.” She gave me a wry smile.
I smiled back at her, trying to push down the frog in my throat. “You fucking jerk,” I said.
“And furthermore,“ she continued,“now that I know what he’s got, I want to see you take him for a ride.“
Carly must’ve seen my eyes grow wide, even as I try to remain stoic.
“Don’t act so surprised, baby,“ she said, “you know I always fantasize about you with another man.” As she said this, she trailed her hand from my waist to my cock.
I shuddered. In spite of all my misgivings, panic, and fears, I was as hard as a rock. I hated to admit it, but I couldn’t stop thinking about the other night, and even the thought of Carly and him kissing had me whirling. She had just melted into him. Had I ever made her do that?
Why did it feel like electricity sparking over my skin?
“I’m not going to make you do anything you don’t wanna do,“ Carly said, dragging her fingers over my hard shaft. “It’s just… You know how hot I think it would be to watch you take his cock into that pale little bubble butt of yours.” She giggled, moving her other hand from my chest to my ass.
I was a devoted gym goer, and my squats had paid off. Carly frequently teased me about my “bubble butt.” I felt my cheeks bounce as Carly shook my ass.
She wouldn’t make me do anything I didn’t want to do, and I didn’t want to do anything. Julius was coming over, and all I would have to do is tell him that nothing was going to happen. It was as easy as that.
The doorbell rang.
Carly smiled, stood on her tiptoes to give me a kiss, and she was off like a bolt, her mess of red hair bouncing as she nearly skipped.
I followed, feeling somewhat numb.
I stepped around the corner just as Julius was walking in. He wore a fitted T-shirt, and I saw his muscles ripple as he reached out to hug Carly.
She practically jumped into his tattooed arms, and as he embraced her, I saw her toes lift a couple inches off the ground for a moment.
Why is it that the most indescribable things can mean so much? As he lifted her, another shockwave of confusing jealousy bolted through my body, and the image of her sitting next to him, fingerfucking herself with his arm around her, entered my mind again. My mind buzzed, and more hypothetical images flooded my brain. What would she look like with his massive cock inside of her? What would it feel like to watch him hold Carly in the air, her feet completely off the ground as he fucked her?
My perverse, envious bubble popped as I saw Julius turn to me and lean in for a hug. His strong hands drew me closer, wrapping around my back and shoulders as he pressed his body full force into mine.
Oh, God. My cock was still erect, and it grinded into his upper thigh as he pulled me close.
Julius didn’t react physically at first, he just held me, hugging me tight. His muscles felt hard as steel against my body. I hugged him back. His musky cologne filled my lungs again, and sharp memories of his dick plunging in and out on my lips pricked at my brain.
As he drew back, I filled my lungs with air again. I hadn’t realized how hard he had been holding me.
He flashed me a smile and looked down at my crotch. “I’m happy to see you too, babe,“ he said.
My cheeks grew pink. I cleared my throat.
This was the moment. I had to let him know now that although Carly and I had enjoyed our time together, he had to leave now.
I opened my mouth. “Do you want anything to drink?“ I heard myself ask.
Julius tilted head back-and-forth, considering.
God damn it. I guess he was coming in.
”Y’all got any wine?“ He asked.
“You still like Malbec?“ Carly asked, stepping closer to us. Julius and I were only about a foot apart. I could smell a subtle hint of mint on his breath as he chuckled. I stared at his lips. Only days ago, they had met Carly’s, and now, as he towered above her, I wondered if that would happen again.
No. Of course it wouldn’t. I would get him a glass of wine, and then he would leave, a stranger once again.
“You know I do, Car,” Julius said, smiling.
Wait. We had Malbec? Had she bought a bottle just for him? I couldn’t remember if we had already had some wine before she went out for groceries the day before.
Again, envy vibrated through my body.
Still, I couldn’t stop looking at her next to him, so fragile and small comparatively. His hands looked like catchers mitts compared to hers.
“Let’s pour a few glasses then,” I said, my ears burning.
We moved to the living room, and I grabbed us three glasses of wine, filling mine nearly to the brim before draining it and pouring another. It was a slightly chilled red wine full of tannins. My tongue caught on the roof of my mouth as I gulped back the bitter, dry liquid.
I felt like I’m going crazy. I feel like I’m losing my mind.
All the while, I can’t stop thinking about how Julius’ cologne smells and how his hand felt gripping my head, stroking his cock with my lips.
I shook my head. I had to keep it together. I trusted that Carly didn’t and wouldn’t do anything I wasn’t comfortable with, and I know that she would never push me to do anything that I truly didn’t want to do. The fact of the matter was that I wasn’t even sure what I wanted. Even as the possibilities raced through my mind, it was like they moved too fast for me to touch them.
I took Carly and Julius‘ glasses first, bringing them to the coffee table and setting them down, getting a “thanks“ from each of them. After grabbing my own, I returned. Carly and Julius sat on the couch in the same spots they had been in the other night. Last time he sat there, Julius had been a stranger.
Now, as I settled into an armchair, he was familiar at the very least. I might still not have known his last name, but I knew what his seed tasted like.
“So did you get your prize?“ Julius asked, leaning forward and taking his glass.
“What?“ I asked.
“Your prize,“ Carly said, laughing. “You know, getting to fuck my little butt.“
“Oh, that,“ I said, laughing along. “Yeah. I did.“
“Was it everything you ever imagined?“ Julius asked.
I considered that. What was I supposed to say? That it all ended with Carly finger fucking me until I came? “And more,” I said. ”It was great.“
Carly smiled at me. “Yeah it was.“
God, she could be a brat.
“Anal is crazy,” Julius said. “I scare most girls off from taking me in the ass, but it’s the guys that are all for it.“
The sudden thought flashed into my mind of Julius fucking me, but I pushed that thought out of my mind. I’d sucked his cock, sure, but I wasn’t gay.
“More guys are size queens than girls,” Julius said, sipping his wine.
“Then you just haven’t met the right girls,“ Carly said, taking her own glass.
“No, I’m serious,” Julius said. He was responding to Carly, but his eyes were trained on mine. I couldn’t bring myself to look away from him. “I fucked plenty of guys and plenty of girls, and it’s almost always the guys will become addicted to a big dick like this.”
As if to make his point, Julius reached down with his free hand and grabbed his cock through his sweatpants. They were made of a thick fabric, but as he wrapped his fingers around it, I could see it’s whole shape. He wasn’t fully erect, but just looking at his girth took my breath away again.
Shamefully, I looked up at Carly. She was staring, lips parted at Julius‘s dick, just as I had been only moments ago.
“So you‘ve probably gotten pretty good at dicking them down?“ Carly asked breathlessly. “They keep crawling back for more?”
Carly‘s obsession with gay sex was palpable. While I still wondered if there was a part of her that wanted that cock for herself, I knew that at the moment she was imagining Julius fucking other men. She was probably thinking about him fucking… me.
“I… I think I’ve heard that about gay guys before,“ I said, trying to distance the situation from now
“Not guys who’re gay,“ Julius laughed. His hand was still wrapped around his cock, and he squeezed it, causing it to swell in response. “I can’t tell you how many ’straight’ men have called me up at two in the morning to get a piece of this.“
I took another gulp of wine and swallowed, averting my eyes. I could hear Carly breathing heavily, and my own chest rose and fell quickly. “Anyway, Julius,” I said. “Carly and I talked, and we wanted to thank you for coming over, but…“
“So straight guys too?” Carly asked Julius. It was as if she hadn’t even heard me.
Julius shrugged. “Sure,“ he said. He let go of his cock, adjusting his sweatpants once again hide its silhouette. “I’m not in the business of labeling someone else’s sexuality.“
“Carly,” I said.
She finally pulled her eyes away from Julius and looked at me. An apologetic look flash across her face. “Sorry,” she said.
Julius looked back-and-forth between us. “Hey,“ he said, “I hope I’m not getting between you two.“
“No, you’re not,” I sighed. “Sorry. I guess I’m just a little…“
“Tense?“ Julius finished.
I nodded. “Yeah, that works.“
”This is a weird question,“ Julius said, “but do you want a massage? I’m studying physical therapy, and I ended up getting my certificate so I can work on other athletes. I’ve gone pretty damn good with my hands.“
“I think I’m set,“ I said, smiling and shaking my head.
Julius stood, his full size once again becoming apparent as he loomed over me. “If you only think you’re good,“ he said, “you ain’t good. Lay down for me on the floor. I promise I won’t bite.“
I felt my cheeks redden. “Thanks, but—“
”Seriously,“ Julius said. “I got you. I’m a professional. You don’t even have to take your clothes off or anything like that.“
“It’s alright if you want to,“ Carly said. “I think you could use a little relaxation.”
I should’ve said no. I should’ve shown him to the door.
Instead, after a long pause, I put my wine glass down with a shaky hand. My curiosity got the better of me. “Fine,” I said. “Just a little.” I let myself slide off of the armchair into the floor. My body was loose from the alcohol, And although I hated to admit it, as soon as my knees hit the floor, I turned and looked at Julius’ crotch.
I lingered like that for a fraction of a second, my face level with his dick. Then I turned in, lay my body flat on the carpet face down.
The plush fibers brushed against my arms as I adjusted, moving into what I thought would be an ideal position to receive a massage.
The floor moved slightly as Julius took a step, putting one leg on either side of my body.
He brought himself to the ground, positioning himself with his knees on either side of my hips. I could feel the heat of his skin.
This was supposed to be helping me relax, but I had never felt so wound up in my life.
He touched my lower back first, gently dragging his thumbs on each side of my spine.
I tingled with expectation. His thumb had only, barely brushed me, testing the tightness and suppleness of my muscle, and I was already anticipating what it would be like to have him ring me out like a towel.
As his strong hands continued to travel up my back, Julius began to apply even force, distributing his weight across every square inch of his fingers in palms.
I felt my muscles roll and give under his palm, and I could feel knots untangling themselves as he worked with skill and precision.
I didn’t know much about him, but based on the techniques he was using and the care was taking, he certainly wasn’t lying about having trained in this.
All the while, I was acutely aware of Julius‘ crotch resting against my ass. He wasn’t moving, pushing into me, or doing a single thing to suggest he was seeking something more, but I couldn’t help but think how few layers of cloth were between him and me.
He moved his way up to my shoulders, and was kneading out some tension in my neck.
I released a heavy breath. I had really needed this. The past few days, my mind and body had been coiled up like a spring, and as Julius kept massaging me, he was able to reshape each part that was out of place.
I turned my head toward Carly.
She was sitting on the couch, watching intently, her thighs squeezed tightly together.
This had to be turning her on. I knew that she had imagined me being fucked by another man an uncountable amount of times, and now she was watching as Julius straddled me and explored my body with his hands.
Was this all that wrong? My insecurities and fears still were present in full force, but was that fair to Carly? Fair to me? If I enjoyed something and Carly did too, was there really harm in it? Julius had even said that it wouldn’t define someone’s sexuality. Who was I to say that anything I did with him made me gay?
Julius’ skilled hands continued on my neck, gripping it tightly as I breathed deeply.
I decided to go for a Hail Mary.
I closed my eyes and reached behind my back, let my fingers travel up Julius‘s leg, and I rested my hand against his muscular thigh.
It was almost like I was having an out of body experience, watching myself gently rubbing the inside of another man’s leg.
“Tap twice if you want me to stop,“ Julius said. He shifted so he was just behind my ass, and he moved his massive hands down to my lower back once again, using force in small circles to dive deeper into my muscle.
I tried to give a groan of approval, but even to me, it sounded like a moan.
“He talks,“ Julius chuckled.
Carly was still pressing her thighs together, but now she was shifting back-and-forth as if she was sitting on hot coals. Her freckled cheeks were red, and even though she was trying to hide it, I saw that she was chewing the inside of her lip.
Julius continued, working down my spine until he was massaging the musculature around my tailbone.
Getting a massage didn’t mean I was gay or anything. Men got massages from other men every day. This was nothing.
Then his strong hands moved even further down, each finding an ass cheek.
I should’ve spoke up. There were so many windows to say something. Instead, I only managed a whimper.
It was such a quiet, pitiful sound, and I felt my cheeks burn in embarrassment as I heard myself. Still, I didn’t tap his leg.
He began to massage the outside of my clothed glutes, slowly but surely kneading each muscle until it gave.
I had to admit, it felt amazing.
Then I felt Julius shift. He had been resting back, but now he rose fully onto his knees. The spot where he had been partially resting on my thighs felt cold without him.
I was still touching the inside of his leg, and I felt fabric shift. Even though I couldn’t see what was going on, a chill traveled through me
Then Julius returned to his original position. Only now, I felt the full weight of his meaty cock resting between my sweatpants-clad ass.
My face started to tingle. I didn’t want to admit it, but this wasn’t as much of a surprise as it could have been. As soon as Julius had put his hands on my body, I had intrinsically felt this was a possibility.
I opened my eyes. My vision was blurry and unfocused, but I looked up at Carly again. Her legs were no longer pressed together, and while she was stabilizing herself with one hand, the other had disappeared down the front of her waistband. She was grinding her hips up and down as she slowly masturbated. Her eyes fluttered as they met mine.
(Continued tomorrow!)
Leave a Reply
You must be logged in to post a comment.