(Hailey)
In hindsight, we should have known it was a bad idea. It’s almost laughable now to think this was going to end any other way. On the other hand, I guess it made sense at the time. My boyfriend and I were short on cash, so offering Damon a blowjob for a sack of weed didn’t seem like a terrible idea. After all, my boyfriend knew I had blown guys before, so one more wouldn’t really matter. Right?
I stopped by Damon’s after work, and he had no idea what I was about to propose. I thought that would be for the best, considering I almost backed out. I thought I could just use the tips I made at my waitress job to pay for the weed instead, but my shift was dead, and the little bit of money I did make wasn’t cash. So, it was back to plan A.
Damon opened the door to his apartment and looked me up and down. He usually did this anyway, whether my boyfriend was with me or not. I could tell it made my boyfriend Travis a little uncomfortable, but he never said anything about it. Of course, considering what was about to happen, a slight glance was the least of Travis’ worries.
I had on a white button-up top. The sleeves were rolled up to just below my elbow, and I undid an extra button on the way to Damon’s apartment, letting my tits help in my negotiations. I had on form fitting, black pants that hugged my ass tightly and I wore just enough make-up to look cute but casual. I smiled at Damon as he led me inside, and I could feel his eyes on my ass as he followed behind me.
“The usual order?” he asked casually.
“Yes!” I replied, turning around to give him a big smile. “Actually, I had a question.” I bit my lower lip, trying to look as innocent as possible. I opened my green eyes wide and let my blonde hair frame my cute face.
“What’s up?” he asked. I could tell my look worked. He was a big guy, 6’4” tall with dark skin, and his hair was cut short with slight waves on top. He had broad shoulders and thick, muscular arms. The more I looked at him, the more excited I got about blowing him.
“So, my boyfriend and I have been a little short on cash lately… I thought maybe I could find another way to pay you today,” I let the question hang in the air as I slowly walked towards him. I could tell he knew what I was implying but was unsure if I was serious. I let my hand graze across the crotch of his jeans, letting him know I meant every word. I looked up at him with my big, emerald eyes and slowly sank onto my knees. He smiled down at me and ran his strong hand through my hair.
I slid his pants down, revealing a thick, black cock bigger than my boyfriend’s, even though he was only halfway hard. I did a poor job hiding my shocked expression, and I heard Damon laugh. “I guess I’m a little bigger than your boyfriend,” he said. He was cocky now, and I couldn’t help but be drawn to him.
“Not just a little,” I said, stroking his ego just a bit before doing the same to his cock. I wrapped my lips around him. I always loved sucking Travis’ dick. I always seemed just the right size to swallow, and it didn’t take much effort. With Damon, my mouth felt full. His cock felt heavy on my tongue, and I struggled to take him in my mouth and gagged when his head hit the back of my throat.
“Good girl,” he said. “Not bad for your first try.” I could feel the mix of my spit and his precum on my chin. I smiled up at him, not bothering to wipe it off. I stroked him into my mouth, but I could feel my jaw already getting tired. Damon stood over me, just watching. Taking in the sight of someone else’s girlfriend sucking his cock like her life depended on it.
“Are you close?” I asked as the burning extended into my forearm.
He laughed again. “No way. I can never cum from a blow job.” I took the challenge and started stroking him fast, but only for a second before I had to take a break. I let go of his cock and shook my arm out while I lightly teased the head of his cock with my tongue. “It’s not gonna work, baby girl. And if I don’t nut, well, you don’t get your bag.”
I looked up at Damon helplessly. This time, I knew what he was implying but was unsure how to respond. First, Travis and I hadn’t discussed anything going further than giving him head, and I how no idea how he would feel about Damon fucking me. Secondly, Damon was fucking huge. I thought dicks like his were reserved for some porno set, not real life. As curious as I was about what it would feel like, I was also scared. I stared up at Damon, frozen with indecision. “Come on,” he said. He gently took my hand, guided me over to his couch, and turned me away from him.
He felt every part of my body as my heart thudded in my chest. Damon’s hand cupped my breasts, and a slight moan escaped my lips. His hands ventured south along my flat belly, and his thumbs dug into the waist of my pants as he pulled them down around my ankles. “Bend over,” he said. I was stuck in a trance of obedience and did like he told me. My elbows dug into the cushions of his couch as I held myself up. He ran his hands across my smooth ass and gave it a smack. Another moan escaped. He parted my ass cheeks as he inspected both of my holes.
Thankfully, Damon started rubbing my clit, and I felt the flick of his tongue on my pussy. My gasp turned into a deep, erotic moan. He had me, and he knew it. Damon shifted behind me, and I felt the swollen head of his monster cock press again my wet slit. I felt my body grow tense, and he ran a hand gently along my back. “If you don’t relax, it’s going to hurt more baby girl.” His voice was soothing, and I took a deep breath as he pushed inside me.
My nails dug into the couch as my pussy stretched to accommodate his massive girth. I felt like I couldn’t breathe. My body started to shake violently. I couldn’t believe it. How on earth was I cumming already? I screamed with a mixture of pain and pleasure as my orgasm shot through me, curling my toes and rendering me breathless. His rhythm was perfect as he used my dripping cunt to milk his cock. I felt helpless, like my body was no longer my own. “You like that baby girl?” he asked. I wanted to say, “Yes.” No. I wanted to scream, “YES!” But all I was able to manage was tiny whimpers.
“Fuck girl, you’re so tight. Does your boyfriend even fuck you?” Damon asked. His arrogance was enough to send another shiver down my spine. He grabbed a fist full of my hair and pulled. “Come here, baby.” He pulled me off the couch and put me back on my knees. “Open your mouth.” I obeyed. I looked up at him with my big, innocent eyes and opened my mouth just as his thick cum erupted from his cock. Only a bit landed on my tongue. I could feel the rest as warm, wet streaks across my face. “A deal’s a deal,” Damon said as he pulled up his jeans and handed me the bag of weed. “You can clean up in the bathroom, baby. Oh, and tell your boyfriend I will take this deal anytime.”
Source: reddit.com/r/eroticliterature/comments/tjilny/fm_cuckolding_the_bargain_chapter_1