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How did you become a cuckold? And how do you feel about it?
Cuckolded Over a Game of Truth or Dare
“I have always been intimidated by my roommate, Rob. He was everything I wasn’t. Strong, masculine, domineering… all traits of a real man. Whenever we stood next to each other, Rob made me look small and weak in comparison. Where as I had only been intimate with a few women in my life, Rob was a complete ladies man. He regularly brought home women from clubs. It would be strange to come home from work and not see clothes strewn about the house…
Rob had a knack for making me do whatever he told me to. I regularly cleaned his dishes, did his laundry and even made him food when he asked. Part of the reason I did this was to avoid conflict, but part of me also knew he could easily overpower me if we ever had a disagreement. Rob would often “play fight” with me, easily putting me in sleeper holds or pie facing me to the ground. He loved to do this whenever I had company, usually getting a laugh from my friends and even my girlfriend, Sarah.
Sarah was the love of my life. She was completely out of my league, something my guys friends, and Rob, often pointed out. She was petite and slender, with straight, black hair, perky tits and an ass that always caught my friends’ attention. They would regularly talk about “hitting that” if we ever broke up. Rob was the most vocal about this.
Of all my friends, Sarah seemed to be closest with Rob. Whenever she came to visit, she would often spend hours talking to him, sometimes flat out ignoring me. She usually came off as flirtatious, rubbing his large biceps and caressing his strong pecks. I never took this personally. I knew a girl as a hot as Sarah would be used to the attention of other men. I figured she was just being friendly with him.
Things changed between me and Sarah after one fateful night. We had just spent the night having dinner with close friends. Rob and his latest fling, Megan, were both there, as well as my friend Sam and his girl, Laryssa. Sarah spent a good portion of the night getting to know Megan and the two seemed to click, seemingly sharing a lot in common. There were many times through out the night where they would whisper to each other and laugh. At one point Megan whispered something to Sarah that caused her to blush. Sarah seemed shocked by whatever it was Megan had told her. She looked at Megan, wide eyed and said, “There’s no way it’s that big!”, before sharing a quick glance with Rob who had a confident smirk on his face. It was as if the three of them were in on something that I was oblivious to.
After dinner, Sarah and I returned to our home with Rob and Megan. The two of them beelined to Rob’s room the second they walked in through the front door. Sarah and I both knew what was about to happen without saying a word to each other.
Sarah and I were getting ready for bed, which was difficult with the constant noise of bed springs creaking and Megan’s loud moaning. Sarah didn’t seem to mind though. At times it even seemed like she was even listening in on them.
We were both laying in bed when Sarah turned to me and whispered something that made my heart drop.
“Is it true that Rob has a big dick? Megan told me at dinner that it was at least 10 inches.”
“ I don’t know,” I responded meekly.
This was a lie as Rob was never shy about his body, even when it was just the two of us around the house. He often walked around with just boxers and a wife beater. the outline of his cock was very noticeable whenever he did so. I also frequently found used extra large condoms whenever I picked up after him. I always felt emasculated whenever I picked one up, knowing it was at least twice the size of mine. Strangely, I always got turned on imagining one of Robs frequent flings worshipping his huge cock.
“It’s no wonder Megan is moaning so loud. I would be too if I was was her,” she said slowly caressing her thighs. With that, Sarah turned around and turned off the bed side lamp. I’m glad she did, as my dick was getting painfully hard at the idea of Sarah riding Rob, screaming his name like Megan was on the other side of the wall. I discreetly started rubbing my dick once I was sure Sarah was asleep, getting more and more turned on listening to Megan shamelessly shouting profanities that even the neighbors could likely hear. I came with just a few strokes as I pictured Rob shooting a huge cum shot over Sarah’s face.
About a week later, I invited Sam and Laryssa to have drinks at our house with me and Sarah. Rob and Megan were both there as well, which surprised me since Rob rarely stayed with the same woman for more than a few days. I couldn’t blame him. Megan was a bombshell, almost as hot as Sarah was.
We were only a few drinks in when Megan asked us if we wanted to play Truth or Dare. I was a little surprised, having not played since high school. She said it would be a fun way to really get to know each other. Sarah seemed especially eager to play.
The game started off relatively tame, asking each other the usual questions to embarrass each other. At one point Rob turned to Sarah, asking her the titular question, to which she answered “Truth”. Rob looked at her smirking and said, “is it true your boyfriend has a small dick?” getting a quick laugh out of Sam and a look of bemusement from Megan and Laryssa. “It’s… normal sized,” she said embarrassed, turning to look at the ground. I was angry, but decided not to make a scene and ruin an otherwise fun evening.
Megan then asked Rob, who answered “Dare” confidently. She gave him a sultry look and said, “I dare you to take your shirt off”. Sarah’s eyes beamed as she looked away from the floor, her gaze now focused intently on him. Rob smiled and took his shirt off without hesitation, showing off his ripped, linebacker sized body. This earned a “Whoo!” from Megan and Laryssa, and all three women seemed a little too transfixed on him.
When it came back to Sarah, I could see she was still staring at Rob. She bit her lip and said, “I dare you to take off your pants,” not even bothering to ask if he wanted Truth or Dare. I looked at her in disbelief, and saw her jaw drop. Looking over to see what gave her that look of awe, I saw Rob drop his pants. Apparently, Rob had gone commando this evening as his massive cock slid out from his waist line. Even flaccid, Rob was bigger than me at full size. All three girls were stunned at his size, and Sarah in particular seemed enraptured by it.
Rob sat back down, keeping his pants off for the remainder of the game, making both me and Sam uncomfortable. While Sam and I both tried to ignore Rob’s nudity, it didn’t seem bother the other three women. When it got back to Rob, he looked at Sarah, who was trying, unsuccessfully, not to stare at him and his huge cock. He smirked and asked her, “Truth or dare?” She chose truth, wanting to take the safe choice while she was still totally abashed.
“What do you think of my dick?” he asked as the room grew silent. She looked at him blushing, very apparently flustered. “It looks… big. Like it would feel amazing to ride…”. She said this, biting her lip once again, running her hand on the top of her leg.
Sam and Laryssa looked at each other, eyes wide at what my girlfriend had just said to my bully/roommate. I was just as stunned as they were. I expected Megan to give her a look of jealousy, but she simply smiled with no traces of surprise on her face. I cleared my throat, awkwardly trying break the tension.
After a few minutes, Sam stood up helping the wobbly, clearly intoxicated Laryssa to her feet. They said their goodbyes before he walked her out the door with an unusually fast pace. Megan stood up as well. “I need to go too. I have work tomorrow and need time to recover”. She gave Rob a kiss on the cheek, caressing his still exposed chest. “This was fun, let’s do it again sometime”, she said, giving Sarah and me a knowing smile.
After they left, Rob grabbed his clothes, and said, “Goodnight, small dick!” laughing, as he walked to his room. Just as he was about to turn into the hall he looked back at Sarah and smiled. Her legs seemed to wobble as she let out a soft but unmistakable sigh of arousal.
My head was rushing the remainder of the night. I was embarrassed, angry and ashamed; all feelings betrayed by my raging hard cock. I thought about trying to get intimate with Sarah, but she seemed uninterested. Clearly she had something else on her mind. We both went to bed with lingering sexual frustration.
I awoke in the middle of the night feeling the bed shift. I looked over at Sarah who had just wrapped a satin robe over her otherwise nude, tight body. She didn’t seem to notice I was awake as she walked out the door and down the hall. I got up and followed quietly. My heart was beating fast, knowing, yet trying to deny, where she was headed. She quietly made her way down the hall, the outline of her hot, round ass visible from outside her satin robe. She walked up to Rob’s door and silently opened it.
I crept down the hall and peered through the crack of Rob’s slightly ajar door. Sarah softly nudged Rob. He turned around, confused at first, but then gave her his trademark smirk when he saw my mostly nude girlfriend standing over him. “Shouldn’t you be in bed with small dick?” he stared up at her, taking in her hot body.
“I couldn’t stop thinking about you,” she responded. “I wanted to show you how I really felt about your cock.” As she said that, she loosened the sash of her robe. The robe fell to the floor, sliding down her beautiful, round ass, as it revealed her slender, nude body. I gasped silently, trying to ignore the growing erection in my underwear.
Rob pulled his covers off, revealing his already growing cock. Both Sarah and I stared in awe at his massively hung dick. Sarah knelt down beside his bed grabbing it as it grew in her hand. The two of them looked at each other, their faces inches apart as Rob grabbed the back of head and pulled her in for a kiss. The two of them made out in front of me as Sarah began to stroke Rob’s hardening cock.
After they broke the kiss, Sarah climbed on to his bed, straddling Rob as she kissed from his chest down to his waist. Her head eventually made it down to his now erect cock. She basked in his scent, as she began to sensual rub the tip of his cock with her tongue. I noticed she was avoiding taking it in her mouth, likely because she was worried it wouldn’t fit.
My dick was throbbing at this point, precrum soaking my underwear as it bounced uncontrollably. I should have put a stop to this then and there, but I was stuck like a deer in head lights. I was partly scared that Rob might kick my ass in front of Sarah if I did anything, but it began to sink in that the real reason I didn’t stop this betrayal was because I didn’t want it to stop.
“Don’t be shy,” Rob whispered, grabbing the back of Sarah’s head with his big meaty hand. He thrust his pelvis up, his dick now lodged in Sarah’s open mouth. She tried to recoil in surprise, gagging on his dick as it reached far into her throat. She almost pulled back for air, but began to slowly bob up and down, matching the thrusting of his hips. She seemed determined to take his entire dick in her mouth as she began grinding her pussy on his leg uncontrollably.
As she continued to deep throat him, I noticed my hand instinctually rubbing my dick from outside my boxers. I felt an orgasm build after only a few strokes as I came inside my underwear. That was the hardest I’d ever cum and I wasn’t even having sex! My cock should have went flaccid, but it gained new life as I saw Sarah take his dick out of her mouth and slowly guided it to her pussy. Part of me knew that she would have done this even if she knew I was watching.
His cock slowly slid in her wet pussy as she rode him cowgirl style. She gasped, almost in pain from his girth, but when I saw the look of ecstasy on her face, I knew it was really pleasure that was washing over her.
“So big..” she whispered between moans. She could barely move on her own as Rob took control, thrusting up, slowly at first. Once she grew accustomed to his size, she began to take control, her ass bouncing on his legs as his cock slid in and out of her rhythmically.
“Oh Rob!” She said, almost shouting at this point.
“You like that? I bet small dick doesn’t give it to you this good,” he said grabbing her thighs as he propped her up and began slamming his pelvis into hers. She moaned loudly, “he doesn’t!”
I was hurt by her words, but the feeling of betrayal quickly vanished as I continued stroking my now exposed dick, unconsciously matching their pace.
Sarah alternated between humping my roommate to grinding on his cock. She bent down, running her fingers through his hair and kissed him passionately. She only broke the kiss to moan as he began to thrust hard and rapidly, causing her to shriek in ecstasy.
“You hear that small dick? I fuck your girl better than you!” He said laughing.
I gasped. Shit, shit, shit! How did he know I was there?
“Don’t be sad, dude. keep stroking it while I fuck your girl.”
Sarah slid off his cock and looked to the door with wide eyes. “Oh my god…” she said as we both looked at each other. “Nah keep going baby, your boyfriend loves this, don’t you small dick?” I didn’t respond. Sarah was stunned as if she was coming to from some inescapable trance. Rob didn’t hesitate as he began rubbing the tip of his dick on Sarah’s clit, making her moan.
She took my silence as tacit consent, as she guided his dick back inside her wet pussy. She gave the largest O face I’d ever seen. “oh fuck!” She moaned loudly, ignoring my presence.
Rob continued his pace from earlier, each thrust causing her to shake wildly.
“Has small dick ever given it you this good?” he asked her between breaths. “No!” she screamed as she kept riding him. “Whose girl are you now?” he said smiling. “Yours! I’ve wanted this for so long…” she said, grinding on his cock.
I had another uncontrollable orgasm as my roommate effectively made my girl his. The cacophony of moans from Sarah and laughter from Rob caused me to shoot ropes of cum on Rob’s door. I could tell Sarah was close to cumming as well once her hips started bucking wildly.
“Oh fuck, I’m cumming!” She yelled loud enough for my neighbors to hear. “Yeah, let’s cum together baby. Show small dick how it’s done…” Rob groaned. Sarah began convulsing on his body, her hands pressed against his chest as she tried to keep from herself from collapsing on him. Rob grunted, as he gave a few hard thrusts that almost sent Sarah flying into the head board. He came inside my his girl as the two of them grinded slowly on each other
He pulled his impressive cock out of her as semen began to drip out of her wet pussy and down her leg.
“Looks like you have some clean up to do, cuck.” He said, laughing between pants. Sarah gave a soft moan and kissed him, running her fingers through his hair. It was if my humiliation was turning her on all over again.
I sat there, cock deflated, as reality began to sink in. My roommate had stolen my girl, all from a simple game of Truth or Dare.”