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Cuckolded Over a Game of Truth or Dare

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“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.”

GF told her bestie I was a cuck. They decided to team up on me at a friend’s party. [part 4]

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Kane walked over to join our little foursome. I was chatting with Alyssa, and Kay was dancing with Patrick to the band. They were…very close. Don had gotten uncomfortable and left a few minutes earlier. Just as Kane approached, Patrick’s arms wrapped around Kay and his hands slid down to her ass, squeezing it firmly. He leaned in and kissed her. Kane looked at me with wide eyes, back at Patrick and Kay, and then at me again. He had a confused look on his face.

I started to speak up, “I uh…” – but Alyssa cut me off. “Great party!” she said to Patrick. Then she stepped into me, wrapped her arms around my neck and gave me a kiss. She moved her hips a little to the music, keeping her arms around me. I slowly put mine around her waist. She looked back at Kane, and I did too. Kane said, “thanks. Everything…okay over here?” My face must have been red. I could feel the heat in my cheeks. Alyssa answered before I could, “oh yeah, we’re having a great night.” She looked back at me and winked seductively and then kissed me again. “Grab my ass,” she whispered. I slid my hand down and laid it on her ass.

Kane laughed. “Well shit don’t let me be the fifth wheel,” he said. Alyssa chuckled at him. Kay and Patrick were in their own world. Patrick glanced over his shoulder and said “hey.” Kane nodded and looked at me again. “How was the pork?” He asked. I said, “awesome as always!” He said, “good – well I just stopped over to say hey.” He gave me a smirk and slapped me on the back once before turning to walk away.

Still holding onto Alyssa, I looked at her. Our faces were inches apart. She said, “you’re welcome.” I replied, “what?” with a confused look on my face. “You didn’t want everyone to find out… I was just trying to make it less awkward for you.” She pulled one arm down and removed my hand from her ass. She turned herself out of my arms and faced Kay. “Thank you,” I said.

Alyssa pointed to Kay. Patrick was still fondling her ass, squeezing it, as they danced back and forth with their bodies touching. “By the way, that’s how you grab a girl’s ass,” Alyssa said, looking back at me with a snarky smirk. I sighed through my nose as I turned and watched my girlfriend. She was loving his hands all over her. “I didn’t really know what was happening,” I said to Alyssa through a light chuckle, just as the song was ending. “Mmhm,” she replied sarcastically, “well I think that’s all you’re getting tonight.” Kay heard it and giggled. She turned her head toward me and laid it on Patrick’s chest. Looking me in the eyes, she nodded her head to agree with Alyssa.

As the band started the next song, Patrick and Kay came apart. They’d been playing mostly country, as you’d probably expect at a hog roast party on a farm. But with a little rock mixed in here and there. “I’m not about this music,” Patrick said. Kay agreed, “I know! It’s awful!” The two of them started talking about their music interests. Alyssa jumped in with them too as she pretty much has the same tastes as Kay.

Being a country fan, I was feeling left out of the conversation. “We should all go to a show together!” Kay said excitedly to the group. Patrick replied, “can bitch boy handle that?” Alyssa and Kay giggled. “Aww, he’s MY bitch boy though,” Kay said as she stepped toward me and put an arm around me. I rolled my eyes, unamused. Kay gave me a kiss and I could smell and taste Patrick. He reached over and put his hand between us. Then he grabbed Kay’s face and turned it toward him. “Hey… Absolutely not,” he said to her firmly. She stepped away from me and back to him. He reached out and slapped me on the shoulder. “I’m just fuckin’ with ya, squirt,” he said in a playful tone, “but don’t touch my girl.” The three of them laughed together.

I’d never felt so degraded. I knew no one heard him but the three of us, but I felt so exposed. As embarrassed as I was, I felt my dick slowly get hard. I watched him intently. He winked at me and slapped Kay’s ass. As Alyssa happened to look down and notice my boner, she yelled excitedly, “oh my God he likes it!!!”

GF told her bestie I was a cuck. They decided to team up on me at a friend’s party. [part 3]

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“Give me some of that!” Kay said playfully as Patrick held what was left of a bottle of BBQ sauce over his head away from her. “Give you some?” He mocked back at her. He set the sauce down and stepped into her, pressing his body up against her. We had waited out most of the crowd at the food tent, but there were still several people around and a lot of conversation going on. The band was playing now. I looked around nervously, praying that no one who knew me was seeing this.

Well, no one besides Alyssa. She was there too. She grabbed the sauce that Patrick had set down and stuck it right between their faces, breaking up a very tense moment between the two of them. Patrick grabbed the sauce and squirted some on Kay’s plate. “There, I gave you some,” he said. The two of them had gotten increasingly flirty over the last hour, and Alyssa was starting to get more comfortable with the whole situation. “Me next?” Alyssa asked Patrick. He chuckled and squirted some on her plate too.

I was behind the three of them in the line. Kay had been trying to include me, but Patrick was not really even acknowledging that I was there most of the time. “Is that the spicy one?” I asked. I held out my hand toward Patrick. He looked at me, and then set it down instead of handing it to me. Alyssa was between him and I. We locked eyes and she snickered at me picking it up off the table. “I hear he’ll give you some if you beg a little,” she said to me with a straight face. I rolled my eyes at her. She shot me back a very serious look and said, “don’t roll your eyes at me.”

A little stunned, I didn’t really know how to respond to that. It reminded me of the way Kay would talk to me when she was in a very dominant mood. “Sor-ry,” I replied, half sarcastically. She turned her attention back to Patrick and Kay, who had moved ahead to where the sides were. They looked like a couple, standing too close, chatting while getting their food, lots of unnecessary contact and looking at each other. Alyssa looked back to me as the two of us stepped forward and said, “aren’t they cute together?” She said it with a devious smirk, knowing it would get under my skin.

Walking back to where our cooler was, Kay and Patrick walked side by side, and Alyssa walked next to me, trailing a few feet behind them. “So you know I’m just having fun with you, right?” Alyssa asked me. I replied, “yeah I know. He just rubs me the wrong way.” Alyssa asked, “so if it were someone else, you’d go along with it more willingly? I mean…Kay told me you’ve even helped her pick up a guy before.” I laughed a little, recalling the time she was referencing. “Yeah,” I said, “it’s just fun, ya know. I get it’s odd to people, but to me it’s just a fetish like anyone else might have.” She nodded and said, “I’m not judging you for it. I think it’s awesome. But, you don’t mind me participating do you?” I shook my head no. “Doesn’t seem like I have a choice,” I said, starting to chuckle.

It was nice to laugh a little. I’d been so tightly wound all night. I started to feel a platonic connection with Alyssa. I was glad she decided to bring it up. “That’s right, you don’t!” She quipped back, winking at me.

Kay looked back at us. Well, at Alyssa. She made a face that I assume meant, “this is going so well.” I knew she wanted to fuck Patrick. If I didn’t know it before, I definitely did now. I felt my dick twitch a little, wondering what she was thinking. Kay loves making me uncomfortable. She has gotten really into the humiliation aspect of cuckolding. So I wondered how she would involve me. I said to Alyssa, “I just hope whatever happens can be discreet… I don’t want everyone to know about this.” She replied, “that’s understandable.”

When we got back to our cooler, Don was pulling out a beer. He wasn’t hungry so he’d stayed with the cooler. Or…maybe he was sensing how awkward things were getting and wanted a minute away from us? I’m not sure. Patrick noticed the bottle of Jameson, and said, “ooh, I’ll take a shot of that!” Don pulled it out and handed it to Patrick. Alyssa said, “oh yeah, we bought that for you. Well, he did.” She pointed at me. “You bought me this, really?” Patrick asked me. It was one of the few times he’d spoken to me. “Yeah, Kay said it’s what you liked.”

His face lit up. “damn bro, I come here, take your girl from you, and you give me booze?” My face turned so red. Don dropped the cooler lid and stepped away. Kay said, “isn’t he great?” with a big smile on her face, as she grabbed my arm and squeezed up to me. Patrick replied, “hell yeah, we should do this again sometime!” He laughed. “Now give her back!” He said with a light hearted grin, as he reached out and grabbed Kay’s other arm, pulling her back. She didn’t resist.

“Do what again?” Alyssa chimed in. She was instigating again. Patrick leaned down toward Kay. His hand came up to her face and he turned her head into him. He kissed her once. They looked at each other for a couple of seconds, nose to nose, and then slowly kissed twice more. He look back at Alyssa and said, “I’d do that again.” He looked at Kay and said, “would you?” She nodded her head yes, looking into his eyes. They backed away from each other. He started opening the bottle of whiskey and Alyssa looked at me with wide eyes. A smile came over her face as if to say she was happy for her friend.

My dick twitched and grew. As much as I couldn’t stand the guy, watching him grab Kay and kiss her, did something to me. She looked so infatuated. It was incredibly hot. I know Alyssa had to be thinking the same thing. I gave her a half smile and adjusted my legs to hide my growing boner.