By: expatt & Ryan Michaels
Dean had been going out with my older brother, Matt, for about two years when I found out he'd screwed another guy, a guy named Eric. Worse yet, Eric was a good friend of Matt's. I knew I could use this to my advantage.
I was eighteen and devious. I'd had a huge crush on Dean from the first time Matt had brought him home. He was twenty-two, and had a broad hairless chest and big muscled shoulders. His face was masculine and he was quick with a smile. I loved hanging out with him, and always tried to see him without his shirt on. He came away with us one summer up to the beach house, and I loved seeing him in his shorts and nothing else. He was my fantasy man, which led to many a time of me fucking myself with my dildo, pretending it was his cock in me, while rubbing my clit to orgasm.
I still couldn't believe he was gay. No one would ever think it. He was the epitome of the 'typical' straight man in appearance and demeanor. But not only was he gay, he was one of those gay men that was disgusted by the very thought of getting anywhere near a pussy, let alone sticking their dick in one.
I found out he screwed Eric because I overheard a telephone conversation between the two. Dean had been spending the weekend at our house while mom and dad were away at the beach house. Matt was in the shower and Dean thought he was the only other person in the house. He was, until I'd come home and (unintentionally) picked up the phone, finding that Dean was using the one in the bedroom. I heard them talking about how nobody could find out that they'd fucked, and Eric was going on and on saying how much he really liked Dean, but he promised him that he wouldn't say anything. I listened to the whole thing, and suddenly had the most amazing idea!
So, one day when I knew that Matt was working, I went over to Dean's house. He lived in a small apartment on the other side of town and worked from home. He was surprised to see me, but invited me in. We were sitting on the couch and I could tell he wondered what I was doing there.
"Dean, I've got a deal for you," I told him.
He sat back on the couch with a smile on his face. God, he was sexy. I was so hoping that my plan would work. "What's that?" he asked casually. He had no idea what I was about to suggest.
"Well, first off, I need to tell you that I know that you fucked Eric Sanderson last month." I paused there to let that sink in.
The color drained from his face and he stared at me. "Shit," he said under his breath a moment later. "How did you find out? Does Matt know?"
"No, Matt doesn't know. I overheard you talking to Eric last weekend at our house. And I haven't told anyone."
I could tell that Dean's mind was spinning. He didn't know what to do.
"Are you going to tell Matt?" he asked me.
God, this was great. He was completely at my mercy! "That depends," I said. I wanted his agony to last.
"On what?"
"On whether or not you'll fuck me," I told him.
He looked at me with disbelief. "What?" he said, incredulously.
"I said I want you to fuck me." I was getting more and more confident.
"Is this some kind of joke?" he asked, unsure of my seriousness.
I shook my head with a smirk on my face.
"You must be out of your fucking mind!" he said. "I'm a fag, in case you've forgotten. I don't do pussy. I'm not gonna start now, and I definitely wouldn't start with you, even if I had the inkling, which trust me, I never will. You're my boyfriend's sister for Christ's sake! Jesus Christ Kelly, are you drunk or high or something or think this is actually a funny joke to play, because I know you can't be serious!"
He was raving. I just let him rant. It didn't worry me. I felt pretty sure he'd agree to my conditions. He was deeply in love with Matt, and the two were even planning to get married at some point. (Gay marriage is legal where we live). I loved my brother, but, still, right then, in that moment, I wanted Dean's cock in my pussy more than anything else in the world!
"I'm completely sober and totally serious. All I want is your cock in my tight pussy. If you don't do it, then I'll tell Matt what I heard on the phone. He'll dump you, you know he will," I said, smugly.
"You fucking bitch!" he grumbled and sat back down heavily on the couch.
"Dean. I only want you to do this once. And I promise I'll never ask again, and I will never say anything to Matt about Eric."
He didn't say anything, rather just lay back on the couch with his hands over his face. He was thinking. I sat across from him, staring at the bulge in his pants. God, it was big, and he was so cute.
"Just once, right?" he asked removing his hands from his face.
My heart leapt. He was considering it!
"Yup, just once; I wanna suck your dick, and then I want you to fuck me."
He was silent and just looked at me for a long time. "I can't fuckin' believe this," he finally said. "I thought you were a nice girl, but today you've shown me what a little cunt you really are."
"I'm not a cunt. I'm just a girl who gets moist whenever she's around you."
He made a face when I said that, getting a mental image I imagine.
"Yeah… I'll do it," he said with resistance and a bit of disgust in his voice. "Only because I really love your brother and don't want to lose him. But as far as you and I are concerned, I will never have anything to do with you again after this!"
I didn't care. All I heard were the words "I'll do it". My pussy was already getting wet.
He was still sitting on the couch, so I told him to stand up and take his pants off. He did, somewhat slowly and reluctantly. Once he did, I reached out and pulled his underwear down. His heavy cock flopped over his balls as he just stood there wearing only a t-shirt. God, he was big! Now I knew one of the things my brother liked about him and I couldn't believe I was actually about to get my mouth around that! I knelt on the floor in front of him. He stood proudly, not looking down at me.
I didn't want to rush it. I knew I was being a bitch, but I meant what I said to him. I only wanted it once, and I would keep my promise about not saying anything. So because it was going to be a one-off, I wanted to make it the best I possibly could.
I held his heavy cock in the palm of my hand. His body tensed at the touch and thought of a female hand on his private part. His cock was fat and wrinkled. I lifted it up so I could see his balls and he crinkled his face up and groaned - more a groan of disgust than arousal. His balls were big too and hung really low. I loved that his cock wasn't hard. That way I could fit the whole thing in my mouth and feel it grow.
I licked his balls. I felt him clench his ass. I knew he wasn't happy, but I didn't care. I had dreamed about sucking his dick for so long. I nuzzled my face into his crotch and licked the line between his torso and his legs. My face was up against his nut-sack and I pushed his limp cock up onto my cheek. I felt it growing a bit.
As I took his mostly soft, but long cock into my warm mouth, it squashed up against the back of my throat. He groaned, again not a groan of delight, and I began to suck on it while using my tongue to massage the underside of his shaft. That worked. I could feel it get bigger and swell. I knew that when it was hard I wouldn't be able to fit it all in my mouth. I had to let some of it out, but I kept sucking and covering it with saliva. He just got bigger and bigger.
I took the whole thing out and kept pumping the shaft. It was dripping with my spit and I played with the end of it with my finger. This whole time Dean was just standing still. He didn't say a word and didn't touch me. His hands were by his sides and he wasn't giving me any encouragement at all, as he stared straight ahead, most likely wishing he was anywhere else but there.
"Well, even if you're not liking it, your cock sure is," I giggled, hoping he'd loosen up.
"Go fuck yourself," he said. The hate in his voice kind of scared me, but I was in too deep to stop. The damage was already done, so I figured I may as well enjoy it.
"No need, when I have you to do it for me," I said giving his long shaft a few firm strokes. Dean just snarled at the thought of the inevitable event to come.
My pussy had completely soaked my panties by this point, so I took a second to take my jeans and panties off. It felt a lot better now that my pussy was exposed to the air. I knew I couldn't rub my clit because I would orgasm quickly, as turned on as I was.
Dean glanced down and then quickly looked away, making a gagging noise. I didn't care, he was going to fuck me no matter how disgusted the thought made him. He knew he had to, and that's all I cared about.
I went back to work on Dean's big cock. I wasn't a virgin, so I'd seen a hard cock before, but never one this big – or this thick! I'd say it was about eight inches long and as thick as the hitting end of a baseball bat – well maybe not literally, but you get the idea. I really liked how it was covered with veins, and there was a thick cord which ran along the underside of the shaft from his balls up to the head of his dick. My tongue ran up and down the huge rod, covering it with spit. I loved licking his balls, too, and alternated between the two. When I was sucking his cock (I couldn't take it all) I would fondle his balls, and when I was licking and sucking his balls I would stroke his cock.
As much as I loved working his big slab of meat with my hands and mouth, I thought it was about time to get his cock in my tight, wet cunt. The only other guy to fuck me was a guy named Kevin. He lived over the back from us and we ended up hooking up once (It was the first time for both of us), and after that, every now and then, when he was horny, or if I was, he'd come over and fuck me. But Kevin wasn't nearly as big as Dean! Kevin was about an average six inches and more on the skinny side than thick. Of course, I didn't know average and skinny was average and skinny until laying eyes on a big, thick cock like Deans.
I was a bit nervous actually, because I thought it might hurt. It was the thickness more than the length that worried me. But then I remembered that I'd had other things in my pussy before. Besides the dildo that I mentioned, one of my favorite things to do was to get a big fat cucumber (cliché, I know) and slip it in and out of my cunt. So I knew my pussy could take something as big as Dean. I'd come prepared and pulled a condom out of my pants pocket, held it up and grinned at him.
He looked down at me for the first time. "Regular condoms are too tight on me," he said.
"Oh, well do you have any?"
"Nope, sorry. I guess this is as far as we go," he said smiling for the first time, thinking he had gotten out of having to fuck pussy. But he wasn't getting off the hook that easily!
"That's ok, I'm on the pill. You can just pull out before you cum."
He groaned. "Ugh, how do you want it?" he asked flatly. He'd lost the hatred in his eyes and it was more a look of resignation.
It was then that I came to the realization that when I used my dildo and the cucumber, I was in control. I wouldn't be with Dean's large schlong. I quickly came up with a solution. "Lie on your back on the floor. I'll sit down on it," I replied, figuring that would give me control over his big dick going in me.
He lay down, grabbed a cushion from the couch, put his head on the pillow and shut his eyes. Like I said, he was one of those gay guys who got grossed out even at the thought of pussy, so I guess if he had to do it he didn't want to have to see it.
I took another look at him. My heart did a flip as I couldn't believe that I was about to sit on his dick. Even if he did hate me for the rest of my life, right at that moment I didn't care. All I wanted was to be fucked by him. I didn't care about the consequences.
His cock was still hard and pointing up at his face. I picked it up and sucked it one last time. Then I spit on it and spread the spit with my hand. When it was slick, I climbed over his body and straddled him with my pussy aimed directly at his cock.
"I'm going to lower myself onto you now," I said giving him warning.
He didn't reply.
The big head of his cock was pushed against my pussy lips. I sat down a bit more and the head slipped inside. Dean scrunched his closed eyes tightly. His cock was stretching my cunt pretty good, but I was so horny for him it didn't hurt. I pushed a little bit harder, and then pushed down again until he was about a third of the way in.
I knew that it must have felt great on Dean's cock, even if he wasn't into girls. A hole is a hole and a hot, tight hole wrapped around a cock had to feel fantastic to any guy, no matter their orientation. I ran my fingers over his body and pinched one of his hard little nipples, making him jump.
After a few moments I knew I was ready for all of him. In one smooth movement I sat right down on him, taking his entire thick shaft up my tight cunt. This time he let out a small groan. Yes, I thought. You're enjoying this! I sat on his pelvis and used my pussy to squeeze his dick. He groaned again.
I wasn't moving up and down yet, just squeezing and contracting, giving his cock a massage. He still wasn't looking at me, but I knew he had to be enjoying it. He was moving beneath me, every now and then pushing into me as if he wanted to be deeper inside.
Slowly I started to pull myself up off his cock. I could feel it slipping out of me. I leaned forward so that only the head of his cock was still in me. And then just as slowly, I sat back down. God! I thought I would have an orgasm right then! My fingers grasped his muscled shoulders.
"Oh, that feels so good Dean," I told him. Still, he didn't respond to me.
"Dean?"
He opened his eyes and looked at me.
"I want you to fuck me like you fuck Matt, and like you fucked Eric. Come on Dean, fuck me, please," I begged.
Something changed in his face. I could see him smile a little bit, like he knew his big cock had sent me into a world of pleasure and he was regaining control of the situation. Without taking his cock out of my cunt he rolled me over onto my back, my legs now over his shoulders and him hovering above me. I braced my hands on his biceps.
"So, you want me to fuck you, huh?" Dean asked, gently moving his cock inside me.
"Oh, yes," I moaned.
"You want me to fuck you like I fuck Matt and like I fucked Eric, is that what you want?" he asked as he slowly started sliding his cock out of me and then moving it back in again. It was too much for me.
"Yes, oh yes, please fuck me!" I practically screamed.
"And a good fuck buys your silence?"
"Yes!" I screamed.
"Ok, well get ready, because you're gonna get exactly what you asked for!" At first I thought he was getting into it, but then suddenly the pace changed and Dean started pounding my pussy hard!
I cried out. I couldn't help it. It hurt. Every time he banged his hard cock up my tight cunt I let out a gasp and a cry.
He put his hand over my mouth, without losing rhythm, and said, "You wanted me to fuck you, and you wanted it like I give it to Matt and how I gave it to Eric. Well this is how I fuck them… hard… so lie there and take what you begged for!" Far from being into it, if he had to do it, I guess this was his revenge for what I was forcing him to do.
His balls were slapping hard against my ass as he pounded me, and he was getting faster. Just when I thought I couldn't take it any longer the discomfort slowly began to turn into pleasure, intense pleasure! My pussy was on fire, and without even touching my clit I knew I was about to have an orgasm.
"Oh, God, fuck me Dean! Fuck me! Yeah, oh, yeah," I panted.
I guess now that he knew I was enjoying it, it ruined his 'revenge' and he slowed down. I didn't want it slow, now that I was used to his size. I wanted it hard, hard like he had been giving it to me just a moment ago. So I decided to try a bit of reverse psychology to get what I wanted.
"Oh, yeah, mmm, that's much better like that. It was too hard before. Oh, yeah, just keep doing it like that. Don't stop."
It worked. Dean started to pound his big cock into me hard and fast and without mercy.
"Oh, God, not so hard. Please, not so hard," I groaned playing along, and he kept pounding it into me as hard as he could.
"Oh, oh, oh. Oh my god," I groaned only moments later, and then I was hit with the waves of an orgasm like I had never had before.
Dean never stopped pumping while I was orgasming, and I knew he was close. He suddenly stopped pounding me and yanked his cock out of me. He grabbed it in his fist, gave it a few quick strokes, and then he froze and let out a grunt. His whole body spasmed and I saw his cock swell as his first spurt of cum landed between my tits. He must have spurted about five times as I felt his hot cum splashing on my stomach.
He was panting loudly, and his t-shirt was covered with sweat. He sat back resting his ass on his heels a little bit away from me, breathing deeply, looking at his half-hard cock. It was covered with my pussy juices and there was a bead of cum sitting on the piss slit, which oozed until it fell to the ground.
I was still lying on the floor and could feel my pussy gaping open like never before from his fat cock. Knowing he had stretched me so wide with that big cock, and shot his cum on my body, made me so horny that I wanted him to fuck me again. But that was out of the question – a promise was a promise.
Dean got up off the floor and stood over me. "I'm going for a shower. Don't be here when I get back or you'll regret it," he snapped.
"Don't forget what I know Dean. I told you I wouldn't tell anyone, and I'll keep my promise. But you'd better be nice to me, or who knows what might happen." I was trying to sound cocky, but in truth I was kind of scared after his last comment. I'd regret it? He was angry, and I didn't know what he might do or how he'd treat me now. I was almost regretting what I'd done… almost!
Dean went for a shower. I wiped up the mess, got dressed and left.
Dean and Matt did end up getting married. He and I never talked about what happened, and I kept my promise and never told anyone what I knew. Dean treated me with absolute indifference and never spoke to me unless he absolutely had to.
Sometimes I think perhaps I shouldn't have done what I did… but mostly I remember it as the best fuck I've ever had!
Dean glanced down and then quickly looked away, making a gagging noise. I didn't care, he was going to fuck me no matter how disgusted the thought made him. He knew he had to, and that's all I cared about.
I went back to work on Dean's big cock. I wasn't a virgin, so I'd seen a hard cock before, but never one this big – or this thick! I'd say it was about eight inches long and as thick as the hitting end of a baseball bat – well maybe not literally, but you get the idea. I really liked how it was covered with veins, and there was a thick cord which ran along the underside of the shaft from his balls up to the head of his dick. My tongue ran up and down the huge rod, covering it with spit. I loved licking his balls, too, and alternated between the two. When I was sucking his cock (I couldn't take it all) I would fondle his balls, and when I was licking and sucking his balls I would stroke his cock.
As much as I loved working his big slab of meat with my hands and mouth, I thought it was about time to get his cock in my tight, wet cunt. The only other guy to fuck me was a guy named Kevin. He lived over the back from us and we ended up hooking up once (It was the first time for both of us), and after that, every now and then, when he was horny, or if I was, he'd come over and fuck me. But Kevin wasn't nearly as big as Dean! Kevin was about an average six inches and more on the skinny side than thick. Of course, I didn't know average and skinny was average and skinny until laying eyes on a big, thick cock like Deans.
I was a bit nervous actually, because I thought it might hurt. It was the thickness more than the length that worried me. But then I remembered that I'd had other things in my pussy before. Besides the dildo that I mentioned, one of my favorite things to do was to get a big fat cucumber (cliché, I know) and slip it in and out of my cunt. So I knew my pussy could take something as big as Dean. I'd come prepared and pulled a condom out of my pants pocket, held it up and grinned at him.
He looked down at me for the first time. "Regular condoms are too tight on me," he said.
"Oh, well do you have any?"
"Nope, sorry. I guess this is as far as we go," he said smiling for the first time, thinking he had gotten out of having to fuck pussy. But he wasn't getting off the hook that easily!
"That's ok, I'm on the pill. You can just pull out before you cum."
He groaned. "Ugh, how do you want it?" he asked flatly. He'd lost the hatred in his eyes and it was more a look of resignation.
It was then that I came to the realization that when I used my dildo and the cucumber, I was in control. I wouldn't be with Dean's large schlong. I quickly came up with a solution. "Lie on your back on the floor. I'll sit down on it," I replied, figuring that would give me control over his big dick going in me.
He lay down, grabbed a cushion from the couch, put his head on the pillow and shut his eyes. Like I said, he was one of those gay guys who got grossed out even at the thought of pussy, so I guess if he had to do it he didn't want to have to see it.
I took another look at him. My heart did a flip as I couldn't believe that I was about to sit on his dick. Even if he did hate me for the rest of my life, right at that moment I didn't care. All I wanted was to be fucked by him. I didn't care about the consequences.
His cock was still hard and pointing up at his face. I picked it up and sucked it one last time. Then I spit on it and spread the spit with my hand. When it was slick, I climbed over his body and straddled him with my pussy aimed directly at his cock.
"I'm going to lower myself onto you now," I said giving him warning.
He didn't reply.
The big head of his cock was pushed against my pussy lips. I sat down a bit more and the head slipped inside. Dean scrunched his closed eyes tightly. His cock was stretching my cunt pretty good, but I was so horny for him it didn't hurt. I pushed a little bit harder, and then pushed down again until he was about a third of the way in.
I knew that it must have felt great on Dean's cock, even if he wasn't into girls. A hole is a hole and a hot, tight hole wrapped around a cock had to feel fantastic to any guy, no matter their orientation. I ran my fingers over his body and pinched one of his hard little nipples, making him jump.
After a few moments I knew I was ready for all of him. In one smooth movement I sat right down on him, taking his entire thick shaft up my tight cunt. This time he let out a small groan. Yes, I thought. You're enjoying this! I sat on his pelvis and used my pussy to squeeze his dick. He groaned again.
I wasn't moving up and down yet, just squeezing and contracting, giving his cock a massage. He still wasn't looking at me, but I knew he had to be enjoying it. He was moving beneath me, every now and then pushing into me as if he wanted to be deeper inside.
Slowly I started to pull myself up off his cock. I could feel it slipping out of me. I leaned forward so that only the head of his cock was still in me. And then just as slowly, I sat back down. God! I thought I would have an orgasm right then! My fingers grasped his muscled shoulders.
"Oh, that feels so good Dean," I told him. Still, he didn't respond to me.
"Dean?"
He opened his eyes and looked at me.
"I want you to fuck me like you fuck Matt, and like you fucked Eric. Come on Dean, fuck me, please," I begged.
Something changed in his face. I could see him smile a little bit, like he knew his big cock had sent me into a world of pleasure and he was regaining control of the situation. Without taking his cock out of my cunt he rolled me over onto my back, my legs now over his shoulders and him hovering above me. I braced my hands on his biceps.
"So, you want me to fuck you, huh?" Dean asked, gently moving his cock inside me.
"Oh, yes," I moaned.
"You want me to fuck you like I fuck Matt and like I fucked Eric, is that what you want?" he asked as he slowly started sliding his cock out of me and then moving it back in again. It was too much for me.
"Yes, oh yes, please fuck me!" I practically screamed.
"And a good fuck buys your silence?"
"Yes!" I screamed.
"Ok, well get ready, because you're gonna get exactly what you asked for!" At first I thought he was getting into it, but then suddenly the pace changed and Dean started pounding my pussy hard!
I cried out. I couldn't help it. It hurt. Every time he banged his hard cock up my tight cunt I let out a gasp and a cry.
He put his hand over my mouth, without losing rhythm, and said, "You wanted me to fuck you, and you wanted it like I give it to Matt and how I gave it to Eric. Well this is how I fuck them… hard… so lie there and take what you begged for!" Far from being into it, if he had to do it, I guess this was his revenge for what I was forcing him to do.
His balls were slapping hard against my ass as he pounded me, and he was getting faster. Just when I thought I couldn't take it any longer the discomfort slowly began to turn into pleasure, intense pleasure! My pussy was on fire, and without even touching my clit I knew I was about to have an orgasm.
"Oh, God, fuck me Dean! Fuck me! Yeah, oh, yeah," I panted.
I guess now that he knew I was enjoying it, it ruined his 'revenge' and he slowed down. I didn't want it slow, now that I was used to his size. I wanted it hard, hard like he had been giving it to me just a moment ago. So I decided to try a bit of reverse psychology to get what I wanted.
"Oh, yeah, mmm, that's much better like that. It was too hard before. Oh, yeah, just keep doing it like that. Don't stop."
It worked. Dean started to pound his big cock into me hard and fast and without mercy.
"Oh, God, not so hard. Please, not so hard," I groaned playing along, and he kept pounding it into me as hard as he could.
"Oh, oh, oh. Oh my god," I groaned only moments later, and then I was hit with the waves of an orgasm like I had never had before.
Dean never stopped pumping while I was orgasming, and I knew he was close. He suddenly stopped pounding me and yanked his cock out of me. He grabbed it in his fist, gave it a few quick strokes, and then he froze and let out a grunt. His whole body spasmed and I saw his cock swell as his first spurt of cum landed between my tits. He must have spurted about five times as I felt his hot cum splashing on my stomach.
He was panting loudly, and his t-shirt was covered with sweat. He sat back resting his ass on his heels a little bit away from me, breathing deeply, looking at his half-hard cock. It was covered with my pussy juices and there was a bead of cum sitting on the piss slit, which oozed until it fell to the ground.
I was still lying on the floor and could feel my pussy gaping open like never before from his fat cock. Knowing he had stretched me so wide with that big cock, and shot his cum on my body, made me so horny that I wanted him to fuck me again. But that was out of the question – a promise was a promise.
Dean got up off the floor and stood over me. "I'm going for a shower. Don't be here when I get back or you'll regret it," he snapped.
"Don't forget what I know Dean. I told you I wouldn't tell anyone, and I'll keep my promise. But you'd better be nice to me, or who knows what might happen." I was trying to sound cocky, but in truth I was kind of scared after his last comment. I'd regret it? He was angry, and I didn't know what he might do or how he'd treat me now. I was almost regretting what I'd done… almost!
Dean went for a shower. I wiped up the mess, got dressed and left.
Dean and Matt did end up getting married. He and I never talked about what happened, and I kept my promise and never told anyone what I knew. Dean treated me with absolute indifference and never spoke to me unless he absolutely had to.
Sometimes I think perhaps I shouldn't have done what I did… but mostly I remember it as the best fuck I've ever had!
Read the All Male Version
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