First time with a man   added 5 years ago
  By: Cuffman  Age: 49  Country: United Kingdom

  • Currently 3.5/5 Stars.
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Views: 1301
Comments: 2
Favorited: 1
Rate by The Naughty Meter
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Categories: Anal Sex, Group Sex / Threesome, Oral Sex
Tags: oral sex Anal time first
Location: My House
Roleplay: Any
Fulfillment: I will tell you later
Nature: I will tell you later

This story is from my child hood, it never happened with Sean, but i offen wish it did.

I was twenty at the time, my girlfriend, Autumn, and I, had gone on vacation with her best friend, Sean, who was very gay indeed. We were going to spend a quiet week in a little cottage by the beach. We arrived and it was beautiful, lovely surroundings, we were buried away in nature. It was five minute walk up the street to the beach, but he had a hot tub around back in the nice fenced in back yard. Every day we would get up late in the afternoon, go down the street and grab lunch, and then we go swimming. After a few days we got sick of the same old routine, so Autumn, who was 21, went and picked up some liquor, a few twelve packs of beer and some Jack Daniel's.

We went to our respective rooms, and we slipped into our swimming suit, I usually just wore a pair of denim short. We settled into the hot tube. Autumn was about five feet tall, slender with b-cup boobs, a bit small, but they filled my hand perfectly, with dark brownish red hair, Sean was only a few inches taller than her, very slim, but surprisingly muscular once I saw him without his shirt, with short spiked blue hair. I practically towered above them at six feet, I was bit pudgy, with a nine inch cock, that barley fit in my girlfriend's tight pussy. As the night progressed me and Sean had as much beer as we cared to have, so we moved on to whiskey shots, at around midnight, I was getting pretty drunk, and Sean was blasted.

"I have to pee" Sean said as he stood and ran back inside

Autumn and I kissed and talked while he was gone. We were really enjoying ourselves. The night was a bit cold, but the hot tub more than made up for it. We snuggled and enjoyed ourselves, we were so into making out that we didn't notice the back door of the cottage swing open, and we didn't know that Sean was done inside until we heard him say quite excited "I'm back." We both stopped kissing and turned "My god" I said quietly to myself

Sean stood in the moonlight, bare ass naked, and his cock dangled, flaccid, between his legs. I couldn't help but stare, he was completely flaccid, not even half stock, and his cock was bigger than mine, and completely shaved, it was a bit startling at first actually. He walked over the hot tub and settled in. we all got back to drinking and talking.

After about another hour I realized that I had migrated a bit from Autumn, she didn't seem to notice. The big thing that made me realize was that my hand was sitting softly on Sean's thigh. "When the hell did this happen" I thought to myself, then I saw it, the site that I would never forget the rest of my adult life, Sean's cock, standing at full attention, because of my touch. It was at least ten and a half inches long, and quite wide. I stared down at it, Autumn, and Sean didn't seem to notice that I had dropped out of the conversation. I tried to join back in but kept getting distracted.

And then I noticed my hand migrating north, as if I had no power over it. I had never touched a cock besides my own, and I had certainly thought I might be gay, but I was curious, as all men are at some point, even if they won't admit it. But a switch in my brain suddenly flipped, I didn't care what it meant, and I didn't care what the reaction would be, I wanted so badly to hold that cock in my hands, I began to massage Sean's leg, slowly working my way up, higher and higher. I'm sure he noticed, but he did a good job hiding it. until I was at his shaven crotch I curiously, slowly, slid my hand around to his balls, and I held them in my hand.

At this point he smiled, looking over at me staring at his cock, holding his soft balls in my hand and playing with them, the way I liked mine to be played with. When I noticed him looking at me, I glanced over to Autumn, I was afraid that she would be furious, but she wasn't, she was smiling at me too. It took this as cue to keep on going, so I massaged his balls for a bit longer, and worked my way slowly to his shaft, I hesitated a moment before taking it in my hand, I was shaking and terrified, but all in a good way. I rapped my fingers around his fat cock, it was amazing, I could hardly touch my finger tips together. I just held it for a few moments, letting the exhilaration flow through me, and I began to slowly stroke it, up and down. Sean leaned his head back, his breathing got faster and faster. It was the most amazing thing.

After a few minutes of stroking, he grabbed my wrist. And stopped me "Do you want to be a little more Adventurous?" He asked

"I think so." I replied in a soft wobbly voice.

He boosted himself out of the tub, and sat on the edge, his massive cock sticking up toward the stars. I knew exactly what he had in mind, and I was completely ready, I turned to look at Autumn, silently asking for her approval, and smiled softly and nodded.

I repositioned myself so that I was between his legs, I looked at his cock for a good long time, taking it all in, and I slowly, softly began to lick up and down his shaft, it was an awesome feeling, my tongue touching another man's swollen cock, and I knew I was doing something right, because he moaned as my tongue hit the tip. I circled my tongue around the head of cock for a few second before hesitantly opening my mouth,

I sucked softly on this head for a bit, then went further, his cock filled my mouth quite well, and it was an exciting new experience, as my head bobbed up and down, taking a little more each time, I noticed I had almost half his cock in my mouth, and, as if I had been doing this for years, I slid further and let his cock tickle the back of my throat, I didn't even think about throwing up. I continued like this, he moaned quietly with delight, until finally I felt his cock begin to jerk and pulse. His head shot up and he looked down at me.

"You don't have to if you don't want to." He said

I kept going, moving my tongue all over his cock as I bobbed my head up and down. Hearing him moan harder and louder and finally he grabbed the hair on the back of my head, and he held my mouth over his cock, It felt amazing being held in place like this, and finally it happened, I felt squirt after squirt of his cum hit the back of my throat, and I swallowed every drop I could. It was delicious, the best thing I had ever tasted. And it even felt good as mouth began to overflow and the juices leaked on the corners and down my chin. He let go of the back of my head, and I slipped his cock out of my mouth still sucking the cum out frantically.

"How was that?" He asked breathless

"Holy shit." I said "That was awesome."

We all got up, toweled off, and went off to get ready for bed. Autumn and I decided to take a shower, as we stepped in under the warm running water, she immediately grabbed me and kissed me violently.

"That was the sexiest thing I have ever seen." She said letting me up for air

"It was pretty awesome." I replied with a big smile on my face

She gave me a blowjob as we showered and when she finished we washed each other, and then dried off and slipped into our pajamas. We curled up in bed watching some late night talk show when a knock came at the door. The door opened and there was Sean.

"Hey, I don't have TV in my room, can I watch with you guys?" He asked

"Yeah, go ahead." Autumn said

He crawled into bed next to me and snuggled up I put my arms around both of them. In no time flat Sean was rubbing my throbbing cock. I reached under the blanket and unbuttoned my pajama pants. I never wore underwear so my cock popped right out, and he wrapped his hand around it. stroking it softly, he was much better I, or even Autumn, was. As I leaned back my head to enjoy Autumn threw back the covers and began kissing me as her hand played with my balls. Now this was amazing.

Sean looked up at me, with a mischievous smile on his face. "How about something really wild?" he said.

"Sounds good." I said smiling right back

He stood up and slipped off his pants and shirt, he was already hard "don't touch that cock, Autumn, he's mine tonight." Sean said before rushing out of the room. He came back several seconds later with a small tube.

"What's that?" I asked

"It's lube, we're gonna need it."

"I don't think I can"

He cut me off "not for me, for you." He pulled my pants all the way off and Autumn pulled my shirt up over my head. Then he crawled up, squirted some lube into the [palm of his hand began rubbing it all over my cock, this felt amazing on it's own, but I didn't know what I was in for. After my Cock was sufficiently lubed he stood up, walked to the edge of the bed, and bent over with his elbows on the mattress. And then he rubbed lube into his asshole. He motioned me to come around back. I stood and walked around behind him.

"Don't be shy, I'm used to his, just go ahead."

I slowly and hesitantly pointed my cock at his ass, then I began to rub the head around on his asshole, this got him worked up for more. So after a few seconds of this, I began to cautiously push my head into his hole. The slick soft feeling of his asshole engulfing my cock made my legs turn to rubber, and I felt like I would come right there and then. So I stopped for a moment before I slid it the rest of the way in, it went relatively easy, with only a little resistance. And I began to slowly thrust. In and out, in and out, and Sean moaned loudly.

"OH GOD! OH GOD! FUCK THAT ASS! FUCK ME HARD!"

And I began to move faster and harder, his ass was tight around my cock, my dick ached from how tight it was but it was so good. I reached around to take hold of his cock as I fucked his ass. And I jerked it slowly, every now and then looking up to see Autumn rubbing her clit, she was completely naked as well.

"OH FUCK!" Sean screamed "FUCK ME HARDER! HURT ME!"

I let go of his cock and took a firm hold of his hips, and I thrust wildly forward I would pull his ass back harder and harder. My balls began to tense and my cock throbbed, I couldn't maintain the same firm hold anymore, so Sean began to force him self back, grunting and groaning, in rhythm with my thrusts. I grunted and groaned in rhythm with him. And I reached back around and grabbed his cock and jerked it firmly as I thrust deeper in his asshole. As I felt my cock shoot cum deep in his asshole, his cum shot out on the edge of the bed, and the floor and all over my fingers. I slid my cock from his ass, which felt almost as good as putting it in, and cum leaked as his hole quivered. I sucked the cum from my fingers, and kissed Sean heavily on the lips, and then I laid my face into Autumn pussy and finished her off as well. Now that we had all cum we collapsed in a heap on the bed, our hearts beating, and our breath heavy.

We watched a few movies trying to fall asleep, noticing the sun peaking up over the trees outside, and we realized none of would be sleeping. As I rolled over to try and sleep I saw that Sean was hard again. So I began to stroke his cock, and he rolled over to me, and kissed me, we began to let our tongues dance together in each other's mouths. There was one last thing I wanted to try.

"Hey Sean." I said breaking our kiss "I wanna try it now."

He looked at me and began to run his hand down my chest, Autumn propped herself up on her elbows, and Sean ran his fingers over my nipples, and around my placing his hand on my butt, tugging ever so gently signaling me to roll onto my belly, and O complied. He picked up the bottle of lube again, and rubbed it all over his hand, gently massage the my ass crack. Then he began to move his finger in circles around my hole. Then he pushed one finger in, I let out a loud sigh. He worked his finger in and out for a minute before adding a second, and a eventually a third and fourth. Then he began to kiss my neck.

"Get on your hands and knees." He whispered in my ear

I got up on my hands and knees and he got on his knees on the bed.

"This is going to hurt at first. Then you'll get used to it." He said softly "if you want me to stop just say so."

Then I felt it, that first bit of pressure as he pressed the head of his cock to my hole. I felt it slowly and agonizingly push it's way in, it was such an amazing pain, and I couldn't get enough of it. his giant cock stretched out my ass and it was excruciating, but I didn't once tell him to stop, because it hurt so good. I felt the shaft force it's way in, and then his stopped, he had really filled my up with his cock. He stood motionless for a moment, and the pain slowly faded into pleasure.

Then he began to slowly thrust, the feeling of his cock running in and out of m asshole, and my asshole sucking in around it, was amazing, he began to speed up, until he was moving a quick pace, fucking me in the ass. I never imagined it would feel so good. I closed my eyes and my jaw dropped out of pure ecstasy. Then I felt Autumn's soft Tongue against me cock. I opened my eyes to see her pussy, glistening in the early morning sunlight. She sucked softly and Sean fucked my ass. I lowered my face into her pussy and lapped at it softly. Sean increased speed now and then and it felt better and better. I lifted my head from Autumn's pussy, I couldn't contain the moaning any more.

"Fuck me harder." I moaned "FUUUCK MEEEEE!"

And he began to move harder and harder as Autumn took my cock deeper into her mouth.

"Use me, I'm your little fuck toy, ram it in all you want."

And that was all he needed, he fucked me ruthlessly. He grabbed my hips and rammed it in harder and harder. I moaned louder and louder, and then I felt his hand grip my hips, holding me tightly as he fucked me raw. His held fell back and he let out a loud moan and I felt his cum shoot deep into my ass, so much of it that it squirted out and dribbled down the back of my legs. Then he slid it slowly out. It was every bit as amazing as I thought it would be.

Autumn turned me over and positioned her pussy over my face as Sean enveloped my entire cock. As I licked Autumn's until she came over and over again. And then I shot my load deep in Sean's throat, he swallowed every drop. We all moved around again and cuddled up to one another. Autumn wanted to taste a cock that had just come out of an ass, so she laid down across me an d sucked Sean's cock for a little while, While I played with her asshole, and made out with Sean.

I've never had sex with another man, but I still do enjoy ass play. On our anniversary I bought Autumn a strap on, so she could see me get fucked whenever she wanted.




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