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- Aug 16, 2012
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- Indianapolis, Indiana, US
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- 50% Straight, 50% Gay
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- Male
Here we sat, My boyfriend of 5 years, Steve, and Jon, my best friend of about 4 years and Steve’s friend of about 16 years. They’ve known each other since they were kids. Jon and i quickly became best friends due to a lot of the same interests. Including girls. Even though I’m bi and in a same sex long term relationship. Steve was ok with it. But there was a connection between Jon and that even Steve and I didn’t have.
We’d been sitting here watching tV for a few hours. And we decided to put on some porn. We even joked about Steve and I putting on a show for Jon. But he declined enthusiastically confirming over and over he was straight.
After a while. He began to complain about how his girlfriend, his first serious girlfriend ever and the only woman he had ever been with refused to let him go bareback. She was worried mostly about having a baby and also STDs. They had sex a lot. But he always had to wear a condom
Now. I’m over 10 years older than both of them at the ripe age of 35.
“Awe” I laughed.
“Seriously. I just want to know what it feels like man” Jon groaned.
“It feels great” I sneered.
“Yeah it fucking does” Steve said laughing playfully. Especially fucking Matt’s tight ass”
“Why thank you” I winked and smiled.
“You fuck him BAREBACK, Steve?” Jon asked…
“Uh yeah…. MY man gets to ride Bareback I ain’t gonna get pregnant and we were both our firsts” I smiled and winked at Jon this time.
“Fuuucckk” he groaned. “Lucky dick” he snorted.
“Yes it is” I laughed.
“Yeah. I am lucky” Steve said and winked at me
“You should let me……” Jon said “hahah I’m kidding “ he quickly added
“Anytime baby” I flirted but was kidding, kind of
“Yeah. You should….. “ Steve said
My head whipped around at Steve “WHAT?” I said startled
“He’s my friend and your best friend. Of course you should let him” Steve laughed…. Then went silent.
“Guys. I’m fucking around. I know it can’t happen. He’s fucking huge and you’re ass is the tightest I’ve ever seen” Steve finally said
“Oohhh Hahahaa “ Jon and I replied in unison
But. My mind was spinning… I’d never seen his cock. Is he that big? Steve was big, but he thinks Jon is HUGE….. I’ll admit. My interest was triggered.
“How big?” I asked
“He’s really big Matt… you can’t handle it” Steve said snarky
“What the hell man..” I said irritated. “I can take it. Eventually… you act like he’s too much man for me!”
“Guys…. It’s all a joke” Jon laughed nervously
“Fuck it… show him Jon” Steve said.
“What?” Jon said staring between me and Steve. “Dude. Y’all in a relationship”
“It’s ok Jon. Show him” Steve said smiling. “We are all friends and I’ve seen it already.”
“Uhm……. Well… ok” Jon undid his button on his jeans and unzipped them. He fished out a long thick FLACCID dick….
“Dude. What the hell? You’re not even hard?” Steve ribbed him. “Matt can’t tell how big you are like that!”
“Looks pretty big to me” I said softly watching Jon look up at me… he smiled and I swear I saw his cock begin to get erect.
“Dude. Why aren’t you hard?” Steve said.
“I’m sorry! This is a little awkward!!” Jon yelled laughing.
“Matt…. Snap out of it! Help your friend!”
Steve barked
“What?!?” I said quickly.
“Get him hard…. Jesus. Just jerk him off … hell… jon will tell you. I’ve jerked bin off before.” Steve said looking over at Jon “right?”
“Yes” jon blushed. “We we’re experimenting” he continued.
“Nah. I wanted to touch that beast, plain and simple” Steve said. “But that’s where it ended”. Steve looked at the ground
I slowly moved to Jon‘s side and reached out and touched his cock. It instantly began to swell and harden.
“Oh my” i exclaimed as my hand filled with his heavy meat. I began to stroke him.
“Hahaha yeah” Jon blushed more but then moaned slightly
“Finally. Jesus” Steve sneered. “See. He’s huge right?” Steve asked me
“Yeah he is” I groaned, and I felt his cock throb in my hand. He was easily 8” and it was so thick.
“I told you, you’d never take it” Steve ridiculed me
“Oh. I think I could… maybe” I said and winked only to Jon and smiled
“There ain’t no way baby, he’s too big and you’re so damn tight” Steve laughed. I was still staring at Jon and he smiled and winked back.
“I could take him….” I retorted clearly getting irritated…. And horny
“Then fuck him Jon….” Steve ordered. “Prove to Matt he can’t take that beast”.
“I know I couldn’t” Steve sighed. Jon shot him a glance….
“What?” I asked.
“Yeah. I tried. I could barely take the tip it felt like he was trying to park a bus inside my ass” he sighed again.
“Steve…. You said you didn’t like to get fucked”. I said staring at him.
“I don’t. That’s the day I found that out” he looked at me.
“Oooohhhh…” I said. A little shocked by what I’ve learned about my friends. Steve had never been interested in bottoming.
“Anyway. Fuck him Jon” Steve sneered laughing.
“Dude… he’s your boyfrien…… oh Jesus Matt” Jon moaned as I continued to stroke him.
“It’s ok. He wants to try” Steve said “let him try”
Jon’s cock throbbed in my hand “Dude…. This is weird” he groaned and looked at me
“I don’t even know what to say” I said
“Try it Matt… really. Try it” Steve said smiling. “It’s fine. I’m ok with it”.
“I’ll admit. I’d love to try and I know you want to try bareback!” I laughed nervously blushing
“Fuck…..” Jon sat up “I don’t know”
“Look… I’ll go find lube”. Steve said standing up.
“Why?…..” Jon said startled
“Dude. He’s not a woman. It won’t get wet itself. You’ll kill him otherwise” Steve snorted and left the room….
“Dude. What the hell” Jon stared at me…. “Are you ok with this?”
“Me?” I asked?
“Yes” Jon moaned as I gripped his cock and stroked him slowly.
“Yes. I’m ok with this. You’re my friend and I want to pleasure you” i stood. And undressed as Steve walked in with a large bottle of lube.
“How do you want to do this Jon?” I asked smiling at him.
“Uhm. Well. I love missionary. I love to look into my woman’s eyes as I enter her” Jon smiled and looked down.
“Ok…. That hot..” I smiled and laid down on the couch “come on” I winked at him
Steve handed him the bottle as Jon stood.
“Dude. Are you sure? We can stop all of this.. he’s your partner man” He said.
“Last chance Steve, once he’s close to me. I’m not going to stop him” I said to Steve too.
“Oh. You’ll stop him. You won’t be able to handle it… but I’m ok with it. You’re both my friends and this is hot as hell to be honest. Besides. You’re going to quit faster than me” he laughed and sneered at me.
“Ok” Jon and I said in unison again
He got between my legs.
“Steve?” We both looked at Steve and said together
“It’s fine guys. Seriously”
I watched Jon coat his hand in lube and stroke his huge dick. To be honest. I’ve never seen a cock so hard.
“Well… this is the point of no return” Jon said as he pulled me closer to him and he leaned over me….. my eyes flew open as I felt his steel pole slide between my asscheeks and press against my little asshole. Instantly it was obvious he was much larger than Steve and this was going to get interesting quickly.
He leaned fully over me and whispered in my ear so Steve couldn’t hear
“I’ve wanted this since the day Steve introduced you to me” he nibbled my earlobe as I felt his arms wrap under my knees and pull my legs up around him and he pushed his enormous monster against my small hole. I looked down at his massive cock throbbing.
“Oh fuck Jon” I moaned. My body relaxed and completely submitted to him. I was breathing hard. I looked over at Steve…..
He leaned up holding my legs and hips “Look at me” Jon said
I quickly turned and stared into his intense eyes, he winked and then felt him push harder. My jaw dropped and I gasped loudly as I felt my ass surrender and his monster began its invasion. My hands flew up and pushed against his stomach.
“OH GOD JON” I yelled and my hands pushed against him. Involuntarily trying to resist him. My mind wanted him. My body was thinking it was a bad idea. My ass muscles were screaming.
“JON!! JESUS!!” I felt the head of his cock fully enter me. My straining asshole stretched around his shaft as he continued to push into me.
“AAAAAAAAHHHHH. AAAHHHHH” I screamed “FUUUCCCKKK!” I scooted away from his massive tool, but he continued to apply pressure to my ass
“I told you you couldn’t handle it” Steve laughed but he was jerking off in the chair. I stared at him as it felt like my ass was on fire.
Jon reached up and gently turned my face back to his. “Look…at…..me” he said softly his huge dick still slipping deeper and deeper. My mouth was wide open in the position of a scream but nothing came out.
“FUUCCK…J..JONNNN!!!l” finally escaped my brain and mouth.
“Jesus… you are tight as fuck, Matty” Jon moaned softly and smiled at me… that was his name for me when we play flirted. This time it had a lot more meaning on his breath. “You feel so good” he groaned
One of my hands pushed against his abs as the other dug into them. He leaned over me and kissed my neck as half of his cock had entered me. I wrapped my arms around his back and clawed at him.
“AAAAAHH Jon!” I yelled more. “You’re fucking huge you’re stretching me so much!!!”
“Hahaha I told you” Steve laughed. Still fapping in the chair.
“Shut up Steve. Matty will take me. He wants it. Don’t you Matty?” Jon smiled at me.
“Uugghh!!!” I groaned “I’m sorry Steve” “Yesss!!! yesss I want it “ I gasped “I want you”
“I meant what I said….” He whispered. “I’ve wanted you since we met”
“Oh Fuck Jon” I moaned in his ear
he pushed hard and buried his entire dick inside me, he pulled me closer smashing me into the cushions and rotated his hips as he grinded his throbbing head deep inside me
“Uuuughhnnnnnn AAAAAAAHHH i gruntled at screaming decibels and then screamed as pain, pleasure, lust, and admiration all collided together. I dug my fingers into his ass pulling him deeper into me. I stared at him. His eyes. His face. His body. My best friend was inside me. Stretching me beyond comprehension. I’ve never felt pain and pleasure combined together. It hurt yet I wanted and needed more of him.
“Jesus Jon, you’re splitting me apart” I groaned and panted. “I’m so stretched out around you….. you’re fucking massive”.
“You’re so fucking tight babe” he moaned in my ear. “I’m going to fuck you now” and he pulled me closer and kissed me as he raised his hips, pulling his cock out and then pushing it deep inside me again. Then he began to work it in and out of me.
“Oh god uugghh. Oh fuck uuuuggn. Fuckuuugnn oh god jon” I moaned as his cock seemed to Stretch me more with each thrust.
“Ok guys. He proved he can take it”. Steve suddenly stood near us. His cock dripping cum and going limp. He clearly gotten off and his head was clearing an realized what was happening.
I just stared at him as Jon ignored him completely and began to pick up his pace and truly began to fuck me.
My mouth opened wide and my eyes rolled back as Jon’s monster cock turned pain into insane pleasure as an orgasm rocked through me…
“I’m sorry” is all I could say to Steve as I arched under Jon and cum erupted against his stomach. “Oh my god Jon uuuuuugggh” I grunted and He began to slam against me plowing his cock deep inside me. I looked back at Steve again.
“It’s ok” he mouthed and turned and left the room.
“Your tight little ass was made for me baby” Jon moaned as I writhed under him. He kissed me and I kissed him hard in return.
“Oh God Jon” i moaned in his ear as he fucked me. We kissed and hugged and moved against each other as he made love to me.
“I’m going to cum” he groaned As he began to pick up pace and thrust harder into me. My hands moved to his sides and I looked down between our bodies and watches his long fat cock pumping in and out of me. I watched him fuck me as I felt him getting closer.
“Im going to cum Matty” he groaned again “your tight little ass is going to make me cum”.
“Cum inside me Jon. I want to feel you fill me” I grunted with my head against his shoulder under him as I continued to watch his tool stretch me out.
“I’m cumming” he grunted loudly and slammed into me. I felt his body shudder above me and felt his cock throb and then another orgasm hit me out go nowhere.
“Ugh ooo oh Oh fuck Jon” I yelped into his neck as I threw my head back and arched as we both came… I felt his hot seed splashing against my sore stretch walls as my cock sent cum over both of our stomachs and chests. We may writhing together and moaning as both of us settled down.
He kissed me again.
“I told you I wanted that” he smiled As he sat back on his legs. His cock popped out and bounced between my legs. Cum dripping off the tip.
“Oh my God Jon…. That was incredible” I said softly I laid my head back and closed my eyes. I felt his cum dripping from my ass
We looked at each other and simultaneously said
“So…. Now what?”
We’d been sitting here watching tV for a few hours. And we decided to put on some porn. We even joked about Steve and I putting on a show for Jon. But he declined enthusiastically confirming over and over he was straight.
After a while. He began to complain about how his girlfriend, his first serious girlfriend ever and the only woman he had ever been with refused to let him go bareback. She was worried mostly about having a baby and also STDs. They had sex a lot. But he always had to wear a condom
Now. I’m over 10 years older than both of them at the ripe age of 35.
“Awe” I laughed.
“Seriously. I just want to know what it feels like man” Jon groaned.
“It feels great” I sneered.
“Yeah it fucking does” Steve said laughing playfully. Especially fucking Matt’s tight ass”
“Why thank you” I winked and smiled.
“You fuck him BAREBACK, Steve?” Jon asked…
“Uh yeah…. MY man gets to ride Bareback I ain’t gonna get pregnant and we were both our firsts” I smiled and winked at Jon this time.
“Fuuucckk” he groaned. “Lucky dick” he snorted.
“Yes it is” I laughed.
“Yeah. I am lucky” Steve said and winked at me
“You should let me……” Jon said “hahah I’m kidding “ he quickly added
“Anytime baby” I flirted but was kidding, kind of
“Yeah. You should….. “ Steve said
My head whipped around at Steve “WHAT?” I said startled
“He’s my friend and your best friend. Of course you should let him” Steve laughed…. Then went silent.
“Guys. I’m fucking around. I know it can’t happen. He’s fucking huge and you’re ass is the tightest I’ve ever seen” Steve finally said
“Oohhh Hahahaa “ Jon and I replied in unison
But. My mind was spinning… I’d never seen his cock. Is he that big? Steve was big, but he thinks Jon is HUGE….. I’ll admit. My interest was triggered.
“How big?” I asked
“He’s really big Matt… you can’t handle it” Steve said snarky
“What the hell man..” I said irritated. “I can take it. Eventually… you act like he’s too much man for me!”
“Guys…. It’s all a joke” Jon laughed nervously
“Fuck it… show him Jon” Steve said.
“What?” Jon said staring between me and Steve. “Dude. Y’all in a relationship”
“It’s ok Jon. Show him” Steve said smiling. “We are all friends and I’ve seen it already.”
“Uhm……. Well… ok” Jon undid his button on his jeans and unzipped them. He fished out a long thick FLACCID dick….
“Dude. What the hell? You’re not even hard?” Steve ribbed him. “Matt can’t tell how big you are like that!”
“Looks pretty big to me” I said softly watching Jon look up at me… he smiled and I swear I saw his cock begin to get erect.
“Dude. Why aren’t you hard?” Steve said.
“I’m sorry! This is a little awkward!!” Jon yelled laughing.
“Matt…. Snap out of it! Help your friend!”
Steve barked
“What?!?” I said quickly.
“Get him hard…. Jesus. Just jerk him off … hell… jon will tell you. I’ve jerked bin off before.” Steve said looking over at Jon “right?”
“Yes” jon blushed. “We we’re experimenting” he continued.
“Nah. I wanted to touch that beast, plain and simple” Steve said. “But that’s where it ended”. Steve looked at the ground
I slowly moved to Jon‘s side and reached out and touched his cock. It instantly began to swell and harden.
“Oh my” i exclaimed as my hand filled with his heavy meat. I began to stroke him.
“Hahaha yeah” Jon blushed more but then moaned slightly
“Finally. Jesus” Steve sneered. “See. He’s huge right?” Steve asked me
“Yeah he is” I groaned, and I felt his cock throb in my hand. He was easily 8” and it was so thick.
“I told you, you’d never take it” Steve ridiculed me
“Oh. I think I could… maybe” I said and winked only to Jon and smiled
“There ain’t no way baby, he’s too big and you’re so damn tight” Steve laughed. I was still staring at Jon and he smiled and winked back.
“I could take him….” I retorted clearly getting irritated…. And horny
“Then fuck him Jon….” Steve ordered. “Prove to Matt he can’t take that beast”.
“I know I couldn’t” Steve sighed. Jon shot him a glance….
“What?” I asked.
“Yeah. I tried. I could barely take the tip it felt like he was trying to park a bus inside my ass” he sighed again.
“Steve…. You said you didn’t like to get fucked”. I said staring at him.
“I don’t. That’s the day I found that out” he looked at me.
“Oooohhhh…” I said. A little shocked by what I’ve learned about my friends. Steve had never been interested in bottoming.
“Anyway. Fuck him Jon” Steve sneered laughing.
“Dude… he’s your boyfrien…… oh Jesus Matt” Jon moaned as I continued to stroke him.
“It’s ok. He wants to try” Steve said “let him try”
Jon’s cock throbbed in my hand “Dude…. This is weird” he groaned and looked at me
“I don’t even know what to say” I said
“Try it Matt… really. Try it” Steve said smiling. “It’s fine. I’m ok with it”.
“I’ll admit. I’d love to try and I know you want to try bareback!” I laughed nervously blushing
“Fuck…..” Jon sat up “I don’t know”
“Look… I’ll go find lube”. Steve said standing up.
“Why?…..” Jon said startled
“Dude. He’s not a woman. It won’t get wet itself. You’ll kill him otherwise” Steve snorted and left the room….
“Dude. What the hell” Jon stared at me…. “Are you ok with this?”
“Me?” I asked?
“Yes” Jon moaned as I gripped his cock and stroked him slowly.
“Yes. I’m ok with this. You’re my friend and I want to pleasure you” i stood. And undressed as Steve walked in with a large bottle of lube.
“How do you want to do this Jon?” I asked smiling at him.
“Uhm. Well. I love missionary. I love to look into my woman’s eyes as I enter her” Jon smiled and looked down.
“Ok…. That hot..” I smiled and laid down on the couch “come on” I winked at him
Steve handed him the bottle as Jon stood.
“Dude. Are you sure? We can stop all of this.. he’s your partner man” He said.
“Last chance Steve, once he’s close to me. I’m not going to stop him” I said to Steve too.
“Oh. You’ll stop him. You won’t be able to handle it… but I’m ok with it. You’re both my friends and this is hot as hell to be honest. Besides. You’re going to quit faster than me” he laughed and sneered at me.
“Ok” Jon and I said in unison again
He got between my legs.
“Steve?” We both looked at Steve and said together
“It’s fine guys. Seriously”
I watched Jon coat his hand in lube and stroke his huge dick. To be honest. I’ve never seen a cock so hard.
“Well… this is the point of no return” Jon said as he pulled me closer to him and he leaned over me….. my eyes flew open as I felt his steel pole slide between my asscheeks and press against my little asshole. Instantly it was obvious he was much larger than Steve and this was going to get interesting quickly.
He leaned fully over me and whispered in my ear so Steve couldn’t hear
“I’ve wanted this since the day Steve introduced you to me” he nibbled my earlobe as I felt his arms wrap under my knees and pull my legs up around him and he pushed his enormous monster against my small hole. I looked down at his massive cock throbbing.
“Oh fuck Jon” I moaned. My body relaxed and completely submitted to him. I was breathing hard. I looked over at Steve…..
He leaned up holding my legs and hips “Look at me” Jon said
I quickly turned and stared into his intense eyes, he winked and then felt him push harder. My jaw dropped and I gasped loudly as I felt my ass surrender and his monster began its invasion. My hands flew up and pushed against his stomach.
“OH GOD JON” I yelled and my hands pushed against him. Involuntarily trying to resist him. My mind wanted him. My body was thinking it was a bad idea. My ass muscles were screaming.
“JON!! JESUS!!” I felt the head of his cock fully enter me. My straining asshole stretched around his shaft as he continued to push into me.
“AAAAAAAAHHHHH. AAAHHHHH” I screamed “FUUUCCCKKK!” I scooted away from his massive tool, but he continued to apply pressure to my ass
“I told you you couldn’t handle it” Steve laughed but he was jerking off in the chair. I stared at him as it felt like my ass was on fire.
Jon reached up and gently turned my face back to his. “Look…at…..me” he said softly his huge dick still slipping deeper and deeper. My mouth was wide open in the position of a scream but nothing came out.
“FUUCCK…J..JONNNN!!!l” finally escaped my brain and mouth.
“Jesus… you are tight as fuck, Matty” Jon moaned softly and smiled at me… that was his name for me when we play flirted. This time it had a lot more meaning on his breath. “You feel so good” he groaned
One of my hands pushed against his abs as the other dug into them. He leaned over me and kissed my neck as half of his cock had entered me. I wrapped my arms around his back and clawed at him.
“AAAAAHH Jon!” I yelled more. “You’re fucking huge you’re stretching me so much!!!”
“Hahaha I told you” Steve laughed. Still fapping in the chair.
“Shut up Steve. Matty will take me. He wants it. Don’t you Matty?” Jon smiled at me.
“Uugghh!!!” I groaned “I’m sorry Steve” “Yesss!!! yesss I want it “ I gasped “I want you”
“I meant what I said….” He whispered. “I’ve wanted you since we met”
“Oh Fuck Jon” I moaned in his ear
he pushed hard and buried his entire dick inside me, he pulled me closer smashing me into the cushions and rotated his hips as he grinded his throbbing head deep inside me
“Uuuughhnnnnnn AAAAAAAHHH i gruntled at screaming decibels and then screamed as pain, pleasure, lust, and admiration all collided together. I dug my fingers into his ass pulling him deeper into me. I stared at him. His eyes. His face. His body. My best friend was inside me. Stretching me beyond comprehension. I’ve never felt pain and pleasure combined together. It hurt yet I wanted and needed more of him.
“Jesus Jon, you’re splitting me apart” I groaned and panted. “I’m so stretched out around you….. you’re fucking massive”.
“You’re so fucking tight babe” he moaned in my ear. “I’m going to fuck you now” and he pulled me closer and kissed me as he raised his hips, pulling his cock out and then pushing it deep inside me again. Then he began to work it in and out of me.
“Oh god uugghh. Oh fuck uuuuggn. Fuckuuugnn oh god jon” I moaned as his cock seemed to Stretch me more with each thrust.
“Ok guys. He proved he can take it”. Steve suddenly stood near us. His cock dripping cum and going limp. He clearly gotten off and his head was clearing an realized what was happening.
I just stared at him as Jon ignored him completely and began to pick up his pace and truly began to fuck me.
My mouth opened wide and my eyes rolled back as Jon’s monster cock turned pain into insane pleasure as an orgasm rocked through me…
“I’m sorry” is all I could say to Steve as I arched under Jon and cum erupted against his stomach. “Oh my god Jon uuuuuugggh” I grunted and He began to slam against me plowing his cock deep inside me. I looked back at Steve again.
“It’s ok” he mouthed and turned and left the room.
“Your tight little ass was made for me baby” Jon moaned as I writhed under him. He kissed me and I kissed him hard in return.
“Oh God Jon” i moaned in his ear as he fucked me. We kissed and hugged and moved against each other as he made love to me.
“I’m going to cum” he groaned As he began to pick up pace and thrust harder into me. My hands moved to his sides and I looked down between our bodies and watches his long fat cock pumping in and out of me. I watched him fuck me as I felt him getting closer.
“Im going to cum Matty” he groaned again “your tight little ass is going to make me cum”.
“Cum inside me Jon. I want to feel you fill me” I grunted with my head against his shoulder under him as I continued to watch his tool stretch me out.
“I’m cumming” he grunted loudly and slammed into me. I felt his body shudder above me and felt his cock throb and then another orgasm hit me out go nowhere.
“Ugh ooo oh Oh fuck Jon” I yelped into his neck as I threw my head back and arched as we both came… I felt his hot seed splashing against my sore stretch walls as my cock sent cum over both of our stomachs and chests. We may writhing together and moaning as both of us settled down.
He kissed me again.
“I told you I wanted that” he smiled As he sat back on his legs. His cock popped out and bounced between my legs. Cum dripping off the tip.
“Oh my God Jon…. That was incredible” I said softly I laid my head back and closed my eyes. I felt his cum dripping from my ass
We looked at each other and simultaneously said
“So…. Now what?”
