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Gay Stories
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Bi-Sexual Male / 40
Best Friend With Benefits
Around 10 years ago after my divorce I went on a dating site. I dated different women but nothing clicked until I met Rachel. She is a full figured open minded bubbly gal who was 40 and divorced like me when I met her while I was a decade younger. We became very close very quickly and best friends. Sexually she loves receiving oral and then masturbating me but most of all she prefers cuddling and kissing. We moved in together and got to know everything about each other. One night she surprised me by putting on some gay porn then teasing me mercilessly when I got aroused seeing the hard cocks and gay sex. She laughed and said "You are bi curious babe as I have never seen your cock that stiff". From this she encouraged me to explore this further so she could watch me find out what it feels like.
Rather than bring in some random stranger Rachel suggested she contact an older gay friend she knew to see if he was game for it. He was willing I found out a few weeks later and she finally convinced me to try it with him.
The day arrived and to surprise me she had not described him at all so all I knew was that he was older than her. We had wine ready and Eugene arrived. He was pushing 60 tall and slim with a trimmed moustache and receding silver hair. He had a softer more animated look like a lot of older gay men. He looked more relaxed than I expected while I was nervous. Rachel excitedly poured us wine and went into the kitchen to get some snacks ready. We ate and had a few glasses of wine while getting a bit tipsy. Rachel led us into the bedroom and had us all get undressed. I noticed Eugene had a decent size cock which was semi hard which soon made my cock hard as a rock looking at it. Rachel asked me to go down on her which I did. Before she could climax she said "Your turn babe" and got up and sat on a nearby chair with her legs spread. Rachel asked me to lay back and Eugene sprang into action. His hands and mouth explored my body then he gobbled up my hard cock. I had not been blown in a year or 2 as Rachel was not into sucking so this felt amazing. Eugene was also very very good at it. He made me blow my load in 5 minutes as I could see Rachel furiously masturbating in the chair to a shuddering climax. Eugene lay back and I lay in a state of release beside him. The 3 of us chatted for awhile then Rachel encouraged me to suck Eugene's cock. I took his cock in my mouth and it stiffened noticeably. I started sucking him realizing I loved how his cock fit my mouth and his arousal. He took awhile to cum but by that point I felt kind of slutty and sexy sucking him and desperately wanted to taste his load. He filled my mouth as I heard Rachel have another loud orgasm. At this point all the tension and inhibition was gone. We had some snacks and another glass of wine. Rachel looked happy and sleepy. She asked me if I would sleep in the other bedroom with Eugene tonight. Eugene's eyes lit up and he quickly guided me there both of us still naked. In the bed Eugene whispered to me he like Rachel loves kissing and cuddling too. This felt more intimate and actually scared me a bit. Making out with a gay man in bed all night felt like a bigger step in a strange way. But at this point inhibitions were gone so I gave in. Eugene slow kissed my mouth and fondled my chest. His moustsche felt sexy and tingly on my lips. I could feel a deeper arousal happening going beyond lust into affection and God knows what. I kissed him back intensely and we cuddled and kissed for a long time. It felt so different than when with Rachel. My cock was incredibly stiff by this point. There was some Vaseline on a dresser and Eugene coated Mt hard cock with it then surprised me by lowering himself onto my cock which easily slid into his ass. He rode me slow and deep until I was grabbing him tight to go deeper. I had the biggest orgasm of my life spraying my load inside of him explosively as his body shook all over. It was so mindblowing we just lay silently cuddling and slow kissing after. Then we fell asleep. Rachel in the morning was smiling as she brought us breakfast in bed. She seemed to know exactly what took place and kept teasing about us being made for each other. This night ked to many more nights like this. Eugene and I ended up in this bedroom every night he was over having sex. Rachel and I still slept together when he was not there. Then a couple years later Eugene moved in with us and while Rachel and I remained as close as ever Eugene and I became a full couple. Once or twice a week Rachel knocks on our door at night and I join her in bed to go down on her and kiss and cuddle. Eugene is totally fine with this as he says she has needs too.
Rather than bring in some random stranger Rachel suggested she contact an older gay friend she knew to see if he was game for it. He was willing I found out a few weeks later and she finally convinced me to try it with him.
The day arrived and to surprise me she had not described him at all so all I knew was that he was older than her. We had wine ready and Eugene arrived. He was pushing 60 tall and slim with a trimmed moustache and receding silver hair. He had a softer more animated look like a lot of older gay men. He looked more relaxed than I expected while I was nervous. Rachel excitedly poured us wine and went into the kitchen to get some snacks ready. We ate and had a few glasses of wine while getting a bit tipsy. Rachel led us into the bedroom and had us all get undressed. I noticed Eugene had a decent size cock which was semi hard which soon made my cock hard as a rock looking at it. Rachel asked me to go down on her which I did. Before she could climax she said "Your turn babe" and got up and sat on a nearby chair with her legs spread. Rachel asked me to lay back and Eugene sprang into action. His hands and mouth explored my body then he gobbled up my hard cock. I had not been blown in a year or 2 as Rachel was not into sucking so this felt amazing. Eugene was also very very good at it. He made me blow my load in 5 minutes as I could see Rachel furiously masturbating in the chair to a shuddering climax. Eugene lay back and I lay in a state of release beside him. The 3 of us chatted for awhile then Rachel encouraged me to suck Eugene's cock. I took his cock in my mouth and it stiffened noticeably. I started sucking him realizing I loved how his cock fit my mouth and his arousal. He took awhile to cum but by that point I felt kind of slutty and sexy sucking him and desperately wanted to taste his load. He filled my mouth as I heard Rachel have another loud orgasm. At this point all the tension and inhibition was gone. We had some snacks and another glass of wine. Rachel looked happy and sleepy. She asked me if I would sleep in the other bedroom with Eugene tonight. Eugene's eyes lit up and he quickly guided me there both of us still naked. In the bed Eugene whispered to me he like Rachel loves kissing and cuddling too. This felt more intimate and actually scared me a bit. Making out with a gay man in bed all night felt like a bigger step in a strange way. But at this point inhibitions were gone so I gave in. Eugene slow kissed my mouth and fondled my chest. His moustsche felt sexy and tingly on my lips. I could feel a deeper arousal happening going beyond lust into affection and God knows what. I kissed him back intensely and we cuddled and kissed for a long time. It felt so different than when with Rachel. My cock was incredibly stiff by this point. There was some Vaseline on a dresser and Eugene coated Mt hard cock with it then surprised me by lowering himself onto my cock which easily slid into his ass. He rode me slow and deep until I was grabbing him tight to go deeper. I had the biggest orgasm of my life spraying my load inside of him explosively as his body shook all over. It was so mindblowing we just lay silently cuddling and slow kissing after. Then we fell asleep. Rachel in the morning was smiling as she brought us breakfast in bed. She seemed to know exactly what took place and kept teasing about us being made for each other. This night ked to many more nights like this. Eugene and I ended up in this bedroom every night he was over having sex. Rachel and I still slept together when he was not there. Then a couple years later Eugene moved in with us and while Rachel and I remained as close as ever Eugene and I became a full couple. Once or twice a week Rachel knocks on our door at night and I join her in bed to go down on her and kiss and cuddle. Eugene is totally fine with this as he says she has needs too.
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