Mykell

My condom to bareback story.. Years ago my wife and I went to a swingers event that had a sex swing, it was before I really learned I was bi-sexual, she convinced me to get into it and she proceeded to fuck me with one of her dildos. I enjoyed it a lot but alas we never went back to that club. Fast forward to yesterday.. I was on Grindr and a guy named John started chatting with me by sending a few nice naked photos to me. One of John’s photos was him in a sling and it brought back old fond memories of that one time I used one. I asked John about the swing and he told me that he had it setup in his garage and was willing to “show me the ropes.” We decided to meet the next day. I went over to his place and he invited me in. We went to the garage and he showed me how to get into it. I was so turned on that as he was showing me, I began to undress. By the time he had pulled out the ankle cuffs and secured them to the swing, I was naked and hard as a rock. He guided me into the webbing and gently lowered me into it. First he secured one ankle to one side and worked his hand down my leg to linger at my ball sack. His cock was rigid, and I could actually see pre-cum dribbling down his cock shaft. Gently raking his nails over my balls, he then proceeded up my other leg. Once he connected the second ankle his face twitched an smile and he said “Now you're mine.” John proceeded to undress himself and once in awhile reach out and tease me by rubbing his fingers over my balls and rubbing my taint. His fingers felt like electricity as they made their way up to my chest. Then he worked some lube into my man pussy. I could feel his fingers as they slowly penetrated my hole. At first, just a finger could slide into my tight pussy but as he worked his magic he was able to get two fingers inside of me. With the two fingers inside, I started to twitch and thrash as waves of pleasure started to come from inside of me. I could feel him rubbing my prostrate and when he hit it just right, my cock jumped and got even harder. Feeling it was about time to have his cock in me, I took some of the lube and smeared it on his cock. As I rubbed it, I could feel his girth and mentally knew I was about to have a good time. I teased his cock against my pussy, slowly rubbing it the hair around my ass. I told John it was time and he needed to get a condom, I could feel how hard it was pressed against me. He slipped on the condom and I spread more lube over it and pulled him closer to me. I then guided his cock to my waiting hole and felt it begin to enter my tight pussy. John began to work slowly in and out with just the tip of his cock in me and I could feel my pussy opening up more every time. Finally he was able to fully mount my pussy and we began match rhythms of our bodies against the sling. At one point I felt him go a little soft and I tried to pick up the pace so he would not lose his erection. But he did. I tried to use my hand to get him hard but with the condom on, he was having trouble achieving an erection. So I looked into his eyes and slowly pulled the condom off. I again started to tease his cock against my ass and he started to harden. I tried slipping hte condom on but by the time I did he would become soft. So I took it off again, and whispered, just till you get hard again... I slide his cock to my waiting hole and felt his half hard cock pop into me. I just waited a sec to make sure he was in and then I started to thrust against him. After a couple of minutes I had him hard again and I felt my orgasm approaching. He said hold on while i slip a condom on and I grabbed him by hte waist. I said “DON’T Stop!” He then smiled and then began to thrust harder as a wave of pleasure rushed over me and I felt he cock twitch and explode in me. He held me against the swing as his body twitched and I felt his warmth spread in my pussy. We stayed locked for about a minute and then his cock started to recede. I felt an emptiness with his cock falling out of me. With my ass high up in the air, I did not feel his cum dribble out until he unhooked my legs and had me sit up.. Luckily he had placed a towel underneath me because his cum then ran out my enlarged pussy and onto the floor. I went to the shower and cleaned up knowing I had taken my 2nd bareback load in just a month..

So I have always played safe when fucking guys but the last time I played things changer... here is what happened. i am a bi male who has always bottomed for guys but I got the itch to top. I had been chatting with a guy for awhile on Grindr and we had been exchanging stories and how we got into fucking guys. He had a girlfriend that had convinced him to bottom for a cock and I had a wife who would let me play. He was looking for someone to fuck him and was ok with condoms. He sent me his address and I drove to his house. Feeling anxious and nervous about my first time topping a guy I Almost backed out and turned around. This was new territory for me, I had always been the bottom and luckily he opened the door as I was about to leave. He invited me in to his house and lead me to his bedroom. As I followed him I realized he was in his underwear and a t-shirt, I could see his bubble butt outlined and I instantly got hard walking down the hallway. Once we entered his bedroom he layed down on his back on the bed and proceeded to slowly wiggle out of his underwear. Still no words had been said, enough had been said by his actions and I began to strip, feeling my lust to fuck grow in my balls. He reached over to some coconut oil and began greasing himself as I finished stripping. I threw some condoms on the bed and I knew that I was going to fuck him. once undressed I crawled over him and laid on top of feeling his greased cock against my unlubed cock. He rubbed his hand along my cock and I realized he was lubing my cock with the coconut oil. I took my bare cock and slowly rubbed it up and around his cock and balls and slowly trailed it to his pussy. I allowed my cock to slide up and down his crack and my cock engorged more so than ever before. Knowing it was time to fuck his ass, I picked up a condom and slowly rolled it on. I never have had to wear a condom with my wife as she was on the pill and the feeling of being wrapped was an odd sensation to begin with. Luckily I stayed hard and then pointed my cock to his anus and slowly pushed it in. From our previous chats, I knew he was anal virgin for cocks, he had had some dildos in him, but this was his first time. I knew from experience that I would have to go slow and let him relax. After a couple mins of slowly working my tip into him I started to go soft. I realized I was not having enough sensation to stay hard and so I pulled my cock completely out and slipped off the condom. I slapped my cock on his balls and I could see he knew my problem, our eyes met and he nodded, I then slipped my bare cock into his ass for the first time and I became instantly hard. I had never felt such an sensation. His ass ring was so much more tight than I remembered from just a minute ago, but I knew he was more relaxed than before. I slipped my cock in deeper thinking that I would lossoen him up slip on the condom. I knew that being unwrapped was a risk but I wanted to fuck so badly. I figured once I got going i could slip one on and finish my load in him. He slowly opened up and I realized it was time to slip the condom on and that is when I realized that the condoms had been thrown off the bed and I could no longer reach them without stopping. I knew if I stopped I would be back in the same boat as before and so I kept going instead. The pace of our fucking picked up until I was furiously pounding at his hole and I felt the swell of my load churn inside. Finally I said my first words to him, ‘I am CUMMING!” and a second later I felt my orgasm hit and my load launch into his virginal hole. I pulsed a large load for a good minute experiencing one of the grestest orgasms I had ever had. I stayed in him until I felt myself softening and I kissed him on the lips as I finished pulling out. looking down I realized he too had came and I saw all his load layered between us. We both collapsed and laid back chatting about the experience. Now I am pretty sure I would never want to fuck wrapped again but I know I have to play safe...