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This is the 4th installment of my story, “My First Gay Experience” which is also posted here. I’m posting it separately since this and the 3rd installment go beyond the title of the original posting and might not attract an interested audience based on the title. As background, Jim and I were college roommates in the late 1960’s, a very different time to be gay than today. This chapter describes our first time barebacking.
Jim and I happily settled into our sexual relationship. I mostly topped Jim, he occasionally me. We had given up using condoms and were confident being able to bareback with no concern, since we were both monagamous and hadn’t other sexual contacts. Still, I vividly remember the very first time I barebacked Jim.
Back in the late ‘60s, the availability and types of condoms were very different from today. They were kept behind the counter at pharmacies, and it was always embarrassing to have to ask for them. They came either lubricated or not, and the latex used was thicker than that today. It was a “one size fits all” situation, and this was a problem for me. My dick is thick; its shaft is about 6” around, and condoms were typically sized for the “average” dick, about 4.5” around. Condoms then always fit me very tightly, and I felt it. My glans flares outward at its rim, making my diameter there greater than that of my shaft. When I wore a condom, I felt the constriction all along my shaft. Worse, the pressure at the end pressed down on my glans and compressed it, virtually squashing it against my shaft. The outward flare, which gave me such pleasure when I stroked it when I masturbated, was gone, and my glans lost most of its hardness. The only time that wearing a condom was comfortable and remotely pleasurable was when my precum filled its end and some of the pressure against my glans was lessened as my shaft could move freely in the now lubricated end.
Jim and seriously discussed whether it would be OK to bareback, and we were both OK with it. I looked forward with eager anticipation the next time we would have sex. That night finally came, and after our usual foreplay, I was harder than ever before. I’ve always been a precum gusher, and sometimes to the point of embarrassment if I wet through my pants if I were ogling another guy. I caressed Jim’s hole with the end of my penis, letting the precum drip out and lubing the area well. I sopped up some of my precum onto onto my finger and slowly inserted it into Jim. He let out a soft moan as I pushed in and out and ran circles around his relaxing hole. Jim then sat up, bent over and gave me a blow job I’ll never forget, deep throating me and throughly wetting my cock from base to tip with his saliva. I reached down below my balls and pushed inward against my taint and then slowly up under my sac and up my shaft, collecting the drops of precum that dripped out onto my fingers which I then pushed into Jim, lubricating his inside all the more. I repeated this again, this time rubbing the collected precum down along my rock hard erection.
Jim was now on his back, his knees lifted in the air. I leaned over him and lightly touched the tip of my penis against his hole. I could feel his skin directly against the tip of my penis, and the feeling was exhilarating. I pushed inward in a slow, steady movement, letting Jim relax so that he could take me in. Penetration was more difficult than it had ever been before since my glans, unrestricted and not compressed by a tight condom, was at his full hardness, its outer rim flared outward. Jim was OK as I pushed inward until I could just feel the flare at the ridge of my corona up against the opening of his anus. I felt a resistance to pushing further inward, and Jim motioned to me to stop moving. After a moment, I pulled out and let my precum drip onto his hole. Jim gave me a nod, wanting me to continue, so I pushed slowly inward, until I felt again the resistance against my corona, but this time I kept going. Jim had a look of discomfort on his face but didn’t motion me to stop. Suddenly, almost with a pop, his anus opened up completely and I was able to thrust inside him.
The look of discomfort on Jim’s face immediately switched to one of contentment, and he whispered, “Come all the way inside me.” I did and experienced the most sensual, satisfying moment of my life up till then. With no tight condom between me and Jim, the skin of my penis was grasped tightly by Jim’s insides. I could feel every fold and ridge inside his rectum as I slowly thrust in and out. Jim was delirious in a way he never was when I wore a condom, I suspect because my glans was full, and the edge of my corona caressed his inside, something he never felt before. My thrusting movements became easier and more fluid as my precum kept oozing out, and I was able to thrust easier and easier, faster and faster. Suddenly, I felt that I was going to cum, and I didn’t hold back. My thrusts almost became spastic, and suddenly I exploded like never before. I pushed myself deep inside and held myself there as my penis spurted and spurted over and over again. Jim was delirious. His arms grasped me around my back, and he pulled me closer and closer while he pushed his groin upward against me. We literally had never been closer than at this moment, and we both knew that we would never experience this first-time feeling ever again.
Normally, when I come, my sexual energy quickly fades, my erection fades, and I feel exhausted. Not now. While Jim’s insides held my penis tight, I could now move inside him with virtually no friction at all, my penis washed by the sea of my cum. My erection held fast and did not fade at all. I continued thrusting, just enjoying the feeling but without the anticipation of cumming. At times, I would stop, push myself deep inside, pull Jim close to me and give him the deepest kisses imaginable, before I would begin thrusting again. Soon, the feelings along my erection changed, from merely pleasurable to becoming more and more sexually charged. I sped up my thrusts and suddenly felt the anticipation of cumming again. I couldn’t believe it. I had never come twice so quickly before. Jim felt it too, and urged me on with a chorus of, “Yes, yes, yes.” I was screaming out, “Fuck, fuck, fuck,” over and over until I orgasmed again. The feeling was so different from my first orgasm. I had already spent most of my cum, so while my erection jerked and jerked, I couldn’t feel the sensation of cum pouring out of me. Inside, I experienced a much stronger, whole body orgasm. Every muscle in me contracted, some of them undergoing uncontrollable spasms, and this continued longer than my first orgasm. Completely spent, I collapsed, my full weight on Jim’s body.
After a minute or so, I lifted myself up and slowly pulled myself from Jim. I sat up on my knees and watched with fascination as my cum began to dribble from him. I scooped up as much as I could onto the palm of my hand and then stroked Jim’s dick with it. The warmth and slipperiness of my cum caused Jim to gasp, and I was able to stroke him effortlessly. Jim was delirious, and his erection swelled and throbbed in my hand. Soon his glans completely popped out of his foreskin and turned a deep, blood red purple. His body suddenly shook, and he shot his load up across his chest before he collapsed. I reached up with my own cummy hand and rubbed our loads together.
That night was an experience of a lifetime. We barebacked from that night on and never used a condom again.
Jim and I happily settled into our sexual relationship. I mostly topped Jim, he occasionally me. We had given up using condoms and were confident being able to bareback with no concern, since we were both monagamous and hadn’t other sexual contacts. Still, I vividly remember the very first time I barebacked Jim.
Back in the late ‘60s, the availability and types of condoms were very different from today. They were kept behind the counter at pharmacies, and it was always embarrassing to have to ask for them. They came either lubricated or not, and the latex used was thicker than that today. It was a “one size fits all” situation, and this was a problem for me. My dick is thick; its shaft is about 6” around, and condoms were typically sized for the “average” dick, about 4.5” around. Condoms then always fit me very tightly, and I felt it. My glans flares outward at its rim, making my diameter there greater than that of my shaft. When I wore a condom, I felt the constriction all along my shaft. Worse, the pressure at the end pressed down on my glans and compressed it, virtually squashing it against my shaft. The outward flare, which gave me such pleasure when I stroked it when I masturbated, was gone, and my glans lost most of its hardness. The only time that wearing a condom was comfortable and remotely pleasurable was when my precum filled its end and some of the pressure against my glans was lessened as my shaft could move freely in the now lubricated end.
Jim and seriously discussed whether it would be OK to bareback, and we were both OK with it. I looked forward with eager anticipation the next time we would have sex. That night finally came, and after our usual foreplay, I was harder than ever before. I’ve always been a precum gusher, and sometimes to the point of embarrassment if I wet through my pants if I were ogling another guy. I caressed Jim’s hole with the end of my penis, letting the precum drip out and lubing the area well. I sopped up some of my precum onto onto my finger and slowly inserted it into Jim. He let out a soft moan as I pushed in and out and ran circles around his relaxing hole. Jim then sat up, bent over and gave me a blow job I’ll never forget, deep throating me and throughly wetting my cock from base to tip with his saliva. I reached down below my balls and pushed inward against my taint and then slowly up under my sac and up my shaft, collecting the drops of precum that dripped out onto my fingers which I then pushed into Jim, lubricating his inside all the more. I repeated this again, this time rubbing the collected precum down along my rock hard erection.
Jim was now on his back, his knees lifted in the air. I leaned over him and lightly touched the tip of my penis against his hole. I could feel his skin directly against the tip of my penis, and the feeling was exhilarating. I pushed inward in a slow, steady movement, letting Jim relax so that he could take me in. Penetration was more difficult than it had ever been before since my glans, unrestricted and not compressed by a tight condom, was at his full hardness, its outer rim flared outward. Jim was OK as I pushed inward until I could just feel the flare at the ridge of my corona up against the opening of his anus. I felt a resistance to pushing further inward, and Jim motioned to me to stop moving. After a moment, I pulled out and let my precum drip onto his hole. Jim gave me a nod, wanting me to continue, so I pushed slowly inward, until I felt again the resistance against my corona, but this time I kept going. Jim had a look of discomfort on his face but didn’t motion me to stop. Suddenly, almost with a pop, his anus opened up completely and I was able to thrust inside him.
The look of discomfort on Jim’s face immediately switched to one of contentment, and he whispered, “Come all the way inside me.” I did and experienced the most sensual, satisfying moment of my life up till then. With no tight condom between me and Jim, the skin of my penis was grasped tightly by Jim’s insides. I could feel every fold and ridge inside his rectum as I slowly thrust in and out. Jim was delirious in a way he never was when I wore a condom, I suspect because my glans was full, and the edge of my corona caressed his inside, something he never felt before. My thrusting movements became easier and more fluid as my precum kept oozing out, and I was able to thrust easier and easier, faster and faster. Suddenly, I felt that I was going to cum, and I didn’t hold back. My thrusts almost became spastic, and suddenly I exploded like never before. I pushed myself deep inside and held myself there as my penis spurted and spurted over and over again. Jim was delirious. His arms grasped me around my back, and he pulled me closer and closer while he pushed his groin upward against me. We literally had never been closer than at this moment, and we both knew that we would never experience this first-time feeling ever again.
Normally, when I come, my sexual energy quickly fades, my erection fades, and I feel exhausted. Not now. While Jim’s insides held my penis tight, I could now move inside him with virtually no friction at all, my penis washed by the sea of my cum. My erection held fast and did not fade at all. I continued thrusting, just enjoying the feeling but without the anticipation of cumming. At times, I would stop, push myself deep inside, pull Jim close to me and give him the deepest kisses imaginable, before I would begin thrusting again. Soon, the feelings along my erection changed, from merely pleasurable to becoming more and more sexually charged. I sped up my thrusts and suddenly felt the anticipation of cumming again. I couldn’t believe it. I had never come twice so quickly before. Jim felt it too, and urged me on with a chorus of, “Yes, yes, yes.” I was screaming out, “Fuck, fuck, fuck,” over and over until I orgasmed again. The feeling was so different from my first orgasm. I had already spent most of my cum, so while my erection jerked and jerked, I couldn’t feel the sensation of cum pouring out of me. Inside, I experienced a much stronger, whole body orgasm. Every muscle in me contracted, some of them undergoing uncontrollable spasms, and this continued longer than my first orgasm. Completely spent, I collapsed, my full weight on Jim’s body.
After a minute or so, I lifted myself up and slowly pulled myself from Jim. I sat up on my knees and watched with fascination as my cum began to dribble from him. I scooped up as much as I could onto the palm of my hand and then stroked Jim’s dick with it. The warmth and slipperiness of my cum caused Jim to gasp, and I was able to stroke him effortlessly. Jim was delirious, and his erection swelled and throbbed in my hand. Soon his glans completely popped out of his foreskin and turned a deep, blood red purple. His body suddenly shook, and he shot his load up across his chest before he collapsed. I reached up with my own cummy hand and rubbed our loads together.
That night was an experience of a lifetime. We barebacked from that night on and never used a condom again.
