That time I lost a bet and had to take a huge dick
Normally Iām more of a dominant top who loves making twinks squirm when I stretch their smooth asses open with my thick cock, but every now and then I get turned on thinking about this time back in college when I got a taste of my own medicine.
When I was 20, I had been going bowling with these three guys who were a few years older than me. Justin and Brad were a couple who I knew through a mutual friend, and the third one was this cute Latino guy Josh who I had not met until we started bowling. One night at the bowling alley, Justin approached me when I was about to bowl and casually mentioned that Josh said he thought I was cute and wanted to fuck me. Josh quit bowling early in the last game because he had gotten tired of playing, and this is a pet peeve of mine (I hate when my competitors wonāt take a game all the way), so I decided to give him some incentive. I sat down next to him and told him he could fuck me if he beat my score. He seemed intrigued and resumed playing after that. Unfortunately for me, he won the bet.
We all went back to Justin and Bradās apartment. They watched as Josh and I sat on the couch and started stripping for each other until we were in our boxers, and then Josh whipped out a dick the size of mine! I hadn't seen his dick before and mistakenly assumed he would be average when I agreed to the bet, but at this point I was sort of obligated to take it. We took a shower together and got clean, and then he had me put on one of Justinās jockstraps and pushed me down on the bed. He rimmed me and used a dildo on me for a little while to loosen me up. I was still pretty tight at that age, as I had only bottomed for one other guy and did not own any toys. When he was ready to fuck me, he pulled a condom out of the drawer and unrolled it over his thick, glistening rod. For some reason, watching a hung guy put on a condom right before heās about to top is a huge turn-on.
I tried sitting on his dick at first. It was kind of uncomfortable and felt like a lot of pressure with some slight burning when he first pushed it in. I went to grab my cock (I had never put anything in my ass without simultaneously stroking my cock before), but he told me not to touch it because he didnāt want me cumming too soon. It kind of hurt to ride him fast, so he wanted to fuck me doggie style so that I couldn't stop him from thrusting hard. It kind of "burned" from the pain of his girth continually mashing through my hole and up into my guts. He was really stuffing me hard, too. He was thrusting his cock all the way in me so that his hips were mashed against my ass cheeks and his balls were slapping against my taint. He was going so deep that I felt a pinch in my stomach when his huge dick met resistance at that 90-degree turn, and I could feel the head "pop" through each time he forced the last two inches in. The feeling of having my guts straightened out when he went balls-deep was making me squirm. Whenever I would lurch forward a little bit, he would just pull back on my shoulders and slam his pole all the way in, as if to punish me for running from it. With a toy I can control the depth and speed, and I can just stop for a second when itās getting too intense. But with getting fucked, he was in control, so I just had to grit my teeth, curl my toes, and endure it. He could tell I was struggling to take it, but that made him even hornier. Justin and Brad were rock hard, beating their dicks as they watched Josh fucking my ass like he owned it. He was definitely getting off on claiming his prize. At first I was hoping that he would hurry up and cum, but then I started getting turned on thinking about how this felt on his end, and feeling his cock thickening and pulsing inside me.
Just when I thought I couldnāt take anymore, I asked if we could change positions and do it missionary. I got on my back and he spread my legs and pushed his thick pole back inside me. It felt better this way because of the angle of his cock. I wrapped my legs around his waist and squeezed him between my thighs as he continued thrusting into me.
The last position we did was ass up/face down (my favorite as either the top or the bottom). This hurt a little more than missionary, but not quite as much as doggie. The way his thick cock filled me up and hit my prostate with each thrust was starting to make me feel like cumming. He was bouncing up and down on me pretty hard, his hips smacking my perked cheeks and his weight driving my pelvis into the bed each time his cock plunged into me. I wasnāt touching myself, but I felt more and more like I was going to cum with each thrust of his cock. Just as I was getting close, he came first. He pushed himself all the way inside me and squeezed my shoulders with his hands. I could feel his body tighten up and his cock throbbing with each spurt. Being more of a top, it really turned me on imagining what it felt like for him, what it was like being inside me. While it would have been hotter if I had cum hands free while he was fucking me, I still shot an enormous load when I finished by hand.
I was pretty sore afterwards, but it was the hot kind of sore that reminded me of his warm, thick pole stretching me to my limit. Each time I "squeezed" my kegels as I walked back to my dorm room at 4 AM, I could feel the warm lube still squishing in my hole and between my cheeks. This combined with the soreness of being recently fucked prompted me to beat off at least twice more that night.
A couple of other guys have topped me since then, but this was the first (and still one of the only) intense bottoming experiences I have ever had. I actually donāt reminisce about it much, being more of a top, but it gets me really hot when Iām in a rare submissive mood. Sometimes, I secretly fantasize about re-living the experience of losing a bet to a dominant top with a huge dick and being obligated to take it whether I can handle it or not.
When I was 20, I had been going bowling with these three guys who were a few years older than me. Justin and Brad were a couple who I knew through a mutual friend, and the third one was this cute Latino guy Josh who I had not met until we started bowling. One night at the bowling alley, Justin approached me when I was about to bowl and casually mentioned that Josh said he thought I was cute and wanted to fuck me. Josh quit bowling early in the last game because he had gotten tired of playing, and this is a pet peeve of mine (I hate when my competitors wonāt take a game all the way), so I decided to give him some incentive. I sat down next to him and told him he could fuck me if he beat my score. He seemed intrigued and resumed playing after that. Unfortunately for me, he won the bet.
We all went back to Justin and Bradās apartment. They watched as Josh and I sat on the couch and started stripping for each other until we were in our boxers, and then Josh whipped out a dick the size of mine! I hadn't seen his dick before and mistakenly assumed he would be average when I agreed to the bet, but at this point I was sort of obligated to take it. We took a shower together and got clean, and then he had me put on one of Justinās jockstraps and pushed me down on the bed. He rimmed me and used a dildo on me for a little while to loosen me up. I was still pretty tight at that age, as I had only bottomed for one other guy and did not own any toys. When he was ready to fuck me, he pulled a condom out of the drawer and unrolled it over his thick, glistening rod. For some reason, watching a hung guy put on a condom right before heās about to top is a huge turn-on.
I tried sitting on his dick at first. It was kind of uncomfortable and felt like a lot of pressure with some slight burning when he first pushed it in. I went to grab my cock (I had never put anything in my ass without simultaneously stroking my cock before), but he told me not to touch it because he didnāt want me cumming too soon. It kind of hurt to ride him fast, so he wanted to fuck me doggie style so that I couldn't stop him from thrusting hard. It kind of "burned" from the pain of his girth continually mashing through my hole and up into my guts. He was really stuffing me hard, too. He was thrusting his cock all the way in me so that his hips were mashed against my ass cheeks and his balls were slapping against my taint. He was going so deep that I felt a pinch in my stomach when his huge dick met resistance at that 90-degree turn, and I could feel the head "pop" through each time he forced the last two inches in. The feeling of having my guts straightened out when he went balls-deep was making me squirm. Whenever I would lurch forward a little bit, he would just pull back on my shoulders and slam his pole all the way in, as if to punish me for running from it. With a toy I can control the depth and speed, and I can just stop for a second when itās getting too intense. But with getting fucked, he was in control, so I just had to grit my teeth, curl my toes, and endure it. He could tell I was struggling to take it, but that made him even hornier. Justin and Brad were rock hard, beating their dicks as they watched Josh fucking my ass like he owned it. He was definitely getting off on claiming his prize. At first I was hoping that he would hurry up and cum, but then I started getting turned on thinking about how this felt on his end, and feeling his cock thickening and pulsing inside me.
Just when I thought I couldnāt take anymore, I asked if we could change positions and do it missionary. I got on my back and he spread my legs and pushed his thick pole back inside me. It felt better this way because of the angle of his cock. I wrapped my legs around his waist and squeezed him between my thighs as he continued thrusting into me.
The last position we did was ass up/face down (my favorite as either the top or the bottom). This hurt a little more than missionary, but not quite as much as doggie. The way his thick cock filled me up and hit my prostate with each thrust was starting to make me feel like cumming. He was bouncing up and down on me pretty hard, his hips smacking my perked cheeks and his weight driving my pelvis into the bed each time his cock plunged into me. I wasnāt touching myself, but I felt more and more like I was going to cum with each thrust of his cock. Just as I was getting close, he came first. He pushed himself all the way inside me and squeezed my shoulders with his hands. I could feel his body tighten up and his cock throbbing with each spurt. Being more of a top, it really turned me on imagining what it felt like for him, what it was like being inside me. While it would have been hotter if I had cum hands free while he was fucking me, I still shot an enormous load when I finished by hand.
I was pretty sore afterwards, but it was the hot kind of sore that reminded me of his warm, thick pole stretching me to my limit. Each time I "squeezed" my kegels as I walked back to my dorm room at 4 AM, I could feel the warm lube still squishing in my hole and between my cheeks. This combined with the soreness of being recently fucked prompted me to beat off at least twice more that night.
A couple of other guys have topped me since then, but this was the first (and still one of the only) intense bottoming experiences I have ever had. I actually donāt reminisce about it much, being more of a top, but it gets me really hot when Iām in a rare submissive mood. Sometimes, I secretly fantasize about re-living the experience of losing a bet to a dominant top with a huge dick and being obligated to take it whether I can handle it or not.
3 years ago
