My desire to play with big toys and get fisted started with my first boyfriend. He bought me my first dildo. He was about 7.5” and average thickness. One day he surprised me with a dildo about the same size as him. At the time, he was still fucking me at least once or twice a day. We fucked all the time. So, I was not sure why he wanted to bring a dildo into the mix, but I went along with it. I soon realized that I enjoyed the dildo, but I enjoyed his dick more. But when I talked him into trying to fuck me with both his dick and the dildo, it started something in me. At the time, I had never thought about stretching my hole open wide.
A few years later, I started working at the adult bookstore. One of the perks was we could buy anything at cost. We had a huge collection of dildos and the large ones really turned me on. I ended up buying the Jeff Stryker, Kris Lord and Rambone dildos. At the time, I thought they were massive. Now I think about them and they seem so average to me. The problem was the first boyfriend took that as an insult. He thought it meant his dick was not big enough. I was young and stupid. I did not realize how much it bothered him until it was too late. Needless to say, the bigger dildos did not get used very much. They spent most of the time in a storage bag in the back of the closet. The big toys stayed in that bag for many years, even after we had broken up.
When I worked at the gay bar, I started hanging around with a different group. Most of the workers were gay, including my fuck buddy that first introduced me to big cock worshipping with his monster cock. There were many times I would get a good face fucking after the bar closed (and a few times while we were open). But the most interesting was the 2 guys who ran the downstairs bar on the weekends. They were a bear couple, and they were both hot as fuck! We were always pleasant with each other, but we did not really bond. They had guys show up every weekend and it seemed like those guys would go home with the bear couple. I flirted with them a few times, but they never seemed interested.
Then one day, I was playing around in the adult bookstore and the younger ½ of the bear couple comes in. Him and I talk, and he wants to play around. So, we grabbed a movie off the shelf, and I got the key to one of the private rooms. We had 2 rooms that had a tv, dvd/vhs player (yes, it was that long ago), a couch and some chairs. We went into the room and sucked and fucked for a few hours. It was a hot time, but honestly, I always had a crush on the older ½ of the couple. We both had to leave, so I told him I would see him later at the bar.
That night at the bar, he was working, but the older ½ was working his other job. He asked if I wanted to have some more fun that night, with both of them. I told him I was game. So, after he got off work at the bar, we went to pick up the other one. We went back to their house and had a make out session in their living room. We had a few drinks and they put in a movie. On yeah, another thing about this bear couple, they had shot a few scenes for a bear porno company. They put in the DVD of the last movie they had made. One scene showed a small orgy scene which included the older ½. The next scene was 8 muscular/bear guys standing around a bathtub. Another one is in the bathtub and the 8 take turns pissing on him. At one point, the younger ½ (who is in this scene) starts making out with the guy next to him. They were not the main part of the scene, but you could tell they were doing things with each other. This is when he announces, “Oh yeah, this is where (other guy) fisted me. I forgot about that.”
This blew my mind. How could you get fisted and not remember? The camera was focused on the guy in the tub, so you could not really see much. I had just fucked him earlier and he was super tight. And when I fucked him later that night, he was still super tight. That blew my misconception that if you got fisted you were going to be loose.
A little bit later, I started fucking around with a guy that used to come into the adult bookstore a lot. Him and I never played around when I worked there. But we became good friends and even better sex partners. He gave the best blowjobs I had ever had. But the best part was his 8.5” thick dick. One day he told me that he liked to get fisted. I told him I had thought about it but had never done it. So, he set up a play session with another friend of his. I knew his friend and I did not have any problem with him, but I was not sure I wanted to have sex with him. But my friend and met at this guy’s house. My friend took me down to basement shower. He showed me how to use the ShowerShot and we then took a shower together. We went up and waited on his friend to show up. Once we were all prepared, my friend fisted his friend. I watched and they both told me what they were doing, gave me tips and then asked if I wanted to try. I hesitated, so they switched positions and the other guy started fisting my friend. I was mesmerized by the sight, so I lubed up my hand and started fisting him. They coached me and soon I was wrist deep inside my friend. The feeling was so different, so exotic, so erotic and so naughty. I loved it. I ended up fisting before the night was over. Over the next few years, I fisted my friend a few times. I knew that eventually I had to have it done to me.
One day I was at the adult bookstore, there was this big muscular guy. He was good looking. We went into booths next to each other and he was really into my pierced dick. We got to talking (through the gloryhole) and he asked if I wanted to go back to his place. I told him that I was interested. One the short walk to his place, he told me that he used to have a prince albert piercing, but he had to take it out. It was a shame to hear that, he had a beautiful 8” dick. He then shared that he was married, and she did not know he was into guys, but he loved to be fisted. He said his wife fisted him all the time. We go into his apartment, we got naked, and his body was magnificent. Very muscular, lots of piercings and tattoos. We both sucked each other. When I asked if he liked to top or bottom, he told me that he was not into that. That was saved for his wife. But he was up for getting fisted. So, I bent him over and lubed up his ass. I started pushing my fingers into his hole and his ass sucked up my hand. It was incredible. It was obvious that he was fisted a lot. And I loved how loose his hole was. After his ass was opened, I even did some punching. I loved fisting his ass. I ended going over to his place about 5 times. Always a good time. But I still was not sure if I wanted to get fisted or not.
It was not until met my 3rd boyfriend that I started thinking about the bigger dildos and getting fisted. He was a kinky guy, and we were always trying new things. One thing I loved about him was how much he loved working on my ass. He would rim me for hours. He would fuck me hard. He would love to watch other guys fuck my ass. When we bought a house, we setup a sex room in the basement. We had a bed and a sling in the room. We also had a cabinet full of lubes, poppers, cockrings, and toys. This when I brought out the bag of big toys. He loved to use those big toys to open my hole up. He loved playing with my hole when it had been used. His dick was 6” and average in thickness, but he is still the best top I have ever been with. He knew how to take care of my ass.
We had discussed fisting and he was wanting to try it on me. The problem was we had no idea what it would take. He would fuck me with the bigger toys, stretching my hole. He LOVED to shove one of those bigger toys in me and then he would push his dick in with the dildo and fuck me. We tried to fuck me with 2 of the dildos at the same time, but that never worked out very well. The few times he tried to fist me; he could never get his hand inside me. Neither one of us were ready for it. Neither one of us really knew what it would take.
After we broke up, I discovered the website asspig.com. Through their message board, I found all kinds of advice and tips. I learned about using Crisco, making my own lube, where to buy good poppers, where to buy the BIG toys, breathing techniques and how to properly stretch. But the best part was I discovered guys in my area who were into fisting.
The first guy I hooked up with from asspig was a 19-year-old kid. He loved to get fisted, and he offered to work on my ass. We played a few times, and he did try to open my ass up, but he could only get part of his hand inside me. Our playtime always ended with me fisting him.
Another guy I met on asspig was a guy I used to fuck at the adult bookstore. I had talked to some people about taking my first fist, and they all recommended him. He has small hands and was good at opening holes up. So he came over, he worked on my hole for about an hour. He got close but could never get his hand inside. So, I ended up fisting his tight ass. It was so tight, but it opened right up for my fist.
Then I met a guy who lived an hour away. He had lots of experience and he wanted to try working on my hole. I went to his house 3 times. Each time, he would work on my hole with my toys and his dick. Then after he had opened my hole, he would start using his hands. He was so patient and kept offering great tips. He taught me breathing tips. He taught me how to control my muscles. He got so close to getting his fist inside me, but we had to stop playing when he found out his cancer had come back. He moved back to his hometown and I never heard from him again. I owe his so much for his teaching. But I gave up on getting fisted after that.
Jump forward to 2 years ago. I was having so much fun with the gloryhole but I wanted to get fucked by some big dildos. The problem is I lost all the bigger toys I had. So, I started shopping the online sex shops. I had bought from Fort Troff before, so I started buying some of their dildos. I quickly learned what worked best when doing solo and what did not work. I bought some more that were a little bigger and then I bought some more.
Next came the fuck machine. I hated the machine when I first got it. It was difficult for me to use it by myself. Then I discovered that I could point the dildo straight up and fuck myself that way. I started using it like crazy. The more I went, the bigger the dildos got. And then the covid quarantine started and I moved into my boyfriend’s house for 3 months. I did not play with the dildos during that time.
When I finally started working again and I started staying at my place again, I started fucking myself with the bigger dildos. I had no problem taking them, so I bought bigger dildos. Eventually, after a few more even bigger dildos, I found a guy on Grindr who was into fisting. He was usually a bottom, but he was looking to be the top. He was intrigued by my gloryhole. I invited him over. While I was waiting, I set out some of the dildos and the lube. I also had a stack of towels and some wet wipes for him. I then got into the sling and waited. He showed up about 5 minutes later. He immediately got naked and then started lubing up my ass. He was good. He started with a smaller dildo. He worked it around and when he discovered I could take bigger. So, he worked his way up through the dildos until he found one that just right. He then fucked my ass like crazy. Pounding my ass with that dildo, then replacing it with 2 dildos. There were a few times that he got me so close to cumming with out me ever touching my dick. He knew when I was close, and he would slow down until the moment had passed. It was incredible! Finally, after about 2 hours, he asked if I was ready to cum. I told him I was, and he had gotten me so close a few times. He then started fucking me with his dick. Damn, we had never discussed his dick, I did not realize how hung he was. It was 8” and very thick. He fucked my ass so good and when he got close, he flooded my guts with his load. It was too much. I shot my load all over.
We agreed that he would come over again sometime, but the next time I would work on his ass. But I ended going back to work and he was only available when I was at work. We have talked a few times; he is still coming over sometime so I can have a crack at his ass.
So, knowing I needed to stretch a lot more before I could take a fist, I have been buying thicker dildos. I have no doubt that I can take my first fist, but I must find the right guy. Last year, the 3rd boyfriend came over to my gloryhole a few times. He seemed like he was interested in playing around again. I asked him if he was interested in fisting me sometime. He asked if I had been fisted yet. I told him that I had a few guys try, but nobody has gotten in yet. But I have been working really hard on stretching open with bigger toys. He told me that he was interested. But the few times we have talked after that, he was back to his old grumpy non-talkative self. So, I am not sure if he is interested or not. But for now, I keep on stretching and taking bigger and bigger toys.
A few years later, I started working at the adult bookstore. One of the perks was we could buy anything at cost. We had a huge collection of dildos and the large ones really turned me on. I ended up buying the Jeff Stryker, Kris Lord and Rambone dildos. At the time, I thought they were massive. Now I think about them and they seem so average to me. The problem was the first boyfriend took that as an insult. He thought it meant his dick was not big enough. I was young and stupid. I did not realize how much it bothered him until it was too late. Needless to say, the bigger dildos did not get used very much. They spent most of the time in a storage bag in the back of the closet. The big toys stayed in that bag for many years, even after we had broken up.
When I worked at the gay bar, I started hanging around with a different group. Most of the workers were gay, including my fuck buddy that first introduced me to big cock worshipping with his monster cock. There were many times I would get a good face fucking after the bar closed (and a few times while we were open). But the most interesting was the 2 guys who ran the downstairs bar on the weekends. They were a bear couple, and they were both hot as fuck! We were always pleasant with each other, but we did not really bond. They had guys show up every weekend and it seemed like those guys would go home with the bear couple. I flirted with them a few times, but they never seemed interested.
Then one day, I was playing around in the adult bookstore and the younger ½ of the bear couple comes in. Him and I talk, and he wants to play around. So, we grabbed a movie off the shelf, and I got the key to one of the private rooms. We had 2 rooms that had a tv, dvd/vhs player (yes, it was that long ago), a couch and some chairs. We went into the room and sucked and fucked for a few hours. It was a hot time, but honestly, I always had a crush on the older ½ of the couple. We both had to leave, so I told him I would see him later at the bar.
That night at the bar, he was working, but the older ½ was working his other job. He asked if I wanted to have some more fun that night, with both of them. I told him I was game. So, after he got off work at the bar, we went to pick up the other one. We went back to their house and had a make out session in their living room. We had a few drinks and they put in a movie. On yeah, another thing about this bear couple, they had shot a few scenes for a bear porno company. They put in the DVD of the last movie they had made. One scene showed a small orgy scene which included the older ½. The next scene was 8 muscular/bear guys standing around a bathtub. Another one is in the bathtub and the 8 take turns pissing on him. At one point, the younger ½ (who is in this scene) starts making out with the guy next to him. They were not the main part of the scene, but you could tell they were doing things with each other. This is when he announces, “Oh yeah, this is where (other guy) fisted me. I forgot about that.”
This blew my mind. How could you get fisted and not remember? The camera was focused on the guy in the tub, so you could not really see much. I had just fucked him earlier and he was super tight. And when I fucked him later that night, he was still super tight. That blew my misconception that if you got fisted you were going to be loose.
A little bit later, I started fucking around with a guy that used to come into the adult bookstore a lot. Him and I never played around when I worked there. But we became good friends and even better sex partners. He gave the best blowjobs I had ever had. But the best part was his 8.5” thick dick. One day he told me that he liked to get fisted. I told him I had thought about it but had never done it. So, he set up a play session with another friend of his. I knew his friend and I did not have any problem with him, but I was not sure I wanted to have sex with him. But my friend and met at this guy’s house. My friend took me down to basement shower. He showed me how to use the ShowerShot and we then took a shower together. We went up and waited on his friend to show up. Once we were all prepared, my friend fisted his friend. I watched and they both told me what they were doing, gave me tips and then asked if I wanted to try. I hesitated, so they switched positions and the other guy started fisting my friend. I was mesmerized by the sight, so I lubed up my hand and started fisting him. They coached me and soon I was wrist deep inside my friend. The feeling was so different, so exotic, so erotic and so naughty. I loved it. I ended up fisting before the night was over. Over the next few years, I fisted my friend a few times. I knew that eventually I had to have it done to me.
One day I was at the adult bookstore, there was this big muscular guy. He was good looking. We went into booths next to each other and he was really into my pierced dick. We got to talking (through the gloryhole) and he asked if I wanted to go back to his place. I told him that I was interested. One the short walk to his place, he told me that he used to have a prince albert piercing, but he had to take it out. It was a shame to hear that, he had a beautiful 8” dick. He then shared that he was married, and she did not know he was into guys, but he loved to be fisted. He said his wife fisted him all the time. We go into his apartment, we got naked, and his body was magnificent. Very muscular, lots of piercings and tattoos. We both sucked each other. When I asked if he liked to top or bottom, he told me that he was not into that. That was saved for his wife. But he was up for getting fisted. So, I bent him over and lubed up his ass. I started pushing my fingers into his hole and his ass sucked up my hand. It was incredible. It was obvious that he was fisted a lot. And I loved how loose his hole was. After his ass was opened, I even did some punching. I loved fisting his ass. I ended going over to his place about 5 times. Always a good time. But I still was not sure if I wanted to get fisted or not.
It was not until met my 3rd boyfriend that I started thinking about the bigger dildos and getting fisted. He was a kinky guy, and we were always trying new things. One thing I loved about him was how much he loved working on my ass. He would rim me for hours. He would fuck me hard. He would love to watch other guys fuck my ass. When we bought a house, we setup a sex room in the basement. We had a bed and a sling in the room. We also had a cabinet full of lubes, poppers, cockrings, and toys. This when I brought out the bag of big toys. He loved to use those big toys to open my hole up. He loved playing with my hole when it had been used. His dick was 6” and average in thickness, but he is still the best top I have ever been with. He knew how to take care of my ass.
We had discussed fisting and he was wanting to try it on me. The problem was we had no idea what it would take. He would fuck me with the bigger toys, stretching my hole. He LOVED to shove one of those bigger toys in me and then he would push his dick in with the dildo and fuck me. We tried to fuck me with 2 of the dildos at the same time, but that never worked out very well. The few times he tried to fist me; he could never get his hand inside me. Neither one of us were ready for it. Neither one of us really knew what it would take.
After we broke up, I discovered the website asspig.com. Through their message board, I found all kinds of advice and tips. I learned about using Crisco, making my own lube, where to buy good poppers, where to buy the BIG toys, breathing techniques and how to properly stretch. But the best part was I discovered guys in my area who were into fisting.
The first guy I hooked up with from asspig was a 19-year-old kid. He loved to get fisted, and he offered to work on my ass. We played a few times, and he did try to open my ass up, but he could only get part of his hand inside me. Our playtime always ended with me fisting him.
Another guy I met on asspig was a guy I used to fuck at the adult bookstore. I had talked to some people about taking my first fist, and they all recommended him. He has small hands and was good at opening holes up. So he came over, he worked on my hole for about an hour. He got close but could never get his hand inside. So, I ended up fisting his tight ass. It was so tight, but it opened right up for my fist.
Then I met a guy who lived an hour away. He had lots of experience and he wanted to try working on my hole. I went to his house 3 times. Each time, he would work on my hole with my toys and his dick. Then after he had opened my hole, he would start using his hands. He was so patient and kept offering great tips. He taught me breathing tips. He taught me how to control my muscles. He got so close to getting his fist inside me, but we had to stop playing when he found out his cancer had come back. He moved back to his hometown and I never heard from him again. I owe his so much for his teaching. But I gave up on getting fisted after that.
Jump forward to 2 years ago. I was having so much fun with the gloryhole but I wanted to get fucked by some big dildos. The problem is I lost all the bigger toys I had. So, I started shopping the online sex shops. I had bought from Fort Troff before, so I started buying some of their dildos. I quickly learned what worked best when doing solo and what did not work. I bought some more that were a little bigger and then I bought some more.
Next came the fuck machine. I hated the machine when I first got it. It was difficult for me to use it by myself. Then I discovered that I could point the dildo straight up and fuck myself that way. I started using it like crazy. The more I went, the bigger the dildos got. And then the covid quarantine started and I moved into my boyfriend’s house for 3 months. I did not play with the dildos during that time.
When I finally started working again and I started staying at my place again, I started fucking myself with the bigger dildos. I had no problem taking them, so I bought bigger dildos. Eventually, after a few more even bigger dildos, I found a guy on Grindr who was into fisting. He was usually a bottom, but he was looking to be the top. He was intrigued by my gloryhole. I invited him over. While I was waiting, I set out some of the dildos and the lube. I also had a stack of towels and some wet wipes for him. I then got into the sling and waited. He showed up about 5 minutes later. He immediately got naked and then started lubing up my ass. He was good. He started with a smaller dildo. He worked it around and when he discovered I could take bigger. So, he worked his way up through the dildos until he found one that just right. He then fucked my ass like crazy. Pounding my ass with that dildo, then replacing it with 2 dildos. There were a few times that he got me so close to cumming with out me ever touching my dick. He knew when I was close, and he would slow down until the moment had passed. It was incredible! Finally, after about 2 hours, he asked if I was ready to cum. I told him I was, and he had gotten me so close a few times. He then started fucking me with his dick. Damn, we had never discussed his dick, I did not realize how hung he was. It was 8” and very thick. He fucked my ass so good and when he got close, he flooded my guts with his load. It was too much. I shot my load all over.
We agreed that he would come over again sometime, but the next time I would work on his ass. But I ended going back to work and he was only available when I was at work. We have talked a few times; he is still coming over sometime so I can have a crack at his ass.
So, knowing I needed to stretch a lot more before I could take a fist, I have been buying thicker dildos. I have no doubt that I can take my first fist, but I must find the right guy. Last year, the 3rd boyfriend came over to my gloryhole a few times. He seemed like he was interested in playing around again. I asked him if he was interested in fisting me sometime. He asked if I had been fisted yet. I told him that I had a few guys try, but nobody has gotten in yet. But I have been working really hard on stretching open with bigger toys. He told me that he was interested. But the few times we have talked after that, he was back to his old grumpy non-talkative self. So, I am not sure if he is interested or not. But for now, I keep on stretching and taking bigger and bigger toys.