About one year ago I was visiting a friends house chilling on his bed, we'll call him Greg. Greg was always a trickester and our relationship as friends was always about joking around. While visiting I took Gregs phone and stuffed it into my back pocket, of course Greg would fight to get it back but Im like twice his size so it was pointless trying to get it back that way. Greg thought it was a good idea to just pull the sheets from under me but I was too heavy for that to work. Of course he realized what a ridiculous plan it was so he opted for a different strategy. His plan was to instead slowly pull my pants down and risk embarassing myself or giving in and return his phone. But I wasnt a push over and let him continue his plan. But it did not go as planned. There I was pretending to sleep since I knew his efforts were futile until I felt a breeze on my crotch and realized Greg had slipped up and accidently pulled my briefs down.
In my head I was shocked he had the balls to along with his plan and another side of me was curious to see what Greg would do now that he had seen my cock. Which was so unlike me btw. I expected a response from Greg but instead he was in awe, jaw dropped. After his trance he had told me that he had seen plenty of dick but he had never seen one as thick as mine was. I was flattered and weirded out with the situation, even though we were close friends I had never thought that one day something like that would happen.
Out of the blue Greg excitingly asked if he could suck me off. I was hesitant at first but I mean what guy wouldnt turn down a bj? I let Greg do all the work since at the time it was my first time getting a blowjob, until only 20 seconds had passed and he was out of breath cursing. Greg said he sucked dick before but never had to worry about his jaw cramping so I thought Id give him some help. I told him to get on the bed with his face towards the edge, I got up and pointed my cock right at his face. He started laughing saying hes never been intimidated by a dick before that day. I let him catch his breath before I went to town on his face. There was a lot of teeth and short breaks but I dont blame him.
From that day foward Greg became friends with benfits, except one week when I visited for game night he wanted to take things a step further. He wanted to do anal, Greg was so eager he prepped for a week and a half. In secret he practiced with a dildo and lube because he was scared I wouldnt fit. I aggreed but I was worried the dildo wasnt enough practice for him. When the time finally arrived Greg prepared the bed and got condoms and lube from his night stand. He got onto the bed and presumed his position. I appreciated all the effort Greg had put into that night, but there was a glaring problem. The condoms that Greg bought were too small for me. I mean my cock isnt the longest so the condom was just enough to cover the whole shaft, but the width of the condom was small. Wearing it was painful and it felt like a vice grip on my cock but thats all Greg had so I made do.
Greg had sex before but he was always a top in his relationships never had he taken a dick up his ass and was quite nervous. To ease him into it I loosened up his ass with some fingering. One, then two, and finally three fingers, I really wanted to make sure Greg wasnt being split in half so I took it slow. I was holding back the fiery urge to stop all that and rail his ass. When I thought he was ready I took some lube onto mh cock and teased his tight hole with the tip. Soon enough I tried to enter his ass slowly as too not hurt Greg, but it was pointless. Upon entry Greg gasped with a mix of pain and pleasure. He said he wasnt a bitch and begged me to go deeper. I laughed and said well I cant say I didnt warn you and thrust my hips a little.
Immediately Greg screamed in pain and pushed my waist back with his hands. I gave him a little time to adjust to my size, but it wasnt even halfway in. After a quick breather from Greg he told me to continue. I was getting a little impatient so I thrusted back in about 3\4 of my shaft. Greg screamed my name and thats what really let gates flood, so I took out my cock and shoved it back in.
Plap Plap Plap I
Id only thrust a little more than half my cock in Gregs tight ass each time, the only noise that filled the room was Gregs moaning and the sound my balls slapping his cheecks. Alas it was short lived Greg only lasted 15 seconds before he gave into the pain. He asked my to stop because the pain was beginning to be unbearable. A little dissapointed I understood. I finished off by jerking it and giving him a creampie.
Sadly my girth was too much and it lead to a bad experience. I was wondering if there are any stories that youd like to share with the same situation or the complete opposite where your girth was something someone really enjoyed.
In my head I was shocked he had the balls to along with his plan and another side of me was curious to see what Greg would do now that he had seen my cock. Which was so unlike me btw. I expected a response from Greg but instead he was in awe, jaw dropped. After his trance he had told me that he had seen plenty of dick but he had never seen one as thick as mine was. I was flattered and weirded out with the situation, even though we were close friends I had never thought that one day something like that would happen.
Out of the blue Greg excitingly asked if he could suck me off. I was hesitant at first but I mean what guy wouldnt turn down a bj? I let Greg do all the work since at the time it was my first time getting a blowjob, until only 20 seconds had passed and he was out of breath cursing. Greg said he sucked dick before but never had to worry about his jaw cramping so I thought Id give him some help. I told him to get on the bed with his face towards the edge, I got up and pointed my cock right at his face. He started laughing saying hes never been intimidated by a dick before that day. I let him catch his breath before I went to town on his face. There was a lot of teeth and short breaks but I dont blame him.
From that day foward Greg became friends with benfits, except one week when I visited for game night he wanted to take things a step further. He wanted to do anal, Greg was so eager he prepped for a week and a half. In secret he practiced with a dildo and lube because he was scared I wouldnt fit. I aggreed but I was worried the dildo wasnt enough practice for him. When the time finally arrived Greg prepared the bed and got condoms and lube from his night stand. He got onto the bed and presumed his position. I appreciated all the effort Greg had put into that night, but there was a glaring problem. The condoms that Greg bought were too small for me. I mean my cock isnt the longest so the condom was just enough to cover the whole shaft, but the width of the condom was small. Wearing it was painful and it felt like a vice grip on my cock but thats all Greg had so I made do.
Greg had sex before but he was always a top in his relationships never had he taken a dick up his ass and was quite nervous. To ease him into it I loosened up his ass with some fingering. One, then two, and finally three fingers, I really wanted to make sure Greg wasnt being split in half so I took it slow. I was holding back the fiery urge to stop all that and rail his ass. When I thought he was ready I took some lube onto mh cock and teased his tight hole with the tip. Soon enough I tried to enter his ass slowly as too not hurt Greg, but it was pointless. Upon entry Greg gasped with a mix of pain and pleasure. He said he wasnt a bitch and begged me to go deeper. I laughed and said well I cant say I didnt warn you and thrust my hips a little.
Immediately Greg screamed in pain and pushed my waist back with his hands. I gave him a little time to adjust to my size, but it wasnt even halfway in. After a quick breather from Greg he told me to continue. I was getting a little impatient so I thrusted back in about 3\4 of my shaft. Greg screamed my name and thats what really let gates flood, so I took out my cock and shoved it back in.
Plap Plap Plap I
Id only thrust a little more than half my cock in Gregs tight ass each time, the only noise that filled the room was Gregs moaning and the sound my balls slapping his cheecks. Alas it was short lived Greg only lasted 15 seconds before he gave into the pain. He asked my to stop because the pain was beginning to be unbearable. A little dissapointed I understood. I finished off by jerking it and giving him a creampie.
Sadly my girth was too much and it lead to a bad experience. I was wondering if there are any stories that youd like to share with the same situation or the complete opposite where your girth was something someone really enjoyed.
