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Fulfilling my Fantasies with Jake

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Before I start, this story is 100% fictional!

My friend Jake is the guy of my dreams. He has defined abs and average sized muscles. I’ve always wanted to either get wedgies from him (I have a wedgie fetish) or get fucked by him. I’m about to tell you how both of those things happened in a single night!


My name is John and I’m a senior in high school. I recently 18 a few weeks ago and soon, my friend Jake will do the same. Since we started high school, I’ve always had a crush on Jake. We both played football and soccer, allowing us to have very fit bodies. After each practice I hung back, waiting for Jake to start showering, hoping to glance at his cock. I have been gifted with a thick, circumcised 8-inch cock and I hope Jake’s is also beautiful! The closest I’ve ever been to seeing his cock was during a soccer game two years ago. We were changing and i saw his meaty bulge through his boxers. Now, I’ve always been gay, but I’ve wondered about Jake. Of course, like the typical jock, he bragged about how many girls he banged. However, none of us actually had any proof, forcing us to question his claims. Usually after every practice, I go home and jack off to the one picture I have of Jake. It’s an old team photo of our soccer team shirtless. There are so many marvelous guys in that photo, but I had to focus on Jake! He is just so beautiful!

One day, after our football game, Jake approached me and asked if I wanted to hang out with him. Obviously I was excited, but I couldn’t let him know. I mean, we’ve hung out before, but it was still exciting just to talk to him. I tried to keep my cool and casually said, “Alright man. When?” He asked if tonight worked. Even though I already knew the answer, I replied that I had to go home, check in with my dad and get my stuff. After that, I would go over. He just said, “Whenever is fine with me.” Oh my god, I thought, he is so amazing! I went home, told my father, showered, and quickly ran to the store. Once I was there, I bought some condoms. You never know what might happen ;). I rang his doorbell and he let me inside. One look at his place and I was amazed! He had a massive house. There was a backyard, a huge kitchen with two islands, an enormous living room that conjoined to the dining room, an outdoor pool, everything you could dream of in a country home! We went up to his room and did some homework, played some video games, that kind of stuff. Soon after, we went outside and threw around a football and played a little bit of soccer. To cool off, we jumped in the pool and relaxed in his hot tub. I asked if I could stay for dinner and he said yes. His mom cooked up an amazing dinner consisting of roast chicken, potatoes, corn, and roasted carrots. After helping out with the dishes, we went down to his basement. Down there, he had a ping pong table, a pool table, another Xbox console, and a foosball table.

As it got late, my dad texted, asking if I was coming home. I asked Jake if I could stay the night, and being the wonderful guy that he is, he said yes. I asked him where we should sleep and he said down here would be fine. We continued to play in his basement until we eventually started to play Call of Duty. After a while, it got boring and I had figured out a way to possibly make out with Jake. A good old game of truth or dare. We started out with whoever lost a round of CoD had to do a truth or dare given by the other person. I won the first round and started easy. I asked him how many girls he’s banged in his life. Surprisingly, he said none. I quickly asked him why he lied to us, but he said he would only answer if I won another round. He won the next and dared me to play only in my underwear. I started taking off my jeans and t-shirt and quickly realized that I was wearing tighty-whities. I reluctantly exposed my embarrassing underwear to him and he started laughing. He told me that only nerds wear those kinds of underwear. He continued laughing throughout the next round until the round ended. He had won and instead of laughing, he smirked and told me that he was going to give me a wedgie for wearing briefs. I couldn’t let him know that I loved wedgies so I had to pretend like the fated wedgie receiver. I complained and ran away from him, but didn’t run too fast. He eventually caught me and explained that since I was trying to escape my dare, it was going to get worse. In his basement, there is a storage room with overhead metal beams. He told me that I was going to be hung up by my underwear for 10 minutes. I slowly walked towards the center of the room to where he placed a chair. I stood up on the chair and he attached the rope to the leg holes in my underwear. I asked him what the difference was between the leg holes and the waistband and he said he read that the leg holes were stronger. He tied the rope very close to the bar so I was farther off the ground. All of a sudden, he yanked the chair out from under me and I fell. As soon as my underwear stretched, I could hear the seams popping. For some reason, Jake had tied the underwear up so that I would be vertical the entire time! As I hung there, he told me that another punishment for running away was punches to the balls every 30 seconds. When my balls are constricted and are applied pain, it feels more than good. As he punched, I started to get hard and was nervous he would find out my secret. Either he didn’t care or didn’t notice because he never said a word about it. I only had a minute left when I leaked a little precum. I think he thought it was pee so he stopped punching. He left me there for the rest of the minute left and then he let me down. By now, he had noticed my tent and stood there with his mouth open. He asked me if I liked wedgies and I figured it would be better just to tell the truth. I told him yes and I also mentioned that I thought I was gay. Of course, that second part was a lie but he didn’t need to know that. I told him that I’ve always wanted to see his cock and thought that this sleep over would be a good chance. He replied that he was also gay. That’s why he hadn’t banged any girls. I told him that I had a crush on him and he told me that he had a crush on me.

We stood there in awkward silence, unsure of what to do. My cock was still raging hard, and he asked if I wanted to relieve my cum. Without my reply, he jumped down and started sucking my dick. I grabbed his head and started moaning with delight. Soon, he got a boner and started to jerk off. As I was close to cumming, I gave him a warning and he took my dick out of his mouth. He told me to fuck him. I asked if he had a condom, not wanting to be too prepared for this situation. He said yes and took out his wallet. He took out a condom and I put it on my dick. He took off his clothes and I finally saw his also circumcised cock. Damn, it was massive. When hard, it looked as if it were 9-inches. Jake went on his hands and knees and I slowly rimmed his asshole. God, he was tight. I asked if he was sure he wanted this and he replied with a sitting back motion, making my cock enter his hole. I leaned him forwards and pushed in. He started moaning and rubbed his cock. As I got more comfortable, I thrusted faster and harder while he started stroking more and more. Soon, my balls were slapping his body. He told me to stop for a little bit and he took me over to the spare guest room in their basement. He lay on his back on the bed and told me to continue. I started to fuck him and as I was close to cumming, he yelled out in ecstasy and spurted seven large ropes of thick white cum onto his chest and stomach. That took me over the edge and I came in his asshole, filling up the condom. I pulled out and disposed the condom in the trash. I laid down on the bed and sucked the cum off his body. That got him hard again and I started sucking on his cock instead. He gave me a sign that he was going to cum and I stopped. I told him to fuck me instead. He searched for another condom but I told him I wanted to feel his real dick. He stood up and inserted his cock into my hole. I couldn’t keep myself from moaning, it felt much better than a rubber dildo. He fucked me harder and harder until he eventually came. It felt so good, having his juices in my ass. I had came a medium amount of cum all over my stomach and chest. He then knelt down and gave me another blowjob and as soon as I was about to cum, he stopped and took his mouth off my cock. I came all over his face, a much bigger load than I’ve ever spurted. Somehow, we fell asleep and when we woke up, his mother walked by laughing, telling us to clean up and to keep it down next time.

It became a regular thing, the two of us. I came over to his house, he slept at mine. He would give me wedgies until I came and he would eat the cum from the cotton. We would fuck occasionally, almost every night. Exceptions for family events and other stuff like that. Soon, we let our families know we were together. We even got into the same college and saw each other every day! Even now, a few years later, I still fuck him and he gives me many varieties of wedgies!

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