My Straight Friend
Begging me to Defile Him
Begging me to Defile Him
Growing up one of my closest friends was always famous for his height. As an adult he ended up being 6’5.” I was always intrigued by his height and always thought it must mean he had a really big dick. As much time as we spent together, I only ever caught brief glimpses of it here and there. He wasn’t shy at all about it, it just didn’t happen too often that I would see what I wanted.
At any rate, we were coming out of high school just as AOL and Messenger were a thing. As we all know, one of the things the internet did was take away inhibitions. In a lot of ways, it became technological alcohol.
Tom and I never talked too much about sex. It just didn’t come up when we were together. However, one day when we were chatting on AOL, out of nowhere, he typed, “I want you to fuck me.”
I was floored! I thought for sure he either sent the IM to the wrong person (that used to be a thing!), or maybe a friend of his was there and had commandeered his computer while he went to the bathroom or something. When I questioned him on it, he insisted. Before continuing, I asked him to type me something that only he and I would know. Without any delay, he typed something that was our inside joke and that was only between us. I knew it was him who had typed that.
I asked him where this was coming from and what he meant. He typed back something like this, “Man, every time I fuck a girl, she screams because of how big I am. Like, really screams. So, I have this fantasy to get fucked so I know what it feels like when I’m doing that.”
Damn! So, he was telling me flat out that he was huge, and, that he wanted to get fucked…BY ME! I asked him, “Dude, is it really that big?” He replied, “yes, big, and fat.” Before I could ask, he sent me two pictures. One of him hard and another of him having just busted, with his cum all over his hands. I also noticed how big his balls were…huge! He told me, “I’m 7.25, but can get to 7.5 on a really good day.”
I asked him to tell me more about what he wanted. He told me something to the effect of, “yeah, so, I have this fantasy that I am taking it from you missionary style and you keep going until two things happen: you make me cum while you are fucking me and we’re making eye contact; and, you don’t stop fucking me until you cum inside me like I’m the girl.”
I could not believe my eyes. This was all so out of character for him. We didn’t ever talk like this — ever. I told him, “geeze, Tom, it seems like you have given this a lot of thought.” He replied, “I have. I’ve been jerking off to this fantasy for like months now.”
It caught my attention that he was specifically fantasizing about me being the one to do this, like not just having it done to him, but it being me. I asked him about that, and he said, “I didn’t plan it, Mike. You know how fantasies are. They just happen. And that’s what I want…I want this fantasy to happen.”
Now, there was no way I wasn’t going to give him exactly what he wanted. We had been friends since age seven. So, if this is what he wanted to do, I was going to make it happen for him. Really, for us.
I asked him when he had in mind and he told me, “in two weeks when we’re together for the 4th of July weekend.” Damn! He really did have a plan. I told him, “Tom, obviously, I’m going to do this with you, but I’m not sure I’m completely qualified. If you want someone to make you scream, I’m not nearly as big as you are.” He said, “no worries. I’ve never had anything it my ass before, so whatever you have is going to feel huge to me.” Bet!
The next two weeks felt like an eternity. There was so much anticipation. What I really worried about more than anything was if I would satisfy his fantasy. If I were going to do this, I wanted to do it right and be good at it. I was a man on a mission now.
At long last, the holiday weekend arrived. We were driving up to the beach together in my car, and would be staying at my family home. There would be a lot of people there, but the place was plenty big enough, and there were plenty of places to go or be away from others. Normally, Tom would have his own room, but no one would question it if we both slept in the same room. Still, if we were going to engage in the escapades that he had elaborated on, there would need to be an opportunity to be alone. We knew our best shot would be to get up there before anyone else, and so that’s exactly what we did.
The ride, which was less than two hours, felt like an eternity. There was a lot of nervous anticipation and energy in the car. I finally broke the silence and asked, “so, what’s the plan? Like, we get there, go upstairs, and fuck?” Tom laughed and said, “haha, yep!”
Wow. A guy I have been friends with for all these years, and today I was going to take his anal virginity at his request, basically at an appointed time. This was really something else. To boot, he was approaching it all so matter-of-factly.
We finally pulled in, grabbed our duffle bags from the car, and went straight upstairs. The moment we got in my room, Tom began getting undressed. In no time flat, he was naked and laying on my bed. I followed his lead, taking off all my clothes and dropping them on the floor. He tossed me a small jar of Vaseline and told me, “lube me up good, please.” I smiled and said, “yes, Sir. Is there anything else I can do before I defile you?”
He chuckled at me and said, “well, we never discussed how into this you are or aren’t, but if you want to loosen me up a bit, I wouldn’t mind the favor of being rimmed or fingered a little bit first. He drew his long legs up and bent his knees to his chest, so his ass was completely mine and just inches away. He had this like blondish, reddish-brown pubic hair and hair around his asshole, and a light covering on his ass. It looked cool the way the sunlight was shining in the room, glistening off of the shimmering water outside the window.
I crouched down on my knees and buried my face in there, nose right into his hole. I heard him inhale deeply. I went for it, plunging my tongue into his hole. It was the first time I had ever done such a thing. It was overwhelming. So many stimulations of the senses. His smell, how warm it was, the emotional experience realizing what intimate thing we were doing. How soft and silky his hole felt to my tongue. The sound of his breathing. It was a lot all at once.
After a few minutes, I spit on his hole, licked my finger, and pushed it inside. He writhed a little bit, but I pushed it further until it was all the way in, and then I started working his hole a bit. I was surprised at how vocal Tom was. He seemed to really be enjoying it. Every inch of his insides felt so silky soft and smooth. I had no idea what I was expecting, but it was a pleasant surprise.
Finally, he looked at me and said, “I want you to stick it in me now.” I asked, “are you sure?” He said firmly, “yes.”
I pulled out my finger, and instinctively, licked it and sucked it clean. He asked me how it tasted, and I told him, “I love it.” That was true. I loved the way my friend’s asshole tasted, and I wanted him to know it.
I put some Vaseline on my dick, and pressed it up against his hole, and then pushed inside of him. He blurted out, “Jesus, God!” I asked him if he wanted me to stop, and he said, “no, of course not. It feels good. I want you to fuck the cum out of me.”
So, I began fucking him. And, I do mean fucking him. His hole was fucking tight. The harder I pounded him, the harder it seemed he wanted me to do it. Tom has these huge blue eyes — his best feature. He reminded me he wanted us to be making eye contact, and this was going to be easy to do with those big baby blues. I asked him what it was about the eye contact, and he told me it was because he wanted to feel submissive like the girls he fucked. I understood what he meant.
We locked our gazes and I got into a rhythm pounding his tight virgin hole. He was stroking his big, fat cock, and his giant balls were bouncing up and down. I imagined he would cum a lot when he finally busted.
He was making lots of noise. I’m not sure if it was exactly screaming, but it was close enough for sure. Soon, he was getting close. He told me he was going to squirt on his chest soon, and instructed me not to stop. We maintained that eye contact, he continued stroking, and then began grunting very loudly and very hard. Cum began blasting out of his cock and right up his chest, just like he said it would.
After six or seven blasts, it was subsiding, and he told me to lick it up and spit it into his mouth. We had not discussed that at all, but I didn’t even think about it, I just did it. There was so much cum that it took me at least a half dozen “trips” with my tongue from his body to his mouth to deliver all the cum. I was shocked he was so into eating his own cum, something I could never do. I will say that his cum tasted Heavenly. I was surprised how good it tasted to me. I was sure to swallow some for myself. I felt like it was a reward. I even headed down to suck the last few drops right out of his piss slit. What a treat!
I was still inside him and fucking, but I had slowed down during his orgasm and the cum feeding.
When he had eaten all there was, he told me to fill him up, so I resumed fucking. Seeing him laying there like that, looking up at me, with cum all over his face put me over the top. I told him I was ready to bust. I gave him several deep thrusts, each one delivering a hot shot of cum. He said, “Jesus, God” with every one of them.
When I was done, he wrapped his legs around me and told me, “no, don’t pull out. Just let it stay in there.” Ok…I did it, but didn’t know what to do at that point. I wanted to kiss him, because it’s what felt right, but I was hesitant to try that.
Finally, I got brave and leaned in, hoping he wouldn’t reject me. He opened his mouth and latched onto my tongue, kissing me pretty intensely for several minutes before releasing my tongue. I was just laying on top of him with my dick still inside. It felt nice. It was somehow so familiar, in spite of the fact that this was all wildly new and totally unknown to both of us.
He told me, “when you pull out, try not to let your cum leak out. Push it back in me as much as possible.” I did exactly as he asked.
I asked him how his asshole felt, and he said, “it feels great. It feels like it was made for that.” What an answer!
We stayed on the bed for a while, just talking about whatever…normal things, really. After a while, I asked if he wanted to shower, and he said, “no. I don’t. I just want to stay like this.” Wow, ok. Tom was just filled with all kinds of surprises.
So, I asked, “what do you want to do?” He said, “let’s go get sodas and ride the Jet-Ski until your parents get here.” He stood up and took his swim trunks out of his bag, and slid them on. I followed suit. I asked him if he wanted to put his stuff in his room. He looked at me half-disgusted and said, “really?” I just said that I didn’t mean anything by it, and he could obviously sleep wherever he wanted.
Tom said, “obviously, I’m sleeping with you. You really think your parents don’t already think we do this stuff together?” I was shocked, and told him I was sure they did not. He just laughed and said, “yeah, OK. Didn’t you hear your aunt refer to me as your boyfriend last year?” WHAT?! NO, I DID NOT!!!
I really didn’t think they thought that at all. All of this was a shock to me. I imagined it would kill my poor mother if she found out.
Tom told me my parents were a lot smarter than I gave them credit for. That night when we got in bed, I asked him, “so, what now?” He laughed and said, “what do you mean?” I asked him, “well, so what has changed between us.” He replied, “nothing at all. Nothing has changed between us.” He rolled over, and spooned me, being the big spoon. I could feel his warm breath on my neck, and his arm around me. I leaned back around and kissed him on the lips. He returned the kiss. It was so comforting and so comfortable. That’s both how we fell asleep, and how we woke up: entangled in one another, and naked…
