The Story Of How I Accidentally Lost My Anal Virginity. [Anal] | 2016

So begins the story of how I accidentally lost my anal virginity… which is also the great tale of Wadboy. Or, as my best friend knows him “the guy who used your toothbrush.”

Wadboy has a pretty distinctive name, so for the purposes of my story I will just refer to him as “Wadboy” and you’ll find out toward the end of the story why he is called that.

I graduated university in the Summer of 2009 along with a dude who was dating a girl I worked with. So, the girl threw a party for our graduation. Everyone at the party was friends with the dude and his girlfriend, so I didn’t really know anyone, but I was having fun, and getting plastered anyway. Obviously, this was before my straight edge days. Interestingly enough, it was the events of Graduation Weekend that prompted me to stop drinking (I’ve never done drugs or smoked, so drinking was the only vice to give up to be straight edge). Anyway, party, people I don’t know, but having fun and getting drunk.

First thing you should know about me: I’m a horny drunk… granted I’m pretty horny sober, too. That being said, I was willing to make out with just about anyone. I’d love to tell you that the majority of the dudes at this party weren’t losers. But, the only one who wasn’t was the one who was dating the girl I worked with (we’ll call her Natalie)… and she was there too… so, even though I tried, I could not make out with him. Instead, I ended up making out with his best friend. In front of most of the other party goers.

My choking fetish had also come up in conversation at the party, so he was also choking me in front of most of the other party goers. At one point, he was even making out with me on the porch while Natalie was rubbing my crotch. That was actually kind of hilarious because my initial thought was “HOW MANY HANDS DOES THIS GUY HAVE,” then I realised… wait, that’s Natalie’s hand rubbing my clit through my pants! Which was weird, because while we both knew that we had both been with girls in the past, we had both explicitly said that we were not interested in each other. It’s amazing what booze can do in that capacity.

So, the party was on Friday. There was much drinking, even more making out. Eventually, Wadboy and I went upstairs to one of Natalie’s roommates’ bedrooms. Wadboy went down on me. He was eager but it was pretty bad. Not bad in the sense that I wasn’t really enjoying it… I mean, the stimulation was good, but it was bad in the sense that I knew from the beginning that it wasn’t going to get me off. I let him continue at it for about 20 minutes though. He stopped. I told him I wasn’t going to fuck him, and that was it. We cuddled in the roommate’s bed and eventually fell asleep.

In the morning we were awakened by the roommate coming into her room, unsuspectingly. She quickly gathered her things while we apologized profusely, but stayed in her bed, and watched her leave. Once she left, I ran to the bathroom to barf.

Wadboy and I spent pretty much all of that day, Saturday, together. We took a walk in the wooded area near my house. He shoved me up against a tree, and we made out until we heard voices coming up the path, at which point we continued down the path. There was an area with a couple of benches under a gazebo, where he insisted on making out. So, we did for a bit, and then he walked me back to my house. Of course, I never told him that there were wet spots on his pants from his pre-ejaculate. Hey, not my fault I’m that good at making out! I don’t think anyone noticed anyway.

So, he dropped me off at my place and went back to Natalie’s. Natalie calls me later that night and tells me that everyone, including Wadboy, is going to a house party. One of the dudes who was at the Graduation party had his parents’ house to himself for the weekend, so he was having a bunch of people over. Since I had drank a ridiculous amount at the Graduation party, I didn’t drink much at the house party. I had a slight buzz but I was nowhere near drunk. Wadboy was drunk AND high, and all over me. Which, I really didn’t mind, but I was way less willing than I was when I was smashed the night before. He kept trying to take my pants off in the living room in front of everyone, but I wasn’t having it. Finally, I called his bluff and told him we could go find a bedroom. So, I grabbed 2 condoms from Natalie and we found the master bedroom in the random guy’s house.

Wadboy was definitely one of those guys who doesn’t know what foreplay is. I was naked in seconds. He wanted reciprocation from the oral the night before, but for some reason I REALLY didn’t want to go down on him. That was when the head pushing started. ProTip, guys: don’t push down on her head. Normally, if a guy pushes down on my head, I just warn him that if he’s going to do that, I just won’t go down on him. But, in this case, I just really didn’t want to go down on Wadboy, like I said. So, he pushed harder. That was when I dug my teeth into his stomach and almost ripped out a chunk of flesh.

At that point, he decided that there had been enough foreplay and that he was just going to fuck me. He threw on a condom and flipped me onto my back.

Second thing you should know about me: I get REALLY wet, REALLY easily. That being said, I was obviously really wet. But, I guess subconsciously, I still really didn’t want to fuck him, so I was clenching my vag tight enough and he was trying to ram it in there hard enough that the combination of the clenching, thrusting and me being soaking wet… well, he ended up sliding right into my asshole.

This lasted all of three thrusts, each with a respective thought in my brain. Thrust 1: OHGOD OW. Thrust 2: FUCK WAIT, THIS IS GOOD PAIN. Thrust 3: OHGOD HE DOESN’T KNOW HE’S FUCKING ME IN THE ASS. By Thrust 3 he realised he was in, but he didn’t realise he was in my ass, so he was just starting to get into a thrusting rhythm which would have been find for rough vaginal sex, but no one wants rough anal sex… especially when I had never had anal sex before. Before he could make it to Thrust 4, I shoved him off of me, and told him he was fucking me in the ass. He tried to get back on top of me and correct things at which point I yelled at him that he had to change his condom (after all, we had two, and it’s REALLY not healthy to do ass-to-other-orifice). He grudgingly obliged but couldn’t find the second condom. Which was when I finally just got angry with the situation and started putting my clothes back on. Realising that I was blueballing him, he got even angrier than I was and stormed out of the room to go get high again. I went downstairs, sat next to Natalie on the couch and said, “Welp, I just got my brown belt.”

He barely talked to me for the rest of the night, but the four of us (Natalie, her boyfriend, Wadboy and I) all left the party together. We cabbed back to Natalie’s house, and we watched a movie until 4am. Wadboy apologized, and wanted to make out again, but then the three of them got high and he ended up falling asleep. I walked myself home at about 6am.

That night, Sunday, Wadboy called me and asked if he could come over. I said sure. He ended up making other plans and didn’t come over. I didn’t really care. He called me the next day, Monday, and asked again if he could come over. Once again, I said sure, this time thinking he just wouldn’t come. He did, though. He showed up at my door and asked if he could use my toothbrush. I didn’t think it was a big deal. I had been making out with him all weekend. And, I figured, I was probably going to make out with him again that night, so I’d rather that he brushed his teeth than make out with someone who hadn’t brushed their teeth all weekend (he was visiting from out of town for the graduation party and forgot his toothbrush). When I told my best friend this story, however, she was completely disgusted by the fact that I let him use my toothbrush. I still don’t think it was THAT BIG of a deal.

So, we end up making out, but I still don’t want to fuck him, or even go down on him. Basically, we dry humped until he was ready to cum, and then I told him I was going to sleep. He begged me for about 30 minutes to get him off. I still wouldn’t. He decided that maybe if he got me off first, I’d get him off. I knew I wasn’t going to get him off at all, but I wasn’t going to pass up the opportunity to get off, so I let him finger me until I came, and then rolled over to go to sleep. That was when he asked if I would mind if he just masturbated instead. I didn’t care. So, he beat off, and then fell asleep, too.

The next morning, I had to work. He showered and ate my cereal (I didn’t get to shower, OR eat) and used my toothbrush again. But, I’m sure you’re still wondering why I call him Wadboy. While he was in the shower, I was in my bedroom getting dressed for work. Remember I told you he masturbated before he fell asleep? Well, he jizzed into some Kleenexes, which I found on my floor while he was in the shower. Now, I’m not talking one or two Kleenexes balled up and tossed on my floor… I’m talking a SOFTBALL SIZED WAD of Kleenexes that was HEAVY AND STILL WARM when I picked it up to throw it away. I nearly died.

I went to work, assuming (HOPING) I would never see my weekend fling again. I get home, check my cell phone and see that he has emailed me about 3 times, and has also called me… THIRTY SEVEN TIMES. I called him back. He wanted me to go to a party 4 hours away that night. I had to work the next day, so I said no. He tried to convince me anyway. I said no, and hung up. He sent me a couple more emails, called me a couple more times. I was pretty distant about everything, and eventually he left town, or something like that, so he stopped emailing me. Keep in mind… this was Summer 2009. He finally stopped emailing me probably around August 2009. AND THEN I GET AN EMAIL FROM HIM IN OCTOBER OF LAST YEAR! He told me that he had moved back to town and wanted to hook up again. WHO CALLS SOMEONE THIRTY SEVEN TIMES AFTER BEING BLUEBALLED 3 TIMES AND THEN TRIES TO HOOK UP WITH THEM AGAIN AFTER NOT TALKING FOR OVER A YEAR!?

The story gets slightly more embarrassing, too. I tell pretty much all of my sex-life stories at work for the lulz, because that’s just what I do. People at work like laughing at my misfortunes, and I’m ballsy enough that I can take people laughing at me for the sake of a laugh, so I tell the stories, and everyone has a good time. I told this story, only to find out that one of my coworkers (other than Natalie) knows Wadboy from high school, and knows how incredibly psycho he is!

Moral of the story? I went straight edge because drinking led to me being accidentally butt-fucked.