Tighty Whities

My friends will attest to the fact that I can get a little obsessed with Grindr. I used to go through these spurts where I would literally spend entire days at work on it trying to meet people, mainly for sex. I was still fairly new to this whole homosexual world and wanted to experience sex with many different kinds of men. I prided myself on not being too critical or picky. If you were fat, unkempt, Asian, or bald it didn’t matter I would still probably hook up with you. I looked at it like how would I know who or what I was ultimately attracted to if I didn’t try it, and seriously with a little bit of alcohol I could close my eyes and every man looked like Nick Bateman, well maybe not exactly, but there was a blurry outline.

I also didn’t turn down most fetishes. I mean sure I’d give nipple clamps and foot lickers a shot, but I wasn’t indulging fisters, people who wanted me to birth golf balls, or scat, but for the most part I was open to your desires. And one fetish that I routinely encountered was people who were obsessed with underwear. What type of underwear was I wearing? What color were they? Were they clean or dirty? Can you send me a pic of you in your underwear? Out of your underwear? Your underwear being washed in a washing machine? It always got a little annoying after a while. Like how many pictures do you really want to see of my underwear, can’t we just fuck already?

The most interesting underwear fetishist came about one day while I was on Grindr during a break between classes in grad school. I went to a rather large University for grad school and I thought that this would mean that there were tons of students available to fool around with, even if the majority of them would be 18 to 22. However, this was not the case. Whether college students weren’t Grindr savvy yet, or this university had a more closeted culture the prospects were slim. There was this one kid who would often come up who had the face of a model, chiseled, handsome, and sure of himself. Plus he was 23 which was a huge plus because I was not at all a fan of cradle robbing (yet), but I would “settle” for a 20 year old in a pinch. I would never message this kid on Grindr because I thought that he was just too beautiful for me, and seriously he probably lived on campus, so where were we really going to hook up anyway? I was a little past hooking up in dorm rooms at this point. However, at the end of the semester while sitting in the library pretending to work on a paper about the disenfranchisement and gentrification of Asian elephants I received a message from him on Grindr and was beyond excited. It turned out that we had a bunch of things in common as he was going for his Bachelors in social work and I was getting my masters.

I don’t know exactly how long the messaging lasted, but it must have been a few weeks because by the time we planned on meeting the semester was already finished. It was one balmy spring morning and I must have turned on Grindr to stave off boredom. He was on and we began chatting and soon the chatting became ridiculously suggestive, and then the requests for underwear pics began. The requests were simple enough in the beginning. Send me a picture of you in underwear, take a picture of the underwear off of you, and send me a picture of your underwear drawer (that last one totally happens more than you would believe)? I don’t understand why people get off on just seeing pictures of my everyday underwear. I totally get that sexy underwear can be a turn on, but I can assure you that there is nothing arousing about a pair of baby blue boxers from the Gap covered in tiny penguins wearing Santa hats, trust me.

These requests then escalated to things that I had not encountered and should have begun to send me red flags, but I was waaayyyy too open-minded in the beginning and was pretty much down for anything. He began to ask pictures of me stretching my underwear on me. This was a new request. However, he then asked me to take them off and take pictures of me stretching them to see how elastic they were. Not only was this request out of the ordinary, but very difficult to capture. I mean I needed two hands to properly stretch the underwear and a third hand to snap the picture, and unfortunately I only have two hands. So there I was in my family room using the corner of a desk and my other two hands to attempt to get a “sexy” picture of my underwear stretching. It was at this moment that I began to think, “What the fuck am I getting myself into?” At this point the morning was waning into the afternoon and I needed to know what was going on because I don’t need someone to waste my time. If you wanna hook up let’s just get there. I don’t need to see a billion pictures in preparation.

He finally agreed to meet at the university, and I began the drive down. When I arrived the person that I met was vastly different than the kid in the picture, not that it wasn’t the same person because it definitely was, but the kid’s profile pic was definitely a photo shopped head shot. I don’t need you to look exactly the same, but please try and use everyday pictures because when we actually meet we aren’t going to be on a photo shoot. We are going to be in your living room, and you will most likely be in sweat pants, let’s be honest. The other thing that was slightly off putting was that he was very feminine. Now I am by no means saying that I am some hyper-masculine jock or anything, but traditionally I tend to be attracted to men who are more masculine than I am, and this kid was far from it. He talked with that accent that sounded like every word out of his mouth was supposed to be seductive. I’m sure even if he said, ‘I just dropped a deuce and didn’t flush” would have sanded like “I want to gag on your cock and swallow your load.” I don’t need to feel like I am in some badly scripted porno film from the first second I meet someone. Despite this he still had a good face, slightly less handsome than in his picture, but surely more than workable.

He led me to these woods behind his dorm room and whipped out a joint. Now things were starting to get very interesting. I don’t usually smoke marijuana, but will definitely indulge myself from time to time, and at this point I had no idea where to get it from so I had to take advantage of the opportunity when it arose. However, I was such a novice at this time that it still made me paranoid, and being in the woods with a stranger was not helping anything. However, it turned out to be a nice experience we chatted, and walked around, and it was really a beautiful setting overall, I must say. At some point the high began to wind down and it was time to put on the Ritz. We were standing against this one tree and the kissing started. I love kissing while high. I feel like it really intensifies it, like the rest of the world fades into the background and all that is left are your lips and his/her lips and black space, and it feels as if time just stands still. It is probably one of the most intoxicating experiences for me. I don’t even really like to have sex high, but kissing is so enjoyable.

After kissing for God only knows how long our hands started undoing each other’s pants and the hand jobs began. This lasted for probably a few minutes and then he was whispering in my ear “give me a wedgie.” My internal response was “WWWHHHHHHAAAAATTTT!?,”but my actual response was, sure??? Being high made this a little easier, but in my head I just kept thinking, “How the hell do I even do this?” I wasn’t a bully in high school. I’ve never given anyone a wedgie before and I’ve heard there is an art to it. But as I was currently a homosexual sexual explorer I decided to dive right in.

It was at this point that I noticed that he was wearing some sort of cheap cotton briefs, like Hanes or Fruit of the Loom. Now I will admit that I have some bougie tendencies, like I will only shop at J Crew proper and not the outlet, and I only wear Calvin Klein microfiber underwear, and for a kid who has a wedgie fetish I was expecting something stretchier than cheap cotton briefs. I get it; you are a college student. So save your allowance or ask for them for Easter or Hanukkah or Kwanzaa (I hear underwear is quite the popular Kwanzaa present these days).

I began tugging on his underwear and he kept urging me to tug harder and harder cramming his underwear further up into his ass crack, and at some point this experience stopped being weird and started being arousing. I'm not saying that I would have wanted to give anyone else a wedgie, but it was a turn on to see how much he was enjoying all of this. As I began working his dick with my other hand, while tugging on his undies with my other it became obvious that this boy was gonna bust a serious nut soon, and bust he did all over my hand, his pants, my pants, and a few innocent leaves. Unfortunately no one brought anything to clean up with so we utilized some grass.

After the experience we both zipped up our pants and maybe kissed goodbye. I believe that he hit me up once or twice after that and wanted an encore, but it never happened. it's not that I was against it, but I think logistically it never really panned out. It was a new experience for me for sure, and clearly something that I will never forget. I think it is important to push yourself sexually and occasionally try things that might freak us out. I still have a lot of fantasies that I would like to try one day, some of which I don't even share with people because I am worried I'll be judged. I think when it comes to sex we need to keep an open mind and appreciate our differences, especially if the things that turn us on don't harm anyone else. Plus, who knows, we might learn things about ourselves in the process.