This one is going to hit more in the feels for me. I still feel bad about how everything played out. This is probably more of a confession than a gonewildstory, but there are hot parts to this story if you read it all the way through. I was inspired recently to finally write this all out.
It was the late 90’s and early 2000’s in NJ. I was always with the punk and alternative cliche. I wasn’t really one of them truly, I floated from group to group like a feather in the breeze because I did sports, band, science clubs, commission art and had my own metal bands. I never really fit in anywhere or identified with anyone else strongly, so it made sense that the “friends” I spent the most time with were misfits. It was a strange time when you couldn’t make fun of homosexuals anymore, but people still really understand their place in society yet. Queer Eye For The Straight Guy hadn’t even come out yet. “Transexual” wasn’t even a term most people knew about. They were just “crossdressers” to most people. To Wong Foo, Rupaul, and Meshach Taylor from all those 80’s movies were the only exposure that most people had any experience with.
A number of sexually fluid people ended up floating into the same group as I did. I never really fit in anywhere, and their troubles definitely struck a chord with me. I gave them a lot of public support, and it became a running joke where they would count how many minutes before someone that didn’t know me would just assume I was gay just because of who I was associating with. Bowen often corrected them before I did. Bowen was a long time friend of mine. I hesitate to label Bowen, because I am not sure he even knew. He was as feminine and as gay as they came, but he was deep in the closet.
His parents were strict Chinese from China. Even he never knew how they ended up in NJ and gave birth to him a year after moving there. He pretended to be straight for them. He even had sex with two girlfriends that were daughters of his parents’ friends. My ex even dated him briefly, and she realized his struggles and just tried to be his friend. She was his cover until she started dating me. She moved back to Mississippi, and Bowen and I remained friends. Bowen confided in me a lot. Even when our town redrew district lines and he went to another town’s school, Bowen never made any other real friends. He would tag along with me and talk to the other gay, lesbian and whatever outcast was was around. He didn’t really get too close to anyone. There were a million red flags that I should have seen that would have told me he had a crush on me, but I was oblivious.
I was the one that found us female friends to help him find feminine clothing. I was there when he came out as gay to his parents. He crashed in my basement when his parents kicked him out and disowned him. I found him a place to live with an older lesbian that was good friends with one of my young lesbian friends.
Bowen was gay, but he had never gone beyond kissing other men until his parents disowned him. That was until me. We are fastfowarding until Bowen is now comfortable being gay in public and wearing women’s clothing. Without hormones, he passed as female better then some actual girls I was friends with. Makeup and gym training to emphasize womanly proportions helped him a lot. He was only around 5’5″ and track runner thin with long black hair. I think he was trans at this point, but he never wanted to be labeled as a woman. He didn’t even like the term crossdresser either. He was just a gay boy that liked women’s clothes if you ever asked him about it.
Bowen still had hard times feeling alone. It was awkward when we were younger, but I got used to Bowen wanting me to hold him and let him cry into my shoulder or just lean against me. He never took it to an uncomfortable level for me until I had a really bad night after a breakup. We hadn’t seen eachother for a while since I was away at college. My girlfriend during my first year of college and I ended our relationship in a huge fight, and I always would get stuck in my head after a relationship ends. I could date someone for a couple weeks, split, and move on like nothing. If I really started loving someone, only to have them betray me, that’s when I would start dwelling and start to believe women would always use me, mess with my head and never really love an ugly guy like me.
I’m drunk and crying and Bowen is there holding me. It was probably a funny sight, this petite Chinese transgirl holding this big, burly NFL lineman looking guy while he cries. I spouting “no one will really love me” and “no girl really wants to have sex with a guy like me” left and right. I knew better, but I was drunk and dwelling in a bad place in my head.
Bowen is massaging my shoulders and arms and laying me down on the couch trying to get me to relax. I’m too drunk to fight and really only lucid every other minute. I am near blackout, and I suddenly realize Bowen is giving me a slow and sensual blowjob. His hair pushed all to one side, so I could see his face as he blew me and looked at my eyes lovingly here and there. I blow my load down his throat, Bowen never lifting his mouth away from me. I pretty much pass out at this point, Bowen crawling up to lay inside my arms on the couch.
Bowen was already on another recliner watching TV when I woke up. I was hung over, and I had to piss so bad that I just raced to the bathroom. Everything didn’t really click until I had a full glass of soda and sat back on the couch staring blankly at the TV. All I got out was something like, “Did last night just really happen?” before Bowen stopped me. He said he knew I was straight. He just wanted to do something for me to make me feel loved in that moment, that it was his first time giving someone a blowjob, and just wanted to try it out. He said it didn’t have to be anything serious, he just wanted to try it out and nothing had to change between us.
We both just carried on like nothing happened for a while. Inevitably, he’d come out and ask me if he could blow me again every once in a whole when I was down in the dumps and not dating anyone. I politely refused the first few times, but I just let it happen eventually. My dick was like his new play toy, and he wanted to be the best at it. I probably should have stopped him. He never branched out and met other gay guys. We were still young, and this was his time to learn how to meet and date other men. Instead, he just hung out with me whenever I wasn’t busy and took my scraps. I was sexually pent up, and a blowjob was just a blowjob. I wasn’t touching his dick, so I just imagined it was another girl. I kept making sure he knew I was still into women, and I might find another relationship at some point. He kept saying he knew and he was ok with it.
The hammer really hit the nail on the head when Bowen was dressed slutty for the first time blowing me. He had on a thin black choker, a small torn Korn tank top and a black fishnet shirt over the tank top. His makeup was like any high dollar escort with a black and white plaid skirt emphasized with a metal studded belt. As he blew me, it turned into a conversation about him wanting me to be his first. He had been with women, but he never had a man penetrate him before. I reminded him that I wasn’t comfortable returning the favor, and he said it was fine. He had already been using flavored lubes for blowjobs that he got from places like Spencers, so he already had me ready to go. He had a black thong under his skirt, and slid it over with his one hand as he used his other hand underneath him to position the head of my cock.
This was my first time penetrating anyone anally, and I remember it seeming like it was so tight. He lowered himself slowly down on me until his back was resting on my chest as I sat on the couch. It was just so tight, that I let him do the work at first. We were both moaning slowly as we adjusted to each other. He began rocking back and forth more, and I began really thrusting at this point. He balanced against me with one arm and reached down to pull his own cock out to stroke it. I had my hands tight around his hips as he came all over himself and his clothes. He was like a lifeless ragdoll as I pumped into him from underneath until I unloaded into him. We just sat like that for a while. Probably 5 or so minutes later my half erection that never went away was fully hard again, and he just started rocking again. I lazily fucked him like that on repeat for what was probably a good hour or two until I had to pee. He spent some time in the bathroom after me and shower, and hid in his closet to change into a large nightshirt while I showered after him. We both went to his bedroom and slept with me holding him. I was kind of ready for round two in the morning, but he told me he was too sore and just wanted to be held.
We went on like this for a few weeks. Two or three times a week. It was mostly the same, but sometimes he wanted it rougher. We would be on his bed, and he would have me take him doggystle as I gently pulled his hair back. We never really made out, and I never interacted with his dick. He began cuddling into me more and more when we weren’t having sex.
I was going back to college for my second year, and I had to clear the air and figure out what was going on. Too often in my life, I just kind of go with the flow instead of manning up. Bowen already knew about my plans, and I asked him if we were going to just stop this when I leave because I would be going away to college right after that summer. Bowen got a bit upset and asked me if there was ever a chance we could still hook up. I explained to him that whatever this was, I was still straight and wanted a wife and family with kids that were my own. I was young and thinking too much about myself; I didn’t know about women being surragates and all of that yet or things like polyamory and perhaps dating him and woman too. My world view was smaller. I figured he would find the right man for him, and I would find the right woman for me and we could just go back to being the same friends that we used to be.
Bowen was upset, and he told me to leave. I tried telling him all sorts of things you would probably expect to tell someone so they won’t cut you out of their life without comitting to them entirely. I tried calling, messaging him on AOL Instant Messanger, and texting. He never answered me. The older lesbian woman he was staying with eventually told me he ran off when I returned from my second year of college. He did send me a text eventually saying he was in California and safe, but he had to figure things out. He eventually changed his phone number, and I never heard from him again. It was another friendship I lost because of sex, another regret for me. I already wrote one gonewildstory about that sort of thing with another girl.
It’s funny, years later, I watch a lot of transexual porn, mostly featuring transwomen with ciswomen. I am more mature and open minded I guess. I’d be open to being with a transwoman again, but my fiancee isn’t into threesomes nor transwomen. I love her to death, so I’m willing to forgo these desires and just read about them and watch them online these days.
Source: reddit.com/r/gonewildstories/comments/9adhnc/mt_a_long_story_about_a_friend_that_i_still_think