When I was about twenty years old, my sexual curiosity started to broaden so that it included men as well as women. I was careful about how I worded that earlier part because there had always been a certain degree of curiosity about men.

I wouldn’t say that I was physically attracted to men, or at least the vast majority of men, but I had become increasingly obsessed with their genitalia. In order to disguise my true intentions, I would seek out any sort of pornography that featured women as well as attractive men so that I could shade my true intent if I were ever caught. Transgender women would be my next target. Somehow, it seemed like it was “less gay” to look at them as opposed to men. Unfortunately, many of them didn’t really provide the same sort of thrill that fit, older teen guys did.

Whether it was photos, GIF’s, or videos, I soon found myself consuming large amounts of gay porn. I had to be careful since I still lived with my parents and I had a girlfriend, Jenny.

My experimentation didn’t stop with pornography, though. Several times, I tried inserting my pinky finger into my anus. It didn’t really do much for me, partially because even that felt quite large and uncomfortable. A few subtle attempts to initiate something with male friends didn’t go anywhere either.

One day while surfing a blog site, a thought occurred to me while watching an autofellatio video. If I could increase my flexibility enough to reach my cock, then at least I could know what it felt like to have one inside of my mouth. Even better, I could know what it was like to swallow a fresh load of cum.

I was in pretty good shape, and I believed that the fact that I was quite thin would work in my favor. So, I set out on a new mission to attempt to “get there.”

At first, I tried sitting at the edge of my bed and bending forward. After a few days of trying that technique with an erect cock and my tongue extended, it seemed like I had too far to go and was making little progress. I had considered giving up the mission but instead decided to try a different position.

It took several minutes to finally get into the proper position. Standing on my shoulders as I leaned against the footboard of my bed, I let my body fold over onto itself. It seemed more exciting in this position and I could tell that I was a bit closer. I could still fit my hand between the tip of my penis and my mouth, so I was probably still five to six inches away.

Every day after my college classes, I did my stretching exercises. Progress was painfully slow, but I was getting closer. It took over a week before I was able to just briefly touch it with my tongue extended. That breakthrough only fueled my desire to continue. I tried to stretch for longer, but that position is quite unforgiving on the neck and I had to keep my sessions brief.

It took several more days of training before I finally was able to wrap my lips around the head of my penis. To be honest, it was really disappointing. Without any sort of motion, it didn’t actually feel like much. Some tongue-waggling helped a bit, but I ended up having to basically just masturbate. My cock would pop out of my mouth while I was stroking away and I ended up with as much cum on my face as I did in my mouth.

I was disappointed in the results, but I decided to keep trying for a few more days, at least. Progress was getting very slow, though and I was only gaining a small fraction of an inch per day. Even while bobbing, I was only getting half of it in my mouth.

One day while I was stretching, I had just settled into position when my bedroom door swung open. Jenny had decided to make an impromptu visit and apparently, my mother let her in.

“Oh, God! What? That’s so disgusting!” I heard Jenny shout.

I really didn’t know what to do at that point. Dismounting usually meant doing a very ungraceful cartwheel. Instead, I elected to stay put for the moment.

Infuriated, Jenny charged toward me. She grabbed onto my hips and started to force me downward.

“I hope you like sucking your own dick because you don’t ever have to worry about me sucking it again!” Jenny barked.

I could tell that she was both disgusted and angered by my actions. The strangest part, however, was that she seemed to respond as if I had cheated on her.

As she angrily forced my lower half downward, she inadvertently started to thrust my cock in and out of my mouth. It was the sort of motion that I had been seeking all along. I didn’t realize how deep it was going into my mouth until two separate things happened almost simultaneously. I felt something occasionally bump against my nose and my upper lip, and I soon realized that that object was my balls. I had finally gotten all of the way there! A side effect of that achievement was that my cock was briefly beginning to trigger my gag reflex while at its deepest point.

I decided to enjoy the experience and I started to suck on my cock as Jenny force-fed it to me. It didn’t take long until I felt a hot blast of cum against the back of my throat. As cum quickly filled my mouth, I hurriedly tried to gulp it down, but it wasn’t easy to swallow at that angle. Cum was already spilling out of my mouth before I managed to gulp down a large portion of it.

I’m not sure exactly what tipped Jenny off, but she suddenly realized that I had just ejaculated. Perhaps it was the gulping sound or maybe she saw the thick, white liquid leaking from my mouth. She also had a direct view of my backside, so maybe she saw the pumping of my prostate or the tightening of my balls. Either way, she was done at that point. She released me and stormed out of the room.

I cartwheeled to the floor with a crash and called for Jenny to come back, but she didn’t. Despite her threats, I wasn’t convinced that our relationship was definitely over. I was, however, going to need to have a very uncomfortable conversation with her soon.