I never felt more bisexual

A bit of background first.

So, I (M, 30) have been in a pretty deep self discovery journey over the past few years. It all began with me listening to my then girlfriend (soon to become wife) talk many times over about the fact that she would like to try sex with other girls. Over time, that made me feel safe enough to question my own sexuality, and ultimately sent me down a long path of asking myself if I felt the same way about other men.

In parallel to that, I began to feel more and more curious to truly know what women felt during sex. I asked myself: how must it feel to be penetrated, or to have a vaginal orgasm? I have never not loved being a man during sex with my girlfriend, but at the same time what she felt seemed so fucking great and so different from what I felt… It was alluring, and I began to really want to have a taste of that, in addition to what I already had.

I eventually figured out that the best way to pursue this would be to engage in anal play, and so about 18 months ago I bought my first buttplug/prostate massager.

Over the following months I developed an on-and-off relationship with the exploration of both my desire for other men and my anal pleasure. Occasionally both paths would cross and I would fantasize about sucking cocks while playing with my prostate massager, but for a long time these two pursues would remain kinda blurry and uncertain. I would sometimes feel the urge to go back to them, but the pay off was never that great. Why? Well…

As I’m sure lots of guys who play with their buttholes/prostates will be able to ascertain, the first few months (or years) of that can be really weird. There’s lots of physical discomfort, plus the anxiety of doing something that’s still socially perceived as “wrong”. Not to mention the fact that the pursuit of anal pleasure is in itself totally different from the penile pleasure that we’re generally much more used to. Thus, it normally requires lots of rewiring before it truly becomes as wonderful as it can be. So there is, by definition, lots of frustration involved.

Aaaand as I’m sure lots of bi/pan folks will be able to ascertain, figuring out your attraction to different kinds of people can be very confusing as well. If you grow up and live most of your adult life perceiving yourself as straight (as was my case), even if you’re very open minded and willing to try new things (as was/is also my case), it can be hard to understand, for example, what’s just a kink and what’s truly part of the foundations of your sexual identity. It must have been 3 or 4 years from the first time I jerked off to the picture of a naked guy to the first time I felt like it was really ok to consider myself not just a bicurious kinkster, but truly a bisexual man.

That happened about 6 months ago.

My girlfriend and had I spent the first few months of lockdown living together in an apartment, a period during which the sex was pretty boring to say the least. We had been planning to move in together for a while, but this was a forced situation, as we temporarily had to go live in a place that we kinda hated, as part of a larger scheme with our families to isolate/protect our parents from the virus. Not to mention the fear caused by the pandemic itself. Both our libidos reached their lowest points during this period, but at the same time, this situation allowed room for something else to start brewing inside of me.

In July things changed, and both of us had to go back to our parent’s houses, and back to only sleeping together on weekends. And as much as I felt strange going back to sleeping alone on most nights, I now had room to experiment with myself again. I soon went on a sex toy frenzy, got myself a dildo and a vibrating prostate massager. And at the same time, I started spending more and more of my alone nights browsing gay NSFW content, mostly here on Reddit.

I had never been more aroused by male bodies, and soon this became my primary source of solo fun. For the first time ever, I began to play with the fantasy of being penetrated by another man, something that, in spite of all of my previous explorations, had never been on the menu before. My ability to identify other men as sexy and desirable grew, and at the same time the sex with my girlfriend became good again. Not mind boggling or super creative, but definitely way better than it had been during our time in that dark, stinky apartment. We had a streak of great talks about sexuality over a few weekends, and those helped me come to terms with the fact that I would now prefer to call myself bisexual than straight or even bicurious.

This was a huge moment for me, and I made sure to come out to a few LGBTQ+ friends, who showed me their full support.

On the prostate front, however, things were not evolving as much. I was still too eager to get something out of it, which, as I later found out, is the worst possible mindset for this kind of play. I did get some more pleasure from the vibrator than I was getting before, with just the butt plug. But it was nothing that could really help me reach the unthinkable pleasure I had read everyone writing about, so I quickly forgot about it.

And as for the dildo, I had really high expectations for it, as it was, unlike the other toys, an object that I could thrust in and out. Who knew, maybe that was the one thing that I was missing that the other toys were unable to give me. And so I had one session with it… That was totally ruined by eagerness and anxiety. The pleasure it gave me was by all means not worth the discomfort it caused. I threw it in the dark depths of my wardrobe as I thought to myself “why do I even spend money with this kind of shit? I should throw it in the garbage can before someone finds out that I have it”.

Thank. God. I. Didn’t.

But I did deliberately forget about trying anything with my anus. Maybe that was just not for me. I went back to practicing just regular masturbation.

So there I was, considering myself a mostly closeted bisexual. Jerking off mostly to naked guys when I was alone, having mostly good sex with my girlfriend on weekends, and so on… Occasionally I would be visited again by the fantasy of being penetrated by another guy, to which I would not pay much attention anymore.

But eventually the frustration with my attempts at anal play started to bleed into my desire for other men, and so my fantasies began going back to being mostly straight, mostly vanilla, and I began to question again if I truly was bisexual or if that had been just me overestimating my kinks. I almost felt bad for coming out to my LGBTQ+ friends, and so I was back to my boring initial state. Not that there’s anything wrong with straight or vanilla fantasies, I get a lot of fun from those as well. But after all that I had been through, I began to feel as if a large part of my sexual self was missing.

Until last week.

On Sunday I had another of those talks about kinks and sexuality with my girlfriend, something which hadn’t happened in months. She wasn’t super into it this time around, but I really felt like we needed to fire things up again, so the talk gave me just the motivation I needed. I went back to my place on Monday morning absolutely determined to reanimate my full sexuality. And the first thought that occurred to me was to try and wear my old buttplug more often.

You see, on my first attempts at using it, I never really thought about exploring the sensations I could get from it as a whole. I simply put it in before going to bed, tried to reach an orgasm with it for an hour or so and then got bummed for not being able to.

Not this time.

This time I thought “why not wear it during the day, so that I can truly understand how my body reacts to it in different situations? I’ll be able to feel it while sitting, standing, working, walking, and maybe that will give me some ideas”. And so I did it, and it couldn’t have been better. Not only this approach allowed me to get a better understanding of what the plug could do for me, it also allowed me to understand what parts of my anus were more sensitive to pleasure. Also, there was a bonus, and a pretty nice one.

On that evening, I put on the plug after finishing my work hours, and wore it until bedtime. That’s when the magic slowly started happening. When I took it out before going to sleep, I felt my anus very relaxed and sensitive in good way. So I thought “why not?”, and finally decided to recover my dildo from between the suit that I wear every two years and the snow coat that I’m saving for my next trip to Iceland.

I soaked it up in lube and shifted around with some new positions that I had been reading about and… I finally felt it slide in without any pain or major discomfort. I moaned almost instantly. I started thrusting very gently, but as soon as I found an angle that cause my body to shiver and my breathing to go heavy, I was hit by that old eagerness again, and started thrusting too fast. I soon tired my arm too much and understood that I should stop. But as the dildo came out, it caused nothing but shivers and moaning. I knew I was on to something this time.

Despite still being far from an orgasm, for the first time I felt like I had actually been penetrated in a pleasurable way. I understood that I should hold on to that pleasure, and that caused me to enter a loop where every new thought about my ass, buttplugs or dildos would make me more aroused than before. On that night I went to bed hornier than I had been in a long time.

On the following day I woke up and went immediately to put the buttplug on again. Just one day and this was beginning to feel natural. For the first time I did my workout routine while wearing it, and noticed how some guys on the streets started to naturally get my attention, to which my anus immediately responded by clenching around the plug. Another thought I added to my feedback loop of arousal. I felt some soreness after taking the plug off though, and decided to give my ass a break until I felt like it was ready for more.

And to my surprise, that didn’t take long. On the following morning I spontaneously woke up two hours before my usual time, craving anal stimulation. So I put the plug on again and tried to go back to sleep. When the alarm finally went off I noticed there was nobody else home, and so I decided it was time to give the dildo another try.

I sucked it for a while to build my arousal, and then slid it in again. It was way easier this time, as I already knew the best way to do it, and so I managed to get even more pleasure. I decided to try thrusting with it while listening to this sissy roleplaying audio that I love to go back to every now and then. I imagined the audio combined with the dildo would do the trick, and… It did some trick.

The thing is that the instructions in the audio didn’t exactly sync with the pacing that my body was asking for, and because of that I missed the right build up window towards a potential orgasm. This information was gold, however, as it made me understand that it was all about pacing, and specifically paying attention to what kind of pacing my butthole was asking for at each given moment.

In addition to that, the audio itself really reanimated both my fantasies of feeling what a girl feels like during sex and of having sex with other men. From this point on I began to desire men like I never had before, and began to fantasize about having a stud do everything he could to me. I began to put real thought into what kind of male bodies attracted me the most, and to build a collection of pictures of lean and muscular naked men, all with hairy chests.

I was in an incredible mood as I went to make my breakfast, like I had had a real morning fuck. I spent this entire day extremely horny, and went at it again when night fell.

This time around I decided to try this other position that I had read about, lying on the floor with my legs resting on my bed. I was also much calmer and more patient, and finally had reached a mindset of just wanting to have fun with my dildo, instead of using it to get to a specific place.

After building my arousal by looking at pictures of naked men and clenching my ass around the buttplug, I inserted the dildo and slowly searched for the right spot, and then started slowly thrusting, just enjoying the sensation of having a cock go in and out of me. Then I started moaning loudly. Then breathing heavily. Then shaking with my entire body. Then feeling like I was about to implode and explode at the same time. Then just wanting to feel my dildo rest over my chest as I felt incredibly relaxed and happy.

For the first time ever, I had cummed from being penetrated.

Actually, I wasn’t even sure if I truly had cummed. It felt earth shattering, mind boggling, and so different from anything I had previously felt that I wouldn’t know how to describe or catalogue that sensation. And that was pure bliss. And I surely knew that I had reached a turning point in my sexuality, where, whether or not that was an orgasm, I would surely try to go after it again and again.

I went to bed feeling very aroused and very feminine.

On the following morning I noticed that, in spite of having spent almost an hour thrusting with a 7 inch dildo in and out of my ass, I didn’t feel any pain or discomfort at all. That thought made me even hornier, but I had other plans for the day, so I decided to give my butthole a night off.

When the next day came, though, it was Friday, and I knew it would be my last night alone before heading to my girlfriend’s for the weekend. At this point I was feeling very feminine with my sexuality, and whenever I thought about sex (which was all the time) I could only think about sucking cock and being penetrated. My straight side was dormant to the point I barely remembered it existed.

So I did things in a very similar fashion to what I had done two days before, except now I had spent the entire day getting signs that my overall arousal was over the roof, such as leaking precum even without touching myself, and getting shivers of pleasure while working out without the buttplug.

When the night came I went to my bedroom and started having fun as usual. I fucked myself with the dildo while just closing my eyes and enjoying the thrusting. Before I knew it the orgasm came, and I happily confirmed that what I had had the other day had in fact been one.

But then I slowly resumed thrusting, and another one came. And another. And another. And I must have cummed 5 or 6 times before finally thinking I couldn’t take it anymore.

In addition to all the physical pleasure and relaxation, I felt so girly and so slutty. I felt like I had finally reached the point of understanding what my girlfriend felt like during sex, in addition to finally reaching a mental state of enjoying every aspect of the fantasy of having sex with another man. This was a simultaneous culmination to both the exploration paths I had started years before.

And then I went to bed thinking about my girlfriend, about how she was partially responsible for all of this, and wondering how it would feel to meet her again on the following day, having spent the week exploring my feminity and my homosexual fantasies with such intensity.

And I had no idea what I was in for.

We met on Saturday afternoon, and already on the way to her place I decided to bring up the topic. She was always aware of my anal adventures, but I still tend to feel insecure talking to her about this after a while. So after a little bit of stuttering, I finally mumbled “I… Was able to get multiple orgasms from just… Anal stimulation”.

She was receptive and didn’t show to be in anyway bothered by it, but it took her a while to start showing real interest. Eventually, though, we both loosened up, and ended up having maybe our best sex talk ever.

I told her my full journey towards the multiple orgasms, including the bits about fantasizing about being a girl and deeply desiring other men. We talked about our mutual interest in trying sex with other people. We talked about how all of this strengthens our relationship instead of weakening it. Eventually we started kissing and grinding. And she was more aroused than I had seen her in a long time.

She was moaning way louder than normal, and acted really slutty as she started to blow me, which is not usual for her. My arousal, too, went through the roof, in a totally different way from what I had experienced over the week. We went to her room and had the best, most intense sex we have had in years.

We felt like trying a new position for penetration, which made it feel better than ever for both of us. Then she sat at the edge of her bed and downright ordered me to sit on the floor as I ate her pussy. She moaned extra loud as she came. Then I climbed on top of her and went for my orgasm, which was intense to the point where I couldn’t stop laughing afterwards. All of this happened within the span of a Miley Cyrus song, and we were both soaking in sweat by the time it ended.

After catching our breaths and talking a bit more we felt like going at it again, and after giving our new position another go, she told me to cum while fucking her doggystyle. I did it, and I was feeling like a fucking animal when I finally proceeded to finish her off by simultaneously eating her pussy and fingering her, after which I knew she would soon fall asleep. And watching her cum felt extra special now.

I couldn’t remember the last time we had fucked twice on the same night.

And as I laid my head on the pillow I started to think about what a rollercoaster this week had been. I had dedicated my time to finding and nurturing the most feminine side of my sexuality and my most homosexual fantasies, and discovered an incredible new world of pleasure from it. And in return, it fueled my masculinity and the heterosexual aspect of my relationship beyond what I knew was possible, instead of somehow denying or casting a shadow over it.

I couldn’t help but feel fulfilled and whole. From the first few thoughts and attempts, these pursuits had been about wanting to expand my sexual horizons and identity, and I felt precisely that: expanded, as if I had added new layers and perspectives to my sexuality and they were now mutually feeding each other.

I have never felt more perfectly bisexual, and I couldn’t be happier about it.

Source: reddit.com/r/Erotica/comments/laab75/i_never_felt_more_bisexual