The years were 2014/15, where a many things happened and one which I began to explore myself more than ever before including losing my virginity.
I firstly began to question my sexuality, something which I had thought about in the past but ultimately put to the back of my mind. All the occasional thoughts of guys I had in the past came back, the occasional not straight porn I gravitated towards to but put off once I was done, and just the little things from growing up that didn’t click in my mind until now.
As I realised I was more bi than straight, I began to want to explore it more, not really knowing at first how to go about it.
The easiest way was through porn, watching anything other than straight including trans porn which I did with a more open mind and found that I actually liked it more than I thought. Not everything I liked, but there was definitely specific types I did enjoy more than others and often wished I had delved deeper into it in the past when I normally dismissed it.
From here I wandered onto ‘dating sites’ or rather more adult type sites and decided to sign up for one just to see what was what. Initially I wasn’t keen on hookups but more or less chatting to other guys and getting a feel for things and how I felt.
At this point I was still a virgin and had never really engaged in sexual activity of any kind with anyone, so the act of doing it was somewhat beyond my confidence, especially as I had, until that point always saw myself as losing my virginity with the opposite sex. Add to that the fact I wasn’t 100% out there as bi to myself let alone anyone else I didn’t want to jump into things too soon.
I ended up occasionally chatting to bi guys some of which where general talking about each other and general chit chat, while others strayed into more sexual talk which I began to enjoy when in the right mood for that kind of talk.
The chatting, especially when it got sexual, slightly improved my confidence in knowing I was bi and wanting to go further. Not could I find the odd guy nice looking physically, but if I really enjoyed it when talking especially about sex between us then I knew I could easily refer to myself as bi, and I could think about what was next.
Eventually come 2015 I was beginning to really label myself as bi, and I began to crave more than just idle thoughts about the opposite sex and sex in general.
I still wasn’t super confident with hooking up with a guy be it as a date or in my case at the time more a desire of having sex, but I was comfortable enough in wanting to do so.
On the same adult site I had been using to chat I began responding to messages away from chat, and seeking out profiles that I liked the look of. I knew I wanted the right person, someone who understood that I wasn’t the most confident guy out there and that I had never had any sexual experiences so I may want to go slow and work up to things.
As expected, some messages I got where from guys who didn’t read my profile and come in way too strong plus there was those who weren’t my type and couldn’t take no for an answer plus those half-way around the world from me.
Once I had sorted out the types of people that weren’t for me, too far away or just assholes I started to chat to someone who fit the bill reasonably well.
I wasn’t immediately attracted to them, but they seemed to be more understanding to what I wanted to get out of my experience and what they would get from me in return.
We conversed a number of times before finally settling on a date and time to meet in person.
As the day drew ever closer I was nervous, not because anything would go wrong, but because I didn’t really know what to do. I had dated a girl for 7 months in my mid-late teens but apart from that I hadn’t dated anyone and as I mentioned hadn’t had any sexual experience.
When the day finally arrived I was excitedly nervous but happy that I took the plunge and was going to be exploring things physically and not just in my head.
Initially we chatted, got to know each other more in the flesh even if we had already known each other from online chats. After a little while when we were both comfortable, particularly myself, things then progress from there.
Being the first meeting between us, we started off quite simply playing with each (HJ) without getting fully naked or engaging in any sex but this was perfect for me.
After we both finished and cooled down/relaxed for a little bit, he left and I sat there not as excited as I had hoped or thought in my mind.
As much as the experience was good the pleasure was not so much there likely as it was my first time so I didn’t know what to expect. Sure everything that happened was stuff I had experienced doing to myself, but with someone else doing it, particularly a guy, that changed the act greatly.
After some further online chatting, a further meeting was arranged, this time things would be taken up a notch.
As the day of the second meet arrived I was a little more excited and a little less nervous
even if i was going to lose my virginity and have sex for the first time.
Again like the first meet, we chatted and relaxed before getting down to any business.
We started slow, playing with each other and during this he leaned in for a kiss which I wasn’t quite ready for so rebuffed his attempt.
Then out of nowhere I had the urge to give my first ever blowjob. Not knowing what to do I made motions that I wanted to perform the act and was given the OK to proceed which I did. I didn’t spend long performing the BJ but once I was done I felt happy to have experienced it and that when I had the urge I also got the confidence to follow through.
It felt strange to me that I was happy to give him a BJ, and do some of the things we had or were going to do but not accept kissing him. I guess the physical attraction to him wasn’t enough to want to kiss but that the sexual attraction was there.
The play continued for a bit and then he communicated that he wanted me to fuck him if that was OK, whipping out a condom for me to use. The though of fucking a guy had been in my mind and I like the thought, but here it was being offered to me and I knew that I was comfortable doing it. I said to myself in my head that even if it turned out not great I would have at least experienced it, and that not everyone’s first time is good.
So as I put on the condom, lubed up a great deal and made sure he was ready, I slid myself into his ass and slowly worked my way up to a good rhythm or what I thought was good. Doggy style was the position as he leaned on my bed and I went back and fourth. After some time I came out and was ready to have some more penis play until we both finished.
Once cleaned up and he had left I sat there, again not as excited about the pleasure but more excited that I even got the confidence to follow through with something that I’d never have imagine would have happened. Here I was having just had sex with a guy, giving him a BJ and fucking his ass and finally being able to say I lost my virginity. It wasn’t a big thing for me to say I’d lost it and it’s not something I cared about, but it was nice to finally do it as a 28 year old.
In the weeks going forward we chatted occasionally but eventually I decided, as much as it was fun having fun with this guy twice, I knew I wasn’t that attracted to him and it was best that if he wanted more fun then I probably wouldn’t be the guy to give it to him going forward.
Moving on from this, I chatted with a few more guys, but nothing more ever came of these chats and I deleted my account on the adult site. The desire to meet guys and have fun was there, but not only did I not find anyone I liked enough but I was wondered if I was happy to just be hooking up for fun and nothing more.
I write this post in late October 2020, and I’m glad I explore my sexuality understanding that I was Bi, and that it was more than a passing thought in my head (I’m maybe now Pan).
I’m also glad that I got the confidence to hook up with a guy and lose my virginity with him. It definitely wasn’t the most pleasurable experience like I had imagined, but the act of doing it more than made up for that, and knowing that I could be confident enough to do things I may not have immediately thought possible (The same year I did a bungee jump when I’m not particularly keen on heights).
This post was not something I was sure I wanted to post, but if you’re reading it then I did posts, so a huge thanks to anyone that reads it.