I’d still love to hear your response, Thane. I also want to hear more about what the others have to say on this subject!

@ Thane:
That was a fascinating read! And it’s nice to hear some of my own experiences mirrored by someone else. One thing that really stuck out to me was that you said about how it may have seemed common for young girls to be into slash, but it was something that had more profound meaning to you and something you ultimately took further. Sometime during the grey area between boyhood and my transition I was worried about the validity of my attraction to lesbianism. Lesbianism is hugely popular, especially amongst boys. But it aroused a romanticism and emotionalism that I couldn’t even get close to reaching as a boy, and realizing that helped me progress.

Also, would you venture to say that your periodically masculine role during sex could be called autophalliphilia? Haha, I’m hazarding a guess at how that would be spelled. The opposite, of a sort, of autogynephila? I am NOT trying to be insulting. It just popped into my head as I was reading.

I’m happy for you and your partner! That’s hot. People who find such open partners are so lucky! I half think they’re faerie myths!

I can relate a lot to what Cassandra is talking about, honestly. I remember being an innocent thirteen-year-old wanting to explore my sexuality, and the internet seemed to be the best place to do that. I want never into Second Life or Habbo Hotel or WOW or anything like that, but I became increasingly interested in text-format roleplaying, both in communities and forums, and one-on-one with friends and strangers.

[I should probably start by introducing myself a little. ;D I believe I'm "bigender" - there are parts of me that are male-oriented and parts of me that are female. I identify as female, though there are parts of me that are definitely more masculine and I have moments where I feel more like a guy than a girl, which I embrace just as much.]

I did a lot of roleplaying online, mostly slash (guy-on-guy), and it definitely appealed to me a lot more than anything heterosexual or girl-on-girl. And I know what you’re thinking – I was a thirteen-year-old girl, of course I loved slash! Don’t all girls that age enjoy making pretty men “get it on” with each other? Actually, for me at least it was a lot deeper than that. There was something super appealing about being a guy, or pretending to be a guy, and not only in the sexual scenes but in other forms of roleplaying too – casual day-to-day scenes, workplace environments, social gatherings with other guy characters, that kind of thing. I particularly enjoyed playing a guy around other girls, turning the tables on real life and playing for the other side, so to speak.

At first, my male characters were more effeminate. However, as I delved deeper into their minds and focused more on how men act in real life and movies rather than how thirteen-year-old girls tend to make them act in various fanfictions, they became more realistic and three-dimensional. They became less perfect and pretty and effeminate. I began to really get into them and their quirks and habits, and soon the guy-on-guy slash addiction expanded its horizons to het as well, with myself playing the guy.

Like Cassandra, I tended to put distance between myself and the communities of immature teenage girls who just wanted their pretty boy characters to fuck each other’s brains out and cheat on each other time after time, and joined groups of mature writers who wanted to focus on character development and plot. I tended to make my boys less perfect and pretty, and give them imperfections, like short bitten nails, rough skin and greasy hair.

My main original male character, who I’ll give the codename Damien right now as I’m writing a novel about him right now and would rather not use his real name, was a typical teenage boy who refused to shower often and wore yesterday’s clothes and skateboarded and had hair you could fry chips on. For some reason, I really enjoyed delving into the gritty, imperfect, unhygenic stereotype of adolescence that seems to be socially acceptable for boys but definitely not girls. In real life at this time, I was picked on relentlessly for looking too much “like a guy” and being “unclean” – we wore uniforms at my highschool, so I would wear a huge baggy boyish shirt over a Quicksilver or O’Neill tee, baggy uniform pants, and hiking boots. I never wore make-up and I didn’t shower every day like the rest of the girls in my year. It was strange to live a cyber-life where people were seriously attracted to these scruffy, gritty qualities in my male character that people were disgusted with in my real life female self.

Like Cassandra, I explored a lot of different avenues with my roleplaying – things that, like Cassandra, I would now be embarrassed about. BDSM, non-consentual, polyamory, DS, beastiality, “knocking a girl up”, and a lot of other things, mostly from the point of view of a male. I didn’t really have any boundaries when it came to my roleplaying and cybering, I would try anything out. And I agree, you can learn so much about yourself during this exploration – what you like, and what you don’t.

Luckily nowadays, I have an amazing partner who is just as excited as I am if I pull out the strap-on or the packer and decide I’d like to be a guy during this “round”. It’s not exactly the same as doing it online as there is a lot of preperation and a lot of imagination involved, but I have to admit it’s definitely a lot more exciting and fulfilling to actually act the part of a man IRL than to just type it on a keyboard and do everything in the imagination.

Emily touched on it, and I just wanted to emphasise it, that the Internet is a vastly powerful tool in exploring one’s identity, be it gender or otherwise. The Internet is sort of a double-edged sword in how much potential information and freedom it offers you, and people don’t always do the right thing with freedom, and they don’t always explore their identity prudently. I certainly made my fair share of mistakes on the Internet. Then again, we have to be able to make mistakes. That’s part of growing. I just hope the Internet isn’t harnessed and tamed like so many companies and politicians want to do. It’s depressing how afraid people are of freedom and uncharted territory. But that’s a discussion on human history and not sex! So, back on topic…

Like most young Americans, my early teens were heavily influenced by society’s suppression of natural sexual behaviour (puberty exists for a reason). The Internet put me way ahead of the game. I got sexual experience, even if virtually, a lot earlier and a LOT more safely than I could have otherwise. I started out in little chat rooms and such like many people, usually in some fantasy roleplaying context. I’ve had a strong artistic bent and would later become a writer, so it was a great time for me, but it was hilariously clunky as you might expect expect one’s first forays into sex might be.

Gender didn’t come into the equation until college. By that time I’d already found out that fantasizing sex as a boy and actually going about it in person were two different things, and the latter was impossible. I never, ever got that close to any girl. No matter how badly I wanted to have sex, I just couldn’t do it as a guy. It just felt wrong.

And this was many years away and apart from all that silly chatroom roleplaying. A friend turned me on to massively multiplayer online games, some of which had a significant roleplay element. These worlds were much more interactive, and the groups I would hang out with were very mature, intelligent people. And for the first time, I found myself playing a female character. I think this was important for my transition later on because, while I felt much more at home as a woman, I made lots of silly goofs, like acting too cutesy or ditsy or doing any number of things I thought a woman should act like — without taking much note of how women actually act. This also sort of proves how powerful our socialisation is, because it rarely ever matches up with reality.

As time went on, I got to explore this role more intricately, and that included sex. After a while, this branched into tons of avenues. Polyamory, D/s, beastiality, transformation, and I can’t even remember what else. I got to touch these ideas safely and explore them and say “Hey, I really liked this.” Or “Hey, I think this will be best left as a long distant memory!” Or “Hey, I liked this, but it’s only a fantasy-land thing. Not for me in ‘real’ life.”

There was a flurry of sexual exploration due to this freedom. I have long since “chilled out” and am pretty disinterested in or even a little embarrassed by some of the things I dabbled in, but I don’t regret it. I learned so much about not only myself but about people in general, and how much people feel they have to hide certain things about themselves because of social norms, and how sad that is.

One thing that stuck with me, though, was my introduction into what the Japanese call futanari, which is an enormously popular concept in their hentai (animated pornography). Girls with penises! There are many different forms this can come in, but the notion that there is a large segment of humanity that finds girls with cocks desirable was pretty wild. It didn’t have much to do with my gender exploration, but it’s something I’ve liked ever since, and I’m glad I was exposed to it.

These days, I don’t really do much on the Internet, sexually. I read erotic literature from the internet all the time, as I don’t have a partner, and I have a very good couple of friends I write erotic literature with or roleplay with erotically, but not often. Not as often as I’d like, certainly! I’d much rather be having sex with another person in “real” life, obviously, but it’s a serviceable alternative in the sexual doldrums of transition life.

I remember in my early stages of transition, using the Internet to explore both my gender and my sexuality. One of the first venues I used to present as a girl was on Yahoo! Games. I’d play games, mostly pool, with random people on the internet, and with a few people, regardless of gender, we’d end up cybering in a private chat space. This was long before the days when SL existed!

By the time I got to trying out Second Life, I was already long since living full time, and I was also in a relationship. At this point, I didn’t really need to explore my sexuality online so much, since I could explore with my partner. For me, it was much more fulfilling this way, too!