Early cross-dressing experiments

I first started to masturbate when I was around 12 years old, though curiously enough it wasn’t in a way one would normally think about it. I liked girls… a lot, in spite of my lack of success with them. I found the female form intoxicating and mesmerising. When we lived on the islands when I was little I used to imagine going through some sort of secret base and coming out on the other side transformed as a girl. As I grew into adolescence, I took this on a step and… am not entirely how it all started, but I used to secretly grab some of my sisters clothes… their tights, bras, panties, dresses… put socks into my bra to make it look like my tits… I don’t know, but I guess it was something about the material as well that felt extremely sexy, and definitely got me very excited. In my bedroom, I would dress the quilt up as a girl as well, imagine that we were both women having fun with each other…. I’d basically hump the quilt until I came.

I never imagined being with a guy—only other women, and I did think a lot about the idea of becoming a woman. I guess at the time though the medical technology was not quite as advanced as it is now otherwise, who knows, I might have given more thought to it.

When I was 13, I went to my second high school, and that was a boarding school, so it was pretty hard to dress up while I was there (I can imagine the reaction of the other kids if I were ever caught!). Though, whenever I went home for weekends or holiday, I would do it whenever I could. Eventually, to avoid having to sneak into my sisters’ bedrooms when they weren’t there, I took some of their clothes that I didn’t return and that I kept it all hidden behind the drawers in my wardrobe.

Once, I remember at around Christmas time, I must have been making a bit too much noise on the bed as I remember my mum shouting up to my room from the living room, telling me to stop whatever it was I was doing as they were trying to watch TV… Another time, I was really needing to do it, so I went quickly into my sisters’ room and got changed there quickly, not realising that one of my brothers was in the room below. He heard my footsteps above him and went running up the stairs shouting, “What are you doing in her room?” I was in panties and a silky dressing gown, so pretty obviously I didn’t want him to see. In my panic I shouted out for him not to come in as I was naked… not really much else I could say.

I never admitted to anything, though of course there were suspicions about the clothes going missing. Who am I kidding?! They must have known! Just nobody ever said anything to me. I remember one of my sisters making a snide comment about gay people dying from aids, probably thinking that if I was cross-dressing, I was gay… (well I would have been, I suppose, just not in the way that she thought!!). It was ironic that that particular sister was a huge fan of the Freddie Mercury, who had died just a couple of years beforehand.

By the time I was 16 though and started my third high school, I kind of… stopped. Am not sure if it was because it was “just a phase”, or if I did just suppress what I really wanted to be… The fantasies of being with women and more than one woman remain, though I guess now I am much happier with who I am than when I was back then… and I do not have regrets about the way it all turned out. I guess that the thought of any sex change operation now would never get any of my attention, though I do sometimes think “what if?”.

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School years – the start of it all

By the time I was 13, I was pretty much on the verge of some sort of breakdown: another kid just needed to look at me for me to burst into tears, and they knew it. One of the worst moments came when I was 12 and pissed myself in class as I was too afraid to ask to go to the toilet.

After growing up on sparsely populated islands, moving to the larger city of Lancaster in the north of England when I was around eight years old was quite traumatic for me. School suddenly became much less friendly and I struggled to adapt. I would cry a lot then kids would make fun of me… it was like a vicious circle…

I remember well when it all started: I was at primary school when I was eight, and two of my older sisters who were at the same school suddenly weren’t there on a particular day—they were on a school trip. In the playground I started looking for them and couldn’t find them, and I remember starting to cry because of it. This caused some amusement with the other kids who laughed at me, and that in turn caused me to cry more… I remember teachers telling others in the class about people with “thinner skins” who were more sensitive than others… that didn’t work, for sure.

I swiftly became known as a “cry baby” as I literally was crying at school at least once a day and more often than not, two or three times. This was something that continually inspired others to make me the brunt of their jokes. Other things like an accent that was completely different from that of Lancaster didn’t help: I was seen as the posh kid, which helped to further put a target on my head. Understandably I guess as kids can be cruel to an easy target.

This would continue for years. By the time I was 13, I was pretty much on the verge of some sort of breakdown: another kid just needed to look at me for me to burst into tears, and they knew it. One of the worst moments came when I was 12 and pissed myself in class as I was too afraid to ask to go to the toilet. The teachers understandably became tired of it and rather exasperated by it all, and I don’t think anyone in my family really knew what to do. The only solution that was came up was changing school. And indeed, two primary schools and three high schools later, by the time I was 17, I was only just starting to get that mystical “thick skin”. Still seen as strange and alone, with zero confidence to really speak with people… but… at least I wasn’t crying all the time.

In the midst of all of this, I remember when I was ten not being interested in girls, though that swiftly changed when I turned 11 and went to my first high school. In spite of being deeply unpopular and certainly not cool in way whatsoever, I became infatuated with a girl two years older than myself… so much so that I saved up my pocket money to buy a £10 ring for her at a jewellery store. We all got on the same school bus and she lived quite close to me. One day after we got back, I went to my place via hers to knock on her door and give it to her. Needless to say, my affections were not returned, though at least the ring was given back a few days later.

What this is all about and why…

…Even at that time, the period has been marked by transformation. Curiosity and expanding on my own sexual boundaries. Depression, yes; highs and lows for sure; dating with apps in a major city; paranoias and insecurities and a struggle between a self that has two sides…

I’m Ben. I live in a city in Brazil and am in my mid-thirties. I divorced (well, separated, to be precise) almost a year ago. It was the culmination of a marriage that, like many I guess, started off with plenty of passion and love but, as the years went by and the last two years in particular, transformed into the routine. With sex about once every month at best, and neither of us with the courage to talk about it, I ended up cheating on her with a girl in another town—an affair that lasted a good three months or so before my then-wife found out, and which continued another couple of months before it came to its end.

Even at that time, the period has been marked by transformation. Curiosity and expanding on my own sexual boundaries. Depression, yes; highs and lows for sure; dating with apps in a major city; paranoias and insecurities and a struggle between a self that has two sides—one, hopelessly romantic and dreamy, looking to find a girl to fall in love with; and the other: lusty and looking for adventure, enjoying sleeping with different women and wanting new experiences and fulfil fantasies. Two sides that find it very hard to mutually accept each other: If the romantic side is “winning”, the adventurous side feels discontent, thinking that missing out on so many things. If the adventurous side starts to get the upper hand, the romantic side starts feeling lonely, struggling to find some sort of meaning it all.

So I decided to write this, not as anybody pretending to be an expert in relationships, nor as anybody who is proud about their way of life (au contrair, I often despise everything about me)… but I guess as someone, like many others, who is messing and muddling their way through life; struggling to enjoy the experiences and what there is on offer and not fuck everything up at the same time. Who knows if this might even help a little others who are trying to come to terms to themselves, their own past, their own wants and desires.

The experiences I have had, and continue to have, are all very new and, while occasionally very superficial, they can be and have been exciting. At the same time, they have often left me just curling up in a ball, just wanting to disappear by whatever means necessary. Swing clubs, prostitutes, porn and sexting; obsessive flings and feeling the danger of getting obsessive; being in the position of liking someone more than they liked me and dealing with those horrible insecurities when she doesn’t text back… and then the opposite….

At the same, a childhood… a past that continues to affect me; a walking contradiction… looking to escape loneliness but then wanting to be alone… Dealing with and enjoying the thrill of being liked by someone or having that amazing first date… but then the crashing disappointment when it all becomes too apparent that it’s not going to work out. I think that some of this will ring with a few people and there and it will be interesting to know more about the experiences of others and how others have dealt with their problems… Who knows if this whole thing will even help me get a grip of myself. I guess we shall see.

Please bear with me though – this blog is just starting, though I have been thinking about this for a while now and have plenty to write about, so I hope you can follow as the story develops.