I like to dress up (part 4?)
Holy cow have things changed since part 3!
I have mentioned most of it on random posts, but I think it's probably best to summarise on a single post and pin it so you don't have to go through the whole timeline.
I did get that new job, which allowed me to make big changes to my life, for a couple of years I remained at my parent's, got a bunch more heels and clothes, which made it increasingly difficult to hide them all. Considering that, and the dreadfully long commute time, it became clear that I had to move out.
By fortunate coincidence, one of my school buds and best friend who already lived on his own was looking for a new place, so long story short, after a few months of preparation, we became roomies.
As you may imagine, I had a lot more chances to dress up then, he often travelled for work, and even when he didn't, he worked on mornings and I afternoons, with different days off too, so I had the flat for myself quite often. I began painting my nails when I dressed up, removing it from my hands after I was done, but often keeping it on on my toes.
It was nice, but after a few months and with my birthday approaching, I decided to take things a step further, so I ordered some very basic makeup stuff online (I had pretty much no idea what to get anyway) , and removed the moustache that I had kept for over six years.
At about the same time I had begun looking for local people with similar interests, hoping to find someone to help me with the makeup, getting some sexual experience as well would be a plus, I thought (I was still very much a virgin then, if you can believe it) but it wasn't a priority.
So through Grindr if memory serves, I met an older (mid or late forties maybe) crossdresser near a cheap motels zone in the city, it was a bit nerve wracking being there first and waiting, but at last he arrived and after a short walk we got a room.
It was not a bad experience really, but way below my expectations anyway, he wasn't any actual help with the makeup, and apart from some fondling and maybe a bit of oral action, it wasn't what I was looking for after all, but at least it was a first step.
I kept looking, had someone over at the house with whom I had my first foray into bondage, but it was a one time thing, still not what I expected. I figured it would be best to go to a group gathering instead of those one on one events, I had been doing some research on cd places around town, but it was a bit overwhelming trying to pick one to go to by myself, and that's when luck came along, I happened to see a social media post from someone (who would later become a dear friend) looking for company to attend a joint called "Natalia's place", so the next night I found myself sitting on a dressing room, getting my makeup done and buying my first wig, then coming up to the second floor to find myself surrounded by other crossdressers (and a few dudes), it was all that I wanted and more!
I was of course pretty nervous through most of it, specially when Electra (the person from the post, who also did my makeup) went to greet and catch up with some of her other acquaintances, but gladly there was someone from the staff that had decided to try crossdressing for the first time that day, so we being both newbies we had a lot in common to chat about, and we hit it off just fine.
It was already a bit late when we arrived, it was a weekend after work, so people started to leave, so in the end it was just me, Electra and the staff person chatting, with a dude lurking around, but leaving us mostly alone. As we were doing some selfies we got pretty close together, so we started rubbing a bit, then that turned to kissing and fondling, there were handjobs given and taken (not reaching an orgasm to avoid the mess, but fun anyway)... Quite a way to end a night of a lot of firsts...
After that I did go to that place a few more times, and to a few others usually with Electra, but not always. I tried to get into a relationship with her, but after a date or two we figured it was only friendship for us, and as such we got into a sort of routine going once or twice a month to another place, closer to her home, I'd bring a dress or two, some heels and my meager makeup bag on my backpack to work, and after I'd meet her on a subway station somewhere in the middle and she'd drive us to the gathering, she'd do our makeup, with me taking over more and more of mine, and we'd party through most of the night, some of the girls would do so for a couple of days straight, or so I'm told, but we'd usually end up sleeping on a couch or wherever at least a couple of hours and leave in the morning.
This went on for a few months, there I met Denise, who I ended up dating for like a year, but I guess I'm doing a part 5 later for that story and everything else after that, since this is already a pretty long post and I should get some sleep, I hope this one makes enough sense.
I have mentioned most of it on random posts, but I think it's probably best to summarise on a single post and pin it so you don't have to go through the whole timeline.
I did get that new job, which allowed me to make big changes to my life, for a couple of years I remained at my parent's, got a bunch more heels and clothes, which made it increasingly difficult to hide them all. Considering that, and the dreadfully long commute time, it became clear that I had to move out.
By fortunate coincidence, one of my school buds and best friend who already lived on his own was looking for a new place, so long story short, after a few months of preparation, we became roomies.
As you may imagine, I had a lot more chances to dress up then, he often travelled for work, and even when he didn't, he worked on mornings and I afternoons, with different days off too, so I had the flat for myself quite often. I began painting my nails when I dressed up, removing it from my hands after I was done, but often keeping it on on my toes.
It was nice, but after a few months and with my birthday approaching, I decided to take things a step further, so I ordered some very basic makeup stuff online (I had pretty much no idea what to get anyway) , and removed the moustache that I had kept for over six years.
At about the same time I had begun looking for local people with similar interests, hoping to find someone to help me with the makeup, getting some sexual experience as well would be a plus, I thought (I was still very much a virgin then, if you can believe it) but it wasn't a priority.
So through Grindr if memory serves, I met an older (mid or late forties maybe) crossdresser near a cheap motels zone in the city, it was a bit nerve wracking being there first and waiting, but at last he arrived and after a short walk we got a room.
It was not a bad experience really, but way below my expectations anyway, he wasn't any actual help with the makeup, and apart from some fondling and maybe a bit of oral action, it wasn't what I was looking for after all, but at least it was a first step.
I kept looking, had someone over at the house with whom I had my first foray into bondage, but it was a one time thing, still not what I expected. I figured it would be best to go to a group gathering instead of those one on one events, I had been doing some research on cd places around town, but it was a bit overwhelming trying to pick one to go to by myself, and that's when luck came along, I happened to see a social media post from someone (who would later become a dear friend) looking for company to attend a joint called "Natalia's place", so the next night I found myself sitting on a dressing room, getting my makeup done and buying my first wig, then coming up to the second floor to find myself surrounded by other crossdressers (and a few dudes), it was all that I wanted and more!
I was of course pretty nervous through most of it, specially when Electra (the person from the post, who also did my makeup) went to greet and catch up with some of her other acquaintances, but gladly there was someone from the staff that had decided to try crossdressing for the first time that day, so we being both newbies we had a lot in common to chat about, and we hit it off just fine.
It was already a bit late when we arrived, it was a weekend after work, so people started to leave, so in the end it was just me, Electra and the staff person chatting, with a dude lurking around, but leaving us mostly alone. As we were doing some selfies we got pretty close together, so we started rubbing a bit, then that turned to kissing and fondling, there were handjobs given and taken (not reaching an orgasm to avoid the mess, but fun anyway)... Quite a way to end a night of a lot of firsts...
After that I did go to that place a few more times, and to a few others usually with Electra, but not always. I tried to get into a relationship with her, but after a date or two we figured it was only friendship for us, and as such we got into a sort of routine going once or twice a month to another place, closer to her home, I'd bring a dress or two, some heels and my meager makeup bag on my backpack to work, and after I'd meet her on a subway station somewhere in the middle and she'd drive us to the gathering, she'd do our makeup, with me taking over more and more of mine, and we'd party through most of the night, some of the girls would do so for a couple of days straight, or so I'm told, but we'd usually end up sleeping on a couch or wherever at least a couple of hours and leave in the morning.
This went on for a few months, there I met Denise, who I ended up dating for like a year, but I guess I'm doing a part 5 later for that story and everything else after that, since this is already a pretty long post and I should get some sleep, I hope this one makes enough sense.
