Letters Continued

Letter #3

When J broke up with me I was devastated. She was my first real, long-term girlfriend. I think I was 28 when we broke up. We are the same age, we were 25 when we met in a poetry class at a community college in Southern California.

"Have you ever dated a woman?" she asked me on our first date. We'd been telling each other about previous relationships and after she'd heard mine, that was her question. She would prove to be my first real woman. She was so good at verbalizing her needs in bed that I became dependent on her. She had the most creative mind I'd ever experienced. We never ran out of fun things to do in bed.

But, I wasn't a very good boyfriend outside of the bedroom. I didn't know what I wanted to do with my life, and I bounced from job to job, taking classes here and there, I even got evicted from the apartment I was renting. She wanted me to be something, and I was so poor that I could never get ahead. She grew weary of my empty promises.

As it happened, as soon as we broke it off, I found a good job where I carved out a nice little role for myself. It was a dot-com business, during the dot-com bubble of the late 90s/early 2000s. Our office was in the City of Orange, part of a massive office complex, and downstairs on the first floor was a food court and a couple of restaurants/bars where the workers would go for happy hour, lunch, etc. I was with a bunch of my co-workers/friends, having drinks one Friday night and J walked through the door. She looked spectacular. I was dressed business casual, and with my friends, she must have been shocked to see me in this light. I looked like a total conformist, like I fit in, like everyone liked me too. She behaved completely differently toward me like she was genuinely attracted and turned on by what she was witnessing.

I took her to my office, showed her around, introduced her to a few of my co-workers, and then I took her down to the file room in the basement and fucked her brains out between the stacks of files.

By then, I had already begun to put the pieces of my broken life back together and I resisted her attempts to rekindle our old flame. It was over a year since we'd broken up. I was making good money, I had a one-bedroom with a ground-floor patio, and a little garden, and I was a block and a half from the beach.

I was surfing and playing basketball just about every day. I was rollerblading, going to clubs with friends, and working like crazy. I knew if we got back together I'd stop all of that good stuff and devote myself to making her happy. So, I never reached out again.

When she first dumped me I went full-blown introvert. It was only a month or so when my friend got me an interview at the dotcom gig and I just worked my ass off, as many hours as they would give me. My bosses liked me and soon they were giving me more and more responsibilities six months into it I was the mailroom manager, then they put me in charge of the file room, and then I was in charge of outsourcing, shipping, and data entry. By the time I'd run into J at the bar that night, I was pretty much integral to much of the logistical operations of the company. I have her to thank for it.

But that first 6 months I didn't do anything but work, go home, put on a pair of panties, a chemise and watch TV, clean my apartment, even garden on my patio. I had a completely fenced-in patio, so I was living out loud as a panty-loving sissyboi without any worries.

J had planted that seed long ago. She would dress me up, and paint my face, she had me giving her pedis, foot rubs, and cunnilingus as a matter of routine. When I was alone, I dressed like a sissyboi 24/7. It helped me keep the right mindset, a clean house, bathroom, kitchen, and a tidy little patio garden. I was a total domestic and in panties, it didn't seem like chores, it was fun.

I had all Vanity Fairs. I had a couple of sleeping gowns, a couple of chemises, and a couple of slips. I also had a collection of sheer-to-waist nylons. I also bought my first bottomless girdle. I began to shave my crotch and ass. I kept myself smooth wherever my shorts or swim trunks would cover. I didn't have many friends at this point. All my friends were attached in some form to J, so I was a loner, but not lonely.

It was the early days of the internet and in my free time, I spent most of it online. My favorite website was LLAPA, Lingerie Lovers and Panty Art. It was a jack-of-all-trades porn site for panty lovers. They had fiction, photos, toys, and lingerie for sale. I made a profile where I posted photos of myself in panties, always with my face cut out, and I wrote stories and published those too. It was one of the first social media platforms because people could comment, leave you a like or dislike, and you could see the number of views. That was very enticing because my stories always got a lot of views with some comments. Even my photos got hits.

I still bought the monthly edition of Leg Show magazine too. I had gotten a couple of my stories published in that as well. I started buying panties and lingerie online too by then, but I was still going to JC Penny and Target to get my VFs. Nothing beats a full-cut pair of VFs.

I hid my fetish. I still considered it a fetish. J had me wearing panties pretty much every day. She liked to scissor with me and that kind of thing just doesn't go away once the woman does. I bought my first vibrator from LLAPA's website. J had introduced me to vibes, plugs, and beads.

Like I said, I still considered it a fetish. I saw myself as a woman because I loved the female form. When I was all dressed up and looked at myself in the mirror, I saw a woman and I wanted to make love to myself. That's when I started to suck my cock. I could get the entire head into my mouth. It wasn't like getting oral from a woman though, I was hardly ever able to make myself orgasm with my mouth, although I always ejaculated onto my face, lips, and into my mouth when I masturbated like this. Only one time, and I don't know why or what was different about it, but one time I was able to go so far down on myself that I ejaculated because of the way my mouth felt on me and that was amazing.

Anyway, I'm getting off track here. My point was, I was a loner. On a Friday night, I would get home from work, take a shower, shave, dress up like a sissy pantyboi, then put on a nice outfit over my lingerie. I would walk to downtown Long Beach and hit up some bars and clubs. It was only about a 30-minute walk. I would fill my flask up with whisky and stash a joint in my pack of smokes and I would walk along the beach, or the busy Long Beach party streets and sip my whisky and smoke my weed.

I made up this game where I pretended to be a reporter, a writer, or a photographer, and tried to get into clubs. I liked messing with all the hip and cool people. I looked like them, but I acted totally crazy. I got a total kick out of making a scene and trying to get people to laugh or talk.

Sometimes it worked. I made up a press pass using the copy and laminating machines at work, bought a lanyard and a plastic carrying case, and went out with it trying to get into places. They were revitalizing the downtown area and a bunch of hip new clubs were opening up. I got a couple of them to let me in.

I know a lot of people can't stand going out alone, but I just pretended I had people waiting for me, or that I was with people. In a club, nobody knows who you're with. And sometimes, I'd just join in with a group of people and act like I belonged and end up partying with them all night.

Most of the time, I'd forget I was even wearing panties beneath my clothes. Once I started partying and people were around, I could focus my energy on just being with people like every other normal person. It wasn't until I left and started walking home, or when I would be sitting by myself out on some patio cafe that I would center my attention on my panties. If I was really drunk and high, I'd take off my pants and walk down the beach in just my panties. It would be dark and no one would be able to recognize me because I didn't know anyone. My job and everyone I knew was in OC, I lived in LA. I was just another freak in their minds.

I worked that dotcom gig for two years and was starting to get bored of the job. I didn't know what I wanted to be, but I knew it wasn't working at this place forever. I had a couple of good friends from Ohio who'd recently moved to Portland, Oregon so I took a week off work and went to visit them. I had a blast. I visited them three times over the two years I was working at the dot-com gig and started making plans to move up there. One of my friends had started going to community college and had a house where he was renting rooms and he inspired me to make the move. I was saving for a pickup truck at the time I was contemplating moving to Portland and I set a date for the following summer. It was early December when I set that goal. I told myself I'd save enough for a pickup, get registered for classes, and have a place to live all set up by July 4th. In Oregon, they didn't have out-of-state fees so I could register online from California. I did that in the first week of the new year and by March I had bought a pretty nice Ford Ranger with cash. The only thing I had to do was secure a place to live.

I was living up to my potential and doing it alone. I had become tight with JP and EH, guys from the file room. I was managing that, the year had just turned over to the new millennium and me, JP, and EH were running a finely tuned machine that I had built from the ground up. We were tight. OK, and we rollerbladed. We had a gang of bladers. EH's and JP's girls were in it too. I had this one girl MM who I'd drag along, but we were just stoner buddies. We went to clubs, we dropped LSD, and shrooms, X was brand new then, and drank beer, wine, and whisky.

And I'd committed to a total change. I was going to live the life of an academic and work at a coffee shop in Portland.

That's when I met M.