Letters Continuing

Letter #4

The week after I met M I paid cash for a sweet 96' Ford Ranger. I showed up at her work to surprise her. And I did. She was stunned. But she concocted, in her mind, some crazy story about me that made me a far more fascinating person than I actually am. But I did my level-best to live up to her image of me.

I'll tell you the story of our first date. It was in my local pub in between Long Beach proper and Belmont Shores, a block toward the ocean off Junipero. The neighborhood would later become hipster central, but this was before that. I knew everyone at the place, it was my hangout. I had the advantage.

She was 23, I was 29. She blew me away. I mean like Good Will Hunting blew me away. That night we drank Jack-and-Cokes and talked at the bar, and played pool, and then back at the bar. She was from another world and I was hungry for her. Yes, of course, we walked back to my place and we fucked. But the next day was Saturday and she took me to her place. It was just a few blocks away, she was rooming with a friend from university but she was away.

When she unlocked the door, I rushed her and picked her up. She was elfish in stature, I was lithe, strong, and twice her height. I pinned her against the wall and pulled her pants and panties off with one hand and lifted her onto my hard cock with the other. I turned her around and carried her towards the open door and used her body to slam it shut as I rammed up into her and then I proceeded to carry her around her flat and fucking her like a king.

She was like an elf. A wicked smile with eyes that matched, elfish brown, and tousled hair, and tiny tits with pink areola about the size of a silver dollar, little tiny and pink Mt. Fujis on her chest. She had the ass of a boy, but feet that have no equal. I used her body like a toy. I could fuck her in any position and she could fuck me back. To say it was electric trivializes what it was, there has never been anything like this for me. I wanted to marry her that morning after I finished fucking her in her bedroom. I wish I would have asked her.

We stayed at her place that night and I couldn't keep my hands off of her. She was so different from J. J was a woman; full and curvy, feminine and dignified. M was a wild animal. She had braces, literally, she looked more like a 18-year-old boy than a 23-year-old woman. She was doing porn. Literally (I know I'm saying literally a lot). She was going on a boat with some old man and doing porn. She told me because she had braces, it made her look young and that was her niche. It was her rule that she be allowed to pursue this endeavor. Of course, I saw this as a way to reveal my fetish to her. I admitted everything about myself and my fetish in hopes that she would one, accept it, and two, even find it intriguing enough to pursue. I reasoned that because she was admitting her "deviant" side to me, I could risk telling her about mine. If I was doing porn I don't think I could ever admit that, but she did. So I thought, why should I be ashamed? And I hoped she would accept me. And she did. She not only accepted me, but she enjoyed it as well. She was so fucking cool. An educated woman will see value in a creative approach to sex. And I think M recognized how much better a lover I was as a sissyboi than I was as a "man". She was pansexual, she'd had so many wild experiences and I wanted to show her I was no prude.

She did her porn, I never objected, besides, how could I? I'd be a hypocrite. We dated and she told me everything she'd done sexually. Orgies, bi, homosexual, even shemales she'd been with.

Also, finally, I had a partner to bring to our rollerblading crew. M could skate pretty good. And, like I said before a week later I show up at her work in my brand new Ford Ranger and she fucking flips out. I think this had a tremendous impact on her. It gave her the wrong impression. I had done all this without a woman. She was an inadvertent benefactor of something she had nothing to do with, she made it all about her. I didn't see that though, not at the time. If I had, I don't know that I would have been intelligent enough to do anything about it. But knowing what I know now, I would have been more clear, explained to her everything that I'd gone through and that I was happy now with the person I had become and didn't want to lose that. Instead, I used her misconceptions to convince her to move to Portland with me.

It wasn't exactly like that. She had options. One of them was doing service work in Portland, but she had many other options available to her. She was an Ivy League graduate. Plus, we got on so well that she went for it, it was her choice. But it was under false premises. I was focusing on school. That's all I cared about.

It was during this time of transition and preparation for my move to Portland that my sister's husband offered me a way to own a business. It was furniture and carpet cleaning gig. All I had to do was travel back to Ohio and pick up the machines, do some training and then try my luck in Portland.

The first thing I did when I got to Portland was go to every rent-to-own furniture store and introduce myself. I gave the store managers my card and offered the first set of furniture cleaning for free. Before the month was out, I had a handful of stores I was visiting once a week. By the time I started classes in the fall I was earning enough money between cleaning, food stamps, social assistance from the state, and scholarships that I was able to live a pretty easy and academic life. I made school and growing my business my life. My buddies from Ohio, JJ and GG were living nearby, GG was going to the same school I was, and JJ and his small family, his wife and newborn boy, had a small house with a yard up on Mount Tabor and I spent my free time hanging out with them. M and JJ's wife R got along great. R introduced us to S, her bestie with whom she had shared ownership of a small little flowershop in SE. M was making friends of her own working at Habitat for Humanity. They were all her age, recent college grads, privileged and from money. I didn't get along with most of them, but M, R, and S got along pretty well and they would hang out a lot, go to clubs together, hang out independently of me, JJ, and GG.

M found a porn producer through her LA connections and she resumed that. She would bring home toys and sexy outfits from her shoots. She never let me see what she was doing, but she would tell me in vivid detail about her adventures. She was rooming with a couple of the Habitat crew and I had a little studio in SE so our lives were our own, but I loved her and we were ok. I wanted to see her shoots. I wanted to know everything she was doing, not to track her, but because it turned me on to imagine her. She never let me see any of it though. She showed all of her friends and that was a subtle form of humiliation that turned me on. She also told her friends about our sex life. I was pretty much wearing panties 24/7 now. I had reasoned that if she was going to pursue her kinks, then I would too.

She didn't seem to mind, at times she even seemed to enjoy it. She began buying me panties and I just thought this was the most endearing gift a woman had ever given me.

The way she touched me made me feel like a woman. She didn't "jack me off" she "rubbed" and "fingered" me through my panties. She used the tips of her fingers, rubbing the underside of the tip of my cock through my silky panties, and speaking out-loud to me. She was the first one to call my cock a clit. She would press two fingers deep into my perineum through my panties and she called that "fingering me." She liked that I kept myself clean and smooth, she even expressed envy when I became so adept at shaving my asshole, balls, and pubis that she once wondered aloud how I was able to keep myself smoother than she could even do.

Knowing she was telling her friends about our sex life was a humilating turn on for me. She was very vocal during our sex. She would tell me about her porn shoots, or she would tell me what she had told her friends about me. I would imagine her explaining the sordid details: "Then I "finger" his pussy through his panties and he spreads his legs just like a whore and he moans like a woman. It's so funny, I have to keep from laughing, and sometimes I laugh out loud as he fucks his hips to meet my thrusting fingers."

I really believe she shared in my fetish for panties because she would lick and smell her own panties after I'd played with her pussy through them and gotten her wet and turned on. She would lick them, rub them on her face and lips and then kiss me. She liked kissing me after I'd been giving her oral. She would finger her pussy and get her sperm all over them and then she would rub my perineum with her wet fingers and tell me that a good sissy should smell like pussy too.

I wrote stories for her and she loved them. I used my stories to provide her with ideas and to reveal what thoughts ran through my mind when we were together. We would go about once a month to some cabin, hotel, or lodge for a weekend and fuck and play. Whenever we walked into a new room or suite or cabin, we played our games.

She was the first woman I ever gave oral to her asshole. She kept herself totally hairless and she loved when I performed cunnilingus and analingus. She would get on the bed on all fours, spread her knees wide, like the splits wide, press her face into the pillows and her chest flat on the bed and open herself up to me, like an offering. I used my tongue on her like a cat, swiping and curling, finding every place that would elicit a response from her. I learned from J how to listen to a woman.

Slowly she began to admit that she needed more than a sissyboi. She liked to be taken, fucked hard, and manhandled. I would think of that first morning at her place in Long Beach where I fucked her like a king and I wanted that again, but I was too selfish. I wanted to be a sissyboi in panties, to service her like a proper sissy. I was a fool of course, stubborn and foolish. I had the capacity, but it was too intriguing to pursue my sissy desires.

It was during this time I found a porn shop that was near the waterfront in SE. It had booths, closets really. A line of 5 or 6 of them in the back of the store. You got in, closed the door, and there was a stool and a television screen that played porn when you put a dollar into the slot. That's where I discovered tranny and shemale porn. I had seen it before, but this was a whole collection of totally varied and wild shemale porn. The little rooms were lined up and the walls on the right and left had two-way, frosted glass windows. You could unfrost your side of the window and let the people in the adjacent rooms see you, or they could do the same and you could watch each other. I found this place and started going about once a month, whenever M would do a photo shoot.

At first I just wore my panties under my clothes, but it didn't take too many times going that I was dressing up fully in my panty girdle, chemise, thigh-highs, and panties and as soon as I locked the door I would undress and unfrost my side of the windows letting anyone see who wanted. I would ejaculate immediately knowing that I was being watched. Eventually, I learned to curb my enthusiasm and tease the boys, mostly old men, in the other booths.

But I always ejaculated and left before anyone could see me or catch me.

One night, M and me were out drinking and I admitted to her what I was doing. I thought she would like it, afterall she was doing porn. But she was furious. She was speaking very loud, loud enough that the whole bar heard her ask me if I liked trannies, was I a fag now, and do you suck cock now too?

It was humiliating and yet I was aroused. She noticed my shorts had a tent in them and she laughed at me when she asked in outrage if this was actually turning me on.

She never really got passed that. I thought she was a "free" spirit, but as it turns out, she was only free for her, not for me. After that, we had a "break". We came back together but the terms were different. She stopped the porn and I stopped wearning panties with her. I was ok with it, because I so dearly loved to service her. She still forced me to eat her pussy and asshole. She still fingered me and played with my clit. She even used a strap-on on me.

It was my last year of undergrad when she got accepted to law school in Chicago and the summer before my senior year we road-tripped from Portand to Chicago hitting as many national parks as possible.

She would leave me before my final year was finished. She found a new lover at law school, which I knew she would. But it still hurt, and it hurt dearly. I remember telling her once that I didn't think I would ever find another lover like her and if she left me I would remain single forever. That's actually not far off the truth. I have been in relationships since her, but none have ever compared. I was lucky enough to find a woman to marry me and give me children, but she was not even in the same atmosphere as M. In fact, when MS found out about my panty fetish, she was disgusted by me and it ended up being the final nail in our proverbial marriage coffin.

That's another story though. I will say this about MS, there is not one experience with her that I've ever had that remains in my "spank-bank." She was as milk-toast as I'd ever experienced, and not for lack of trying. This brings me back to my point about educated people and sex. MS was not educated. She was intelligent, smart, even clever, but she was not creative. I remain steadfast in my assertion that educated women make better lovers. M, J, DG, MH, and A were all educated and gave me pleasure that have been permanently seared into my psychology.