Letters

Letter #1

When I was in grad school I was single and contentedly so. The year I graduated with a BA in Literature, M and I broke up. We were engaged the summer between my junior and senior years to be married. I helped her move her things from Portland to Chicago that summer, she was starting Law School, I would finish at PSU and join her summer of my graduation. We did a tour of National Parks on the way and I proposed to her on the first night in her new flat, a last-ditch effort to demonstrate my love for her. I harbored suspicions regarding the whole long-distance thing, they'd never worked out in the past. By the time my final year was winding to a close, M decided she wasn't coming to my graduation. I'd already arranged for my parents, brothers, sisters, nieces, and aunt to come. Hotels, dinner reservations, the whole nine yards, and M just didn't come.

I learned later that she'd found someone, and I knew she would. Going through the first year of Law at an Ivy League program is like a crucible, survival depends on a metamorphosis happening and when M experienced hers, I wasn't around to share in it. Everything was out of context and I was devastated when she finally sent me an email explaining. I knew I'd never find another woman like her and I didn't want to try.

I powered through and got accepted to an Education program in Portland. I was rooming with a group of really good friends in this mansion in Close-in Southeast. We were all in our late 20s/early 30s, all of us hustlers and go-getters but free from the corporate grasp, we were typical Portlanders of the era.

I had the attic and my own shower/bathroom. Privacy was important because I'd amassed a nice cross-dressing collection of panties, hosiery, and chemises and when I masturbated I liked to dress up and play with my vibrator.

At this stage I was just a submissive cross-dresser. M and I had elevated my experiences, I'd sucked her strap-on and she'd awkwardly tried once to fuck me with it. But mostly we did a lot of panty play. She had a mean streak that was lovely and humiliating. She was very vocal and liked to degrade me and shame me. But I loved it. She had a way of knowing exactly how to humiliate me. A simple look in public could inspire fear in my heart. Once, we were in a lingerie boutique and she caught me eyeing the wide-net fishnets and she laughed out loud and asked me if those were the kind of hose I like to wear.

She could push me so far. But I did the same for her. We were sitting in my truck one Saturday morning at a waterfront park along the Columbia. Usually very busy, but it was early on a weekend and the crowd hadn't started to gather yet. We were having coffee and a snack and I dared her to take off her shorts. Then I dared her to take off her shirt, then to go over to the nearest garbage can and throw away our trash, and when she did I locked the door and took off. She seemed to love it.

During the year between undergrad and grad school I just worked. All the overtime I could get. I traveled around for work, leaving on a Monday and returning usually Thursday or Friday. This gave me plenty of opportunities to play, and to buy new outfits. That's the biggest fear of a crossdresser, getting caught buying panties and being "out of town" most days made it easy.

At that time, the panties and outfits were just role-playing with M, fantasies that I'd concoct. Every time I masturbated I had some specific memory associated with M. If I masturbated and I slapped my smoothly shaved balls with the tips of my fingers, increasing in firmness and frequency, I was remembering the many times M and J had done this to me while I stroked myself. If I was inserting my dildo in my shaven ass, it was because I was remembering when J or M used theirs on me. Fucking me and calling me humiliating things that seemed only to encourage me more.

By the time grad school started I had shifted my mindset. I stopped with the crossdressing, except for rare occasions. Back then I would masturbate and most times I would be done in 10 or 15 minutes. Even less when panties were involved. I had no problem focusing on academics and work, masturbation was something I did to realign myself, get back on track.

That's when I met MH. A Mormon single mom of six kids. She was a tiny thing, but kind, sincere, and sexy in a conservative way, maternal I'd say. It was my first year of the Ed program and like Law school it was a crucible. MH and I hit it off. I was just friendly with her, curious about Mormonism, curious about how she could have six kids, curious about the way she seemed to notice me. I had no romantic interest in her, but I did think she was attractive, I did like talking to her.

On a whim, after hanging out with her and her family for the day, I asked her on a date. I made her dinner at the mansion, we had a candle-lit dinner on a warm spring evening on the back veranda and it was so easy. I had not inhibitions with her because I knew I wasn't "courting" her in the sense that you might imagine. I knew about her devotion to her religion, she made it clear that she was not promiscuous. It was like going out with a really good friend who was a woman, and to whom I was strangely attracted.

We went to a movie and halfway through we were holding hands. We walked out of the theatre still holding hands. I walked her home and kissed her goodnight at her door. It was a loving kiss that I only intended to be brief and affectionate. It turned into passion and it went on much longer than I expected. She seemed to "love" me with her kisses and I reciprocated on every action.

And that's how it started. It wasn't even announced, we just kept hanging out as a family, we'd go on "dates", I'd drop her off and we would make out for 30, 45 minutes and even longer. I would leave every night with sore testicles. MH had no idea about my crossdressing. No idea that I kept my crotch and ass smoothly shaven. She only knew me as a man.

I never wore panties with her and her family. I was wearing them often under my clothes. I wore VF full-cut nylon pastel-colored panties under my clothes, panties had simply become my preferred undergarment of choice. I still had a bunch of microfibre, skin-tight boxers that were nearly like wearing panties, and I wore these when I was with MH and her kids.

Our makeout sessions were very intense. During this time, because of the way we kissed, I found "lesbian Japanese girls kissing" videos on YouTube. Our kissing was so intense that it struck me one night to search up "kissing" and "lesbian kissing" to kind of reinforce our makeout sessions. Kissing MH was a total body and mind experience. I always put myself into this kind of trance. I was trying to lure MH into a heated state of arousal. I was trying to get her so turned on that she would break her "code" of no sex.

I knew and understood her boundaries. She said only kissing, and touching was restricted to outside the clothing. We could touch each other's skin, but only if it was exposed, as in a short-sleeved shirt which allowed you permission to touch the elbow or upper arm or underarm.

She wore sandals in the spring and summer and I gave her foot massages. She seemed to enjoy them so very much. She seemed to enjoy everything we did during our makeout sessions very much, as much as I did. I tried with all of my resources available to me to coax her to break her own boundaries because I knew that was the only way her rules could be broken. If I pursued too hard, beyond her boundaries, I knew it would be forbidden, and even if she did submit for some ungodly reason, I knew that would be a violation of the rules of this game.

I saw it as a game. She did not. Although the way she kissed me and touched me, the way she responded to my maneuvers and reciprocated even the most lascivious of acts, I believed if I just kept it up she would break first. She would become so overwhelmed with need that she would be the one to reach into my pants first. This is also why I never wore panties with her. Could you imagine??? A Mormon, mother of six, in a fit of passion, reaches into my shorts and finds a pink pair of VF nylon panties?! Whoo lordy, that would be rich.

But, she never succumbed. And the makeout sessions just kept getting more and more intense. I sometimes had to politely decline to make out if I knew I had work to do or some other responsibility because after a night of making out with MH I would have to masturbate two or three times before going to bed because my balls were so inflated.

It was the fall of our second year, MH and I were dating officially, everyone in the cohort knew it. We were a very close group. I would party, smoke, and drink with our little group, go see shows, music, play games, and just hang out and smoke weed. They thought that I was dating MH in some ironic sense. Like someone who lived and believed as I do, could never date such a religious devotee as MH. We laughed and I understood their suspicions, but I assured them that it was real. MH never came out with us on our carousing, but she was part of our group and everyone seemed to just accept everyone. It was really beautiful.

I was staying out at this lake house doing some work for the guy that owned the mansion me and my friends were renting. MH came out to visit and I cooked her dinner. Fresh fish from the lake and mushrooms from the forest. We were making out in the driveway leaning up against her minivan. It was a warm autumn evening. She was wearing a summer skirt that came to her ankles, it was satin or silk and we began making out. I was spurred forward by the feel of her skirt and before I knew what I was doing I was lifting the hem of her skirt up and sliding my hand underneath. I felt a cloud of silky satin, it seemed like slips upon slips and panties that reached down past her knees.

I was like an animal and I pushed her against her van. I wanted to find out what she was wearing.

MH pushed me away, turned and got into her van. She started the engine drove away.

She wouldn't return my calls or texts. She waited five days and then contacted me only to explain her actions.

"I will not compromise my beliefs for anyone," she said. "I love you, and if you can understand and abide by my wishes then we can continue seeing one another."

I knew I had violated her trust. Her body could take it, that I'm certain of, she knew how to use every part of her to arouse me just by kissing and touching. But I had betrayed her trust in me.

We resumed dating, but it took a while for our makeout sessions to resume at their previous levels, but they did, and they even surpassed them. It was during this time that I started to wear my VFs under my clothes while with her and her family. I knew there was no way she would ever reach into my pants and find them because I knew she would never be the first to relent. I was safe.

This might be the start of my fascination with self-denial as a form of foreplay. I would come home after making out with MH and my panties would be soaked. I used to take them off in the truck and on the ride home I would suck out the sperm. I am not exaggerating when I say that my panties were wet with sperm after making out with MH.

I realized something about myself. I can embody a woman and still please a woman the way she desires. As long as I don't reveal what is actually going on inside my head, women will be aroused. MH must have perceived masculinity, or if not that, then whatever she was perceiving and receiving from me was effectively turning her on. Maybe it's not masculine or feminine, but finding out what the other person likes and doing that, regardless of the "label" mainstream society places on it.

If I was embodying a woman, and I was kissing a woman, then my worldview of our interactions is of two lesbians loving each other with their minds. If MH is a woman and I am a man and her worldview is that we are a heterosexual couple making out, her arousal and urgency indicate that she approves of my presentation.

I was presenting myself with MH in the same way I was presenting myself with J and M, except with J and M, the panties and submission was explicit and out in the open. I realized that being able to "expose" my true self to J and M as a crossdressing submissive was very powerful and a much preferable experience. But, I also realized that embodying a woman, or at least my understanding of a woman's sexuality, I was able to arouse a heterosexual woman, but only because she wasn't consciously aware of my feminine embodiment. I kept that part hidden. And in that act of self-suppression, I'd added a new facet to my sexuality, the need to be denied.

After graduation, I got a job in Florida. MH had gotten one in Sherwood, right in her neighborhood and we were spending as much time as we could before I had to leave. She didn't want me to go. I knew that if I stayed I'd marry her and that would have been awesome, but I'd never have the chance to have kids of my own, and I wanted that very much. I had to leave.

We went on this two-week long road trip vacation, hitting up state parks along the way to Chicago (I know it sounds familiar), where her mom and dad lived. We stayed with her parents a week and then I left for good.

One night, after the kids had gone to bed, we went for a soak in her parents' hot tub. I wore board shorts and she wore a one-piece. We started making out immediately. She was squirming around in my hands and arms and against my body like a cuddly lion. She was in my lap, her ass pressed directly on my hard cock. She ground herself against me and I breathed like a hungry whore into her mouth and shivered up and down several crests toward what would inevitably end with me ejaculating in my swim trunks.

Our makeout session was so intense. We were touching each other everywhere. I was using my forearms to feel her breasts and squeeze them. She was grinding her ass and pussy onto my rock-hard cock. My head was swimming in the steam and sexuality of it all. I only know that I could only take so much of her ministrations. I had persevered through a dozen "near-misses", approaching the point of no return several times before she found a way to take me over the edge. I shivered and humped into her holding onto her like a spent swimmer and when I finally calmed down MH looked me in the eyes, with a warm tender smile, and began kissing my face and neck gently with countless kisses, the kind a woman gives her man after he's orgasmed exceptionally well. She must have known. She had to have known.

Letter #2

I was 21 and living with my old manager at Big Boy's. His name was G and he was married to DC, a fellow food server at Big Boy's. DC had a little girl from a previous marriage, but they were a great little family. I lived in the basement. Not like a troll living under the house, I was quite fond of the little one and was often privileged to care for her, cook for her, and even read bedtime stories to. I enjoyed it because down deep all I ever really knew that I wanted was to be a father. But that's way off-topic. The point is, they viewed me as one of the family, and I enjoyed that. The basement was finished and it was down the hall from a utility room and the laundry room.

G was manager at Bob's until he got a high-level security gig downtown. He worked nights, but on his off nights we'd all sit around and smoke weed, have a few drinks, and play Nintendo or watch a movie. The little one would be sleeping of course.

One day G comes down and wants to talk. He and DC are having trouble figuring out their sexual dynamic and he says she wants to suck his cock and drink his cum. That she wants it on her face and tits.

Of course, my instinct is to shrug and inquire what the problem could possibly be. But, I take the "good friend" approach and let him get everything out in the open. He says it feels like he's degrading her. I understand that, but not if that's what she's in to. In this case you bite the bullet and go ahead and appease her. He wasn't convinced, so I told him he should just talk to her honestly. See what it is she likes and why she likes it.

DC and I both worked at Bob's still and the staff, front and back of the house, were one hell of a team. We were all between 18 and 28, there was a mennonite who worked with us who was 28. She liked making things out of money, like tabletops and picture frames. She didn't party with us, but cute and fun and laughed at everything. There were around a half-dozen of us, plus little satellite spin-offs that also orbited and converged with one another. It was good. Take a couple classes at community college during the day, work at night, party till 1:00 go to sleep, and still have the energy to study and be active.

There was just me and my buddy P as male representatives of the front house crew, the whole back house was male, K was a great guy and terrific cook. He aspired to become a chef. The whole rest of the front house were female and young and hot and fun. All of them. And we all had a blast because between me and my buddy P, we didn't really care if we got laid. It didn't matter. I had grown accustomed to being a reject and P was just in a different world. We related well and we liked to have fun so it was perfect.

That's a bit off the topic, I was saying all that to say this, me, G, DC, and little one made a great living situation for me. One of the best I've ever had. If I came home and the lights or TV was on in the living room I would go in, smoke a joint with them and chill. Because G worked nights, DC and me would just hang. She liked to smoke and talk and she could talk. She was pretty sexy, big and curvy, big lips, round face, dark brown eyes, and long black lashes. She'd be chilling in just a T-shirt and panties with me on the couch or on the floor playing cards. I could see her panties so easily. She had this nice round ass and her panties fitted spectacularly, I'd say they were bikini style. Always white, and shiny, like nylon or silk. It wasn't unusual though, or some overt hint toward me in any way, she dressed like this from the time she puts her daughter to bed, no matter who was in the house. I wasn't being targeted. I had no eyes for DC at the time. I believed in my loyalty to G and to the little one, I would never impact that dynamic. That didn't mean I didn't look like a mofo whenever we hung out at night. If G was there, I didn't even let myself try to steal a quick look, ever. But when it was just us, my god...and I think she encouraged me with some of the poses she'd sit in. I mean on the floor, one foot tucked in under the thigh of which is extended out and slightly spread so that as I'm leaned over on my elbow with my legs outstretched I'm granted a god's eye view of DC's panties.

Oh, and you might have the wrong impression of her. She was only like this with her family, if people were invited to come over and she knew about it, she represented herself just like the rest of us. I found it endearing. I rather enjoyed her confidence, she shared a lot of her history with me, even brought up the oral sex thing with G.

We often had "sexy" topics in our conversations, we're both Scorpiors. But when she started bringing up G I began to suspect that G had told her about our discussion.

Meanwhile, unbeknownst to all parties, I had been sneaking into the laundry room and stealing DC's panties. I won't bore you with the details of my frolicking but suffice it to say, I believe now, in hindsight, and probably wishful thinking, that DC was aware of my indiscresions, which resulted in her making a very difficult-to-refuse proposal months later. I've reasoned that what starts happening next is calculated and purposefully employed by DC.

I came home around 11:30 one night, I'd only stayed to smoke a joint in the parking lot after work with a couple of the girls. I walk in thinking I'd smoke a joint with DC because I could see the light of the TV flickering.