A Cross-Dresser’s tale

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A Cross-Dresser’s taleYou may think of me as Fiona, and I am a cross-dresser.A story by Erica inspired me to pen my saga of cross-dressing. I am also a recovering alcoholic, with a few days over 19 years without a drink as I write this, and I suppose the two tales are intertwined to some extent. Not that I am a saint by any means, a lot of people with a lot less time have a better sobriety than I. But I learned that alcohol is a poison to me, so I avoid it. I just do irrational things when I add alcohol to my system.For a while, I blamed my cross-dressing on the booze. But I discovered that feeling the need to slip into Fiona, into my “other mind” wasn’t booze related.But I’m getting ahead of myself.I love being Fiona and now realize that she is a real part of me — part of my mind, body and soul.I dress in my girl clothes almost daily, usually early in the morning prior to work. I wear panties or a thong beneath my hated boy-togs during the day when I can. I just feel better when I wear them.So now, here I sit in my fave sheer mini-skirt, thong and silk chemise putting down my memories and adventures as a cross-dresser. My nipples are erect, jutting through the silk and my clitty is leaking as I write this…If you are looking for a quick, hot, throbbing porn story for self-stimulation, then this tale will bore you. I apologize for that.But if you are in front of the keyboard staring at the screen in sexy lingerie, dreaming of cock and wondering how you got here….read on. Early memories — Pre-puberty through high school.Born to a Scots-Irish family, I am the eldest of four siblings, three boys and a girl in that order. We have a tight-knit Scottish clan on my maternal side and loose knit clan on the paternal side.I have three female cousins born within three months of me, so I was always surrounded by girls.Two cousins (maternal) we used to see quite a lot, and it was common for the three of us to have overnighters. I can remember being jealous of their sheer, frilly nightgowns while I wore those strangling pajamas. We stopped sleeping together as they hit puberty.I also remember being jealous of their soft, firm titties as they started to grow. I wanted breasts, but began to repress the thoughts as I drifted into puberty. But I distinctly recall the terror of my first locker room, of undressing in front of the other hopeful eighth grade football players in the old junior high school.It took me a long time to get “comfortable” in the locker room, and looking back, wonder if that was one of the reasons I tried to be the first person in and the last to leave.Somehow, it didn’t seem right, although I couldn’t put my finger on it or talk to anyone about it. It was the early 1970’s and “gay” still meant being happy, not an alternative lifestyle. I’m pretty sure that I didn’t REALLY know what a homosexual was, though I’m sure that I, like my peers, often called other people fags.I didn’t start masturbating until I was about 14 — when a friend told me about it. I soon discovered that using pillows to pleasure myself was far superior to just “rubbing one out” and about that time, I began buying men’s magazines.I was home alone one day, being sick (of) from school, when I found one of my mother’s discarded slips in the trash as I was doing my chores.It felt so smooth and soft to my fingers…I slipped it on and marveled at how my nipples came erect and I LOVED the sensation of the silky fabric over my ass and little cock. I began to plan how to be alone to wear my new slip and pleasure myself in it. I do remember trying on panty hose and a bra once, but the slip was my first “gurl-thing.” I vaguely remember (probably due to the massive quantities of alcohol to be consumed later…or suppressed.) trying lipstick on one morning, and trying to get into her heels. I sort of recall walking and strutting in front of the mirror, running my hands over my body like a man would….This continued for about two years, until I had a flash of self-disgust/guilt/religion when I disposed of it, the first of my many purges.Things were pretty vanilla for a couple of years after that first purge. Football, wrestling, girls, school and working part-time jobs in the winter and working on the family farms in the summer filled that slot.I can vividly remember the depressive bouts I had, not seeming to fit in, not ever seeming to maintain a relationship with a girl for long. I have fought these waves of depression all my life.I had my first drink on my 15th birthday and soon after that, cousins and uncles were handing me beers as I was “becoming a man.” It was about this time…timelines get fuzzy because of the booze…that I saw my first she-male in an edition of Club Magazine. I was mesmerized. She was so hot and I wanted her, to be like her. I kept that mag for a long, long time. I can remember ALWAYS checking Club for more she-male pics, although I was rarely rewarded.The images are burned on my mind, I can still see her now.I had my first experience with intercourse the November of that year and the relationship turned out bad. Really bad. I didn’t date for a year. Then I fell in love with my high school sweetheart.We never had sex, though we came close once or twice in our solid 2 year, and then once in our tortuous third year.We did get very good at oral sex though.College hazeI was dating sweetheart when I graduated from high school and went into college at the local juco. I kept dating her throughout that winter. She broke up with me the night of her prom. I packed my car and headed for a cattle ranch in the West, halkalı escort owned by a relative, to work and heal.I don’t remember cross-dressing at this time, but I was drinking. I do remember looking over some lingerie in a few shops…Through this all, I kept masturbating with pillows, often spreading my legs, wondering what it would be like to have a man inside them, pushing his rock hard cock into my pussy. I knew I wasn’t gay per se…I never did imagine havng sex AS a man with a man. I still don’t.But I also knew that I had desires to be satisfied sexually as a woman. I often fantasized that I was a girl, my wet, heavy breasts bobbing in rhythm to the stud’s pounding of my loins, making me cum over and over again. However, I am pretty sure I wasn’t dressing. I remember thinking about it a few time though, when I was really drunk, usually on Tequila Sunrises. Come to think of it, I’ve always had a weakness for “girl” drinks too.Sweetheart and I began writing, she sending the first letter and before I knew it, I was going back to school at the university she attended. We got into a fight almost immediately.I began drinking heavily, I had roommates and lots of one-night stands after my HS sweetheart and I broke up. I was morose and began to skip class and go to the library to read about transgendered people. I read everything I could find on the subject and ordered every book I could from the collegiate inter-loan library. I began to wonder just what was wrong with me? Even then, I caught myself with serious cases of breast envy.I saw ther****ts for depression a couple of times, but never mentioned my cross-dressing or yearning. I know a purged a lot of kits….sometimes twice a month. I cheerfully drank my way out of that school and had to return to my parents’ house.I quit drinking (for a little bit) got a job. My HS sweetheart came home for the summer, and although we didn’t date, we were talking again, just being civil. I don’t think there was anything to it. Then she died in a car wreck. The drinking began once again and one night, during that six-month binge, I began cross-dressing again.That is about the time when I learned to shop for “holidays”–Halloween, Xmas, Valentines… “girlfriends’” birthdays. I used to drive hundreds of miles to porn shops in other towns to buy lingerie. I remember a red satin bustier with garters and hose and I was hooked. I hid my “kit” as I called it and lived for the moments alone with my girl. As my parents and sister were away a lot of weekends visiting relatives or my brothers still in college, I found some quality gurl time.I think it was then that I began to play with my clitty, getting it folded behind my ass as I humped two pillows…my thighs squeezing it to ecstasy. This let me keep my hands free so I could play with my nipples while I dreamed of being fucked.I returned to school while working full time, (paying rent to my folks) finished juco, graduated and went to another university in the state. I began to smoke there too.That university experience was an alcohol-fueled two winters, in which I once again built a lot of kits only to purge them. I had a lot of fun. I recall being really drunk and tempted one night by a handsome young man, but he wanted me as a man and that “turned me off.” We had a LOT of pillows at one of my apartments during this time and I did the laundry. (sometimes dressed as a maid I fuzzily recall). So I kept experimenting with them until I could tuck my clitty and her labias (ballies) behind my spread legs, as I lowered all my bodyweight down on the focal point at the base of the shaft — sliding my hips forward and leaning on the pillows in front of me to support my upper frame. I discovered that I could get the head of the clitty to lie over my virgin pussy. I came a lot after that discovery and found I could tease my nipples at the simultaneously as I came. I came A LOT.However, I was drunk and depressed. Soon, I was kicked out of school again, evicted…and I remember waiting for the dawn by the river. I was a sick failure of a man. I heard a train heading west and thought about just following my gurl, outing her in San Francisco. Disappearing forever.The splash of my last and final kit (so I thought) brought me back. I quit drinking again, for four months.Started drinking again on Fourth of July when told I could have just one. Had four. I was dying of alcohol just seven years later.I was dating a nice girl, loved her but she saw through my drinking and that pretty much ended it on my return to my c***dhood town. Returned to my former job and had a new kit put together in one night by October of that year. Now that I knew how to get my clitty back there, I was trying to figure out how to get it in the hole. I worked and worked at it unsuccessfully. I Mmet my wife, fell in love (still am. Got damn lucky.) and you guessed it, no need for kit. Yet another purge.Marriage drunken YearsNo real need to go into a lot of detail, but after drinking my way out of a good job, I successfully drank my way out of another. Depressed, I somehow brought back my kits. Seem to remember looking for bargains…real hazy. I do remember that is about the period when I began to collect breast forms, after experimenting with water balloons in my bras and outfits. There were selling silicone ones on tv and soon I found them in department stores. I would buy a set in one town of course, find an excuse to go to the big city and hit several stores to get a collection.I taksim escort glued them together with silicone to make boobs, checking my silhouette, until I had a shapely female form. I finally finished two sets, one a smaller set of boobs and a larger set. I still have them. I like the smaller set better.Quite drunken one night, with the wife and k**s away for the weekend, I shaved all over for the first time. Also fell asleep in lingerie for the first time and LOVED it. Pretty sure veggie sex was involved or a candle.Shame and guilt overrode my mind, along with a ginormous hangover the next morning. But I remember keeping and using that red outfit (complete with garter-straps and thigh high stockings) and getting a black one like it and wearing them for years.I wore my “boobs” whenever I could with my outfits. I tried to do homemaking chores with the boobs in their cups. I continued to stimulate my nipples when I came. Towards the very end of my drinking career I was so drunk one night that I decided to try sex with a man “as-a-man.” He was a nice guy, a professional engineer. He wanted me to swallow his nuts and bite as he came. Like a slut, I did what he wanted, swallowing his nuts and biting as he came. Meanwhile, I was pretending I was in my favorite teddy. I wanted to be had like a gurl, with my legs wrapped around him as he plunged into me. It was a dismal failure. The pain and remorse after this encounter were almost too much for me. Once again I though about switching genders and “disappearing,” but with two beautiful daughters on the ground, I couldn’t abandon them.When the wife had enough of my drinking and began procedures to file for a divorce, I had to choose between my love of alcohol and my family. Of course, the kit was the first thing to go when I quit drinking. Well, the second thing. The booze went first and I have been blessed for the help I received in arresting my addiction.Married with c***drenI got real lucky and saved my family, or rather, they saved me. And for years, I had thought that my gurl was a direct outcome of the booze. One of the things I could do without.But it happened one fall night, about four years into my sobriety when all were away for the weekend. BAM. I had a kit in less than two hours. It was due to my new job and I knew it. I hated the job. I loved the silk of the bodice as it stretched across my skin, covering my raw nipples and cascading in a little arc down my ass.The garters held the sheer thigh highs up in place and every movement, every gesture reminded me that I was dressed for HIM, a slutty little cock depository, a cum-dumpster. The gurl made me happy.As winter approached, I had concocted several outfits and a regular pattern of gurl time, as I worked the graveyard shifts. I made a kit that I could taking outdoors with me, either fishing, hunting, whatever and put on in the field beneath my heavy winter clothes.It was wonderful and I began to look for outdoor adventures, fucking myself in the woods and creeks. I bought what looked like a nice, life-sized dildo and began to experiment with it. Much better than veggie sex. But I never could get the pumping action going…so of course I tried incorporating the pillows into the action.We have always had a ton of pillows. One day, after stacking the pillows and pushing my clitty and labias behind me, I felt the top of my clitty rub my virgin pussy. I reached back and guided the head of my clitty into my slutty, aching hole. I played with my nipples as I pounded it into me, although it really doesn’t get in too far. Just the head in the outer opening, but inside enough that I could feel the sperm shoot into my body and then dribble down my thigh, calf and foot.It was ecstasy. I think I came three times that day. It was about then that I traded the job I hated for one that I despised. I hurt my knee, and then my back.I knew I would have to do something while laying up recuperating, so I turned my attention towards understanding computers and the web. The InternetWe had slow, slow dial-up and a little crappy computer set up in the one of the daughter’s rooms so they could do their homework. Our ‘new’ computer sat in the living room unconnected. That daughter graduated and I turned her room into a “recovery room.” I learned to stream music, understand a bit about windows and begin to surf the web. It was like a giant library and I soon was looking for transexual information.I soon learned that I was not alone. I remember getting dressed and going into transgendered chat rooms, swacked on pain pills. I began to dress daily. My kit had turned into a wardrobe and I had finally found some size 12 strappy 4” spikes. (Payless IS a gurl’s best friend.) I learned a lot about being transgendered and discovered information about the XXY gene. I am pretty sure that this could be a genetic thing, this crossing of the brain and sexual desires that some of us have. My father lost his long-standing professional job because of a “gay” action while drunk. My uncle (his brother) was gay too.But like I’ve said….men as a man doesn’t even interest me.Get me in a skirt and hose and I want that cock! I took my first pics dressed and uploaded them at this time. They were pretty bad. I pulled them all down when I left the site.I tried another site, a MU, or better known as an animated chat. The advertisement was “Be what you WANT to be!” I was soooo there. In fact, I still am. I love it.I came to the conclusion that I am what I am. Releasing Fiona into my brain “settled” a şişli escort huge void within me. Now she is struggling to get out through my body I think.I found Xhamster while looking for lactation videos. I’ve always wanted full, flowing nipples of milk for my man to suck out of me as he is pounding my pussy and was surfing the net before work.Here was the “social” network I was looking for. I have met a lot of nice kind people on Xhamster and of course, my share of perverts.I suppose that I’m one, so I fit right in!NOWI’ve come to accept the fact that I don’t have a nice thin, cute little body that would readily transition to the female form, Fiona, in my mind. I think that if we had the technology for transition that we have now, back in the late 80’s, I just might have gone through with it.As I began here on Xhamster, I thought that a readily source of she-male and cross-dressing porn would perhaps alleviate some of my cravings and desires. But as I began to watch the videos, usually dressed, my desire to lactate grew greater and greater so I continued my web searches and found a forum for males lactating.I followed some of their suggestions and discarded others, like unregulated hormonesI currently can extract a little milk each day from my stimulated nipples. I like to do that as I masturbate, with my little clitty-head barely sunk into my otherwise virgin pussy, dreaming of one man thrusting inside of me while another sucks me dry.My boobs now are a lot softer and I have lost a great deal of “strength” in my upper body. I love the way they now bounce, even without my silicone forms, when I strap on my heels and walk around in my miniskirts and garters.I began to experiment with photographs again and am somewhat pleased so far with the results. I’m on a campaign to lose weight, in order to expand my photo-shooting capabilities, and get into some sexier clothes.I usually wear a thong or panties to work beneath my hated boy-clothes. I only wear bikini-style “boy panties” when I have to wear boy underwear.I’ve been shaving my bikini-line, my boobs and the top half of my thighs for taking pics. Not just because I love the feel of my own smooth, soft, hairless skin. But to feel the soft fabric of the hose and the feel of the satin laces holding the garter-clips moving across my sheer thighs. Every step reminds me of what a slut I am.I’ve also begun to shave my boobs daily, liking the smooth feel as I milk or stimulate them for lactation.I find myself still in the closet, although pretty sure that my family knows about my dressing, we don’t discuss it. I love my wife and can’t even think about cheating on her with another woman. But as Fiona, as a gurl — the slut in me wants to get a hotel room and service cocks all night … I live near an interstate so I’ve often pondered meeting a trucker in his cab. Or a bunch of truckers. As Fiona, would I be cheating? Or would I just be “true” to another being within my psyche?This is the big question that keeps me locked in the closet. My wantonness wants to have a nice, thick throbbing pike of manhood in my pussy, to feel it pound me until I cum (hands free if possible) and feel him shoot his seed deep into me, and then have me suck it dry. Or make it hard again for another round. I would love to experience being fucked like a gurl, just once.I do get to travel in my job, so the opportunity is there. But I hate the shame and guilt of cheating. I vividly remember that time with the engineer and the guilt was terrible. I think a big part of me is afraid that if I let Fiona run amok, I would love it so much that I couldn’t stop, that my inner-slut would rise to the fore and literally fuck-up my marriage. I do believe that a lot of us cross-dressers/she-males/Trannys have the XXY syndrome, as I unprofessionally call it, as I’ve stated above. A lot of ancient societies, like the Plains tribes of North America, had sacred positions for transgendered people. I can’t prove that being transgendered is genetic, but I have a strong hunch that it is.I’ve found that I LOVE wearing thongs, have found some that can cradle my lil clitty and labias…keeping them high and encased in sexy silk all day. I’ve recently read that men prefer string-bikinis though. I have some of course, three pair of silky, satin, black ones. So it looks like I must not have purged them for a reason????I don’t purge anymore. I sort. The old stuff gets worked into nice soft rags.I love to gurl shop. When the teens were here, it was rather easy. Just collect everything they threw away that I liked. Since I travel, I can shop at odd hours, in different towns. I love the self-serve machines.I also like to shop in large urban areas, especially the thrift shops.I paint both my toes and finger nails. The fingernails I paint sheer, with a couple coats of hardener during the week. On the weekends I paint them shades of light pink. When I strip them for the work week, a wee bit of the pink colors them to a natural shade.The toenails are like a chromed-pink with a coat of pink glitter and a hardener. I keep them like that all the time except summer.I broke down and bought a bright pink wig the other day. And a new bikini swim suit. And NO no pics in the swim suit … I cannot afford to replace lenses on cameras.I am not good with makeup yet. I do practice a bit with hunting makeup, but that is all.I love to walk around in the dark, or early morning hours beneath full moon dressed and in my heels. I always wear my heels when I am doing a photoshoot.I’d love to try and ‘pass’ some night. Go to a club in the big city and get picked up…you know, the things we slatterns crave.Looking back on the last chapter of this saga, I have to ask myself…am I denying Fiona her legacy?? Or am I just sliding towards the inevitable night when a huge, thick cock spreads my virgin boi-pussy and finally fills me like the little cum-slut I am?

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