The Crossdresser's Fantasy Life

Hello. My name is Scott. I grew up in the mountains along the Blue Ridge Parkway, near Asheville, North Carolina. It has taken me years to admit it, but deep down I will tell you my big secret--I am a crossdresser, who loves the danger and thrill of it. I also enjoy living a nudist lifestyle when I can get away and hike nude in the mountains or go to my favorite nudist resort. One of the things on my fantasy bucket list is to place an order nude at a fast food drive through. Not as a man, but as a crossdresser the staff would believe was a woman. Women have done this before, a man could get in big trouble. Guess I'll have to try some other wild things first to work my courage up for this bold a fantasy.

Saying all this is liberating for me--because it has taken me years to reveal the real truth, even to myself. In a nutshell, it seems to me that I am straight, but bi-curious. I am a male who enjoys crossdressing as a wild woman. Shemales and trannies seem hot as hell to me. In fact, another fantasy is to be discovered as a crossdresser, then punished for it.

Until I was about 40, I played it straight. I dated women, and slept with four of them, but my heart was not in it. Sure, my dick was in some pussy now and then. I enjoyed sex, and loved getting a blow job as much as any man, but something was missing. I liked women, I just didn't want them full-time like some men did. I did not have to have them, in other words.

One woman I dated noticed something about me, and said, "I know you love me, Scott. Problem is you are not in love with me." That baffled me at the time, I could not see a distinction. But there was one, and it was profound.

I simply could not fool a romantic person like Leslie, my girl friend since the 90s. We were just fuck buddies, really. She saw that something was slightly off about my sexual desire. Another girl friend later noticed something else. She always denied me sex. Saving herself for her special wedding night, I guess. I took her sexual rejection in stride, never got upset when she teased, but did not deliver the goods. It was just her way.

She saw that I was disappointed, but she could not understand why I did not suffer a case of blue balls, as her previous boyfriends always had. Guess she'd been a cock-tease for a long time. She greatly enjoyed turning men on, but not giving them any sexual release. But I could not tell her the truth about not getting blue balls. Fact is---she was cruel to men, I did not care much for her. If we fucked--fine. If not, I was okay with that, too.

It wasn't that I did not love or admire women. I loved the way they dressed, how their make-up could hide their flaws. I was fascinated by how they used sex and their bodies to seduce men and sometimes lesbians. The lesbians I knew seemed like a happy, fun-loving group of people. Women having sex with women seemed natural to me. Men with men was interesting. I had not tried it since I was 15.

I liked how women could dress so provocatively, and get away with it. Men could not come close to using their bodies to tease like that. It simply would not work. A man would be called a pervert.

Hell, a woman could go out in a dress without her panties or a bra and it would be seen by many as sexy. She could flash her tits, pussy and ass to truckers on the interstate and get away with it. The 18-wheelers would blow their airhorns to show their approval of the car-driving flashers. But flashing your dick out on the highway could get a man in big trouble. You could be arrested, and branded as a sex criminal.

Men are limited in what they can wear and what they can do just to get laid. In brief, women have a lot of seduction advantages that men do not have. Their clothes are designed to attract men. On the other hand, men's clothes are kind of plain.

I didn't just admire sexy women, I wanted to be one, at least in a few fantasy adventures. That is when my crossdressing fetish started.

Back in 2015 I was in Florida on a spring training baseball trip. I saw several major league Braves games at Disney, near Orlando and then saw the Tigers play in Lakeland. It was fun to watch some games and get a good sun tan in the process. I wore women's shorts to the games. They were cut shorter than men's shorts, and you could cross your legs and show a little ass.

After a game I did something I've never done. I went into one of those cheap clothing stores you find all over Florida that sell all kinds of stuff from swim suits to message-bearing T-shirts. I bought myself a blue bikini. I had always wanted one to see how nude a person wearing one would feel. I figured it would be erotic as hell. It was. The bikini bottom was so small it was hard to keep my balls in and keep my pubic hair from showing. I shaved down there.

I then wore the bikini under my short shorts. What a great fit. It felt tight and sexy. I loved the bikini on me. I ditched all my underwear and wore the bikini all the time. I had to wash it often in the sink, but it dried quickly. Just to make my next adventure more fun, I also closely shaved my arms, legs, chest, stomach, back and butt. If I could reach it, I shaved it. I was finally a smoothie like many nudists I knew. I got a tight but revealing tank top, plus some sexy black flip-flops made for women. Putting it all together, I was about as stripped down as I could get for a man going into a public place. It was intoxicating just to walk into a business wearing so little. I felt naughty and exposed, but loved the new me. Brave, stripped down

and now a fearless-sort of person.

I went into a restaurant for some breakfast. My shorts rode way up my shaved thighs when I sat down in the booth. I felt sexy as hell. I let my flip-flops come off under the table. Kind of pushed them out of sight. I put my bare feet on the cold diner floor. Felt good. Two females working in the diner rushed over to take my order. They were middle-aged and clearly turned on by my bare feet, my bare arms, my smooth upper chest and my shaved legs. They warned me about being barefoot in there, but they loved how much skin I was showing. It was wild. Instead of being teased by women, I was now teasing them. I felt so sexy, so free, so female. The waitress reaction gave me a taste of the power of skin. I thought what it would feel like to be a crossdressing woman stripped down even more.

Dressed as a woman I could show more cleavage, and maybe show a part of my sexy ass.

Dressed as a woman I could wear only the bare essentials into the diner. Horny men would stare at me and might have fantasies about me. It was hot just to think about how I was dressed, and how much sexier I could make my public visits to stores, and some restaurants, "as a woman." But I knew it would take a lot of nerve just to attempt all this stuff. I would have to buy so many things--make-up, blush, skin cream, and much more. I'd even get my nails done and painted for my crossdressing adventures.

I got so turned in the diner that I took off my tank top and shorts when I got back into my car. It was getting hot and humid. I applied sun-tan lotion all over my newly shaved body. I drove on I-95 in Florida with my windows down only wearing my tiny bikini bottoms. None of the other drivers seemed to notice or care. It was live and let-live in Florida that extra warm March morning. I even saw some singles and couples driving naked that day. Nobody cared what you wore. Soon enough I raised my ass off the car seat and stripped off my bikini. I threw my bottoms into the passenger side floor board. I joined the other nude I-95 drivers.

What a rush, driving naked in broad daylight on a major U.S. north/south interstate. I drove nude for hours, and only got dressed to go to the rest area or to eat supper. It was erotic. I had to figure out a way to stay nude longer without interruption.

Driving naked was the most turned on I'd been since getting a one hour nude massage from a sexy woman at a Georgia nudist resort back in 2012.

A few days later I was back home in North Carolina after my fun adventures in Florida. I was now a changed-person. I started doing some wild stuff on the Blue Ridge Parkway, which runs from my home area around Asheville, north into Virginia. You can stay on the parkway for hours heading north, it had great possibilities for driving nude, walking in the woods naked, plus it would be ideal for some crossdressing fun up there.

Since the Parkway is a two-lane road for the most part along the crest of mountain ridges, I found it to be the perfect place for me-- my playground.

I bought a brown wig on line, plus some strappy heels and a sexy sundress and drove on the Parkway to see if anyone would notice "the pretty white lady with brown hair driving around flashing her tits." I loved wearing the sundress with nothing under it, as many brave women wear these days. Guess that's why they like them so much. Seemed to me that sundresses are designed for nudity under them. My sundress had a built-in bra, and but allowed me to show my chest pretty far down.

Several people saw me drive into some of the Parkway's parking areas, but no one seemed to give a shit what I wore. I did not get too close to the people up there but saw that I easily got away with showing a lot of skin "as a woman."

My next Parkway adventure would be bold, erotic and scary to boot. It would be a major turn-on for me if I dared. I was too turned on not to try it.

I decided to go up to the Parkway about 530 in the afternoon wearing only my wig, eye-shadow plus by blue bikini top and bottoms. I took some flip-flops in case my car broke down, but kept them behind my seat. I only wore the skimpy bikini--I had no extra clothes to change into if I got pulled over for anything. What a rush. A lot could happen.

I drove up the Parkway 70 miles from home, 70 miles from my clothes. After driving nearly an hour and a half in my bikini I had to pee. I felt under my seat, and soon realized it was not there. I had forgotten my plastic urinal I kept under my car seat. I'd cleaned it after my nude trip to Florida, then forgot to put it back in the car. I had it in the car during the last few days of my Florida trip so I could drive nude longer without stopping. I could pee into the plastic bottle and keep driving naked.

But now I had nothing good to pee into. I had to get out of the car and take a piss at a popular mountain overview parking lot. I thought about getting out naked, but opted to be dressed as a slut instead. I wore the tiny bikini. The bottom was small enough to ball up and fit into my hand. The top barely covered "my tits."

So I pulled off the Blue Ridge Parkway, pulled my bikini down and started pissing on the grass just off the edge of the pavement.

It was still light, but getting darker. Suddenly I saw truck lights coming my way. I quickly pulled my bikini up, but pissed all over myself. My bottoms were wet. I raced to my car barefoot. My flip-flops were in the car. I greatly enjoy driving barefoot. But before I pulled out, a green truck pulled in. Had they seen me? I felt certain they saw me in the dim light. What was going to happen now? Oh lord!

I could see two men in the truck parked on my left side about five feet away. The passenger rolled his window down and glared at me. He yelled "Hey Missy, why did you run to your car? Are you afraid of us. We ain't gonna hurt you. We are friendly. Come over to my window."

I did not want to get out, dressed only in a wet bikini, wearing a wig and some make-up, but there was a shot gun in the truck window rack. I thought I could flirt with the men, but get away. I slowly got out of my car. "Come over here, we want to see your sexy swim suit, Missy," a tall white man said from the driver's side of the truck.

The thinner bearded guy who wanted me to come to his window then said, "let's see some skin, pretty lady, love your outfit."

For me it was terrifying and erotic at the same time. They got out of their truck, and all three of us walked under a tree. It was by now mostly dark, but their headlights and lights on top of their pick-up lit up the area well.

The bearded man approached me, pulled out a hunting knife, held it near my throat and said, "Strip, woman, let's see what you've got under your pretty suit."

I did not hesitate to strip. I was soon stark naked in a secluded wooded area on the Blue Ridge Parkway with two very horny rednecks who I bet were fixing to fuck me silly. At that point they still thought I was a woman, not a man crossdressed as one.

The tall guy looked at me closely. He seemed to be baffled, but turned on. He keep looking at me up and down, head to toe. Then my luck ran out. He said "Terry--this ain't no woman, we have been deceived. Might be a damned shemale, though, they've got a small, rock-hard pecker, man."

Terry, the bearded man, said, "not sure what we've captured here Bud, but I'm gonna fuck it. I like those tanned, shaved legs. Tits are nice, too."

Bud looked at me, and said, "hey, what in the hell are you trying to pull, sissy boy. Down on your knees. Suck my big fat dick right now and swallow all my cum."

I did, and secretly enjoyed it. Being made to strip naked in public by two strangers out in the woods was so hot I came a little bit myself. Man, what a rush.

As I was sucking Bud's cock, I glimpsed Terry, who seemed to be pulling his pants down. He was going to masturbate, I figured, then play with my body.

I was so exhausted sucking cock, I soon laid on the grass. I was sick to my stomach, swallowing all that sperm. The "masturbating" bearded man went to his truck, got something, and came right back. "Had to get some lube, sissy boy. Now you are going to get what you deserve for teasing us dressed up as a woman. You are going to get an ass-fucking by yours truly. Down on your hands and knees, and stick that fine ass out more, you damned pervert. By the way, I wish you were really a hot women, as advertised, but I love your birthday suit just fine."

I stuck my butt out. He rammed his dick hard into my ass. Hurt like hell at first, but then started to feel pretty damn good as he fucked me over and over. Glad he had some lube, though. I was wet anyway, but it helped make a bad situation much better.

Terry said, "Hey Bud, want some of this?" Bud said "hell, yeah, that guys got a nice, tight ass, like a teenaged girl. Looks and feels like a woman. Damn son-of-a-bitch is shaved. What a pussy."

He stuck his big dick up my ass. It felt better than the other guy, but I did not let on that I liked it. He fucked my ass about three or four times.

Suddenly there were lights in the distance. The rednecks threw me to the ground and left the parking area like scalded dogs. At first I thought good God, I am fucked now. Naked and stranded here.

I soon got up in the darkness after being shoved to the ground. I soon saw why they left so quickly. Three park ranger trucks sped by me on the Parkway at a pretty good clip. They had not seen my nudity in the darkness. Seemed to me like they were in hot pursuit of someone, maybe these men who had just had their way with me.

I decided to get in my car to stay warm. All my keys were still in the car. I was amazed. Surprised the rednecks did not take them. I drove away nude in the opposite direction of the two men and the park rangers. My bikini was ruined, the bottoms were stretched out of shape as badly as my ass was. The strings on my bikini top had been cut by that knife the bearded man had pulled on me. Guess he just cut it up for the hell of it. I'd taken the bikini top off myself. It was not cut up then.

I eventually drove down off the parkway and went into Asheville by another route. It was about 3 a.m. when I got home. I was nude, bruised, and sore. I took a shower and went to bed naked.

I woke up the next morning hard as hell. At first I thought I'd had the wildest, and weirdest wet dream of my life. Seemed so real.

Then my ass started burning and hurting like mad, plus my mouth was sore, and my throat was feeling rough, too. I knew it wasn't a dream--it was real. I'd been brutally assaulted and used by the two men, but I lived through it.

What a wild adventure. I got hard just thinking about it, but I learned how dangerous being "a woman" on a back road could be. I was damn fortunate to be alive. But I couldn't report it. It would certainly humiliate me too much and reveal my crossdressing habit, which I still loved.

I would learn from it and plan safer crossdressing adventures. For starters, I needed a new bikini. Then I'd scout the area for good fast-food places for my nude drive-through adventures to come.