One Step Too Far Ch. 01

Author Note: When I was 28, I was a shy closeted Asian crossdresser who only dated sparingly. Yet I responded to an ad for a man asking for something more than my cautious nature would ever allow. We exchanged a bunch of email and I seriously considered his offer. This story imagines what might have happened if I decided to go to him, a fantasy that replays once in awhile in my head.

*

My palms were sweaty on the wheel of my faithful Corolla beater headed east on highway 580. I felt vulnerable, my 5’7” frame in a little black dress, thigh highs with the silicon to hold them up and modest silvery heels from Target.

Why was I even on a highway driving away from the safety of the bay area? A car pulled up beside me and my high heeled foot leaned gently into gas, coaxing my reluctant car up to 80. As my Corolla shook, I felt a shiver. Either from the fear, the adrenaline or maybe just bounced around by my car. I adored driving dressed, fan blowing air lightly up through my dress and panties. But I could hardly enjoy driving today worrying about what I was doing.

Why do I feel compelled to keep taking bigger risks with my dressing? My parents are Chinese immigrants. They taught me to be hard working and to be ambitious but just as importantly to do so while not sticking out, not to attract attention by being inappropriate. Now at 28, in the fading light of California’s Central Valley, in hastily applied makeup and 3” heels probably with the price still on bottom, I felt regret for what hadn’t yet happened. I felt inadequate in my thrift store attire and yet I felt I had some appeal, nice legs, butt and feet (or so I’d been told), I was cute, naturally hairless and toned and submissive but sassy as a defense mechanism as I was generally unsure of myself, gawky and legs akimbo.

My first dates in my early 20s were awkward. The boys smelled of liquor (as did I, drinking for courage) and insisted they were straight even as they fumbled with my many clasps and buttons. I gravitated to older men who seemed more refined and knew how to flirt with a woman. I loved listening to them talk about their experiences and they seemed to appreciate me by their side, even if in secret. They would leave after a few dates to avoid arousing suspicion with their wives or girlfriends which felt fine for me, no need to deal with complications. I felt Ii could do this carefully forever. I felt like the gurl I wanted to be.

But then why was I driving away from the safety of coastal California east to an unknown, conservative, white community dressed as a woman? I felt a little like a robot (albeit a nervous one, and one wearing hosiery,) because I felt like something or someone was leading me and I was powerless to stop despite strong misgivings. Probably the reason I felt compelled was somewhere in his original ad, which was something like this:

“Older man in Central Valley (I leave the city out). I’ve done well for myself and semi-retired in a somewhat remote community. I have two gurls living here and would love to invite a third to come live with me, Fenny and Tiffany on the ranch. I will be direct. I would like for you to be cute with nice legs and available to me in the mornings to get on your knees so that I can cum in your mouth. Also I have friends with interests like myself who come for dinner parties from time to time and would like you to make yourself available to them at my discretion. In return, I will provide you with a beautiful private room in the country, near the other girls if you want their company and the ranch grounds are yours to play in but, you can’t leave or contact friends except to tell them you are ok. You needn’t work. Home cooked meals every day and a generous budget where you can order any clothing you like online. I require a 3 month commitment and you must be a woman 24/7.”

My first reaction when I read was, “What a crazy dude!” Who would give up their lives to pleasure you and your friends just for a room in the boonies and food?! I was a little angry with his presumption as I went about my week. But like my mom’s closet, I felt faint at times thinking about his proposal. The fresh air, a ranch, all the clothing and company of other gurls. But the most intoxicating thought was to be dressed 24/7. And he was oldish and there were three of us, surely I wouldn’t be called to give him a blow job often.

I responded to him with questions and asked for assurances. He responded the next day and was polite and responded positively to the photos he’d asked me to send. After a number of emails we agreed to a one week trial to meet the other girls and see the ranch. Just enjoy dressing in a private vacation spot. I agreed to do my best to please him, but I wouldn’t meet his friends, too little time. He said not a problem but keep an open mind.. He sent a picture of himself, about 6’ in his early 50s, cowboy boots and cowboy hat, strong hands and light blue eyes. My type. He told me in a week he might buy me an outfit and to bring my clothes, I’ll call him Alex for this story.

Six weeks later, I had made arrangements. My contract job was coming to an end and the thought of an all expenses week (or two if fun?) before going back to job market felt like a nice break. I had to be so furtive at home always risking discovery. I had snuck out of the house with a huge suitcase, made good time and arrived at Alex’s home just around dusk. I knocked on front door and my heart sank when nobody answered. I walked timidly around house and saw the expansive ranch. I could see two farm hands talking to a neatly dressed thin older woman. Suddenly I felt self conscious and out of place. Everyone looked so wholesome and for some reason I had decided to come dressed all in black. An Asian dressed for a funeral on a ranch. I backed away and snuck back to my car.

“Laura?!” I spun around and the old lady was walking up, extending an arm in greeting. “Alex told me you’d be here. You look lovely. My name is Ms Garvey, I run this place for Alex. If you like, I’ll take you to your room and have one of the men run your suitcase up. Alex will be back in an hour or so and if you are up for it, you two can meet one another. You’re so demure, how did you ever get that suitcase in your car?” We laughed at my forlorn misshapen suitcase as I handed my car keys to her. She handed them later to a farm hand who ran eagerly towards my car. Wow, I thought, a girl could get used to this. “Ms Garvey noticed my gaze and laughed, “Stephen is a bit dim, but he’s a good heart and he’s my son.” I laughed, he seemed happy.

I imagined myself a guest of honor, perhaps minor royalty from the Orient or something cool. I followed her, wobbly heels on uneven wood planking while looking at the pastoral setting. We arrived at an adorable row of cottages. Ms Garvey indicated the other two cottages were where the other gurls lived and hoped we would become friends. I started to tell her I would only be here a week but realized a week of sisterhood dressed full time would be plenty of time to become close friends.

The cottage was rustic and lovely, clean and faintly European. There was one large room with a bed and a nook for tea and snacks. Ms Garvey led me to the bathroom which was dominated by a clawfoot bath filled with suds. “I’ve taken the liberty of drawing you a bath. We leave girls soaps and perfumes over here and some nail polish, slippers, robes so you can feel human after your drive” Again an internal “ Wow”, as all my internal fears of judgement lifted away.

I could barely wait for the door to click behind her to shed myself of dusty stockings, ill fitting (but cute) heels, unzip my little black dress and “ahhhh” as I slipped gratefully into a bath of perfectly warm water. After 45 minutes of heaven I stepped out and into a slim fitting thick terry cloth robe, checked my sassy pixie cut haircut in the mirror and laid back onto a humongous bed with lambskins and fine thread count sheets. This... is... ridiculous. I thought about saying hi to the other girls and what I might wear for my first meeting with Alex.

I sat up slowly. The suitcase hadn’t arrived which seemed odd since the farm hand seemed so eager to get my suitcase. I padded in my bare feet to window but couldn’t see any activity outside. I went to go out but the door was a little stuck. It jiggled but I couldn’t get it open. No worries, more time to primp for later. I turned for the bathroom and froze. There was a man sitting very still in the tea nook watching me. How long had he been there? He got up and took his cowboy hat off. I recognized Alex and leapt to hug him, thanking him profusely for all the hospitality.

“I’m so silly, I can’t seem to figure out the door. And my clothes haven’t come up yet.” I said a bit too excitedly. He hadn’t said much and now regarded me quietly as if I were a child. Or maybe I just suddenly felt that way, feeling a little too giddy and nervous to be the kind of gurl who deserved all this. I was still sort of gesturing around when Alex reached out and touched my cheek gently but firmly as if to say, slow down, no need to rush. He had my attention and I just listened, unable to look at him directly.

He moved his hand down around my cheek and held my chin up. I naturally stood up a little straighter. almost obedient or something. He looked at me, His eyes still seemed kind as in the photo he emailed, but there was a kind of resoluteness to them. I glanced back at him, hoping he would say something funny. After a bit, he spoke slowly and firmly, “Laura, we need to talk, things have changed. The door is locked. I locked it. You won’t be needing your clothes for... awhile. You won’t need your car for awhile. They are both safe and will be returned to you when you leave.”

My eyes grew wide.