Don't Ask... - Cover

Don't Ask...

Rachael Ross 1982 - 2012

Chapter 2

Erotica Sex Story: Chapter 2 - A former Air Force officer relates the personal story of his lifelong infatuation with transsexuals. More or less a true story as related to me by a reader who wondered if I wouldn't care to write on the subject.

Caution: This Erotica Sex Story contains strong sexual content, including Consensual   Romantic   TransGender   First   Oral Sex   Anal Sex   Masturbation   Petting  

I spent my first two years in the Air Force at school. All kinds of schools, the biggest of which was flight training. I wanted to be a fighter jock, like everyone else, but I didn't make the cut, although it was close. I ended up flying FB-111's my first tour and I was one busy lieutenant. Between learning the aircraft and getting my hours, to simulator time, to more leadership training, plus having to baby-sit a couple dozen airmen, it didn't leave a whole lot of time for fun and games.

This was right after Vietnam too, so everyone it seemed had medals and ribbons and stories to tell, except for me of course. I was kind of disillusioned with it all really. Morale was low, the equipment wasn't in the best shape, we had a high turnover in people with experience, recruiting was down, and on and on and on. I was in California then, up near San Francisco, and very lonely. Letters from Heather and the memories they brought back sustained me for awhile and I'd met a girl through one of the guys I worked with. Her name was Janice and she was nice, to be sure, attractive and fun, but not exactly what I was interested in.

San Francisco has always been on the edge, as everyone knows, maybe it's that mindset that the whole place could slide into the Pacific at any moment, I don't know. I'd found a few clubs that seemed geared towards transvestites and transsexuals, but they were notoriously gay and I only ventured in a couple times, figuring I could plead innocence if anyone caught me. I'd have a couple beers and check out the girls and then beat a hasty retreat. I was a bit of a coward, I admit.

I was also horny as hell. I'd seen some extremely attractive t-girls, I'll call them that, because really it was impossible to tell if they were pre-op transsexuals, or just amazingly adept transvestites. Either way, there were more than a few who absolutely knocked my socks off and that was what kept bringing me back. I'd get excited enough on these little visits to go back to Janice and make love, closing my eyes and imagining she were a t-girl and that almost made it bearable. As you can imagine, after six months or so of this I was just about going crazy.

One place was called The Gold Rush, although it has long since been closed down. It was a very large club and a popular place, especially on the weekends because they always had things like beauty contests, wet t-shirt contests, and the like. I used to go in and pretty much keep to myself, just looking around and having a beer or two. I was always nervous and a little self-conscious, but I probably didn't need to be. There were probably 300 people in there on a good busy night, maybe a hundred of them dressed, and the most of the rest patently gay, usually in the loud and proud style. But there were always a few guys like me here and there, very normal looking, not gay at all. At least outwardly.

It was maybe my 8th or 9th time in the place over several months that I finally just had to talk to one of the girls. This was more out of need, than any newfound nerve. I've never been very shy, I always figured the worst that can happen is nothing. Anyway, there was one particular girl I'd noticed almost every time I'd come in and sometimes she was with someone, sometimes not. A few times previously she'd come close to me as I sat at the bar and we'd said hello, but that was it. This night it looked like she was alone, but I'd seen guys talking to her, and she'd smile and shake her head, and they'd leave. So maybe she was waiting for someone.

It was still relatively early, around 8pm and the place didn't pick up until about 10 usually, so I figured if I was going to do it, this would be the best chance I'd get. She was tall, maybe 5'10 in her heels, with lustrous dark hair that fell in waves around her pretty face. She had high cheekbones and a small little mouth with soft pouting lips. I always liked that kind of look for some reason. Her eyes were soft brown and very expressive, which I also liked. Her body was great and she'd had some breast implants, because I'd seen her a few times in the wet t-shirt contest, and they were nice C cups, with hard little nipples that were dark and sexy. She couldn't have weighed more than 130lbs, if even that much, and her stomach was flat and her hips nice and round. If you saw her on the street it would never even occur to you that she was a guy.

But she had a cock, that was for sure, because the fun thing about a t-girl wet t–shirt contest is that it's also a wet thong contest and they use very thin cotton panties that become just as transparent as their t-shirts, if not more so. It can be incredibly sexy seeing a beautiful woman soaking wet so her breasts strain against her shirt and then look down to see the all too visible size and shape of her cock straining against her panties. Some of them were obviously better endowed than others, and this girl was pretty good. I didn't know how functional she was of course, taking a lot of female hormones can really cut down on a t-girl's ability to get hard and maintain it. But that was alright too, I didn't particularly require her to be hard as a rock to enjoy being with her, although a lot of guys do.

I made my way over to where she was sitting at the bar and I was smiling a little nervously, I suppose. I was dressed nicely and I looked good, I knew, being in the Air Force wasn't the most physical thing in the world, but I ran a lot, spent a lot of time in the gym, and it showed. I was 25 then, but still had my boyish good looks and a really sincere smile that's gotten me out of a lot of trouble. So I felt reasonably confident when I said hello.

"Hi." She smiled up at me and her voice was nice, very feminine and not at all forced. I'd noticed that before and it was another reason I found myself drawn to her instead of some of the others. She didn't need to whisper, or adopt some weak falsetto, she was very natural.

"I was wondering if I could buy you a drink." I offered and I wouldn't have been totally surprised if she turned me down, but I was very glad when she didn't.

"Sure, that would be great." She nodded and her eyes were bright. "Maybe we could sit over there." She gestured to an empty little booth and I took her hand, helping her stand up. She was wearing a little red miniskirt and a loose tank top with an orange bikini underneath it.

"Are you going to be in the contest tonight?" I asked her. It was a swimwear contest tonight and she nodded and said she was. "Well, I hope you win then."

"Thanks." A waitress brought our drinks and we sipped them a moment before I remembered my manners.

"My name is David."

"I'm Susan." We shook hands gently and I loved the way her fingers felt, small and delicate. "It's nice to meet you finally." She gave me a little grin.

"What do you mean?" I asked, smiling myself although I wasn't sure why.

"Because I've been waiting about a month for you to say something to me."

"Really?" I sat a little straighter in surprise. "I didn't think you even noticed me." I laughed a little.

"Oh there's a few girls here that have noticed you, some guys too." Susan took another sip. "I was beginning to wonder if you were a cop."

"What?" That really did surprise me. "Why would you think that?"

"Just the way you look, the hair I guess. And the way you just hang out for a little bit and leave. I've never seen you talk to anyone."

"I guess I'm just shy." I grinned.

"So are you a cop?" Susan laughed at me.

"No." I shook my head. "I'm in the Air Force." I leaned close and said it kind of quietly. "This place is kind of off limits, so..." I shrugged. "I don't usually stay too long."

"Oh. I see." She nodded. "My brother is in the navy, he hates it."

"Yeah, me too sometimes." I answered. "Hey, I know this is really fast, but uh, do you think you'd like to go to dinner with me sometime?"

"I'd love to go to dinner with you." She smiled. "Anytime."

"Wow ... okay ... Mmmm..." I looked at my watch.

"Sure." Susan giggled and grabbed my wrist, giving me a little squeeze. "Let's go."

"Do you always read minds?" I chuckled as we stood up.

Susan let me put my arm around her narrow waist as we started walking. "No. I'm much better with body language!" She gave me a little smirk and I was feeling pretty good right then.

She retrieved her purse and a men's leather jacket complete with silver buttons, buckles and zippers. I helped her into it and the effect was tough and sexy and suited her perfectly, I thought. Combined with her miniskirt, the jacket really set off Susan's long tanned and toned legs, and her ass looked incredible. It pushed and pulled against her skirt seductively, tempting me in ways the devil himself couldn't have imagined. But it was Susan's smile and the way her eyes drew me into it, that really made my heart flutter.

We took a taxi for the short drive to Chinatown, leaving my Mustang where it was. One thing about San Francisco – you never give up your parking place if you don't have to! And besides, it gave me just a little more time to focus on Susan, sitting close beside her in the backseat.

During the evening we talked a lot. It was a relief to find Susan every bit as intelligent and engaging as she was beautiful. Perhaps I'm biased, but I will say from my own experience that the most successful transgender people, men or women, are often very smart, very imaginative and expressive. And when I say successful, I don't just mean passing physically, but adjusting emotionally and socially, which can be much more difficult. I can honestly say that at that point in my life I had no idea how lucky I'd been. With Denise, Marie, and most especially with Heather, I'd been with people who were reasonably happy and making progress towards where they needed to be in life. This wouldn't always be the case.

But Susan ... She was another lucky break for me, without a doubt. She was 24 and had been living as a female since she was just sixteen, when she'd run away from home. She told me how she'd always known she was a girl and how her parents had tried to deal with that, largely unsuccessfully. Susan didn't go into great detail, but I could sense there were still issues there. She'd come to San Francisco and found herself living with a succession of boyfriends, all bears, as she called them. Very macho sort of gay men and none of them interested in Susan as a transsexual. She was pretty unhappy for a long time, very confused because she obviously didn't feel comfortable in the straight world and it seemed she wasn't going to find what she needed in the gay community either.

I listened patiently, really wanting to understand and Susan appreciated that, I think. She was opening up quite a bit more than either of us expected, but maybe that was what she needed.

Eventually Susan had come into a small circle of male to female transgender people, about a dozen she told me, some of whom were like she had been, just taking the first baby steps towards an uncertain goal. Others had gone so far as breast implants and legal name changes, and at least one woman had gone through the full sex change operation. This small community became Susan's whole world and she basically hid herself away until she was comfortable with whom she was. Comfortable enough to live and work every day as a woman in the straight world.

She'd changed her name, had spent almost every penny she had on breast implants, and was in the process of being screened into a sexual reassignment program sponsored by USC-Berkley. That was her biggest worry, Susan confided to me. She needed to be accepted to get her sex changed and even if she was, it would still be frightfully expensive. This was late summer 1976 and while the university would absorb more than half the costs, it would still leave her with some 35 grand or so in medical bills.

Listening to Susan talk was a real eye-opener for me. I'd never really considered all the problems someone like Susan faced. I mean I'd spoken with Heather quite a lot, but our focus had been largely on emotional things. Here now, with Susan, the emotional stuff was there, but compounded enormously by the tangible, physical problems –the monetary problems, to put it bluntly. Her hormone therapy, for example, cost nearly as much every month as her rent did.

Having said all that, I imagine someone might think Susan was just digging for gold, looking for someone to support her. But really, while we spoke I never got that impression from her at all. She wasn't trying to prostitute herself out in any way, nor was she expecting anything from me other than polite interest and understanding. Our conversation was nowhere near as deliberate and straightforward as I might have suggested. It was meandering and enjoyable and by the end of our dinner I was finding myself quite enamored of her and I think the feeling was mutual. I'd told her about my life, growing up, and about my experiences with former girl friends, real girls and otherwise. Marie seemed to baffle Susan a little, but she nodded appreciatively when I spoke of Denise and Heather.

We ended up walking around Chinatown for a long while. Susan told me it was her favorite part of the city and I'd never been there before. It was very enjoyable, probably because I had my arm around Susan's waist the whole time. She was beautiful and funny and it felt so right to be with her.

"I've figured it out." Susan said suddenly, pausing in front of store selling oriental carpets. They were beautiful and exotic behind the big plate glass window, but I barely noticed.

"What's that?" I smiled and turned to her, my hands lightly on Susan's hips.

"You're not playing a role." She said seriously. "Are you?" Susan's deep brown eyes were shining.

"No." I shook my head, not really understanding her. "I don't think so."

Susan took my hand and we started walking again, slowly. "I've had a couple ... boyfriends." She sort of hesitated on the word. "Over the last year or so."

"Okay." I shrugged. Susan hadn't really talked about her recent love history and while I was curious, I was trying to play it casual too, you know.

"Well, what I mean is that they were gay, those guys." She gave my hand a little squeeze. "They pretended that they were straight though. That I was a real woman and they were real men." She giggled just a little and it sounded wonderful.

"I don't..." I started talking but Susan cut me off.

"But you, Dave. You're not pretending, are you? I'm a woman, aren't I? To you." She'd stopped again and she was looking into my eyes and my heart was doing flip-flops in my chest.

"Yes." I smiled. "You are a woman, Susan. The most beautiful woman I've ever met." I did the only thing I could do then – I kissed her. A soft light kiss on her lips, brief and tender and chaste, the way a first kiss should be.

When I pulled back from it, Susan's eyes were wide and she blinked several times. At first I thought I'd done something wrong, but then I saw a little wetness in the corners, threatening to spill down her cheeks.

"Do that again." She whispered and when I did, Susan wrapped her arms tightly around me, parting her lips for my tongue and we kissed deeply for a long minute.

Someone spoke something in Chinese to break the spell and we both looked around a little self-consciously, and then laughed at ourselves. There were dozens of people all around us, of course, people who lived and worked there, as well as the tourists. Some staring, but most assiduously ignoring us. I forced myself to let Susan go and she did the same, taking my hand again as we started walking.

"What do you think he said?" I asked Susan, tilting my head close to hers. Her hair smelled wonderful.

"Um ... I think he was telling us to get a room." She grinned at me and I think I blushed just a little.

I was sorely tempted to take that ball and run with it, but I was desperate not to ruin a good thing. Susan didn't seem to be looking for quick sex and at that point, neither was I.

"Do you want to go back to the club?" I glanced at my watch, it was nearly ten already.

A brief look of something, disappointment maybe. Or relief, I couldn't be sure, passed over Susan's lovely face. "No, not really." She hooked her arm through mine.

"But the bikini contest..." I gave her a boyish grin.

"Ohhh..." Susan giggled and rolled her eyes.

I laughed and we walked a few minutes in silence. "Hey." I looked at her, getting serious for a moment. "Do you want to see my airplane?"

Susan stopped and turned to me. "I thought you'd never ask." She replied with a smile playing at the corners of her pouting little mouth.

I kissed her again, quickly because I just had to, and waved at a taxi. We went back to the Gold Rush, but only to climb into my car for the long drive to the base. It was a white Mustang convertible that my Dad had gotten me when I'd graduated college. I loved it and drove with the top down every chance I got, but San Francisco is a chilly place and I thought Susan's legs must have been getting cold, so I left the top up.

"Nice car." Susan smiled as I pulled into traffic, heading towards the Oakland Bay Bridge.

"Are you cold? I can turn on the heater." I reached over to put my hand on her thigh, just above the knee. It wasn't really intentional, I did it without thinking, but I caught Susan's smile as she looked down and put her hand on top of mine.

"No, I'm fine now." She said, looking up.

We talked mostly about me on the way to the base, about what my plans were for the future. I was afraid I was boring her, but Susan seemed interested. She asked a lot of questions and I didn't have answers to a lot of them. It was maybe the first time anyone or anything had made me ask myself what I was doing, where I wanted to be in 2 or 5 or 10 years. Of course Susan lived with planning her life like that, she had to. She couldn't just get by with living from day to day the way most of us do. Not for the first time that night, and far from the last time in our relationship, Susan had found the simplest and easiest means to teach me something about myself. And through that, I was learning more about her as well.

As I was turning off the freeway onto the exit for the base a sudden and terrible thought occurred to me. There was no problem with bringing a visitor onto the base, as an officer I could do it virtually any time I wanted and on a Saturday night the officer's club was full of pretty young visitors. But Susan would have to be logged into the visitor log that the guards kept. That would mean she'd need to show some identification, something with a picture on it. I tried to think of a way to ask Susan if she had one. I mean popping out a driver's license with her birth name, which I didn't even know, and a man's picture would be a little hard to explain.

"Uh, Susan..." I started, hoping like hell I wasn't about to completely embarrass her. "You'll have to show some ID at the gate." I swallowed nervously. "Like a driver's license, or a..."

"Oh, I have one." She smiled at me.

"Uh, what I mean is..."

"I know." Susan reached over and rubbed my leg reassuringly. "I had my name changed, remember?"

"Oh." I gave a little sigh. "I'm sorry, I just didn't want you to be embarrassed or anything." That was only part of the truth, I was worried about myself as well, and Susan saw through it immediately, as I suppose anyone would.

"Dave." She squeezed my leg so I looked over at her. "I understand, okay?" I nodded dumbly. "What matters to me is you didn't think of it until now." She giggled. "I like that."

"Oh." I smiled and laughed at myself.

"Besides." Susan leaned close and I felt her breath in my ear. "You're cute when you're worried." Then she kissed me as I turned towards the gate.

There was a sergeant on the gate and he saluted me smartly as he checked my military ID. Susan smiled at that and then at the young man as he retrieved his clipboard with the visitor log and asked for Susan's driver's license. He could barely take his eyes off of her long enough to write her name down and his voice had a nervous edge to it as he thanked her, returning her license and asked me where we were going.

"Flight line and the O-club." I told him and he wrote it down, saluted again and waved us through.

"He was cute." Susan was giggling.

"He was drooling." I shook my head.

"Aw, don't be too hard on him. Next time I'll wear something a little less..."

"Red?" I grinned at her.

" ... Sexy." She laughed and leaned close to me, giving me a little hug as we made our way slowly across the base.

"Oh, I hope not!" I resisted the urge to kiss her, deciding I needed to keep at least some bit of concentration on the road.

I was with a Tactical Bomb Wing at that time and we were going through our training cycle before deploying to Europe. There were sentries around the flight line and hangers, of course, but not as many as you might expect. We had no live ordnance, after all, and it wasn't a SAC base, thank God. So while visitors were officially frowned upon at the flight line, in practice it was the first place everyone wanted to see. Especially the women. When I was in flight school, and my class was all male I might add, one of our instructors had quipped that the Wright brothers had invented the airplane just to get in their girlfriends' panties. Pilots, and devious mechanics, had been doing the same thing ever since.

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