Backwards in High Heels:
More Missty Memories
© 2016 by Nom de Plume
The most romantic evening of my life, as man or woman.
I met Bill on an inauspiciously named website called TrannyDate. I know, it sounds perfectly dreadful, but I was coming off a bad breakup with a guy I went with for over a year – he took me out to dinner lots of times, sometimes I cooked for him and he’d spend the night, and the sex was pretty amazing. But he dumped me for a real woman, telling me that he was worried that we were getting too involved, and he’d better pull the ripcord before it was too late….
So, in desperation, I hooked up with a few guys on Craigslist (not to be recommended) before Bill found me on TrannyDate, which in my defense is part of a larger universe of websites called Adult Friend Finder. We’re all adults here, and most of us like to make new friends, so it doesn’t sound so bad, does it? I suppose I clicked on the link identifying myself as someone who is “TS/TV/TG” and said I was looking for a man, and up popped Bill. He introduced himself in a gentlemanly way, I asked for his email address, and we began a long-distance correspondence that became quite intense. He liked my pictures, I liked his, and soon we were planning our first meeting “in the flesh” at an Italian restaurant near the hotel where I’d be staying on an upcoming business trip.
It’s always such a rush getting dressed up as a woman to go out on a date with a handsome man! It never gets old, although that first date was something special: it was a sunny day in late March, and I selected my knee-length black skirt with crystal pleats, paired with a white tie-back top with black polka dots, off-black pantyhose and cute flats. We met in the hotel lobby, and he was very distinguished-looking and impeccably dressed (unlike so many guys who show up for a first date looking like bums) and quite a bit taller than me, which is always a plus! Anyway he seemed to approve of the way I looked, drove me to the restaurant, and we sat down at a quiet table for two, where we proceeded to get to know one another over a glass of wine, which became two glasses of wine and a lovely lunch.
There are some people who it’s easy to talk to, and who are fascinating to listen to, and that was Bill. We had so much in common! At some point he told me where he went to college, and I’m sure a big smile came over my face when I confessed that I went there too, although I hastened to add that I looked a lot different back then! He was quite a bit older than me, and I’ll confess that I had some mental reservations about how good he’d be in the sack, but that was secondary: we chattered away like a man and a woman, the only two people in the restaurant who were aware that the lady was not what she seemed….
When we were finished, I invited him back to my suite for dessert (I plan ahead and come prepared) which I served with a glass of champagne. On the way up, I’d surprised him with a little kiss in the elevator to break the ice, and once we sat down on the sofa, it was clear that his age was not going to be a problem. I excused myself so I could “slip into something comfortable” (a black nightgown and thigh high stockings) and we made slow, sweet love on my queen sized bed. He didn’t get as rock hard as some of the younger men I’ve known, but he got plenty hard enough for the “reverse cowgirl” position (look it up) before he gave me the most sensational blow job of my life, followed by more kisses and snuggling and a hand job that was just the way he wanted it.
When he left, I knew I’d see him again, and it wasn’t long before I was back in town. By then we were exchanging emails almost every day, and I stayed at a different hotel a little closer to him so we could have more time together. He took me to another charming restaurant, and this time I knew he was tall enough for me to wear heels. I wore them with a very pretty dress that the wind whipped around my knees after he parked his car, and as we passed two women on the sidewalk, one of them said to her companion, “I love her dress,” which made my day! Once again, after a delightful lunch and several glasses of wine, I had dessert and champagne waiting for him back in my suite, and once again we didn’t disappoint one another….
This went on for several happy months. One time, after an afternoon of blissful lovemaking, he suggested that we meet the next day on the campus of our old alma mater, just to walk around and share some memories. It was a warm, sunny day, and it was such a trip for me to stroll the familiar pathways in a skirt and sandals, hand-in-hand with my man, wondering what the youthful me would have thought of myself? I was all boy back then, making it with cute coeds, and now I’d returned as a woman, holding hands with a “fellow” alumnus who’d become my lover. Like I said, quite a trip!
* * *
Most of our trysts were during the day, but one time Bill asked me if I’d be free for an early dinner. Of course I was thrilled, and I put on a new dress and heels for him. After a lovely dinner at yet another charming Italian restaurant (I think Bill knew the owners, who treated us like royalty) he drove me to my hotel. He was in the mood for something new, “intercrural sex” he called it, which the ancient Greeks (and boys at Ivy League colleges) had practiced on one other. After I took off my dress and nylons, the fun began: the idea was for the girl to lube up the area between her thighs so the guy could slide in between them without penetrating her. It sounded like fun, and I was game for anything with Bill, so we played like that for quite some time before we eventually pleasured each other the usual way.
It was a few days later when I got a very disturbing email from Bill. I’ll give him credit, he didn’t beat around the bush: he’d come down with an STD, and he was concerned that he might have given it to me too. I should hasten to add that this was not H.I.V., but still it was something nasty that might require medical attention. Sure enough, a few days later I came down with the symptoms, and my next email to Bill was not very pleasant: could he please get the necessary medicine and courier it ASAP to the P.O. Box which I used to buy things as a woman? He responded at once, sent me the same meds which his doctor had prescribed for him, and I spent a miserable few weeks curing myself of the nasty disease he gave me.
Although I thanked him for telling me, and for taking care of the cure, I made it clear to him that I was furious with him, and that our relationship was over. Seeing him had become an existential threat to my life, and I didn’t want to take any more chances with him, or with any man for that matter. He said he understood, hoped that perhaps we could see each other again someday, and our once-daily exchanges of witty emails stopped cold turkey.
* * *
Months passed, summer gave way to autumn, and autumn turned to winter. Of course, it was impossible for me to give up dressing as a woman, but life wasn’t the same without Bill. I missed him! Occasionally he would send me a brief email asking me how I was doing or telling me about something that he knew might interest me, but I was very curt with him, although he was always apologetic. Then one day, when he whimsically asked me what it would take for me to forgive him, I told him that if he were ever to agree to take me to the Top of the Mark in San Francisco for a night of dinner and dancing, I might just find it in my heart to give him another chance.
I should add that ballroom dancing as a woman was something between a fantasy and a fixation for me. During the long, lean months after Bill and I broke up, I joined an LGBT square dancing group which some of my crossdressing galpals had told me about, and had the time of my life twirling and curtsying around the floor. I even bought a petticoat to wear under one of my skirts.
But as much fun as I was having with the gay boys, it wasn’t the same as dancing with a lover in a crowded ballroom, having him hold me in his arms and take the lead as we waltzed across the floor to the old, big band sounds that Bill and I both adored. He knew, because I’d told him many times, that I had the perfect little black dress for a night on the town, but he was a well-known figure in San Francisco, so the prospects of him asking me out to a popular nightspot were dim.
Well, guess what: it seems that he missed the things we did under the sheets as much as I did, because one day he threw caution to the wind and told me he was up to my challenge! We set the date, I booked a hotel room across the Bay (courtesy of my expense account) and I packed a suitcase for my dream date: black teddy and slip, garterbelt and sheer nylon stockings, strappy heels, a little clutch purse, some sparkling bling, a black pashmina shawl and my little black dress – the last time I’d worn it had been in Las Vegas during a girls night out with my bestie, and it had turned a lot of heads at the craps table!
But would it pass inspection at one of San Francisco’s most fabled nightspots? The Top of the Mark was on the top floor of the Mark Hopkins Hotel at the top of Nob Hill, and I knew that Bill would be wearing a conservative suit and tie. Would I be able to pass in polite society as the woman on his arm? The fact that he even asked me was a huge vote of confidence, but I was more than a little nervous as I shaved my legs in the bathtub before I began to get dressed for my dream date. My garterbelt and nylons went on first, and just like that first time all those years ago, it took me forever to get my nylons securely fastened under those pesky tabs. Next I stepped into my teddy, and then my slip, which felt terrific when it brushed against my stockings. I padded myself up with expensive silicone breast forms and hip pads, and then it was time to put on my makeup. I took a little more time than usual, adding some special flourishes for evening, and after I put on my wig I styled it with a bit of hairspray to give it some extra bounce.
Carefully, so as not to muss my hair, I lowered my dress over my head, a knee-length black number which clung to my artificial curves. A sparkling faux diamond pendant and dangling faux diamond earrings were next, and then I struggled to fasten the straps on my heels, which wasn’t easy! But it was all worth it when I draped my shawl around my shoulders, and studied my reflection in the closet mirror.
Stuffing all my female essentials, wallet, cellphone, etc. in my little clutch purse was quite the challenge, but eventually I was all dressed up with somewhere to go! Bill was right on time, and he had a big smile on his face when I hopped into his car. “Look at you!” he beamed. “Your jewelry matches your shoes!” It was true that my strappy heels had little faux diamonds on them, and I commended him on his powers of observation. He squeezed my knee like he always used to - I loved the sensation of his hand on my nylons as much as he loved to touch them – and I surprised him by pulling up my dress to reveal the tops of my stockings. “Omigod, real stockings! You’re such a girl!”
I was back in his car, he was back in my life, and all seemed right with the world as he drove over the Bay Bridge and into San Francisco. We chattered away like long lost lovers, which of course we were, all the way into the City. I was so excited! When he got to Nob Hill, he parked in a garage a few blocks from the hotel, and I was glad I’d brought my shawl, which provided just enough warmth against my bare shoulders as we walked through the brisk evening air.
I can remember walking into the elegant lobby of the Mark Hopkins, and waiting with Bill for an old fashioned elevator to take us to the Top of the Mark. It was paneled in some kind of exotic wood, and I glanced sideways at the other well-dressed couples as we zoomed to the top, but they were all preoccupied with themselves and didn’t seem to notice or care that one of the elegantly dressed women was actually a man. When we got off, Bill marched to the maître d’ and scored us a fantastic table, right off the dancefloor with a spectacular view of the Golden Gate Bridge.
The orchestra wasn’t scheduled to start playing for over an hour, so we had plenty of time for several glasses of wine and a fun dinner featuring small plates of lasagna and other delicious dishes. At one point, I felt Bill’s hand under the table cloth caressing my legs, and I tugged my chair a little closer to his and let him feel away, so happy to be back in his world. If he was self-conscious or concerned about being spotted with a transvestite by one of his society friends, he didn’t show it, and as always we talked about small things, man-and-woman conversation as we enjoyed our dinners. After we finished, I excused myself to visit the ladies room, and after I took care of business (thankful that I’d put on my garterbelt and stockings first, so I didn’t have to take them off, an old female trick I’d learned somewhere) I freshened my makeup in the mirror, fussed with my hair, and returned to my man.
Finally we heard some tinkling on the grand piano, and turned to see the orchestra – which was really a three or four piece combo – getting ready to play. The first tune was rather fast, and we sat back and waited for something a bit more sedate…for a moment I wondered if Bill really had the courage to ask me to dance, and thought we might just sit there all night like wallflowers, but then they started to play an old standard, and he asked me if I’d like to dance! I was out of my chair before he could change his mind, and the videos I’d been studying paid off: let him take your right hand in his left hand, place your left hand on his shoulder, and step back with your right foot as he takes the lead. I felt Bill’s right hand pressing into the small of my back, just like I used to do with girls when I was a boy, and soon we were gliding across the dancefloor. It wasn’t as hard as I thought, dancing backwards in high heels, with a confident partner to guide me, and I just let go and lived for the moment, which was as wonderful as I’d imagined it would be.
When the song finally ended, we made our way back to our table, and I thanked Bill profusely for being such a good sport. He seemed bemused, and we watched for a while as some other couples gyrated to a peppy number. Then the band broke into another slow standard, and he asked me to dance again! This time it felt so natural, being the woman in his arms, as he squired me across the floor. One of the walls was mirrored, and I caught myself staring at our reflections while we danced – we looked pretty good, like we belonged there! We danced some more, and then it was time for Cinderella to turn back into a pumpkin – well not quite, after Bill drove us back to my hotel, I invited him up for a cup of coffee. The elevators in my hotel had glass sides overlooking the atrium, and if anyone happened to glance up, they would have seen a smartly dressed couple exchanging a deep, soulful kiss, all the way up.
When we got to my room, Bill helped to undress me – he seemed fascinated by my stockings and garters – and I helped him get undressed before I excused myself, as always, to slip into a babydoll nightie, choker and black thigh high stockings.
That night, we got our mojo back. Bill gave me a sweet, lovely blowjob, and after I came back from heaven, I suckled him for a while before I gave him the kind of handjob that he loved: lots of lube, with me tucked under his arm so he could kiss me, and when he came I was the happiest woman on earth.
I put on a robe and slippers and made some coffee while Bill got dressed. Before he left, he surprised me by asking if I wanted to have lunch with him the next day in San Francisco. “Be still my girlish heart! Where and when?”
“A café off Union Square (I’ve forgotten the name) how about noon?”
“I’d love to!”
* * *
The next morning, I was up early for a jog (as a guy) before I took a quick bath, put on my wig and makeup, and dressed myself in a gray skirt suit with a bow blouse, pantyhose and sensible flats. I rode the glass elevator down to breakfast, and after I enjoyed an omelet and cup of coffee with a cigarette outside, I walked over to the BART station for the ride into San Francisco with all the other worker bees. I loved doing this, playing the working girl, which was such an escape from the manic pressures of my male existence.
When we pulled into San Francisco, I got off at Montgomery and did a bit of shopping on Market Street until it was time to head up to Union Square. Bill was waiting for me at a corner table with a view of the ice rink. He had a little present for me – a book which he thought I’d like to read – and we sat back and lingered over a long, delightful lunch, with wine of course, only there was no prospect of sex on the immediate horizon: Bill simply asked me to lunch because he enjoyed my company, and we sat there and talked like an old married couple for the rest of the afternoon.
* * *
That evening, I returned to San Francisco once again, driven this time by the crossdresser who’d accompanied me to Las Vegas. I’d been sort of a mentor to her at first, coaching her until she made her debut as a woman, but once she was out it was like watching a butterfly emerging from a cocoon – now she went out way more than I did, she’d assembled a massive wardrobe with incredible style, and she was always making new friends. That night she introduced me to her latest galpal, and we had a fun girls night out at some of her favorite haunts.
I’m sure I made the other girls jealous when I regaled them about the most romantic evening of my life, as man or woman.
