I want to thank eigengrau. Your beautiful love story, Always Bigger Than Him, inspired me to write this.
*****
I sat at the bar, listening to the music and nursing a bourbon. I wasn't quite sure what I was doing there. At twenty-nine, the clubs were starting to get a bit old. I found very few of the women to be really attractive - that plastic, post-disco look doesn't really do it for me - but where else is there to go on a Friday night when you're alone, as I usually was these days?
I'm not a bad looking guy, and I don't pick my nose or fart in public, but I was beginning to realize my dilemma. Most of the women around my age were married or otherwise paired up. I was a bit too old for the recent college graduate crop, and a bit too young for the newly-divorced ladies tentatively re-entering the dating pool, although I had had a couple of very brief flings with two of them. They were more attractive than the recent schoolgirls, but I found I didn't really enjoy being someone's rebound fuck as they once again ventured into the single world.
I took a sip and looked up to see Wendy walking up to me. Wendy is an old friend, and a strikingly beautiful woman, but we don't hook up. No chemistry. Oh, we tried it a few times a while back, but it just wasn't working for either of us. Wendy dates a lot of men. "Bobby! Buy me a drink!" she announced as she walked up next to me. I signaled the bartender and ordered her a gin and tonic.
"What's up, Wen?" I asked her.
"I'm glad you're here," she replied. There's someone I want you to meet. A woman."
I looked around but didn't see anybody nearby who looked likely. "Well, bring her over."
"Silly boy," she countered. "She's not here now. She works at my office. Just started a month ago. She's really sweet, she's not seeing anybody, and I thought of you."
I love it when Wendy looks out for me. "So?" I asked.
"Meet us at Gus's for happy hour tomorrow, say five o'clock. I've told her about you, and she wants to meet you." Gus's is a quiet neighborhood bar we sometimes go to. Much more conducive to conversations about work, philosophy and sex than the dance clubs, where you can't hear yourself think.
I didn't ask Wendy what this girl looks like. Like I said, she looks out for me, and I know it'll be fine. The woman might not be Miss America, but she won't frighten small children either, and that's enough for me, at least to find out more. At worst, we can have a drink and go our separate ways, like civilized folk. Wendy finished her G&T and walked back to wherever she came from. After a bit, I settled up and went home.
The next evening, I arrived at Gus's a little early, found a table and ordered a whiskey. I was checking my phone for emails when Wendy walked in with an absolutely stunning woman at her elbow. Well, maybe not quite as beautiful as Wendy, but definitely up there. I stood up, and Wendy made introductions. The woman's name was Michaela, and she had long chestnut brown hair and a smile that enchanted me immediately. She was tall, only a couple of inches shorter than me. We all sat down and ordered a round of drinks when the waitress came by.
"Michaela is a design engineer at my company," Wendy informed me. Then, looking at Michaela, "Robert is a marketing account manager." She never refers to me as "Bobby" if we're with anyone else. As we chatted, I asked Michaela about the products she works on, and described briefly the work that I do. The conversation got around to music and movies, and then Michaela told me about a book she had just read, a pretty deep novel, not a drugstore paperback - a good sign. Through it all, her eyes remained locked on mine, and that smile never faded. I felt the beginnings of a connection.
Wendy felt it too, because after a couple of drinks, she excused herself, saying something about having to meet her mom for supper. Michaela and I talked on, and eventually I asked if she'd like to walk down the block to a place I know for a casual bite of dinner. She agreed immediately. I paid the tab and we left.
At the restaurant, we ordered steaks and salads, and a bottle of wine. The conversation continued, with me asking Michaela lots of questions about herself, her likes and dislikes, how she spends her time, and so on. But I never asked the one question that was screaming in my head, "What is a beautiful, accomplished woman like yourself doing alone?" After the meal, I walked her the few blocks to where her car was parked, and before she got in, I leaned over to give her a quick goodnight kiss. She reached up and pulled me in, and the kiss went on much longer than I had expected. "I'd like to see you again," I told her.
"I want that, too, Robert," she affirmed. "Call me." I told her I would, and she drove off.
Later that night, masturbating at home alone, I could not get Michaela out of my mind. Her brown hair, her eyes, her smile. I was captivated. After a long time, I slept.
Two days later, before I could call Michaela, she called me. "Can you come meet me at my place." she asked. I said I would, and she gave me her address. I wouldn't have been surprised if she had asked me on a date, but what was this meeting at her place all about?
When I arrived, Michaela let me in, offered me a whiskey, which I accepted, and invited me to sit down. "Robert, please," she implored me, "there is something I have to do. Please don't do or say anything until I've finished."
What, I wondered, is going on here? And then, without a word, in front of me, Michaela started to strip. She began by unbuttoning her blouse, revealing a lacy bra. Slipping out of the blouse, she unhooked the bra and removed it, exposing exquisitely shaped, not overly large breasts, with hard nipples riding up high. I started to stand up, to hold her, but she stopped me cold, putting me back in my seat. "Not until I've finished," she repeated. I sat back to let the scene unfold, with thoughts of making love to Michaela's delicious body running through my head.
She turned her back to me and began unfastening her slacks. Sliding them down revealed skimpy pastel panties covering a nicely shaped, if slim, ass. Lowering her panties confirmed to me that her bottom was as lovely as I'd imagined. She smiled at me over her shoulder. My erection was pressing tightly against the inside of my pants as I watched Michaela bare herself for me. My emotions were a mixture of raw lust and the warmth I had felt for the woman in hours of conversation two evenings before. I started to speak, but caught myself in time, remembering her admonition to me not to do or say anything.
Then she turned to face me. And there it was. A slender, nicely proportioned penis hanging down between Michaela's legs. Uncircumcised, her (her?) foreskin hung well below the tip of her glans. Smallish, smooth shaved balls hung behind, up close to her body. Above was a thick thatch of chestnut brown pubic hair, the edges shaved, crisp and sharp, into a box shape, but full and hairy in the middle.
My mouth dropped open, my erection disappeared immediately, and I couldn't stop staring. "I don't sleep with men this soon," she began, "but I really liked you the other night. I mean, I REALLY liked you, and I got the feeling you really liked me, too. You were interested in me as a person, my work, my life, and not just as a possible lay."
My mind was going a mile a minute. I couldn't take my eyes off that cock. How can this work? I've always been a penis and vagina guy. I'm not gay. I don't sleep with men, even men who dress like women. Michaela read my mind. "Relax, Robert," she said gently. "We're not making love tonight, although we will, soon, if you're still interested. I'm a woman, not a man. I had the top surgery and I take the hormones. I live as a woman full time, ever since I moved here after school. I do woman things and I think woman thoughts. I adore men, and I'm beginning to adore you. Nobody knows about me other than my family and closest friends back home. No, Wendy doesn't know. She's a sweetheart who just thought she was introducing you to her new girlfriend. No, we're not THAT kind of girlfriends. We're the kind of girlfriends who sit around in sweats on Sunday, eating popcorn and watching rom-coms on cable."
I tore my gaze away from her crotch and looked up at her. Those eyes. That smile, a bit more tentative than before. My heart melted and my life changed forever. All the jokes and ugly comments about trannies, shemales and chicks with dicks simply flew out of my head. I reached forward and held her soft penis in the palm of my hand. "Michaela, this is beautiful. You're beautiful. The most beautiful woman I know. Yes, I'll be your lover, if you want. I'll need some help understanding how all this will work, but what I know is, I want you. This," squeezing her penis gently, "doesn't change that at all." I stood up and gave her a big kiss.
Tears appeared on her face. "I'm so happy," she whispered, holding back sobs. "Like I said, I'm not this fast, but I had to show you. It would have been unfair to date for a while and then spring it on you when we were ready to make love. I want it all. I want you to possess me, to take all I have. My mouth, my bottom. I'll always have a penis, never a vagina, and I can't change that. If you can't deal with it, now's the time to run." I stayed put. "But you also need to know I want to take you, too." I started to worry. "I want to have your mouth and your bottom as well."