The Girl with Something Extra

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Robert's life takes a turn for the better.
9k words
4.43
16.2k
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Part 1 of the 4 part series

Updated 06/10/2023
Created 11/12/2020
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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."

"Michaela, I've never . . ."

"You've never been fucked in the bottom before, have you? You've never had a penis in your mouth? Don't worry, you'll know when you're ready. I'll be gentle when the time comes. It'll be fine. I do it, you can do it, too. There's no difference between us when it comes to those things." I realized she was right, of course.

"In the meantime, let me get dressed and let's plan to go out Saturday night. Do you like Mexican? I love Mexican, and I know a great place down by the harbor. It's time we began dating like real people."

*********************

The rest of the week dragged on, with most nights finding me at home with my stiff cock in my hand and my thoughts fixed on Michaela. When Saturday evening finally rolled around, I couldn't contain myself until it was time to leave to pick her up. Seated at the restaurant, we ordered queso blanco and margaritas along with the chips and salsa, and told each other about our week. Michaela looked lovely in a ruffled blouse, showing lots of cleavage, and a mid length skirt, and I told her so.

Dinner arrived, an enchilada platter for me and fajitas for Michaela. The food was excellent. As we shared a fried ice cream dessert, I felt a foot travel up my calf under the table. I looked at Michaela and she smiled that smile at me. Another round of margaritas and we left to take a walk on the waterfront. I put out my hand and Michaela held it, and I was at peace with the world.

Later, taking her back to her apartment, Michaela invited me in for a cup of coffee. When the coffee was ready, she brought it out and sat next to me on the sofa, snuggling against me. I put my arm around her and, after a time, turned to kiss her. Her tongue found its way between my lips, and I reciprocated, teasing her mouth as she teased mine. We kissed and talked and drank our coffee, until I finally said it was probably time for me to go. As I stood up, my arousal became plain to see. Michaela frowned, patted my bulge, and said, "You poor boy. We can't let you go home like that," and kissed me again. Pressing her hand more firmly against my front, she whispered, "I have one, too. Let's take care of them, shall we?"

I nodded and held her in my arms as she began unfastening my belt. She slid my slacks down and handled me inside my briefs before sliding them down my thighs. Freed from restraint, my penis sprung up, fully erect. Michaela smiled at it and whispered, "Oh, my!" while caressing it some more. I unbuttoned her blouse, reached behind to unhook her bra, and slipped them off of her in one motion. Holding her perfect breasts in my hands, I bent forward to kiss, and then suckle on, her nipples, first the right and then the left. I reached down to unfasten Michaela's skirt and remove it, leaving her standing in her panties, her erection obvious.

I gave my cock a couple of quick jerks, then pulled her panties down, exposing her penis. Erect, it was nearly as large as mine. I touched it gently, feeling its hardness, and then began sliding her foreskin up and down, revealing a glistening cockhead. I lowered myself to my knees, having built up my courage to take it into my mouth, but Michaela stopped me. "Not tonight, Robert," she said. "Tonight is only for touching and rubbing." We sat naked, side by side on the sofa, up against each other, softly stroking each other's hard penis. I continued playing with her foreskin while she cupped her thumb and first two fingers over my circumcised glans and rolled its velvety smoothness around in her palm. "Robert, it's beautiful," she murmured. "I'm going to want it everywhere, but tonight I just want to make you happy. So you can go home to sleep relaxed. And, please, I want to come, too. Or I'll be up playing with it at four in the morning."

We continued masturbating each other, as Michaela laid her head on my shoulder. I turned to kiss her, and we paused our cock-rubbing to hold each other and kiss some more. After a time, she went back to stroking my erection, and I hers. Soon, she squealed, and launched a jet of white come up to her breasts, followed by four or five smaller ones. This put me over the top and I, too, came all over myself as she pumped me. When I finished, I put my mouth on her nipple and sucked off a large drop of her own semen that had landed there. It tasted sweet, as if it had picked up a bit of her perfume. We hugged and kissed for a long while, getting our sticky come all over each other's bodies.

Eventually, Michaela went and brought a towel that we shared in wiping each other, getting the worst of the sticky off ourselves, so we, or at least I, could get dressed and leave. Michaela had made it clear that we weren't sleeping together, not yet. I drove myself home and fell asleep in bed immediately, dreaming of those eyes and that smile.

*********************

The next day, I phoned Michaela and we made plans for the following weekend. "But," I said, "I can't wait all week to see you again. When can we get together?"

"Oh, Robert," she answered, "I'm so glad you said that. I have to run errands tonight, but can you come over tomorrow night? Nothing fancy, just hanging out. Maybe we'll watch a movie."

"That sounds great," I said. "I'll bring dinner. Chinese?"

"Perfect. Bring some orange chicken and lo mein. Come by around six thirty."

I arrived at the appointed time, goodies in hand, to which I had added egg rolls and hot and sour soup. Michaela set up trays in front of the sofa, brought in iced tea, and put on a science fiction movie, "Predestination," a time travel thriller but also with a transsexual theme. We sat, ate dinner and watched the film, occasionally touching and caressing each other.

When the movie ended, we shared the cleanup. After everything was done, we returned to the living room. I took Michaela in my arms and kissed her deeply. Then, I slowly and deliberately undressed her, until she stood naked before me. I undressed myself as well, and moved close to her, touching the tip of my erect penis to the tip of hers. Kissing her once more, I slid down to my knees, not to be denied this time, and slipped my mouth around her engorged cock. Loving the feel and smell of her sex, hairier than mine, I retracted her foreskin and ran my lips up and down the length of her shaft, burying my nose each time in her dark pubic curls. Her fragrance there was a mixture of her natural musk and just a hint of her perfume, and breathing it in made me dizzy.

Placing my hands on Michaela's asscheeks, I pulled her body to my face and swallowed her stiff rod as far as I could, massaging her glans with my throat and reaching in to gently touch her asshole with a fingertip. She sighed softly and wiggled her butt around on my finger. Looking up, I saw her holding her breasts in her hands, and pinching her nipples. I made a ring with my thumb and forefinger tightly around the base of her erection and resumed sucking up and down, harder this time. Michaela rocked her hips back and forth to fuck my face, and then, without warning, she exploded a huge load in my mouth. I swallowed as best I could, but the semen kept coming, in shot after shot, and much of it ran down my lips and my chin. She moaned loudly as she ejaculated and finished by pressing her pubic fur firmly against my nose.

I moved to sit myself down on the sofa, and Michaela straddled my lap on her knees, facing me. "Oh, Robert, that was amazing! The best ever!" She kissed me hard, licking up the come on my lips. My swollen dick was wedged underneath her balls, and she shifted herself around on my lap to squeeze and rub it with her thighs. I kissed back and held her tightly, not wanting or needing anything more for the moment.

Michaela, however, was not so easily satisfied. Beginning at my mouth, she kissed her way down my body, pausing at my nipples to give them little bites, and again at my pubic bush, running her tongue through my hair there. Tickling my nuts with her fingertips, she engulfed my penis in her mouth and began giving me the blowjob of my life, her lips, tongue and mouth all over my cock and, as I had done to her earlier, teasing my rectum with a fingertip.

"Kayla, baby, do you want my ass?" I asked her, half afraid she would say yes.

"I do, but not yet. We'll assfuck soon, darling, but not tonight. It means everything to me, though, that you offered," she cooed in my ear as she resumed sucking my big penis. I held her head gently, running my fingers in her hair, as she continued up and down on my stiff pole.

While she sucked me, I talked to her softly. "I want you to take my ass, sweetheart. I want you to take everything I have. You own my mouth now, and soon my bottom will be yours, too. And I want your ass as well. I need it. I want you to feel me slide my fat cock deep inside you, and coat your insides with my hot come."

Michaela moaned in response, her mouth still full of dick, the vibrations from the sound adding to my arousal. "I'm gonna come," I finally groaned. She pulled her mouth off of my penis just in time for me to come hard and shoot my load all over her face and hair. She pumped me with her hand until the ejaculations finally ceased and I breathed a loud sigh. "Michaela, I love you," I told her. She gave me a huge smile, and laid her head in my lap, planting soft kisses on the head of my cock.

*********************

After that, we were together often, usually several nights each week. We went out, we stayed in, at her place, at my place. We explored and learned each other's body and mind, with lots of mutual masturbation, oral sex, frottage, snuggling and kissing. We showered and slept together, sometimes bathing in Michaela's claw-footed tub. We went on double dates with Wendy and her homme du moment, privately laughing about our secret that Wendy didn't suspect. I imagined Wendy and Michaela sitting around Wendy's apartment in loungewear, watching TV, drinking wine and talking about their sex lives, all the while with Wendy never suspecting the beautiful penis, often erect, under Michaela's baggy sweatpants. I lavished all the love I had on that penis, and before long it came to be second nature to me. It was, after all, about the woman, not about the genitalia. Orally loving Michaela's delicious organ became, to me, no different than licking and sucking on a vagina and a clitoris. Gently caressing her smooth sack was the same as fingering labia.