April 10, 2015

Friday Free Read: A First Time For Everything

 If you've been following me a while, you may have heard me say here or there that I'd like to try my hand at writing a story about a transgender character's experience. I hesitated on this for a long time because I wanted it to be the right story: one written because the character was there, and had something to say. She finally came to me in the form of Rachel, a gal experiencing intimacy for the first time, with a new partner, after transitioning from male to female.

I can't promise that I've got everything "right" here. My intention was to stretch myself into a new perspective, a new individual's experience. I researched quite a few aspects of the story, including the process of transitioning, real-life coming out experiences of transgender individuals, transgender lesbians, and so on. I hope that what I've written is written well, and honors the character and her real-life counterparts. If I've gotten anything wrong, I apologize ahead of time. For now, I hope you enjoy.



Hands, like the slow, sensual touch of a candle's glow, sliding down my sides. Her fingers touched me, shaping me, smoothing me like sculptor's clay. My sigh sounded loud and hot in the dim light and the thick, billowing steam, as the lilting dance of Spanish guitar guided her over my body. She danced with me, her slight, slender frame pressing to me, arching with me, inviting me to move with her like mermaids gliding through the water.

I hardly realized it as I murmured her name. Tassy, Tassy, baby, as her gentle palms explored. They roamed upward, sliding over the damp white nylon of my swim halter, and a light, shivering sensation of pleasure blushed along the breasts beneath. The nipples peaked underneath, oh, I'd warned her they were sensitive...I'd warned her.

Tassy's thumbs rolled over them and I bit my lip on a gasp. At the same time—sidling close to me, sliding between my knees where I sat on the lip of the bath—her lips found my neck. She kissed a line from the dip of my throat up to the place just below my ear. Despite myself, I tightened my legs against her; my own hands slid around to the back of her neck.

"Are you ready, Rachel?" she whispered to me. I wasn't sure. I didn't know yet. Even though her sweet, seductive motions thrilled me in ways I'd never expected, I uttered a denial.

"I'm sorry—" I said in a tiny voice. "No, not yet."

"It's okay," she replied. "Take as long as you want. Just tell me what you need."

I needed her. I wanted her, anyway. But I shook, too, and not just because of how Tassy made me feel.

Her short, short blonde hair spiked up a bit, wet from the Jacuzzi. Tassy wasn't butch but she was a tomboy, and when she'd come out from behind the changing screen she'd set up for us, the sight of her in a slick, feminine navy two-piece struck me dumb. She hadn't hesitated to wade right in; I, on the other hand, couldn't quite bring myself to come off the edge. We'd talked about how to approach this step in our budding relationship—the sex step. A ticklish subject...especially for me. She'd suggested a hotel room for the night, maybe to give us both a sort of neutral ground. Start with a hot bath, yes. Light candles. Play some of our favorite music.

I wanted this. I wanted her, for sure. I really, really wanted this to work.

"Breasts okay?" she asked. I nodded. Breasts, I could handle.

She ran her hands over them again, gently, even though the slightest touch made them ache and yearn. "Can I take off your top?"

That brought a flutter of self-conscious apprehension. Only my doctor had seen my breasts. They'd yet to make their debut to anyone else but me, when I looked myself over in the mirror. An unwelcome and irrational certainty rose up, that Tassy would be able to pick out something different about mine. They wouldn't be like the breasts she'd caressed and kissed on other girls. She'd be able to tell.

"I don't have to, if you don't want me to," she whispered in my ear.

"No," I whispered back. "Go ahead."

I had to dive in sometime.

Tassy was the first person I'd come out to. The first real person, the first one who counted, who wasn't my therapist, my doctor, or my family. I'd been afraid to. Still afraid now, as we carefully worked at taking this next step together. She wasn't just the first person I'd come out to...she was the first person I'd dated. First woman I would ever make love to.

I wasn't a virgin. I had a short history of spectacularly disappointing, even upsetting attempts at sex, in college, before I started my transition. In my mind they were like a series of hurdles, and I the racehorse being made to jump them. I'd made it far enough to say I'd done it, but it hadn't been anything close to right for me. Dating had been like that, too, even in high school. A lot of awkward social outings I didn't know how to navigate. My mother thought it was shyness. My father wondered—often and loudly—if I might be gay. As if the only reason I didn't have a line of girls jumping into bed was because I didn't like girls. I liked girls, girls weren't the problem.  I was the problem.

 Well...Nick was the problem.

Tassy moved her hands underneath my swimming halter, and her warm palms, wet from the hot bath, spread over my breasts. The hormone-assisted breast fairy had given me tits susceptible to soreness and throbbing, especially when aroused. It didn't hurt, really—actually, I sort of liked it, because they were my breasts. My breasts, Rachel's breasts, were a little more sensitive than the average gal's. But it could be instense. Tassy didn't take off the halter yet, and maybe she sensed how much I needed her to go slow.

I thought she should go slow too, though. Tassy didn't know much more about this than I did, after all. She'd never been with a transgender woman before, she told me so herself when I came out to her. A little less than four years into my transition left me feeling happy with my body, happy with Rachel. But I'd never taken what some people consider "the final step": I hadn't had the surgery. I didn't even know if I wanted surgery.

And right now, as Tassy kissed me, as her hands gently caressed my nipples under wet nylon, I couldn't help but be wildly aware of the rigid erection straining underneath my swim shorts.

I'd known this would happen, of course. I knew Tassy knew it, too, but still it made me anxious. I tried to turn, twist my body, tuck myself away so that it wouldn't be noticeable, but all she had to do was look down and she'd see the shape of my dick under white shorts.

Then what would happen?

"I'll be fine," she'd told me earlier. "It's not like I don't know what a penis is."

She'd also said other things, though, and those were the things I worried about now. I'm gay, she'd said. I've only ever been with other girls, only ever wanted to be with other girls. I'm...just not sure how I'm going to feel about bringing a cock into the mix.

If we'd been discussing anyone else, any other couple's situation, I might have laughed. She'd said it to make me laugh, surely...she liked to be the funny one, to make other people smile or snicker at something naughty. My cock was the cock in question, though, and my decision not to have it surgically altered into the vagina she might prefer. I could picture her, amid all this caressing, all this sensual touching and sweet whispering, then coming to my shorts and the stiff organ underneath them. I imagined her freezing in place, faced with my jutting erection, screwing up her nose and calling the whole thing off.

"Rachel," she murmured in my ear, pulling me abruptly out of my thoughts. "Relax. I'm feeling good, are you?"

"Yes," I whispered. She kissed me, and finally she slid my swim halter up and over my head. Even as she did it, though, she kept her eyes on mine, watching me for a cue, a signal. When I didn't give one, she let her arms fall to my sides and very gently lowered herself to kiss each of my hard, dark nipples.

"Still okay?" she asked. I uttered a soft yes. Her lips pressed to me, warm and delightfully damp, affectionate in their sweetness. Then she wound the tip of her tongue around one hard peak and I moaned; it felt subtly electric, like she might be tracing just the tip of a tiny ice cube around the dark areola. She alternated to my other breast. I started to forget my anxiety and sank into the feeling.

"You have gorgeous tits," she whispered between kisses. "Just tell me if you like this..."

"Oh!" I huffed as she gave a firm suck. "Ah, a little gentler, please?"


She returned her attention to kissing, and as she did she slid her own bikini top off. Her breasts were a soft, creamy color in the glow of the candles, nipples a dusky rose. As she stood up straight again in the water, winding her arms around my waist, she smiled. Her pretty brown eyes, full of warmth, met mine.


I stroked a thumb down her cheek. "You're going to laugh. We've only been dating a few weeks, but this is the first time I've ever been...this close to someone."

"Well, there's a first time for everything," she smiled.

"I really like what we have," I said. "I'd really like to see where it could go."

"I would too."

"I just don't want you to see my cock and..."

"Rachel, I'm not here with a cock," she interrupted. "I'm here with you. I told you I might not be comfortable but we're going to see. We're taking it slowly and we'll just see where it goes, okay?"

"Okay," I said.

"Do you want to try it now?" she asked. "You're really wound up. We can back off now, or we can go for broke. Nothing to it but to do it. What do you think?"

It terrified me. Memories of awful sexual encounters, awkward and clumsy and hollow and disappointing, wanted to creep all over me. Memories of girls looking over my body, the body I felt so wrong in. They never seemed to see anything out of the ordinary, though, and that made me feel even worse, even more alienated. Like I was walking around with a gaping, bleeding scar on my chest and everyone else kept assuring me things were A-okay. Distraction and shame sometimes made it hard to 'perform' as expected. One girl blew up at me and called me a "limp dick" before storming out of my room. She'd been the last one I ever tried to take to bed.

Until now. Now I'd finally taken care of that aching scar, but I thought for sure when Tassy saw me, all of me, she would definitely not think it was A-okay.

"We can get dressed again and just lie in bed, if you like," she said. "But I'm not afraid to try and do this, Rachel honey."

Honey. But more than that...Rachel.

When I told her about my transition, I'd told her my name—before—was Nick. She knew it...but she'd never once called me it. Here was a woman who didn't know Nick from Adam. But she knew Rachel.

"I want to try," I said.

"Then tell me what you'd like," she said. "It's all up to you. And if you change your mind we can still go cuddle, and leave it there."

I didn't answer her in words. I wriggled, a little awkwardly, and hooked my thumbs under my swim shorts. After a last second's hesitation, I drew them off.

My cock stood up between us, perfectly at attention. Tassy regarded it, giving no indication whether it shocked her or bothered her or disgusted her. At least, I didn't see any. She was the first person to see me fully naked, breasts and curves and balls and all. Maybe if I'd had some experience being naked with anyone else, I might have seen a flicker of something in her. I didn't, though. She sunk down a bit until she sat on the hot tub's underwater bench, just between my knees.

I realized she was a little flush in the breasts and cheeks. She asked, "Do you...would you like me to go down on you, honey?"

I blinked, and must have stared for a fraction of a second like an idiot. My cock seemed to know exactly what it wanted, though, because it bobbed—throbbed, really, with an excited need—and I said, "Yes, I'd like that. If it doesn't bother you."

"Well, I've never done it with one of these before." She smiled, her expression still full of good humor. "I'm a career muff diver. Never went looking for pink torpedoes."

She waggled her eyebrows at me. "But like I said...first time for everything."

She made me laugh again, and then we traded smiles. Floating closer in the water, she reached out, and wrapped one slender white hand around my cock.

"Just tell me if you like it."

I closed my eyes, nodding in agreement. For now, I simply wanted to feel her hand around me. Firm, skin-to-skin contact. Those movements again, fluid, dancing, gliding like mermaids together, like we weren't new lovers at all but knew each other's bodies with a natural grace.

She moved her hand slowly up and down my shaft at first. I didn't open my eyes but I imagined she might be watching for me to take the lead. I nudged my hips into her motions, urging her on a little faster, a little faster. Soon, the novel sweetness of her hand on me gave way to a deeper sensation: the swell of pleasure stirring to life all through my loins. I rolled into it, letting my head fall back, groaning softly.

"It's beautiful, Rachel," she whispered. The sound of her voice set me a little more at ease, and I let myself relish the feel of her fingertips kneading, tugging at the tip of it.

"Really," she said. "You really are beautiful."

A bloom of something deeper than pleasure, and entirely unrelated to her hands on my body, welled up in my chest. Before I could say anything, she planted a kiss on the head of my dick, and I shivered.

She'd hesitated. I knew that. But after the first tentative kiss, she tried another one, and slowly worked her way to giving me a long, lavish test with her tongue.

I groaned again, and she whispered, "Is that okay?"

"Yes," I said. "I like it. What about you?"

"I'm going to take my time, is all," she replied. I opened my eyes again. She leaned on my thigh, gazing up at me, while she fondled and carefully stroked my cock with one hand. After a few moments, she climbed to her knees so she could also kiss my breasts again, and I lifted my fingers to stroke her spiky hair.

Her movements soon took on a tandem rhythm. She'd run her tongue in gentle rings around my areola, laving my nipple until she closed her lips on it in a kiss; at the same time her hand would work up and down my cock, massaging it in strokes gaining more and more strength before she'd back down, come nearly to a stop, and let my pleasure cool.



"How you doing, baby?" she asked me.

"It's good, Tassy," I said, and I imagined she could hear the heady relief in my voice. She stretched up to plant a kiss on my collar, then my neck, and finally—I had to tilt my head down to meet her—my lips, and her free hand stroked my face. I moved my hips to her pace, eager for her petting motion, happy for her kisses. The performance anxiety drained away, and—as people sometimes do, in hindsight—I wondered how it had felt so intense in the first place.

The experiences from before intimidated me, yes. Now, though, as Tassy stroked me, kissed me and nuzzled my breasts, and whispered my name—Rachel, honey...Rachel, sweetie, you're beautiful—those old experiences became Nick's experiences, not mine. The awkward disappointments, the distress, the rejections, all lost their claws, and it felt like they'd happened to someone else, someone far away. This was my real first time. Tassy would be my first lover. She'd be the first person to see, to feel, to make love to this body, this whole body.

She came up out of the water just enough to press her torso against mine, my mermaid coming up out of her tide pool. My cock pressed against her soft belly, and our lips came together again and again, breasts crushing sweetly against breasts, her wet form gliding up and then down my naked body.

She came to my cock again, and tenderly nuzzled it. Her kisses came a little more freely, and then she ran her tongue all the way along my shaft. She took me in her mouth, and I shivered and gave a little cry of delight.

Nothing to it but to do it, she'd said. And she was doing it now. Hesitation dissipating, she took me in her mouth, her tongue working in frisky little motions along the crown. She licked me the way I imagined she must lick pussies: kissing, planting soft, slow kisses before circling and thrumming the tip of her tongue, always focusing on the head. I ringed my own thumb and forefinger around the base just to keep a little kneading going along the shaft, but her lips and tongue—and the few brief times she brought her whole mouth down around it—worked a heady, thrilling excitement high in my body. The orgasm I felt, building to a crest, felt ephemeral, almost teasing, climbing just above the tip of the cock she sucked and teased like a clitoris. I feared it might be out of reach, just, just out of reach, flighty and fleeting. Then I thought, when I did come, it would be fast, over and done with too quickly. It scared me. Then, it tipped.

I came in a bright spasm, cum jetting from my cock almost before I knew it—and it sent me up and over, drawing a startled but joyous cry from me. The titillating pleasure spread out and down and through my legs, and sent a wave of bliss up through my chest straight to my head. My nipples tingled, they came alive with sensation, and I pressed my hips even harder to Tassy, wanting more.

She held one hand wrapped around my shaft as I came, the other arm wrapped around my waist, her head resting on my hip. Though I'd thrown my head back again at the first pumping burst of cum, I could tell she was looking up at me, listening to my gasps and groans, very gently stroking me, slowing her rhythm but still holding my cock.

"How was that?" she asked. "I mean...did it feel good, Rachel?"

"Better than good," I panted. I wrapped an arm around her, hugging her closer to my hip.

She smiled. I could hear it in her happy sigh. Soon she tugged me a little closer, and I eased down into the hot tub beside her on the bench. She put her arm around my shoulder and guided my head down onto hers. She kissed my forehead.

"You're beautiful," she said again after several long moments.

"So are you," I replied.

I didn't know if Tassy would turn out to be "the one", as they call it. Or my "soul mate", or whatever other term there was for it. I hadn't been looking for someone to spend the rest of my life with, when I finally got up the courage to come out into the world as Rachel, and start dating, as I'd never been able to before. All I'd wanted was to know if I could do it. To see if I could pass, really pass...and to see if someone else—a partner—could finally see me for me.

She was, really, my first time for everything.





Looking for more LGBT romance?
More F/F titles by Brantwijn Serrah:

A courtesan's love...
A vampire's curse.



Rhiannon gets a delicious surprise
in "Her Dark Rewards",
part of Crimson, Volume 2
Kylie's looking for something different
in "Graveyard Games",
part of Crimson, Volume 1
(link coming soon)
The sweltering heat of summer
won't stop things from getting steamy
in "Heat of the Night",
part of Coming Together Through the Storm


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