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First Time, Since...

Summary:

Two trans women have tentative then increasingly enthusiastic sex. One helps the other learn to feel good with and about her (small) cock.

Notes:

(See the end of the work for notes.)

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“Sorry it’s a little small. And... messy,” Beth said, gesturing vaguely around her studio apartment.

“That’s fine...” Amelia said, standing by the door and fidgeting with her skirt.

“C’mon in, have a seat. You want a cider or something? Or a glass of water?”

“N-no thanks,” Amelia said, moving with tentative steps to sit on the very corner of Beth’s bed—the only place to sit other than the office chair in front of the desk, which currently had a pile of books on it.

“A’ight, well, make yourself comfortable,” Beth said with an easy smile. “I’ll just be one sec.”

She disappeared into the bathroom. Amelia took a deep breath, then another, then another, trying to steady her heartbeat. Beth seems so at ease, she thought, somewhere between glum, envious, and impressed. I bet she does this all the time...

Beth returned, and Amelia had to suppress an “Eep!” of surprise, both because she was a naturally jumpy person, and because Beth had ditched her blouse and jeans and was now wearing only a camisole and a pair of bike shorts she must have been wearing as an undergarment. Amelia swallowed and fought to keep her gaze from inspecting the slight bulge in the front of those form-fitting shorts, but found Beth’s torso to be equally distracting. She wasn’t wearing a bra under her camisole, and her small breasts visibly dented the fabric, while her lean, athletic arms and shoulders were fascinating in their own way.

How does she do that, Amelia wondered. How does she manage to be a little boyish without just seeming like a boy?

Giving one of her easy, confident smiles, Beth came over to stand in front of Amelia. “So,” she said, with a casual note of suggestion in her voice.

“Y-y-yeah,” Amelia stammered. She hugged her slender shoulders to stop herself from shivering, though it wasn’t cold at all.

“Hey,” Beth said, concern surfacing in her voice. “Are you alright?”

“I’m just... n-nervous,” Amelia said. Then, while looking at the ground, “It’s, um, my... first time, um... I mean, not my... I’m not a virgin, but it’s my first time...”

“With someone you met online? Or—with another trans woman?”

Amelia shook her head slightly. “Well—yes to both, actually,” she admitted. “But I really meant my first time... since...”

“...Since your egg cracked?”

Amelia nodded, blushing. “Yeah. It’s been... a couple years for me, actually.” Then, after a moment, she muttered, “S-sorry,” still looking down. “I should have said something sooner...”

Beth sat down next to Amelia on the bed, resting a hand gently on the smaller girl’s shoulder. “That’s okay. It doesn’t bother me. I’m glad you told me, but only because I don’t wanna pressure you. We can just cuddle, if you want. Or make out with our clothes on. Or we can just hang out for a bit. Whatever you’re comfortable with.”

An even deeper blush spread over Amelia’s delicate features. “I... think... I’d like to do more...” she murmured bashfully.

Beth grinned. “Alright. But let me know if you want to stop, or dial it back, okay?” Her hand came up to Amelia’s chin, gently raising the other girl’s gaze to her own. “You’ve already secured a second date, so you don’t need to push yourself.”

Amelia just nodded, still red-cheeked.

“Okay, then,” Beth said, still grinning. “Can I kiss you?”

Amelia nodded again.

She was trembling a little when Beth took her by the shoulders—holding her gently, like she was something delicate and precious—and leaned in to bring their lips together.

Oh, Amelia thought. Oh. Oh!

It had been so long since she’d been kissed. And, in fact, the last time she kissed anybody, she’d still thought she was a man and had to take control ‘like a man’—even though she was terrible at it.

This was different. She shuddered, and surrendered. Her lips parted. Sensuous heat entered her mouth. The crisp, sour taste of the cider Beth had been drinking at the bar danced on Amelia’s tongue. Beth’s scent filled her nostrils. Beth’s hands gripped her shoulders. So many sensations, made unfamiliar both by her long abstinence and her new sense of herself. Her arousal—held in check by nervousness until now—felt different in her body, a kind of buzz through every limb. She felt more sensitive than she’d ever been. She gasped and sighed as Beth’s lips moved down, kissing just under her chin, affixing to her neck, licking her, sucking at her, while Beth’s hands ran up and down her torso.

They fell back onto the bed as if it were the most natural thing in the world. Amelia taking shuddering breaths as Beth’s hands slipped under her cardigan and tunic and slid along the bare skin of her waist.

“This okay?” Beth asked, stopping her hands from going further.

Amelia nodded; then, as if worried there could be some mistake, murmured “Don’t stop!” in such a cute, needy voice that Beth’s lips curved in an almost devious grin. Amelia’s voice cracked in a moan as Beth’s lips found the sensitive skin just below her ear and behind her jaw, while Beth’s fingers ran up her chest and began to circle gently around her nipples.

“May I?” Beth asked, pulling her lips from Amelia’s skin and gesturing with her arms—pulling upward on the hem of Amelia’s tunic, which had already ridden up as Beth explored her chest.

Biting her lip, Amelia nodded, raising her arms and letting Beth pull her top over her head. Then she blushed and covered her bare chest with her arms as Beth looked down at her.

“Th-they’re not... really...” Amelia muttered.

“Let me see?”

A little reluctantly, Amelia lowered her arms to show her (in her mind) somewhat bony torso and the barest beginnings of breasts.

Fuck,” Beth breathed. “You’re so fucking pretty...”

“I am?” Amelia’s eyes widened with genuine surprise. “But—”

“Look, I get boob envy too, but they’re starting to grow on you. Give it time. But god, fuck, whoa... You’re just... This is gonna sound creepy, but you’re like this beautiful little doll. I’d kill to have a collarbone half that pretty! Instead of just...”

She shrugged and unceremoniously pulled her camisole over her head, revealing her bare torso. It’s true that it had neither slender elegance nor feminine curvature, really. A square body, naturally a little heavier and more muscular than Amelia’s. But Beth’s breasts, while still A-cups, where visibly and obviously breasts. And Amelia found that athletic frame to be very attractive in it’s own way.

“Um...” Amelia murmured shyly. “I... like your body too...”

“Glad somebody does,” Beth said wryly, but she seemed more amused than bothered. She lay down next to Amelia, wrapping her arms around the smaller girl, who shuddered, gooseflesh raising wherever Beth’s hands roamed. Up they went, and down, pulling Amelia onto her side and reaching back to run down the small of her back, or over the gentle curve of her butt, or along her hip to finger the side zipper of her skirt.

Beth raised her eyebrows. Amelia bit her lip and nodded. Down went the zipper. Amelia wriggled out of her skirt and tossed it aside, so that they were both down to just their underwear, then let Beth pull her back into an embrace.

As soon as Amelia felt it against her now bare thigh, her heart began to thump. Beth’s cock. Hard against her, held back only by the thin polyester of Beth’s bike shorts. Almost involuntarily, Amelia pressed back into it, rubbing herself against it. Beth gave a little “Mmm” of a moan and her cock twitched. Her erect cock, Amelia noted. Maybe not fully erect, but stiff, and hot. Stiffer than mine gets at all, Amelia remarked inwardly, a confused surge of feelings hitting her. Arousal. Envy. A little of that old inadequacy. A desperate plea—no, no, no, I’m a girl, it doesn’t matter! Anxiety. God, I hope she doesn’t think I’m not into it if I don’t...

W-well, maybe it won’t come up. Maybe we can focus on her.

Amelia’s hand slid down Beth’s side, came to rest on her hip, tentatively slid forward, one finger slipping under the band of Beth’s shorts. Then she hesitated.

“M-m-may I?” she stammered, her heart threatening to leap out of her throat. (Wow, she thought almost dizzily. I want her cock so bad...)

“Yes,” Beth said, shifting her hips slightly to give Amelia better access. “I like having my cock played with,” she whispered in Amelia’s ear, then began to suck on that little spot of skin just behind Amelia’s jaw.

They both gasped in unison as Amelia’s hand slipped past the little bit of cloth and her fingers wrapped around Beth’s cock. Beth a girlish sigh of pleasure, Amelia a little gasp of surprise. Beth hadn’t been fully hard, Amelia thought. But now she is. Amelia felt Beth’s foreskin retreat fully as she grasped gently at the pulsing, unyielding flesh.

She ran her fingers up and down, but the angle was a little odd and Beth’s shorts were tight. With an impatient sound, Beth reached down and yanked her shorts off completely, her cock springing free as she kicked her last garment off her feet. Amelia’s hand was already resuming its exploration, fingers wrapping around, sliding up and down Beth’s length.

With Beth naked next to her and that rigid member in her hand, Amelia felt arousal pulsing in her gut almost more powerfully that she ever had. Within her panties, her own cock even stirred.

A little.

Not much.

Oh god, she thought, her heart rate rising even more, pounding painfully in her chest. Beth’s hand was on her thigh, drifting upwards. She’s gonna... But I’m...

“Do you like being touched down here?” Beth asked, her voice rich with desire, but firm enough that it obviously wasn’t a rhetorical question.

I... I...

Amelia opened and closed her mouth but words didn’t seem to come.

Beth’s hand began to recede. “That’s fine,” she said, her tone a little less husky with sex. “Whatever you—”

She stopped when Amelia’s hands closed over hers, holding it in place on her thigh, just below her panties.

“I...,” Amelia managed, tears pricking the corners of her eyes. “I...” How do I explain it? I do want to be touched. I’m aching for it! And even more than that, I want to be naked with you. I want you to see me. I don’t want to be hiding behind anything. And I want you to fuck me. Oh god, I want it so bad, I want you to hold me down and force my legs apart and delve deep into me! But...

“I,” she whispered, so quietly that Beth had to lead her ear down to hear. “I don’t really... get hard...”

“Oh, I don’t care about that,” Beth said immediately. Then, seeing the confusion and anguish still on Amelia’s face, she twisted herself so that she was on top of her, thighs between Amelia’s legs, cock pressed against Amelia’s belly, so they could be face-to-face. Propped up on her elbows, she pressed Amelia’s cheeks between her palms and looked down into her teary eyes. “Listen. Amelia. I don’t care what’s between your legs. I don’t care if you want to be touched there, or how you want to be touched there, or what you want me to call it, or whether you get hard or not, or anything like that. I don’t mind at all. You can keep your panties on the whole time, if you want. I just want to do what feels good for you. Okay?”

“Oh...” Amelia whimpered. Then, tears coming in full now, “Oh thank god.”

She reached down, grasped the band of her panties, yanked. Giggles as the two of them shifted to let her pull them off. “B-before,” she stammered as she did so, “when I tried to have sex, you know, before... I was too nervous, I couldn’t really... I couldn’t stay hard...”

“Mmm.” Beth just made a sympathetic sound.

“I was so... ashamed! I thought there was something wrong with me. And... I thought ‘how nice it would be, to be a woman, and not have to...’”

“‘Get it up,’” Beth suggested. “‘Perform?’”

“Yeah,” Amelia said, tossing her underwear off the bed and pulling Beth back on top of her—this time, deliberately forcing their pelvises together, so Beth’s cock (now only half hard) fell against her own small, totally flaccid one. She gasped slightly as they came together. “I,” she breathed, “do like being touched down there... But can you just, um... can you just kind of rub, or fondle, or stroke, but not, like, try to...?”

“I think I get it,” Beth said, smiling down at her. She shifted her hips, rubbing her own cock up and down. “Does that feel good?”

“...Yes...” Amelia whimpered, tears still occasionally leaking from her eyes. Beth’s cock against her most private, most sensitive place... Hardening, rubbing its full length against her. The warmth. The intimacy of touching and being touched down there. She couldn’t describe it, so she just said “Yes” again. “Oh, yes.”

“Is there, um... language you’d like me to use? Or not use?”

“Oh,” Amelia murmured, “you can just call it my cock... I mean, that’s what it is... I think it’s nice if you, um, kind of... think about it like a clit? Something sensitive you touch gently? But... I don’t really care about the words.”

“Okay,” Beth said, grinning and continuing to rub her now fully erect cock against Amelia’s still soft one. “I can do that.”

She leaned down so that their chests pressed together and kissed Amelia—deeply, while they continued to grind together. Amelia moaned prettily through the kiss.

“This feels so nice,” she sighed as their lips parted.

“Never done this before?” Beth asked, flexing her cock between them to make Amelia gasp.

“N-no...” Amelia said. “It’s... I don’t know... Even though you’re touching my cock, somehow... being small and soft, and having someone else rub their hard cock down there... The comparison, I guess? It makes me feel really girly? O-oh, n-n-not that you’re not girly, I don’t mean to... I—I still think you can be girly even with big, a hard cock! I think it’s really hot!”

“That’s good,” Beth said, pressing harder. She leaned forward to nibble Amelia’s earlobe before whispering right in her ear. “I think girls with soft little cocks are sooo cute...”

“R-r-really?” Amelia stammered, finding herself tearing up again. “You... like it?”

“Yup. I like to lick and fondle and tease them.” (A whimper from Amelia.) “And I like to fuck them and watch their cute little cocks bounce.”

“Oh god. Oh god yes please yes!


Amelia gave a strangled little moan as a second finger, slick with lube, entered her. She was blushing bright scarlet from her compromising position: on her back, legs spread, hips rolled back slightly to give easy access to her asshole, her little cock flopped against her belly. She heaved shuddering breaths, trying to relax as Beth gently finger-fucked her.

“This ain’t your first rodeo with stuff up your butt, I take it,” Beth said, grinning.

Amelia shook her head. “I-I-I, um... I... use a dildo... Oh, oh god, please, Beth, I want it so bad...”

“Just a minute,” Beth said, continuing to work her fingers in and out while she stroked her erection with her other hand. “I’m no porn star but I’m not small. We gotta do this properly! Though...” She leaned forward slightly and spoke in a softer tone. “If you want to tell me more about how bad you want my cock in your ass, feel free.”

Amelia gave an embarrassed, horny little whine—turned to a gasp as Beth’s fingers sank all the way to the knuckle of the palm, turned to a moan as Beth drew her fingers slowly out, turned to another little gasp as Amelia felt the coolness of a little more lube, turned to a long, breathy sigh as three fingers now slid slowly into her.

When all three fingers had vanished to all but a centimeter, Amelia looked right at Beth, bit her lower lip, and gave another needy whine.

“Alright,” Beth said, grinning. She reached for a condom she’d laid on the bed nearby.

This is where my erections would totally fail, Amelia thought, remembering her laughable attempts at sex as a man, years ago. Beth pulled out the little bit of latex, pinched the end to prevent a bubble from forming, and slipped it onto the head of her cock, and rolled it down with practiced ease. Wow, Amelia thought. She felt a little twinge of envy, then a kind of warm relief as she realized she didn’t have to be able to do it.

She didn’t have to get it up at all.

She was going to lie on her back, spread her legs, and get fucked like the subby little girl she was.

It’s silly, some distant, rational facet of her mind intoned while the rest of her was blushing and panting with anticipation. There’s actually nothing girly about lying back and getting fucked. A man can lie back and get pegged by a woman, after all.

But—(she gasped again as the head of Beth’s cock, cold with lube, pressed against her little rosebud)—it still felt girly.

Pressure. The head of Beth’s cock wasn’t as narrow as her fingertips, of course. Amelia’s cheeks burned, more with desire and anticipation than embarrassment. She whimpered, biting her lip again.

“Ready?” Beth asked, sounding a little breathless herself.

Amelia nodded.

Then let loose a loud, uncontrolled moan as half of Beth’s cock slid into her in one smooth stroke.

Amelia felt goosebumps rise all over her body, her hair standing on end, a tingle running through her limbs. It hurt a little, but it was also incredible. Feeling stretched, feeling full, feeling that warmth down there (so different from a dildo!), and, above all, now the force and friction as Beth, leaning over her, began to slowly work her way deeper with firm, measured strokes.

Who’s that moaning, Amelia thought stupidly. Who’s that with such a desperate, horny, girly voice?

Oh. It’s me.

She gave a deeper gasp as Beth slid in, nearly hilting herself. “You okay?” Beth asked, now panting with exertion and desire.

“Mmmmm,” Amelia moaned, struggling to find words, until she managed to force out, “Harder!”

“Oh! Oh! Oh! Oh fuck yes yes yes! More! Fuck me har—Oh! Oh! Yes, oh yes, yes yes yes, fuck me, wreck me with—oh god—with yo—oh!—fucking cock! Oh fu-u-u-uck ye-e-e-esss!”

Who’s that begging, Amelia thought stupidly. Who’s that wanton slut begging to get fucked senseless?

Oh. It’s me.

Looking down at herself, Amelia saw with giddy pleasure the way Beth’s cock emerged almost fully and then vanished down into her with each stroke. Saw the way her own little cock bounced against her belly with the impact—just as Beth said it would. (It is pretty hot, Amelia admitted internally, proud of her cute little cock for perhaps the first time.)

Fuuuck,” Beth moaned. “Your fucking ass feels so good. You sure—,” her words came heavily, punctuated with deep, pounding strokes, “—this is—your first—time doing this? You seem—like quite—the anal—princess—to me!”

Amelia gasped. She’d been fully prepared to be called an anal whore and to love it, but ‘princess’ took her by surprise. She would have flushed bright red if her face wasn’t already scarlet.

“You like that hmm?” Beth asked, leaning down, pressed her body to Amelia’s and stealing a long, sloppy kiss. (Her hips kept rolling, sliding her length in and out of Amelia’s stretched and willing hole.) “You like being my pretty little princess?”

“Yeeeaaaooooh!” Amelia’s response was swallowed into a long moan as Beth gripped her by the shoulder and pounded her even harder, Amelia’s smaller body bouncing up out of the mattress only to be slammed down again as their hips collided.

“Fuck, I can’t hold it,” Beth groaned. “Fuck! Princess, I’m gonna—I’m gonna come!”

The thought of Beth shooting off inside her, even into a condom, made Amelia’s whole body buzz. But Beth pulled out, leaving Amelia feeling dazed and empty, watching almost without understanding as Beth, kneeling in front of her, yanked off the condom, jacked herself off briefly, then—

Then Amelia was reflexively moaning as Beth’s hot cum landed in spurts on her cock, her belly, her chest. This, too, made her feel girly, though it certainly wasn’t intrinsically feminine to have cum all over you. Her bright, lusty moan lowered to a soft, sensual one as Beth leaned in, pressing her cock to Amelia’s. Amelia could feel Beth still throbbing slightly, cum dribbling down from the head of her cock, running onto Amelia’s smaller, limp one.

Except, not totally limp. The feeling of their crotches pressed together, the warm slickness of Beth’s cum, the gentle aftershock pulses of her climax, all combined with the thorough fucking she’d just been given was giving Amelia the closest thing to an erection she’d had all night.

Beth could feel it. Of course she could, she was rubbing her cock against it. But she’s taking no notice of it, probably, Amelia thought, with a rush of appreciation.

She found herself reaching her own hand down. Grasping her and Beth’s cocks together, stroking them together. (Even softening after her orgasm, Beth was still a little bigger and harder than Amelia.) They sighed in unison at the pressure between them, then giggled a little.

“I’m, um, gonna... try...” Amelia murmured shyly, slipping her hand around just her own cock now.

“What would you like me to do?” Beth asked softly.

“Um... Can you... can you just stay there? I want to...” The flush in Amelia’s cheeks, which had faded somewhat, came back in full. “I want to feel you there, when I come.”

Beth grinned down at her. “I can do that.”

It was surprisingly easy. She was aroused. She’d been aroused since Beth had first kissed her. Her cock was sensitive and eager for attention, and it had been a while since she last came. Beth’s cock resting against her hand as she stroked herself didn’t hurt. Nor did Beth reaching a finger down to gently rub the rim of Amelia’s asshole.

So, even though she still didn’t become fully hard, she came in a minute or two, emitting a high panting sound that suddenly dropped to a low, shuddering sigh as she ejaculated. She pulled her hand away and just let Beth gently rub their cocks together, savoring the warmth as little pulses ran through her. Her cum was thicker and whiter than Beth’s but only spurted twice onto her belly, the rest just oozing out and commingling with Beth’s between their cocks.

Beth sighed. “That was hot to watch,” she commented.

“R-really?”

“Yeah.” Beth flexed her cock, causing Amelia to intake breath sharply. “You don’t feel how I’m almost hard again?”

“Oh... wow...”

“Just ‘almost,’ though, I think,” Beth said with a half smile. She leaned down, bringing their chests together and their faces close.

“W-well,” Amelia stammered. “I think it’s pretty impressive that you... oh, how do I put it? I don’t want to be... weird about it. But even before HRT I couldn’t really stay hard for sex. So I think you’re... impressive.”

Weeell,” Beth said, drawing out the syllable as she leaned in for a brief kiss. “I may have taken a Viagra before we left the bar.”

“...Oh!” It took Amelia a moment to process this. “Really?”

“Yeah,” Beth gave a smile that might have been sly and might have been sheepish. “I mean, HRT fucks with my dick too, and I was pretty into you and I knew how I wanted tonight to end, so I thought I might as well, uh, dress for success, I guess? In case I got lucky? Hope you don’t mind.”

“Um... Mind... Right... Uh, no, I don’t mind. No. I don’t mind at all.”

Beth laughed and kissed her again. A longer kiss this time. Little “Mmh” sounds as they settled into it. Amelia brought her legs up to wrap around the waist of her lover—something she’d always wanted to do—and their cocks continued to slide against one another in the middle. “I really, really don’t mind,” she breathed into Beth’s lips.

“S-seriously, Beth,” Amelia whispered, as the kiss faded to nuzzling. “That was easily the best sex I’ve ever had. Oh! I probably shouldn’t say that. I know it’s only our first date, I don’t mean to...”

“I’m glad you liked it,” Beth remarked, “but I don’t think I can take full credit. You said this was your first time since transitioning, right? I think sex as a woman just... suits you.”

“M-m-maybe,” Amelia stammered, blushing prettily for about the hundredth time that evening.

“Still,” Beth murmured. “I guess we’ve set a pretty high bar for date number two? How am I gonna top this... Hmm...” She leaned in, kissing just below Amelia’s ear to make her squirm before whispering, “I’ve got a few toys in the closet we could try... Ever used anal beads, my little anal princess?”

Blushing even redder, Amelia shook her head.

“Wanna try?”

Redder still, Amelia nodded.

Notes:

I wrote this one quite quickly, so I feel like it's a little rough around the edges, but I'm trying to be more comfortable with just putting stuff out there rather than letting it sit on my hard drive, 95% done but not perfect. I figure we're all friends here, and y'all probably don't mind the occasional awkward turn of phrase nearly as much as I do.

(Also, it's not like my other stuff is perfect even with my obsessive editing, hahhh...)