Reliving Her First Time (F/transgender)

Story by Wilczyca on SoFurry

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#1 of Christie


Not many people own a dildo as medical equipment.

Now, I know what you're thinking. ("But doctor, what are you doing?" asked Nurse Yiffem as he took out his equipment. "We need 12 inches, stat!" Dr. Studly replied.") But this is not that type of story, nor for that matter is Christie that kind of person.

No, Christie's dildo was every bit necessary and legitimate. She had had her sex change only six months ago, and her dildo was part of the recovery. Several times a day, Christie slipped away to the privacy of her room to lay back in her bed and hold one of the dildos in her pussy for awhile. This was not an unpleasant ritual, and she kept to it religiously. This was her second time that day, and she wasn't any less eager than the first. But here we've wasted too much time on description already. We're missing the event.

Christie lay on her back on the sheet; her legs, relaxed, were spread out. Take a moment to admire her while she's staying fairly still. It was a warm summer's day, and she felt absolutely no need to keep her clothes on. While she has never been athletic, she keeps fairly slim and from this angle her stomach is soft but flat, and framed quite nicely with her surprisingly wide hips. Her breasts complete the picture, two beautiful, round breastsâ€"quite largeâ€"that many women might be jealous of. In fact, there is little to show that she's transgenderâ€"no stereotypical trace of masculinityâ€"except for the two very light scars that trace a short path down her labia. And what soft lips they are, very tender and shy, and still hiding her pussy itself for now. It was still so new to her that its shape was still something of a mystery to her.

She did not wait for our probing eyes. By now she had the first of her dildos, the thinnest, ready. It was a long, plain white cylinder, only thinning at its very end where it reached a pointâ€"just now slick with the lube she had slathered it in. She took it by the other end and held the tip to her pussy, then pushed until it was inside her as fully as it could be.

She laid her head back on the pillow with a sigh. Her "new" body was still such a novelty to her; however small the dildo was, the fact that she could penetrate herself like thatâ€"the fact that she had a pussy to penetrateâ€"felt something wonderful to her. She closed her eyes and let herself relax. At that moment, so completely unselfconscious, she was perhaps the most beautiful she has ever been. In public, her body was covered by clothing, and she had never learned to dress to accentuate it; her face, unadorned with makeup, couldn't meet the standards of augmented femininity; and her poise was always shy and unready, never confident. But here, she was in a perfect state of raw femininity, and it was here that, without trying, she was at her most attractive.

Before long she pulled the first out, and tossed it onto a towel to clean for later. Soon she had the second dildo lubed up. It was thicker than the last one, almost thicker than she was used to. As its tip pushed aside her lips, and she pressed it into her pussy, she felt something much stronger this time. She was still so inexperienced that every little feeling seemed magnified a thousand times; even a small pleasure could overwhelm her, and she was finding it hard to think of anything else. With her head laid on the pillow again, she let herself begin to be absorbed by fantasies.

Here, of course, she was entering virgin territory. She had only actually had sex once before, and that was years ago back before she graduatedâ€"back before she had started transitioning. That was with Stephanie. God, she hadn't thought about Steph in ages.

It had been a bit awkward. Now most first times are, but hers was especially short and unsatisfying. She liked women, she knew that, but even then she had known that she was a woman herself. She hadn't felt that she knew how to play the man's role, and she had been right; it had taken a long time for her to get it up, only to shoot out her nervousness prematurely a few minutes later. It was the only time they had ever had sex.

She wondered what it would feel like now, especially whenâ€"mmm, that felt good, she thought as she penetrated herself with the third, largest dildo. She wondered what this would feel like with another womanâ€"filling her with her fingers, maybe, softer and warmer than the dildo could be. But she decided she was getting ahead of herself. Why not start from the beginning?

She would start with a kiss, laying a hand on Steph's shoulder to pull her close. Her other hand would trace down her side, running into her waist, down her hip. She might kiss down her cheek, nipping at her neck; Steph would gasp, that little squeaking sound Christie remembered she made when she surprised her.

As Christie nudged her a little closer to the bed, Steph had already moved her hands down to Christie's pants. She fumbled for a second, but soon undid them and began to pull them down her legs. Her hands reached just inside the waist of Christie's pants, and her panties; as they fell lower, her fingers grazed her lips and her clitoral hood. Steph kissed her as Christie quivered; the new feelings still overwhelmed her each time. Steph smiled and took ready advantage of it, nudging her onto the bed.

As Christie sat up on the bed with her legs spread out, Steph crawled over her; she kneeled with her legs on either side of Christie's. They closed their eyes as they kissed; Steph's left hand slipped into her shirt, exploring until it rested at her breast. Her palm spread over its soft surface, and her fingers lightly massaged all around where they could reach.

"Anh..." Christie broke out of the kiss with a soft moan. Steph took the chance to take off Christie's shirt, following with her bra not long after. While her hand cupped Christie's breast, she didn't stay there long; kissing and nuzzling experimentally, she made her way down Christie's body. She kissed at the top of her pussy (Christie gave an appreciative shiver), then licked down until her lips settled by her clitoral hood. Her clit was already attentive, but Steph could feel it perk up under her lips when they kissed her hood.

As Steph's tongue explored her clit, the fingers of her right hand slowly teased just at the inside of her thighs; they just barely grazed her lips. Christie couldn't help but shiver; Steph laughed to herself at just how oversensitive she still was, though she was sure Christie wouldn't get the joke. She pressed her tongue down on the hood of her clit, making her squirm again. She massaged left and right, while slowly moving down until she reached the hood's tip. Finally, when the very point of her tongue touched on the clit's exposed fleshâ€"

"Oh! Ah-hh..." Christie moaned, this time very, very loud. She turned bright red in her embarrassment; she was sure that everything down to her pussy must be painted red, her embarrassment radiated so much. If you held a thermometer three feet above her, it would burst.

But as she looked down, she saw how much Steph was smiling even as her tongue pushed, nudged against her clit. Breathing out, she relaxed againâ€"and it was easy to relax when she was being eaten out. It wasn't long until she was shivering again. Steph decided it was time to change a little. She pulled back her right hand and slid her fingers into her mouth, sucking on them for a moment. A moment later Christie felt them graze her pussy lips, start to push in.

Her eyes were clenched shut and her wrist was tingling as she could nearly feel those fingers in her. Almost without meaning to, she pulled the dildo back until it was nearly out of her, then pushed it back in as deeply as she could. Every muscle in her body seemed to tense as she started pumping it regularly; just slowly at first, but speeding up before too long.

After a few minutes, Steph pulled her head back again. With her fingers still in Christie's pussy, she slid up her body until she was lying to her side. Her breast rubbed against Christie's as she settled in. As she started to move her fingers again, she curled her palm over Christie's pussy so that with each push her palm rubbed, massaged her clit. She cut off the beginning of a moan as she kissed Christie.

The kiss was what did it. As the dildo plunged deep in her pussy, Christie felt her pussy begin to squeeze around it when she started to come. Her whole body tensedâ€"she felt as though her every muscle was throbbing like her pussy, and her clit. As her wrist skittered it was all she could do to keep moving the dildo, keep thrusting it in herself, keep the orgasm pumping and coursing until she was sure that she couldn't move any more.

Her body slumped exhausted, and happy; her head lay buried deeply in the pillow. With her eyes closed, she could feel the the orgasm and the kiss both linger until she could hardly tell which had been the fantasy and which was the reality.