Jessica

Author's note: This is mostly vanilla first-date stuff. The story starts out fairly extreme with BDSM, squirting, and fisting that's all SSC (Safe, Sane, and Consensual) but it turned out that her story was much more of a traditional "figuring things out" story of a transwoman, albeit an involuntary one. On that note, I am a cisgender male so if I got any of the details on how this kind of thing works then the blame is with me and I'm sorry. If that's the case and you let me know what I missed the mark on, I'll incorporate it into my future writing.

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I was trembling. I couldn't see anything due to the blindfold over my eyes. I couldn't say anything, either, due to the ball gag buckled firmly around my head. I could try some vowel sounds but that was a best-case scenario. My stomach was full of butterflies like it always gets when I'm in a scene. That and the trembling was due to anticipation and excitement.

In addition to being blindfolded and gagged, my wrists were padlocked in leather cuffs which were tied to the bedposts above my head. My ankles were cuffed in the same way and also tied to the bedposts above my head so that my legs were spread wide and were up over my shoulders, making my ass stick up. There was a pillow underneath to help support it. But I was completely vulnerable.

My firm D-cup breasts were also topped by a pair of clover-style nipple clamps—the kind that if you pull on the chain, they bite harder. The chains for each of my clamps were actually attached to the strap on my gag so that if I moved my head too far, it ended up sending fiery pain to my nipples. I'm not normally one for pain but sometimes I'm in the mood for it and it heightens the pleasure.

That's a lot like me being the sub, too. I'm a true switch. The power exchange of bondage itself is what really turns me on. I'm almost as happy being tied up as I am being the one doing the tying. Yes, I do prefer to be dominant but it's definitely not a strong bias.

Which is why me being in this predicament had my cock pretty hard. Yes, that's right: I've got both breasts and a fully functional, eight-inch-long, thick, uncut penis. It was one of the things that Linda, the woman who had tied me up like this, found attractive about me. But it wasn't just that. I'll admit it, I'm pretty good looking.

I stand at five feet, seven inches tall when I'm barefoot. I've got light brown wavy hair that I keep falling just past my shoulders. I have big hazel eyes, a fairly narrow nose, high cheekbones, full lips (I've heard them called "dick sucking lips" before), and a smooth, clear complexion. I also keep my body completely hairless below my eyes.

I jumped a little as I heard Linda ask softly, "Are you ready, Jess?" My name is Jessica, but it wasn't always. More on that later.

I nodded my head up and down. "Mmm-hmm." She kissed my lips very softly and I moaned slightly. Unlike a lot of male-to-female transgendered women, my voice sounds like I have been a woman for my entire life. I have a clear, feminine voice. When I sing (and I'm pretty good at it), I'm a mezzo-soprano, right between soprano and alto.

Linda's weight shifted as she sat on the bed that I was tied to below me. I wasn't wearing a stitch of clothing but I had seen what she had on before we started and she was stunning. She was wearing a black corset with demi-cups that supported her slightly smaller breasts but left them exposed. Her corset also had garters, which held up matching lace-topped stockings. She was also wearing thigh-high leather boots with a stiletto heel. Even with those boots, though, I was still taller barefoot than she was.

Linda was only five-foot-one. She weighed roughly 110 pounds, had auburn hair that was longer than mine, her breasts were a large C-cup, and her measurements were 34-22-34. She was a little sex kitten who just loved to be a domme and happened to love the idea of tying up a switchy chick with a dick.

I jumped again as she traced her fingernails gently up and down the length of my shaft, sighing as she did. It felt really good. I was already at half-mast and flexed my PC muscles, feeling myself get harder.

Meanwhile, her other fingertips traced gently around my hole, gently probing. She had already lubed me as well as her fingers thoroughly. I sighed as the first of her fingers slid into me. She soon followed it with another, still lightly playing with my cock. Her fingers slipped in and out slowly, gently stretching my hole. She began to curl them upward inside me and I groaned as they brushed against my prostate. I could feel the pre-cum on my belly where the head of my cock rested.

Suddenly, her fingers disappeared from my dick and were replaced by her mouth. I groaned through my gag as she worked a third finger into my ass while her other hand stroked my cock in line with her mouth that sucked and swirled around my head. I was in heaven, the pain in my nipples increasing as I leaned my head back but at the same time heightening the pleasure that Linda was giving me.

I was disappointed when her mouth released me. "Not too much, little girl," she soothed. "I want you to come in a different way."

I gave a little whine that expressed my disappointment but also conveyed that I was resigned to whatever she planned on doing to me.

"You'll love it, I know," she purred, getting her pinkie finger worked inside my ass to join the others. I groaned as she filled and stretched me, still curling her fingers. I was well-practiced at keeping my hole relaxed and just enjoying it, and this was clearly not Linda's first go at ass play. She expertly kept flexing her fingers to continue stretching me while basically fucking me with her hand. It was amazing, and she was right. So far, I was loving it.

I felt myself stretch even further, just as I was getting used to how far she had me stretched, as she began working her thumb into me. This was when she had to slow her hand's entry by a lot but she had me moaning and breathing heavily as she kept fitting more and more of her hand inside.

A few minutes later, I groaned as the knuckles at the base of her fingers slipped inside. I was so full! She had made her hand into a rough pyramid shape to better penetrate me, which felt fantastic as the inner parts of my muscle ring stretched to accommodate her. I was moaning and shaking, since this was actually the first time anybody had tried to fist me.

A moment or two after that, I groaned and felt her hand enter me all the way, so that my asshole was closed around her wrist. She chuckled as I involuntarily clenched my muscles, making me moan even louder, since that just pulled her hand deeper into me. There was a little puddle on my smooth belly where my preseminal fluid was leaking out of my rock-hard cock.

Linda gave me a few minutes to get used to the fullness and then ever so slowly changed the shape of her hand, drawing her fingertips in toward her palm. I groaned and writhed. I could feel every tiny motion that her hand made and it was heavenly. I was ecstatic, totally helpless to resist anything she wanted to do to me.

It was never easy for me to reach orgasm just from being penetrated. It had happened a few times before, and while it was fantastic and I wished that I could have it happen more often, I usually needed to have some form of manipulation while I was being fucked. But nothing prepared me for this. I almost screamed once she had her fingers retracted and she squeezed her fist together. Her forearm muscles thickened, stretching my hole even further, while her fist expanded deep in my bowels. It was one of the most intense feelings of my life.

I could feel an orgasm building and I could tell that it was going to be big. "You love that, don't you, pet?" she asked sweetly. I couldn't even answer. I was just engulfed by the rapture. "I'll bet that this is going to make you cum, isn't it?"

I barely nodded in agreement. I couldn't do anything else, the only thing my mind could hold was feeling her fist pulsing as she slowly flexed it.

Without warning, my toes curled, my thighs tried to squeeze together, my breath caught, and my arms flexed against my bonds, pulling them tight and pulling my body slightly away from Linda. This just seated her flexed fist slightly lower in my bowels, only heightening the orgasm that erupted through my whole body. I screamed and pulled my head back, setting my nipples on fire, as my cock pulsed over and over again. I could feel my cum landing all over my belly, up on my breasts, and even a few streams of jizz landed on my neck and chin.

It was one of the longest orgasms of my life, just going on and on until I collapsed, a panting, sticky mess.

Linda very gingerly withdrew her hand and if my physiology allowed it, I would have come again as her hand stretched me out one last time, then withdrew. Once it was out I missed the feeling of fullness immensely.

"How was that? Did you like coming for me?" she asked.

Between pants, all I could muster was, "MMMMMM!"

I could hear her smiling as she said, "Good. But now it's time to make me come." She got up and untied my ankles, then attached them to the posts on the footboard instead. I was now tied down spread-eagle. My cock had softened a little but I was still pretty hard and my chest was covered in my own jizz.

She unbuckled my gag and dropped it on my chest. I gasped as it tweaked my super-sensitive nipples but she soon covered my mouth with her own, kissing me deeply and in a way that left no doubt as to who was in charge. "Thank you, Mistress!" I panted when we came up for air.

"You can thank me," she replied, kneeling on either side of my head, "by getting me off, now." I could smell her womanly arousal just inches from my face. I dove in with gusto.

I'm attracted to both men and women equally. I have a special place in my heart for other girls like me, and I prefer another t-girl over either men or women, but with my sex drive, I like 'em all.

I adore eating pussy, too. Especially one that's as tasty as Linda's was. She was also completely hairless. I didn't waste any time fiddling around with her labia, as soon as I could find it with my mouth, I went straight for her clit. I sucked on it while the tip of my tongue danced on and around it. Linda groaned and I could feel her lean forward and grab the bedposts. I could just see the look of extreme pleasure on her face, in my mind's eye, as I ate her. "That's right, eat me, you little slut," she panted.

I only had to do that for about a minute before I felt her starting to shake, her breathing becoming irregular. She was going to come, too, and I was a good little girl for getting her off. I redoubled my efforts and she soon clamped her thighs around my head as she screamed. I didn't let up for a second, mercilessly stimulating her clit. My face was covered in her juices and I felt a gush once or twice that made me think that she could squirt if she tried. Which was another thing that I thought was hot.

Shaking, she pulled herself away from my eager mouth. "Good girl, Jessie," she told me between breaths. "It's been a while since anybody made me come that hard."

"You made me come harder than I think I ever have, Mistress," I countered. "Thank you."

"We're not done yet," she told me, placing the ball gag back into my mouth and buckling it again. I grunted as every movement sent little jolts of pain out from my nipples. They were going to be sore tomorrow, I could tell.

Once I was gagged again, she laid down beside me, started stroking me gently, and murmured, "I'm going to ride this beautiful clit of yours, Jessie. You're going to make me come again." All I could do was moan my approval of both the idea and the way her hand moved on me expertly.

I cried out as Linda briefly tweaked the chains going to my nipple clamps, but that just made me harder. I was totally immersed in sub space at this point.

It only took a minute or two before I was as hard as I can remember being, and Linda just straddled my hips and impaled herself on my girl cock. We both moaned as she sank all the way down so that her shaved twat was pressed against my pubic bone. I flexed my PC muscles, clenching my still-stretched ass and making my girl cock swell. She moaned and tightened down on me.

Linda began to grind her hips against me. I could tell that she just wanted to come and wasn't interested at the moment whether I climaxed or not. "I love this big cock you have, Jessie," she breathed. "It fills me right up...I'm gonna come easy...I bet you'd love to watch me ride you while I diddle my clit."

I moaned my agreement. Still wrapped tightly around me, she leaned forward and pulled my blindfold up. She was a vision. Linda, this tiny domme, impaled on my shaft, her face flushed and her nipples standing out at attention. They were perfect for her breasts, about the size of a pencil eraser but just a little thicker.

I could only moan and watch her use my cock essentially as a dildo, grinding her hips and alternating between pressing her clit against my body and using her fingertips to give her the stimulation she clearly wanted. There were no more words from her just the exquisite sounds of a woman on her way to a powerful orgasm.

Suddenly Linda threw her head back and cried out. Her cunt was a vise around my erection. I clenched my muscles to get even bigger for her and I felt a gush of her juices. "FUCK, that was good!" she exclaimed, breathing hard. "I'm gonna come all over you, Jessie," she elaborated, now lifting her hips off of me and settling back down. That felt way better to me. I tried to agree with her, mumbling and moaning.

Within two minutes, she was getting close again. "Are you ready for me to come all over you, little girl?"

Another moan of agreement. I was starting to get close to coming, too. I hoped that she wouldn't be done after this orgasm, leaving me hanging and horny.

"Here I come!" she cried. She lifted herself off of me and put one foot down to my side so that her pussy was right above my lower abdomen, diddling her clit furiously. She screamed and shuddered, and all of a sudden fluid squirted out of her and added to my own cum on my chest and belly. She was shaking and twitching, and as soon as she finished squirting, she rammed herself down on me again, prolonging her orgasm.

As soon as that one finished, she started riding me with fury, only needing another two minutes or so before she pulled off again and squirted all over me again. I felt so submissive with both my own cum that she had squeezed out of me all over my body and with her girl cum dripping down the sides of my belly.

Then she slammed down on me again and rode me to still another orgasm. This time she just stayed on me, shaking and almost screaming, clamping down so hard on me that I came deep inside her. I pulled my head back, setting my nipples on fire once more, screaming into my gag.

Linda stayed on top of me as we both caught our breath. "Good girl," was all that she had to say for several minutes. She climbed off of me and gently removed my left nipple clamp. I almost screamed as fire shot out through my whole body. She immediately took it into her mouth, gently licking and suckling which felt wonderful as a counterpoint to the pain. She repeated the same process on my right nipple, which had the same effect on me, then she unbuckled my gag.

"That was amazing!" I told her. She kissed me deeply.

"Yeah, it was. It's not often that anyone can make me come that hard, especially not that many times. You're amazing, Jess."

"You are, too," I sighed as we kissed again. After it broke, I added, "I've never been fisted before. That was incredible. Thank you."

She began to untie me. "I've never fisted a girl like you, either. Did you like me coming on you?"

"That was so hot! You know that I'm a switch but that made me feel so submissive. I loved it."

Another kiss. "Good." Linda started taking her clothes off as I stretched out and rubbed my wrists and ankles.

"Do you mind if I take a shower? I'm covered in cum," I asked.

"Only if I can join you," she answered with a grin.

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We soaped each other up and showered sensually but we were both spent. As we'd already agreed, I was sleeping at her place.

Linda and I got into bed together, and as I relaxed, I thought back on how I'd become who I was then.

It started when I was a man dating a woman in my early twenties. She worked for a technology company that was developing nanotechnology. One of the first practical applications, oddly enough, was a pair of prosthetic breasts that used nanotech to connect to the wearer's nervous system.

She and I had talked and she was nothing but supportive when she found out that I enjoyed cross-dressing. In fact, the sex we had was even better when I was dressed. We would both get all dolled up in lingerie and makeup, and make love like lipstick lesbians. I was ecstatic when she brought the prototype prostheses home and wanted me to try them on. I did, and our sex life got even better when I could have breasts that felt completely real to both of us whenever I wanted and then I could just take them off.

For a while. What I didn't know, and the company didn't find out until later, was that some of the nanobots stayed in your body, dormant. Even after you'd removed the breasts. It was pretty poor testing, truth be told, and for a while I considered myself to be paying the price.

I was in a car accident during a thunderstorm. I was fine, but there was a lightning strike very close to me while I was outside of my car. I felt a little weird, but I just chalked that up to the voltage of lightning. Until I put the forms on a few days later.

We had incredibly hot sex, both of us wearing lingerie and made up, and once we had finished, I went to remove the forms...and couldn't. I obviously freaked out, frantically wondering what the hell I was going to do when I had to go to work the next week and I couldn't get the big tits off of my chest.

I took some time off and my girlfriend brought me in to the company's labs for some tests and hopefully for some help. No matter what they did, they couldn't get the boobs off of my chest. It took over two weeks that burned a fair amount of my vacation time. During those two weeks, my voice started getting less masculine, and none of my body hair grew. At all. I had shaved my body the night that it had happened and not only did I not have any stubble, my skin was softer than it ever had been and no body hair was growing at all.

At the same time, I had a dull ache in my pelvis and my still-functional penis was very tender. I finally noticed what was happening when my hair had grown almost a foot in a week. I was exhausted from all the tests but later their engineers and doctors figured out that for some reason, the nanobots had gone on their own and were reconstructing my body. I had always been fascinated by and attracted to transwomen and I didn't tell them right away, we figured out that the bots had somehow managed to transform me into my dream girl. I had 38-inch hips, a narrower waist, and my dick grew from about six and a half inches to eight, gaining quite a bit of girth, as well. My new body didn't grow any hair below my eyes and I had a very feminine voice.

I was a wreck, emotionally. I didn't want to be a woman! I was perfectly fine being a man and wearing some of her clothes! I ended up quitting my job, the company paying to put my stuff into storage while they tried to undo this. I dealt with severe depression for a month, but some counseling gradually pulled me out of it.

Despite their best efforts, there was nothing that they could do. I was stuck this way. After a lot more counseling and tests, I began to accept that this was the new normal. I legally changed my name to Jessica and got my new gender legally recognized.