Expecting

*disclaimer*

All characters in this story are over eighteen years of age. I wrote this story more than a year ago and it had difficulty passing the Mods which was the primary reason I pulled all of my works. Hopefully, I've made the needed changes to not cause any issues with this edited version of the story.

While this story is a work of fiction, one of the characters is actually based off of real person who has sadly disappeared from the internet.(if you know, then you know.) Oh and Lena Kelly is real too ;)

Expecting

I don't know how old I was the first time I saw a pregnant woman, but I know that it had a lasting effect on me. As a teen, I'd see a pregnant woman and always thought they were just beautiful in a very non-sexual, and innocent way.

My senior year of high school, I saw a student that was clearly pregnant walking down one of the hallways. I couldn't fathom that, she hadn't finished school and was already expecting a baby. Seeing her, and she clearly looked perfectly content with her condition triggered something in my head that I can't explain, but I began to imagine myself in her shoes, living my life as a high school senior, and preparing for the eventual birth of my child.

I recall laying in bed, wondering who the father was. I imagined a number of different people, including both teachers, and maintenance workers. It didn't enter my mind that she may have been intimate with another student, that seemed too boring to me. No, she had ended up in her predicament because an older man had somehow tricked her into sex, and then again when he inseminated her. It's important to note that this woman was over eighteen years old.

Look, I'm not suggesting that I'm normal, but most 18-year old guys aren't very normal.

This fetish took several turns, there was a phase where I imagined that I was the father. I'd have body-shaking orgasms jerking off imagining having sex that resulted in a pregnancy. My online porn searches had inevitably focused on pregnant women. I'd marvel at the size of their areola, the way their belly-button would sometimes protrude from their heavily swollen tummies, the way a kind of line would vertically travel along the middle of the abdomen towards their vagina, the linea nigra. All of it, and especially the clearly burdensome way the stomach would distend and cause the women to eventually almost waddle as they walked combined to keep me endlessly aroused.

After high school, I decided that I had to stop making excuses for not having a social life and finally sack up. If I needed to be turned down a hundred times before a woman accepted an invitation for coffee, or pizza, or whatever, then so be it. My main problem had always been my introverted nature, and I suppose the looming specter of being turned down somehow felt like an embarrassment that would be too great to deal with.

It was easy enough while I was in school, I reasoned that as soon as someone turned me down, the entire school would hear about it, and I'd never be able to show my face there again. It's easy to find excuses to not do the things that seem scary. My name is Chet, and as far as I know, I'm not ugly, in fact I can honestly say that I think I'm a good looking guy, not in the asshole-jock kind of way, but I've always been able to maintain what I consider a slender, but athletic body. I don't exercise, or eat any special diet, it's genetics. I'm a touch over 5'8" (173cm), with light brown hair, hazel eyes. I've watched for years as guys have regularly amazed me with the women they've managed to hook up with. Sure, I'm jealous, but I can be jealous and still wonder how a guy that constantly wears dirty clothes, rarely combs his hair and likely hasn't used a toothbrush in ages ends up with no shortage of women.

Jealous, but still boggling at how this happens so often.

I started a job doing customer service for a gaming company that I've been a customer of for years. The work was easy enough, and I got to work from my bedroom. Spending my days either emailing customers, or calling them really helped with my shyness. I've lost track of how many times I was on the phone with a woman who had a voice that almost always resulted in me getting an erection.

'Hot women play this game?!' I'd ask myself regularly, although that was ridiculous for me to just assume they were all hot.

One particular call really got to me. The woman had called in asking about a simple billing problem, as I brought up her information, she told me how much she enjoyed being able to play, as she was in her last trimester, and it was difficult for her to get up and be as active as she had been before her pregnancy. I cleared up her issue, and we ended the call, but I was incredibly aroused. I stood up and paced around my bedroom, imagining her in a recliner with a gigantic belly, legs spread, and her pussy hanging slightly open, preparing itself for its eventual physically-altering trauma.

I checked back in with my Dept Manager to take a break, and peeled my jeans off, intent on jerking off. My gaming chair is comfortable enough to sit in all day, and I can adjust it to whatever position I'd like, so I leaned back, spread my legs and began slowly stroking my cock. In my mind's eye, I imagined that woman, with her distended belly, struggling to move around. I had to stop, because I wasn't ready to cum just yet. A few moments later I resumed, more slowly now, picturing her reclined as before, but moaning as she slipped two fingers into her glistening pussy. I had to stop again, I was so close. I closed my eyes, and tried to imagine what it must be like to walk around with all of that added weight, and decided to see if it was possible to replicate that.

I stood and folded a pillow from my bed in half, then pushed it up under my t-shirt. It looked ridiculous. So I snuck out into the living room, still with no pants on, and collected a few of the small throw-pillows from the couch. Back in my room, I figured out how to use a single throw-pillow, and a few bunched-up t-shirts to give myself what reasonably looked like a pregnant belly. I paced around again, but a small pillow and some t-shirts don't create the kind of weight women deal with during pregnancy. I made a show of waddling around, and smirked as my erection waved in front of me. Back in my chair, I resumed masturbating, and pictured the woman from the call, except this time, instead of a glistening pussy, she had a reddened, erect cock that looked exactly like mine.

The first spurt launched high into the air and landed on my chin, the remaining spurts stained my t-shirt, with the final jets dribbling off into my pubic hair. I wondered if pregnant women ate their own cum after jerking off. The moment had passed, and the thought of wiping my chin off and gobbling up the mess I'd made had shifted from 'naughty' to 'no fucking way'.

Everything changed after that.

My masturbation sessions almost always involved grabbing one of the pillows from the couch, adding a few t-shirts to give myself the belly that I had been infatuated with for years, and edging myself into explosive orgasms that sometimes left me feeling ridiculous, but other times left me wanting more.

After five months at my job, our Shift Lead was promoted, and the CS Manager sent me a Zoom meeting invite. I imagined that he wanted to touch base with everyone to reassure them that everything was fine. To give you an idea of how bad this obsession had become, I had my pillow belly on during that call, although the camera on my work laptop was angled to only show my face.

The CS Manager asked me if I'd be interested in the shift lead role, it meant more money, more responsibility and people higher up on the food chain would be more likely to take notice. He explained that if I did a good job, I could expect more opportunities to open within the company.

I couldn't believe it, I'd only been working five months, and had been given a promotion, more money and I wasn't yet nineteen. My plan to masturbate after the call faded, and I decided to do the best job of being a shift lead that the company had ever had. I made another convenient excuse, I'd save my money, get an apartment, and then it'd be much easier to ask a woman out. I'd have my own place I could bring her back to, and gently impregnate her.

My life had been an ongoing series of plans, and excuses.

~

The work was sometimes more difficult, having to deal with upset customers, or handle the additional workload when other employees called off, or had appointments that took them away from work. The money made it all worthwhile, and three months later, I signed a lease on a nice studio apartment that was close to downtown. I finally felt like I was moving on with my life, and scolded myself to stop making excuses.

With my newfound confidence and practiced ease of speaking to women on the phone for work, I decided that I'd ask someone out before the end of the week that I'd completely moved into my new place. There was a bakery/coffee shop a few blocks away that I had passed several times during my daily walks, not being a coffee drinker, I'd never gone in, but passing by, it was impossible to miss the blonde-haired beauty that was often working behind the counter. Her smile was what caught my attention the first day, it was like she had polished off a bunch of energy drinks, she moved around so energetically, and had this big, beautiful smile.

I figured, go big, or go home.

The following day, I was a nervous wreck, I had committed to asking for her number, but I'd never even interacted with her yet. So I made sure I had on a nice pair of jeans, and a collared shirt, then took my daily walk, and went inside the bakery.

"Hi there!" She greeted me with that incredible smile.

"I've walked by a bunch of times since I moved down the street, and finally decided to see what kind of tasty treats you have here that I probably shouldn't eat." I said, hoping to sound confident, and witty.

"Everything here is bad for you, but that doesn't mean it's not delicious. So you've gotta ask yourself if you like to play it safe, or not so safe." She said back as she slowly waved her hand in front of her, to tempt me with the glass cases filled with the baked goods of the day.

I asked about a few different items, asked what she liked best, and decided on a number of different sugary treats. She wore an apron with her name embroidered on it and I even managed to give her my name, as I promised to return and let her know which pastries I liked the best.

The entire time we talked, it felt as natural as talking to women for work had become. I caught myself thinking everything was going perfectly, and re-focused. After I paid for the items, I turned and saw that I was the only customer, it couldn't be a more perfect setup, nobody but the two of us there, nobody to laugh in case she shot me down.

"I'll definitely be back." I said, and then screwed up my courage and went for it. "Hey, can I get your number?"

Her smile faltered for a minute, then returned and she apologized, I saw it all coming apart. I felt my stomach rising up into my throat, and the beating of my heart was pounding in my ears loudly enough to just barely hear her voice as she held out her left hand, and wiggled her fingers.

"Oh, I'm sorry, but I'm married."

I looked at her finger, and finally noticed the engagement ring, and wedding band. I felt like a complete, and clueless loser.

"Wow, I'm really sorry, I should have looked, I feel stupid." I said, feeling just as stupid as I'd said.

The smile was back, and she told me it was okay, that I wasn't the first person that had asked for her number, and that a few had even told her they didn't care if she was married.

It didn't matter, I'd made an utter fool of myself, I'd finally gotten to a level of independence, and holding down a job that I enjoyed, and the first woman I'd actually interacted with, to possibly have a date turned out to be a married woman.

All of the progress vanished in a heartbeat.

-

I went back into my shell, and worried about work. When I wasn't working, I masturbated, and sank deeper and deeper into an addiction of watching porn. Always pregnant women, and I eventually found a video of a Trans woman that had some kind of phony pregnant belly, that really captured my attention. I had no idea that imitation pregnant bellies were being produced, an online search revealed a Chinese company sold multiple variations, there was one that included breasts, and an option to have the linea nigra added. I hesitated for a moment, but then clicked on the 'Purchase' button, and hoped for the best. It wasn't a small amount of money for me to spend, but I'm pretty sure I would have spent twice as much if I knew there was something like this, made well.

I imagined caressing my soon-to-be swollen belly as I masturbated. I knew it would be difficult to remain patient until the package arrived, but it eventually did and thankfully my initial impressions were shockingly good. It was heavy, which was important to me, and the color of the silicone was nearly a perfect match for my skin. After opening the package, I decided that I needed to wear it immediately, and finish my shift as a very pregnant... pregnant what?

Admiring my purchase was one thing, squeezing into it, and getting it situated on my body was something else entirely. When I finally had everything in place, I realized that I owned no clothing that would cover my body. I now had generous D-cup breasts, and an enormous belly. Both wiggled as I moved in a mesmerizing way. Aside from the obvious seams that I hadn't considered, all I wanted to do was relax in my chair, and coax an impossibly huge load from my testicles, hoping that I could cover my very pregnant belly, and swaying tits with my semen.

When I came, I think everyone on my floor heard me cry out, when I had finally settled down, I admitted that my belly and tits were worth every penny. After I waddled into the bathroom and cleaned myself up, I realized that getting out of the prosthetic would be almost impossible. I nearly panicked, and then just decided to leave it on for the rest of my shift. I had no video calls scheduled, and even if I did, I could adjust my camera to only show my face.

It was strange, spending the last three hours of my shift in what appeared to be a very pregnant state. After I logged off, I masturbated once again, finding the video I'd originally randomly found of the Trans woman, whose name was Lena Kelly (btw: this video actually exists!). She had on a striped dress, and I imagined that it made more sense for me to buy something like that, instead of a gigantic T-shirt to wear over my tits and belly.

Watching her suck the guys dick, and then later on her hands and knees as he fucked her seemed almost surreal. As I stroked myself, I imagined myself in her place. Not that I fantasized about men, but in my very 'family way' it seemed ridiculous to want to fuck a woman. It was nice to pretend, just while I have my tits and belly on, to want a man inside of me, after all, I couldn't get anymore pregnant right?

Afterwards, my moment of panic returned as I struggled to get out of my tits and belly. I eventually worked out a process, and made a note. I'd need time to get this off in the future, any unexpected knocks on the door of my small apartment could be tricky.

I logged into Amazon, and looked for a dress that was similar to Lena's, I settled on something that looked close, a clubbing dress that was obviously not appropriate for someone in my condition, and then I found a long blonde wig with bangs that was similar to her hair and bought that too. Less than a week later, I opened my packages, and lucked out when I found the dress fit, although it was certainly tighter in some areas, heheh.

I watched that video multiple times, while wearing my tits and belly, wearing my new dress and the wig, and imagined myself in Lena's place. I lay on my bed, with my head hanging off of the edge of the mattress, pulling down the front of my dress and exposing my heavy tits with their dark areola, my mouth was agape, imagining a man thrusting into the back of my throat. I had to move my hand slowly along my engorged shaft, it felt like I was on the verge of cumming continuously. I mimmicked Lena's position, moving to my hands and knees, it felt strange like this with my tits and belly weighing me down, and I continued to stroke, I rubbed a finger around the wrinkled flesh of my anus and imagined the man fucking Lena was fucking me. Finally I couldn't last any longer, so I rolled onto my back, and shot my load that landed on my distended belly.

There were a few moments of being disgusted with myself, but that feeling faded and I decided to take things to the next level. I was back on Amazon, and I ordered a dildo (with balls, because they just looked weird without them.) and a bottle of lube.

When the package arrived, I nearly called off work for the rest of the day, but ironically, the excitement of voluntarily denying myself until after work brought its own strange kind of pleasure. After dressing up, I opened the package, and went about the work of learning how to fit the dildo entirely in my mouth. Even with dangling my head over the edge of my mattress, I found myself gagging. This would take some practice.

After I'd accepted that I wouldn't be able to completely accommodate the dildo on my first day of trying, I loaded up the video of Lena, and once again mimicked everything on the screen. When it came time to be fucked, I was shaking with excitement. I attribute my desire as the primary factor in pressing on when I felt like I was going to rip myself open. Instead, I paused the video, and relaxed as well as I could and then resumed pushing in a tiny bit, then relaxing, and pushing once again. The feeling was difficult to describe, but as more time elapsed, I could feel that I was clearly making progress, eventually, the next push resulted in a kind of 'Ouch-Ohhhh' moment when the ring of my anus had finally stretched enough to accept the toy, and then sealed back up around it. If you've ever had a dick in your ass, you know exactly the feeling I'm describing, there's a kind of relief/accomplishment that's hard to describe.

Things moved a bit quicker after this, eventually I had the toy fully inside of my body. Did it feel fantastic? Not really. In fact, I felt like I was stuffed to the point of wanting it out, immediately. But I kept it deep in my bowels and marveled at how easily Lena handled the real dick that was pounding into her.

I definitely needed more practice.

~

Nearly a month later, our company was going through the process of year-end reviews. I felt confident that I'd done well, and would be surprised if I didn't get a positive performance review. When the day came to have the video call with my Manager, I had on a generic T-shirt, but what the camera didn't show was that I also had on a cute dark gray pencil skirt, nude pantyhose, and a pair of 6" stripper platform heels.

The review went well, my Manager made a point of telling me that I'd hit all of my goals, and that I was 'easy' to work with, it was strange hearing him say that caused my dick to tingle a bit. At the end of the call, I was told that I had a raise approved, and that I should expect an email with the details within minutes. I logged out of the call and waited impatiently, and when the email arrived I couldn't stop smiling. I enjoyed my job, and my employer enjoyed my performance. I had my own place, I could indulge in my daily masturbatory fantasies, and now, I was making even more money than I ever had before.

I celebrated by ordering a ridiculous amount of cosmetics, and when they arrived, I realized after an hour of catastrophic results, that I had no idea what I was doing. I also learned that makeup doesn't easily wash off. I did the typical reddit searches, found links to tutorial videos, I found links to sites for crossdressers that had a wealth of knowledge, and while I didn't consider myself a crossdresser (ummm...) the information was invaluable. I regularly participated in group chats on one of the bigger CD sites, and made several friends, all of which were far more experienced than I was.

Because I had no social life, and because I didn't have to hide locked away in my bedroom, I had plenty of time to practice things, important things like teaching my gag reflex to settle the fuck down, and how to give myself beautiful eyes, and thick, luscious lips. Fucking myself became easier, but in truth, it always felt like I needed to use the bathroom in the worst way when the dildo was inside of me. I wanted it to feel amazing, I wanted ot experience the pleasure that Lena was clearly experiencing, but the truth is, that filling my bowlesl with a replica cock just felt naughty, and not something that I'd be able to orgasm from.

I chatted with my CD friends online, and asked if it was normal, and they all just told me to make sure I was clean back there before playing, and that the more I played, the better it would feel. There was one girl named Paige on there that seemed a lot like me and we either chatted or passed DM's back and forth quite a bit. I confessed my obsession to her, and after some back and forth she had convinced me to send her a photo of myself. My makeup skills were pretty good, especially when I didn't have to worry about slutting it up too much. To be clear, there were definitely times I enjoyed slutting it up, making myself look like a whore with a huge belly in my heels and dresses that were far too short were celebrations that had always ended in fantastic orgasms, but for a simple photo, I wanted something far less risque. After stressing over the many photos I'd taken of myself (ironic how that seemed like something any woman would do.), I sent off the photo that I was most content with.

Later that night, Paige sent me a DM with a photo of her as well, and I immediately knew that I had a lot of work left to do. Paige was beautiful, and naturally she had picked a photo that she was similarly happy with, photos like this always have a way of erasing imperfections, or other little things that we can't remove in our actual lives. In spite of that, she just had an incredible fashion sense, had accessorized herself with pretty rings, bracelets, a cute heart pendant and pretty little earrings. She had long, shiny red fingernails that matched her lipstick and the look on her face, while subdued, still entranced me. As simply as I can say it, I wanted to fuck her. I know Paige didn't have a vagina, I know that Paige is a man, that occasionally dresses as a woman, I know that Paige has a penis, I know all of these things, and yet I wanted to watch my dick pushing into her mouth, I wanted to watch her ass cheeks as I fucked her.

The confusion of that left me questioning so much, and for quite a while.

I learned a lot from Paige, and we had always kept our chats, or DM's on the safe side, no dick shots, no sex, no nudity. We had become 'girlfriends' in a way. I asked her about her earrings (Paige is married) and she said her ears had been pierced since she was a teen, that where she lived, it was quite common to see guys with earrings. I decided to pay attention and see if that was the case where I lived as well. Of the many things I learned from Paige was to pay attention to women in public, watch how they walk, watch how they hold their hands, observe their mannerisms, pay attention to how they hold themselves, pay very close attention to their confidence, because women have plenty of it.

A week later my ears were pierced. I hated the little studs I had to wear initially, but I'll also admit, it excited me to go out in public where people could see my new earrings. I had bought a few other bits of jewelry, a delicate silver chain with a butterfly pendant, a few pretty rings, and a few bracelets. Paige said that she used glue-on nails, that she couldn't walk around in 'guy mode' with long nails, but that she kept her toenails painted all of the time.

Each of these steps gave me more confidence, and satisfaction. I regularly looked back on the photo of Paige, and could honestly say that I was making progress, I had more work to do, but I was on my way to being either a subtly pretty pregnant woman, or a pregnant slut.

Six weeks later, everything went to hell.

-

I had another meeting invite sent by my Manager, and I played everything back that had happened recently, there were the usual number of upset customers, and I fixed the problems when I could but nothing that was out of the ordinary had happened, and so I wondered if perhaps someone higher up had taken notice of my good performance, and could this be another promotion? I calmed myself, and just waited till it was time to join the meeting. It was a Friday afternoon and I hoped that some kind of excellent, unexpected good news would lead me into the weekend that I'd planned to spend quite pregnant and misbehaving.

"There's no good way to say this, but you're being laid off. The company is laying off quite a few employees, it's completely out of my control and I've made it very clear you're one of our better performers. The HR people made all of the decisions on who would be let go. It's not much comfort, but you'll be getting a modest severance package, and I'd be happy to serve as a reference for you as you begin to look for another job." My Manager said, he looked upset, and I just stared at him, likely with my mouth hung open, not knowing what to say.

"I'll take my old job back, if that's an option?" I finally asked, hopefully.

"I'll be honest, this place is going to be a madhouse for the foreseeable future. We're going to be working with a significantly fewer number of people, dealing with just as much work as we've always had. I don't understand how they are expecting us to get the work done with so many empty seats."

And just like that, I had no job.

No way to pay rent, to buy groceries, to remain independent.

I made a promise that I wouldn't move back home, I had a year long lease on my apartment and no intention of breaking that, and potentially wrecking my credit before I'd even turned twenty.

That weekend was miserable, I stayed in bed, I stressed and then I stressed some more. On Monday, I began applying online for similar roles at other companies. I'd spent the first part of the morning revamping my resume, but no matter how much creativity I could muster, the fact was, this had been my one and only job. I hoped for the best, but didn't expect much.

By that Wednesday I had accounted for all of my expenses, reviewed my meager savings and then considered the severance (one month of normal wages, and continued medical benefits for six weeks) and realized that I needed to have a job with a deposited paycheck sometime very soon after two months from that day. I decided to start applying for jobs locally as well, I went to the various larger retail stores in the area, restaurants, even gas stations.

The following week, I was contacted for an interview at a gas station. I knew it wouldn't pay enough to keep me in my apartment, but it was something.

The interview went well enough, and I was offered the job, however it was part time. I imagined that may have been a blessing, as it allowed plenty of time for me to continue applying elsewhere, and still make some money until a better job could be found. That night, I ended up in a chat with Paige, I told her what had happened, and she was sympathetic. When I told her I would be starting a part time job at a gas station the following week, she asked if I'd ever considered working for myself.

"I'm not sure what I can do. I mean, I like to play online games, and know how to handle customer support. I don't think that qualifies me to start my own business." I said.

She sent me a link, and I could hardly believe it, but Page had an OnlyFans account, and she seemed to be doing pretty well for herself. She had a large number of subscribers, her monthly subscription cost was low, but she explained that she made more money by selling videos that cost extra.

She sent me a link to a video, and it was Paige dressed in lingerie, on her hands and knees on a bed, as one of those motorized fucking machines plunged a dildo into her ass.

The video was very erotic, this was a side of Paige that I imagined existed in the quiet confines of her home, when she had the time to dress up, but having an OnlyFans account was unbelievable.

We talked for almost an hour, and after we were done, I created an account as well. I found myself excited at the thought of similarly bending over, and being railed but I had no machine of my own. I then imagined recruiting some attractive stranger to actually fuck me, and selling the video. I finally snapped out of it, and realized that I was still woefully behind the curve on my ability to arrange a date, how could I possibly imagine being able to skip the dating, and just arrange sex.

The next day, I chatted with Paige once again, I poured out all of my concerns, and questions. By the end of the chat, I had another account on a site called Chaturbate. I watched as men, Women, and Trans people sometimes interacted with viewers, sometimes kept their faces in their phones, and sometimes just constantly typed away, apparently responding to DM's that viewers had paid for.

I started taking notes, and all the while asking myself if I could actually turn my cam on, and jerk off to however many viewers may be watching.

A concerning issue I had though, was that the people that either disguised their faces, or simply didn't show their faces seemed to have fewer viewers. I didn't want anybody to see my face, I may be unemployed and without friends, but if somehow news of me being a camgirl got back to my parents, I'd have to move to the middle of the jungle to escape their disappointed stares,

I chatted with Paige once again the following day, and expressed my concerns.

"I don't worry about it, if someone can somehow recognize me, then there's nothing I can do about it. I've been making videos for more than a year, nobody has ever been the wiser.

That night, I set up my webcam, the view wasn't terrible. I sat at my desk, with the webcam set off to the side, showing what would have been a sideways shot of me from the neck down. I had on the first dress I'd bought, and even though I wasn't going to show my face, I made sure to get my makeup just right, my blonde wig was long enough to be seen in the video, and I decided to start broadcasting. As far as I could tell, I was the only pregnant woman with a dick on the site. I had my channel in the Trans category, obviously even though I'm not Trans, I'm just a guy that has a fetish for pregnant bellies, and big swollen titties. I also really enjoy applying my makeup, and have gotten increasingly better at fitting more of my dildo into my mouth, but make no mistake, I'm not really Trans.

Pretty quickly, people started joining my channel, there were plenty of 'You're not Trans!' and 'Wrong category!' chats, but there were also a number of compliments, and asking how much it would cost to tip for various things. 'How much to see your dick?' 'How much to get naked?' 'How much to see your feet?'. Things like that, I made mental notes, and decided to make a list, and figure out what I should charge.

By the end of the broadcast, I'd accumulated a fair number of followers, and I felt like I could maybe make this work out for me. I felt sexy, I had viewers complimenting me, some telling me I looked beautiful, sexy, that they wanted to fuck me, or suck my dick. That one broadcast did more for my confidence than anything else ever had. The following day, I celebrated the good news with Paige and she seemed genuinely happy for me. I asked her plenty of questions, and the big one 'What is the best way to make the most money the fastest?'

"Find someone to fuck, or someone to fuck you." She answered.

"Not possible, I've tried that for years, I still have no idea how to make that happen." I answered before realizing what i'd said.

"Wait, are you a virgin Chelsea?" She asked. I had taken to calling this version of myself Chelsea

"OMG, I'm so embarrassed."

"No messing around, are you serious?"

"Sadly, it's true."

"You have no idea how hard you just made me."

"Really?"

"Chelsea, I would love to be your first, no pressure, but you're very pretty, I'd love to fuck you."

"But you're married."

"I think the wife would be a lot more flexible with me fucking a pretty pregnant Trans girl, than any other kind of girl."

"I'm not Trans though Paige, it's just a turnon is all."

"Okay sweetheart, whatever you say."

~

I started camming every night, and while I was making tips, the website took a lot of that money, and they didn't pay out like a normal job. I became more comfortable talking to my viewers about sex, and may have told a few white lies about hooking up 'with my guy' on the weekend, and many of them told me they'd love to hook up with me "Tell your guy there's enough of you to share." the chats began ending with me edging for the last hour or so, and then my dick erupting in the air like a volcano.

I felt silly working part time in a gas station, and then jerking off while wearing nylons as I told whoever the nights high tipper was that I could imagine his 'big hard cock' giving me the kind of fucking a slutty pregnant Trans girl needed. I became closer with Paige, who continued to give me pointers and then a week later, I stopped caring and began showing my face on cam and was immediately rewarded with heaps of praise, and curiously enough, marriage proposals.

"I'd take good care of you Chelsea, and I'd make a point to keep your sexy belly big and swollen like it is right now."

That was my weakness, hearing these strangers tell me they'd keep my pregnant, or that they'd make me stop taking the pill, or that they'd make a point to time things perfectly so that they'd have the highest chances to impregnate me once again.

I mean, it was all just fantasy, I wasn't really pregnant, I wasn't on the pill, I couldn't get pregnant, and most of all, I wasn't really Trans.

"Let me fly you out to California, just for a lunch date. If we don't hit it off, you say as much, and then you have a few days to explore at your own pace. I just have a feeling that we'd get together Chelsea, and I can promise you I'd treat you like the beautiful woman you are." One guy offered.

"I'll pay for your surgeries." was another offer, and the thing was, I didn't want any surgeries.

I started sleeping in a nightie, I'd been shaving my legs, and armpits since starting to stream, I was using female deodorant, my toenails were always painted, however I wore the glue-on fingernails as I was still just boring Chet when I left my apartment, then one night I had a curious request.

"Sweetheart, if you take some photos outside, nothing erotic, just the day-to-day Chelsea as she lives her life, I'll buy whatever you want from your wishlist."

My wishlist was surprisingly tame. Just clothes a pregnant woman would wear. No heels, no dildos, no expensive cameras, no fancy gaming computers, I think the most expensive thing on my wishlist for just over $60USD.

The truth was, I wasn't entirely sure I had an outfit to wear outdoors that a respectable pregnant woman would wear. Everything was too short, too tight, or too slutty.

Besides, I was terrified of leaving my apartment as a pregnant woman.

"Someone requested a few photos of me out in public." I told Paige.

"Be careful if you do, make sure there's no landmarks a sicko could use to get an idea of where you live." She warned.

"Have you gone out in public Paige?" I asked.

"Countless times, and before you ask, yes, I've been clocked, several times.

"Clocked?"

"It's what they call it when your disguise fails to convince someone, and they either say something, or otherwise make it clear that they know you're not a woman. Speaking of, it's always been women." She explained.

"Now I'm definitely not going out in public, you look so much better than I do, if you were 'clocked' then I know everyone would see that I was just pretending to be a woman."

"Nobody would expect a guy to dress as a pregnant woman, nobody would guess you're a guy."

"I don't know, maybe if I can get my confidence where I'd like it to be."

"Take your time sweetheart, there's no rules for this journey you're on, aside from doing what makes you happy."

"What would make me happy, would be not being a virgin!" I laughed.

"I'm serious Chelsea, I'd love to make you a woman." Paige said, and then there was silence.

It was an awkward few moments. I'd always imagined losing my virginity to a pretty woman, and then having sex be less of a stressful thing, it would be easier after the first time, it would have to be easier right? But I had trapped myself, or maybe a better explanation was that once again, I had created the excuse to not find a woman. My legs and armpits were shaved, my toenails were perpetually fire-engine red, and what normal woman wants to date a guy that looked like, well, that looking the way I was changing myself. In truth, I couldn't recall the last time that I had masturbated thinking of having sex with a woman. I tried to excuse it all by partially blaming my transformation on doing 'my job' for camming, but there was something forbidden, dangerous and extremely erotic about the person I was becoming.

I accepted that I was probably further from having sex with a woman than I ever had been, and there was a certain allure to being the woman. The idea of a man penetrating me, fucking me, and then orgasming inside of my body was something that also excited me. Paige offering to be my first, that was totally different. Did she mean that she'd dress up as Paige, in one of her beautiful outfits, and then take me to dinner somewhere, eventually bringing me home and making love to me? Did she mean that she'd show up in guy mode, and treat me like a woman, and then make me a woman later that night.

"How would that work?" I asked.

"However you'd like it to work."

"Would you be Paige?"

"I could be, would that work better for you?"

"OMG, I'm actually considering this."

~

Six weeks later, with the highest number of viewers I'd ever managed to attract, I whimpered into my mattress as Paige began slowly pushing her girl-dick into my ass. She had sucked my dick, and I lasted possibly two minutes before emptying my testicles into her mouth, she never skipped a beat and when she opened her mouth and showed me that she had swallowed everything, I know I had to do the same for her.

Sucking a dick wasn't nearly as hard as I imagined it would be. Paige was smaller than my dildo, and I'd been practicing with the dildo, so it really felt like I knew what I was doing, and the soft, sexy noises she made as I rolled my tongue on the underside of her dick told me that she was enjoying the attention I was giving her. When she finally pulled my mouth from her swollen shaft, she told me it she was going to fuck me. I was afraid, but I knew that I'd be able to take her dick inside of me, the dildo was bigger, and I could take that completely to the balls.

This was different though. She rolled a condom onto her dick, and teased my opening, and then asked if I was ready, I just nodded into my mattress and felt the warm liquid of the lube drizzle down along my ass crack, and then the head of her dick slipped inside of me with what felt like a gentle pop.

Her hands gripped my hips, and I felt her long nails pressing into my flesh. I simply allowed her to take me, and before long at all, she was fucking me in the way I suppose I'd always imagined would be the way I'd fuck a woman. She withdrew until only the head of her dick was in me, then pushed fully forward until there was no more to give, then repeat those steps as my body quickly adjusted to her being in me, the sensation was vastly better than the dildo. Paige felt both softer and harder at the same time, and it wasn't lost on my that a real penis was buried inside of me, and I finally had to question whether or not I was Trans, it's a subjective thing and you don't need tits, or to live 24x7 as a woman to be Trans. Yes, there are transgendered people that do live that way, but there are also plenty of transvestites, like Paige and admittedly like myself that are not full-time women. But in that moment, all I could think of was how perfect I felt. I gazed dreamily at my webcam, and imagined all of the viewers watching as they stroked their cocks, masturbating to me, masturbating and likely fantasizing that they were fucking me. My body shuddered with the excitement of it all.

The tips almost never stopped, and in spite of only actually receiving a fraction of them, I knew I wanted to keep doing this in the future. Paige eventually pulled out, yanked the condom off and came all over my asscheeks, if I could have scripted it, I would have preferred her cumming all over my pregnant belly, but it felt incredible, hearing the urgency of the sounds she made as she stroked herself and then the warmth as her semen painted my ass.

In that moment, I had no desire to play the male role, maybe it was fate telling me that I was better at being a woman than I had been as a man.

We closed the cam show, Paige went to the bathroom and came back with some tissues, and lovingly cleaned her load from my bottom, then we cuddled until she began to stiffen, and I sucked her dick until she came once again, this time in my mouth, and I was a good girl, and swallowed it all, just as she had done for me.

She had reserved a hotel, although I had invited her to spend the night, she admitted that her wife was waiting patiently at the hotel, and that there would be more sex to come for her. She apologized and said that she wished her situation were different, that she would have loved to have given me an opportunity to experience what pussy tasted like, and what it felt like, but her wife had never been interested in any extracurricular activities.

It sounds crazy, I know, but I wasn't overly concerned, maybe at some point I'd meet someone, but I was cock drunk, I just wanted more cock, and pussy was just something that seemed distantly possible.

~

I woke the next morning already horny, and wished that Paige would have been there to give me what a girl like me needed most of all. But I had no idea if she was even in the same city at that point. She may have already been on a plane back home.

I went online and bought a new pair of silicone tits, no pregnant belly this time. The pregnant thing was still deep in my mind, still very erotic, but I wanted more now, I wanted more sex. I went over my wishlist, and updated it, picking out nicer outfits, sexier shoes, plenty of lingerie and more bras than I could ever hope to have a need for. I'd replaced my boring studs with a sexy pair of hoops, and spent more time wearing my glue-on fingernails until one night, weeks later, I simply put on a cute outfit and drove to the store and picked up a few more cosmetic items and acted like the place belonged to me. I stopped caring if other people saw me and maybe worked out that I was a guy in a wig with big tits, I stopped caring what would happen, and my life became quite a bit happier. I quit the gas station job, and on the day I showed up to pick up my last check, I had on a cute skirt and a pretty tangerine blouse. The Manager never blinked an eye.

Less than a week later, a guy asked for my number, and I smiled, moved a bit closer and told him that I was a 'special girl' and he nodded and said that special girls like me were very sexy. We had a nice first date, Our second date ended with me giving him a wet, sloppy blowjob, and our third date I became his woman. I don't leave the apartment now unless it's as Chelsea, I haven't tossed my guy clothes, but I really don't have any use for them at this point.

I stay in touch with Paige and she's asked me a number of times about possibly beginning HRT. I've gone back and forth about it, and it may happen, but first I have to have a talk with my parents, and I know thats going to be awkward.

Dale (my guy) knows I have an Onlyfans page, and that I stream as well. I've asked him if he's interested in joining me, and so far he hasn't shown interest, but he hasn't tried to stop me. I recently had an offer to collaborate with another streamer, a guy and I'd jump at the chance but first I need to discuss it all with Dale. I could be wrong, but I'm pretty confident he'd love to see his woman fucked in front of thousands of viewers, I suppose we'll have to see what happens.

Oh, I should probably end this story about whether or not I finally accepted being Trans, but you're smart and you already know the answer.