A Picture Is Worth...

...at least a thousand nights of pleasure!

It was getting harder and harder to return to normal.  It all started as a lark when I met Tasha online at that TG site.  At first I thought she was like most of us there; guys fantasizing about being women.  Tasha would have been a Tom or a Todd, just like my Caitlyn was actually Calvin.  But she broke the ice and sent me a photo of herself.  I would have doubted it was really her if she didn’t have the website on in the background along with our most recent conversation. 

 We were a match made in heaven, especially during the pandemic where we were both isolated and alone.  I fantasized about a woman helping me to transform, she fantasized about transforming a guy into a woman.  My previous girlfriends had never been accepting of it and my mere mention of the desire was the normal clarion call of the end of our relationship.  Tasha’s boyfriend was a burly shopworker who had no interest in anything feminine for himself.  My return photo to Tasha showed that I had what she called the ‘bones of a woman’.  I was slight in stature, had an androgynous face at best, small hands, and fair skin.  So, we agreed to live out our fantasies through each other. 

 At first it was simple tasks she assigned me.  Stuff I’d done before but was now especially thrilling to do at the command of a woman and especially thrilling as I sent her photos of each completed undertaking.  Shave myself smooth all over.  Put on panties and stockings.  Wear a wig.  Put on makeup.  She even sent me items once I shared my address with her.  Stuff I would have had a hard time buying for myself.  Heels, corsets, sexier lingerie.  The incredibly realistic false breasts were something I’d never have imagined buying for myself. 

 When she had me glue the falsies on for the first time, I was scared to learn that she hadn’t included any adhesive remover.  She said it was already in the mail but that I’d have to live with my breasts for a few days.  When I complained about having to do my weekly shopping the next day… being out of toilet paper made this a necessity… she guided me into putting on a pair of jeans, one of her included hello kitty t-shirts, a pair of pink Converse she’d sent me weeks ago, a wig, and some light makeup.  This wasn’t exactly the glamorous over the top femininity I was striving for, but it worked to keep people unaware of my real gender.  The cashier confirmed it by saying “Thanks for shopping with us Miss.”

 Tasha was thrilled at the experiment and decided to tackle every obstacle in passing I’d come across.   Whether those impediments were real or only in my head, she tore them all down one by one. The voice lessons started that day and continued every single day.  Months later and I’d never get a job in radio with my femme voice, but when someone looked at me dressed up and speaking in my Caitlyn voice, they’d only hear a woman and not suspect a man was underneath it all.  And more and more I’d be dressing up as Caitlyn when I went out.  The adhesive the falsies required was long lasting and even with the remover, it was difficult to take them off after only 48 hours.  The instructions recommended wearing them for a full five days before taking them off. 

 The wig was next and was surprisingly the turning point in my outside life.  Tasha went all out.  Not only did she get an incredibly expensive wig made from real human hair matched to my own color, but she also had a specialist come in to weave it into my own hair.  I wasn’t up to speaking at that point so Tasha had me roughly cut my hair, dress in my Caitlyn ‘jeans and T’ outfit and wait.  The specialist arrived on time and I fell in with the story that Tasha had laid out.  I was supposed to be going through a medical treatment that not only took my voice, but made my hair come in rougher than normal.  I was supposed to have cut my own hair away but now wanted it all back without waiting.  And it worked.  The woman chatted away at me for the hours it took to work the wig in strand by strand without ever expecting a response beyond a smile or a nod.  Her conversation turned quite lude at several points, going over how my boyfriend was going to love feeing my hair brushing over his thighs as I went down on him or how he’d love to hold it in one hand as he took me from behind.  Through this conversation I could only blush what I assume was a bright red and nod.  I got so into it the pictures she kept painting of me and ‘my boyfriend’ that I hadn’t realized she wasn’t just washing the hair at point, she was coloring it. 

 The picture I sent to Tasha was stunning with my reddish-brown hair spilling over my shoulders.  Even without makeup on and pulling it back into a ponytail, it was incredibly feminizing.  But maybe that was from all this work by Tasha.  She’d stopped calling me Calvin a long time ago at this point and didn’t refer to making me pretty or sexy or feminine.  Instead, she just talked about making me prettier or sexier or more feminine.  It was like I was a plain looking woman who she was teaching to come out of her shell.  But the wig wasn’t something I could ignore or work around.  I didn’t feel that I could style it in a way that would work as myself.  Tasha’s recommendation was as brutal as it was simple.  Don’t go out as Calvin anymore.  Only leave the house as Caitlyn.  Any objection I had was cut short.  My voice was good enough for quick short quiet conversations and would get better with real practice.  My look had fooled everybody I’d encountered and that was before the wig.  I wasn’t going out with friends or meeting up people I knew since every social gathering place was closed.   And it’s not as though it was permanent, as I could cut the hair off at any point. 

 My only objection that gave Tasha pause was identification.  If I got pulled over by the police, my drivers license clearly identified me as Calvin.  A man.  I let her mull that over as I’d just glued on the falsies for the wig specialist and it would be days before I could remove them anyway.  Tasha said she’d take care of my concern but kept up our work.  When she sent me the realistic dildo I tried to balk, saying that I had always experienced lesbian fantasies, but her reasoning was sound.  Most girls were brought up as ‘straight’ and even if they never partook of men, they were still expected to know their way around the anatomy.  Her lessons on licking and sucking it were both thrilling and humiliating and I’m fairly sure Tasha fed off the humiliation.  Especially as she didn’t just want photos, she wanted minutes long videos. 

 When the package arrived the following week I thought it must be something official as everything Tasha sent me was delivered by UPS or FedEx.  This was a standard envelope from the US Mail service.  When I cut it open, however, I was in for a big surprise.  The first item I’d kind of expected.  A fake ID for Caitlyn.  Tasha obviously knew my particulars like eye color, height, weight, and even home address.  She had plenty of photos of me enfemme.  But the drivers license number was different than mine.  When I checked it out on the DMV’s website, I saw that it linked to… me.  Or rather, Caitlyn.  Everything was mine, just slightly off.  Same address, just with an apartment number.  Like Caitlyn was renting a room in my house.  Same height but the weight was a good 30 pounds less.  And the driver’s record even included previous driving infractions.  While my record was clean, it seems Tasha figured on Caitlyn being kind of a ditz.  She had enough points that any infraction would threaten her license and her violations included everything from careless driving to speeding.  From failure to yield to seatbelt violations. 

 If the realism of the ID surprised me, that was nothing compared to the rest of the contents.  Tasha didn’t just include the most realistic fake ID, she made an entire fake person.  Caitlyn had her own bank account that was opened four years ago.  Caitlyn had a rental agreement signed between her and my landlord.  She had a facebook account detailing the foodie shots she liked and the vacations she took.  She was listed as single but dating.  She had a LinkedIn account with a resume, a job history, and actual references.  According to that she worked as a freelance copy editor… similar to my own job as a freelance graphic designer.  She even had a local bank account with a sizeable balance. 

 When I confronted Tash about all of this, she just blew it off saying that she wanted me to be comfortable going out as myself.  Meaning as Caitlyn.  When I mentioned the weight difference on the ID she chided me that she’d start me on a strict diet and expected me to meet that goal very soon.  She even mentioned the balance in the bank account saying that she wasn’t going to buy me anything any longer.  Instead, she’d have me buy them myself.  She said as the account got low, she’d deposit more in making it look like I was getting paid for work gigs. 

 When I tried to back away, saying that she was investing to much into my fantasy she not only reminded me that this was her fantasy too, but that she was going to make me work for some of the money.  She’d actually be sending people my LinkedIn profile and they’d contact me for work.  Work as Caitlyn.  She expected me to answer the phone, take on jobs, complete them, invoice the customers, and accept payment.  All as Caitlyn.   Nothing about this process was sexy or even deviant, but it might be the single most mental thing that pushed me into being Caitlyn.  I wasn’t a fantasy or even sexy… I was just a woman working. 

 My days got busier and busier.  Working my job as well as the Caitlyn side hustle actually increased my earnings quite a bit but it took a good amount of time.  The remaining time was almost exclusively spent on Tasha and her tasks.  The first thing she had me buy was a full cosmetics kit.  I knew women spent real money on their makeup, but this cost me about a grand.  Tasha said that was mostly because I was starting with nothing, but admitted that she fancied Caitlyn as a fan of high end beauty products and aids.  Each morning I’d start by cleaning up and ‘putting on my face’.  Each afternoon I’d wash it all off and do it again.  And every night I’d have to wash it off again only to put on evening specific makeup.  This meant that I was constantly working as Caitlyn.  Receiving calls for Calvin now required a moment so I could clear my throat and get back into his mindset.  That’s one of the reasons I probably was getting less and less work as Calvin.   It didn’t help that Tasha was making sure that Caitlyn was a bright, funny, happy woman to deal with.  That bled into my emails and even my texts.  The clients ate it up and without prompting from Tasha, many became regular customers.  All the work typing out their projects helped me work with the new nails Tasha had me use.  At first, they were very temporary, but it was obvious that I wasn’t going out as Calvin anytime soon so I soon opted for the longer, more luxurious permanent nails.   And eventually as my own nails grew out, I was able to maintain that French manicure with my own self instead of any glue on product. 

 The next thing Tasha had me buy was a gaff.  She’d commented that several of my photos were ruined by the obvious bulge in my panties.  Even when I tucked properly, I had to keep my thighs pressed against one another, limiting my poses.  Now, with this devious little device in place, I was pulled back without any chance of slipping out.  It was a strange feeling being unable to get hard.  Oh, I grew and swelled, but there just wasn’t enough room for me to get truly hard.  Tasha wanted me to wear it all day and commit to not playing with myself as a man.  I didn’t understand until she showed me my next purchase.  I’d have never in a million years guessed that running a vibrating dildo against my pulled back and trapped semi hard penis could elicit such a strong orgasm.  It took a lot more effort to get off this way.  Getting aroused wasn’t a problem as I was constantly in a state of arousal, but getting aroused enough to cum was work.  I ended up taking on the positioning I assumed women used to masturbate most of the time, laying back in bed with my legs spread wide and the vibrator rubbing up against my pulled back manhood.  I even found that the vibrations were particularly good right up against my anus. 

 Tasha’s laughter, as I described my trials at masturbating as Caitlyn, was rough but not cruel.  She even made some suggestions.  In our relationship, however, they weren’t suggestions.  They were orders.  Finding a butt plug was easy enough and purchased from the same company that made my pink vibrator.  The falsie nubs were harder as they were a specialty product.  When I found them and ordered them I was a little taken aback by the cost, but when I first used them I could fully understand.  These went between my falsies and my nipples.  When glued into place, I couldn’t actually stop them from working if I wanted.  They had little ball bearings on them as well as tiny little teeth.  With pressure on my breasts, they’d push into my nipples sending magical sensations all over my body.  Soon, masturbating was me in the same position but with a jeweled butt plug to vibrate against and my free hand cupping and squeezing my C cup breasts. 

 It still took me work to get off, but Tasha said that made sense.  Women needed more stimulation than men and this meant I was really cumming like a woman.  That comment made me feel both so very small and so very proud.  It was around this time that Tasha’s tasks for me changed slightly.  She was still feminizing me in ways I couldn’t have previously imagined, but it was less pinky pink girly girl sexy, and more sophisticated cosmopolitan seductive.  I didn’t question it and just assumed we were moving on from my personal flavor of fantasy and more onto Tasha’s.  Around this same time travel restrictions were being lifted and more places were opening up.  That’s when Tasha’s offer came.  She was ready to travel herself and wanted to come over and see me in person. 

 I know I should have given it thought.  What would it mean to meet her in person?  What was she planning?  Would this become the lesbian fantasy I’d always wanted but was afraid to ask for?  But my reply of “Yes, anytime you want!” was sent before those thoughts even entered my head.  Tasha made plans around some business of hers but said that I would be kept occupied for the entire trip.  My head spun as I tried to imagine what this wonderful woman had in mind. 

 On the appointed day I was all kinds of nervous.  I had my new gaff in place that unless looked at closely, looked just like a real pussy.  I had my breast forms in place and the edges meticulously smoothed over with the makeup I’d bought just for that purpose.  I went to the stylist I’d met online and got my hair done up just the way Tasha wanted it.  And I wore the lingerie she said would match the fantasy perfectly.  A gothic fitting one piece Edwardian corset bustier with attached stockings and matching semi-opaque satin gloves.   My makeup was perfect with an emphasis on my lips as Tasha had specifically requested.  The last thing to do was to snap the photo, send it to Tasha who was hopefully at the airport, and wait. 

 30 minutes later there was a knock on the door.  I rushed to the door, my heels both clicking loudly on the hardwood floor and making my breasts bounce and shake and jiggle.  Looking through the peep hole showed me Tasha’s beautiful blond hair and blue eyes so I opened the door with a huge smile.  A huge smile that immediately froze on my lips as my throat closed off.  Tasha was as gorgeous as her photos and video chats showed.  She was dressed professionally in a smart looking business suit and sensible blue heels.  She had her luggage with her, but it was being carried by a six foot four guy that looked like a combination body-builder and linebacker. 

 Tasha acted like I wasn’t completely freaked out and came in to hug me and give me a kiss on the cheek.  A she walked past the guy sauntered in like he owned the place, looking me up and down like a piece of meet at the butcher shop.  Turning I tried to think of what to say but Tasha started in, making my stomach drop with almost every word.  “Caitlyn, it’s so good to see you again.  Thank you again for letting us stay with you.  Ajax and I will only be in town for the long weekend, but I promised him that you were looking forward to continuing your lessons with him instead of those toys.”

 My mouth finally opened, but nothing came out except for an embarrassingly girly “eep” when Ajax turned me around and looked down at me.  “Tasha’s been sharing all the videos and photos of you, and I have to say you’ve turned out great.  Who’d have known that you were some wall flower tom boy in school and she made you over into this all through online.  I can’t wait to tell Jason that you’re as sexy as you sound on the phone.  He’s the guy that keeps giving you work and that won’t stop flirting with you.”

 Ajax’s hand moved down my arm as he approached me until he moved it to cup my ass.  With a jerk he puled me in and without asking or any preamble pulled me in for a kiss.  When he tried to stick his tongue not my mouth I got some semblance of my mind back and tried to pull away but he just cupped the back of his hand and pulled me closer.  Embarrassingly I moaned this time when his tongue slipped past my lips.  The moan was from him pulling me close enough to press my breasts and start the little nipple toys nipping and spinning.  By the time Ajax allowed me to pull away he was still holding me and smiling down at me with a confident, cocky, happy grin.  “Damn, I guess Tasha was right.  You really are naturally submissive.  Keep it up Caity, I like that in a girl”

 With his hand giving my nearly bare ass a firm open palm spank and my resulting yelp, I saw Tasha moving toward the door.  Her grin was a mystery as I honestly couldn’t tell if this was some kind of huge joke, or she really was trying to set me up with her boyfriend.  Her words, however, left little to the imagination.  “Now Caitlyn, like I told you in the beginning, all girls should have this kind of experience.  Just try to be as submissive and accommodating to Ajax as you’ve been to me.  Remember your lessons, especially the plug and dildo lessons, and you’ll be fine.  And while I just know you’ll keep in your sub space while I’m gone, know that Ajax is a dom at our local B&D club.  I told him what your safe word was so if he goes to far just say that, and he’ll stop.  Otherwise, he’ll treat you however you want to be treated.  Submit nicely and he’ll give you pleasure you never thought you’d experience.  Struggle and cry and he’ll have you tight up tighter than you ever thought possible.  Whatever you do, I’d highly suggest you follow his commands.  From firsthand experience, I can promise that he loves to spank unruly girls and he doesn’t hold back.”

 I wasn’t prepared for Ajax to act so quickly and found myself lip locked with him again, yelping this time as his probing fingers found my inserted jeweled plug and started to rock it back and forth in my ass.  As the door closed and Tasha left me with this brute, I tried to think past his probing tongue and fingers and figure a way out.  Time unfortunately was shorter than I expected as Ajax broke the kiss and again smiled cockily down at me.  “So, Tasha says you’re a complete virgin to guys, but you’ve been practicing with dildos.  Don’t worry, I know she says you don’t want your pussy used and I’ll respect that limit.  So, what do you want to try with the real thing first?  Suck?  Or fuck?  And don’t worry about which to experience… we have all weekend to get you plenty of both!”

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Another image found on a discord server, and another story that seemed to write itself.  At least the premise was quick.  When I saw the image I saw a guy that had been corresponding with a girl during the pandemic lockdown with a feminization theme.  He went beyond what he thought possible, but she'd found out so much about him that she was able to blackmail him into meeting up with her boyfriend.  

I guess you can tell, I kinda got stuck on the middle 'corresponding' part.  Part way through, I considered back away and writing this out as a longer form story, but it was still right at my fingertips and I figured it would make a good enough Obscura.  

Anyway, hope you like it!