So it looked like before I could do anything on this site, they needed me to take some kind of quiz. Supposedly it was to “personalize the experience”. They were probably just gonna sell the information for ads, but I was drunk and desperate so I went for it.
The first few questions asked for my name, address, phone number, email, that sort of thing. Then the screen went blue for a second, and I freaked out, thinking I’d gotten a virus or something. It went back to normal pretty quickly though, and the website was telling me that I should put in headphones, that it was important to the personality test that I be able to hear the instructions. I didn’t get why they couldn’t just put them up on the screen, but whatever I guess. Annoyingly, whatever caused the crash seemed to be making my screen flicker randomly.
I put my headphones in, and lay back down in my bed, with my laptop resting on top of me. There was a sort of pleasant music being played, something cheerful and upbeat without being annoying. It had a bounce to it, and I started moving my head in time with the beat. Once I had the headphones in, the website started playing a slideshow, with pictures and questions, and a woman’s voice read them out to me as they appeared onscreen. Most of them were pretty innocuous, asking the usual psychobabble bullshit. After a minute or so of passively answering these questions, bopping my head to the beat and getting ticked off at my flickering screen, I sat bolt upright in bed.
The question on the screen was “On a scale from 0 to 5, how much do you want to suck cock?”, with a picture of a giant dick staring me in the face underneath it. The voice sounded very suggestive when she asked me the question, almost as if she wanted me to say 5.
I’m not gay or anything. I’ve never even thought about a dude in that way, so clicked 0. Big red words immediately popped up, saying, “ONLY CHOOSE 0 IF YOU HAVE NEVER WANTED TO SUCK COCK EVEN A LITTLE BIT. HONESTY IS IMPORTANT. ARE YOU SURE?”.
I stopped to consider that for a second. Was I sure? I thought so, but honesty was important and I didn’t want to lie on the personality test if it could possibly screw up the plan to make Elena fall in love with me. I looked at the dick on the screen, so huge, so hard, with a bead of precum dripping from the tip. I didn’t want to suck it, but I guess I could see how someone might. It had a presence to it, and I couldn’t take my eyes away. I clicked 1, just to be safe, and pink letters saying, “GOOD GIRL” popped up next to a big smiley face. It was kinda cute, so I smiled back at my computer.
I got into a groove answering the rest of the questions, even managing to ignore the flickering which got more and more frequent as the test went on, and I lost track of time. The next time I looked up at my clock, it was nearing 5 am. Thankfully, it seemed like I was almost done with the personality test. I only had to input my physical details. It was kind of embarrassing, revealing so much about myself to a computer, but it was important to be honest.
I told it that I’m 5’ 7”, with shoulder length brown hair I keep pulled back and green eyes that get me places with the girls. Well, most girls. Elena didn’t seem to notice. It asked me to rate myself from 0-10, with 0 being masculine and 10 being feminine, and I chose 4. I’m not the manliest guy, and it’s important to be honest. For my best feature, I wrote my great ass (that’s the thing I’ve gotten the most compliments on at least, from girls and guys alike), and filled in the details on my dick. Why it’s important that I’m circumcised or what size my dick is, I had no idea but I had to fill it in to move on. I eyeballed my pants, and plugged in 6” at a rough guess. It might be a bit optimistic, and when I hit continue and a big red “ARE YOU SURE? IT’S IMPORTANT TO BE HONEST” popped up on the screen, I went back and switched it to 5”. I hit continue and the popup didn’t come back. Instead, the screen faded to a soft green tone.
Finally it was done. The music slowed, and I realized it had been going insanely fast for the entire quiz. It changed tone, becoming more peppy than it had been, and the website shifted to display:
“STEP 1: FEMININE FASHION. Before you start doing anything drastic, the first step is to see if you can make yourself a bit more androgynous in appearance. If your lady-love already has feelings for you and is just held back by your manly appearance, a little bit of makeup and some clothes could be the push she needs to fall into your arms. Now, let’s choose your style!”
The laptop went blue for a moment, and I waited patiently for it to come back, which it did after a few seconds, although with the same damned flicker as before. The words on the screen now said, “Rate these fashion looks from 1 to 5, based on how much you like them. Just say the number, and the microphone on your computer will pick it up. Don’t worry about how they’d look on you, we’ll personalize your style based on your body and your preferences once you’ve finished STEP 1!”
It started to flicker faster now, and with each flicker a picture of a beautiful woman showed up. I didn’t even think before I said the number, and then the picture was gone and another one showed up.
Flicker. A brunette in a tight-fitting sweater and jeans. 2
Flicker. A redhead in a light blue sundress. 3
Flicker. Another redhead, in jean shorts and a light pink crop top. 4
Flicker. A blonde in black lingerie, staring seductively at the screen. 5
Flicker. The same blonde, bent over on a bed getting fucked hard from behind. 5
Flicker. A different blonde, in very skinny jeans and a cute pink t-shirt. 2
Flicker. The brunette, flashing her tits at the camera with an impish grin. 5
Flicker. Faster now, I can’t even see what’s going on, I just say the number that pops into my head. 1
Flicker. Flicker. Flicker. Flicker.
I don’t know how long it lasted, or what pictures I was seeing, but it was fun. I was looking at beautiful women, listening to some fun music, and I didn’t even have to think. I just said whatever came into my head, without worrying about whether or not I was right. I was being honest, and honesty is important. I was a good girl.
I’m not sure where that came from. But it felt right. I was trying to make myself more like a girl so Elena would be into me, so when I was doing what the website was telling me, I was being a good girl. That makes sense.
Eventually the pictures ended. The sudden stop startled me out of my reverie, and I refocused my eyes and thoughts on the screen. The words
“We’ve worked out what your personal Feminine Fashion should be! Are you ready to get started?”
appeared on-screen. Below them was a big green button labeled YES! There was no NO button that I could find. I couldn’t think of any reason I’d want one though. Of course I was ready to get started. I clicked the yes button, and the music in my ear changed yet again, still upbeat but now with a deep bass throb that pulsed into my skull.
A picture slowly faded into view. It was… me. But I looked like a girl. Or, not quite a girl. It was on the feminine side of androgynous, but it was still androgynous. Still, whatever it was, I looked fucking hot. Sure I didn’t have boobs or anything, but the tight baby blue tank top I was wearing emphasized what curves I did have, showing off my slim frame rather than covering it up. And the jeans I was wearing in the picture were so tight they could’ve been painted on. But the biggest change was my face. It was still my face, but it was beautiful. It was done up so subtly that if I hadn’t known what I should look like, I would have thought this was just a gorgeous woman, with all the hard lines of my jaw smoothed away and my lips and eyes emphasized with bright lipstick and sharp curves of eyeliner. And the look on my face. It was a sexy, sultry smile, turned up at one corner with my eyes saying, “Yeah, I know you want me. Come and get me if you’ve got the guts”. I could feel my pants stiffening just looking at it.
Another picture slowly faded in next to the first, the same outfit but from the back this time. From this angle, you couldn’t tell that I wasn’t born a girl in a million years. The top followed the curves of my torso, suggesting the swell of breasts that were just out of view. My hair was lightly curled, and tumbled down my back in a cascade. And my ass in those painted on jeans was a work of art. My hand unconsciously slid down, undid my zipper, and wrapped around my cock.
Next to the pictures, words faded in:
“This is the first phase in your Feminine Fashion! Today, you’re going to go out and buy these clothes. The next page has a list of stores near you where you can pick them up. Tomorrow you’ll have a new Fashion step, and you’ll also unlock Step 2 to seeing things from Her Point of View! For now, take as much time as you want to enjoy the view. Remember, this is you now! Whenever you’re ready, just say continue into your microphone”
I barely even read the words, just skimming through, but one phrase stuck with me. “This is you now”. I hadn’t thought about it like that before. I was committing to completely changing my wardrobe and how I look just for some girl? Wasn’t that like number one on the don’t list for relationships? Okay maybe not the number one red flag, but “Be yourself” was definitely the top piece of dating advice I’d ever heard.
Although, I guess this was just being myself. I was in love with Elena, so it only made sense. And besides, I looked fucking amazing. I couldn’t wait to go out and buy those clothes, feel them pressed up tight against my skin, look so fucking sexy…
I realized that throughout my inner monologue, I’d been stroking my cock, faster and faster, keeping time with the slowly accelerating bass beat. It only broke me out of my reverie because it was starting to feel so good I couldn’t ignore it any longer. I couldn’t think of anything else besides how amazing it felt to be jacking off, touching myself while looking at pictures of how fucking sexy I looked in girl clothes. As the music in my ears got faster and faster, and the bass pounded harder and harder, I started to pant with the exertion, struggling to keep up. But it was as if my hand was outside my control. No matter how tired I got, I kept stroking in time with the beat, faster and faster until finally I glanced up at the sultry smile on my face and just as the song grew to its final crescendo, I came, spraying jizz all over my hands, my clothes, my computer screen.
A little even got onto my face. I absentmindedly licked at it while I wiped the computer off. Not bad tasting actually. I whispered to myself as I cleaned “This is me now”, and the screen changed to show a big yellow smiley face on a pink background, saying
“Congratulations! You’re starting to see things from Her Point of View! You are now ready to progress!”
* * *
After my explosive orgasm, I spent a while just listening to the music, which had calmed down from the pulsing bass beat back to a more relaxing tune. I don’t normally go in for this kind of slow stuff, but this was actually so good I couldn’t help but close my eyes and bliss out for a bit. I had been up all night after all.
A few minutes later, the song came to an end and switched back to one of the upbeat pop songs from earlier, and I opened my eyes. The smiley face was gone, replaced by a map of my neighborhood with directions to the nearest mall, along with a short shopping list. The listed prices made my eyes bug out for a second, but I remembered how amazing I looked in that picture, and if these clothes could make me look like that, it was worth blowing some of my rainy day money.
The map said that the mall didn’t open until 10. It was only about ten minutes away, which meant I had about four hours to get some sleep, shower, and eat before my expedition. Not that bad. I’ve had worse after a night of drinking with James and Alex.
Suddenly completely exhausted, I collapsed on my bed, not even bothering to take off my clothes, set an alarm, or turn off my laptop. I drifted off to sleep while the music played softly in my ears.
I jolted awake what seemed like only seconds later, but a quick glance at my clock told me it was 9:30. I could barely recollect some very strange dreams, but as I tried to grasp them they slipped away. It almost felt like someone had told me to wake up, but the music in my ears had stopped sometime while I was asleep, and besides there weren’t any lyrics in anything that had been played so far.
Pulling myself out of bed, I stumbled into the shower, stumbled back out a few minutes later, ate some cereal as fast as possible, pulled on a pair of old jeans and a t-shirt, and was out the door at 9:45 exactly. I had some shopping to do.
The mall wasn’t quite open yet when I arrived, so I took some time to read over the shopping list again. 1 baby blue tank top, 1 pair ridiculously expensive and tight jeans, and an assortment of makeup products. It didn’t seem like a lot, but from what I remembered of last night, or rather this morning, I’d get more fashion instructions tomorrow, when I unlocked the next section. Also on the shopping list was “Variety of panties, your choice. Optional,” and I didn’t know quite what to make of that. If it was optional, why was it on there? And did they expect me to pick the panties out myself? Wasn’t the whole point of this to have the site decide for me? I decided I’d just ignore the panties for now. It’s not as though I was cross-dressing for fun here. I was doing this so I’d look enough like a girl that Elena would realize what she was missing and fall for me. Right?
Finally, the doors opened and I made my way inside. It was huge, and overwhelming, and I was the only person in the store. I guessed that since this was near my college, most of their usual customer base was still sleeping off last night’s hangovers. A sales girl came up to me, gave me a bit of a confused look, and said, “Can I help you with anything sir?”
“Uh, no just browsing, I’m okay, thank you. Sorry”. Wow. Way to go Ash, I thought to myself. Trying to win the affection of your lady-love, and you’re stumbling all over yourself because the girl who works at the mall is cute.
“Alright, well if you ever need anything just let me know,” she said with a wink at me, and turned to go. I caught myself watching her ass sway as she walked and pulled my eyes away. She was really cute though. Blue black hair in a pixie cut, with these incredible piercing green eyes, and the body of a dancer, slender and lithe. Not too long ago, I would have been all over that, or rather I would have tried to be all over that. But now, I was a man on a mission. And that mission involved me being in the women’s section of a department store by myself at 10 am on a Saturday. Nothing weird about that at all.
I wandered around the store aimlessly, trying to look as though I was doing anything but shopping for girls’ clothes, while I slowly worked up the courage to make my way towards the jeans on my list. I figured I’d start with those, since it’s not like I’d be the only guy to wear women’s jeans. They’re just like, super skinny jeans right? It’s not that weird. I’m not that weird
With that mantra repeating in my head, I wandered into the women’s jeans section, found the pair that had been indicated on my list, and walked away quickly. After some more wandering, and peeking to make sure that the green-eyed girl wasn’t looking in my direction, I quickly ducked back into the women’s section, and grabbed the baby blue top. With my clothes in hand, I bolted to the self-service register, thanking my lucky stars I didn’t have to explain my fashion choices to a judgmental cashier.
Right before I got to the counter, I was struck with a thought. I had to try these on before I bought them, right? I mean, I gave the website my measurements, but even I know that the measurements on women’s clothing are different brand to brand. And I really didn’t want to have to come back and return these later.
So I pivoted, trying to make it seem as natural as possible. I didn’t do a very good job seeing as I was at the front of the store next to the registers and the dressing rooms were all the way at the back, but I had to try and preserve some of my dignity.
Again making sure no one was watching, I snuck my way into one of the dressing rooms and out of sight from the hordes of curious observers I’d imagined were glaring at me as I shopped. Granted, the store was completely empty besides the sales girl, but I couldn’t shake the feeling that I was doing something almost obscene and that I ought to feel guilty for it.
“Fuck that,” I muttered to myself “I’m a grown man, and I can make my own clothing choices. They don’t have the right to judge me.”
And with that self-righteous indignation held firmly in my mind to keep away the lingering sense of embarrassment, I changed into the jeans and the baby blue tank top. It took me a bit longer than I was expecting. Those pants were really, really tight.
Finally it was done. I looked up at the mirror, getting my first glimpse of “the new me”. I looked… good. The top clung to me, both outlining my body in perfect detail and suggesting curves that didn’t quite exist on second glance. It flared out a little at the bottom to give the impression of hips. The jeans were the tightest things I’d ever worn, almost like a second skin. They made my legs look more shapely, more feminine, and drew the eye slowly up towards my ass.
My ass was, as always, my best feature. Tight and well-rounded at the best of times, the jeans flowed around the curves of my cheeks, revealing everything and yet leaving it all to the imagination.
I was hot. I looked good. Great even. But I still looked like a guy. Kind of a gay guy honestly, not to buy into stereotypes or anything. My face was still sharp and masculine, with a touch of beard shadow showing even though I had shaved just this morning. And now I knew why they’d recommended panties. My boxers were bunched up underneath the jeans, and some ugly wrinkles showed through the thin fabric. Still though, pretty good for a first outing and without even buying the makeup yet.
If I was going to do this, I needed to do it right. I walked quickly and confidently out of the dressing room, and strode to the lingerie section. Only once I was already out in the open did I realize that I was still wearing the jeans and top. I also realized that I wasn’t the only person in the store anymore. This time, people were staring.
My face burning with shame, I grabbed the closest pair of panties and ran back into the changing room.
Alone once more, the embarrassment began to fade and as I calmed down, I realized what I was holding; a pair of delicate white lace panties. They were gorgeous, sexy and slutty and innocent all at once. I couldn’t take my eyes away. I could hear somewhere in the back of my head the pulse of the deep bass beat from the night before. Almost like I was in a trance, I peeled the jeans off, pulled down my boxers, and slid the panties up my leg, slowly, savoring the feeling of the soft fabric against my skin. I let out a quiet gasp as I reached my dick, the sensitive area reacting to the soft lace by sending waves of pleasure up my spine. My dick started to harden, pushing against the fabric that now covered it completely. The bass grew louder in my ears, and I reached my hand down slowly, sliding it underneath the panties and—
“Mind if I join you?” an amused voice asked. I whirled around, hand still tucked into the panties, and saw the face of the green-eyed sales girl peeking through the door of the changing room. I blushed a bright red, yanked my hand out, and started to stammer an apology.
“Hey no don’t worry,” she said, grinning slightly “I’m not here to get you in trouble. You looked pretty worried out there and I was coming to check and see if you were okay. I knocked, but you didn’t respond.”
“Oh god I am so sorry,” I replied, utterly mortified, “I don’t know how I missed that.”
“Well, looks like you were a little preoccupied,” she said with a meaningful glance at my panty covered cock.
“I’m so so so sorry. I don’t normally do this, I swear. I don’t know what came over me.”
“I’m just sorry I interrupted you. It looked like I was about to get a bit of a show,” she said with a wink.
I didn’t know how to respond to that at all, so I just stammered, and blushed even harder.
“Don’t worry about it,” she said, her tone shifting from amused to sympathetic. “People are assholes. Don’t pay them any attention. You’re trans, right?”
I looked at her dumbfounded, my mouth hanging open.
“Oh my god, I haven’t even asked your name yet and I’m already getting into things that are probably super personal and you don’t have to talk about them at all if you don’t want to. I just saw how scared you were and thought you could use someone friendly to talk to. I’m Jenna, by the way.”
Still utterly flabbergasted at the way this conversation was going, I managed to stutter out “A-Ashley.” Where the hell had that come from? I hadn’t gone by Ashley since I was in kindergarten.
Jenna smiled at me, and I forgot my embarrassment for a moment. It was that kind of smile. “Nice to meet you Ashley,” she said. She moved closer to me, so that there were only inches of distance between us. My still-hard cock was a breath away from touching her. She looked down at it, then back up at me. Her smile turned wicked, and she said, “Mind if I continue where you left off?”
“Um, what?” I replied, then kicked myself.
“Listen Ashley, I think you’re cute. I think I’d like to get to know you a little better. And I think that since you’re already so hard…” she said this last as her hand brushed the tip of my dick through my panties, and I gasped again. That only made her smile more. “It would be a shame to let this opportunity go to waste. Now, I can tell you’re feeling a little awkward about this whole situation. So how about this: If you’re okay with this, you don’t have to do or say anything. If not, all you have to do is shake your head. What do you think?”
The bass beat was back, crowding out my thoughts. I stood there staring, not moving a muscle.
Jenna’s smile grew even larger, and she pushed me back against the changing-room bench, and slowly lowered herself to her knees. “That’s a good girl,” she said, and a wave of electricity swept through my body.
Slowly, maddeningly slowly, Jenna stroked one finger over my straining cock, letting out a little giggle as it twitched in response to her touch. She slid her finger all the way down to the base of my shaft and then slowly back up to the head. There was a small bead of precum leaking through the panties and she scooped it up and looked me in the eyes as she brought her finger up to her mouth and began to suck.
“I like how you taste,” Jenna said, her voice rough with desire. “I think I’ll have to taste you some more.” And with that she closed the distance between us, holding my arms down onto the bench, and licked up the length of my cock, her tongue caressing me through my panties and just brushing the tip that peeked out over the lace.
I gasped. I couldn’t help it. It was better than anything I’d ever felt before. Just that one lick was better than every fuck I’d had in my entire life. I didn’t know what was going on. It just all felt so good, and the bass beat that was pulsing in my ears made it hard to think. It was definitely there this time, not just a memory. I wondered how I was still hearing it when I definitely wasn’t wearing my earbuds or anywhere near my computer, but my train of thought was interrupted by Jenna peeling back my panties, and wrapping her warm, soft lips around the head of my cock.
I let out a high slow moan, and didn’t have the brainpower left to think about how strange that was. Jenna pulled herself off me long enough to say, “You’re being a very good girl,” which sent out another wave of pleasure that swept up from my cock through my whole body. When it reached the bass beat in my ears, it resonated with the music and became instantly twice as intense. This time, it moved slowly down, washing over me in a wave.
Jenna, as though she could see the pleasure sweeping across my body, reached up without taking her mouth off my dick and pinched my right nipple with one hand right as the wave reached my chest. My vision went white for a second, as what felt like fireworks exploded in my nipple.
I must have moaned loudly, cause Jenna shifted up to cover my mouth with her hand. I hadn’t realized. The pleasure was too much. I didn’t know what was going on, this whole thing was feeling too fucking amazing. Jenna slipped one of her fingers into my mouth, and I began to suck on it unconsciously, operating entirely on instinct at this point.
She moved back down, wrapping her tongue around my cock and teasing me relentlessly. Precum was dripping from the tip and Jenna lapped it up eagerly. I bucked my hips against her mouth, desperate to cum.
Jenna pulled away her finger, and I let out a soft whimper, my mouth suddenly left empty. She let it drag slowly down my chest, circling my nipples and triggering another moan from me. I was like an animal, responding to her physical touch and willing to do whatever I had to do to make sure Jenna kept touching me.
She looked up at me, a wicked glint in her eyes as her saliva-covered finger finally made its way down to my cock. Jenna stroked the tip, gathering some of the precum that still poured from it, and suddenly and without warning slipped her hand between my legs and slid her finger up and into my ass.
I cannot describe how good it felt. I’d never done anything around that area before, but suddenly I was bucking against her hand, trying to fuck myself on her finger, just to get more of that indescribable bliss. Jenna slid her finger in and out a few times, driving me wilder with every thrust, and then curled it inwards pressing up against what had to be my prostate.
I cried out and came like I had never cum before, my vision going black for what felt like minutes, my mind on fire with pleasure, shooting ropes of cum all over Jenna’s face and into her open mouth.
* * *
Some time later when my heart finally stopped pounding and my vision cleared, I opened my eyes. Jenna was smiling at me in a self-satisfied sort of way, a long strand of my jizz still on her face.
“I gotta say Ashley, you’re damn good for a girl’s self-esteem. It’s been a long time since I’ve made someone cum that hard from just a blowjob,” she said.
“That was. Wow. I mean. It was amazing. I can’t believe that just happened,” I stammered out, suddenly realizing that I’d just cum all over both a beautiful girl and a public changing room.
She giggled a bit at that and said, “Unfortunately I have to run now. I’m technically still on the clock, and if I’m gone for much longer my idiot boss might actually realize I’ve been missing.”
I looked crestfallen at that which made her giggle harder. “Oh sweetheart,” she said, “that pouty face you’re making is really adorable. Listen, while you were recovering I put my number in your phone. Give me a call sometime.”
I smiled at her, relieved, and Jenna leaned in and kissed me soft and deep. I could still taste my cum on her lips. “Now I really do have to run,” she said. “You probably shouldn’t try and buy panties that soaked, so I’ll show you out the back way. I’m sure we can find a way for you to repay me next time.” She looked at me lasciviously and gave me a wink before devolving into another fit of laughter.
Jenna led me out through a door marked “Employees Only”. I followed her, content to passively obey, and once we made it to the alleyway behind the store she kissed me goodbye and rushed back inside.
“Hopefully she remembers to clean off that cum before she goes back into the mall,” I thought to myself, and grinned.
And then it all hit me. I’d just tried on women’s clothes, started jacking it in panties, gotten the best blowjob of my life, cum from a girl’s finger in my ass, and somehow shoplifted a complete outfit, all before noon. Somehow, with the phantom music playing through my earbuds that weren’t there, it didn’t seem all that abnormal. I could get used to this.
So it looked like before I could do anything on this site, they needed me to take some kind of quiz. Supposedly it was to “personalize the experience”. They were probably just gonna sell the information for ads, but I was drunk and desperate so I went for it.