Finding the Perfect Fit Pt. 25

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It didn't take long before Pandora was leaning forward, pushing back into me with greater force and I returned the vigor she was showing me. I slipped my hands back down her figure and took hold of her hips which the dress showed off to the fullest extent. As the music played on, I started to pound Pandora and her breathing was picking up, the song almost drowning out the rustles of the skirts but not the growing noise of our bodies meeting each other. There was no penetration but right then, I wanted her so bad I didn't noticed. I reached around the front and tried to find Pandora's crotch where I knew she was going to want attention. Instead she caught my hand and held it.

"No..." She panted and I took the hint, still taking great pleasure in humping Pandora, the song driving me higher and higher. Pandora's growing moans were helping as well and I was losing control. Her pink and purple hair was swaying along and the glimpses of her absolutely adorable face only excited me further.

"Gen!" She gasped and I only answered by continuing my motions, knowing what she wanted. "Gen!" Pandora called out and my only answer was a panting growl. Her cries lost all cohesion, simply expressing passion and pleasure as I kept going, having found a pace that couldn't be sustained but would get the job done.

With a wavering cry, Pandora flung her head back and leaned back into me, nearly knocking the both of us over. I caught her and held my love as she panted, slumping down as if her legs weren't quite up to the task of carrying her weight.

"Oh Gen..." She said and I led us to the bed, keeping Pandora on my lap as her breathing slowed. Eventually she turned around and we kissed, taking our time and going slow. Pandora's face was flushed and she settled for snuggling up to me as we both laid back and listened to the song play on and on.

"Thank you." She said and I kissed her on the cheek before replying.

"It's not like doing that is work. I enjoy it too." I said as Pandora grabbed at her phone and sighed at seeing the time.

"I... Yeah, I enjoy it too." She said before standing. "I love wearing this and feeling all girly with you." She grinned before blinking and there was something else, a touch of sadness that caught me off guard. "I hope I never stop feeling this way." I stood and approached her, seeing that sudden touch of sorrow melt off of Pandora's face.

"Same here." I said, pulling her close and feeling protective and sad, as if the emotion was catching or something. "Because I love Jamie. And Pandora. And as long as you're here with me, I'll love whoever you are. Or become." I said and she hugged me close and we stood there until an alarm went off, leading me to help Pandora get out of the dress and soiled panties then into her work clothes. Laughing, we ran out to my car and I fired it up, not bothering to turn on the AC and instead driving fast so she wouldn't be late. The windows were down and our hair was blowing all over the place in the hot wind of the summer day.

There was no sadness or actively trying to be sexy on Pandora's face as I dropped her off at Dairy Queen but just happiness at living her life with me. She leaned up and gave me a quick kiss before hopping out of the car and I watched her go into restaurant, a growing pride that I'd giving that booty what it wanted not ten minutes ago. The drive back was slower but had the radio turned up loud before arriving back home and pulling out the laptop.

So there it is. And now I get to wait until tomorrow night. And it's going to be a long day. Still not sure how it's going to play out but... I've got nothing else to add there. I don't like leaving this entry off so unsure and blah but what else can I say? All I can think about is sharing my Jamie-Pandora with someone else and that's not an easy thing to even think about, much less do.

Fuck. Just... Fuck.

August 9

Jamie worked the morning shift Sunday while I worried for a full eight hours. It wasn't a great time but I picked him up once he was done there and drove back home, not talking very much during the short drive. He showered and I started looking for something to watch to pass the time as by that point I wasn't think about much of anything but just consumed with worry and doubt. Damp and warm, Jamie joined me on the couch, cuddling up and giving suggestions before I finally pushed play on Groundhog Day, one of my Dad's favorites.

Once it was over we continued to sit there as Ghostbusters began to play, not paying it too much mind.

"How are you feeling about tonight?" Jamie finally asked and I took my time replying.

"Unsure? Nika said she's a recovering asshole and that strikes me as being potentially problematic." And that wasn't even the worst part, as seeing Jamie-Pandora with someone else might just make me snap and burn it all down. And all of that was on top of Syliva's house feeling like the set to a slasher movie. "What bout you?"

"Nervous." His answer was straight to the point and I didn't push it. Nika had made it clear we were going to talk once we got there so fretting was useless. Yet I kept doing it because of course I did. Eventually the light stopped flowing through the blinds so strongly and Jamie suggested we get ready.

I wasn't sure how to feel but getting dressed was something of a relief. It was something to do and there was a clear goal to look good. And I got a nice little surprise when Jamie pulled the little black dress out of the closet and paired it with the push up bra, stockings and garter belt. I went much simpler, going for the short skirt Jamie had favored during our first semester of fooling around with a low cut shirt. Jamie looked ready for a higher class restaurant while I might have been ready to hit the clubs, assuming that urge ever touched me. And he smiled at seeing me, head tilting to the side and I felt adoration for Jamie-Pandora right then.

Wrapping an arm about her waist, we walked to the bathroom and did our makeup side by side, my red lips smiling at seeing Jamie-Pandora oh so carefully do their eyeliner. And there was so much happiness at getting it right the first time. Once we were done the celebratory kiss was simple and quick, not wanting to mess up anything we'd just done.

"Ya looking fuckin' fine." Jamie-Pandora blushed and smiled, looking me up and down with clear interest as well.

"Your one to talk. But let's get going, I don't want to be late or... Lose this mood? I want this to be fun cause that's the point, right?" Jamie-Pandora's color was very high and I wrapped an arm about those bare shoulders as we walked into the living room. Dressed up like this, it feels wrong to just use Jamie to sum up the person I was with but Pandora wasn't fully out yet. So Jamie-Pandora it is, more fluid in gender and interests.

"Ya right, it should be a good time as long as we each understand that." I said, more for my benefit than theirs. Neither of us had footwear that matched the little black dress Jamie-Pandora was wearing so a simple pair of my sandals had to do. It wasn't like they were going to be on for very long.

We walked out in the gloom of a summer that didn't know it was dying, Jamie-Pandora with their shoulders rolled back and boobs presented for the world to see. Getting in my car, Jamie-Pandora took charge of the radio while I started driving, heart fluttering but I wasn't going to say anything yet. There was no telling what might happen and while me writing this knows it all, that past Gen had no idea.

"Jesus, you weren't kidding." Jamie said in his guy voice as I turned into the rich section of town, looking out the window at the large, mostly dark houses.

"So it's not just me then, right? It feels weird here?" I said, demanding an answer with my tone and Jamie just gave me a flat stare.

"Gen, I'm in a dress that barely covers anything and tonight's topic of conversation is sex. The Headless Horseman could pass us and I'd think that's perfectly normal!" That did make me giggle, helping to cut the tension as I once more pulled up before the gate. "What the fuck? There's a gate?!" And when it opened all on it's own, Jamie leaned farther back in his seat, suddenly not looking sure of this at all.

"If we get attacked by a murderer, run and I'll fight it off." I said, half serious and half joking.

"My hero." Jamie-Pandora said, the voice going lighter even as it dripped with sarcasm and I laughed while driving down the long way. I parked before the two car garage and got out, Jamie-Pandora joining me and waiting until I was by their side to walk to the front door.

A single knock on the heavy door was all it took for Nika to answer. She was in a short dress that was much like Jamie's, except hers' was white with slits up the side of the skirt and had straps crossing over her breasts that did little to hide them. Her hair was a shimmering black that cascaded down in a mess of sexy curls that caught and played with the light as we observed each other for a few silent seconds.

"Come in!" With that, Nika stood aside and we did just that, sitting together on the couch as Nika sat on a footrest before us, checking Jamie out before facing me. "Sure about this? Cause you don't look like it."

"I'm ready to talk first." I said slowly and Nika nodded, turning to Jamie.

"And damn, look at you!" Jamie flushed red at that, his hand squeezing mine. "But let's get to know each other first. So here's the first issue: I've done something like this before with a couple and it blew up. Bad. That time, I didn't ask too many questions cause I figured, 'hey, they're adults who can handle a third wheel when it comes to sex.' And no, they couldn't! So we're going to talk it over until I'm sure this is going to work without exploding your relationship." I flinched at that, suddenly understanding why Nika wanted to meet me first, then Jamie.

"Sure, what do you need to know?" Jamie said in his girly voice, getting Nika's full attention.

"Well, I'm going to need to know about you." Planting an elbow on a knee, Nika rested her chin on a first while gazing at Jamie. "Gen said that your exploring your gender identity. Tell me about that."

"Sure but I want to hear about you as well. I... Might have a few questions of my own." Nika paused at hearing that but nodded as Jamie took a deep breath before starting in on his story, abet in the femme voice. He told about growing boobs while in school, hiding away and finally striking out on his own during college then meeting me.

"That's when I first started exploring gender and who I was, mostly out of necessity. I had a crisis of sorts via bra." Nika laughed at that, Jamie pausing in telling the story even as I found her amusement to be in bad taste.

"Whew! That's a new one!" Nika wiped her eyes but quieted down quickly, motioning for Jamie to carry on. He did so, talking about getting the boob crème and pills to make sure he couldn't hide away and finding he liked both the changes and the process of getting there.

"Ah, that I understand!" That's when another thing came into focus for me: Jamie and Nika had that in common, changing towards some goal. "So how does that lead you to wanting to give head?"

"Well, Gen got a strap on at some point and I found I liked that. And sure, I could suck on it but it's probably not the same as the real thing, right? After my boobs started growing again, I wanted to see what embracing being a woman would be like. I've been kind of, sort of male all my life but not a guy, you know?" Nika finally broke from her usual pose and leaned forward, eyes shining, fully invested in what my love had to say. "I'd just... Existed. Not a dude but too scared to even think of trying to be more female even thought I already had the boobs for it. And there's not much about being a guy I'm interested in! So why not see what the other half had to offer?" Jamie blinked back to reality, having retreated inward during his talk.

"I totally understand." Reaching out, Nika tapped Jamie on a stocking clad knee once, twice before sitting back. "But you should know that having sex with me wouldn't make you more of a woman. There's plenty of manly men out there who enjoy some hot dicking. Live as a woman if you want but going down on me isn't going to help you make that choice. Hey, maybe your lesbian? Ever think of that?"

"Yes but can I know that for sure without trying the other side?" Jamie said, glancing out of the corner of his eyes at me, face coloring. "I know I love Gen and she's everything I need." I squeezed his hand, touched by his vote of faith.

"Except packing a real dick." Nika looked me up and down before breaking out in a wide, sunny smile. "I should've known you were good with a strap on, I seem to attract that sort." I blinked a few times, having no answer for that. "Sylvia's the same way and I swear she should have been born with one given how good she is with it."

"Right?!" Jamie nearly shouted and Nika laughed with utter glee as I sat there, baffled. "It's like, 'Wow using my dick is fun!' and then Gen shows up with a strap on and makes me feel like I should be taking lessons from her!"

"Not on purpose!" I raise my voice over the din and only to have Jamie fall over on my shoulder laughing. I wasn't sure how to feel as they weren't laughing at me and it was good natured ribbing but I still was the odd woman out. "I just do what comes naturally!"

"Oh, I don't doubt it." Nika said once she could, that wicked grin coming back out once more. "Look, I believe both of you and think, hope, that fooling around with me isn't going to make you split up and get me a stalker." I recoiled and Nika looked like she smelled something foul right under her nose. "Yeah, that's another reason why I stopped leaving the house much. Got cameras and a security system here."

"Wow." And that was all I had to say on the matter as Nika waved the issue away, Jamie finally sobering up at the chance in topic.

"I'm not trying to be an asshole, it just comes naturally, but breaking up happy yet bored couples isn't something I want to do. Or am proud of." She certainly didn't look or sound very happy about it. "But I can't figure out how having boobs wasn't the best thing in the world for you! God, I'm so jealous!" Nika's face was one of envy and I took the chance to mess with her. Slipping halfway behind Jamie, I clasped his breasts in my hands and gave them a squeeze, getting a shocked noise quickly became a throaty moan.

"Jesus wept." And that's all Nika had to say on the matter, her cool gaze replaced with one I completely understood: Want.

"Gen! Not yet!" I retook my place beside him, too happy about shutting Nika up as Jamie adjusted his dress before speaking again. "Anyway! My breasts showed up when I was first starting to realize I had nothing in common with most of the people in my class and they only served to isolate me further."

"Yeah but you had boobs! Fuck 'em!" I nearly choked at Nika's reply, probably due to saying something similar before.

"Boobs aren't good substitutes for people or engaging conversation." Jamie said in a patient tone, still holding strong with the femme voice. Nika just made a fart noise in reply.

"Please, I'm sure I could have a more engaging conversation with your tits than some of the people I went to school with." Even Jamie laughed at that, more out of shock than genuine mirth it seemed. "I didn't even have boobs and I still was alone. At least I would have had something good back then." Nika's voice dipped slightly and she held up a finger, walking away and leaving us together on the couch.

"You weren't kidding. This is weird." Jamie said in a low tone and all I could do was nod. Nika returned in short order with three glasses of water, leading to another moment of silence as we all drank.

"I have a rather personal question Nika and I'm not sure there's any good way to ask it." Jamie said slowly, holding the glass in his hands and looking at the empty hearth.

"Go for it." Nika said before taking another drink as Jamie lined up his thoughts.

"How did you know you were transgender?" Jamie asked and Nika studied the glass of water for a bit before speaking.

"For too long I didn't and that was the problem. I knew something was off but couldn't figure it out, like a car alarm screaming but there's no car around. All I knew is I didn't like looking in the mirror cause it put me in a bad mood so I stopped doing that. But I still knew there were problems." Another drink taken by Nika as I sat there, listening and unable to say much to help. Jamie was hanging on her every word, no surprises there. Hell, I wanted to know as well.

"By the time I got to high school I just figured everybody hated themselves like I did." Nika looked up and suddenly pointed at Jamie, who had flinched back at her words and was looking at the woman with what might have been pity. "You get it! I told that to Sylvia and she didn't, couldn't understand it but you do! You do!" Her words took on a more pleading tone, as if asking for permission to feel that way.

"I did, yeah." Jamie's voice dropped slightly lower, somewhere in between male and female. "I hated myself not just for looking different but not being able to get past that. I wasn't funny or smart where it mattered or had anything that anyone around me wanted. So I hated them all and myself."

"It's fucked up and I know it's fucked up but thank you for saying that." Nika swallowed hard, taking another sip of water before continuing as I felt very out of place. None of this applied to me and yet there I was, listening to two people dressed for sex instead expose their damaged pasts to each other. "But yeah, you know how I felt then. I wished my school would blow up or something, get hit by a meteor just to wipe out all the dipshits and take me out too cause I wasn't any better." A sigh before she resumed.

"I graduate, somehow, and start working. Mostly shitty jobs but I was able to get a shitty apartment and decided that being a shitty virgin was the problem. So I hopped onto some dating sites and failed to find anyone. So that didn't help. Do you know how hard it is to send a flirty message when you want to throw yourself into a meat grinder?" I coughed in response, her bitter question catching me mid-drink. "Yeah, it feels about like that."

"Anyway, I shoot a message to a chick way out of my league who's older than me and college educated, all that shit. She replies and we hit it off. And it's Sylvia. We talk for a while and she finds my jokes funny, which is news to me cause even I don't, they just fall out of my mouth. But finally she picks me up and brings me here." Nika spreads her arms to the walls, making Jamie look around. "She'd just moved in and had a bed, a chair and fuck else. So we banged all night, slept, ate and then got back to it. She figured out pretty quick I hadn't been kidding about the virgin thing but hey, practice makes perfect."

"We start seeing each other on the regular but I don't feel any better. In fact, my self loathing only gets worse. I had this suspicion that I wasn't good at sex while Sylvia was and she had this amazing place and a good paying job while I was being a maid at a fucking hotel. And they didn't even give me a maid outfit!" The outrage in Nika's voice was real or close enough it totally passed.

"I end up getting fired from my job, they were right to do it, and Sylvia says I can come stay with her for a while. So I pack up and ended up crashing here for a week and start going crazy. I hate myself for having no money and no job. I hate Sylvia for keeping me alive and just, being driven. Having goals. I hate all that but most of all I hate myself. I knew I deserved it, knew all the shitty things I'd done but couldn't explain why." Nika sipped at the water, her mood a far cry from the more playful one it had my, my own greatly diminished as well. Yet I was still curious. Jamie was totally engaged with the story being told, to my lack of shock.