Finding the Perfect Fit Pt. 15

Stepping over to my desk, I dug around for lip gloss and handed it over to a stunned Jamie, who looked at the tube then me as if in a dream.

"I'mma change real quick, get some of this on, okay?" He nodded and I retreated back, flipping the closet light on and struggling into my own stockings before taking the second dress off the hanger. This was the prom dress, the most important thing a girl could wear during the most magical part of high school and both of those dances were 'meh' at best. Slipping into the black thing I'd last worn about a year ago, I adjusted the top and grabbed the heels off the largely empty shoe rack and rejoined a still stunned Jamie.

The bodice of my dress was tighter than Jamie's, with a V cut out of the middle to show cleavage and studded with little plastic prisms that caught the candle's meager light and almost seemed to glow. My skirts had a slit going up the sides, something a senior could get away with, I guess, as Jamie's dress didn't have any such thing. And I've already starting thinking of that gray dress as his. Jamie just looked so fucking happy in that thing, so why not give it to him?

"If ya dare, try these on." I dropped the shorter heels on the floor beside me and sat down, trying to remember the last time I'd worn heels. Probably for graduation cause the day after I was at Dick's, working for the summer to save up money for college and even left them at my parent's place when I moved in here. 'Cause I was tall, at least for a girl, I didn't go above an inch and a half but even that made me tower over most people.

Jamie got the shoes on and stood, wobbling hard and I offered a steadying arm but we both nearly fell. Laughing, Jamie shook his head and slipped out of the shoes, keeping me steady as I did the same.

"Next time. I think those are too small for me." Lips now shimmering and smiling, Jamie's spirits were high, stealing glimpses at the mirror every so often.

"If ya wanna learn, I'm sure we can find a cheap pair online and ya can strut all over this room and maybe even me." I wiggled my eyebrows at Jamie, leading him to giggle like a girl and my heart melted... just fuckin' melted. With my feet firmly on the ground, I stood and found the lip gloss, applying it while Jamie got to his feet and swayed in place, the skirt going to and fro as he watched.

"I love the way this feels." He noticed me staring and flushed further red, brushing hair out of his face and giving a sheepish smile.

"Don't you dare apologize." Giving him a pat on the ass as I walked by, I found my phone and kicked Fleetwood Mac back to life, setting the song to repeat before dropping my phone to the bed with the speaker facing upward, the sound clear and pure. Wrapping an arm about Jamie's waist, my other hand smoothly found his and just like that, we were dancing.

"I'm not good at this, I never-" I cut him off again, not wanting his past or doubts creeping back in here in here.

"I don't care. We'll get it right and if not, well, I'm sure we can find something else to do." Choking back tears, Jamie kissed me before laying his head against my collarbone as we swayed, his breath warm and inviting on my skin.

The first time Dreams ended I moved my hand back towards his butt and he looked up at me before following suit. We kept dancing to a song that was older than my parents, back when Stevie Nicks was probably the hottest damn woman on the planet. When the second loop ended, Jamie raised his head from my chest and kissed my cheek, not turning away when my lips let his.

"Can I-" Jamie started after our kiss ended but I was way ahead of him.

"Yes." I answered, knowing it would have to seriously be out there for me to refuse him.

"One of the dances I went to, I saw a girl doing this and..." Letting loose of me, Jamie turned around faster than needed, skirts twirling as his hips swayed with the music, much more lively than before when he had been burdened by expectations of being a manly man. Wrapping my arms about him, I stepped close and felt his butt through two thin dresses and even thinner panties. And so we swayed together, his hands over mine as he slowly pushed back into me, a light, barely there moan escaping from Jamie as I applied the slightest pressure to what he was offering.

I found his breasts without thinking about it or meaning to, slipping past the shimmery material and to the lace holding his boobs in place. Jamie's breath hitched and he pushed back harder, chest coming forward in my hands. This would have been the point a teacher would have stopped us but alas, high school was behind us and as adults, we were free to do this.

'Thunder only happens when it's raining.' Stevie sang but I disagree, there, between Jamie and I there was lightning and thunder was sure to follow. I saw us in the mirror and with his back arched to give me full access to his butt, his masculinity was hidden by the skirt and there was no telling Jamie was cross dressing. Sure, we both lacked make up and the elaborate hair dos but if a bottle of wine was added we'd be the perfect picture of drunk white chicks just having a good time.

Jamie was growing more insistent and I had to move things along, the winter break had been long and dammit I needed this. Finally taking the hand not fondling a breast to his back, I teased the zipper down and Jamie emerged from the dress, looking much more comfortable with the situation. I kissed him as I got the zipper down on mine, Jamie watching as it fell to a dark pool about my feet.

And then, in something that caught me off guard, he bent and picked up both, carrying them to the closet and I heard hangers 'clacking' as he hung them up. In a few steps, I got to the side of the bed that had the fun stuff under it and pulled the bag out, dumping the contents out as he rejoined me.

"I think that's the first time in the history of ever that's happened." Pointing the purple dildo at him, Jamie looked at that before shaking out of what had to be the pit of memory.

"What? They're nice and probably expensive and should be taken care of." Unable to help it, I laughed, finding that we were running low on condoms during. "What?!"

"Ya right, absolutely! Just, I dunno, normal guys wouldn't think of that. I mean, ya think Tom made sure his prom date's dress was off the floor before they did the nasty?" A single eyebrow rose, this line of thought not amusing to him. I found it extremely telling to his priorities and just nice. "Sorry! Sorry, anyway, whatcha want tonight?"

Looking at the floor, then lifting his breasts clad in a sheer lace bra, Jamie locked eyes with me and a grin broke through, one that spoke of trouble.

"Maybe I need to give being a man another shot. I might even get it right this time." I blinked, not catching what he was putting down. "I want you to fuck me again. With that." He pointed at the dildo I was still holding and I frowned, catching him by surprise. "What? I thought you'd want to."

"Well, yeah but I don't want to do it as a 'fuck you!' to your shithead Dad. I want to do it cause you want to, okay?" Slapping hands over his face, Jamie leaned back and growled up to the ceiling. Eternal and lumpy, it gave no answer.

"I do! I just, I need to get out of my head, to stop thinking!" He sounded desperate and I swept in, catching him in a hug and awkwardly sidestepping us closer to the bed.

"I can do that. Cause I got another surprise." We toppled over, Jamie with a squeak as I kissed him deep and hard, rolling on top. "I did research over break on fun things to do with this." I tapped the dildo on his nose, Jamie going cross eyed to watch as it did so. My other hand went to his bundle of joy, taking my time in feeling how hard he was yet molded by something so fragile looking.

I peeled, literally in this case, the panties off and the sigh of relief as he sprung free was adorable. Still, I found a rag shirt and put it under his butt, to catch the ensuing mess. Grabbing the lube, I cracked it open before tearing into a condom and slipping it over two fingers.

"I feel... Stupid? I guess?" I mulled out loud, pouring the lube on my protected fingers and rubbing it in the dark trench of Jamie's crack, getting drawn out sigh from him.

"Why?" He managed to ask, impressing me. It can't be easy to carry on a conversation when being prepped for butt stuff.

"Cause I spent the break working and being horny, looking at new and fun ways for us to fuck while you're dealing with ya sexuality." I refused to evoke Jamie's father, lest his spirit return to ruin things. After some feeling around, I found that entrance and, with more lube, slipped in. His moan and the jerk his tower of a dick gave pushed me to keep going, give him what he wanted but I had to go slow.

"You'd already dealt with it. I hadn't." Sure, he was having trouble getting the words out but Jamie was speaking his mind. Good for him. "After that weekend, God! I had to come to terms with everything." Jamie had spread his legs without me needing to ask and I curled my fingers upward where all the articles said the prostate was and his speaking became more fractured as he struggled to say his piece. Or peace, I'm not sure. Never seen that saying written down before. "I'd, oh, oh man, I'd asked for it and did it twice and you only once." Took a second but I figured he was talking about times taken up the butt during that long weekend together.

"That first time was so intense I thought it was a fluke, ahagn!, had to be. Nothing could be that good." Jamie said, his words still coming even as I kept finger fucking him. I wanted to hear what he had to say and that he was plowing past my best efforts was all the more impressive. He had to get this out and I would listen before bringing the dildo into the mix. "But it was! Better even, cause it was easier oh God, what are you doing?!"

"Making ya feel good." While awkward, I got my other hand on his penis that had been towering over what I'd been going and gave it a few good strokes. "Keep talking." I said, hearing his rapid breathing and bit back laughter as he did what I asked.

"Okay, okay! I uh, looked and asked around and couldn't figure out if liking things in my butt made me gay. I, I knew I liked when I did that to you but the other way, I ugn! like that more." I let up rubbing that certain spot which stole away his words but kept my fingers in that hot, welcoming embrace of Jamie.

"Being gay means you're attracted to the same sex." Moving his dick in circles with a finger atop the slightly leaking head, I got nothing but silence in response to that. "I take that's a 'no' then?"

"Not really?" Lifting his head, Jamie looked at me for a few seconds until he fell back. "I love you and your shape, figure, all of that. Guys are flat."

"Except this." I gave his dick a stroke and put a tiny bit of pressure on that spot within him, getting a groan. "Guys have this and I think that makes them interesting, don't you?" Granted, fingers and toys could get the job done but sometimes the real thing wins out.

"Yeah but that's it, all they got. You're better, got curves and that!" I let off his dick, not wanting Jamie to blow early. "Gen, I'd never cheat on you with a guy." I snorted, hearing his earnestness and discarding it.

"I'm not worried bout that! Hell, if ya do wanna fuck a guy invite me along! Cause that'd be amazing, seeing ya get the real thing." Oh Jesus, even typing that out drives a burning spike into my brain and just... Fuck! "Ya right about one thing: I got dicks for days." Having been lubing up the dildo, I withdrew my fingers and lined up the shot as if I was playing pool. Then, laying almost flat on the bed so I had the best seat in the house, I saw as Jamie swallowed up the dick up to its purple balls.

"Nggg!" Leaving that sight behind, I crawled to his panting head and watched him for a few seconds, still glossy lips parted, shoulder rolled forward as his head was tossed back and there was no growl this time. No, he shuddered and there was a moan, one befitting someone who had been in a prom dress and was still in a lace bra.

Without much effort, I undid the bra and pulled it free, Jamie blinking and looking at me as if he'd forgotten I was still there. Taking a nipple in my mouth, I reached between his legs and past his erection to the dildo, beginning to work both.

"Oh fuck! I-I!" Anything else became a lovely whimper, telling me just as much as all those words he'd managed until the dildo stole his speech away. But I wasn't done yet, his boob was just a detour. Finding the lube, I poured some in a hand and wrapped it about his dick, watching his eyes go wide at my touch.

"I've heard that being bi is the best of both worlds." I gave a few strokes, making sure he was good and covered before kissing the tip, the taste of not quite cherry but close enough coming back to me. "And I think ya deserve that." Then all talking stopped as I had something more important to do with my mouth and his scream confirmed it. Jamie was getting it both ways, being penetrated and blown, the typical roles of male and female sex at once.

Jamie thrashed, arms and head seized by sudden needs to move until suddenly coming to a halt, the sounds of his breathing mingling with my wet giving head noises as I made sure the penis not in my mouth never stopped.

"Ah! I!" There was nothing else it could be: Jamie was close and trying to warn me. Rising off his dick, I darted over and kissed him, my tongue running about his lips.

"Do it." Slamming in the phallus in faster and faster until my wrist hurt, I kissed his exposed neck as his head was swinging side to side, as if saying no, trying to deny his orgasm. "Come on!" With my demand hanging in the air, I took nearly the whole of what had been trapped for so long and lashed my tongue about until that salt tide flowed forth.

Jamie screamed, clawed at the blankets, went fucking feral as I pushed the dildo in to the balls and held it there as more and more was shot into my mouth, some of it spilling out or being swallowed as I had to breathe. Giving up, I chugged the whole load and rolled over on my back, gasping for air as my not exhausted hand went into my soaked panties and started what needed to be done. After what I'd seen, hell, done, it didn't take long.

I was shot after that, laying there knowing things needed to be cleaned up but I couldn't bring myself to move. Until I heard a wet, lewd sound and a pitiful moan from Jamie and knew what I was going to see. Sure enough, without something holding the purple dick in place, it had slipped free and was now laying atop the shirt I'd put down, freshly fucked and not at all impressed.

"Uhh... That felt weird." His tired voice cracked and I knew what the both of us needed: Water. The ever trusty bottle was nearby and mostly full, it being split between us. And just like that, we came to life and started cleaning up. I wrapped the toy that had done so well and took it to the bathroom, using soap and nigh boiling water to ensure my dick was clean before being put away back under the bed. Jamie had taken off his stockings and was putting the whole outfit in the closet when I got back.

"I should be used to how that feels by now but I'm not." Jamie said in a conversational tone as I tucked the bag under my bed as he took his turn in the bathroom. Thankfully Donna was still gone, probably wasting her time at some party. Returning after a few minutes, I saw that he wasn't able to wash away the 'I just got laid' looked and I was pleased by it.

"I don't know what got fucked the hardest: my butt, dick or soul," he said in the same everyday voice, and I failed to bite back a snort while tying my shoes. Getting that done, I leaned on his shoulder and outright laughed when he slapped my hand creeping into his lap. "No more of that, not tonight!"

"Aww but Jamie, I need it!" Whining as hard as I could, my act paled to the huge performance sigh Jamie gave while lifting his shirt to reveal the black comfy bra.

"You get these, nothing more." Said like a parent trying to placate their child, his eyes rolled as I clapped in glee.

"Yay, boobies!" I didn't even bother to make a grab at them, laughter had found me once more and wouldn't let go. "The fuck is wrong with us?" I got that much out as Jamie shook his head.

"Pretty sure we're terminally weird." Standing, checking his pockets, Jamie helped me get to my feet and his crooked smile paired with red eyes told of a long, trying night. "But you know what? I'm fine with that."

"Yeah, me too." I said, sobering up and finally shutting up Fleetwood Mac. Hand in hand we got out to my car and got it going, the night as dark and cold as any other we'd spent together. "I was serious, by the way."

"About?" Jamie said, hands in his coat as we stood in the cold for no reason other than to be on our feet. Less than an hour ago he had been in a dress and driven to tears by it. How quickly things change, especially when dealing with the public.

"Ya wanting the real thing." I smiled, seeing Jamie having trouble recalling the conversation. Meant I'd done a good job. "If ya ever wanna try real dick, we'll figure out a way to make it work."

"I..." Face red and not from the cold, Jamie looked at glimmering lights in the distance as I leaned against my car, not expecting any answer. "That's a big step Gen. It's one thing to do this but... Doing that, it feel permanent."

"Like wearing those pink panties?" I asked, knowing it wasn't the same thing at all but that world shattering event for him was tame after that Thanksgiving weekend.

"No. Yes. I think?" Jamie struggled to say anything more but I stopped him from trying.

"It's too late for this soul searching shit." I said, getting a chuckle from him. "I just wanted to let ya know that's possible, if ya want." Gesturing, we got in the car and started off for his dorm.

"What about you? Is there anything you'd like to try?" Jamie asked and I was very, very careful in my answer. I hadn't been kidding about it being too late for this and my thoughts were a drunken tornado, having sucked up all the information from the night and throwing it every which way.

"I've still got ideas to try out." I made kissing noises in his direction and Jamie only rolled his eyes. "We'll deal with this later, okay? I gotta get some sleep." With a kiss and a final searching look, he bounded up the steps and I watched him leave then drove back home. Haven't been able to sleep so I started writing this and it's done the job I'm so fucking tired and gotta work in the morning but how brave of Jamie to admit not being straight to himself then me.