Finding the Perfect Fit Pt. 12

Waking up disorientated and wrung out, I lay there looking at my dorm's lumpy, discolored ceiling before noticing Jamie's breathing next to me. Lulling my head to the side, I saw him flat on his back, still with stockings on but having cleaned up at some point. The steady, slow tempo of his breathing was comforting and the view of his chest rising and falling alluring. I blinked, yawned and rolled over, if only to get away from the glare of the light that was still on. Checking the window, it was dark as was usually the case during winter and I had no idea how much time had passed.

Laying there, pulling down the elastic tops of the stockings to let my legs breathe, I began recalling what we'd done together and how to begin to write it down. Fumbling around, I found my phone and pulled up a barely used notepad app and tapped out thoughts, pausing to formulate thoughts and make sure I got it right. Jamie stirred and I powered down my phone as he rolled over, blinking a few times before his eyes focused on me.

"Hey." I got a groan for a response as he rolled over and sat up, drinking deep from the water bottle always by my bed.

"Sup," Jamie said, handing over the water which I greedily finished off. "How are ya feeling?"

"Was gonna ask ya the same thing." But now that he asked, I noticed some... Not discomfort but awareness about my butt that hadn't been there before. And that it was still sticky slick with left over lube.

"Tired, thirsty as hell and still horny." And, true to form, he blushed while saying that. "Guess all I needed was a nap and I'm ready to go again." True to his words, I saw what I'd taken stirring back to life.

"Well... Whatta wanna do bout that?" I asked, hoping for anything but his answer was more practical than horny.

"Get something to drink first." Climbing out of bed, he stretched, butt tightening then relaxing back to it's usual panty filling shape. Padding to the door, he cracked it open and peered out into the living room before slipping out, still nigh naked and with smeared make up. If Donna happened to be out there and saw him, she'd have questions but really, all the answers to them as well.

Getting to my feet, I mimed his actions and cracked my neck a few times, taking my first few steps as a woman who'd been deflowered in the butt. And they were the same to the hundreds of thousands I'd taken before. It'd been intense and I'd enjoyed it but Jamie had been a large part of that. Heh, Jamie had that large part alright!

The smoldering ember of lust and desire began glowing, waiting to be stoked back into the all consuming inferno that Jamie always was able to summon. Standing by my desk, I tapped the surface as I wondered if he was willing to honor our deal and if I could take my turn.

"Here." Pulled out of my thoughts, I jumped and turned at the sound, fumbling the chilled bottle of water tossed at me. "Oh shit! Sorry." I snapped it up and drank, then held what was left to the forehead in a vain effort to cool the urgent demands being made by that furious flame that seized control in the throes of ecstasy.

"All good." Jamie's flagging erection was perking up as we stood, drinking in quiet. "Well?" My question, a single word, was loaded and Jamie knew it, taking his time to respond.

"Tis good water." I blinked a few times at that, at a loss for words. Jamie grinned, screwing the cap back on the water and sliding it on the end table. "You keep telling me to say whats on my mind so I'm gonna ask you the same thing: Whatcha want Gen?"

Taking another deep drink, if only to gather up my thoughts, I discarded the empty bottle on my desk and spoke:

"I wanna know if ya will take ya turn. If not, I'm sure we can find something else to keep us busy." He nodded as color poured into his face as both dick and nipples stood at attention, showing his excitement.

"I took that uh, thing out earlier when I went to the bathroom. Felt weird. Oh and I washed it off cause... Yeah." Probably for the best. Going to the bed, I found my phone and tapped the screen, finding about two hours had passed and we still had plenty of time. Jamie opened the drawer on the bedside table and pulled out something wrapped in paper towels, revealing the butt plug.

"And... I wanna take my turn." Instantly the inferno roared to life, Jamie looking at the sex toy he held as if it was whispering forbidden knowledge. "The way you looked during that... I want to know what that feels like." A tender smile graced Jamie's features, becoming wicked as he gave his erection an idle slap, sending it bobbing about.

"Coming right up, Pandora!" I swept up beside him and Jamie's body pressed to mine, soft and welcoming mixing with hard and insistent. Lips brushed mine, hands running down my body as I did the same back, learning him anew.

"Pandora huh?" Jamie panted in my ear as one of my thumbs ran round and round his areola, that softness calling to me even with everything else being on offer. "Sure, why not." Leaning back, he grinned, eyes flickering from breasts to my face. "Can you blame me though?"

"Not at all." I gave the boob I was still fondling at gentle squeeze, getting a moan that ran counter to his reason and rationale as my reward. "I'm so fucking happy you opened that box." Withdrawing from his warmth, I knelt and pulled out the bag with the strap on inside. Jamie watched as I dumped the strappy thing, Big Clit and the purple dildo that was a twin to what Jamie was packing out onto the bed.

"Alright, uh probably outta get the plug back in and give it a few minutes." Flushing redder, Jamie handed over the lube and knelt with one knee on the bed, exposing himself. The view was one I never expected to see. Sure, his boobs had called my attention at first and still did but this? It was another level of trust, of offering this first to me and I couldn't say no. I had called him Pandora but I wasn't any better, finding more to share and experience together.

"Okay, holy shit, relax," I murmured. A green eye, the color deepened and purified by the black rimming it, looked over a shoulder just as I had thought of when buying this stuff and I bit back a moan.

"Are you talking to me or yourself?" His voice was playful yet impatient, ready to get on with this. Unable to keep away from this impossible vision, I rushed to him, taking Jamie in my arms as I pressed to his back. Dropping the plug, I took breasts into my hands and felt their softness and heft as my own smashed into his warm and smooth back. With a minor adjustment, my pubic mound found where it had been before and he gasped as I finally got between his cheeks and into that valley, giving a thrust that I pulled him back into.

Words failed me as I got a moan that sounded like nothing a guy would produce and that fed the fire, urging me onward. Jamie's back arched as I gave another thrust, my dripping heat nearly enveloped by him, the closest we could get to me fucking Jamie like this without aid. Letting loose of a boob, I clawed at the messy bed until I found the plug, the lube being handed to me while he ground back, swaying hips to and fro as a moan, almost a sigh coming from him.

Popping open the lube, I slathered too much on my fingers and reached down, slipping between our bodies and finding where he wanted me to be. His breath caught when I found what I was after and applied pressure ever so slightly then rubbed, spreading lube. Maybe I said something to comfort him, I can't remember. I just know we perched on the edge of pleasure and madness together as I made sure he was good and slick before running a finger over that entrance and this time when pressure was applied, I sank in.

I gasped, feeling Jamie's heat without interruption as he gave a whimper, moving his hips towards me and sinking my whole finger in to the knuckle. With that in him, I pushed my body closer to his, thrusting my hips and pushing forward with my hand, using all I had to give him what we both desired.

Pulling out slightly, I lined up a second finger and with a gasp, it too went in. A shiver ran down his spine and I retook my position right against him, finally reclaiming my other hand from his breast to brush hair out of the way so I could plant a series of kisses on his neck. Working my fingers in and out, I was stunned when he spoke actual words, something now beyond me.

"Get the plug in and the strap on. Hurry." The voice that spoke was lighter, as if trying to be more feminine but was completely lacking the meekness that he displayed when trying on women's clothes for the first few times. No, Jamie knew exactly what he wanted and I had to obey. The plug was picked up again and handed back to me, his breathing hard and butt still tight. However, I had to a job to do so I pulled free, pouring more of the cool liquid on that hand and used it to cover the conical part and reapplied it to Jamie. That done, I whispered that he asked for this and needed to be ready. Lining it up, I watched as the purple tip disappeared and there was only the disk left, a muffled 'unfff!' as it slipped in.

That done, I staggered back a few steps and nearly fell over, getting some much needed air before walking on numb legs to my dresser and pulling out a shirt I didn't care about to wipe my business hand off. Back over to Jamie and the strap on he was resting beside, I picked it up and nearly paused at the fierce, rapturous expression on his face.

"Please hurry." Eyes barely open, make up a mess, Jamie might have been a college girl after a long night who had decided on going back for more when the body wasn't so willing anymore. Stepping into the harness for my fake phallus, I pulled it up and secured the waist, then picked up Big Clit. "That?" The disdain in his voice threw me off, so out of place here.

"Yeah, it's smaller and will warm you up for this." I found the bigger one under a fold of blanket and showed it to him.

"Use the purple one. You took me and that looks about the same size. Fair's fair." Any argument I might have presented about not wanting to hurt him withered as his suddenly sharp eyes pierced past locks of errant hair to implore me without speaking to hurry it up. Lifting the O-ring, I secured the dildo and began lubing it up, Jamie's new razor gaze watching me all the while.

"Ready?" I asked, more than slightly out of breath by this ordeal turning out the way it was.

"Yeah." Taking up my spot behind him, I waited as he switched legs, once more with a knee on the bed and showing the butt plug holding him open. It probably hadn't been in there long enough but I wasn't about to mention that. Jamie might have wanted this more than I did and turning back, saying no, wasn't possible anymore.

Soaked from dildo to pussy, I reached down and pulled the plug free, wrapping it in the shirt and tossing it aside. Stepping close, I placed a hand on that slight flare of hip as I grasped the base of my new dick to aim it. Bending slightly at the knees, I placed the head where no man had gone before and gave a little pressure. A groan, one I knew all too well, came from Jamie and I shook my head.

"I'm gonna get the smaller one-"

"If you did it then I can too." I watched as he pushed back and instead of his butt mashing to my front as it had before, it tried and failed to take the dildo blocking the path to me.

"Slow down. Breathe." Running my hand up and down his side, I pushed him forward, exposing his butt more. Retaking my grip, I lined up the shot and this time, there was give. The head was gone, enveloped and venturing into the Land of Jamie. A weak whimper was his reply. "I know, I know. Gonna go slow. Tell me to stop if ya gotta."

A count to ten and I got another girly moan as more latex dick was pushed in. A quarter of it was gone now, the false veins on the surface being swallowed up. Half now, each breath Jamie took ending in a light moan that didn't sound like discomfort.

"Doing alright?" I needed to know, have my conscience eased before taking this any further.

"Ahh..." A trembling hand rose and gave a thumbs up and that was all I needed. Grasping his hips with both hands, I pulled out until I saw the flare of the head and slowly pushed my dick back in. Once more, the slick shiny purple started disappearing and a greedy moan came from Jamie, a tremble flowing through him but no call to stop. This was the promise from each dry humping session made real and the full extent of me was going in. After all, I'd taken it so he could too.

Half was now in and my head was angled down so I could watch as his butt took three quarters, the noises Jamie was producing building the fire that had seized control of my being to apocalyptic levels. Spreading my legs, I slammed the last inch and some into Jamie, his scream mingling with my roar of exhalation. He called out to Christ, to God as I slipped a bit of purple out, then put it back where it belonged: Into Jamie.

Buried balls deep, I rolled my shoulders back and raised my head, seeing Jamie's shuddering shoulders and lamenting not being able to see his face. With a motion of my hips, a flash of color appeared from Jamie's ass and then it was gone, his butt pressing into the contraption that held my manhood in place.

The positions were right, the barriers of discomfort banished, all other thoughts and inhibitions fell away. Drawing back, Jamie pushed into my crotch, cutting my thrust short. That wasn't going to stop me, I simply pounded with what little room he gave him, the tempo off but getting the job done. We swayed together, speech having giving way to primal moans and the slapping of me impacting his butt.

Whipping his hair back, Jamie looked over his shoulder at me with a single wild eye that told me everything I needed to know. Nearly at the same time, we resumed motion, him rocking into my thrusts as I held on tight. Need collided with need and each drove the other higher and higher, to the heavens and beyond. Dribbles of heat were rolling down my thighs and I had to fight to keep upright as a shattering of reality took me, my thrusts becoming weak and erratic. Jerking and jittering, Jamie kept this most important work going as I rode out an orgasm from fucking him, Jamie was riding my dick and somehow it got more intense but I still stood as he picked up speed and make a noise that I can only describe as a needy scream.

Once, twice, three and Jamie was plastered to me, to the dick I wore and took up handfuls of blanket as he shuddered, hair flying about as I fell on him, a hand that I barely felt cupping a breast as he whined. Looking down, there was his dick which I'd completely forgotten about and ignored, firing load after load all over my bed. He was orgasming hands free and I watched, fascinated, as it let loose without being touched. No, my dick, equal in size to his if not realism, had summoned it from Jamie, something I hadn't known was possible.

With a body that felt slow in responding, I peeled off Jamie and pulled my dick free, the pitiful sound that he produced would have been worrying in any other time and place. Undoing the strap, I tripped towards the bed and pulled Jamie down along with me.

Laying there, feeling his warmth and a sticky patch of his warmth that had been expelled, I failed in clearing away the fog of exhaustion but found the water bottle still on the stand. I drank enough to be able to speak, assuming my brain had that ability still, and passed the rest to Jamie. If before he had looked like a college girl going back for seconds, now Jamie's appearance was someone who had won at sex forever. The glow in his face, the tussled hair, and smeared lipstick all attributed to this conclusion.

"Well, how was it?" Most of my being was unresponsive but I still feebly helped him sit by me, Jamie's head leaning against my shoulder, his hair a pleasant tickle as he drank.

"Can't describe it. Too tired." His penis had mostly deflated and was still drooling on his leg, that puddle leaking down to the bed. Laundry had to happen now but that was Future Gen's problem.

"Didn't know you could get off like that." I said, the fog of exhaustion stealing away what little awareness I had left.

"You did too." Jamie's retort was equally tired, lacking conviction but he wasn't wrong.

"Yeah, guess ya right." Kicking the soiled blanket off the bed, I wrapped the sheet about us and rolled over to face him. One last exhausted kiss and I fell off the World of the Waking. Wasn't quite asleep but couldn't move, drowsing for another unknown amount of time with Jamie.

And yet, I broke the surface of that gray lake and blinked, shockingly awake after that brief snooze. Jamie was still out but that wasn't an option for me. Carefully extracting myself out of his tangle of arms and legs, I thought for a moment before finding a shirt and my laptop and slipping out into the dark living room.

Walking to the kitchen, I flicked on the weak light and slipped into the shirt. Dressed, I dug about in the fridge for leftovers, setting on a piece of ham and yet more water. Scarfing the cold meat down, I took the water bottle and laptop to the couch Donna was usually camped out on and powered the computer up.

Stretching my legs out, they had put in some serious work today, I drummed my fingers on the worn plastic surface where my palms usually rested. Getting my thoughts in order was proving difficult as thinking about what Jamie and I had done was addling my ability to formulate the events into words. Instead all I was getting was Jamie's single eye looking over a bare shoulder with my dick buried into his ass, his movements picking up, fucking me.

Taking a drink of cold water, resisting the urge to dump it over my head, I opened this document and recalled taking Jamie's dick and the notes I'd written after. Fueled by horniness I somehow still had in reserve, I slammed that out in mostly one go, stopping only to drink.

That done, I set my computer to the side and pulled the stockings off, sighing as I crossed my bare legs and the laptop retook it's usual place. Yes, sure, I'd done anal but a few hours ago, I'd given it, dealt out the penetration. Like, I hadn't ever given that any thought. Cass and I had been fine making out and would have probably moved on to going down on each other before being found out. We'd never brought up or talked about using a dildo on each other, nothing of the sort. And my boyfriend hadn't touched the topic at all.

And here I sat, having strapped on and gone hard on that ass. I opened YouTube, found Dreams by Fleetwood Mac, and started typing. Once it was all down here, I was fired up and ready to go again. Jamie's actions and mood during that still baffled me but with him still asleep, there wasn't much else I could do. So I-

As I was typing that, Jamie came out of my room and slept walked to the bathroom, me saving and closing this document and replaying Dreams. He came back to the living room, blinking, head cocking to the side as he listened to the music.

"Stevie Nicks? Or Fleetwood Mac?" I told him the latter and he nodded, standing there naked, having removed his own stockings at last. "Is there anything to eat?"

"Sure but no being naked in the kitchen." He flushed and disappeared back into my room, me turning the music up and carrying the computer with me to the kitchen. Jamie came back with the T shirt he'd shown up in, baggy enough it covered his goods.

"Got Thanksgiving food. That good?" He nodded, still looking half asleep and dished up mashed potatoes and ham, drizzling gravy over the mess and sticking in the microwave.

"Everything alright?" He asked me, rubbing his eyes and smearing the make up even further. At this point, he'd end up looking like Joker from The Dark Knight if nothing was done.

"Yeah, everything's great. Why, what's up?" He blinked a few times, looking at me with a scrunched face.