Homecoming Queen

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I was in heaven and it was obvious that Jason had finally relaxed and was letting this happen. The tension between us all night was palpable. Now, all that worrying about norms and secrets was building up in his balls, waiting to explode into the waiting depths of my mouth.

I worked his cock with a fever I had never felt. I wanted to make Jason cum. I wanted to pleasure him more than any girl at that stupid party ever could have. I wanted to taste that sweet, sticky cum on my lips and let it run down my throat.

Jason's legs stiffened as he locked his knees. His weighty testicles rose in preparation of releasing a torrent of hot, sticky fluid into my wanting mouth. I worked his long shift with my hand as I locked my lips around Jason's cock head and waited for my reward.

At last, it came with a large grunt from Jason. His knees buckled as he unleashed spurt after spurt into my hungry hole. I sucked down gulp after gulp, but Jason was still cumming. I counted six streams of cum as I hurriedly did my best to swallow every delicious drop he provided.

I could take no more and thankfully neither could Jason. He fell back onto the bed, pulling his clock from my mouth just as I had captured the last of his cum. I let it sit on my tongue as I savored the taste and texture, making a show of it as I let it drip down my glossy pink lips before slurping it back into my mouth and swallowing it down.

My breasts heaved up and down in my dress as I finally caught my breath.

"Holy shit," exclaimed Jason. "That was...amazing. How'd you learn to do that?"

I wiped the remnants of cum and spittle from the corner of my lip with my fingernail before sucking it clean and giving Jason a devious smile.

"It was my first time." I said with an innocent smile and a shrug of my bare shoulders.

"Well...it was, I mean you were incredible. I've never gotten lightheaded from cumming before." Jason complimented my dick sucking prowess.

"I'm glad that I have the Jason "Seal of Approval," and the paperwork to go along with it." I quipped as I attempted to clean off any remaining cum from my lips.

I got up off my knees and kicked off my heels before straddling his prone body on the bed, placing my white hot crotch against his still hard and throbbing cock.

"Wanna know the best part?" I asked.

"What's that?" Jason said, finally catching his breath.

"You can fuck me and not have to worry about getting your Homecoming date pregnant." I said with a little giggle, bringing my hand to my mouth for effect.

Jason's eyes shot open. "Um, a blowjob was one thing Al. I don't know if I'm quite ready to have sex with you. This is all pretty new territory for me."

"Wow," I laughed in earnest. "All that blood leaves your head and you forget how to take a joke." I said, pushing his shoulder as I rolled off him to the side to lay next to him.

"Don't forget. This is all new to me too. I'm kinda dealing with these feelings as they appear." I admitted.

"Oh...Okay, that's true. Sorry Al."

"Nothing to be sorry about," I said. "I just had an amazing night with my best friend."

Although I played it off well, I was a little disappointed. Only God knows why, but my first day as a woman and I was ready to lose my virginity to my best friend of over a decade. For the first time since this saga started, however, I finally felt comfortable in my own skin. I no longer felt like I was playing a role in a play. I wanted to be Allison and I wanted to be with Jason. I had no idea how he felt, but that was a conversation for another day.

We chatted and laughed about the evening as we laid side by side on the bed. I ribbed Jason for the terrified look on his face when Dan caught us making out.

"I thought you were gonna have a stroke." I laughed out loud.

"Shhh, you'll wake my parents." He scolded. "But yeah, I almost shit myself."

It took me a minute or two to regain my composure, tears beginning to form in the corners of my eyes from laughing. I sat up and pulled myself up off the bed. Jason pulled up his boxer briefs and watched me with a careful eye.

I spun my back to him and presented my behind, looking over my shoulder back at Jason. He continued to stare at me with wide eyes, dumbfounded by the vision before him.

I coughed to break his gaze. "Um, care to help me with an unzip?"

"Uh, what?" He said lazily.

"Well, I'm not wearing this dress to bed...and I had a hell of a time getting it zipped up on my own. I don't really feel like contorting myself in my current condition." I lectured.

"Oh. Yeah, okay. No problem."

Jason slipped off his pants from around his ankles and stood to help me with my dress. He reached out and grabbed the zipper at the nape of my back like it was made of hot coals, afraid that he might get hurt if he touched it too long. He unzipped me with a long, slow pull down to my lower back, revealing the back of my bra and the top of my garter belt.

I turned to face him and was delighted to see him wide-eyed and nearly stupefied, mouth slightly agape. I slid one arm from the dress and held it to my chest as I removed the other. Jason didn't move an inch and his gaze never left my body. I moved my arm away from my body and let the dress fall to the floor, creating a pile of polyester and tulle around my stocking clad feet.

I stood before Jason in my secret weapon. The outrageously expensive lingerie that I just had to have to make me feel sexy. I was now glad that I had splurged on the purchase. Jason drank in the sight of me in my lingerie. A muse, basking in the soft glow of the lamplight. I stepped out of the dress with deliberately pointed toes and gave myself a good once over, enjoying the torment I was giving this poor boy.

Never before had I felt power over another person like this. I knew, no matter what I did, I had Jason's complete and undivided attention.

I motioned toward the bed and grabbed his hand as I tiptoed toward it.

"Well, shall we get in bed? I'm getting sleepy." I yawned.

"Um, you're gonna sleep in...in that." He stuttered, motioning to my outfit.

"Well, it's this or nothing at all," I said. "I'll clean up in the morning. You gonna join me or just stand there and stare at me?"

"We're going to sleep in the same bed?" He asked as if ashamed.

"Yeah, I'm not sleeping on the floor tonight. I think I've earned that." I said as I gazed at the wet spot on his boxers. "You're welcome to sleep with me in the bed or sleep on the floor yourself, but having slept on your floor, I recommend joining me in bed."

I was enjoying this newfound power and confidence. It emanated from me like a guiding beacon. I knew Jason wouldn't be able to resist, and as if I commanded it, he joined me in the bed as I pulled back the cover and patted his side of the full-sized mattress.

"Don't worry, I won't bite." I teased.

Jason removed the remainder of his clothes with the exception of his boxer briefs. I couldn't say that I was disappointed in his bedtime attire, much as I was confident he was enjoying mine, even if he was doing his best to hide it.

He finally joined me under the covers. I gave him a hug, making sure to press my breasts up against his chest, and a small peck on the cheek to thank him for a wonderful evening. We laid down and covered up. My pinky played with his hand and I teased his leg for a few minutes with my still stocking clad foot before finally rolling over and curling up into the little spoon position.

I thought to myself, "That ought to give him something to think about tonight."

I fully did not expect him to roll over and join me as the big spoon, but for once Jason finally surprised me. After several minutes of laying on his back, he rolled to his side and placed a hand on the lace top of my stocking. I reached up with my right hand and intertwined our fingers, making sure his hand didn't leave my thigh.

Despite his new confidence, I could tell he was still apprehensive. Jason didn't move his body any closer to mine, despite having his hand firmly caressing my thigh. I decided to take matters into my own hands and backed my plump butt back into him, forcing Jason to embrace all of me. My devilish grin returned as he moved his hand to caress my hip and ran it along my entire side.

I could feel that tell-tale pressure between his legs returning, this time pressed firmly against my backside. I loved what I could do to him. I moved myself back and forth, up and down, eliciting a small moan from Jason.

"Do you want me to stop," I whispered.

I was giving him the option, but I already knew the answer.

"No, don't stop," he said under his breath.

I continued to grind my butt into his hardening cock until it reached its apex, head once again peeking out from the waistband. I licked my hand and reached behind me to grab his dick. I stroked it, lubing it up with several mouthfuls of spit and saliva.

Once I had it to my liking, I pulled my thong to the side and pressed the head of his beautiful cock to my opening.

"Slide it in," I whispered, giving him the go-ahead to deflower my ass.

Jason didn't say a word, but I received his response through a firm grip on my hips and an increased pressure against my hole. I moaned as the pressure built, my virgin ass clinging to its last bit of decency before it finally gave way and opened to allow the intruder inside. The head slid inside of me, giving me a new sense of pleasure and pain. I gasped and sucked in a large gulp of air.

"Are you okay?" Jason asked, afraid that he had hurt me.

"I'm fine," I grunted. "Just not used to it. Stay right there for a minute."

Jason stayed completely still. I caught my breath and my ass began to welcome this new feeling of immense pressure. My sphincter finally relaxed and I felt the tension leave me from my back through my toes. I curled my toes in anticipation of the next sensation.

"Okay," I whispered. "I'm ready."

Jason delicately increased the pressure as he leaned into me. His beautiful cock disappeared into my ass inch by inch. I only wished I could have seen the sight.

"Oh my God," I purred as Jason filled me from behind. "That feels so good."

"You feel amazing too," Jason moaned.

He pulled back and re-entered in short, shallow thrusts, allowing me to enjoy and relish the fullness his dick offered.

I reached my free arm back to touch Jason's face behind me.

"You're filling me up. Your dick feels amazing. Please don't stop." I begged.

Jason took that as cue to pick up the pace and increase the depth of his strokes. My ass welcomed the challenge and I began to meet his thrusts with one's of my own. You could begin to hear the muffled sounds of his thighs bouncing off of my behind under the covers. My moans and cries of pleasure became more pronounced, urging a proper fucking.

Jason finally became emboldened by my persistent mewing and flung the covers off of us. He grabbed my right thigh and pulled, rolling me on top of him as he rolled with me. I spread my legs and finally felt the full depth of his cock as he cupped my breasts from behind and pulled my back into his chest.

He pawed at my chest, gripping my breasts tightly atop my bra as I arched my back into him. With my new leverage I was able to plant my feet into the bed and lift myself up and down on his rigid cock. I was finally able to fuck him back, and fuck him back I did. I was a woman possessed. I bucked up and down with my hips, riding his amazing dick like a bucking bronco.

Our breaths built to a crescendo. Sweat started to pour down my face. My ass cheeks slid against his hips. Jason had finally freed my meager breasts from their enclosure and had a firm grip on each with his strong hands. I continued to ride him like my life depended on it, making entirely too much noise in the process.

Still wearing the stockings and thrashing on Jason's dick like a mad woman, my feet slipped out from under me and I bottomed out on his cock, taking it to the hilt, deeper than any previous thrust. Jason moaned and spasmed beneath me. My legs locked out straight as I rode his orgasm to completion.

"Ugh, ugh, ugh," he grunted as he emptied his balls into my ass.

Jason gripped my hips and held himself as deep as he could reach until he shivered from completely draining his seed into me. I collapsed onto his chest and Jason lightly ran his fingers from my thighs across my hip bone and up my stomach. I got goosebumps from his touch.

He laughed at my sensitivity. I grabbed his arms and wrapped them around me, taking in his warmth as he embraced me from behind.

"Ho...ly...shit," he gasped through labored breaths. "I have no words."

"No words necessary," I purred back at him, enjoying the feeling of his embrace as his cock softened and began to slide from its place inside me, leaving a slimy trail of spit and semen in its wake.

Once Jason's dick finally slid free from my ass, I rolled off from on top of him and cuddled into his left arm, draping my left arm across his midsection and my left leg across his. I fondled his chest with my fingernails, lazily drawing circles on his skin. He turned his face toward me and I showed no hesitation in taking his bottom lip between mine, savoring the salty flavor of our combined sweat. Slowly, we drifted off to sleep in that position.

I woke after only a few hours of sleep as the sun began to peek through the bedroom window. I quietly snuck out of the bed and made my way to Jason's shower. I scrubbed off every last bit of Allison, including all of the makeup, perfume, and bits of dried semen, and once again became Allen. I dried and dressed in my street clothes and crept back into the bedroom.

Jason was still asleep, and I decided that it was probably best to be gone before he woke. A conversation needed to be had, but I had a feeling it would go differently than I hoped if I had it dressed as Allen. I made my way upstairs and headed for the door, when Mrs. Trevino called out from the kitchen.

"Allen, I didn't know you were here."

"Oh, hi Mrs. Trevino," I said. "I ended up taking another girlfriend of Jason's to the dance. After the party I felt it was safer to just spend the night here. I need to get home and get ready for work though."

"You made a good call. I'm glad you didn't drive home."

I turned for the door, eager to leave.

"Allen, wait." She stopped me. "Did you know Jason's date last night? She looked really familiar, but I couldn't place her."

My heart caught in my throat. "No, I met her for the first time last night. She seemed nice, I think Jason really likes her."

"She did seem nice, didn't she. Oh well, it will come to me eventually. Good seeing you Allen. Drive home safely."

"Bye Mrs. T."

I turned about face and double timed it down the street to my car before Jason's mom placed how she recognized Allison. I finally made it home and passed out in my own bed. It was an amazing night, but I was drained, emotionally and physically.

Over the next few weeks, I was eager to see Jason again, but I had to pick up extra shifts at work to pay for that lingerie I charged on my credit card. I made sure to switch the billing to e-statements so my parents didn't see the charge and paid it off as soon as I made the money. I was skeptical when I bought it, but given the results of the evening, I think it's safe to say the gamble paid off.

After two weeks of hard work, I finally had a Friday off. I sat down to veg out in front of the TV and just relax. I had finally gotten into a show on Netflix when my cell phone buzzed. I shot a glance at the screen.

"Incoming call from Jason," it shined brightly in the dark room.

I picked it up and answered, "Hello?"

"Hey Al, it's Jason...so um, there's a party next Saturday..."


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31 Comments
1Martiniman1Martiniman20 days ago

Well chapter 1 was pretty hot & erotic. I liked all the girls at the dance getting to know Allison away from Jason…kept it very realistic. Where do we go from here? Does mom know?

Blackbear7Blackbear75 months ago

I loved so much. Unlike Jason, I would have given Allen money to buy what was needed. After that 1st night, been at Allison's side with breakfast the 1st chance I had. Allison can be my partner every time. Wheather she's Allen or Allison. Holding hands and kissing all the way.

Robincd1126Robincd11265 months ago

I loved this! TY!

mic1980devmic1980dev7 months ago

fucking hot story, great work and ideas, more friends should crossdress and help out

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