High School Confidential

Lost in the sensual sensations, I let myself lay back on the bed as my cock got polished over and over. Part of me felt like she was going to do this all night, and that thought made me smile.

"What are you grinning at mister?"

I was so lost in my thoughts I didn't even notice she stopped sucking... mind you her hands were still sliding up and down, covered in saliva.

"I don't think I've ever been this happy as I am with you." I tilted my head so I could see her face.

"Says the man getting his cock worshipped and polished." She giggled.

"True... but it's more than that. This...you... how I feel; it just feels right." Our eyes connected and I was hoping she could see my sincerity.

"You mean that Shawn?" She inquired with my cock beside her face. Shit my cock was bigger than her head!

I nodded. "With all my heart Alasandra."

She gave my crown a big kiss then released it. She slowly crawled up the bed and straddled my stomach and lowered her face to mine.

"Say it again." She stared into my eyes.

I was trying to figure out what she wanted me to repeat... and it hit me. "It feels right."

She kissed me passionately and wrapped her arms around my neck. I could feel her leading me to her right, so I followed, and our bodies flipped positions with me on top of her.

"Two things..." She kissed me. "My name is still Alex, short for Alexandria. I made up Alasandra for tonight." She kissed my surprised face. "And secondly..." she paused her kissing. "I need you to fuck me, Shawn."

I'm sure my face was plastered with surprise and maybe even a little fear. "Fuck you? I... I don't think that's wise Alex." I could see her disappointment. "I couldn't stand hurting you. I can barely get into a vagina." Her smile returned.

"Ok... so let me ask you this. If we were able to guarantee you wouldn't hurt me, would you want to fuck me?"

"Alex, it wouldn't be poss..." She put her hand on my mouth.

"Shhh! I asked you a hypothetical question. If we could guarantee that it wouldn't hurt me, would you fuck me?"

"Yes."

"Even though I have a cock, you'd still fuck me?"

"I never even thought of that... but yes! You are the most beautiful woman I've ever met!" Her eyes were beginning to water. "Not to mention you've got the sexiest ass ever! It screams fuck me!" I added for good measure, and she giggled, breaking her emotional trend.

After a shared chuckle she tapped her finger into my chest. "Get off me.... We're doing this!"

Before I could even refute her, she slid out from underneath me and ran to the bathroom. She came back with a little overnight bag and pulled out a big bottle of lube. She held it up and grinned at me.

"A lady always comes prepared." She smiled.

I put my hands up to protest, but she was having nothing of it. "Ok... Shawn, just shut up for a minute... ok?" I nodded. "I don't like to talk about it, but I did do porn. I'm not a virgin back there and I worked with some pretty big guys. Granted, you're still at the top of the food chain, but I've had some experience." I was about to speak, but she put her hand up. "It has been a long time since then, but I did purchase a toy that I've survived on over these years. Again, not quite in your category but I've been fucking myself with it regularly... and every time, I imagine it's you." She crawled onto the bed and shimmied right up to my face. "I even named it... Shoop."

After a small stare off, we both began to giggle, and she gave me a slap.

"Shut up! It's true! Can't a girl fantasize?"

She crawled on all fours back onto the bed and knelt beside me. She handed me the bottle and proceeded to remove her bra and my cock jumped when they popped into clear view. I knew they were fake, but they looked real on her... like they were always supposed to be there.

"So... I don't have to take my panties off, I could just push the fabric to the side, you know, if that's more comfortable." She looked nervous.

"I already said your perfect. You don't need to hide anything about you." I assured her.

She bent over and pulled them down to her knees then lifted those to slip them off her feet. She was back up on her knees and I got my first look at the core of her apprehension. It was small... very small and hairless. Her balls were up and tight, almost invisible underneath.

"I've been on some hormones for awhile, so it shrunk even more... it doesn't even get hard anymore."

I looked to her face. "Are you ok with that? I mean, do you... can you still feel pleasure?"

She smiled at my lack of knowledge. "I don't need an erection to have an orgasm silly. Prostate orgasms are far more fulfilling in their intensity and duration. Did you know girls like me could actually have multiple orgasms?" I shook my head. "In fairness, neither did I, but it's true. So, are you ok with this?" She gestured to her tiny penis.

"Personally, I think it suits you. Makes you more exotic and sexier." She grinned at that response.

She grabbed the lube and started pouring some into her hands and she began applying it to my hard cock, which hadn't lost any blood to this point. I saw her take one hand and work a generous amount of lube in and around her ass, then she repositioned herself in a straddle over my hips. She sat her ass down on my cock and forced it flat to my stomach. She slowly slid and gyrated her ass around the head and the feelings were amazing! After a few minutes she bent down, kissed me, then sat up and raised herself up with one leg and tried to line things up, but it wasn't working. She stood up and this time lowered herself in a squat.

"Your too fucking big to line up like that. Take my hand and support me, ok?"

I nodded as I took her left hand, while her right, reached back and placed my crown right against her back door. She moaned at the contact and slowly brought her other hand for my support.

"Now listen to me Shawn. You're going to see me wince and hear me gasp and swear, BUT... I'm in control. Everything I feel will be my choice, so... don't panic or get worried. IF, and that's a big IF, I can't get it to go... I'll stop. Ok?" I nodded my head and she smiled.

For the next few minutes, I watched her swivel and grind herself, trying to ease my huge crown into her ass. She had to reach back a few more times, to help with the alignment. She was persistent if not committed. After her last re-alignment, I could feel something start to stretch around my engorged head. I immediately looked at her face, which was a mixture of concentration and pain.

Then suddenly, I felt it! My cock lurched up into the hottest, tightest sensation, I ever felt... I could barely describe it. Alex let out a loud squeak and swore for a minute or two, but eventually I could see her face relax.

"God! You're so fucking big Shawn." She smiled and moaned when I flexed involuntarily. "Oooh! That felt good!"

She put more weight onto my hands and pulled her feet out one by one until her knees were now straddling me. She winced and took a few deep breaths and glared at me.

"You ok Shawn?" I nodded, but I'm sure she could see my nerves. "Relax... it's what I always wanted!"

She began moving up and down in small increments. Every down stroke caused her to wince and grunt, but she was determined. I was so caught up watching her reaction, I hadn't realized how much progress she made. With half my cock inside, she released my hands and placed them on my chest. She leaned forward and kissed me passionately, causing my cock to pulse, which in turn caused her to moan.

"You fill me up so deliciously Shawn." She kept working her ass down on my cock, adding some circles and gyrations. "I've spent that last ten years fantasizing about this moment." She dropped her head and moaned as she relentlessly continued her ride. "It's not every girl who gets to live out her fantasy." She moaned louder and growled as the last few inches snugged my pelvis against her ass.

"OH, FUCKING GOD! SO, FUCKING FULL... SOOOOO DEEP!"

She collapsed down onto my chest and was breathing heavily into my ear. "You ok Alex?" I was concerned.

"You ever wonder if you'll ever find that moment in your life when it's perfect? Like the moment when everything in your world makes sense?" She whispered calmly. "My moment is right here, right now. Filled beyond max with the greatest man, with the greatest cock in the whole world." She brought her face up and kissed my passionately.

By now her hips were rotating and flexing around the gigantic pole shoved up her ass. She sat back up and started lifting an inch or two and coming down heavy. Her face scrunched up like she was in pain, and I was about to say something, when she held her breath and grunted like a rutting animal. It took me a moment to realize that she was having an orgasm and I watched liquid leak out of her cock. The spurts coordinated with the clenching her body was doing on my cock.

"Oh, holy mother pucker! That was fucking intense!" She smiled as the contractions subsided. "You sure know how to make a girl feel good!" She smiled don at me.

"I didn't do a thing... it's all you." I returned her smile.

"We need to do something about that!" Like earlier I felt her pull me to the right and we rolled in sync, until I was on top, and her legs wrapped around my ass. "Fuck me Shawn... please!"

I let instinct take over and began with shallow thrusts. The friction was smooth but tight and my cock felt like it was caught in paradise. I pulled further out and did some shallow digging, until I was right at the exit with my head.

"Don't you fucking dare mister! I waited ten years to get you inside... it ain't leaving now. Now FUCK ME!"

I don't know what snapped. Was it the sensations? Her dirty talk? Was it just because it was her? I slammed balls deep in one push and watched her head fly back as she screamed my name!

"Oh, Shhhhaaaawwwwnnnn!!"

Again and again, I hammered in and out of her ass. She grabbed her knees and pulled back, so I assisted by putting them over my arms. Not only had I never been able to fuck a girl in this position, but I had never been able to thrust so hard and so deep.

"Fuck me Shawn. Pound my pussy!"

I dropped my head and piled drove her ass for all it was worth. The loud slapping sounds were so ridiculous, you'd think I was slapping her silly.

"Yes! Like that! Harder Shawn... HARDER!"

The bed was squeaking so loud, it sounded like a rusty wheel going round and round. I had never fucked anyone or anything so hard in my life. All my pent-up emotions, all of my control and caution, were dashed and I rutted like a wild animal!

"God, you feel so good! Alex... oh, so fucking tight!"

The hotel phone rang, and we both stopped for a second to look at it, then each other. "Front desk?" I asked.

"They can kick me out, I don't care. There's no way we're stopping now." She gave me a wicked smile. "Fuck me like a bitch!"

Soon the room was re-filled with the sounds of rusty springs, moans, and body slapping. I drove into her stretched out bum hole over and over, lost in lust... lost in love? Right, at the moment of that epiphany, I thrust deep one last time and ground myself into her body like I wanted to push her through the noisy mattress. The minute my cum flew out, Alex screamed and bit into my arm, trying to keep the cops from showing up. I could feel her ass contract around my cock as my jets of cum continued to flow into her deepest areas. After, what felt like forever, we both started to come down from our high. She released my arm from her mouth, and I eased her legs from my arms. Once again, her legs wrapped around my ass as we laid together in a sweaty pile of happiness. I kissed her gently and our tongues played with each other until the phone rang again, this time we both chuckled.

I looked at her and she nodded, so still glued together as one, I reached for the phone and handed it to her.

"Hello?"

Her voice cracked which made me chuckle and earned me a slap. I could vaguely hear the voice talk about noise and complaints and Alex smiled through the whole thing.

"I'm really sorry. I just got the shit fucked out of me by a god... so yeah, not my fault. By the way, how old are these beds? They squeak like they came from the dynasty era." She stifled a full out laugh. "Yes, yes of course. My apologies." She handed me the phone and I hung it up.

"Manager says hi and was wondering if you could fuck her ass in the morning." She teased me.

"Sorry, my dance card is full." I grinned.

We lingered in the shower using an entire hotel's worth of hot water. We kissed, we hugged, we massaged and soaped each other... it was the most intimate shower of my life to say the least. Begrudgingly I turned off the water as she pulled the curtain back and grabbed us some towels. I dried her hair, while she "dried" my cock and balls.

"Keep that up and we'll be back in here washing off round two." I teased her and patted her bum.

"Oh god that would be so awesome... but I think my booty needs a few hours to recover. I am hungry though."

"Does this place have room service... or we could order in a pizza? What do you feel like?" We walked back into the main room still towelling ourselves off.

"You order what you like... I plan to eat in." She winked and licked her lips as she looked down to my cock.

**

We ate pizza and sipped our cokes, lying on the bed naked. Even without her clothes and makeup, she was strikingly beautiful. I was lost in her beauty and my silence got her attention.

"What are you looking at mister?" She teased.

"Perfection." I countered. Clearly, she wasn't expecting that, and she shut down in a serious blush. "You want to go somewhere?" I blurted out, even surprising myself.

"Like where? You want to go to a bar or something? I think everything is closed now."

"No. I meant somewhere besides here or going back to our homes." I could see her concerned look.

"I don't think running away is realistic for either of us Shawn." She insisted.

"I'm not talking about running away. I'm talking about going away... for a week or a weekend." I had her attention now. "I hope I'm not misreading this Alex, but I'm not ready for this to end. You're between jobs, I have a ton of vacation I could use... we could just go somewhere and be ourselves."

She sipped her pop and smiled softly. "That does sound incredible..."

I waited for the but...

"But... what's the long-term plan Shawn? We go away for a week of bliss then go back to our old lives? I'm struggling with seeing you leave after tonight, never mind a whole week or weekend. I don't think my heart could take it again."

Her mood had shifted quickly, and the weight of our situation became very heavy.

"I didn't know what to expect this weekend, Shawn. At worst I thought you'd out right reject me... at best I thought we could leave on amicable terms. But this.... I didn't expect and my emotions are all over the place right now. Part of me wants to stay and hold on to you, well another part tells me to run away now before my heart gets broken... again."

She rose from the bed and grabbed some clothes from the floor and went to the bathroom. As I watched her, I couldn't help but feel a huge sense of loss. Her feelings for me were clear, but what were mine? She clearly had a place in my heart, but was I ready to break things off with Lucy? We weren't kids anymore and I had to stop living my life day to day, expecting everything would just find a way to work itself out.

I got dressed and waited on the edge of the bed for Alex to return. I was about to knock on the door to check on her when she came out wearing a baggy sweatshirt and joggers. Even in the most unflattering clothes, she still looked amazing. She slowly walked to the bed and sat beside me, leaning her head on my right shoulder.

"I'm sorry Shawn. I had no idea this was going to end up being so difficult. I should've listened to my mom and never came to this thing." She sighed heavily.

"Me neither. I didn't expect any of this Alex." I took a few seconds to put my words together." Where are you going from here?"

"To Madison... I promised my mom I'd go up for a visit. It's been a number of years."

I have no idea how long we sat in silence. I think we were both terrified of saying our last words. It took all that I had to get myself to leave and the good-bye at the door was heart wrenching. I thought not being able to say good-bye the first time was hard, but it turns out that having that chance is just as bad. I drove home in a trance like state and proceeded to pack up my stuff. My parents were distressed at my behaviour and as much as I wanted to tell them about Lucy, about Alex... I knew it wasn't the right time and place. With all the hugs out of the way, I headed to the airport in hopes I could switch my flight and head back first thing.

I sat in the departures area, lost in my sorrow. I was hungry but I didn't feel like getting up was worth the effort. So, I sat there and sulked. Why was I such a mess? Why was my life so difficult? I was always the guy who had everything and right now I felt like the guy who lost everything. I lost my confidence, my will, my girl... WAIT. My girl? It took me a moment to realize that when I thought about losing my girl, I wasn't thinking about Lucy. I was thinking about Alex!

"FUCK! I'm such an idiot!" I swore out loud, scaring a few other waiting passengers.

"Must be a girl."

I looked to the voice. It was an older man, three seats over from me. "Pardon?" I asked him.

"Anytime a man yells out loud for no reason, it's likely because of a woman. At least that's been my experience." He snickered.

I smiled at the old man. "Well, you'd be right. I wish they came with a manual." I joked.

"Oh, they do son... just like everything else we do, we treat the instructions or manual as a suggestion."

I chuckled at the old man's assessment. Again, he wasn't wrong.

"Never too late to refer back to the manual you know."

His look spoke to me. I could fix this! I knew Lucy was the safe bet, but she wasn't what my life needed, especially after finding her in bed with an old college fuckbuddy. I needed unfiltered passion! I needed someone who could love me for all my gifts and all my faults... and I wanted to do that in return. I wanted Alex in my life... wait, no. I NEEDED Alex in my life! FUCK! I didn't even think to get her phone number, email... nothing!

*American Airlines Flight 219 to Madison Wisconsin, now boarding at gate 23. All confirmed passengers are asked to proceed to gate 23. That's American Airlines flight 219 To Madison Wisconsin, now boarding gate 23*

Could it be? What are the odds? I looked up to my departure gate... 16. Shit! Without a word I bolted from my seat and began may race to gate 23.

"Go get her tiger!" The old man yelled after me.

I guess the sight of a large man running full speed was intimidating, as the space in front of me seemed to clear like a parting of the Red Sea. I assessed the gate numbers as I blew by and of course gate 16 was stretched out around a corner. I just missed a man with his chid in a stroller...

"SORRY!" I yelled back.

There it was... gate 16. I slowed down as the people around me watched my approach. The areas looked sparse... shit! Did I miss her? Was she even on this flight? I bent over and put my hands on my knees to catch my breath. There was no one else moving to the gate and I lost hope in my so-called divine intervention.

"Wait! Please... wait! I'm coming!"

I turned my head to the source of the desperate call. A petite, dark haired woman was running with her bag on her shoulder and long wind breaker flowing open from her hustle.

I looked closer as the woman reared up at the gate entrance and fished for her boarding pass in her bag.