High School Confidential

I shook both of their hands. "So nice to see you girls again... and congratulations on your marriages. Any kids yet?" Shelley shook her head and Betty held up 2 fingers. "Wow! Imagine our group being adults and parents... makes me worry, I'm not sure about you two." They both smiled and giggled. It's a good feeling when your sarcasm doesn't fall flat.

I made my way to the gymnasium, not sure what to expect. I stepped through the doors and memory after memory raced through my head. People chanting my name.... it almost seemed like a dream now.

"Shoop you old hound dog! How the fuck are ya?!" I turned to the boisterous voice to see Peter, drink in hand and already three sheets to the wind.

"Hey Pete... good to see you." We shook hands, and he slapped my shoulder.

"Shoop... I'm sorry I was such an asshole our last year, well the last month for sure. I was a shitty friend and I hope you can forgive me."

I didn't expect that! You could have pushed my over with a feather... I was dumbfounded. "Uhm... ya. For sure Pete. We were both young and dumb. I could've handled myself better too." He seemed relieved with my response.

"Ah Shoop... still the man. Come on! We got a table going over here with most of the old gang.'' We started off in his gestured direction. "Shit it's good to see you! I was really hoping you'd come. No one's heard from you since grad. We followed you from a distance while you was in college, but then you just up and disappeared."

"I don't think it was quite that dramatic. I just moved forward. I work for a large green energy company in Boulder now... senior project manager." I felt a great deal of pride saying all that. "How about you? What are you up to?"

"Working at the plant. Got my old lady prego right out of high school. Working like a dog now to keep both my girls happy." He was smiling.

"Wait... you got a daughter?"

"Uh huh. She'll be 9 in 3 months." I think he could see the surprise on my face. "Go figure huh!" He smacked my back.

We showed up at the table and all the guys were there. Some had their girlfriends or wives; they all looked the same. A little balder, a little rounder, but they were still the same under it all. I carefully navigated my own personal life and left out that I was engaged... well kind of sort of. I was shocked that they all followed my wrestling in college. I couldn't explain why I had just got up and quit... hell I didn't even know myself; I just know I lost my passion. Even the call of the Olympics wasn't enough to get the fire going again.

My attention was pulled from the group when a woman caught my eye. She was wearing a blue silk pantsuit that had slits in the sides of the legs. Her bust was pushing on the thin material as she strutted past our table. Her Long black hair was up on onside with a delicate flower above her ear.... It was her! The girl from the woods! Watching her ass rock back and forth only confirmed my suspicion.

"Pete! Who's that? I don't recognizer her." Peter looked at the woman and shrugged is shoulders.

"No one knows. She's been talking to everyone like she knows us, but no one's come out to ask her. Her name tag says Alasandra. I don't think we even knew an Alasandra."

I have no idea why, but I bolted from my seat and tracked her down. Trying not to seem too weird, I slowly moseyed my way in her direction at the snack table.

"They put out a pretty good spread huh?" I opened with and she turned and smiled.

"Hey Shoop. It's nice to see you again." She knew me?

"Did I see you yesterday... up Flint Road, in the back area?" I asked.

"I thought that was you, but I wasn't sure, and I was pretty far out by myself."

"Yeah... can't be too careful." I smiled. "Look... Alasandra?" I motioned at her name tag. "Did we go to school together? I feel like a real idiot, but I don't remember an Alasandra."

She looked at me nervously. "Yeah... we did. I changed my name a few years back." She looked away, then deep into my eyes. "It's me Shawn... Alex."

Pick a metaphor... the floor fell out beneath me... I left my body... my head exploded... yeah, they all sounded right. Everything stopped. My chest got tight, my throat constricted, my heart was beating like it wanted to pop out of my chest.

"Shawn? Shawn? Shawn, are you ok?"

I was brought back to the moment from her voice. Her voice? How did I not know her voice? Her eyes... I can see it plain as day now. She... changed her hair color and added breasts but she was Alex!

"Jesus! Alex... I... shit! I have to sit down." I looked for the nearest chair and found a spot at an empty table right where we were.

Alex or Alasandra, sat next to me and put her hand on my lap. "I'm sorry Shawn. I didn't mean to freak you out."

It took me a few minutes to collect my thoughts and I wanted to yell at her, hug her... it was really her. "Alex... sorry... Alasandra, I'm not freaked out. I'm... I'm... I tried so hard to talk to you... to find you and you shut me out and left me." I was getting my traction back. "Why? Why would you do that?"

"Oh Shawn... there's no easy answer. I don't even know if I know why. I was hurt, embarrassed... angry."

"I was trying to help you. I wanted to be with you. Why would you be angry? I know what Ginger and her so called friends did was awful, hell I almost beat the shit out of the entire school for you!"

"You made me believe, ok!" She started to get emotional. "You made me believe I could exist in your world, and I wanted it so bad Shawn.... but it was just a stupid fantasy."

"You don't know that. You never gave it a chance." I could see she was hurting deep down just like me. "Look... can we get out of here and talk... like really talk? We can't do this here." I looked longingly into her eyes. She finally nodded and I stood up and extended my hand down to help her to her feet. She uncrossed her leg and stood with me, and we shared a look.

"There you are! Are you hiding from me Shoop? And who' this little minx?" Ginger had a knack for making bad entrances and saying the stupidest things. She looked to Alasandra. "Don't get any ideas sweetie. This big hunk still owes me a good prom fucking, right Shoop!" She looked at me and I could see very clearly that the last 10 years had aged the girl more than that.

"Go grab a broom stick Ginger and fuck yourself till you're full of splinters." My calm response took a few seconds to register in her head and when they did, Alasandra and I were already heading out the door.

We got into my mom's car and headed out.

"Fuck yourself with a broomstick? That was pretty harsh!" Alasandra giggled.

"Yeah, not my best moment, but she doesn't give a shit about anyone but herself. I should've told her off 10 years ago."

After a bit, I realized that I was unconsciously driving out to our spot, off Flint Road. I gave her a questioning smile and she gave me a soft one in return. We small talked our way out there, catching each other up on the last 10 years. She had followed my wrestling and was shocked when I gave it up and I still had no reasonable answer to that one. She and her family moved, again, shortly after grad and headed to Wisconsin. She was an army brat, which I had no idea, and her father was able to transfer fairly easy from office to office. It sounded like he was more into policy then actual deployments. After a few years there, she left home and headed to New York with a friend, where they both tried their hand at acting. She worked with a couple of small performing companies, but the bills were piling up, so she made a tough decision and did some amateur porn to pay the bills. Apparently, the demand for petite, white sissies or trans, was huge and she became very popular in the underground industry. I listened carefully and was very careful not to pass any judgement, but inside I was sad and angry for what she had to deal with.

"So, I did that for 4 years off and on. It paid the bills and allowed me to sock away some money for a few upgrades." She lifted both of her breasts to make her point.

"For what it's worth, I think they look really good... perfect for your body size." She gave me a coy smile.

"Thanks Shawn... that means a lot." She looked out the window. "I eventually got out and started doing some modelling, mostly just advertisement media stuff... apparently the camera likes me."

"It's not hard to see why." I added quickly.

"You must stop that, Shawn. You're making me feel all warm and fuzzy and that's dangerous." She gave me a serious look.

"I'm sorry Alasandra. I'm not trying to make things awkward for you, but you have to know how beautiful you are, I can't be the only one who's told you that?"

She went a little quiet. "Yeah, I've heard it a lot, usually before they ask me for sex."

I didn't have a comeback for that. It caught me off guard. We pulled into our old familiar spot, and I shut off the motor.

"What about you Shawn? I know you gave up on the Olympics but how was college? What are you doing now?"

I carefully walked her through my last 10 years. I revealed how hard it was to get motivated after what happened at prom. How I turned into a dumb jock in college, sticking my dick into as many girls as I could. Looking back, I was clearly using sex as a coping mechanism, but it likely made things worse. I told her about my career in green energy, my new position, and my home in Boulder. I told her that I wasn't planning on coming to the reunion, but I was pressured by my fiancé. The look on her face told me I could've brought that up way better than I just did.

"You... you're engaged?" She looked at me in surprise.

I nodded my head, and I could see her mood change. "I feel like I need to clarify something." I started, but she interrupted me.

"You don't have to Shawn. I don't know why I was surprised. You're the best man I know, why wouldn't a woman want to marry you." She wouldn't meet my eyes.

"Alasandra? Why did you come to the reunion? I mean I was mad at my friends, but you were barely here for 6 months and as far as I know, had only one or two friends. Why would you come to this?"

"I don't know. Marsha told me about it and at the last second, I thought why not? I doubted anyone would recognize me and I thought I could just... I don't know." She went silent for a minute. "I was hoping to see you. I wanted to apologize for how I left, and I wanted to hear about your life. I felt a real strong pull to come here, to this place." She gestured out the window. "It was like I was saying goodbye to you properly."

I put my hand on hers. "I get that. I think that's what drew me here yesterday too." I gave her hand a solid pat. "Now let me tell you about my real life." She turned to me with her eyes wide open.

I proceeded to tell her about Lucy and spared no details in how my last day at home was before I got here. I shared how I was feeling, and I guess for the first time I was being truthful with myself. I could see how I was making easy choices instead of looking for the real deal. Lucy was beautiful, she was smart, she put up with my cock, she was an easy decision. We were compatible in so many ways except for one big one... my big one.

"So, are you going to patch things up with her when you go home?" Alasandra looked at me with her big brown eyes.

"Honestly... I don't know. I'm not even sure I'm ready to go back. I got lots of vacation time, maybe I'll just visit mom and dad for a bit." I looked out my passenger window into the darkness. "What about you? Where are you off to from here?"

"Not sure actually. I'm in between things right now. My modelling career is getting less and less busy, and...." She paused.

"And what?"

"I don't want to have to go back to doing... that again."

She looked so vulnerable. "Then don't! You could be anything you want Alasandra. Look at you! You are absolutely stunning!" She turned and smiled at me, our eyes locked and that was it... before I even knew what I was doing, I was leaning in to kiss her.

She was surprised and very timid of my advancement, but she soon reciprocated my kiss. It was gentle and passionate. It was the best kiss of my life.

Alasandra slowly pulled away and looked at my eyes. "That's the first time you ever kissed me." She stated.

I chuckled at the revelation. She was right... the only kissing we did before was between my cock and her mouth. "I hope it was ok." I blushed slightly in embarrassment.

"Made my toes curl." She exhaled.

"Mine too."

She pushed up to me and we were making out like to high schoolers out for date. She was so passionate, and her lips and tongue knew just how to caress and tease mine. She placed her hands on my chest and moaned into my mouth. It was heaven... I had no ideas kissing could be this sensual. I felt one of her hands slide down my chest and rested on my now rock-hard cock, and she let out another little moan.

"Can I Shawn? Please..." She whispered into my mouth. My quick kiss gave her my answer.

She now had both hands on my zipper and with a little help from me lifting my ass, she had everything pushed down to my knees. She had my cock in her hand and she was soaking it in.

"Fuck I missed you Shawn... and I really missed this." She kissed the head, and it was my turn to moan. "I really miss your truck right now, too." She giggled and propped herself to lean over the center counsel and stuck her ass in the air as her head went down.

I pushed my seat back as far as it would go and my head flung back at the first warm, yet familiar sensation. It was like getting the first blowjob of my life, I was giddy and excited beyond belief as her magical mouth began it's long missed descension. I've always prided myself on my ability to keep my excitement under control, but I knew immediately that this wasn't going to last nearly as long as both of us wanted.

"Oh, fuck Alex... shit! Alasandra! It feels too good. I'm not going to last long!"

The information went straight to her actions, and she immediately started throating me right to the base. I was even raising my hips up, trying to push it in further. She snuck her right hand under my ass, and I could feel her finger probing my asshole. She paused like she was waiting for my reaction and when I moaned, she returned to her ministrations. Her head was bobbing up and down at various heights, but always back to the base, while her finger was pushing on my, tight as a ducks ass, sphincter.

She briefly removed her finger and wiped it in the collection of saliva on my pelvis and returned it to my pucker. My cock was tingling, and I knew I was close.

"Ala... Ala... I'm fucking close babe! So fucking CLOOOOOOSSSEEE!"

Her finger popped my cherry and that was all she wrote. I was going off like the fourth of July and I could hear her heavy swallows as she tried to keep up.

*GULP* *GULP* *GULP*

It was the only sound in the car, except for my moaning and whimpering as I slowly came down from my best orgasm in 10 years. Alasandra patiently waited me out and when she knew I was done she carefully released my spent cock and kissed the head again.

"I forgot how much you cum!" She smiled. "It's still my favorite meal." She giggled.

A short time later we were driving back to town and both of us were nervous about what was next. We small talked, but it was starting to feel forced. I made the decision... I wasn't going to blow it, again.

"So where are you staying? With Marsha?"

She laughed at me. "Marsha doesn't live here anymore either. I got a room at the Best Western. Not the fanciest place but it was affordable."

"Does it have a bar?"

"No, I don't think so. Why?"

"I don't know... I feel like it took me 10 years to see you again and I'm not anxious to call it a night." She smiled at me. "Maybe we can pick up a bottle of wine and you could invite me up for drinks? I gave my sweetest boyhood smile.

"She laughed at my poor attempt. "I'd like you to come up to my room, but I don't think we need any wine." She put her hand back on my cock. "I think you got all we need to have fun."

I followed her up the stairs and admired her bottom. It looked even rounder and firmer than it did 10 years ago.

"Are you checking out my ass Shoop?" She teased me.

"Guilty as charged!"

She let us into her room, and she told me to get comfortable while she went into the bathroom. I looked around the older room and saw the bed was at least king-sized. I loosened my shirt and sat on the end of the bed and turned on the TV. It still hadn't it me that this was real... meeting Alex (Alasandra), kissing, the blowjob... it felt dreamy. I heard the door to the bathroom open and what walked out turned my cock into instant steel... talk about dreamy!

Her black hair was free and hanging down to her ass, she wore matching bra and panties, both red, black and very lacy. Her boobs looked perfect sticking out and her panties were so small, I actually wondered if she had gender reconstruction surgery because there was no dick to be seen. Catching my look, she smiled at me.

"It's very small and currently tucked. Is it okay? I could put some leggings on or something." She was trying to feel me out.

"You look... perfect!"

She smiled her beautiful smile. Unlike Ginger, the years have been a blessing to her. She was all woman now, gone was any trace of masculinity.

"Well, someone is clearly overdressed at the moment." She cocked her hip and put her hand on it... fuck she was sexy!

I pulled my shirt off and then my socks. I stood up and slowly pulled my zipper down and shoved them down my legs and pulled them over my feet. She stood there, staring at me, and motioned to my underwear.

"But you're not completely naked." I teased her.

"Woman's prerogative, now lose them!" She ordered me.

Happy to comply, I pulled them down and off, standing there naked as the day I was born. Alasandra's eyes were already glued to my now rising cock.

"I swear you are the eighth wonder of the world Shawn... that cock is a masterpiece!"

Not that I needed an ego boost in that department, but it meant a lot coming from her. She glided towards me, wrapped both her hands around my cock and stroked my hard flesh. She looked into my eyes while she was doing it and I couldn't help but lean down to kiss her. She stopped me with her hand on my chest and gently pushed me, as my legs buckled on the end of the bed.

"Have a seat mister. Something tells me you won't be able to stand for this one." She was literally purring at me.

With my rump firmly planted on the bed, she knelt between my legs and licked her lips. The hunger in her eyes already had me charged up!

"I've dreamt of this Shawn. You and me... alone. Not like some sex hungry teenagers in a car, or locker room, but on a bed... with no distractions... no curfews... no time limits." She settled in stroking my hard as iron cock. "I bet now that we got the first one out of the way.... I could drag this out all night!" She lifted my cock and licked the underside of me engorged head. "Would you like that, Shawn?" Another slow lick. "An all-night blowjob? I know I would."

My mouth was frozen, I couldn't even make a squeak. I have no idea how she did it, but she had me hook, line and sinker. Whatever she was selling.... I was buying! She owned me.

"Ahhhhh! Oh FUCK!!"

Down she went, straight to the bottom in one fell swoop. She grabbed a ball in each tiny hand and gently pulled down as she slid her mouth and throat up and down my huge shaft. She'd stop at the crown every once and awhile, and slather it with her tongue and lips, before engulfing me in her sweet, tight throat. I watched as she weaved her magic upon my cock. I could never understand how she did this to me, and so effortlessly! She'd moan while she sucked and slurped, giving me a wink once and awhile. Her love for my cock was evident and the feelings were mutual.