The Sexual Awakening Part 4: The Challenge SeXStoRY

Derek has challenged my manhood and his Ultimatum was this. I was to make sweet love to his deeply devoted Cheerleader girlfriend by the end of the school day which was already over. As I jogged up the steps a thought occurred to me. The women I've slept with so far have seen single or desperate. Mrs. Macy was sexually frustrated because her husband was away, Nadia was living under the yolk of her traditional Grandfather and Natalie...well it's hard to meet someone of substance when you take your clothes off for a living. Without thinking I burst into the main entrance and narrowly missed a collision with Vice Principle Harris. "Mr. O'Hare are you just getting here now?!" he asked. "Yes sorry Mr. Harris I hadva f****y emergency." I said lying through my teeth. "And do you have a note explaining this 'Emergency?" he asked. "No sorry." "Well I'm sorry too, because until a note is produced you'll have detention every day this week." "Ok sure whatever." I said in my haste. I darted down the main hall and saw Jennifer Woods setting up posters for the PTA Bake Sale. "Hey Jenny have you seen Missy Wright?" I asked. "Yeah she's in Mr. Crowe's music class this period." "Mr. Crowe right...thanks babe." as I turned Jenn blurted out "I wanna have your babies!" "Ok maybe later." I said dashing away. I found Mr. Crowe's Music lab and it was shut. "Shit, it's music appreciation week. They're doing Karaoke in the Auditorium." I dashed to the Auditorium and found the class occupying the front three rows and Missy was on stage. "Come on now, does anyone want to sing a duet with Missy?" Mr. Crowe asked his class. Missy looked around with a sad look on her face. "I'm sorry Missy, you'll have to go by yourself." "I'll sing with you Missy." I spoke up without thinking. "You are not in this class Mr. O'Hare!" Mr. Crowe said looking at me from behind his huge glasses. "I know sir I have a free period and I um...just felt the urge to sing." "Fine!" he said putting down his pen. I climbed up the steps and stood next to Missy in front of the Karaoke machine. "Can you even sing?" Missy asked covering her microphone. "I'm acceptable." I said covering my own. Missy tapped the button labeled "Duets" and started scrolling. "Oh do you mind if I choose?" I asked "Fine go ahead." she said. I tapped on a song I liked and it started. "Crusin' in the style of Huey Lewis and Gwyneth Paltrow' I've never even heard of this song!" she said annoyed. "You'll like it, trust me." "My part's in blue, your's is in pink and together is purple." "I know how to sing a Duet in Karaoke!" "Ready?" I asked holding out my hand. "As I'll ever be." she said taking it. When we first started the class was goofing off and heckling us, but by the end they were silent. Mr. Crowe stood and clapped wildly. "Mr. O'Hare, why didn't you tell me you could sing so amazingly?" "I never really had the confidence until recently." I said. Missy was still clutching my hand from the Duet. "You were always so quiet, who knew!" Missy said all bubbily. As the class sat in silence the bell rang. "That's the end of class my Musical Enthusiasts, until next time!" I walked out with Missy at me heels. "Cameron wait!" she said. "Yeah?" I said. "Can we go somewhere and talk?" she asked. "Sure...where?" "The Auxiliary Room." she said with a smile. The Auxiliary Room had a dubious reputation in our school. To the teachers it was a storage facility for junk but to the students it was "Inspiration Point" a dark hole for all manner of sexual encounters. Missy opened the door with a hidden key and we slipped in. "I've never been in this room before." I said. "Follow me, I know just the place." she said taking my hand. I was led to a corner full of furniture from the previous year's play Peter Pan, tucked into the corner was a king size bed and mattress. "Come here." Missy said tapping on the space next to her. I sat down and she put her and on my thigh and started moving it closer to my crotch. "What are you doing?" I asked. "What do you think?" she said with a smile. "But what about Derek?" I asked. "Oh yeah Derek! We'll here's the thing about Derek." She held up her hand and wiggled it from side to side. "No way!" a said sligntly giggling. "Yep, I'm a beard can you believe it!" She said. "Why do you put up with it?" I askes. "Derek's f****y is loaded. He told me he'd convince his dad to give me the Silver f****y Scholarship." "That bastard!" I said. "What?" she asked. "He kept a beautiful woman like you on a leash, preying on your desire to go to college." "He did didn't he?" she said slightly annoyed. "We gotta do something about that." "What do you have in mind?" she asked. I unzipped my pants then pulled out my trusty iPhone. "Let's make a video!" I could feel myself changing but I didn't care. The meek dweeb I was was being pushed aside and replaced with a confident and sexually active Doppelgänger. I held out my phone and recoded Missy as she grabbed my cock and guided it inside her pussy. She put her hands behind her head and held her hair and she began to bounce up and down faster and faster. She let out a loud moan then quickly reigned herself back. She reached for the phone and turned it on me as I grabbed her hips, helping her to find the perfect satisfactory rhythm. Missy looked right at the camera and smiled. "This is how you Fuck someone, Derek Silver you Gay Asshole!" She dropped the phone on the bed and moved down to face me. She started licking my neck and with little kisses moved to my lips. It took me a minute to realise that we had gone beyond simple fucking, we were making love. I wrapped my arms around her and we fell into eachothers embrace. We actually came at the same time, we were in perfect synchronisity. As we lay in each others arms I heard Missy quietly sobbing. "Hey what's wrong?" I asked. "He was never gonna get me the Scholarship was he?" she asked. "Probably not, guys like Derek don't do things for other people. They are experts at using." "Now I'll never be able to go to college!" Missy said. "I have an idea about that." I said with a smirk. "What is it?" she asked. "Derek was so afraid of being gay that he hired you as his beard, why?" I asked. "His dad's really conservative. He would've disowned him if he found out his only son was gay. Why do you ask?" "I wonder how much Derek would pay to keep his fabulous secret." Missy looked at me accusingly. "You're talking about Blackmail...I like it!" As the last bell of the day rang I met Derek by his car, unlike before he was alone. "So how'd it go Sissy? Strike out." I walked over close to him and out of earshot. "I feel sorry for you Derek?" I said patting his shoulder. "Why?" he asked. "You're so afraid of your Daddy, the conservative republican that you've buried yourself so deep in the closet and even resorted to hiring an impressionable girl to be your straight camouflage!" "What...what are you talking about?" he asked visually shaken. "Missy told me everything Derek. About how you're gay and you promissed her the f****y scholarship in exchange for her being your beard. But you were never really gonna get the scholarship for her, were you?" "I couldn't...my dad said it would be a conflict of interest." "Oh that's to bad, but luckly you've got a trust fund." Derek looked at me. "You're blackmailing me, I could beat you right here and.." "I'm gonna stop you right there Derek and draw your attention to Missy who is standing over there." I pointed to Missy who was standing at the top steps next to the schools entrance. "Missy has a copy of this video ready to upload to Porntube. It's us Fucking in the Auxiliary room followed by a rather lengthy clip of you relating a sexual liaison with a big Bear Latino named Antonio." Derek looked at Missy then back to me. "Fine what do you want?" he said. "I want you to transfer $300 thousand of your trust to Missy's bank account, here's the info." I said handing him an account number. "Fine I'll do it." he said. "What do you think I'm stupid, call your banker and do it now." Derek pulled out his cell and made the arrangements. "It's done now what about the video?" he asked. "I'm gonna keep it for four years until Missy graduates, then I'll delete it." I turned and gave a thumbs up to Missy who started jumping and giggling. "Derek." I said turning. "Don't be afraid of who you are. You're Dad's a bigot and a creep for causing you to hide who you are. I promise your secret is safe with me but you should seriously consider telling him and having the chips fall where they may. On the other hand, college is where people usually begin to experiment." I said with a wink. "So it's done then?" Missy asked. "Yep and it has a rider that prevents him from removing it." "I kinda feel sorry for him Cameron." she said. "Yeah I do to, I can't imagine being that afraid." "At least I have a good guy, who does he have?" Missy asked. "Hopefully...Antonio." Missy smiled and moved in to kiss me. "Missy what are you doing?" Amy a snobbish Cheerleader asked. "I'm kissing my new Boyfriend, what does it look like Amy?" she said. "But that's Cameron O'Hare!?" Amy said. "Yes thank you now go away!" Missy said ushering her friend away. "You wanna stay and watch practice?" she asked. I followed Missy to the Field and she pointed me to a section of the bleachers where the Cheerleader boyfriends sit. "Go on up and enjoy the show." she said pecking my cheek. "Hello gentleman." I said sitting down among the human mountians known as my peers. "I think you're lost Twip!" One craggy peak whose letterman jacket read "Houser" said. "I'm invited Mr. Houser." I said pointing to Missy who blew me a kiss. "Oh in that case welcome!" he said his attitude changing. "I'm Doug, Tammy is my Boo. That's Sean his girl is Meg, Brock belongs to Amy..." "Oh Amy...met her, nice girl very sweet!" I said. "Duke is with Marion..." This continued for about ten more minutes so I'll just skip ahead. "And that brings us to you." he said. "Oh I'm Cameron O'Hare, boyfriend of Missy Wright." I said pointing to her standing at the top of the tower with her arms raised. "Good I never liked Derek, to much of an ego. He gave jocks a bad name!" I was amazed at how things could change so quickly, I was a shy loner only four days ago and now I have friends and a girlfriend. Little did I know that when you play with emotions you eventually end up gettjng burned. To Be Cumtinued...