High School: Zero to Hero Ch. 03

"Jenn, Your mother and I have headed to Capital City for the night. The house is yours. Invite whomever you want, but don't let things get out of control. Remember, this is a privilege. Love, Mom and Dad." Privilege was underlined and retraced a few times for emphasis.

Before anyone went in Jenn made the announcement to the group and everyone cheered. The girls all filed into Jenn's room and the bathroom to change into casual clothes left there earlier. The guys stripped out of our suits wherever we could. I found myself in the kitchen.

"Whoops," I heard someone say from behind me.

I turned to see Heather shielding her eyes, as I pulled on a pair of flannel pants over my boxers. "It's okay. I have pants on now," I said jokingly.

"Thanks again for a wonderful time," Heather said sheepishly looking down at her feet.

"The pleasure was all mine. Thank you for allowing me to escort you tonight, and congratulations once again on being elected homecoming queen," I gave her a warm smile.

"Thanks," she said with a smile of her own, finally making eye contact with me. "You too."

I pulled a loose t-shirt on over my head and then the two of us made our way up to the TV room to join the rest of the group.

As a group, we enjoyed some movies, board games, and had ourselves a pretty good time. We had some late night pizza and put into the DVD player what we expected to be our last movie before going to sleep. About halfway through the movie most people had already nodded off. I had started to nod off myself.

As the movie wrapped up I got up and stretched. I looked around and everyone was asleep. Doug was on the one couch wedged between the twins. His body was twisted and contorted, and he looked to be somewhat uncomfortable, but I doubt he minded. Sarah and Jenn were curled up next to each other sharing a blanket. The rest of the group was either splayed out on the floor, on a couch or on a beanbag chair. Seeing as I was the only one awake, I decided to grab a bite to eat before finding a place to lie down.

As I warmed up a slice of pizza, I got the feeling I wasn't alone. I turned to see Heather shuffling into the kitchen.

"Hello, sleepy head," I said.

"Hi," she mumbled. "I couldn't get comfortable on the couch," she continued. "Doug and the twins are taking up the whole thing."

"Yeah. Same here," I said as I gave her a once over. She had on a pair of flannel pants and a tank top. I could tell she wasn't wearing a bra and her nice ample tits were stretching the thin fabric. I flashed back to seeing her earlier in the night all dolled up in her strapless dress. I stole more than a few peaks at her cleavage. Who wouldn't?

"Any ideas where you were going to sleep?" She asked while I finished up the last bite of my reheated pizza.

"Well, most people are asleep upstairs," I told her, "but I know something most of them don't know since I've been here before."

"What's that?" She asked.

"Follow me." I motioned her to follow me, and we headed down the hallway towards the back of the house. I opened the last door and ushered Heather in ahead of me. "The guest bedroom suite." It was a modest bedroom, not as big as a master bedroom, but a little bigger than Jenn's standard size room. It also had it's own bathroom. I'd stayed in it for a week when I was younger. My mom and step dad had gone out of town, and Jenn's parents agreed to watch me. "It's all yours," I said.

"What if I don't want it to be all mine?" She said with a twinkle in her eye. "What if I want to share it -- with you?"

"Does the queen want to share her royal bed with her king?" I said in my terrible British accent. She giggled which I took for a yes. I then took a step forward and gave her a gentle, yet passionate kiss.

"Just let me freshen up first," she said. While she took care of whatever she needed to in the bathroom while I went out and turned off the rest of the lights in the kitchen and hallway. I also shut and locked the door to the guest suite to prevent any unwanted intruders, in case someone got to exploring in the middle of the night. I also dimmed the lights.

When I turned to face the bed, Heather was already under the covers. I smiled and took a few steps closer to the bed. I looked at her as she watched me and saw a mix of anticipation and uncertainty. I figured I would do my best to reassure her.

"We don't have to do anything you're not comfortable with," I told her.

"I want this," she said as if she was trying to reassure herself. Since I wasn't entirely convinced, I sat down on the bed next to her rather than climb under the covers.

"Can I ask you something very personal Heather?" I made sure to use a sincere and endearing tone.

"Yes," she said nodding her head.

"Are you a virgin?" I asked. She blushed which was enough of an answer for me. "That's okay," I said brushing the hair back from her face. "I don't want you to feel like you have to do anything with me tonight. I had a lot of fun tonight and value our relationship. I am very lucky to have you as a friend." She blushed again. She was usually a more confident person. Her reputation on the field hockey team was that of a strong willed player with a confident air about her. This was not at all how I expected her to act with a guy.

"I do want this," she said firmly. "I want you do be my first guy." She then looked up at me with an expectant look on her face, as if she was afraid to be rejected by me.

"Why me?" I asked. "We're not dating. We haven't even hung out before tonight. I'm not really anything special, or popular."

"You are the nicest, sweetest guy I have ever met," she said taking my hand in both of hers. "There are a hundred girls at school that would do anything they could to be here with you tonight," she paused, "I want you to be my first because I feel I can trust you -- and you're mature. Most of the other guys are jerks and probably would have been all over me hours ago." She got a dejected look and broke eye contact for a while. I sat and listened to her words, and to what she was not saying. "I don't want my first time to be with some jackass who doesn't know what he's doing while we're in the back of his mom's car. I want it to be special. I want it to be with someone I like to be around." She stopped for a second. "Even if you and I never talk to each other again, I can remember the night I was elected homecoming queen and got to spend the night with the homecoming king. Not only that, I got to spend the night with Steve Smith," she smiled a big Cheshire grin.

"Well," I said, "my lady, I am at your service." I stood up and took a bow. She giggled again.

It was hard to take my time stripping and trying to be seductive, since I was only wearing a t-shirt and flannel pants, but I did my best to be patient. When I was down to my boxers, I slowly climbed into bed next to Heather. I could already feel the warmth of her body heat as it radiated under the covers. I shimmied closer and felt bare skin against my arms and legs. She had obviously already taken off most of her clothes.

"I told you I wanted this," she said as we embraced under the covers. I felt her breasts press against my chest, particularly her erect nipples that betrayed her readiness.

"I want this too," I said just before our lips met.

We kissed and fondled each other. I discovered that not only had she removed her outer clothes she wasn't wearing any panties as well.

"My lady," I said my fake British accent. "I must regretfully inform you that I am going to embark on a quest."

"A quest?" She asked trying to match my horrible British accent.

"Yes, my lady. I am going on a quest to the holy lands in search of a powerful relic," I said.

She giggled. "And what relic is this?"

"I am going find the fabled female clitoris," I explained. I then threw the covers up and dove under them. I showered her neck with kisses and poked and prodded my way down her body. "Is this it?" I said as I grabbed her elbow. She laughed and told me it wasn't. I then grabbed her hand and sucked one of her fingers into my mouth. "Is this it?" She again laughed and told me no. "I didn't think so either." I moved across her body and took each of her breasts in my hands as I straddled her waist. "Maybe these great orbs of wisdom will grant me the knowledge I need to find the clitoris." I then massaged, and squeezed her ample tits. Based on what Ashley told me, I made a guess that Heather was a full D cup. They were bigger and rounder than Ashley's C-cup breasts and drooped a little, but still retained their youthful firmness. I leaned down and took one nipple in her mouth and she let out an appreciative moan.

"That feels so good," she cooed and then bit her lower lip in a sultry sexy way that drove me crazy.

"Is this it?" I said giving her nipple a pinch.

"No," she said between breaths, "but you're on the right track."

"Excellent," I said before locking my lips around her other nipple. I continued playing with her nipples and breasts for a while longer. My goal was to get her sufficiently turned on that her first time wouldn't be as painful. 'Foreplay is essential,' I could hear Ashley saying in the back of my mind.

I worked my way down her body and kissed her belly button. "Is this it?" She moaned that I was getting closer. I kissed my way down across her bikini line and planted a kiss at the top of her pussy.

"So close," she moaned.

I ran my tongue down the folds between her pussy lips. She was very aroused and her pussy was nearly dripping with fluid. When I traced my tongue back up her slit I let it graze the tip of her clit. She gasped for air and moaned.

"That's it, my lord," she moaned again.

I took that as my cue and began my assault on her clit. I ran through the alphabet twice and milked two orgasms from Heather's pussy the second time through. I also poked and prodded her pussy with my fingers and found no resistance and suspected she had already lost her hymen some other way than intercourse. She must have figured out what I was thinking.

"I already broke my hymen," she moaned, "with my hairbrush."

"My queen is a naughty girl," I said as I came up to her level again. "Is my queen ready to become a naughty woman?" I asked as I leaned down to kiss her.

"Make me a woman," Heather cooed.

"As you wish," I said. We kissed passionately and our tongues darted back and forth in each other's mouth. I rolled over onto my back and pulled Heather on top of me.

"I'll let you be in control," I whispered.

She smiled and worked her way down under the covers. She pulled my boxers off and tossed them out the side of the bed. I felt her hands caress my dick followed shortly by her mouth. She may have been a virgin, but when it came to blow jobs, she knew what she was doing. She brought me near the edge and backed off a few times. She licked the length of my shaft at one point and then proceeded to suck each of my balls into her mouth.

I was already use to shaving the edges of my pubic hair for swimming but Ashley encouraged me to start waxing since it would save time and keep me smoother longer. The first time I did my balls I nearly cried. After a while, the amount of hair was manageable enough, and I got used to the pain. I was completely smooth for Heather.

"I've never gone down on a guy this smooth before," she said when she finally came out from under the covers. "I wish more guys did that." I wondered where she got so much experience to make that judgement.

We kissed again as Heather straddled my waist and ground her wet pussy against my hard dick. She moaned as her clit brushed against the shaft of my rigid cock.

"Thank you," she whispered as she slowly lowered herself onto me.

"No," I told her, "Thank you for the privilege and honor of being your first. My God, you feel wonderful."

We moaned in unison when she had the full length of my dick buried in her pussy. She sat there for a while without moving. I allowed her to take the time to get used to it. I reached up to her breasts and started to lightly pinch and fondle her nipples, and rub her areolas.

"So much better than the handle of my hairbrush," she moaned. "I can feel your pulse with my pussy. I can feel the heat. It's so big and hard." She let out a moan as she began slowly rocking her hips.

We worked up a rhythm until she was riding the full length of my dick. I also did my part to hold her up and work my hips. As a swimmer, I was very good at the butterfly. That's the one where you kick with both feet together at the same time. My coach nicknamed it the sex stroke because if you watched someone doing just the kicking part, their hips were moving forwards and backwards as in intercourse. Maybe that's why I was such a natural lover according to Ashley. Either way, Heather was enjoying her first time, and had climaxed twice already.

"I want you to cum in me," she cried out. "I'm on the pill," she moaned. "I want you to fill my little virgin pussy with you sperm." That was enough for me; I could feel my balls start to boil.

"All right, you naughty woman," I moaned back at her. "Time for you to receive your first real load from a man." I thrust a few more times and then felt my balls constrict.

"Yes!" She cried out as she felt my first jet of cum wash down the walls of her vagina.

I thrust a few more times as I emptied my balls deep in her devirginized pussy.

She collapsed on top of me and then rolled off to my side. She nuzzled up next to me. "Thank you," she said.

"My pleasure," I said with a laugh.

"Oh, mine too," She giggled.

We lay in silence for a little while. I felt sweaty and thought a shower might be a good idea. "Any chance you want to take a shower real quick before we fall asleep?"

"Together?" She asked.

"Yes," I said with a mischievous smile.

The two of us made our way into the guest bathroom's shower. Heather knew enough to hold a hand over her full vagina so she didn't drip my juice onto the carpet. Since the basic premise of the guest sweet was an in-law room, the bathroom was elderly friendly. This meant the shower was oversized to accommodate a stool or a wheelchair. This gave Heather and I ample room to move around and continue to explore each others bodies. I washed her hair which she found to be quite a turn on. In turn, she dropped to her knees in the shower and gave me another expert level blow job, allowing me to spray my load all over her lovely breasts.

We fell asleep in each other's arms and woke up around noon on Sunday to the sounds of people in the kitchen. We got dressed, put fresh linens on the bed, exchanged one last kiss, and then rejoined the rest of the group.

+++

No one said a word about Heather and me emerging from the guest room the next morning. Jenn and Sarah each gave me a wink and a smile. At least they knew and were cool with it.

From noon until dinner time people slowly left Jenn's house and made their way back to the homes. The next day would shock us back to reality with another day of school and end our weekend-long homecoming celebration.

I dropped Heather off on my way home and was more than happy to crawl into my own bed. I made sure to call Ashley and give her all the details of my night with Heather. I also got a text from Jenn telling me to log onto my yahoo account.

"Incoming video invitation from jennyflower82," the message read on my computer screen. I hit accept and the screen switched to a video feed of Jenn sitting in her room.

"Hi honey," she said waving at me through the computer.

"Hi babe," I replied as I adjusted my own webcam to get a better line on my face.

"I want details," Jenn said as she brought her knees up to her chest and made herself into a little ball.

"About Heather?" I asked

"Yeah," she said nodding her head. "Spill it."

"You know I don't like to kiss and tell," I said with a laugh.

"Oh," she said slightly dejected. "Here I was ready to masturbate on screen for you while you told me every wet, juicy, nasty detail," she paused as she pulled her top down enough for me to see one breast. "I guess I'll ping Sarah instead, and she and I can masturbate for each other and leave you to your own devices."

"Well, if you put it that way," I said thinking for a second. "Ping her anyway. I am sure she'll want the details too, so she might as well get them straight from me because I know you'll tell her." I was a little sarcastic in my tone.

After a few seconds I had both Sarah and Jenn on my screen. I started telling them about how I though Heather was pretty, and how I had really never thought of her in a sexual way. They both agreed that they through she was pretty and both were jealous of her bigger breasts. I reminded both girls that they had equally lovely bodies despite the subtle differences. I continued on with my story and as the details got hotter and juicer the girls clothing started to disappear and they started to play with themselves more and more. When I got to the part of the story where I orgasmed inside Heather, the three of us all climaxed together.

"That was hot," Sarah said. "We need to do this again."

"I agree. Not that we don't live five minutes from each other and can't see each other any time we want," I said jokingly.

"I recored the whole thing," Jenn said with an impish grin. "We can watch it next weekend if you guys want."

"I reminded both girls to be careful with any recordings and not to email each other the files so things didn't get snagged in mid air." The last thing I wanted was for anyone's reputation to get sullied, especially my own.