My Sex Life: School Play

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I lose my virginity backstage in high school.
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This is the start of a series of fantasies based vaguely on my life. I don't know exactly how many parts it will be, but it won't be in chronological order although I will provide a list starting with the second one to indicate where things go. The next story I post will be the next part of 'Control: Who Wants It?'. This is a fantasy. All characters portrayed in this story are at least eighteen years of age. The characters depicted are both seniors in high school and are of legal age to be depicted in this story.

*

"All right, two minutes." It was my senior year of high school and I was about to go on stage for the final performance of Dracula's Revenge. I was playing the title role. I wasn't the tallest guy in my grade, although at five foot nine I was hardly short. As the title would suggest after being defeated (the play we did last year) he is revived by Renfield to get revenge on some unsavory relatives. I was in the green room just finished from makeup and I was going over my lines one last time when my friend Charlotte walked up to me. Charlotte is maybe an inch or two shorter than me, with dark eyes and long raven hair, she is no anorexic supermodel, but she looked healthy. I had had a crush on her since we met, strong personality as well as really hot. I have always been attracted to women with strong personalities, I don't want a girl to submit to me. She smiled and it was difficult to focus as she was dressed as a fetish dream nurse (or at least as close as you were going to get away with in a high school play. That being said the final performance was notorious for being a bit risqué as we could afford to take risks without fear of the play being cancelled. Charlotte's costume also included a riding crop (the idea was to hint that she was a dominatrix) and without warning she struck me from behind, several times. My ass was on fire and the fire spread to my groin as I felt my cock instantly harden and I was certain that it had never been harder in my life. I turned to her she laughed, although low so that we wouldn't disturb the performance.

"Charlotte, can you tell that I'm blushing?" She grinned wider.

"Yes, but don't worry it doesn't show on your face." I breathed a slow sigh of relief.

"Good, because my parents are in the audience and I don't really want them to ask why." She laughed again and led me off to the side out of the way. Without warning she grabbed my shirt and pulled me into a kiss. It wasn't until she broke the kiss abruptly that I actually stopped to think about the fact that we had never kissed, we were friends no more. At least that is what I always thought.

"Charlotte, wha...?" however before I could finish she put a finger to my mouth and shook her head while still smiling, but now there was a glint in her eye making the smile appear mischievous. Suddenly she dropped to a squatting position and lowered my pants before pulling out my painfully hard cock. My dick was by no means huge, about six inches, but she didn't look disappointed as she gave me one long lick up the length. A tingling ran up the length as she licked and I felt as if I was getting harder. She swirled her tongue around the head and I didn't think I could hold out for long. She abruptly stopped, looked up and whispered.

"Don't hold back, we don't have time." So I looked down at the cleavage her costume exposed and imagined her without the costume in an effort to cum quickly. In the back of my mind I vaguely thought about the fact that on stage was only a matter of feet away and anyone passing through could spot us despite the dim light backstage. She opened her mouth to engulf the head. Her mouth was so wet and warm and the look she gave me as she looked up was one of eager hunger. The speed increased as she worked her way down the shaft. She reached the base and I could feel her moving her tongue as she sucked. Suddenly her tongue hit as sensitive spot and I came down her throat. I kept coming and it seemed as if I continued without end. At last it ended.

Charlotte carefully cleaned me up and made a bit of a show of swallowing. She fixed my pants, stood and theatrically licked her lips. It was then that I got my cue to go onstage. It wasn't easy to be Dracula after a beautiful girl gives you a blowjob. However I managed to get through it without embarrassing myself. After the play I found Charlotte talking to my parents, who were trying to avoid looking disapproving of her outfit as they knew she was a very good friend of mine. As I approached Charlotte was the first to take notice and waved me over. As I reached them my mother turned to me.

"That was great. Charlotte has offered to drive you home afterward. Just don't be too loud when you come in." My mom was being quite reasonable about this because I was actually pretty shy, except when acting on stage and so they were happy to see me out with friends. Once my parents left I turned to Charlotte.

"Charlotte, what are you up to, I don't remember you saying anything about giving me a ride?" She leaned in and in a low voice spoke to me.

"I helped you out, I thought I'd give you a chance to make it up to me." So we changed out of our costumes and I washed the makeup of my face before she led me to her car. I was feeling nervous on the drive and then I realized I didn't actually know where we were going.

"Charlotte, where are we going?" She gave a faint smile as she focused on the road.

"I told you, I'm giving you a chance to return the favor." Knowing full well that she would be unfazed by it I glared at her.

"Charlotte that tells me the 'what' not the 'where'." Although I wasn't certain, I think she was laughing at me.

"Oh, I'm taking you home of course."

"What about your parents?"

"Gone for the weekend." She grinned before continuing. "I've got you all to myself." It only took a few minutes to reach her house, despite being friends I had never actually been there. We went inside and she led me straight to her bedroom. Once inside she closed the door and turned to me.

"Get naked and lay on the bed." Her command was stated with mild amusement. So as a normal eighteen year old guy, when a hot girl says 'get naked', I did. She didn't show much reaction as I undressed and finally lay down on her bed. She had stood waiting patiently as I followed her directions and now approached the bed and leaned into kiss me. Once again I was lost in the kiss and felt my cock rise in response to the stimulation. Suddenly she stepped back and I realized that she had restrained my wrists above my head, while I was focused on her kiss.

"Charlotte, what...?" She put a thumb to my lips as she said "shh". Charlotte moved to the foot of the bed where she restrained my ankles as well. She slowly ran her hands up my legs to my thighs and further to my stomach, blatantly ignoring my straining cock.

"I told you this was about me." She laughed softly and when she reached my chest she lowered her head to my right nipple and licked slowly. I was just starting to get used to this sensation when she suddenly sank her teeth into my nipple causing me to yelp, although more in surprise than pain.

"I just want to establish who's in charge." I nodded, although I thought my being tied up would have made that obvious. She straightened up to remove her clothes to reveal her pale naked body, in sharp contrast to her dark hair. I thought she was absolutely gorgeous, my opinion only increased as she stripped. Once naked she climbed onto the bed where she straddled my chest. She settled in and reached down and slowly ran a finger on my lips. Then she ran a finger through her lower lips and returned the finger to my mouth, the taste was sweet, but not overwhelming. I really hadn't known what to expect as this was the first time I had ever tasted a girl's pussy. However it had already proved to be a day for firsts.

"Feel your way out, I'm willing to wait till you get the hang of it." As she said this she shifted so that she could sit on my face. With little idea of what I was doing I stuck out my tongue and pressed it against her lips, her response was a short gasp of breath. Taking this as a good sign I began to tentatively lick around and listening carefully for her reaction. Some places she was fairly silent, others had her swearing and grabbing my head. I wanted to focus on the latter, but I had read that women are not as desperate as guys for orgasm and as such prefer it to build up to a crashing orgasm, rather than just quickly get off. Suddenly I hit a spot that only triggered a soft moan and focused on that spot as I began tasting more of her juices, the taste was stronger directly from the source, but still sweet.

I continued licking even though my neck was aching, my jaw was sore and I was beginning to worry that I might drown as her juices were flooding my mouth and my face was covered. I figured she was getting closer as her breathing was not only faster, but louder as well and in addition her legs were tightening around my head. It was getting increasingly hard to hear with her legs crushing my head so as I wasn't sure what her reaction was, beyond what I could feel from her hands and legs, I began probing and I felt a slight bump and she began shaking violently.

I momentarily thought I had hurt her, but I would hear her moans as she had gripped tighter. Guessing that I had found her clitoris I sucked on it for all I was worth. Soon her whole body tensed and I could no longer breathe. Suddenly the tension ebbed and she released me as she continued shuddering. It was obvious she had cum as the taste had flooded my mouth. The flavor wasn't too different from before, just stronger. She slipped off my face and lay down next to me with her face at roughly my waist and my head at hers. I was in a daze, a mix of oxygen deprivation and shock at what had just happened. Charlotte lay panting as she struggled to get her breath back. Eventually she sat up, looking down at me smiling.

"Wow, not bad. You clearly haven't done that before, but you figured it out." She turned to look at my painfully hard erection and this seemed to delight her as she smiled more. "Well, since you did such a good job I guess it would be really mean to leave you hanging." She laughed before lowering her head to lick up the shaft of my cock with agonizing slowness. I groaned thinking 'this is what she means by not leaving me hanging?' She turned to look at me, laughing when she saw the pained expression on my face.

"Sorry, I couldn't resist. Hold on." She kissed the head and stood to get something from a drawer. When she turned around I saw that she was holding a condom. She quickly unwrapped and rolled it carefully onto my hardon. Charlotte straddled me and raised her hips to slowly lower herself onto my cock. She was tight and very wet as her cunt completely engulfed me.

Soon her ass reached my crotch. She squirmed around momentarily before beginning to move her hips up and down. At first her movements were slow and steady, but she quickly increased speed. Sex in general was new to me, but sex with a condom more so. My cock was squeezed tightly and I wasn't sure how long I could last with her riding me like that. Charlotte continued to ride me as she leaned forward both hands on my chest while she kissed me despite my face being covered in her cum. Suddenly she broke the kiss as she arched her back and I could feel her already tight pussy grip me even harder as I felt the cum rise up the shaft. Charlotte let out a primal scream that was almost a growl as her hands at my chest gripped hard. She gripped so hard that her nails began to dig in to the skin, but I was so far gone as my cum exploded into the condom that I hardly noticed. She writhed on top of me a moment or two longer before her own orgasm ran its course. When she was finished she collapsed on me and I felt my cock soften somewhat inside her. Her head was on my left shoulder, her lips to my ear as she spoke softly.

"Hmm, you may not be huge, but I had fun." She lay on me for a while as I began to feel the dull ache in my wrists and ankles, the increasing sensitivity of my cock and the slight sting in my chest from her nails. However I was feeling on top of the world, I had just lost my virginity and it was amazing. Eventually she stirred and clambered off to lay down next to me. When she saw the marks on my chest she frowned.

"Oh my, I'm sorry I pretty carried away."

"It's fine their not deep, they sting a little, but I enjoyed every minute." She smiled as she sat up to free me and led me to the bathroom and a shower. It was difficult moving after being tied up for what turned out to be an hour. As I was drying myself she returned, her hair was wet indicating that she had showered in the other bathroom and directed me to sit on the toilet while she applied some ointment to my chest.

"You were right they weren't too bad, but just in case I'll use this." The whole time she had not bothered dressing and once she was finished she led me back to her bedroom and I glanced at her and she shook her head.

"No, I'm not looking for another round. I just want to lay down for a bit. Will your parents give you too much grief if I don't bring you back till tomorrow?" I sat on the bed as I thought about this. She pulled me in to lay down next to her as I continued to think.

"I don't know I don't usually go out late. They'd probably be most bothered that I didn't call them and of course ask what I was doing out late. Charlotte what is this? I obviously enjoyed it, I just want to know where we stand." She ran her fingers through my hair and laughed softly.

"This was fun, but if you mean do I want to date, than no. I would like to try it, but we're going off to college soon so I don't think it would work. Although I would love to do this again sometime." I nodded and we soon drifted off to sleep embracing one another. The next morning my parents weren't happy that I didn't call and I don't think they believed me when I said I had crashed with guy friend but I wasn't grounded, I was eighteen. Charlotte and I met up on average once a week, either she would drive me home from school and we would park somewhere or we met up on the weekends, my parents thought we were dating. Charlotte didn't see any reason to tell them otherwise. This was not the last of my sexual adventures, over the years I had more.

To Be Continued

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AnonymousAnonymousover 7 years ago
Great start!

Loved your writing!

AnonymousAnonymousover 7 years ago
Too good not to be better

Having an editor or proofreader work on your story before it arrived here would have corrected such things as "into" when you meant "in to," "their" for "they're," "than" for "then," and more. It would have heightened my enjoyment of your story, too. I hope your next story is better.

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