Characters: Principal Voyeur, Amy
Hello. My name is Amy. I am a senior at Clairmont Catholic School for girls and I have recently been accepted to Harvard University. To the rest of the world, I have everything I need. I am Class valedictorian, Varsity cheerleader, and class president. I recently celebrated my 18th birthday and had one of the biggest parties of the year. On the inside, I am frustrated from years of repression and overworking. I long to lose my cherry, but I want it to be with someone worthwhile. Most of the boys my age are way too immature, and wouldn’t know what to do with me. What I need is an older man to show me the ropes. There are so many cute teachers at my school. I wish they would give me some “extra credit.” I have such an obsession with older men; I have actually developed a crush on the principal of our school, and would give anything to have him inside me. The thought of the forbidden coupling gets me very hot. Maybe I will wait until the day I graduate and then jump him. I wish something could speed up me losing my cherry. Oh well. You can’t have it all.
Amy in class:
Lately I have been so horny I am having trouble focusing on my schoolwork. The fact that I drip like a faucet doesn’t help my studying. I stare at equations and all I can think about is losing my virginity and having that first hard dick inside me. I have even turned to drugs lately in order to alleviate my stress. How ironic! Valedictorian catholic school girl on the outside, desperate virgin druggie on the inside. Maybe I should talk to someone.
A voice comes over the loudspeaker. “Could Amy Brown please come to the principal’s office immediately?” Amy looks visibly nervous, and shakes a little as she gets up and proceeds out of the classroom.
Scene in principal’s office:
Amy enters the room and says hello to Principal Voyeur. I ask her to please sit down, that we have something very important to talk about. I have noticed that she frequently looks either hung over or on drugs, and I have searched her locker without the knowledge of the rest of my staff. I have found her to be in possession of prohibited substances, and I tell her that this is a serious offense that could possibly result in expulsion.
Amy breaks into tears, and tells me between her tears that she has been very stressed out lately studying for her exams and that she is trying to stay sane. I feel more sympathy for her than anything since I know how hard she worked in order to get this far. I walk around my desk and kneel down next to her. She looks up at me, and then her eyes look into mine and convey a sense of attraction. She stops crying for a minute, and wipes away her tears. “I have an idea. I think you are very handsome, and I have wanted you for a long time. You can do whatever you want with me, and I won’t try to stop you. After that, if you can look the other way, I would appreciate it.”
“We can’t. We are in a public place.”
“Shhh!” Amy places a finger to her lips. “It’s the last period of the day, and you can lock your door and tell your receptionist to not let anyone in until you are ready to leave.”
“I’m not prepared.”
“Don’t worry about it! My parents have had me on the pill for two years. They think that everyone my age is fucking. I want you so badly, principal voyeur. Make me into a woman. Make love to me!”
I pull her bra off and start sucking on her gorgeous DD tits, and she moans at the sensation. I expertly lick and bite her nipples before briefly sucking them into my mouth. I can tell she is enjoying it from all the noise she is making. I continue this for a few minutes, until she pulls my dick out through my suit and starts sucking it with vigor. She continues this for a few minutes and then pulls her skirt up to her stomach and moves her underwear to the side so that I can access her Vagina. She backs up and sits right on my principal’s desk. She slowly spreads her legs and gives me this “fuck me” look. I lie her down on the desk and continue to place my pulsating member at her inner labia. I make sure to rub my penis on her clit for a little while rutting my shaft between her lips. I want her to be so hot that she’s begging for it! As I rut between her lips, I use both hands on her lovely breasts and do some more work on them to increase her arousal. I can feel her wetness grow with my rutting and I know she is almost ready. Suddenly, she leans up and grabs me by the shirt. Looking me in the eye, she says “please don’t tease me anymore. Put your lovely cock in me!” I put my penis at her entrance, and slowly push forward. She is unbelievably tight! Thank god she is sopping wet. After slowly going in a few inches, I reach an obstacle. Amy is a virgin! I look her in the eyes, as if asking for permission.
“You don’t need to stop, I’ve wanted you for years and I can’t think of anyone else I’d rather have as my first. Just be gentle.” She smiles a smile that tells me how smitten she is, and wraps her legs around my waist. I put my hands on her waist and slowly push forward. I feel the head of my penis stretch around her barrier, and then slowly give way. Amy grimaces but doesn’t make any sounds of pain. I keep going until I can feel my balls on her ass. Once I reach full penetration, I realize how close I am to her cervix. We seem to be a great fit in that department. Once I obtain full penetration, I give Amy a minute to adjust to the new sensation.
After a brief period of time, I withdraw and go back to thrusting. After the first few thrusts, she stops grimacing and enjoys. A wide grin crosses her face as she surpasses the pain she felt from having her hymen break and revels in the exquisite pleasure radiating out from her pussy. She bites her lip to keep from screaming since she knows that the principal’s secretary is right outside. “How does your thick cock feel in my tight pussy? I’m so glad you are my first.
After I do all the work for the second position, I give Amy a chance to ride me and prove herself. She tells me that all that time doing exercises for cheerleading has given her strong hip muscles. She faces me and slowly lowers herself on to my cock, and then gets a steady rhythm going. I can see her pussy muscles gripping my cock every time she moves up; her vagina is gripping my shaft so tightly.
As I bounce up and down on his cock, the sensations are exquisite. I can feel every vein and ridge as his length penetrates my body. Suddenly, I have a wicked thought. The taboo nature of the situation is a huge turn on for me. I never would have guessed that I would lose my virginity in the principal’s office of my high school. I want to explore my newfound sexuality, and I decide that since I have already given principal voyeur my oral and vaginal virginities, I might as well let him have all my holes and give him my anal virginity as well. At this point I love sex so much that I know I have to try it. It might as well be with him. I tell him that I want him to have all my virginities, and that he should feel very special for being offered this. I wanted Principal Voyeur for years before he took my virginity, and now I want him even more. I stop bouncing for a minute with his penis still fully inside me and lean forward to give him a long, intimate kiss. Once that is over, I wrap my arms around him and bury my head in his chest. We stay that way for several minutes, basking in the intimacy we have just created. Once I am ready to resume, I lift myself off his penis and aim it at my back passage. Principal Voyeur helps me to line him up with my anus, and I ever so slowly descend on him. At this point he uses both of his hands to hold up my rear and help me to slowly descend on his cock. I don’t enjoy the sensation as much as I enjoy vaginal sex, but it is still fun. As I slowly descend, I do my best to maintain eye contact with my new lover. Once he is fully embedded inside of me, we take a break and go back to our deep kissing. After a few minutes, Principal Voyeur puts his hands under my ass again and I start to move up. It is very slow going and I feel as if my anus is gripping him like a vice. I can tell from the look on his face that he is enjoying it as well. The Principal and I are joined in ecstasy for a few more minutes before we realize that the period will soon end. At that point I start to bounce up and down on his cock as fast as I can. This could help loosen me up for the next time we meet. (hehe) As I quickly bounce up and down on the Principal’s dick, I can see his breathing quicken and I can tell he is getting close. “Amy, I’m going to cum!”
“I can tell,” I respond. “Cum inside me! I want to feel it inside me for the rest of the day!” With that, I feel the Principal’s penis swell up to an even bigger size and ejaculate its first load of semen. I immediately slam myself down on his lap so I can get his semen as deep inside me as possible. I certainly don’t want any dribbling out! Once his hips are flat on my lap, I immediately wrap my arms around him and seek out his lips. As he pumps load after load inside me, I make sure to invade his mouth with my tongue. I sit there for a few minutes while his semen coats my insides. I have never taken a load before, but to me this seems like a big one. I later confirmed with Principal Voyeur that he had not had sex since his wife left him, so I had just taken 6 months worth of semen! When his penis finally stops pulsating inside me, I am so happy I am beaming, and I now care for Principal Voyeur more than ever. I decide that even if nothing else ever happens between us, that was a wonderful experience.
I haven’t had sex that good in years. My wife left me about six months ago, and ever since that I have been too miserable to worry about dating. At the end of my marriage, my wife was frigid and our sex was forced. Banging this little nymph showed me the other side of the coin! After we had finished and gotten dressed, Amy told me that she hoped this could stay our little secret. She tells me “I owe you for giving me a great first experience,” and I joked with her that I hope she can pay me back soon. I tell her that since I had so much control over my schedule I could arrange for her to visit me with regularity, and she tells me that might not be enough. She gives me a seductive smile and tells me that we’ll figure something out.
I beam and tell her “I can’t wait” as she leaves my office.