A Photographer's Fantasy - Sweet Calendar Girls: Gina's Story
by Jon Eugene
Copyright© 2023 by Jon Eugene
Erotica Sex Story: In A Photographer's Fantasy - Sweet Calendar Girls: Calendar, Gina let slip that she seduced the principal of her school. She tells Jon the whole story and how she helped all of the girls at her school.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft Blackmail School Oral Sex Teacher/Student Illustrated .
Well, after the little bomb I let drop after seeing the calendar pictures, I guess I really have no choice but to explain what I meant when I said that the picture reminded me of when I seduced the principal of our high school. I didn’t really seduce him, I guess, but I did fuck him and after I did, things were much better for the girls in that school.
My name is Gina, and Lou (Jonny’s girlfriend) and I are now friends. Although we went to the same high school, we didn’t hang around too much back then, but we knew a little bit about each other. However, when I hired Jon Eugene to photograph my wedding, Lou came along as his assistant and I kind of glommed onto her during the three days of the wedding. We’ve become better acquainted and I think we’re on the way to becoming good friends.
That’s why, when Lou mentioned that Jonny was going to photograph a calendar [see A Photographer’s Fantasy: Sweet Calendar Girls], I asked to be a part of it. I went to the interview, and after Jonny got over the shock of seeing me there, he agreed to let me be a part of the thing. He suggested that I be the September, the Back-to-School girl and he wanted me dressed as a cheerleader. I was a cheerleader in high school and in college, so it wasn’t a stretch for me. Although the cheer costume Lou found for me was very dated, it lent itself very well to a pinup-type of picture. It was when we were doing the more sexual pictures that he put me in his locker room set, nude, with a guy in the background in the mirror, that it all came back to me.
Lou was a couple of years older than me, so she was already out of school when this all happened. I know that Lou (known as Lulu back then) had a bunch of run-ins with the principal and that she almost dropped out of school because of him. I had heard rumors as to his behavior with a number of the girls in school, and some of them did drop out, some to go away for a few months and come back with their mothers having new brothers or sisters. I think you understand: the girls got pregnant, went away, then came back and their mother would take care of the baby, calling it her child.
As I said, I had heard rumors, but didn’t have anything concrete until I was a senior. I was a cheerleader and, as one, I had special privileges. I tried to not take advantage of those privileges, but being able to get out of school to run an errand for “cheer squad” was kind of nice. Some of the girls abused it, but I didn’t. I was also one of the captains of the squad, and I thought of it as being a bit like I was supposed to take care of the younger girls and keep them out of trouble.
Sometimes, though, it was tough keeping the younger girls out of trouble. I’m not sure whose bright idea it was to have freshman girls on the same campus with senior boys, but it’s a situation that is just full of possibilities for sexual mischief. The boys, once they get to high school, seem to be just oozing testosterone and can’t get it really under control until after they leave high school. They’re just walking hard-ons looking for a hot pussy to soak.
So, if it takes about four or five years for boys to get their hormones under control, does it make any sense to figure girls are very much different? About the only difference in the hormone levels is the fact that by the time the girl gets to be a sophomore, say about fifteen- or sixteen-years-old, she can have control, but when she’s fourteen-years-old and a freshman, she’s nearly as out-of-control as any guy! So if guys are just walking hard-ons, girls are often just wet pussies looking for something to fill them up!
I was much luckier than most of the other girls in school. I had been raised in a fairly hedonistic household, going to nude resorts most of my life, so a guy with a boner wasn’t fascinating to me. In fact, there was only one cock I really wanted, and that was of my long-time beau, Cole. We met when we were about eight-years-old and our parents met at the same time, found out they had a lot in common, and so Cole and I were thrust together from then on. I was, and am, enamored of Cole, and he was my first lover after my freshman year. Mom insisted on us waiting and she made sure I had the best protection money could buy. She wanted to be a grandmother, but not by having her really underage child bear the baby. She figured that Cole, despite how mature and responsible he was, might not always have a condom handy (I mean, when you’re nude, where would you put a pocket?!) so when we were together at those resorts, we were discreetly chaperoned.
So, by the time I was a senior, I knew which end of cock was the dangerous end and I wasn’t looking for anyone new. However, I had heard the rumors about the principal. He often came to watch us practice, and he was always there for the home games to watch us prance about. He even often came to away games, but he seemed to sit further away from the front lines, then. I watched him and figured out that he really did have a letch for the younger girls. He had never hit on me, but I think that was because Daddy was such a big booster who always had some money for this or another cause in the school, so I think I may have been off-limits.
I watched him as he watched us, and during my senior year, I noticed that he seemed to have eyes only for the youngest of our squad members. She was very young, only barely fourteen, and she looked even younger. She had a fairly flat chest, was narrow in the hips and had long legs. She was barely ripe, still just developing. She was pretty shy, which was very unusual for a cheerleader, but she gave it her all. She rarely spoke, was very diffident, but enthusiastically did whatever we older girls told her to do, and, as I said, she gave it her all when cheering. It was like she was almost a robot until the lights came up on the sidelines and she could be on stage performing. The two-in-one personality was really quite interesting.
However, the Principal, Mr. Demming, just watched every move that Samantha, the youngest cheerleader, made. He was almost salivating over her as he sat there. I did my best to make sure that she was placed as far away as possible from his lecherous stares, but I couldn’t control every move she made. She was small, too, kind of like me, and very light weight, and she was the second flyer. That means that she was the top of the pyramids or was the girl that got tossed up as high as the bigger girls could throw her during special routines.
And, Mr. Demming watched her every move, his tongue practically on the floor when her skirt flew up and her bloomers were exposed. Lecherous old man!
One day, I heard her name announced on the intercom. She was being called into the office. When class was over, I headed over to the office and ran into Samantha just as she was coming out. She was in tears! I grabbed her hand, told the secretary that Samantha and I had “cheer business” to discuss, and pulled the sobbing girl into a washroom to find out what was going on.
“I can’t tell you,” Samantha sobbed. “I’ll get into more trouble if I tell anyone. What am I going to do?”
I pulled her into a stall and wrapped my arms around the quivering child. “You’re going to tell your cheer captain just what happened. I’ll take the consequences, not you.”
She still sobbed that she couldn’t tell anybody, but eventually I got her calmed down enough that I could make out what happened through her sobs.
It seemed that she was kissing a boy under the gym bleachers earlier in the day. The boy had his hands up under her blouse when a teacher had caught them and told them that they weren’t supposed to be there, even though classes hadn’t even started for the day. The teacher had taken their names and told them to get out of the gym and head for their homeroom class.
Later, the cheer coach told me that the teacher had a good laugh about it in the teachers’ lounge a little while later, describing the frightened faces on the kids when she caught them. The other teachers were laughing with her and telling stories of the kids they had caught in compromising positions when Mr. Demming, the principal, came in. He demanded to know what was so funny, and the teacher told him, complete with names. The next thing anyone knew, Samantha was being summoned into the office.
Samantha almost lost it as she was telling me what happened in Mr. Demming’s office. “He made me feel so dirty,” she said. “He said that school wasn’t the proper place for that kind of behavior, that school was for learning.”
She took a deep breath and whispered, “That’s when he told me.” She broke out in sobs again and I had to wrap her up, telling her that everything would be all right, over and over again.
She broke away from me. “No!” she almost shouted, then her voice dropped to a whisper again. “No, it won’t be all right! He said that I had to stay after cheer practice, that I had to be the last one to leave and that he’d deal with me after school, after practice.” She dropped into my arms again. “What am I going to do? I think he wants to ... to... fuck me!”
She started sobbing and wailing again. What could I do? I’d had other girls break down because of boyfriends breaking up with them. I’d comforted a girl when she found out her mother had cancer. I’d even tried to help the cheer coach when she wanted to quit, but I didn’t have any real experience with a guy who preyed on young girls like this.
I held her and when she finally got herself under control again, I told her I would think of something and that she needed to concentrate on getting through the rest of the day. I took a wad of toilet paper from the roll and handed it to her.
“Wipe your eyes,” I said. “Put some cold water on your face, too. You look like you’ve been crying and if we don’t get that off your face, someone will start asking questions, and we don’t want you breaking down again, do we?” She shook her head, then did what I told her to do.
Once she had dried her face, I had her stand in front of me. I reached into my purse and pulled out a little compact and did what I could to repair her face. When I was done, I turned her to the door and gave her a gentle swat on her skirt-covered butt and told her to get to class. “I’ll figure a way out of this for you.”
Kissing a guy under the bleachers? That’s normal. Yes, it was a breach of school etiquette, but it wasn’t something to get the principal involved. Maybe if they’d actually been fucking ... but they weren’t, so having to go to the principal was a bit over the top, in my opinion. Of course, by then I was aware of Mr. Demming’s penchant for young girls, so it really didn’t surprise me.
What really pissed me off was the fact that Tommy Jones, the boy who had been trying to feel Samantha’s tits, hadn’t been embarrassed by being called to the office. Well, not yet, anyway. He was a senior and a star ballplayer, so he probably wouldn’t catch any flak. It’s part of what I was saying earlier: senior boys and freshman girls are just not a good mix; there’s just too much of an experience gap, and if the boy in question is an athlete, well ... too bad for the girl, is all I’ll say.
I was furious! What was Mr. Demming thinking? Did he really think he could get away with punishing a freshman girl, a girl barely fourteen-years-old? And, what did he think her punishment should be? And, why wasn’t Tommy on the carpet, too? Of course, that last question was too easy to figure out and that made me angry, too!
I heard the bell ring and I did a little schedule calculation: it was 3rd period when Samantha was called into the office, so that bell sounded the end of 4th period, so this was my study hall time and I had a lunch after that. I had some time to do some planning.
I went to the study hall teacher and got permission to go to the library for some research. My brain was furiously bouncing back and forth about what we could do, but I wasn’t getting much satisfaction because I wasn’t coming up with a good plan. I plopped down in front of a computer and had the inspiration to do a little research on my problem.
Basically, I wanted to know just how much trouble Samantha would be in if this all came to light. Well, that was interesting: according to the computer, she, being a minor, wouldn’t get into trouble at all, except maybe with her parents, but legally no problem. However, with Mr. Demming being the principal and being so much older than her, he could have some real problems, both socially, legally, and with his current and future employment, not to mention what his wife might have to say about it all.
And that finally got me on the right track on how to get him off Samantha’s back. I still had about an hour before my next class, so I went to the coach for a pass to go off-campus. I did a little shopping and was back in school just as lunch was over.
When school was out, we cheerleaders went to the locker room to change. It was too crowded there to talk, but as we were heading to the auxiliary gym, Samantha was lagging behind and that was fine because I was able to talk with her as we walked to the gym. I had a plan, but I needed her to help me with it, if she was willing to participate. She was a bit reluctant, but I helped her see this as her ticket to freedom from her persecutor.
The plan was simple: she’d wait, just as she had been instructed. I would be one of the first girls out of the gym, and as the others were leaving, Samantha would open the door of the locker room that led to the football field and I would slip back in. I would strip and wait for Mr. Demming in her place while Samantha hid in one of the lockers. Easy, peasey as they say. We’d catch him in flagrante delicto (a phrase I learned that day!) and maybe we could use that to get him off Samantha’s back.
Samantha, however, was a wreck. She couldn’t seem to do anything right and eventually, she fell. We couldn’t really tell how bad it was, so the coach took her to the convenient-care clinic. That kind of put the kibosh on that plan, but I had a backup plan in case Mr. Demming showed up. I stripped and set up the room, hurrying. I didn’t know if Mr. Demming would show up, and I had to have everything ready for when he did.
And, he did show up. About five minutes after all the other girls had left, I heard the door to the locker room open and close and the footsteps of a heavier person wearing hard-soled shoes come into the room. I stepped under a running shower head and waited. I didn’t have to wait too long.
“Samantha?” a deep voice queried. It was Mr. Demming.
I popped my head out of the shower room, hiding myself behind the wall so that he couldn’t see my body. “Samantha got hurt and had to go to the clinic,” I replied. “What are you doing here, Mr. Demming?”
“Uh, I, uh ... was supposed to meet her here and then take her home,” he said, lamely.
“You’re not supposed to be in the girls’ locker room,” I said, making it an accusation.
“I ... uh, Samantha got into some trouble today,” he said. “I was going to take her home to talk to her parents and see if we couldn’t come to a solution to the problem.”
“I see,” I said and I stepped out of the shower, nude as the day I was born. “Samantha told me about the ‘problem.’ Don’t you think you should also be talking to Tommy Jones’ parents, too?” I was getting worked up. I sauntered over to him and poked him with a finger. I wanted to keep him off-balance.
“Yeah, Mr. Demming,” I continued. “Samantha told me about what happened in your office this morning. She’s a little young, isn’t she? She’s still a virgin. Why don’t you just fuck me instead and we’ll just put this whole thing behind us, OK?” I was dripping water onto the floor and I leaned in so that I dripped some onto his clothes.
I reached between us and clutched his cock through his slacks. It was hard, but it was small, not nearly what Cole packed. “Yeah, I can see that fucking a cheerleader turns you on.” I reached up and pulled his clip-on tie off. “Let’s get you out of these clothes so that you can show me what you wanted to show Samantha.”
He wasted no time taking off his coat and I swear that some of the buttons on his shirt went flying in his haste to remove his shirt. I encouraged him all the way, saying how strong and macho he was, that he’d have me eating out of his hand in no time. I was working his belt off and the fly of his pants was no match for my determination. He toed his loafers off and dropped his pants and they went flying after his jacket. He stood there in his stocking feet, his tighty-whitey’s tenting slightly with his engorged cock. Even blood-filled it barely filled my hand.
I hooked my thumbs into the waistband of his underwear and pulled them down. “Let’s just see what we’ve got here,” I said and when it popped into view, I said, “OOO! Pretty! And look at those balls; so heavy and filled with spunk!” I cupped them as I spoke. I could hear his intake of breath and felt his chest expand at the compliments. Believe me, the whole package was not something that impressed me at all!
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