Caught by the High School Principal again

A Fan Fiction story based on the characters from the “Caught by the High School Principal” ( story.

Something I never told my best friend Tom was that Tricia and I had sex in front of Principal Collins again. It happened on a day that Tom was not in school. Tricia and I were hanging out in front of the storeroom that Principal Collins had caught Tom, Tricia, and I in on the day that he made us have sex in front of him. Principal Collins was walking by. “What is it with you k**s and that storeroom? Come to my office. I want to talk with you two.” Tricia and I follow him to his office. He locks the door after us. “Were the two of you about to go into the storeroom and have sex?” he asks sternly. Tricia and I look at each other sheepishly and mumble “maybe”. “Have you had sex since you were in my office?” We tell him that Tom and the two of us had several three ways since then. “I see. Since the two of you were about to about to have sex and you like having another person around you might as well do it here in front of me so I can watch.” Tricia and I look at each other and shrug our shoulders. We start to undress. After Tricia has her top off I start to suck on her tiny titties. Her hand moves down and rubs my cock through my pants. As I continue to suck on her tiny titties Tricia's hand moves under my waist band and into my pants. She rubs her hand against my cock. I loosen my pants and they fall to the ground. Tricia kneels down and pulls down my shorts. Using just her head she puts my cock into her mouth and starts to suck it. “Good technique Tricia” Principal Collins says. My cock is soon hard and throbbing. I pull it out of Tricia's mouth. Tricia gets down on her back. I kneel down and pull her bottom off. I lie between her legs and start to lick her pussy. After a few minutes Tricia is moaning “Fuck me.” “Go ahead and fuck her Brad” Principal Collins tells me. I get into a kneeling position and help Tricia get onto her hands and knees close to me. I bring my cock up. It is dripping with pre-cum. I put the head on Tricia's pussy and push it in. I pull it out and push the head in again. This time I continue pushing inward until I am balls deep. I begin thrusting. I vary my thrusting depth. Sometimes it is long and deep. Sometimes it is short and shallow. “Brad, I see that your doggy technique has improved. You were fumbling the first time I watched you.” Principal Collins had already taken his cock out of his pants and was stroking it. He walks around us looking for different views of the action. After about 5 minutes Principal Collins tells us to change positions. Tricia rolls on to her back and I move on top of her. Her legs are pressed toward her head. I use my hand to guide my cock to her pussy. I begin thrusting. After I get into a thrusting rhythm I lean forward and start to kiss Tricia. “Nice, Nice” Principal Collins says. At times he holds her legs back. We continue in this position until I feel the build up to an orgasm. I blurted out “I am about to cum”. Principal Collins replies “Don't pull out Brad. Shoot your cum deep in Tricia pussy”. After just a few more thrusts I let out a load moan and start to cum. My cum spurts out of my hard cock and deep into Tricia. I continue to thrust because it feels so good for my cum to shoot out as I thrust. After I stop cumming I stop thrusting. My cock is balls deep in Tricia's pussy and I am getting sweaty.

“How did it feel to cum in her pussy Brad?” Principal Collins asks. “It felt good and it felt natural.” I replied. “Good. Now roll off of Tricia.” he tells me. After I do as commanded Principal Collins kneels down next to Tricia. He moves his hand the hand he was stroking his cock with between her legs. Then he places his index and middle finger into her pussy. He presses his fingers in deep enough that his ring finger presses hard against the outside of Tricia's pussy. I can see that he is moving his fingers slightly. Principal Collins slowly pulls his fingers out of Tricia's pussy. They are cupped. There is a large amount of my cum on the palm side of his fingers. Principal Collins brings his hand up to his head and places his cum covered fingers into his mouth. He sucks my cum off his fingers. “What a perv” I think. Principal Collins pulls his hand away from his mouth and back down to Tricia's pussy. He begins slowly thrusting his fingers in and out of her pussy. He quickly picks up the pace. I can hear the sound of sloshing. Tricia arches her back and practically screams “oh yea, oh yea” over and over again until she finally stops. Principal Collins removes his fingers and hand from Tricia's pussy. “Brad, just like boys, girls can have orgasms.” he tells me. “Now lick out Tricia's pussy” he commands me. “But it has my cum in it” I protest. “A boy needs to learn to lick a creamy pussy” he tells me. I get between Tricia's legs and bring my face down to her pussy. I hesitate to go further. “Do it Brad” Tricia tells me. I start licking Tricia's pussy. I can taste my cum. I want to throw up. But to keep Principal Collins happy I stifle my urge and continue to lick her pussy. After a while it does not bother me anymore. Several minutes pass. “OK Brad. I want you to lick Tricia's asshole.” Since I cannot reach her ass while Tricia is on her back she rolls over and gets on her hands and knees. I start licking her hole. It is not as bad as I thought it would be. “Well, enough of that. Brad, get onto your back. Tricia get between his legs and start sucking on Brad's cock” Principal Collins commands us. We get into our positions. My cock has remained hard since I watched Principal Collins jack Tricia off. Tricia takes my hard cock into her mouth and starts to suck it. Her head moves up and down. I put my arms down and lift my upper body up so I can watch. “Tricia, can you taste Brad's cum on his cock?” Tricia mumbles something. Several minutes pass. “Brad, have you fucked Tricia or any girl in the ass since the last time you were in my office?” Principal Collins asks. “No Sir” I reply. “Good. I get to watch your first time.” he says. “Tricia, have you had a cock in your ass since the last time I saw you?” “Only Tom's when he and Brad fucked me again.” she replied. Truth be told the three of us had sex together several times since that day in the principal’s office. We DP'ed each time but only Tom got to fuck Tricia in the ass. He cummed in her once.

“Tricia, get back on your hands and knees. Bard, kneel between her legs behind her.” Principal Collins commands us. After we get into position Principal Collins moves around and places his hands on Tricia's buttocks. He separates her cheeks and spits onto her asshole. “Ok Brad, place the head of your cock on her asshole.” I do. “Now slowly press your cock into her asshole. I want to watch as your cock enters her ass for the first time.” I start pressing my cock into Tricia's asshole. She winces from the pain but I continue. I can feel the tip of my cock's head start to enter her hole. I look down but Principal Collins head is the way. I press my cock further in. It feels like half the head is in now. Principal Collins spits onto my cock head. I press my cock still further in. The head is fully in Tricia's asshole. Principal Collins looks up and tells me “What a wonderful sight. The first time a young man's cock enters an asshole.” He moves his head away and I look down. “Spit on your cock if you need more lubrication.” he tells me. I slowly slide my cock all the way into Tricia's ass. I feel my balls touch the bottom of her pussy. “Brad, stay like that. I want to check that you are all the way in.” Principal Collins tells me. First he presses down on Tricia's cheeks to get a better view. Next he moves behind me, leans over, puts his hand between my legs, and lifts my balls. “Push your cock in just a little more Brad.” I push in more. My groin is pushed firmly against Tricia’s cheeks. “Good boy. You are all the way in. Now stay that way”. Principal Collins gets up and moves to the side. “Stay still you two. I want to burn this image into my mind. A young man with his cock in a young woman's ass for the first time. Too bad I don't have a camera.” After a minute or so of watching us stay still Principal Collins says “Brad, pull your cock all the way out”. My cock comes out with a pop. Principal Collins reaches in between Tricia and I and puts a finger in her ass hole. He moves it around in a circle a few times before spitting in the gaping hole. “OK Brad, slide your cock back into her ass.” I use my hand to guide my cock to her hole and press inward. It slides in slightly easier than before. I go balls deep again. “Go on. Fuck that ass hole.” Principal Collins commands. I begin a slow thrust. After a few thrusts I spit on my cock as it moves into Tricia's ass hole. As Tricia's hole relaxes it is easier for me to thrust. I pick up speed. After several minutes I bring one leg up. I soon bring the other leg up. I am now crouching behind Tricia as I thrust my cock in her ass. I grab Tricia's sides to keep myself upright as I thrust. After several minutes Principal Collins says “Brad, go balls deep and stop thrusting.” Which I do. “Now I want the two of you to lay on your right side without Brad's cock coming out of Tricia's ass.” Tricia and I slowly lean to the right and immediately fall over. My cock did stay in Tricia's ass. “Brad, start thrusting again” he tells me. After a minute of watching us Principal Collins leans over, grabs Tricia's left leg and props it up. He then presses my left hip to move it slightly. He now as a clear view of my cock as I thrust it back and forth in Tricia's ass. We stay in this position for several minutes. “Brad, roll on to your back and keep your cock in Tricia's ass.” Tricia and I move as one. Tricia is facing away from me. “Tricia lean back as far as you can.” Principal Collins commands. Tricia leans back enough that she can use her out reached arms to support herself. I thrust my cock up into Tricia's ass. After a minute Principal Collins kneels near us. He reaches down to Tricia's pussy and begins fingering it. It does not take long before Tricia is moaning with pleasure. Her moaning becomes louder. Suddenly her ass tightens and relaxes, tightens and relaxes. She practically screams “Yes, Oh Yes” repeatedly. The way her body was acting was hot. I felt the onrush of an orgasm start. I loudly moan “I'm cumming”. Both Tricia and my bodies are bucking in pleasure. After the wave of pleasure has passed from the two of us we lay still. My cock still up Tricia's ass. The two of us are out of breath. Principal Collins removes his hand from between Tricia's legs. “That was hot. The two of you had orgasms at the same time.” he says to us.

Alternate 1:

Principal Collins tells us to get dressed and if he catches us again he will have us have rough sex in front of him.

Alternate 2:
Principal Collins tells me to get dressed and leave. He wants to talk to Tricia in private. As I leave the office I see Principal Collins start to loosen his tie. At that moment I guess he plans on fucking Tricia in private. I hang around and wait for Tricia. After an hour she comes out of Principal Collins' office. I ask her what happened. She tells me that Principal Collins had her suck on his cock and balls, and then he rough fucked her in the ass before rough fucking her in the pussy. After he cummed in her pussy he put his entire hand in her pussy and moved it around. It hurt. He said the pain she was feeling was nothing like the pain she would feel if she got pregnant and gave birth. He fucked her in the ass again until he pulled out and shot his cum over her face. He wiped his cum off her face with a finger and made her eat it.

Alternate 3:

“What the hell. I probably will not get another chance.” Principal Collins exclaims. “Tricia, get on your hands and knees” he tells her. Tricia rolls off of me. My cum dripping from her ass. Principal Collins slips off his shoes and pulls off his pants and underwear. His cock is hard. After Tricia gets on her hands and knees Principal Collins moves behind her and squats down. “Tricia, my cock is larger than Brad's so this might hurt a bit.” He was right. His cock was longer by a few inches and fatter as well. Principal Collins places his cock up against Tricia's asshole and begins to slide it in. Tricia winces and moans. Collins continues to slide his cock into Tricia's ass. Again I think what a perv Principal Collins is. A 40 year old man fucking a teenage girl in the ass.” Yet I can't look away. Principal Collins pushes his cock balls deep into Tricia's ass. He leans forward and takes Tricia's chin in his hand and turns it toward him. “How does it feel having an older man's large cock in your ass Tricia?” he asks. “It is bigger than Brad's and Tom's cocks sir. But it feels OK” she replies. “Brad, come here and hold her butt cheeks apart.” I move closer and take each cheek in a hand and pull them a part. Principal Collins' pubic hair is pressing tight against her. He slowly begins pulling his cock out. It is glistening with my cum. “This is what a cock looks like when it is doing sloppy seconds. He pulls his cock fully out of Tricia's ass. He reaches down and aims it for her ass before sliding it back in. He licks the fingers that had touched his cock. Tricia shivers from the discomfort of his cock sliding in. He pulls his cock fully out again. He pushes inward but his cock misses her hole and moves up her crack instead. I get a close view of the tip of his cock. He pulls back a little, angles his hips and pushes forward. His cock enters Tricia's ass. He slides it all the way in. He begins pulling his cock out but stops just as the base of the head becomes visible. He slides his cock back in. Again he pulls his cock out until the base of the head becomes visible then he slides it back in. He continues to thrust like this. I soon forget how pervy I thought Principal Collins was. It was hot seeing him thrust his cock in Tricia's ass. My cock gets hard again. Principal Collins notices my hard on. “Looks like you like watching me fuck Tricia in the ass. Good you can join in. Lie down in front of Tricia and let her suck your cock while you watch. It will enhance your pleasure and mine.” I get down on my back with my legs on either side of Tricia. My crotch is under her face. I prop my torso up using my elbows. As he thrusts Principal Collins loosens he tie and tosses it onto his pants. He then unbuttons his shirt. Without missing a thrust he takes his shirt off and tosses it into the pile. He has hair on his chest above his nipples with a band of hair running between his pecks down to his belly button. From there the hair spreads out and merges with his pubic hair. His abs looks like he goes to the gym on a regular basis. Now that I see his full body I get even more into the experience. I realize I am having a threeway with an older man and teenage girl and I am loving it. After several minutes Principal Collins tells me to swing around so my face is under Tricia's groin and my groin is under Tricia's face. He tells us this position is known as 69. Tricia continues to suck on my cock and I begin licking her pussy. I get a clear view of the underside of Principal Collins’ cock as it moves in and out of Tricia's ass. His balls swinging during each thrust. Once his cock comes all the way out of her ass. I am glad that it sprung up instead of down.

After several minutes Principal Collins pulls his cock out of Tricia's ass and moves away slightly. “Brad, twist around so you are face to face with Tricia and your cock is near her pussy.” I swing around. “Now Tricia, lower your hips slightly and put Brad's cock in your pussy. Brad, go ahead and thrust away.” As I thrust under Tricia Principal Collins moves closer. I stop thrusting for a moment as he slides his cock back into Tricia's ass. Like when Tom fucks her in the ass I can feel Principal Collins' cock through the thin walls separating Tricia's pussy and ass as he pushes his cock deeper into her ass. Both Principal Collins and I start thrusting. I think what a sight this must be: a teenage boy and a 40 year old man double penetrating a teenage girl. I should be grossed out but it feels so good and not pervy. The three of us fuck in this position for 5 or so minutes.

Principal Collins leans over and asks “Tricia, have you had two cocks in your pussy at the same time?” “No sir.” “Good. Brad, stop thrusting.” Principal Collins pulls his cock out of Tricia's ass and starts to slide it over mine. Tricia's pussy tightens up when the head of his cock starts to enter her pussy. Tricia whimpers a little. “Take it. Take it.” he says as he pushes his cock further over my cock and deeper into her pussy. It dawns on me that his cock is touching mine. I think for a moment how pervy it is. But it does feel good. After he is fully in Principal Collins leans over slightly and asks me “How does it feel, Brad, having my cock tight up against yours?” “It is a bit pervy” I reply. A pervy smile comes to his face. He begins to slowly thrust. His cock rubbing against mine. It feels good. I start to thrust. It feels great. My cock rubbing against Tricia's pussy and Principal Collins' cock and his cock rubbing against mine. After several minutes I couldn't help it I started to cum. I let out a moan. My cum made it easier for our two cocks to move in Tricia's pussy. Principal Collins leans over, smiles, and says “Good boy Brad. I was hoping that would happen.” After I stop thrusting and pull out Principal Collins picks Tricia up off the floor and sits her down on the edge of his desk. He stands between her legs, puts his cock into her ass, and begins thrusting. I come over and hold her legs back. I get a good view of the action. Every so often he would pull his cock out, rubs it sideways over Tricia's pussy before sliding it back into her ass. Principal Collins' thrusting becomes faster. He pulls his cock out and begins rubbing it across Tricia's pussy. He begins to moan. Three big shots of cum shoot out of his cock and onto her pussy lips. He begins to slide his cock back into her ass as another shot of cum shoots out. He moans as he thrusts his cock into her ass and begins thrusting. Eventually the moaning stops and Principal Collins pulls his cock out of Tricia's ass. His cock is not as thick as it was. But it was shinny with cum.

“Brad, get down between Tricia's legs and lick her pussy clean.” I begin to protest because it is his cum that is on her pussy. “Brad, when a man does a threeway he can't be afraid of another man's cum.” Principal Collins holds Tricia's legs up. I get down between Tricia's legs and begin to lick his cum from her pussy. It was not as bad as I thought it would be. Having licked my cum from her pussy earlier helped me. When I think I have licked all of the principal's cum from Tricia's pussy I pull away. “Let me check” Principal Collins says. He moves between Tricia's legs and starts to lick her pussy. First he licks the outside then he pushes his tongue deep into her pussy. After he is satisfied he lowers himself and licks Tricia's ass hole. His tongue thrusts inside a few times. Principal Collins stands up, picks Tricia off his desk, and lowers her to the floor. “Now suck the cum off our cocks” he tells her. He grabs me and pulls me to his side. His arm is around my shoulders. Our naked male bodies touching. Tricia kneels in front of us and sucks on each of our cocks which are still hard. After a minute Principal Collins is satisfied our cocks are clean.

After the three of us get dressed Principal Collins says “Ok, you two listen up. This never happened. Don't tell anyone. Including Tom. Agreed?” Tricia and I look at each other, nod, and say “Yes sir. No one including Tom will know.” I particularly did not want anyone to know that I had a good time fucking Tricia with Principal Collins. That would make me look like a perv.

This was not the last time I had a threeway while in high school. Tom and I fucked Tricia once more before moving on to other girls. Tom and I had numerous threeways together over the next 3 years that we were in high school. I had a few threeways without Tom. Some I never told him about. Those stories are for another day.