After college, there was little for me to do but get a job. I had majored in English, so becoming a teacher was my best option. I latched on with a private Catholic school in upstate New York, a ritzy place that costs untold amounts of money to send your kids there, though the teachers’ compensation leaves much to be desired. I am 31 years old and have been teaching there for 8 years. The weather is beautiful and while I may not be rich, I have settled into the lifestyle comfortably.
It was autumn and the leaves were vibrant shades of fall when I first delved into debauchery at St. Mark’s Academy. The first term was just ending and I had assigned a paper on The Great Gatsby, a common assignment among upper level high school students. Because of the nature of the school, all the students were doing fairly well in the class (with a few exceptions), but some were more interested in their grades than others. One of the girls was Hillary Jacobs, a slender brunette senior who was looking to go Ivy League after her time at St. Mark’s. It appeared like she would get in somewhere.
Hillary was more than just a smart girl, she was the darling of the rather small senior class. We graduated about 100 students a year and Hillary was the most visible of them all. She was the high school stereotype, a perky cheerleader with a great body. I had at times taken notice of it and been impressed, though I would never act on it. She was even grooming her sister Gwen as the next queen of the academy. Gwen was 16 and was curvier than Hillary, certainly rivaling Hillary’s natural beauty with breasts and hips that suggested a girl more experienced.
I was sitting in my office taking care of some work when Hillary knocked on the door. She came in wearing the school uniform, which consisted of a white shirt, a green plaid skirt over white socks, and black shoes. The girls had a choice to wear ankle socks or knee socks and Hillary always elected knee socks, surely because she knew they accented her long legs. Her dark hair was pulled back in a ponytail, which reached halfway down her back. She wore light eyeliner around her pale blue eyes.
“Mr. Bloom, do you have a minute?” she asked sweetly.
“Sure, Hillary. Come on in.”
She walked over to the chair in front of my desk, matted her skirt to her side and sat down. She crossed her legs quickly.
“I don’t know where to go on this paper.”
“Well, what do you have so far?” I asked.
She showed me what she had, which wasn’t that bad. Her paper was about the different characters representing the upper class of America in different eras, a topic that I found interesting and told her so.
“Well, I think that the topic is ok, I guess,” she replied. “But there is one passage that I just can’t get.”
She got up out of her chair and walked around my desk and stood beside me. The paper lay on the desk and she rifled through the pages to find the passage she was looking for.
“Let me read it again to remember it,” she said. To do this, she bent over the desk. As she leaned over, her skirt (which was about 3 inches above the knee to begin with), climbed up in the back and as I leaned back to give her room, I could see her upper thigh. It was delicate and it was amazing how long her legs were. For a girl of medium stature, about 5’5”, it seemed her legs belonged to a woman a foot taller.
When she was finished, we went over it line by line. It wasn’t a terrible passage but there was some work that needed to be done. We changed things around and by the end, felt that the whole paper read a lot better. She thanked me and said she wished there was something she could do to thank me.
“Haha, you don’t have to do anything. That’s what they pay me for.”
“Yeah, but that’s the school thanking you for doing your job,” she said. “You have been so helpful to me, writing papers and writings for college applications. I’ve really needed you.”
“Well, I am glad I could help.”
“Well, maybe I can help you now,” she said mysteriously.
It soon became clear what she meant. She pulled my chair back away from the desk and stood right in front of me.
“Hillary, you know I can’t do this,” I protested, against my inner will.
“You can, you just shouldn’t,” she replied.
Lifting her long right leg, she put it between the seat and arm of my chair, and did the same with her left leg. Straddling me, she began to rock back and forth, rubbing her pussy against my cock, she still in her skirt and I still in my pants. It felt amazing but I couldn’t risk my job. I was terrified someone would walk in, though this was a few hours after school let out. Hillary was only there because cheerleading practice just let out.
“I could lose my job,” I stammered.
“There’s no one around, all the cheerleading girls have gone home,” she countered, grinding harder. She started to undo the top button of her shirt. She leaned in while she was doing that and started kissing my neck, softly.
“Mmmm, that does feel good…,” I said, relenting in my staunch stance. It had been a long time since I had been with a woman this young, not since I was beginning college. I remembered how exciting it was to be with a girl so fresh, so energetic. I pulled her off my neck and onto my lips and we kissed frantically on my chair.
Just as I had conquered my fear, a speed bump presented itself. The phone in her purse, which was on the desk right next to us, began to ring.
“Oh my god, what if it’s my dad?” she said, panicking a bit. She looked at the phone and whoever it was, it wasn’t her dad. She answered and yelled into the phone, “NOT NOW!”
I was afraid that this manic response would generate suspicion about her whereabouts and activities and I asked her who it was.
“Oh, just a friend, “she replied. “Just wanted to see where I was. Now where were we?”
Remembering where she was, Hillary hurriedly worked through the rest of her buttons and let her shirt fall backward onto the floor. Her bra concealed a perky set of B cups which she carried upon her slender build. The bra didn’t last long and fell upon the floor with her shirt. Pushing herself into me, I kissed her breasts and bit lightly on her nipples, then licked them. Her skin was smooth, delicious 18 year old skin. I slid my hands under her skirt, up her thighs and onto her ass. She bucked hungrily.
Suddenly she lifted herself out of the chair and pushed it away from the desk and dropped to her knees. The new position of the chair was in full view of the door, so I would rather have stayed behind the desk in case the door opened. When I brought this up, Hillary just laughed and told me again that everyone had gone home. Reaching up, she put her hands on my belt buckle and began to undo the clasp.
“I am going to suck you off, Mr. Bloom,” she cooed seductively.
She got my belt undone, unbuttoned my pants and slid down my fly. I was glad she decided to leave my pants on as I would have felt very exposed to the door if they were completely off, as if I wasn’t vulnerable already. She spat into the palm of her right hand, slid the front of my boxers under my balls, and started stroking me. Her hands were very small and delicate and felt light as she twisted my cock. She made sexy little moans, but giggled afterwards. She was still a girl, just more adventurous than most.
“Your cock isn’t wet enough,” she stated and worked up a huge ball of spit, which should let dribble out of her mouth, between her hands, onto the tip of my fully erect cock. It felt warm and got warmer when she used it to give me a perfectly slick handjob. She leaned over and gave one long lick from base to tip when I froze in horror. The doorknob made a noise, turned, and the door opened.
In walked Gwen, decked out in the same apparel as her sister, who kneeled topless on the floor in front of me. There was no hiding what was going on here. With my dick pointing straight to the ceiling and Hillary’s hands wrapped around them, it would be hard to argue that we were going over her paper. This was exactly why I wanted to stay behind the desk. I imagined Gwen running away and telling her dad, who would make sure I went to prison if I was lucky. Their father was a big man.
“How about now?” Gwen said.
The sisters gave each other a knowing look and grinned. Gwen’s statement made no sense until I remembered Hillary’s phone call from earlier. She had screamed “Not now” into the phone, which appeared to me to be a warning to leave her alone. In actuality, it was an alert to her sister that things were going as planned.
“Did you know about this?” I asked Gwen, too scared to move, my member still hanging out.
She laughed and said that she did. She walked over to us in, got on the floor and gave her sister a passionate kiss on the lips. I could see their tongues darting in and out. Gwen had short dirty blond hair and as I mentioned, more curves than her sister. Her breasts were easily a C cup, which I saw in all their glory as Hillary removed Gwen’s blouse and bra. They kneeled before me, sucking each others’ tits, rubbing each other and moaning, until I reminded them of the stakes.
“Gwen is 16, Hillary. I can’t do this. She’s a minor,” I said firmly.
“You really aren’t in any position to say no at this point,” Hillary said, reaching over and stroking my cock. “This is what we both really wanted.”
They walked over on their knees to where I was sitting and both reached for my cock. Hillary’s right hand and Gwen’s left were placed on my cock.
“Now spit on it and start twisting your hand like this,” Hillary instructed as she gave a demo.
“Wait, has Gwen never done anything like this before?” I asked.
“This is her birthday present from me,” Hillary replied. “I am going to show her how this is done. We picked you because we both think you’re cute.”
In hindsight, I should have refused but I was so horny and there were two beautiful girls in front of me willing to do about anything, that I simply sat back and accepted my wonderful fate.
“Alright Gwen, you take it now,” Hillary said as she moved her hand off of my cock. Gwen took me in both of her hands and twisted and pulled. She was doing pretty well, having taken instructions from her sister. Gwen had her arms at her sides to the elbow and worked me with her forearms and hands, so she was pretty close to me. Her arms being the way they were, her voluptuous tits were pushed together slightly framing them perfectly. I reached down and began rub them gently. She looked up and smiled shyly.
“How am I doing, Mr. Brooks?” she said sweetly.
“You are doing great, Gwen. Keep it up.”
“Actually,” Hillary chimed in, “I think it is time to move along. Let me show you the next step.”
Gently moving Gwen aside, Hillary moved into position in front of me. From the waist down, still in her little shoes, knee socks and green pleated skirt, she looked like the innocent girl I thought she had been. Clearly I was wrong.
“The most important thing for giving a really good blowjob is lots of spit,” Hillary said. “You have to get a lot built up in your mouth because that’s what feels really good for him. Isn’t that right?” she asked me. I agreed vigorously.
“Alright, watch me, Gwen,” she said as she started in on my dick. Hillary was certainly more experienced than I would have guessed and worked on my expertly. Her mouth was wet and moist and she worked all areas of my cock. She would take me down about half of my 8” and then would pull off and lick all around my shaft. My cock glistened, coated in Hillary’s saliva. She would also take quick little flicks to tease me.
“Alright, now you try,” she said and handed over the reins to her apprentice. Gwen spat on my cock twice to get it wet (though it already was, she was just doing as she was told), and began to take me down. She wasn’t as good as her sister; she was just putting her mouth on it and not sucking it hungrily like her sister did, but it still felt good. The idea of an inexperienced minor was growing on me and I relished the chance to be her first. I stroked her hair for encouragement as she worked and reached down for her breasts. She had more to offer in that respect than her sister and I wanted to take advantage. She licked me up and down until Hillary decided that she had passed that test.
“Make sure you work his balls too, Gwen. Guys love that. Work them with your tongue.”
I certainly did love that. Gwen slid down and got on all fours and tilted her head upwards to put her tongue on my balls. She swirled them around with her tongue and took them each individually into her mouth and sucked on them gently.
“Use your hands on his cock while you do that,” Hillary ordered.
Keeping her mouth on my sac, she began to jerk me off. Having her in two places rendered me incapacitated and I let out a groan.
“Ooh, that’s a good noise,” Hillary said to Gwen. “Nice job. Now I am going to show you the last thing for a blowjob. Not everyone can do this. It takes practice.”
Gwen backed away and Hillary moved in again. She looked up at me and smiled knowingly and raised her eyebrows. Putting her mouth on my cock, she began to work on me just like she did before. She got down to the same point where she did on her last blowjob, but continued to progress down slowly. 5 inches gone, 6, 6 and a half. I was vanishing deeper and deeper into her warm little mouth. With one final push, my cock was gone. Hillary had completely deepthroated me, and didn’t seem too hard for her either. My entire dick was warmed and wetted by her mouth. She hummed and made my whole cock tingle.
“Oh my god!” Gwen exclaimed.
“Your turn,” Hillary said as she pulled off, the strands of spit still hanging from her mouth. She breathed heavily as she got her wind back.
Gwen positioned herself over my cock but didn’t seem too confident. Slowly, she began the descent downwards. At 5” deep or so, she hit the wall and began to gag, coughing gently on my cock. She pulled off.
“I can’t do it!” she said, annoyed to be shown up by her sister.
“That’s ok, it’s hard at first, you have to learn the right angle,” said Hillary. “Try again.”
Again Gwen went down and got to the same point. Hillary, who had moved behind her, was giving her encouragement and when Gwen stopped, Hillary put her hands on Gwen’s head and pushed down. This caused Gwen to make a loud gurgling noise and she was pushed past the point of her comfort. The vibration of her voice felt great on my cock, but Gwen was struggling. Gasping loudly, she flung her head off my cock, sending spit flying, some of which landed on Hillary’s exposed tits.
“Oh my god, that is so hard,” Gwen whined.
“Practice makes perfect,” Hillary reassured her. “We’ll work on it. Let’s see, what should we do next?”
Hillary stood up and came behind my chair. She reached down and rubbed my stomach and chest then lifted my shirt up over my head. At the same time, Gwen dug her hands under the top of my pants and pulled off my pants, boxers, and shoes and socks on the way. Completely naked now in front of two girls still in their skirts and panties, I decided this wasn’t fair.
“Take off your panties,” I commanded, feeling more in control than I had.
“Oooh, yes sir. One thing you can do to get a guy going is to take off your clothes as sexy as you can. Let’s take them off together and we’ll let him see everything,” said Hillary.
With Gwen following Hillary’s lead, the girls faced away from me and hiked up their skirts so the bottom now only reached upper thigh. They bent over as far as they could to reveal their panties to me. Hillary was wearing a black thong and Gwen was wearing a lacy white pair, a devil/angel split that I thought was appropriate. Hooking their thumbs into their panties, they slowly pulled them down to their ankles, stepped out of them and threw them to the side. Gwen had a more rounded ass than Hillary, but both were firm and shapely. They then walked over to me, flanked me on either side and began kissing chest and neck and rubbing me around my cock.
“Let’s see what you’ve learned,” Hillary said, challenging Gwen.
They got down on their knees and both put their mouths on my cock, their lips cupping the side of me but making a complete circle with their mouths. They moved rhythmically up and down my shaft, jacking me off with their mouths only. They then broke this off and Gwen went for the top of my cock while Hillary shifted down to get the angle on my balls. She lapped at them lovingly and gently, knowing how sensitive they are and sucked on each one separately and sweetly. Gwen, becoming more excited by the minute, started sucking me voraciously. She sucked harder and harder and put her hands on my ass and started jamming me into her mouth. I could hear the same gagging noises from before but she didn’t stop. Hillary reached up around her sister and rubbed her back as Gwen’s spit dripped off my cock, down to my balls and into Hillary’s mouth and onto her face. Hillary began to suck as Gwen’s tits, which hung down into her sister’s face. The spit from Gwen’s blowjob was smeared all over her tits by Hillary’s mouth.
The older sister then put her hands on the outside of Gwen’s large breasts, squeezing them together while her little sister took me deep into her mouth. “Mmmm,” Hillary moaned. “Sit on his cock.”
“How do you want me to do it?” asked Gwen. She was completely submissive to her sister’s demands.
“Sit facing away from him,” Hillary ordered.
Gwen stood up and I got a good look at her in all her curvaceous glory. Her hips were hidden under her little skirt but her legs hinted as to what was up there. She turned around like when she had taken her panties off and lowered herself into my lap. I could feel the moisture from her anxious pussy on my cock and the warmth coming out of her. She lifted slightly, put her hand on my member and slid it into her. She let out a small yelp as she was entered for the first time.
“Yeah, we’re going to pop that cherry,” I said, now completely into the virgin idea.
Gwen bit her upper lip and groaned. Her pussy tightened up on my cock as she tensed her body. She put her hands on my thighs and began to slide around and I responded by pushing up slightly. I reached around and found the top of her pussy with my hands and started rubbing it quickly back and forth.
“aaaaaaAAAAAAAHHHH! It hurts!” yelled Gwen, enjoying it but being broken in.
“It gets better and better. Fucking ride him,” said Hillary harshly and moved to the side of the chair. I removed my finger from Gwen’s pussy and gave it to Hillary, who took it in her mouth to suck the juices off. “You taste so good, Gwen,” she said.
I was really bouncing Gwen now, her tits flying all around as our bodies slammed. I took my hand back from Hillary and put both hands on Gwen’s breasts and groped them hard from behind. Gwen put her hands on mine and leaned backward, pushing my cock to the front of her pussy walls. She gave a little whimper as I kissed her.
“My turn,” Hillary said. Gwen slid out and Hillary came over and slid her legs through the arms of the chair just like before. This time though, she took my cock and slid it into her pussy. She wasn’t interested in warming up slowly and started bucking rapidly. Her hips swung backwards and then slammed forwards over and over, as she moved the hair out of her face.
“Fuck me, Mr. Brooks!”
I moved my cock up to her as I had with Gwen and found Hillary’s pussy to be tight too, though not as tight as her sister’s. I slid my hands to her ass and clenched them, and slid a finger down the crack of her ass. This made Hillary laugh delightedly and squealed when I put my right index finger in her asshole. She was really enjoying herself and seemed up for anything. Her perky little tits bounced in my face and I sucked them hard. She squealed again. I decided that I would call the shots for a bit and get what I wanted.
“Hillary, go lie face up on my desk.”
Hillary hustled over to the desk and did as she was told. When I told her to hang her head over the side, she did that too.
“Time to get mouth fucked,” I said. “Take me all the way down. Gwen, your sister tasted your pussy. Time for you to learn what it tastes like. Go eat her out.”
“How do I do it?” Gwen asked eagerly.
“Just move your tongue all over and suck on it. Do it like you think would feel good on your own pussy.”
Gwen moved to the other side of the desk and kneeled down and put her head in Hillary’s crotch. I could see her tongue moving gently over Hillary’s glistening pussy and I saw Hillary close her eyes. I put my hands on either side of her face and moved my cock towards her mouth.
“Ready?” I asked.
“Give it to me.”
I moved my cock all the way down her throat. She could deepthroat pretty well earlier when she was doing it at her angle but with me in charge, she gagged a little. I pulled out a bit to give her time to catch her breath, but she took me by the waist and again put me to the back of her throat. She closed her eyes and moved her hand down to her pussy, where Gwen was working diligently.
“Open your eyes baby, let me see those eyes,” I commanded.
Hillary opened them and I could see that her eyes were watering from my shaft shoved deep into her mouth. I leaned forward and ran my hands over her neck, her tits, her stomach and her skirt on the way to Gwen’s head, which I shoved down into Hillary’s cunt. Gwen made a sound of protest, but I kept pushing.
“How does she taste?”
Gwen could only make muffled noises as Hillary made a high pitch sound, the vibrations of which felt good on my cock. Relenting, I came off of Gwen’s head and pulled my dick out of Hillary’s mouth. Her mascara had run down her cheeks a bit. She wiped it away as she breathed heavily.
Gwen stood up and rubbed her pussy, as she had been doing the whole time she was working on Hillary. I walked over to her and kissed her, tasting her lips coated in her sister’s juices. Hillary got up and walked over.
“It’s Gwen’s turn to get fucked,” she said.
“Put your right leg flat on the table,” I commanded. Gwen lifted her right leg and laid it out on the desk, her left leg straight down to the floor, making an L with her legs, her pussy exposed. With Hillary kissing her all over her back and sides, I slid my cock inside. I thrust forcefully into her walls, sore with the first use, and put my hands on her ass which faced right up at me. I squeezed her luscious cheeks together and pushed deep inside her and held myself there. She whimpered and buried her face in her arms, her tits smashed against the desk. The way her ass bounced rhythmically in front of me, I couldn’t help but smack it hard and she yelped every time I hit it. It became red with my force.
After a few minutes I just couldn’t take it anymore. This young virgin pussy fit my dick so snugly that I just had to shoot my load. I instructed Hillary to come over and get on the floor next to me. Knowing what was coming, she ran over, knelt down, and opened her mouth with her tongue out flat. I continued to pump Gwen hard for a few more seconds before I pulled out quickly.
“Watch how to take cum!” Hillary yelled to her sister. “Give me that nut!”
I groaned in pleasure as I swung around and took aim for Hillary’s mouth. Her eyes were closed, bracing herself, and I couldn’t wait to fill her hungry little whore mouth. With a mighty tug, I shot my hot sticky load into the waiting hole. She dutifully kept her mouth open to the last drop. Most of it landed successfully in her mouth, but some had missed the mark and there were strands of my cum hanging off her chin. She opened her mouth wide to show it to me and gargled it for my enjoyment. Spent, I leaned against the desk to rest.
“Come over here, Gwen,” said Hillary, enunciating poorly with a mouth full of jizz. “This is what cum tastes like.”
Gwen walked over to Hillary, both girls still in skirts and knee socks, and lay down face up with her head in Hillary’s lap. Hillary cradled her baby sister’s head with her hands and leaned over. The cum began to drip slowly out of her mouth and down into Gwen’s. The cum picked up speed as there was a lot in her mouth. Gwen was surprised how much was there and closed her mouth, not wanting any more since cum never tastes good to a first timer. The cum not caught in her mouth landed on her cheek and chin as she moved her head, and then dribbled onto her tits, already slick with sweat.
“Swallow it,” said Hillary sternly. With a big gulp, Gwen took it down and cringed.
“Now I want some,” said Hillary and moved down to lick the hanging cum off Gwen’s face. After all that was gone, she put her sister’s big tits in her mouth and sucked them clean. Gwen moaned with pleasure and fatigue. Hillary let the cum roll around in her mouth before taking it all down the hatch. She licked her lips; clearly she enjoyed it more than her sister.
“That’s what guys really like, Gwen. They love it when you swallow their cum.” Gwen nodded, still trying to get all the last of the jizz out of her mouth. I opened my arms out to them and they both came over into my arms. I was almost a full head taller than they were but they satisfied me completely. I hugged them to me and they kissed each other, both of their mouths still with the lingering remains of my satisfaction. We cuddled and laughed, my worries completely gone for the moment. Totally exhausted, we put on our clothes and the girls left before me so as not to arouse suspicion. We had made it through with no one catching us. I left about 15 minutes later, went to my car and drove home. I wondered if all of my students were that promiscuous.