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Introduction:

A Chaperone to New York City gets more than he expected from this band hottie
Day 1
How was I trapped into this? A couple weeks ago, I substitute for a week for the band teacher, and now I find myself chaperoning a trip half way across the country. The high school band had been invited to play for the Independence Day celebration in New York City, but at the last minute the parental sponsor that was supposed to help, bailed out on the teacher. Mrs. Stevens said that I had seemed to connect well with the teens, and needed a male chaperone, so asked if I wanted an all expense trip to the Big Apple. I had never been to New York, and didn’t really have much of a social life, so I accepted the offer. But then, I saw a bus full of wild noisy teenagers, and started to question my decision.

My hesitation changed just after loading up on the bus. Mrs. Stevens asked if I would be willing to sit at the back of the bus, to help keep the wild behavior at a minimum. Since we would be driving through the night, she knew that things could get a little out of hand once the bus got dark, and she was hoping to avoid having any girls knocked up on this trip. As I made my way to the back of the bus, the last seat was the only one that was still available; reserved for the chaperone I was told, and in it sat Samantha. Samantha was not your typical band geek; in fact, she was more like your typical cheerleader instead. She was absolutely gorgeous, but dressed just skimpy enough to tease every young teenage boy…and maybe the occasional 40 year old man. Now, I have always seen the attraction of soft young flesh, but I never really saw myself as the type of man that would actually pursue it; but when I took my place on the other side of Samantha on that bus, I couldn’t help but be captivated by her. She had slightly wavy blond hair, probably “B” breasts that were being held in by a bra that was slightly too small. Her pink blouse was unbuttoned just enough to show some cleavage, and she was also wearing a short white skirt that barely extended half way down her thighs. Her crystal blue eyes were emphasized by mascara and dark line of eyeliner. She was stunning. She turned her velvety smooth legs to the side as I slid past her into my place next to the mirror. I have to admit, if I’m going to be stuck on a bus with a bunch of teenagers for the week, I at least had the best seat in the house.

The beginning of the trip was the also the beginning of my trouble. Samantha was one active talker. She never sat still in her seat, but instead kept standing up and leaning over the seat in front of me as she would whisper little secrets into one of her girlfriend’s ear. That little skirt barely managed to keep her tiny little ass hidden from my view. I had constantly work to not stare at her ass, even though the nerdy little boy in the other seat had no problem staring at it each time she stood up. Other than being active, Samantha was also a toucher. Now, what I mean by that, is that every time she talked to a person, her hands seemed to rub on their arm or hands or legs; and that included when she would talk to me.

About two hours into the trip, the kids had managed to calm down a little, and Samantha decided it was time to interrogate the chaperone. She asked me about my wife, who I told her was working a lot lately, so I took vacation time to join them on this trip. She asked about my job situation, but I told her that times were tough, and that was why I had done some substituting. The more I talked to her, the more I realized that she was not only beautiful, but she was also quite intelligent in her own teenage girl sort of way. She was very pleasant to talk to, but it was always hard to completely focus with those young teenage tits teasing me, and her hand constantly resting on my knee.

We finally stopped at a convenience store to allow the kids to buy some snacks, and I thought that maybe I could sneak into a bathroom stall and relieve some of the tension that had been building up in my cock for the past few hours; but no such luck. The teenage boys had filled the restroom, and I knew there was no real quiet way to jerk off without being detected. The fact that my wife had all but given up on our sex life since her job took off, made my frustration all the greater. I had not had sex of any form or fashion in over a year, and my cock was dying for release. Masturbation was great at times, but it just wasn’t the same as a tight little pussy milking me dry. Frustrated and disappointed, I adjusted my cock in my jeans, and proceeded back to the bus. We had left pretty late in the day, and the sun was starting to set. I was hoping that maybe in a dark bus, it would be easier to avoid lusting after my sexy little riding buddy.

The next hour or so was much like the first, but slowly the teens started to quiet down again, and many started falling off to sleep. Samantha and I had started talking more about what she wanted to do with her future when she graduated at the end of the year. Though she loved band, she also loved singing and acting, and had hopes of pursuing some sort of theatrical career. She said she was going to school to become a nurse though, and figured that that was probably the more likely course of her life. Unfortunately, my mind immediately began fantasizing about this lovely thing coming in to my hospital room and “taking care” of me. Our conversation finally died down as she started talking to the girl in front of us again, but my cock did not. I turned toward the window, and began imagining Samantha as she came into my hospital room and proceeded to give me a sponge bath. I looked over at her and imagined her lovely blue eyes staring up at me as she decided to help herself to my cock, which had responded to her special attentions.

My cock started to rise in my jeans, and I knew that I had to stop fantasizing before I got in trouble; so I started playing games on my cell phone. About ten minutes into that, Samantha settled back into our seat, and laid her head on my shoulder as she watched me play. I could smell the sweet vanilla sent of her shampoo, and could feel her warm breath on my neck. “FUCK,” was all I could think, as I fought to repel the urge of my cock to harden again.

“Mr. Allen,” her soft voice whispered in my ear, “would you mind if I laid against you to take a nap? I am getting tired.” She was so sweet and kind in her voice, almost as though she was scared to ask me.

“Of course Samantha; and you can call me John.”

“Thanks John,” she said, smiling softly at me with her tender plump lips. I was so screwed.

The next hour, this little vixen cuddled up tight against me, holding on to my arm to assure that she didn’t slide down out of the seat as she slept. At one point, Mrs. Stevens worked her way to the back of the bus, and saw my position. She thought nothing of it, and even mouthed “Thank You,” as though this was my way of going the extra mile as a good chaperone. Damn, if she only knew how hard I was working to keep my cock from busting through my jeans.

It was getting close to midnight, and the bus was completely quiet. From the looks of it, everyone had finally drifted off to sleep in the dark bus, and even the few couples that were together had fallen asleep in each other’s arms. I was managing to sustain my lust, and even felt myself finally drifting off to sleep. The problem with sleep however, is that sometimes we lose the ability to control ourselves. I quickly began dreaming about Samantha and that sexy little body and those luscious little lips. I can only assume the nurse fantasy was too fresh in my mind, because my dream picked up where my imagination had left off earlier. Therefore, you can only imagine my disappointment when I was awoken by a gentle tap on my arm. I quickly realized that my cock was pressing hard at my jeans, and the tap on my arm was actually Samantha moving it out of the way, so that she could better lay down on my chest. Though I wanted to go back to my dream, the reality of my situation was more appealing. I stared down at my sexy companion, enjoying how close her face had now moved toward my cock. I was sure nothing would ever come of it, but that doesn’t mean that I didn’t enjoy the fantasies that were flooding through my head.

I started wondering if she was very sexual? She was delicious looking; she had to have had some young stud work to steal that virtue of hers. Did she suck cock? Her lips were perfect. Come on now, you know what I’m talking about; those perfect plump lips that you can’t help but think would be incredible as they worked up and down on your shaft. Blowjob lips in other words. And here they were a mere 6 inches from my throbbing member. I must have watched her for another half hour or so when I was just about to doze off again, when I heard Samantha’s voice whispering up at me…

“John…” she paused briefly.

“John…” I opened my eyes to stare down at her; those soft blue gems peering deeply into my own eyes.

“Yes, Samantha, what is it?” I asked, while also noticing that the bus was still dark and sleeping.

Before she spoke, Samantha pointed down at the giant bulge in my jeans; the one detail I had somehow managed to forget about for a moment.

“John, is…ummm…is that because of me?” She was still whispering, and to my surprise, not moving from off of my lap.

“Oh Shit!” I whispered back. “I am so sorry Samantha, I am so sorry.” I didn’t know what to say. I was clearly busted, and there was no possible way for me to deny the hard on that was still pressing violently at my jeans.

“I asked if that was because of me?” she again whispered back up at me. Her eyes were staring deep inside of me; almost with a needy kind of gaze. I was still not sure what to say. Of course it was because of her. Finally I just decided to be frank and honest about it, and hope she didn’t report me.

“Yes Samantha, it is because of you. Again, I am so sorry, it has just been a long time for me, and I guess the image of a beautiful young woman on my chest got me worked up.” I stared back intently now, knowing that my accuser was about to shout out to her teacher. But that is not what happened at all.

“John…ummmm…can I ….ummmmm…” her words were stuck in her throat, and I had no idea what she was actually going to ask.

“John, can I touch it?”

What the Fuck? Was she kidding. Of course every part of me wanted her to grab it and never let go; but the other part of me was smart enough to recognize the position I was in at the moment: I was on a school bus surrounded by teenagers, and I had a 18 year old senior girl snuggled up in my lap. I was going to jail for sure. I just stared at her for a moment, feeling my cock harden even more against my jeans. I know what you are thinking, but it was not that simple of an answer to give. And to my surprise, Samantha decided not to wait for my answer anyway.

Without warning, Samantha reached over and began stroking my shaft through the course fabric of my jeans. My cock twitched against her hand through the fabric, causing her to jump and giggle a little. For a moment, she decided to scan the bus herself, making sure that no one was awake to watch what she was doing. She grabbed the little blanket that she had stuffed behind her head, and laid it over her shoulders, helping to hide her hands and face from view.

“I won’t tell if you won’t tell John,” she whispered up at me. Again I just sat there quiet, not sure exactly how much trouble I was about to get myself into.

Samantha moved her hand back to my jeans, only this time slowly began unzipping my zipper. For a brief second, common sense came over me, and I reached down to stop her. But Samantha wouldn’t have it. She pushed my hand off to the side, and gave me naughty little nod, and mouthed the word, “No.” Even if I wanted to resist her, I knew that there was no way…I was just too far gone.
Her soft fingers rubbed against my shaft through my briefs, and then slowly started to pull it through the small opening in the front of them. All I could do was continue to stare as this beautiful creature released my cock to the open air. My cock was about 8” long, and was quite thick. It twitched again as Samantha wrapped her tender fingers around it and gently began to stroke it.

“You have a beautiful cock John…thank you for letting me touch it,” she again whispered up to me.
What teenage girl thanks a 40 year old man for getting to touch his cock. I was melting like butter, and I think Samantha knew it. I continued to watch as my young beauty stroked her hand up and down my throbbing cock. Her eyes would stare intently at my cock, and then shift up to where she was staring deep into my eyes as her hand slowly and methodically worked every each of it. I fought the urge to moan; worried that someone might hear me. Finally, she looked right at me, and then in one quick movement thrust her mouth down on the head of my shaft. Her lips locked tight around my shaft as her tongue began teasing and thrusting eagerly around the tender tip.

I belonged to her, even if she didn’t know it. Slowly she began devouring my cock with precision and skill. Her hand continued to stroke up and down on it as she worked to get more and more of the 8” inside those plump luscious lips. She knew what she was doing. My hand moved to the back of her head, and I gently ran my fingers through her silky smooth hair as I helped to guide her up and down on my shaft. Unfortunately, I knew there was no way I was going to last very long in this sexy little teens mouth.

“Samantha,” I whispered, “If you keep that up, I’m going to explode.”

Samantha stopped her actions for only a second as she looked back up at me with those eyes; “Let’s just hope it’s not the only time you feed me cum this week John.” She gave me a flirtatious wink, and then once again buried her head into my lap. Her mouth was more insistent this time though, and she began to pump even more aggressively upon my cock. I kept scanning the still quiet bus, as I worked to keep her blanket up as a convenient curtain.

Samantha was feasting on my shaft now, and even managing to force it most of the way down her throat. I could feel my balls tightening and gave her a slight push downward on the back of her head as I shot my first load of hot cum into her mouth. Samantha eagerly swallowed it down and continued to pump my cock between her lips. Spasm after spasm filled her sexy mouth, and my little vixen swallowed every last drop of it.
My body was shaking as she sucked me through an orgasm like I had never experienced before. Even after I had finished shooting cum, Samantha continued to clean and lick at my still throbbing member.
Finally, I pulled her up against me chest, and smiled happily at her.

“Samantha, that was the best blowjob I have ever had.” I whispered. “You are incredible.”

Without saying a word, Samantha leaned forward and kissed me on the lips. The salty taste of my nectar was still on her breath, but that did not stop me from pushing my tongue into her mouth and savoring her. Her hand was still on my cock, stroking it gently as I reached up and slid my hand up under her blouse. Her body trembled as I worked my fingers beneath her little bra, and forced it up over one of her breasts, allowing it to be available to my touch. Even as we kissed, I scanned the bus to make sure no one was watching us. I adjusted her blanket, and slowly began kissing down my little lover’s neck, and then hiked up her blouse to reveal her naked breast to me. Her little swollen nipple stared up at me, almost begging to be sucked. I quickly drew it into my mouth and savored the sweet taste of her young teenage flesh. Samantha buried her head into my shoulder and moaned as I teased it with my tongue and gently nibbled at it with my teeth.

For a few moments, I just savored her nipple in my mouth before returning my lips back to hers. She was breathing harder than before, and I could feel her trembling against me. I turned her back into the seat, and then turned myself to face her. The blanket was covering both of us as I slowly slid my hand down her body to her thigh. My fingers massaged at the soft tender flesh as they slowly began to work their way up beneath her little white skirt. Samantha happily parted her legs for me, allowing my hand even better access. Her eyes were staring intently at me again as my first finger brushed up against her swollen clit. She gently bit at her bottom lip to keep from moaning, but never broke her gaze from mine. My finger gently teased and massaged at her sensitive clit, causing her hips to involuntarily begin to move beneath her.

I was enjoying the power that I now had over her. Slowly I began to press a finger between her wet tender lips. She started to moan out, but I quickly pressed my mouth against hers and thrust my tongue inside. At the same moment, I thrust my finger deep inside her wonderful little slit. It was so tight as it locked around my finger. Her hips were slowly thrusting back and forth in her seat now, helping her to fuck herself on my digit. I pressed a second finger at her tight little pussy, and gently pushed it inside of her. Samantha thrust her tongue inside my mouth as her hips were now pressed tight against the back of the seat. Then slowly I began to finger fuck my little lover.

Samantha responded almost to eagerly to the invasion of my fingers. Within only about a minute, she was exploding in orgasm against my hand, and her nectar covered my fingers. I had to pull her tight to my mouth, so that her moans were lost in our kisses as my fingers continued to feverishly pump in and out of her tight little hole. She was shaking violently against me as I began to finger her even faster and deeper. Her tiny frail body was helpless against my attack, and she began gasping in my mouth a second time.

Finally a withdrew my fingers from her slit and happily sucked the nectar from them. She had the sweetest juices I had ever tasted. My cock was as hard as a rock again, and I was dying to drive my cock in this young beauty when I saw the bus turn toward a gas station. I quickly hid my cock back in my jeans and helped Samantha to freshen up before the other kids started to wake up. By the time the bus driver turned on the lights in the bus, I was facing the window, and Samantha was feigning as though she was still asleep on my shoulder.

One by one the kids filed out of the bus, but Samantha waited till we were the last one’s left, and then turned around to face me. “John, before this trip is over, you are going to fuck me with that wonderful cock of yours. And just for the record, I have given blowjobs before, but you are the first man I ever swallowed; and it was delicious. I hope I can have more.”

I wanted to grab her and fuck her right there, but instead I told her to go get herself cleaned up. As she smiled and turned away, I quickly slid my hand beneath her little white skirt and let me fingers tease the crack of her ass. Then I whispered in her ear, “Don’t worry baby girl, before this trip is over, I’m going to make you mine over and over again.”

“John, I am already yours.” She whispered, and then quickly rushed off the bus.

Day 2

The rest of the night consisted of Samantha and I cuddling on the bus beneath the covers. The irony of the situation was that the teacher continued to thank me for helping her out. She thought it was sweet how nice I was being to Samantha letting her sleep on my shoulder and all. If she only knew!

Before the sun came up, Samantha had woken up and once again treated me to another amazing blowjob. It was a great way to start the day, let me tell you. It would seem that luck was always working in my favor to. When we finally reached New York City, Mrs. Stevens insisted that everyone have a partner for the day. Since there was an odd number of students, Samantha asked if she could be my partner, since she was having so much fun talking to me on the bus. Mrs. Stevens asked me if I minded, and I teasingly acted like it would be an inconvenience, but then told Mrs. Stevens, that I was happy to oblige. Again she thanked me.

What a dumb woman.

Our first trip was to a large art museum, and the kids were all told that they could go wherever they wanted, so long as they stayed with their partner and did not get into any trouble. I can assure you that staying with my partner was not a problem, but the trouble part may have been. Just before Samantha and I headed off, Mrs. Stevens pulled me off to the side, and explained to me why she was so thankful. Apparently, Samantha’s parents had recently divorced, and she had been taking the move rather hard. Her dad had basically abandoned her and her mother, and Mrs. Stevens thought it was great that she had a male figure that she could turn to. She told me to let her know if she became a problem, but that she really was grateful that I had decided to come on the trip. By this point, believe me…so was I.

Samantha grabbed me by the hand and pulled me off into the museum, leaving Mrs. Stevens there with the bus driver. For a while we just walked into each of the exhibits, and would playfully grab at one another when no one else was looking. I tried to stay conscious of the different cameras, but must admit, that it didn’t take long before my cock was starting to stir again. Samantha had changed clothes before we got to the museum, but it was much like the last outfit in regards to the teasing factor. She was wearing another short skirt, this time denim with frayed edges, and a green tank top with no bra. Her perky “B” breasts could easily get away with that. I couldn’t stop from noticing her hard erect nipples. It was as though they just stayed that way, constantly poking at the thin fabric of her tank top. Occasionally, I just could not resist the urge to twist and pull at them when the no one was around.

As we worked our way to the back of the museum, I noticed that there was a section that seemed to be marked off for renovation; it was a new section of the museum that was still being added on to, but from the looks of it, was not being worked on today. There were no workers around, and from what I could tell, no cameras had yet to be installed. They had hung long black plastic sheets from the ceilings to discourage people from going into the closed off section; but for me, all I could see was opportunity. We still had at least an hour before we were to meet at the bus for lunch, and I could not stop fantasizing about filling Samantha’s pussy with my cock.

“Were you serious about wanting to fuck me Sam?” I asked, smiling down into those lovely eyes of hers. As soon as she realized what I meant, a big smile crossed her face, and then she scanned the area for anyone that might see us.

“Heck yeah, John. I haven’t stopped thinking about having you inside of me. But, ummmm…what if I get…you know…pregnant?”

“Don’t worry baby girl, I have already had a surgery to take care of that. No little babies from John…just orgasms.”

Again she smiled eagerly at me. “Well, I am happy to let you give me all of those you like.”
With that, I checked for other people again one last time, and then quickly pushed her behind the dark black plastic sheet. I surveyed the area one more time, and quickly found a place toward the back of the room that both offered more protection from being discovered, as well as a little bench that would help position upon. I quickly led Samantha back to the bench, but instead of sitting down, pulled her tight against me. My mouth quickly found hers and our tongue began dancing happily together. My hands slid down her body, and slid beneath her denim skirt to her tight firm ass. She moaned into my mouth as my fingers began teasing at her crack, and massaging at both firm cheeks.

As I kept one hand on her ass, the other one slid back up her body, and then eagerly found its way beneath her skimpy tank top. Her soft flesh felt so good as it moved through my fingers. We were far enough from everyone, that she finally felt safe enough to moan as my hands explored her body. Samantha started to drop down on her knees, but I stopped her and pulled her back up.

“No doll, now it is my turn,” I said, guiding her down onto the bench behind her. I knelt down between her legs, and hoisted her tiny little skirt up over her waist. Her soft blue eyes gazed intently at me as I slid her skimpy panties down her legs and onto the floor. Her pussy was trimmed just like a model you might see in playboy magazine. Her soft womanly lips glistened from the nectar that was already showing her excitement. Gently I leaned down and traced my tongue very gently over her slit, be careful not to apply much pressure. She squirmed and moaned beneath me. Her sweet juices covered my tongue like honey and I slowly repeated the motion. My hands spread her legs further apart and then began to slide up her inner thighs.

Again she moaned as she closed her eyes and relaxed her head down. My fingers gently began to rub and tease close to her clit as my tongue pushed a little harder at her pussy lips. They eagerly parted open, welcoming me to explore deeper. Slowly I began to feast on my young beauty’s flower; eagerly savoring every drop of nectar it offered me. My thumb began to gently rub at her clit as I began to push my tongue inside her sweet pussy. Samantha’s hands grabbed the back of my head, and began to massage it with her fingers as she moaned softly in pleasure.

I pressed my tongue even deeper into her slit as my thumb and finger began rubbing and teasing her clit more aggressively. Samantha began bucking her hips up to meet the thrust of my tongue, forcing it even deeper inside of her. I reached up with my other hand and gave her hard swollen nipple a sharp twist. The sensations of enjoyable pain shot directly to her pussy, and before I knew it, she was exploding her wonderful nectar into my mouth. Hungrily I feasted on every bit of it as she thrashed wildly beneath me. Her tiny body was so sexy as it shook from the attention.

My cock was throbbing in my jeans, and I knew it was time to do something about it. The bench was too low to the ground to really serve my purpose, so I stood up and then pulled Samantha to her feet before me. Her mouth quickly went to mine and once again our tongues danced together. I loved kissing this beauty, but the fact was, I just wanted to feel my cock in that wonderful pussy of hers. I broke our kiss and spun her around, pushing her forward against the bench. Samantha offered no resistance as she spread her legs and waited to feel me take her from behind. I quickly undid my jeans and pushed them down to my knees. My hard on sprang instantly to attention, and eagerly came to rest against Samantha’s soft silky ass. For a moment, I pulled myself tight against her, allowing her to feel my hard cock pressed against her skin. She moaned out again, as she gently wiggled her ass against it.

“Fuck me John; I want to know what it feels like to have a real man fuck me.”

I didn’t say a word as I grabbed my cock and guided it to her sexy little slit. Samantha held tight to the bench in front of her as I began to push the thick fat head of my cock into her tight tender slit. Her moaning was so sexy as I pushed inch after inch inside of her. She was so fucking tight, that I finally had to grab onto her hips to help me force myself the rest of the way inside.

“Oh fuck, fuck, fuck,” she mumbled as inch after inch of my thick cock spread her tight cunt open. “Oh fuuuuuuuccckkkk John, it feels so …ummmmmm….ohhhh fuck ….mmmm…good.” Her sweet voice using a word like “fuck” just turned me on even more, and I began slamming my cock hard and deep inside this little vixen. I pulled back on her hair as I drove my cock in faster and harder, causing her to explode in an even more violent orgasm than the previous one. Her tight little pussy was squeezing me like a vice, and I only wanted more.

I must have pounded that sweet pussy for at least ten minutes before I finally felt my balls tightening.

“I’m going to fill your pussy baby…are you ready?” I asked, not really expecting an answer.

“Fill me John…please fill me with your hot cum.” She begged.

With that I began pumping even more furiously inside my sexy school girl. My sperm fired from my cock like a missle. Wave after wave of steamy cum shot into Samantha’s sexy little slit, and I fucked her harder and faster with each spasm. Finally, my knees started to weaken and shake, so I thrust hard and deep inside her and then just held her tight as the last of my cum emptied into her pussy.

“Oh John, that felt so good,” she moaned as I stepped back and helped her to her feet. “But I’m not quite done with you yet. We still have a half an hour.”

With that, she spun me around and pushed me down on to the bench, and quickly dropped down to her knees in between my legs. “Now I can get at the luscious cock like I have wanted to all day.”

Her hand grabbed my wet cum covered cock and quickly guided it into her wonderful mouth. Her tongue and lips masterfully worked up and down it, eagerly cleaning our combined cum from its entire length. One of her hands moved down to my balls and began massaging them before finally moving her mouth to them, and then sucking the tender little marbles into her mouth too. This lovely little teen knew how to suck cock. In just a couple minutes she was deep throating it and making some of the sexiest little gagging noises as she fought to get it deeper and deeper down her throat. I must have lasted at least 15 minutes before she had finally pushed me over the edge all over again. She was aggressive with her sucking, making sure to not let me relax through it. My entire body quaked with pleasure as she feasted on another load of my thick cum.

After she was sure she had milked me completely clean, Samantha stood up and pulled me to my feet. We both quickly got dressed, and shared one last deep long kiss before sneaking our way back into the museum to join the others. Luckily, it seemed that no one had even noticed we had disappeared. Something told me that this was going to be a great week in New York.
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