Schoolgirl's First Subway Ride

I'm so excited! I've been homeschooled my entire life. Since I just turned 18, my mother finally let me attend school, an all-girls private high school on the other side of town. For my whole life it's been just me and my mother at home. She's my best friend and a good teacher, but she never leaves the house. She lets me run errands such as grocery and clothes shopping. I've been out of the house many times, but it's a struggle to fit in and feel "normal" in the outside world. Most of the neighbors think she's a weird recluse, and I'm avoided by association, so I don't have many friends.

Since my mother doesn't leave the house and my new school is across town, I have to take the subway to school. Today was my first time. We went over the rules and procedures in detail before I left. I was to walk straight to the subway station, buy a ticket, and not talk to anyone. My mother is paranoid that all strangers are out to get us. I wasn't scared; I was thrilled! The morning of my first day I got dressed in my school uniform: plaid skirt, knee-high white socks, a white blouse, ponytail, and ballet flat shoes. My chest had grown recently, so the blouse was a little small, but it was the only one I had.

I used the subway and arrived at school without any issues. My first day of school was a little boring, but I'm still grateful it was different than my typical day at home. All of the girls at the school seemed so glamorous. They wore tons of makeup and high-heeled shoes. I even saw the outline of a girl's lacy pink bra under her shirt. It made me embarrassed of my ponytail and white cotton undergarments. My mother hadn't prepared me for fitting in.

After school I was waiting on the subway platform and I noticed a man staring at me. He looked nondescript, like someone's uncle: tall, early 60's, glasses, thick around the middle, and wearing slacks and a plaid button-up shirt. I became self-conscious as he kept staring. Do I have toilet paper on my shoe or is my hair all messed up? I tried to ignore him, but I was getting more and more uncomfortable. I think he might be staring at my shirt. As much as I try to fit in, I know it will still be obvious to some people that I'm awkward in public.

*****

There was this cute young schoolgirl on the subway platform today. She was just my type: 100 pounds soaking wet, 5-foot nothing, innocent to a fault, and alone. I couldn't help but stare at her because she looked so wholesome in her schoolgirl uniform. Her blouse was too small and was gapping in the front. I had a great view of her cleavage and white cotton bra. My mind kept trying to imagine her without the uniform on. I bet she wears cotton panties too. I felt the bulge in my pants grow just imagining it. I hadn't had a schoolgirl in months. Good thing I drank some liquid courage after work. Today is the day! I must have her.

*****

When my train arrived, it was already full, but dozens more people pushed their way on board. I thought about taking the next train, but my mother was expecting me home in 40 minutes and she'd be hysterical if I wasn't there. I ended up standing near the middle of the train, near a row of seats. People were surrounding me from all sides and I was feeling claustrophobic. I just had to keep reminding myself that this is normal and happens everyday. Everyone else seemed at ease, so I tried to follow suit, even though I started to panic.

As the train started moving, I took in my surroundings. People of all ages and genders were pressed up against me, and none of them were paying any attention to anyone. Most were absorbed on their phones or had their eyes closed. I noticed that the plaid-shirt man who was staring at me was sitting in the seat directly next to me. With much effort, I turned and faced away from him hoping he hadn't seen me. As I was trying to calm myself, I felt something touch my thigh. It was brief, so I figured someone was adjusting their bag. Then I felt it again. This time I knew it was definitely a hand rubbing my inner thigh. I looked around to see if anyone noticed or also felt it; it appeared no one did. I tried to turn around to confirm that it was the plaid-shirt man who did it, but the crowd was too thick to move.

His hand was rubbed up and down my thigh. Maybe this is normal. Maybe he can tell that I'm nervous, so he's trying to calm me. I breathed deep and tried to just enjoy the comforting sensation. Just as I was beginning to calm, the whole car lurched and I was thrown forward then backwards. First I smacked the back of the person in front of me, then I landed on the lap on the plaid-shirt man behind me. I apologized and tried to stand up, but he was holding my hips. He said in my ear, "Don't worry about it. It's awfully crowded on here; you can sit here if you like. I don't bite." He saw my hesitation and began stroking my thigh again. I didn't want to be rude if this was normal subway etiquette, so I stayed seated. I looked around and once again, no one was paying any attention. The petting was actually making me feel better.

I sat there, swaying with the train, mesmerized by the rhythm of his hands. Before I knew it, his hands were sliding up under my skirt. When I looked down I couldn't see anything since the skirt was blocking the view. He was getting close to my crotch. I'd never been in this situation before, so I let him. His hands were smooth and somewhat gentle. My nether regions were beginning to feel kind of tingly and strange. I could feel his breath on the back of my neck. He was starting to breathe harder and I could smell beer on his breath.

As I sat, I could feel something under my butt. It felt like I was sitting on a sunglasses case, but it wasn't there just a minute ago. Was that his penis? My mother taught me the basics of where babies come from (man inserts his rigid penis into a woman's vagina), but why would this unknown man want to make a baby with me? Maybe it is a lot more common than my mother told me. I was so confused.

As I puzzled over how to handle this situation, the man began rubbing my crotch over my underwear. I was surprised that it felt good. My heart started to beat faster. Then he slipped a couple fingers under my underwear and began to massage my crotch. What the heck?! What is happening? His penis also seemed to be growing bigger and I was sitting on a huge lump in his pants.

*****

I kept an eye on the girl as she boarded the train. Without her knowing, I gently herded her towards the middle seats. And I was in luck, one seat was vacated just as we approached. I knew if I sat while she was standing, I could employ the ol' sit-n-grind method. Skirts are perfect for that. I just had to play my cards right, so that she didn't become alarmed and alert the other passengers. Stay cool.

When she was standing in front of me, with that delicious teenage ass in my face, I couldn't help but to reach out and touch her. Her thighs were so silky smooth. It took all my effort not to shoot my load right then. Then the whole train lurched and she ended up in my lap by a stroke of good luck. She seemed very nervous and green, maybe even a virgin. When I asked if she wanted to stay in my lap, she did. I'm a better actor than I thought!

She stayed put even as my dick grew into a cement rod in my pants. And this girl was either stupid, incredibly innocent, or slutty because she let me massage her sweet little cunt. She must be innocent because I was right; she wore simple cotton panties. My fingers slid around in her pussy like an ice rink she was so wet. I could feel her breathing getting harder. I had to start thinking about my grandmother in order to not come too soon.

I was going to explode if I didn't get inside her soon, so subtly shifted her weight and unzipped my pants while the other hand was still massaging her. The whole movement was swift since she weighed next to nothing. My dick was so hard, it just sprang out of my trousers without any coaxing.

*****

The man shifted his weight and I thought maybe I was squishing him, but as he settled again, I could feel something that wasn't there before. And when I looked down, my skirt was tenting up with a rod underneath. That must be his penis. He slid my underwear to the side with his fingers.

His hips began rocking underneath me and his penis began sliding up and down my crotch lips. I was confused, but it felt really good. It was pretty moist down there, and I wasn't sure if it was him or me producing the liquid. One time about a year ago I woke up from an arousing dream and my crotch was really wet, so maybe it's me. He was also rocking my hips back and forth, so that there was a lot of friction.

Next thing I knew, he grabbed my butt and lifted me off his lap a few inches. Then when he set me down, my crotch hovered right over his penis. Oh no-he is going to insert his rigid penis into my vagina! I had no idea it was going to be like this. I pictured sex being with my future husband on our wedding night on a bed. My mother had a lot of explaining to do when I got home.

He pulled my hips down and suddenly his penis was inside of me. There was a sharp burning pain for a second, but it subsided quickly. He wrapped his arms around me like a bear hug then pulled me down lower onto his lap. I thought he was inside of me as far as he could go, but I was wrong. It felt like his penis was skewering my insides. I thought for sure something was wrong. I looked around again and still no one noticed. Everyone's backs were to us and the train was so loud that our breathing and my squeal of pain couldn't be heard. Plus my skirt still concealed everything.

His arms lifted and lowered me onto his rod. I had no idea where all the liquid came from, but I was glad it was there. It made the sliding in and out less painful, almost nice. The man removed one of his arms from my waist and put his hand back under my skirt. He began massage my crotch again as his penis went in and out. This was really starting to feel good. Maybe even great! The tingling turned into a pressure building in my crotch. I needed to release it. I started using my legs to help us go faster and deeper. It felt so good. Without even realizing it, I was panting and moaning involuntarily. The man was breathing fast and hard. He had his mouth to my ear and was saying,

"You like that, you dirty little schoolgirl?

You like riding daddy's cock hard and fast?

I love your tight little pussy grinding in daddy's lap.

You ready to take my load?

Fuck me! Fuck meeeee!"

As he was talking, the pressure in my crotch was reaching an unbearable point. I was going up and down faster and faster.

"Oh my gosh! Yes! Yes!

More please!

I'm going to explode," I hoarsely whispered.

Then I felt like I exploded. My mind went blank and my whole body shook. That was the best feeling I've ever experienced. After I stopped shuddering, my body went limp.

*****

Just to make sure she was lubed up, I rubbed her pussy with my dick for a minute, but I knew I couldn't last long. So I lifted her up and just slammed her down onto my cock. Oh man, that was tight! I figured she was a virgin, and sure enough. After a few pumps, it was like a slip-n-slide she was so wet. I decided to throw her a bone and rub her clit while I raped her.

She loved it! She started bucking up and down like a cowgirl. She was going faster and harder with every pump. I wasn't going to last long at this rate. Fortunately she came right as I did. While she was shaking and shuddering her way to climax, I buried an 8-roper inside her sweet, young, and freshly deflowered biscuit. It was heaven!

*****

I could feel something ooze out of my crotch. I don't know what just happened. I looked around embarrassed. I lost control for a minute and who knows what it sounded or looked like. Thank God no one was looking. When I realized that I wasn't doing anything out of the ordinary, I relaxed a little. That was amazing! I'm going to have to find a book to tell me what just happened. Since my mother didn't tell me about it, she either doesn't know, or doesn't want me to know.

His penis was still sitting rock hard inside my vagina. I wasn't sure what was supposed to happen then. The man whispered, "Little girl, it appears like my one-eyed monster isn't quite done with you yet." With that, he picked me up and spun me around to face him, his penis still inside me. As I faced him, I wasn't impressed. I don't know what I expected, maybe my future husband, but this definitely wasn't it. The man's face was swollen and pink from too much food and drink, he had 5 o'clock stubble, and his breath smelled more powerfully like beer than I first thought. I almost cringed away, but then I remembered not to be rude. He said, "I gotta have a taste of these titties before we finish up." He untucked my blouse and slid his hands up under my shirt and under my bra. His smooth hands squeezed each of my breasts then he began to knead them.

He looked around to see if anyone was watching. No one was. So he unfastened my top two shirt buttons and pulled down my bra to barely expose my nipples. He leaned forward and began circling one nipple with his tongue. I looked at this with confusion, but right as his mouth landed on my nipple, I threw my head back and moaned. My crotch started to tingle again. I had no idea how sensitive my nipples were. His mouth went back and forth between the two, circling, licking, and sucking. It was the second best thing I'd ever felt.

His penis was throbbing inside of me, but not moving. As he sucked my breasts, I was so absorbed in the feeling that I barely noticed him lifting my hips again and his penis is sliding out of me. Just when I thought we were finishing up, he slid my my underwear over again, and I felt his penis hovering right around my anus. Why in the world would he want his penis anywhere near my poop hole? As he mouthed my breasts and I was contemplating this, he pushed his penis into my butthole. I squealed in surprise. Nooo! It didn't feel at all good. It felt like he was squeezing a 2-inch wide pole into a 1-inch wide opening. I was pretty sure I felt tearing.

I tried to push him away and get up off his lap, but he held me firmly. He said, "You don't like anal sex? But my monster does. It's his favorite. You don't want to upset the monster, do you?" As he said that, he lowered his chin and scowled at me, as if making a threat. I started feeling helpless. Anal sex? I'd never even heard of it.

He took my hips and pushed them down, so that his penis was all the way inside my ass. Fortunately it still had some lubricating liquid on it from the sex. He slowly lifted me up then pushed me back down onto his rod. As we continued, my muscles loosened and it didn't hurt as bad. Then he continued sucking my breasts. The more he did that and sliding in and out, the less I disliked it. As a matter of fact, I was starting to enjoy myself. He could sense my enjoyment, so he started moving faster, bouncing me up and down. After a few minutes, I was bouncing myself voluntarily. Since he didn't need to use his hands for force anymore, he lowered one and started massaging my crotch again.

With the sucking, massaging, and bouncing, I could feel the pressure building in my crotch again. The man was starting to pick up the pace too. He said,

"I knew you'd like anal sex.

You're hole is so tight; better than I expected.

Come for daddy!

Harder! Faster!"

I obeyed him and bounced harder and faster. After several more pumps, I once again exploded with pleasure. This time it lasted for a long time. I'm pretty sure I yelled out loud, but I can't be certain. After the pleasure subsided, I slumped forward onto the man's chest.

Just as I regained my bearings, I opened my eyes to see that my stop had arrived. In a panic, I pushed my way out of the train car and made it to the doors just before they closed. I stood on the platform looking into the car as the doors closed. I could see the plaid-shirt man zip his fly then blow me a kiss. My underwear was soaking and my body felt drained. I looked down at my outfit and the only thing amiss was the two unbuttoned buttons on my blouse. Was that a normal afternoon on a subway train? My mind raced in all directions, but ultimately I decided that something that felt so good couldn't be bad, so I started to walk home as if nothing happened. I wondered if I should tell my mother.

*****

After coming hard, my pecker wasn't softening. I thought back to the last time I had sex. There was that hooker two weeks ago, but she was a snooze. Why don't more people do this?-free spontaneous sex with a schoolgirl is 100 times better than high-priced sex with a hooker. My junk hadn't seen action like this tiny girl's cunt for at least 3 months, and he wanted to keep going. I couldn't let the opportunity slip away. While the girl was recovering, I spun her around and starting going at her tits. Her tits were a spectacular size-C's with perky teenage nipples. As expected, she loved it.

My ultimate goal was anal sex, so I just had to go for it. It was easy: I just lifted her up, scooted her soaking panties out of the way, and plunged my cock deep inside her asshole. Oh man, that was the tightest asshole I've ever felt! It almost felt like I was tearing her. Thank God for all her slippery juices mixed with my jizz making the entry a breeze. She tried to escape, but I wasn't going to let all that hard work get up and run away. After I played with her tits and clit, she calmed down and started doing all the work for me. She rode my cock like an expert with titties bouncing in my face. I was so absorbed that I didn't care if anyone noticed us at that point. After only a few minutes of grinding, I could tell she was getting close to coming. Right as she orgasmed, I shot a huge load into her virgin ass.

I guess she had to leave because she immediately got off my lap and ran to the door. I could have been upset that she escaped, but how could I be mad after I just popped this young schoolgirl's vaginal AND anal cherries? And the fact that she enjoyed herself was icing on the cake. It was the best sex I'd had in years. I'm not sure if the next victim will be as easy and willing, but I'll keep trying. The subway is the perfect place to "meet" people.