Train Trip, Part 1: One Day in Chicago with a HotOrNot Slut [MF]

So this is going to end up a trilogy. When it took place, it was the summer after I’d just turned 21. I was still living in the tiny rural midwestern town I’d grown up in, and was working at an office with about six employees. I had two weeks of paid vacation that had to be taken separately, because they couldn’t afford to let anybody go for two weeks at a time. Sucked.

Either way, I was still hooking up with my high school sweetheart, a year older, from time to time, and occasionally meeting a slim blond from the Chicago suburbs I’d found on HotOrNot, a year younger, who was happy to drive to meet me and split the cost of seedy motel so we could both be away from our parents and she could get treated the way she needed. It was weirdly romantic, fucking her like I hated her made her feel loved and she was addicted to it, and we’d both been enjoying trying some things out on each other for a couple years now.

More generally, though, I was getting bored, and I was jerking off way too much. The local girls were usually either churched up and prudish or trashy and halfway to jail. I didn’t fit in with either crowd. So there I was, 21, with one week off, and I was going to make the most of it.

I’d never seen New England, so I arranged to crash with a cute divorced single mom I’d been flirting with online, maybe 27. She was excited to spend the Fourth of July together and wanted me to barbecue for her, and I told her I needed to stop to visit a friend on the way so would be taking Amtrak. The truth was that I just wanted to stop in Chicago and bang out HotOrNot Girl again before she went back to college.

Then there was Maria. She was 33 now, working in finance in Manhattan. We had connected online over politics when I was 19 and talked on the phone late into the night every week for months. She was educated and accomplished, upbeat and energetic, and looked pretty and fit in her pictures. I couldn’t really figure out why she spent so much time on me, but talking to her had been really eye-opening about the world away from home.

Then, one day, she got a new, more demanding job in mergers and acquisitions and fell off the radar. I had hardly heard from her in a year, and since I had to change trains at Albany anyway, I thought I’d drop her a line on MySpace and see if anything happened.

“Maria! It’s been a long time and I hope you’re doing great. I wanted to let you know I’m going to be in town overnight next Monday, and I would love to get together for a drink. I know you’re busy. If you can make it work, let me know.”

To my surprise, she replied within an hour or two.

“Yes! I’ll be here! That would be so fun! Let me know if there’s anything special you want to do while you’re in the city. Just to be clear, if you need somewhere to stay, I can offer you my couch, but that is all I can offer you. I’m seeing someone. Is that OK? – M”

That was a disappointment. I was still pretty naive, and didn’t realize that it was a good sign she was even acknowledging that she’d share her bed if she was single. I figured nothing would happen, but it’d be fun to try anyway. With two sure things – a nymphomaniac college freshman and a lonely MILF with an impressive set of C cups – in the pipeline, this trip is going to be good for me no matter what happened with Maria.

Saturday rolls around, and I board the Spirit of New Orleans for the overnight ride to Chicago. When I arrived, I let HotOrNot Girl know I was on my way, and hopped on the Metra to Des Plaines. HotOrNot Girl was there waiting to pick me up and drive me to her house. We’d never seen each others’ houses, and her parents were away for the weekend. It didn’t take long for a glass of iced tea and a tour of the house to turn into playtime.

The final stop was her father’s den, and when I sat in the office chair, she realized I was so hard I was bulging out of my jeans and started laughing. I laughed, too, and started unbuckling my belt.

“Not here. That’s so fucked up.”

“Yeah, it is.” I started stroking it for her and smiled. “Get down on your knees and do something fucked up for me.”

She swallowed her pride and went to work, alternating between licking and sucking my balls and me shoving her head down on my shaft until she struggled. I couldn’t believe she was so enthusiastic. It was July, I hadn’t taken a shower since the morning before, and I knew my balls must smell like somebody spilled a vial of musk in an old gym locker, but she seemed convinced she could lather them up and rinse them off with her tongue.

When I blew my load in her throat, I hadn’t jerked off since Friday morning, and I didn’t warn her, because she never wanted to be warned. It was too much, though. She choked, and it splashed all over the edge of her dad’s chair. She was horrified.

Together, we cleaned it up, then went to hang out in her room, which had turned out to be the unfinished basement. We’re talking bare foundation bricks and a creaky old bed with no air conditioning. She’d told me her stepmother was a bitch who’d pushed her aside, but I didn’t know she meant she’d made her sleep in a dungeon through high school. Holy shit, no wonder this girl liked what she liked.

Either way, we took some cute pictures together with her webcam, then got to making out and undressing each other. Soon, I was going down on her and getting hard again, and told her I wanted her on top because we’d never gotten around to trying it. The joke was that I knew she was going to have to work like a slave to get me off, because I’d just cum, but she hadn’t realized that yet.

“I’m not good at that.”

“What do you mean?”

“I just suck at it.”

“Well, you’re going to get your first round of riding lessons then, and you can take something new back to school. I’ll train you, right now. You have any condoms down here?”

“Shit, no. I took them to school.”

“That’s OK. I think I’ve got a three-pack in my bag, in the front pocket. Go get one, and turn the webcam on before you get back and point it at the bed. I want you to have something to watch when I’m gone.”

“Are you serious?”

“Did I sound like I was kidding? Go do exactly what I said, and don’t question it or I’m going to spank you. You want to tell your parents why you can’t sit down for dinner tonight?”

She giggled and hurried to get up, saying something about her ‘riding lessons’. I knew I wasn’t going to cum again easily, but I didn’t expect it to turn into what it did.

At first, she was excited and giddy, but for the next forty minutes, she worked herself breathless bouncing up and down on my cock, and would not stop, even when I hinted that she could take a break, humiliated at the idea that she might be bad at riding cock. It had to be over 80 degrees in that room, and she was drenched, shining with sweat and dripping all over me while she moaned and cried out. All she wanted was validation.

“PLEASE, JUST CUM FOR ME. I CAN’T CUM. MY LEGS ARE SO TIRED. JUST CUM. IT’LL MAKE ME CUM.”

That was something I just couldn’t do. I was close, constantly on the edge of emptying my balls, but I just couldn’t get there, and neither could she. She was right on the edge of an orgasm she couldn’t quite reach, and her screaming and pounding away, mixed with the sound of the bed rattling and creaking and her wet pussy was so incredible I had to laugh at how insane it all was.

“DON’T FUCKING LAUGH AT ME, ASSHOLE. JESUS CHRIST.”

Oh, now we’re getting into what she wants.

“I’M LAUGHING BECAUSE YOU’RE SUCH A LAZY SLUT. YOU DON’T EVEN DESERVE TO CUM. PUMP YOUR LITTLE ASS LIKE YOU’RE TRYING.”

I spanked her hard, so hard that her bottom lip started quivering. Whatever noise she made when I said that, it wasn’t something that can be spelled. Sweat was running down her long, tangled blond hair as her head whipped around, and some of it splashed on my stomach. I was starting to think she was either going to black out in the heat or the crappy, creaking bed was going to collapse.

“ARE YOU GOING TO CRY? DON’T BE SUCH A PUSSY. GO TO THE GYM AND TOUGHEN UP YOUR ASS IF YOU WANT TO GET BETTER AT WHORING. HAVEN’T YOU EVER PERFORMED ON CAMERA BEFORE?”

“OH FUCK, I FORGOT THE- NO. YES. A GUY AT SCHOOL AND WE TOOK PIC- FUCK. NOT LIKE THIS.”

“DID HE CUM?”

“YES!”

“THEN WHAT’S YOUR FUCKING PROBLEM MAKING ME CUM?”

“I DON’T KNOW. FUCK. I DON’T KNOW. OH, SHIT, I HATE YOU.”

Then she surprised me and did something she’d never done before: she spit at me, in the face. Without thinking, I spit back at her, then yanked her hair back and put one hand on her throat. She didn’t miss a beat.

“YOU PIECE OF SHIT. I WANT TO CUM, OH MY GOD, PLEASE HELP ME CUM!”

Then, suddenly, she looked like she realized something. There was a low I-beam running right over the cot. She sat straight up, reached up and put her hands on either side of it to help hold herself up, and could finally stop worrying about her balancing her own weight. She started bouncing her ass frantically, jackrabbit-style and, somehow, miraculously, both practically choking on our own voices, we came together, angrily. She sounded possessed.

Then it was over, and she put her head down and just started bawling her eyes out. I caught my breath and tried not to laugh while I smoothed her sopping wet hair and she kissed my chest.

“That was OK. You’ll get better at this eventually. We should probably turn off the camera, though.”

“Shut up. I can’t move. Can you reach it?”

She wasn’t kidding. Her legs were useless, I had to grab her by her hips and lift her off my dick, then stood up to shut off the camera.

Then I saw the clock on her computer. “Baby, is this clock right?”

“Yeah, why?”

“I’m sorry. I need to get going if I’m going to get some food before I leave, like, now.”

She wrapped her arms around my hips from the bed and pulled me back. “Nooooo. No! Stay with me. Forget whatever you’re doing.”

“Aww, your parents are going to be home anyway. Can you drive me back to Des Plaines or no?”

I felt bad. I did care about her, and I’d read about BDSM aftercare in the past and figured this was along the same lines. She was a wreck, needed some affection, and running out on her was the wrong thing to do. I ended up taking a chance on being late and having pizza with her across the street from the station, a place called Leona’s. It doesn’t exist anymore, which is shame, because it was solid for the price.

We sat on the same side of the booth and she cuddled me relentlessly the whole time, kissing my shoulder and making the waitress smirk. By the end of the meal she was feeling better. She cried a little as we kissed at the station, and that was it. Back on the Metra to make the Lake Shore Limited to New York. Only once I got on board did I find out that my ticket class wasn’t eligible to use the showers.

Fuck. OK.

Source: reddit.com/r/gonewildstories/comments/adafup/train_trip_part_1_one_day_in_chicago_with_a