Train Trip, Part 1: One Day in Chicago with Suburban HotOrNot Sub [MF]

When this 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, at a job with 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.

I was still hooking up with my high school sweetheart, a year older, from time to time, and occasionally meeting a blond from the Chicago suburbs I’d found on HotOrNot, a year younger, who was happy to drive to meet me so we could both be away from our parents and she could get treated the way she liked, which was mostly getting fucked like I hated her. I’d been the first guy she hooked up with after she dumped the high school boyfriend who took her virginity, and we had a thing going on where we talked a little almost every day while we went about our separate lives, but connected when we could to experiment.

More generally, though, I was getting bored. I hadn’t gone back to school yet and just didn’t have a lot going on. 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 needed a plan to step away and have some fun. I’d been talking to a bunch of different women online and decided to string a few together to break up my routine.

I’d never seen New England, so I arranged to crash with a cute divorced single mom I’d been flirting with online, maybe 28 years old. She was excited to spend the Fourth of July together and wanted me to barbecue for her. After looking into it, I ended up deciding to take Amtrak because it was a lot cheaper than flying at that time, and I’d have an chance to stop in Chicago and see HotOrNot Girl again before she went back to college.

Then there was J. She was 33 now, working in finance in Manhattan. We had connected 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 cute and fit in her pictures. I never really understood why she spent time on me, but talking to her had been eye-opening about the world away from home.

One day, suddenly, she got a new, more demanding job in mergers and acquisitions with a lot of travel 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 what happened.

“J! 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? – J”

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.

Saturday rolled around, and I boarded 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 bring me to her house.

She looked great, happier than the last time I saw her and wearing some tight jeans. College was clearly great for her. We’d never seen each others’ homes, we’d always just split the cost of sketchy motel rooms, and her parents were away for the weekend, so this was new. It didn’t take long for a glass of iced tea and a tour of the house where she grew up to turn into playtime.

The final stop was her father’s den, and when I sat in the fabric 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.

“What? 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.

“Hey, you think your stepmom ever does this here?”

“Mmmf!” She popped my sack out of her mouth laughing. “Come on, that’s not even funny.”

When I blew my load in her throat, I hadn’t gotten off since Friday morning, and I didn’t warn her, because she never wanted to be warned. This one was too much, too fast for her to swallow, though, and she ended up coughing and spraying a lot of it over the edge of her dad’s chair. Whoops.

I helped her clean it up as best we could, then went to hang out in her room, which turned out to be the unfinished basement. We’re talking bare foundation bricks and a frail 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. Whatever. She’d made it into a cool space.

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 hard again, and told her I wanted her on top because we’d never gotten around to trying it.

“I’m not good at that.”

“What do you mean?”

“I just suck at it. I feel really clumsy.”

“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 whip you until you have to tell your parents why you can’t sit down for dinner tonight.”

She giggled and hurried to get up. I knew I wasn’t going to cum again easily, and that was the point. I figured it’d be a fun game to make her work for it, but I didn’t expect it to turn into what it did.

At first, she was excited and giddy, but for the next thirty 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.

“PLEASE, JUST CUM FOR ME. I CAN’T CUM. MY LEGS ARE SO TIRED. JUST 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 there with me, frustrated that she couldn’t quite get there no matter how hard she worked. Her furious efforts, combined with her screaming and the creaking and rattling of her old metal bed, felt so incredible I had to laugh at how insane it all was.

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

Oh, a little anger. Now she was warmed up.

“I’M LAUGHING BECAUSE YOU’RE SUCH A LAZY SLUT. YOU DON’T EVEN DESERVE TO GET OFF IF THIS IS ALL YOU’VE GOT. WORK.”

I spanked her on one ass cheek firmly, maybe too firmly, enough 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 going to black out in the heat.

“FUCK YOU.”

“ARE YOU GOING TO CRY? 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.”

“BE A BETTER WHORE OR JUST GIVE UP LIKE A LAZY BITCH.”

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, which just turned her on even more.

“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, we finally came together.

As her pussy clamped down on me, her eyes rolled back in her head and she let out a long, desperate sobbing/choking noise I’d never heard. Then it was over, and she plopped her head down on my chest 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 neck and shoulders.

“You did OK. You’re getting the hang of it. We should probably turn off the camera.”

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

She wasn’t kidding. I had to grab her by her hips and lift her off my dick, then shut off the camera.

Then I saw the clock on her computer. “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. I’m already going to have to shower on the train tonight.”

“Nooooo. No! Stay with me. Forget the train.”

“Your parents are going to be home in a couple hours anyway.”

“We’ll get a room. I’ll pay for it.”

I felt bad. She was wrecked and I didn’t want to run out when she was obviously needing affection, so I ended up taking a chance on being late.

“Awww, come on. If you can still drive me back to Des Plaines, we’ll get something to eat together. I’ll buy.”

She brushed her hair out as best as she could and we had pizza across the street from the station, a place called Leona’s. It doesn’t exist anymore, which is sad, because it turned out to be amazing for the price.

We sat on the same side of the booth as she cuddled and kissed me relentlessly, making the waitress smirk every time she came by. Then she cried a little as we parted 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 fare class wasn’t eligible to use the showers.

Damn. OK.

Source: reddit.com/r/gonewildstories/comments/adhz2d/train_trip_part_1_one_day_in_chicago_with