Train Trip, Part 2: One Night in New York with Finance Exec [MF]

Not sure if Part 3 of this will get written or not, since that encounter is hard to make a good story out of, but wanted to get this one up:

After making it out of Chicago on time ([https://www.reddit.com/r/gonewildstories/comments/adhz2d/train_trip_part_1_one_day_in_chicago_with/](https://www.reddit.com/r/gonewildstories/comments/adhz2d/train_trip_part_1_one_day_in_chicago_with/)) my trip was feeling pretty worthwhile so far. I spent the evening making small talk with a Russian woman who worked in “massage”, then fell asleep for the night before hanging out in the lounge car the next morning. We were running hours late. I was told that at least in those days, every freight carrier had priority and we had to stop to let each one pass, so what should have been an early afternoon arrival with plenty of free time turned into sunset.

Still, I made it. On the way out of Penn Station to Maria’s place in Chelsea, I decided to stop for a bottle of wine as a gift. I wasn’t sure if that was the right move or not, but it’d been a year since we’d really talked, and it felt important to make an impression on an accomplished older woman. I texted her to let her know I was on my way, then rang the buzzer when I got there.

No answer. A woman walked up beside me, a fit blond spinner in a cute sundress walking a pretty big dog, and started to open the door. Really nice legs. It took a second for my mind to click.

“Wait, Maria?”

“Oh! Hi! I didn’t know you were here yet! I’ll bet you texted, but my phone died.”

We hugged and exchanged pleasantries, then I needed to hurry to get washed up. I wasn’t going to say so, but it was July, it’d been two and a half days since I’d taken a shower, with two nights on trains and a day spent being ridden by the sweat-soaked HotOrNot Girl.

Once I washed up, I got dressed and started looking around. Maria’s apartment was nice. Small, but sizable for Manhattan. I remembered when she was looking for the place after she changed jobs, somewhere that would take her dog. I threw on a dark green button down I’d bought for the trip and stepped out.

“Maria, I can’t decide if I like this. What do you think?”

Being over a foot taller than she was, she had to reach up to straighten the collar, then stepped back to look. “It fits your shoulders just right, I like it.”

She was acting very familiar for someone I’d just met in person for the first time, and I liked the way this was going. I gave her the bottle of wine and we talked about plans for the evening. She wanted to keep the meal simple, a pizza place she loved, then had somewhere in mind: “I thought about taking you to a club, but you seem more like a bar guy.”

She was right. We realized it was starting to rain, so rather than walking to the subway station, we jumped in a taxi. The conversation was so easy and intimate at dinner, and at some point, when we started talking about our families and where we got our features, she subtly squeezed her cleavage together with her arms for me.

“I don’t know where I got these from, though. Not my mom.”

Afterwards, the rain had stopped, and she took me for a walk around Washington Square, and showed me some spots that used to be significant to her in college. We stopped at a bar with an outdoor table and chatted away over drinks about life in the city and what we thought the future looked like. Surprisingly, she acted pretty down on the new boyfriend. He supposedly didn’t pay much attention to her and drank too much, but she was letting it play out.

“I don’t think it’s too much to ask someone to check in once a day if you’re in a committed relationship, is it?”

Then came the taxi ride home. She was a little drunk, and I took the initiative to brush her hair away from her face, then run a finger down her neck. She sighed. “That feels so good.”

We leaned in for a kiss, then lost control of it and made out until we got back to her place. It was looking like I wouldn’t be condemned to the guest couch after all, but we tried to dial it back a little. She wanted to watch a movie, so I opened the bottle of wine I’d brought while she put it on. While she was getting it going, she saw a book I’d been reading in the outside pocket of my backpack. “Oh my God, I love that book! Have you finished it yet? It’s one of my favorites.”

I’ll never remember what the movie was. Within a minute or two, I had her dress hiked up and two fingers inside her while we kissed deeply, tongues mingling. Her pussy was the most neatly groomed I’d ever seen, and I kissed my way down her stomach, pulling her panties off.

“You don’t have to do that.”

“No, I don’t. I want to.”

Finding her g-spot was no trouble, and she came easily and repeatedly. She grabbed at my hair, begging and pleading while I furiously licked her clit and fingered her. A third finger just made her cry out incoherently. When I led her into the bedroom, she already seemed exhausted and shaky.

“Are you OK?”

“Just, really powerful orgasms. Look, I need to do something. Can we stop for a few minutes?”

She stepped into the other room, and it was obvious she was trying to call her boyfriend. No answer. I heard her leave a curt message that she was just trying to say goodnight, then she came back into the room and stood me up before she sat on the bed, unbuckling my pants and taking out my hard cock. She weighed it in her hand before looking up at me smiling. “So did I ever get around to telling you I don’t have a gag reflex?”

She proved her point, sliding it down her throat in two or three gulps, to the balls, before bobbing her head on it. I’d never had that before, and we ended up doing 69 with her on top, her quivering and whimpering around my cock while I fingered her g-spot. She was so worn down from climaxing that she had to sink down between my legs and focus on my balls for a while, and I realized we’d lost all track of time. It was 10:45, we’d been carrying on like this for two hours.

I wanted the rest of her. I pulled her up to kiss me, and as we made out I reached down and started rubbing her clit again. She was too sensitive, quivering and moaning into my mouth just from being gently touched, and kissing and biting my neck and ears like an animal. I reciprocated, and her reactions were so intense I didn’t even think about going easy on her.

“Look, there’s a condom in my bag, why don’t I go get one and…”

“I… No. No. I can’t do that. This has gone way too far already and I love it, but I told you.”

Her mouth was saying ‘no’, but I could feel her pussy lips rubbing on the head of my cock, extremely hot and wet. I wasn’t going to push it, but her mind and body were clearly pulling in two different directions. In the dim light, I could see was looking out the window, like she was trying to decide.

“You don’t have any diseases, right?”

“No. You?”

“No. He’s such an asshole anyway. OK, can we just…”

She started sliding herself down onto my shaft, and while it was a chore for her to make it fit, soon I was all the way inside without a condom. It was a first for me, and she was easily the tightest woman I’d had. Unlike HotOrNot Girl, she knew what she was doing riding a dick, and had a rhythm down. Feeling her pussy strangling my shaft and watching her writhe on it like a bellydancer was so much stimulation that I had to close my eyes and stop thinking about it or I was going to have to cum. After a few minutes, even that wasn’t enough.

Maybe changing positions would buy me some time. I put my hands on her hips and stopped her, then guided her onto her back. I stood at the edge of the bed and put her feet up on my shoulders. I’d never tried it before, and her legs barely reached, but it was a great position. I could run my hands down her legs and over her ass, grabbing her by the thighs to control the pace. That was a turn-on, but it worked just like I hoped, giving me some more time to enjoy her.

In fact, now I was grinding against her clit, and could easily hit bottom with every thrust. Knowing her pussy was completely stretched and filled with my bare cock made me feel powerful, and it changed the way she was feeling it, too. She looked lost in it, mouth open, hands alternately teasing her nipples, rubbing her stomach, or limp over her head.

Best of all, I was in no hurry. I could watch the clock and knew we kept at it that way for a good fifteen minutes before I even needed to ask.

“Do you want me to finish inside you or on your body?”

She answered instantly. “Cum inside me!”

Saying it made her climax, and that made me ready, too. I changed my stance and put my hands on either side of her hips, and started fucking her with my deepest strokes. She reached down and grabbed for my hands, but then in the final few seconds, her head cleared.

“Wait, you can’t, I got off birth contr-”

…and just like that, with my cock buried inside her, I sprayed my sticky load directly onto her cervix. Realizing what was happening made her orgasm again, and she squeezed my hands as she yelped, grinding her hips against mine. We were silent after that, but I kept thrusting for a minute or two, breathing heavily, until I was too soft to go on. When I pulled out, I could see my cum forming a long strand from the head of my cock leading inside her, glittering in the dim light.

I rubbed myself against her a little to clean off, then finally, she reached over and finished the rest of her wine in one gulp. Wetting her mouth helped her catch her breath enough to speak: “Oh God, what you must think of me.”

I was just savvy enough to know ‘I swear, I never do anything like this’ when I heard it, so I just got on top of her and kissed her deeply for a few minutes, my wet cock still dripping cum on her legs.

When she went to wash herself off, she finally got a look in the mirror. “Oh, oh no, my neck. I have bruises.”

“Shit, I got carried away. Those are probably going to be bad, sorry.”

“It’s… It’s fine, I have some makeup that I think will work. Wow.”

We slept together there in the bed, but without cuddling. In the morning, she woke up first, and nudged me awake. It was still dark. She was wearing some kind of frilly pink nightie, and had a question: “What would you want on a bagel?”

Turned out she was going for a morning run and would come back with takeout. For a woman who’d just ruthlessly cuckolded her new boyfriend in cold blood without a condom, I thought that was sweet. I went back to sleep, then finally woke up to daylight and the sound of her dog running to the door when she came home.

Now she was drenched in sweat, wearing a blue sports bra and yoga pants, and carrying our breakfast. We sat there on the foot of her bed and chatted, and my inevitable morning wood hanging out in the open made her giggle and grab it. When we’d finished eating we ended up making out again, before she went down on me, licking my shaft in long strokes.

“My cock must smell like you.”

“I think your whole body smells a little like me right now.”

“Do you taste yourself on me?”

“I love tasting myself. If we do ever get some more time together, there’s a lot of fun stuff we can try.”

Yeah, I was definitely cumming inside her again. I didn’t have much time left, but she didn’t need to know that right now.

I helped her get her sports bra off, and before long we were at it again, with her pressed face down on the bed laughing, my cock inside her while I held her arms down at either side. Morning sessions never go fast, and when I finally came, I kissed her on the back of the neck, patted her ass, and told her I needed to get my shower.

When I got out and got dressed, I broke the news: “I’ve got to get going to catch the train.”

“…oh. OK. I thought we could…”

“I’m sorry, I didn’t realize it was already this late.”

She was clearly startled that I was bailing on her, but gracious about it. We kissed and I went out the door, walked up to Penn Station in a great mood, and made my train for New England.

I pulled my phone out at Albany and found that I had two messages. One was from HotOrNot Girl:

“My dad went into the den and sat in that chair, and I got so wet I had to go downstairs and rub myself raw to that stupid video. I hate you so much.”

The other was from Maria:

“Look, I’m not angry, but you had a condom in your bag and had to rush out the door this morning. I don’t want to be used. Just tell me the truth if you’re going to meet another woman.”

Huh. She actually cares where I’m going?

“That’s not something you have to worry about. I wanted that, but didn’t plan on it. I always have condoms, and I felt like we had electricity between us. I just lost track of the time. I hope I didn’t put you in a bad position.”

“I have no regrets about any of that.”

Source: reddit.com/r/gonewildstories/comments/aj2bp1/train_trip_part_2_one_night_in_new_york_with