(For less backstory skip to THE WEEKEND below)
Around 2017, I was in a stretch of traveling a lot for work, I’d been talking at conferences & universities.
My most recent relationship had sort of fizzled out, in part because I was traveling so much. When I got invited to Chicago I was glad because my friend and her husband had just moved there and it’d be nice to see some friends. I decided I’d forgo the hotel room & stay in their new guest room. (I’d come to kick myself for that decision.)
This trip was to talk to about 100 graduate students. I arrived in the morning and a student, Emma met me and gave me a quick tour. She also mentioned that there’d been a scheduling conflict and only people in her cohort would be joining, not the entire program. That meant I’d be talking to ~20 instead of ~100. I didn’t mind, it was honestly a bit of a relief, I could be much more casual & interact more with the group.
Since there were so few of us, it was easy to gel with the group. I was only a year or two older than most of the students, and we all shared a niche interest in our field, so after my talk was over I wound up hanging out with a group of about eight of them. Emma was of course among them, I’d noticed during the discussion that she seemed to hang on every word I said, a couple of times I caught her eyes while we were out, but we didn’t get a chance to talk alone.
Around midnight I decided to call it a night, and grab an Uber back to my friend’s house.
When I pulled out my phone I saw that I had a text from Emma:
“Wait for me? Maybe I could join you in your hotel for another drink?”
*I realized there were two more from earlier*
~10pm: “Hi”
~11pm: “I’m just going to say it, I want to spend the night with you. ❤️🤤”
I texted back from my Uber, “Sorry, just saw your texts. I’m staying with friends”
She texted back: “😞, are you in town tmw night?”
I wasn’t, and we went on flirting for the next week or so until it sort of fizzled out, we’d send a text here or there, but with her in Chicago & me a few hundred miles away.
That is until about a week before Memorial Day when I got a text from Emma, the first in about a week.
Emma: So do you have any plans for next weekend?
Me: Nothing major, a friend’s belated housewarming.
Emma: Need a +1? 😉
Me: You’re in town?
Emma: Yep! All weekend. Show me around?
We wound up deciding I’d meet her at the train station. I was excited to see her again.
THE WEEKEND
Her train arrived right on time. I saw her immediately when she got off the train, but she hadn’t noticed me yet in the crowd. It dawned on me that I hadn’t really looked at her sexually before given the context of our last meeting, but I was now taking her in in a new light. I noticed she’d curled her medium-length blonde hair since I’d last seen her. She had a thin frame with average sized breasts, but a surprisingly round ass. She turned and saw me and her light blue eyes sparkled as she smiled.
I grabbed one of her bags and asked if she wanted to drop her things off at her hotel. She said she was starving and wanted to eat first, so I guided us to a nice spot not far away. She was surprisingly quiet during our meal, enough so I started to wonder if I’d misread the situation entirely somehow.
She hadn’t really eaten much and seemed distracted, when I came back it looked like she was stressed about something on her phone. I decided to ask if everything was OK.
Emma: I uh, well, I need to find a hotel.
Me: What happened with yours?
Emma: I never booked one, I thought I might find a place to stay once I was here.
*(I’ve realized a recurring theme in my stories is that I’m the last one to know what’s about to go down. Cut me some slack on this one though, I knew we were going to hook up, but she never once mentioned staying with me, and implied she’d be in town.)*
After a beat, I realized what she’d meant. I’d almost fumbled this, but after a bit of reassurance that it was definitely OK, I just hadn’t wanted to assume, we decided to head back to my place.
She looked relieved, but was still somewhat quiet. We hopped in a car to ride back to my place with her bags. I reached over & held her hand and I could see her body release its tension.
The second we got in my door we were all over one another. I usually savor getting to know a new partner, but for some reason, probably the pent up frustration at almost being denied again, I was inside of her in my kitchen. We’d flirted via text enough that I knew a little bit about what she liked and quickly took a fistful of her curly hair as I told her how filthy of a weekend we were going to have. She came quickly, her orgasm caught me by surprise and before long I was pulling out to cum all over her stomach. She had this cute birthmark right near her belly button and I remember vividly how my cum seemed to erase it from her pale skin.
We didn’t leave the apartment for the next 36 hours. We’d both been in a bit of a dry spell after LTRs, and that combined with weeks and weeks of tension led to a perfect storm. She came clean that she’d planned the trip in her head as soon as I’d left the bar weeks earlier. With a three day weekend she figured she’d have an excuse to visit and was pretty sure it’d end up like it was.
We both knew this was going to be a brief fling, and we both opened up about our secret fantasies and kinks. Neither of us had ever given or received a rimjob and by the end of the weekend she seemed addicted to them and I think we were both left with a new lifetime kink. Watching her tongue my ass while she jerked me off put me over the edge more than once on that trip.
I also helped her fulfill a voyeur fantasy of hers the second night. We’d finally made it out of the house and were getting drinks in a dive bar across from my condo. She had mentioned during one of our post-coital conversations that she had always wanted to fool around in public. When she returned from the bar with two new drinks I gestured to my side of the table and told her to sit next to me instead of across so we could hear better. As soon as she sat down I put my hand on her thigh in a way that had my index finger just inside the hem of her shorts. She looked at me with wide eyes and gave me the most “holy shit, do it” look I’d ever received.
Over the next few minutes, which I made feel like hours to her, I worked two fingers between the jean shorts & panties, which were already noticeably damp. I kept going until she leaned over and stifled a moan into my shoulder. I realized we were probably about five minutes from getting kicked out, and this was one of my favorite spots, so we had to take it back to my place. I wound up making her cum multiple times with my hands, which is a favorite of mine. (The control, the asymmetry of making her cum while I’m fully dressed.)
It was a great weekend, but we never managed to sync up again as she got busy with school and we both started dating people closer to home. We’ve drifted apart but I now spend about half my year in Chicago and if she hadn’t recently gotten married I’d have sent her a text letting her know.
Source: reddit.com/r/gonewildstories/comments/12ou9r3/mf_a_nearly_missed_encounter_leads_to_a_3day
so basically i should let a girl give me a rimjob