I wrote my first entry a month or so ago about an encounter I had with one of my good friends Jason a few years back that still keeps me up at night. He’s also the one who introduced me to this subreddit so I knew he would eventually read it.
We talk pretty often about everything from the daily mundane to opening up about our kinks and fantasies. Since reading the post I made about him here, our messages to each other have gotten less platonic and increasingly hotter. He even wrote a post about me in here earlier this week so I thought it might be fun to tell you all a bit more about something a little more….recent. This involves some solo play, some of which he already knows about and some he will be learning about for the first time with all of you.
A few weeks back I had to travel out of state for work. Jason and I haven’t seen each other in person in years since we don’t live in the same area anymore, so we rely on messages as our main way of communicating with the occasional FaceTime or phone call. Since I would be getting a hotel room to myself, I wanted to take full advantage. I let him know I was going to be traveling and asked if there was anything specific I should pack. He told me to pack some lingerie and some toys. I wasn’t checking a bag so the idea of having a carry on full of sex toys and lube made me wet. If he would have been on that plane with me, we would have been in trouble.
I had a super early flight that got cancelled last minute. The new flight the airline was putting me on would arrive after my work event so I left for the airport at 5am to try to get on whatever flight I could. I was running around the airport flustered trying to figure out how to get to my destination in time. I got a last-minute flight and had to hurry through TSA pre-check so I wouldn’t miss boarding.
I completely forgot about the mini sex-store in my suitcase as it went through security. A TSA agent pulled my bag and pulled me aside so he could search the pocket of my bag that held all my toys. I turned beet red and frantically told him without thinking “It’s just a vibrator. I’m going to surprise my boyfriend”.
The agent took a quick peek inside the bag, smiled at me and told me to enjoy my trip.
Something about getting caught with sex toys at the airport and the chaos of getting a flight that morning made me hot and bothered and in need of some de-stressing. As soon as I got through security, I made my way to one of the bathrooms by my gate, locked myself in a stall and started playing with myself until I had to bite down on my jacket arm to keep from moaning.
When I was done, I cleaned myself up, changed into a fresh thong so I wouldn’t smell like cum, and immediately messaged Jason to tell him about getting caught with my vibrator. I figured he would read it when he woke up for work.
I got to my destination and checked into my hotel. I was supposed to meet with a few of my teammates who report to me to take them out to a team mixer and meet some of our other coworkers for the first time in person. I went to drop off my bags in my room before I met them in theirs and while unpacking my outfit for the mixer that night, I spotted the toys I had brought.
I texted one of my coworkers that I was tired from my flight and would need a quick 20-minute nap before I would be ready but instead of sleeping, I decided to have a little bit of fun. One of the toys I brought is a panty vibe that sits right on your clit. If you read my other story, you know one of the best positions for me to get off on is when I’m riding on top.
I was horny as hell and needed a good, vocal release since I had to be discreet and quiet at the airport earlier, so to make it extra enjoyable, I lubed up the smaller anal plug Jason had told me to pack and put it in my ass as I positioned the panty vibe inside my thong. I had a room with a king size bed and 7434379 pillows so I grabbed two of them and positioned them between my legs as I turned my vibrator on. I closed my eyes and imagined I was bouncing and grinding on Jason’s cock as I fucked myself against the hotel pillows. I positioned them just right where my vibrator was pulsing hard against my clit and as my ass tightened around my plug I could feel myself reaching an intense climax.
I moaned as I collapsed against the pillows and felt myself dripping down my leg. I had to get ready to go to the mixer but thought it might be fun to keep my plug in as a little secret. I changed into a dress with sheer tights and boots, used my cum to re-lubricate my anal plug, and went downstairs to meet up with my coworkers.
All I could think about the entire night I was out was coming back to the hotel room and fucking myself on video for Jason. One of my coworkers is newly single and kept trying to convince me to stay at his place since we had all been drinking so I would stay out later, but I just wanted J. I got back to the hotel and showered and took my plug out. I changed into the black teddy lingerie I had packed and decided to use my larger plug that Jason had picked out online for me (a metal one with a cute red heart gem) I got my phone out and recorded myself slipping the plug inside my ass, making a small gasping noise as I felt the cold metal.
Jason and I were great about telling each other what we wanted to do to each other over text, but on a recent FaceTime, I had been a little shy actually saying it out loud so I decided to take another video for him showing him my vibrator and telling him what I was going to do to myself. I rubbed my clit with the vibrator before inserting it inside me and using my thumb to play with my clit.
I positioned my body so I could feel more of my plug inside me and lowered my phone camera so Jason would get a front row seat to my pussy right as I was close to making myself cum. I moaned his name loudly as I orgasmed and collapsed on the bed. I sent him the videos knowing he would wake up to them and fell asleep wishing he had flown out for the night.
I woke up the next morning to messages from him about what seeing those videos did to him. I had a very early flight to catch but knowing I made him hard made me horny all over again. I had packed a dildo with a suction cup and decided to let my exhibitionist side have some fun before I had to catch an Uber to the airport.
My room was 11 stories up in a busy downtown area so I opened the curtains just enough to stick the suction cup to the window, undressed, and fucked myself from behind. Anyone on the street who looked up would have seen my ass pressed against the glass as I took all 7 inches into my pussy. After I fucked myself, I sent him a message to let him know how I had spent my morning.
He immediately messaged back about how badly he wanted to be in that room with me and that if he had, he would have flipped me around, bent me over, and fucked me with my tits against the glass for the whole city to see.
I was running late for my flight so I quickly packed up all my toys but didn’t have time to wash the sex smell off of me. The entire drive to the airport I was looking up flights to his area, playing with the idea of pulling the trigger and going out there one of these days to act on these fantasies with him in person. I saved the videos I had sent him and have watched them a few times since I’ve been back.
What do you think Reddit/Jason, should I go visit?
Source: reddit.com/r/gonewildstories/comments/txf84g/our_fm_long_distance_sexcapades_lead_to_me_using