Encounter #69.2: Air Force

App: Tinder

Name: Colton*

Date Location: Panera Bread

Location Review:  N/A

Date Duration: 5 hours

What Happened:

Since our first date, Colton and I talked nonstop. Also, things got a little saucier than they were before. Like we were writing each other erotica and having the “What do you like?” conversation. Despite us both being truly disgusting, it never crossed into a creepy or uncomfortable territory. Even though he said filthy shit, it was still respectful if that makes any sense at all.

The plan was I’d meet him on base and then we’d go and get brunch. Gotta be honest, the Air Force base in Massachusetts looks like a 1970s community college. I parked at the house and somehow I ended up inside. Within about 30 seconds we were making out, he picked me up, and carried me to the couch. Hot.

I was a bit hung over so even though the work he was putting down felt great, I needed to eat something. I pumped the brakes and we headed out to brunch.

Now I was told we were getting brunch in Boston. We ended up in Burlington, MA. Not bad, but it’s not Boston. A bit different. The restaurant he wanted to go to was nice but they didn’t do reservations and there was a 40 minute wait. Then we tried 2 more places and they were both closed. This left us with Panera Bread.

He insisted on paying for everything and made a point to be the one to go up and get the food and all that. Any opportunity he had he’d touch me in some way either by holding my hand or having some part of him touch me which I really liked.

Brunch was fine. I was hurting and he had a cross fit competition the day before so we were both a bit dead (more on that later). But once we got some food in us we started to get back to our normal baseline.

On the way home, he gave me a tour of the base and mentioned again that he was looking to leave it. After seeing everything, I didn’t blame him. But, it made it clear that this was probably just going to be a casual thing. It wasn’t ideal but, I also wasn’t opposed to having a little summer fling situation.

We got back to his house and as expected, things started happening upon arrival. He got my clothes off and went to work pretty quickly and it just wasn’t it. I won’t say it was bad but, it wasn’t my vibe. The moves he whipped out were something I’ve only seen in porn. He more or less spread my cooch apart and went in like it was a watermelon. Sir, there is only one spot I need you to work on and you’re everywhere but there. On top of that he was playing with my tits but not in a pleasurable way. It felt like he was trying to pull them off my body. Just no chill. Warm up the car a bit before getting in there.

I asked if I could reciprocate so I made my way to blow him. At this point in time he was completely soft. Okay, he’s the type of person who needs to be actively touched to get hard. That’s fine. I got to work and after about a minute he pulled my head up. I kept jacking him off and 30 seconds later I felt it. My hand was suddenly drenched and was incredibly warm.

I didn’t want him to feel weird or be embarrassed so I didn’t look down. I just kept making out with him and waited for him to say something. He sighed, apologized, and blamed it on being dead from his competition the day before. I mean it happens. I wasn’t going to make it weird. I get it. He wasn’t feeling 100, I was a new person, whatever. I was going to be there a few more hours anyways.

We spent the next few hours cuddled up naked on the couch making out. The conversation just wasn’t there though. I realized that since I got there that morning, he asked me maybe 3 questions and it was a lot of me carrying the team.

Eventually things heated back up again and got better on my end. Still not as good as promised but, it wasn’t horrible. I asked again if I could work on him. This time he lasted 2 minutes. I know my strengths and I know I’m good. I’m not that good though. This was a day for personal records.

We cuddled a little bit longer and then it was time for me to head out. He had to watch his sergeant’s kids and I was just tapped out. He walked me to my car but made no mention of future plans. We kissed and I went on my way. When I got home I sent the “Thank you for having me blah blah blah” text and to my surprise he responded and said he’d want to do it again. We texted here and there in the days after but it just wasn’t the same. He wasn’t nearly as talkative and it just felt forced. The only times he really asked me anything or seemed interested were when things got a little sexy.

I never answered his last text of “hahaha”, and that was the end of that.

Encounter #54.2: Coast Guard

App: Bumble

Name: Jesse*

Date Location: His Place

Location Review:  N/A

Date Duration: 2 hours

What Happened:

I was a bit disappointed when I didn’t hear back from Jesse. It dug up a lot of weird shit I had been pushing aside and even though I disagreed, he wasn’t entirely wrong that I had a wall up.

I went along with my weekend and everything was going to plan until that Saturday night. My friend and I were drinking on my couch and I saw a text from him come in asking what I was up to. I left it on read. He needed to sweat.

About an hour later he called. I picked up and it came out why he hadn’t talked to me all week. He was being deployed in less than 48 hours. Fuck.

The reason his medical clearance was so crazy was because they were immediately sending him out on a mission. He tried to apply for leave to give himself time to get his house and everything in order but it was denied. So basically he had spent the rest of that week trying to get his shit together and see his family before he left.

We made plans to try to hang out the next day. He obviously had a lot going on so I wasn’t expecting to hear from him. He called me that morning and we talked for about an hour and he kept saying that he would do what he needed to do so we could see each other.

Several hours passed and I thought that was it. I really couldn’t hold it against him. Deployment is a lot to handle. 10:30 pm he called and said he was coming to pick me up. OH SHIT. It’s my time to shine.

I threw on some semi-attractive lazy clothes and made myself look like I hadn’t lived on my couch all day. When he got me, it just felt off. He, understandably, wasn’t as talkative with everything going on but we really didn’t have any banter. What was a 12-minute drive felt like 30.

The house was nice. Garage, hard wood floors, 3 bedrooms, jacuzzi tub, the whole thing. He gave me the tour and as expected, we started making out when we got to his room. Things were promising. He was a decent kisser and as I slid his shirt off I felt how soft his skin was and that he was ripped. Fuego.

Then shit got weird. So at that point we were both naked and standing. He then went behind me to suck on my neck and attempted to finger me. I mean I saw where he was going but, it probably would have worked better as the method to get my clothes off.

He kept going with it and wasn’t being too aggressive so I took the lead. I got him on the bed and started blowing him. To start, he must have rubbed something on himself before I got there because he tasted so strongly of soap and tea tree oil. It was like licking a yoga mat. On top of that, he was SILENT. No moaning, no words, nothing. This was an area I felt confident in so after awhile I kind of just came up for air and figured he was good.

I then asked if he could work on me for a bit and this fucker suggested 69. Ugh. Fine. He wasn’t very good. If I had to describe it, it was like he was trying to suck the meat off a chicken wing. Plus anytime he was doing something good, I’d verbalize it, and then he’d immediately switch to something else. THAT’S NOT HOW IT WORKS.

He randomly stopped so I hopped off and we started fucking. Things were going well. We were finding our rhythm. But then he stopped again.

“Did you cum?”

“No, did you?”

“I am so sorry. I did. It’s been awhile, I’m so sorry!”

We had been having sex less than a minute.

I didn’t know how long it had been for him but based on how embarrassed he was and what I knew about his last relationship, it had to have been in the year+ range.

We made out a bit and snuggled for awhile. He had to pack so he said I could hang out and watch Netflix for a bit while he threw his bag together. I offered to leave. I knew he had a lot to do but he insisted it would be maybe 10/15 minutes.

I curled up on his couch and after 10 minutes it just felt too weird. I went upstairs to say good bye and he called me an Uber which I appreciated. We never spoke again.

And so with that, I saved America by fucking one of their finest. You’re welcome.

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Encounter #54.1: Coast Guard

App: Bumble

Name: Jesse*

Date Location: Crema & The Ashford – Jersey City

Location Review:  4.0 Stars – I fucking love this coffee shop. It’s adorable as shit plus the owner is almost always there so everyone is on point.

4.0 Stars – Cool date spot. The decor makes it feel a little sexy with the velvet wallpaper, happy hour is good, beautiful rooftop, and has a gay bar attached.

Date Duration: 6 hours

What Happened:

Jesse wasn’t normally my type but, he was a winner of “How Hot Can I Bag”. He was about 30, in the coast guard, and lived in the neighborhood next to my office. This could work.

What stood out to me was how straight forward he was. We had been chatting back and forth over the weekend on Bumble and then he asked for my number. Since he was driving, he gave me a call. In my youth, this would have pissed the shit out of me but he let this joke go so it all worked out.

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We talked on the phone for about 2/3 hours and conversation was pretty easy. We were both laid back people with the most vulgar vocabulary so the jokes were flowing. He grew up military so he had lived all over the place but what stood out was how much he loved Boston. He apparently memorized my whole profile, knew my hometown, and said a major reason why he swiped right was because I was a New Englander. Never in my life had it benefited me this much to be from the north east.

He was also very candid. We talked about past relationships and without much prying he told me that he had been single for about a year, was previously engaged, and that it was a long distance relationship. Because of this relationship, he stopped drinking. Also something that normally would bother me but, for whatever reason I wasn’t phased. He seemed to know his own limits and had it handled. We made plans to see each other the next night.

Jesse wasn’t into the bar scene. Not just because of his sobriety but he just was weirded out by the whole online dating thing and would rather grab coffee and walk around. We met at a cafe by my office to start off the night. He looked a lot like his photos, maybe a bit more rough around the edges though. I knew he was also pretty crass but let’s just say you could tell he worked on boats based on how he spoke and carried himself.

Conversation was okay, not as good as it was the night before. I became hyper aware of this and started making jokes to fill the silence. Apparently, I went too far. I had made a joke about crying in the shower and another about getting hit by a bus to pay off my student loans which then led him to keep asking me if I was okay. Yes, bitch. I just think self deprecation is hilarious and I’m nervous GAH.

We finished our coffee and went for a walk around the neighborhood. I could tell he definitely wanted to touch me but for whatever reason, he didn’t throughout the whole walk. I figured I had said too much weird shit but then he asked me if we wanted to go somewhere else and get something to eat. WELL SHIT.

Despite him being crass, he was respectful. When we got to the car he opened the door for me and when we parked he came around to my side to walk with me which I found sweet. As we walked to the bar he started to get a bit more physical with me. If there was a puddle he’d pull me to the side or pull me back in if I was about to step into the crosswalk too soon. Just oddly sweet, gentlemanly stuff.

We sat next to each other at the table and wouldn’t shut the fuck up long enough for the waitress to get our order. Things were finally moving in the right direction. Or at least I thought.

Over time, he started touching my leg, stroking my arm, and then finally it happened. We kissed. And it was pretty solid. He held my face and had his fingers all in my hair. Right amount of tongue. And when we stopped we had that moment of eye contact when you both think OH FUCK YEAH and then do it again.

Despite this solid kiss, I apparently wasn’t as open as I thought because he said, “You come off pretty icy. I can definitely tell that you’re a huge softie on the inside but it feels like you have a wall up”. Well that was some fucking news to me.

Later, I had made some comment about how I was surprised he was still out with me. He was a fucking 10 and I am…well I am my weird ass, trashy, self. He took it a bit the wrong way and started going in on how I was so beautiful, funny, and all this other shit. Listen, I don’t need someone to build me up. I was just saying that he was hot AF. That’s it.

Somehow, things seemed to be fine. He drove me home and on the way we kept playing each other songs we had on repeat. Apparently mine were sad…wtf.

He parked and as I got out I couldn’t figure out how to lock the door. I made some joke about trying to find the clit and he made some comment about how whatever I was saying/doing was working on him. Boom. Success.

At the door we made out a bit and he was pushing to get upstairs. I declined. TBH I wanted to say yes but my room was a mess and I wasn’t feeling all too fresh if you catch my drift. He left a bit abruptly after that and I told him to text me when he got home.

On his way home he sent me a song he thought I’d like. I quickly listened to parts of it and thought nothing of it. The next day, I didn’t hear from him. I took another look at the song and more or less, it’s about a woman who loves a man but eventually gives up because his walls are too high and he’s too depressed. COOL. Message received. I’m an icy bitch.

I remembered that he had his medical clearance test that week so a few days later I asked how it went. Apparently it was a fiasco but he didn’t really say much about it. 24 hours passed and I figured FUCK IT. I’d shoot my shot and I asked what he was doing that weekend. No answer. Cool, I guess I did come off a certain way.

I licked my wounds, kept going, and then I got a phone call.

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