The first time I squirted [FM]

There’s a lot of controversy around squirting, what it is, how it happens, all of that. I don’t really know much about any of that because it’s only happened to me a few times, and it’s usually a massive surprise. I can sort of make it happen now, but it takes A LOT of effort. Now there has to be this perfect storm of clitoral stimulation, g-spot stimulation, and anal stimulation for it to happen. The last time I squirted my husband had me on my hands and knees and I was using a vibrator on my clit, I had a large butt plug in and he was fucking me from behind really hard and it just happened – a total surprise, but I think that’s how I can make it work if I want to. I don’t know, my body is a fucking mystery to me sometimes.

Anyways, here’s wonder wall.

It was the between high school and college and I was on a trip to NYC to look at colleges, I had a few interviews setup and I went with my best friend and her older brother. My friend, Cara and her brother TJ, their parents put us up at this hotel near the New School where we both had interviews. The hotel was supposed to be nice, but it turned out to be a glorified hostel that also rented rooms. It was New York at it’s finest. The place had no AC and a giant window that opened onto a fire escape and a bathroom that was literally just a toilet and a corner with a shower head, not even a curtain.

Cara’s parents were super laid back about everything. She got a tattoo at 14 and they didn’t care. She was straightforward with them about wanting to go on the pill because she was having sex, they were cool with it. She had no restrictions on going out or traveling. When she was 16 she went to Paris by herself for five days. Yeah, they were a bit free-range. They sent TJ along because they wanted to keep up some sort of semblance of being good parents.

TJ was 22 and in the process of transferring from UCLA to some school in London where he was studying some sort of history that was too boring to talk about. He was a cool guy though, former jock who blew out his knee and decided to get more into academics. He was around 6’1 and 200lbs and kept his head shaved bald which looked ok on him and didn’t make him look like a thumb or a penis.

We did our interviews, Cara’s went amazing and she fell in love with the school, I thought they were a bunch of pretentious pricks and wasn’t a fan of their whole everything. I kind of soured to the whole thing half way through and they could tell and the interviews just kind of tanked. I’m not a huge fan of NYC anyways so I was okay with not going there. I like my beaches.

So, hers goes so well she gets invited out to dinner and a night out with a bunch of the current students that would be in her program. She’s ecstatic and goes off with them leaving TJ and I to fend for ourselves. I’m pretty bummed about the whole experience so his big idea is we get some take out, get some booze and go watch movies in the room which sounds a lot better to me than wandering around a city I didn’t like that much.

We wrap up our disappointing Pad Thai and are on our second round of whiskey and cokes – he got to pick the drinks – and I can’t even remember what we were watching. But, Cara texts and says she’s going dancing with some people and she won’t be home until super late, and we say cool – our flight is the next morning at like 6 am so we’re probably going to have to drag her still drunk ass through the airport.

I decide to jump in the shower. The water never really gets hot and I’m annoyed. I turn off the shower to realize that my pajamas had fallen on the ground and were totally soaked. So I hang them up and do my best to cover up with the hotel towel that is slightly larger than a wash cloth and head out to my backpack to grab something else to wear – I barely packed anything cause we’re supposed to be here for like three days total and I didn’t want to pay to check a bag.

TJ is pretty openly staring at me in my towel and asks what’s up. I tell him about the pajama situation and he asks if I want a pair of boxers or something. I say sure because my options are wearing my jeans or sitting there in a thong. He rummages through a bag and tosses me a pair of red and black checkered boxers. I pull them on under my towel and they barely fit. Then I put my t-shirt back on from earlier in the day.

We get back to drinking and we’re laying side by side on the smaller of the two beds. He starts asking me about my boyfriend – who I dumped for cheating on me like a week before. And I ask him about his girlfriend – who he dumped for cheating on him a month ago. We have a good laugh about it.

Then he says he’s going to have a smoke, and he goes out on the fire escape through the window and is sitting there smoking in his boxers and t-shirt. I climb out and join him. He’s sitting on the landing and I sit on the steps kind of above him and he offers me a cigarette. I was kind of drunk at this point and have been known to smoke then, so I took him up on it. He lit a cigarette for me, and put it between my lips and brushed my face with his other hand, and for some reason it was so highly sexually charged I suddenly felt it in my stomach. He smiled and we kept talking.

We were talking about NYC verses Los Angeles. Then he just says, mid conversation, “Have you ever had anyone go down on you while sitting on a fire escape in the middle of New York?”

I was kind of shocked, kind of laughing, “You know, I don’t think I have had that specific thing happen to me.”

“Well,” he said, “Let me know if you want someone to make that happen.”

“Do you know somebody that could help with that particular scenario?”

He nodded and smirked, putting out his own cigarette and flicking the butt out, watching it fall the five stories to the ground.

I looked around. It was dark, but there were a lot of windows facing us. There was no light on the landing, but we were pretty heavily backlit by the light from the hotel room. Just five feet away was another window for the room next door, but there was a TV going loudly in there.

“If you tell your sister, I will kill you.”

“Noted,” he said.

I pulled off the boxers he’d loaned me and tossed them back inside the hotel room window. The metal stairs were a bit cold on my bare ass, but not too bad since it was so hot out. He crawled between my legs and put them up on his shoulders, suddenly leaning me back more against the stairs. I braced myself with one arm feeling the grit of the steps on my bare ass cheeks and forearm. I finished my cigarette with the other and flicked it away.

He didn’t start slow or bother kissing around or working his way up, he just pushed his tongue right against my pussy lips and parted them, rubbing my clit with the tip of his tongue. I felt like I got tasered, but you know, in a good way.

I couldn’t help looking around at all the open and lit windows. I didn’t see anyone staring at us, but with the hundreds of windows, there had to be someone. It was a fun idea. The drunkness and the exposure was making me wetter than I typically get, which is a lot.

TJ slid what felt like two fingers inside of me and was thrusting them in and out while putting solid licking pressure on my clit. It was amazing. It had been at least a year before someone had gone down on me with any sort of skill. I didn’t even come close to realizing how much I missed it.

I was just trying to hold on to the railing and not scream as he picked up speed. He was really good at this and he knew it. He’d stop for a second when I got close and smile at me. He did this a few times, edging me closer. No one had done that before and it was fucking frustrating and fucking amazing at the same time. At one point I was sure I was a second from cumming and he stopped and held his hand still.

I felt the orgasm recede and grabbed his hair, “don’t do that again!”

“Yes ma’am,” he said laughing.

It took a few more minutes to build back up and I was seconds away and he paused. I kicked my heel into his back a little and he upped the speed and dug in and varied something because it went from like an 8 out of 10, to a 25 out of 10 and I felt my entire body tingling and building in anticipation. If he stopped this time, I’d kill him.

Then he didn’t. And I couldn’t control myself. I started shaking and grabbed his head tight. I felt the fluid flow out of me and down my legs and into my ass. It lasted at least ten seconds. I probably sounded like a cat dying out there. He looked up at me and his face was dripping and the collar of his shirt was soaked.

“How the fuck did you do that?”

He laughed and wiped at his mouth with his shirt, then stood up and he had a massive hard on poking through the flap in his boxers. I pushed him back and dropped to my knees in front of him, the grating pushing against my bony knee caps felt kind of sexy and dirty or something. I could feel the breeze on my pussy and ass because they were literally soaked.

I pulled his boxers down and he stepped out of them. I tossed them in the room. He turned and braced himself against the window and I started stroking his pre-cum soaked cock, which was quite bigger than I had ever imagined.

He came in record speed inside my mouth, then spent 15 minutes apologizing for cumming so fast. We took a shower in the weird bathroom and laid back on the bed. As we were talking about a round two, his sister came in and we pretended like nothing happened.

Source: reddit.com/r/gonewildstories/comments/af6eu1/the_first_time_i_squirted_fm