When I was around 23 or 24 I met Cailey. She was a year or so younger than me. She was a short petite dirty blonde girl. She had these big expressive eyes that almost seemed too big for her face but they worked. She wasn’t the typical “hot” but she was very pretty and her fearures all complimented each other. She was tiny maybe 5 foot 2 but her body was pretty low-key perfect. Nothing too big or too small, all squeezable, but you can get a firm grip on. And she had tattoos and some of the sexiest places, her forearm, the back of her neck and on her hip bone right next to her pelvis. She had this birthmark, a little freckle looking dot right on one of her lips. I called it her tickle button.
Dating or hook up site I can’t remember which. By this time I lived way in the south of the US and she lived in Canada real close to the United States border so I’m not even sure how we matched up. We end up talking and getting to know each other, she’s extremely funny a little bit of a Stoner and she enjoys playing video games so someone right up my alley. We ended up striking up a semi relationship, and that evolved into having some fun over Skype. At first we we’re just dirty talk, then I started to show her me jacking off, she finally got the courage to let me see her finger herself, and eventually she let me enjoy watching her entire body and face. As time went on we got more and more comfortable with each other, asking each other to do more intense things. We really opened each other up more sexually. We both had an understanding that even though we weren’t really boyfriend and girlfriend due to the distance, we kind of sort of were as neither of us were seeing anyone else.
I was going back to my home state up north for my buddy’s wedding. Once I let her know we started planning me visiting her. Where she lived was about an 8-hour Drive from where I was going to be, so I flew out a few days early, got my passport ready, and made the drive towards her. The entire week before she and I have been playing a dirty little game. We what each send each other nudes and videos and sexy shit the entire week… But neither of us was allowed to touch ourselves at all. No masturbating, no teasing, no gripping, nothing, until I got to where she was in Canada. It was absolutely torture. Cailey was an inherently shy girl, and although I definitely open her up to a lot of new things, she still had that hint of shyness center. But not this week. She took some the sexiest most arousing pictures that she had ever taken for me up to that point. And I would just get rock hard every single time and have to send her pictures without being able to touch myself. It was a week of hell, but honestly it was pretty fun.
I finally get there and check into my hotel as she still lived with her parents. She arrives shortly afterwards and it was awesome seeing her for the first time. I could tell she was anxious and skittish and very shy, but she still planning a quick kiss on me. We went to the hotel bar to grab a drink and a bite to eat while we connected. Her face was red and she was super shy the entire time but it was really cute. I was nervous as well but I’m definitely more of the outgoing type. We go smoke real quick in her car and I wanted to head back up to the room since I’ve been in the road all day I wanted to relax for a bit. As we get up to the room she sitting down her bag and in my head I just decided I was going to go for it, get all of this nervousness and awkwardness out of the way. She wanted me just as bad as I wanted her and I knew she wouldn’t make the first move, so I legit just walked up to her and pulled her close to me and started to kiss her. She fell right into it and after a couple seconds wrapped her arms around my neck.
She was so tiny, I just scooped her up in my arms and walked over to the bed. I lay her down and start working her shirt off and I start kissing all over her neck and her chest and skin. She was wearing this blue bra and panties. I keep kissing her lips as I’m feeling with her jeans and I finally get them on buttoned and raise up to start pulling them down. I love eating a girl’s pussy. I could basically manhandle her so I just got on my knees and pulled her pussy towards my face. I honestly ate it for quite a long time, wrapping my lips around her clit and humming the alphabet, the occasional deep dive of my tongue inside of her. When we at first started messing around I knew that she didn’t like anal or getting her ass played with, she had done it literally once for me and barely that time, AND had said she wouldn’t again. But I kneeled the and ran my tongue straight to it and ate it, I didn’t give a fuck (she told me she actually loved it).
After a bit she asked if I wanted head.. of course. She raised up and undoes my pants and put me in her mouth. Now again Cailey was small, and my cock is actually pretty fit… It’s definitely well above average length and pretty girthy… it’s always been my favorite attribute on my body. So she had a hard time going to deep on me at first. It took her a little bit of warming up but she could finally make it about halfway down. It started out as I knew it would, nice and timid, little licks here barely putting it in, but as she did it more she got more exuberant and more into it. And she even licked down to my balls and tried sucking them in her mouth. She and I had talked about some kinky dirty stuff throughout the months we had been talking, but you always wonder if that’s what the person is like in real life. So far everything living up to it.
When we had been discussing us having sex previously, we had went through all of the typical questions: should be wear protection, what can I do or can’t I do, where am I allowed to cum, etc etc. She had said she wanted us to wear protection at least the first time you know since everything is new and we’ll see how we’re feeling moving forward. I agreed with her. I mean condoms suck and obviously I would have rather done it without one but rather be safe than sorry. Now that we’re going to get at the moment I laid her back on the bed and comment on top of her and just started making out with her. I reached down and was fingering her some and she had her hands on my cock and was jerking me. To my surprise she started rubbing my cock on her pussy. I even said hold on let me get a condom and she just told me it’s fine it’s fine. She starts trying to guide me inside of her, but she was tight… Like tight tight. I pushed and pushed as gently as I could but she was so unbelievably tight. She was good and wet but I just couldn’t get into her. She starts apologizing which was silly like you literally never have to apologize for having a tight pussy. I just told her to turn around and she bent over. I bent over and spit on her pussy a little bit, and told her to spread it open. With her face in the pillow she reached back and with both hands grabbed the sides of her lips and just spread them as wide as they could go. They’re still was a fair bit of pushing, but after a minute or so I finally got the tip in. A little while later I’m fully inside of her and she is gasping.
I really thought I was going to nut immediately, especially as long as it’s been. I rarely go more than a couple of days without beating my meat, so getting teased and poked and prodded all week long without being able to touch myself was the worst. I kept at it. She had told me before during our naughty talk that if I was hitting it from the back she wouldn’t reached back and start playing with my balls. And she did just that. I had never had that done before and it felt amazing. A little bit she got on top of me she said she’s been wanting to ride me for months. She gets on top of me and plants on her feet so she’s squatting, which is my most absolute favorite, and she starts doing squats on my cock. She had told me that she obviously wasn’t a virgin but she hadn’t had a ridiculous amount of sex, I think she had maybe four partners before me. But it seemed like she knew what she was doing.
She put her knees down and starts riding me low. She bends down to kiss me and our bodies just start vibing and grinding on each other. I’m about to cum… I voice it like most people do, and she raises up and continues grinding on me. I remember her looking right in my eyes as she’s just grinding away. I feel myself start to nut and I tell her and start pulling her body up. My cock slips out and an absolute fountain of cum, by far the largest amount of cum up to that point in my life. It’s just flowing out of me right onto my stomach. Cailey was gasping and looking down at what she did to me. She lowered herself back down as I’m cumming and sits her lips on my shaft and starts grinding on me back and forth as I’m cumming. I was looking at it and it was one of the sexiest things I’ve seen. Just watching her pussy slide up and down forcing more jizz out of me, watching as it gets on her lips and she’s just taking it and rubbing it all on her pussy. It was one of the greatest nuts ever.
As we start to come down off of the high she just lays down on top of me with her head next to mine on my shoulder. I can feel all of the juice and the stickiness from my cock on our stomachs. We lay there for a while with me rubbing her back up and down and grabbing on her booty. After a few she rolls over and I went to the bathroom to grab a towel and I wipe was both down. After I went to Stone I just look at her and laid back on top of her to start kissing her. The rest of the trip was a breeze and an amazing chapter in my life. We went out to dinner and she took me to some cool spots but for the most part we would always end up right back at the hotel just fucking each other. She let me cum on her tits, she swallowed me a couple of times, I made her cum eating her out.. we did it in the shower, in her car, in the rental car that I had, went to her house when her parents weren’t there.. it was bliss.
Eventually Cailey and I broke off. We had kind of a bad breakup. I didn’t talk to her for a long time and the next time I spoke to her on Instagram, she had gotten married. She had also gotten really sick. Shave your head sick. Last I spoke to her she was undergoing chemo. She was always a great girl. I hope she’s doing well
Source: reddit.com/r/gonewildstories/comments/ql6n5c/my_first_time_in_canada_mf