That time I went on [M]y [F]irst real internet date

Ok..here we go. In some of my previous stories I mentioned that a lot of my shenanigans were after a long relationship I had ended and I was out exploring again. Well, now, I’m going to tell the story of the wonderful, sweet and sexy girl that was the person who I dated right after that break up.

A little background. I was with my ex for nearly 10 years and she was a strong type-A personality who had always planned and dictated most of our lives together. I think she even planned the 1.5 years of ignoring me sexually that led to our break-up. During that 1.5 years, I developed a wandering keyboard (online shenanigans), but those are stories for another time. After the break-up, move-out and fresh start, I found myself looking to date for the first time in a long time. I signed up for one of those free internet dating websites that a friend recommended. I posted a few pictures where I looked thinner and younger, wrote out my stats, was fairly open in the profile that I wasn’t looking for anything too serious at the moment and that I was just out of a long relationship.

At first I was just clicking through the profiles of the women I thought were cute, thinking to myself “I’d do her… (click) I’d do her… (click) maybe… (click) she has a cute puppy… (click) I’d do her… (click)” But I was still a bit broken and wasn’t really having the courage to write anyone. But slowly over the course of that week 5-6 women had written me, and I was exchanging back and forth with them.

So.. I went on my first internet date of the modern era. I chose beauty over connection. We had exchanged 3 messages online and she asked me to meet her at a bar. She was about 5’6”, blonde, she had a slight hourglass figure with hips that made her curves stand out in the sundress she wore. Ohh, that sundress looked amazing on her. A pretty face and a smile that lit up the room. I was wayyyy in over my head for my first internet date. And she knew it. She was an internet dating pro and I was fresh meat on that site. We met a the bar and she had a lists of questions, this date felt more like an interview. She wanted to know about my job, my work schedule, my desire for kids, why I stayed with my ex so long, how close am I to my mom, who won the 1988 world series, whats the difference between a peach and a nectarine!? It was a bit overwhelming. I was a deer in headlights and it was clear I was not on the same internet dating level as this woman, by far. The date was a bomb…

I went back home with my tail between my legs. Internet dating was officially stupid!

When I got home that night, there was a new message waiting for me. It was from a girl named Megan. We had already exchanged a few messages, and she seemed genuine and friendly, and I was feeling open and vulnerable at the moment, and I told her about my first internet date and how awkward it was. She replied right away, “oh no, you poor thing, you need someone to go slower with”. We kept exchanging messages through the night and moved to texting somewhere in the middle. She was playful, friendly and sarcastic. By the end of the night she was like “Maybe you’re not ready to date yet, but it sounds like you could use a drinking buddy. Let’s hang out tomorrow night”.

So, I met Megan just down my street at my local bar (which is really the kind of bar the college kids go to party at). I saw Megan as she walked into the bar, she was about 5’9”, she had dressed casual for our night of drinking in jeans and a t-shirt. The jeans gave away that she was in amazing shape and while thin, had the kind of ass you only get from living on the stair master. We could only find a seat at the bar since the place was crowded on a Saturday night. And I ordered us a couple of beers.

She told me all about herself. She was from the midwest originally, moved to LA to become an actress, worked as a flight attendant for awhile, but that made it hard to meet casting calls, so she recently switched to being a waitress / manager at a restaurant in my neighborhood. She told me she had worked the past 6 days straight and was looking forward to some good drinking. And that’s what we did. We talked and drank and just relaxed like friends might. I could walk home from that bar, so I didn’t really hold back. And neither did she.

Somewhere around midnight I said “I think I’m pretty buzzed”

Megan “So you’re saying you should drink more?”

Me “I’m saying we should slow down”

Megan “So you’re saying you should drink more?”

With that Megan called the bartender over and ordered two more beers. This girl was amazing at holding her alcohol. I’m 6’1” and 210 lbs and I was already feeling pretty drunk, how the hell was she keeping up. She saw my confusion as she picked up her next beer.

“I’m from the midwest” She said as she started to drink it back.

So I just went for it and kept drinking.

At 1:45am, the bar was closing, and my world was spinning. We stumbled out of the bar together. Megan knew I only lived a couple streets down.

Megan “Cool if I crash on your couch?”.

Me “Yup”

We walked back to my place. Well.. walking is something you aspire to do when you’re as drunk as we were. We swayed, stumbled and yelled at the top of our lungs and laughed, lots of laughing. When we got back to my place, the first thing she said was “do you have anything to drink here”. So I got us each a beer from my fridge and we sat on the couch. I wish I could tell you I had some smooth move that I used on the first girl I kissed after my break-up. But honestly, its all a little too blurry to remember who did what when. The next thing I know Megan and I are kissing and making out and our hands are all over each other. I’m in this drunken state of awe, because this girl’s body is amazing, she must live at the gym. Everything is tight and firm and flawless.

I pulled her t-shirt off and underneath she was hiding large D-cup breasts that are nearly spilling out of what looks like a bra that is 2 sizes too small for her. She lays back and smiles “I had my boobs done when I moved out here, do you like em?”. That’s LA for you folks. But fake or not, they looked amazing. I undid her bra and her breasts spilled out. They looked and felt great, who am I to judge. She had small scars under them, but if you weren’t looking, you wouldn’t notice. I kissed, fondled and sucked on them. Megan reached down and undid my pants at the same time and reached under them and started to stroke me. This felt amazing.. I love my new drinking buddy.

Something peculiar happened right about then. I don’t know if it was because I had too much to drink, or because Aliens had decided to abduct us, but suddenly I was removed from that scene and I was waking up sometime later on the couch. Megan’s hand was still down my pants, her shirt was still off, but she was asleep ontop of me, and there was sun outside the window. We apparently had passed out, the both of us, somewhere around the best part of this story. Why would the gods punish me like this! Why would you the reader, be punished like this. I shuffled out from under Megan and went to the bathroom. When I came back she was already re-dressed and looking a hot-mess and said “I need to get home, where I can be sick in peace” And she left fairly quickly.

Overall, not a horrible second internet date.

That night, Sunday night. Megan texted me:

Megan “How are you feeling”

Me “Was a wreck all day, but maybe 70% now”

Megan “Me too, but around 5, I had some wine and it cleared my head”

Me: “I can’t stomach beer and it’s all I have. So, I’m just drinking water”

Megan “Awe, do you want me to bring you gatorade or wine”

I opted for both and 30 minutes later Megan was standing at the front door of my apartment. Holding a bottle of white wine in one hand a fruit punch gatorade in the other.

She was wearing skin tight yoga pants and a t-shirt. I couldn’t take my eyes off her ass in those Yoga pants, I don’t care how hungover I felt. I was instantly hard as soon as she walked into my place. She went to my fridge and put both of them away and came back and sat next to me on the couch.

Megan “did you have fun last night?”

Me “The parts I remember, yes”

Megan “Uggh, I’m so sorry, I passed out while giving you a hand job, that’s so lame. It’s like your first hand job of being single, and the dumb bitch passes out”

Me “Oh, I thought I was the one that passed out. I thought you were all, I’m trying to throw this loser and hand job, and he passed out on me”

We laughed at each other because of our confusion on who passed out first. We ended up just drinking the gatorade she brought and watching Netflix on the couch for a couple of hours then she stood up suddenly and grabbed my hand. She said “come with me” and she led me into the bedroom. “I want to make up for last night”. She said as she pushed me down on the bed. She told me to stay right there and she backed up 3-4 ft. She looked at me and said “Lay down, you’re weak” and laughed at me. I wasn’t feeling very weak at that moment, but I did what she said.

She lifted her shirt up over her head and revealed a powder blue bra that fit her body much more naturally than the one she was wearing the night before. Then she slowly, peeled her yoga pants off. She turned sideways slightly so I could see she shape of her hips and ass as she peeled them off, underneath she had powder blue bikini cut panties that matched the bra. My heart was racing, and my cock was suddenly throbbing in my pants. I remember this moment so vividly, because it was one of the sexiest things I’ve seen in my life. The way her panties tightly clung to her perfectly shaped ass and hips. How she twister her body to show me, and how the yoga pants peeled off her skin. This has been a reoccurring moment my in mastabatorial fantasies for sometime after. After her pants were off, she reached back and undid her bra and let it fall to the floor. She was standing in front of me in just her panties now. And she did a little twirl and asked

Megan “What do you think?”

Me: “umm, umm… The Dodgers won the 1988 world series!”. Wait, that was a different question. I was actually in shock and I think I just stuttered for a few moments.

Megan walked back over to the bed and crawled ontop of me, like she had rehearsed the sexiest way to crawl over someone with her body. She kissed me on the lips for a few moments and then she whispered in my ear “I want to take care of you”. That either sounds really psycho or really sexy depending on the moment, and at the moment it was the sexiest thing in the world. She slid down my body and undid my pants. I was so hard I actually sprung out of my pants as she undid them. My eager cock had all on it’s own figured out how to worm through the hole in my boxers, too eager to see someone besides my hand.

Megan pulled my pants all the way off without touching my cock. And then repeated the motion with my boxers. I took the cue and managed to take my shirt off all by myself, until I was laying naked in front of her. She smiled and genuine smile and looked at me. She pushed my legs apart and sat on her knees between me legs. She sat up, so I could see her nearly perfect breasts and body, and she smiled again and reached down and started to run her fingers over my cock. She looked down at it intensely, like she was trying to learn it, or get to know it, or something. She just slowly teased it with her hands with her other hand she started massaging my inner and upper thigh.

Megan “You have a nice cock”

Me “thanks… you have a ridiculously perfect body”

Megan: “Thank you… do you want to be inside me? Or do you want to take it slow?”

Me: “I want to be inside you…but, but… I wasn’t planning on this happening yet, so I don’t have condoms…umm..umm..”

Megan: “I figured as much, so I got some at the store when I bought the gatorade, I’ll be right back”

Megan stood up again and disappeared from the bedroom. She came back a minute later with a box of condoms. She handed them to me and she stayed standing next to the bed. I looked up at her and she repeated that slow stripping motion she did before as she pulled her panties down off of her hips. And let them fall to the floor. She was completely naked now. And my cock swelled back up to it’s full glory. She was completely smooth an hairless down there, and as to turned so I could see her ass, I saw that she had a little wavy back tattoo just above her ass. A tramp stamp, some might call it. She bent down and ran her hand over it and leaned down and kissed me on the lips. She crawled back on the bed and over me. She straddled me, as I reached down between us and slipped the condom on. She reached down and took me in her hand and the slowly leaned back until it the tip of me was pressed against her pussy. I realized how weird it was that I hadn’t even touched or teased her pussy. I had no idea if she was even wet… but she was. So wet, that I slipped inside her easily as she lowered her hips. She let out a sigh of pleasure, like it was something she had been waiting for. Her hands slid onto my chest as she arched her back and started to move her hips back and forth. She lowered her body and we started to kiss softly and slowly as she kept rocking her hips. My hands slid onto her hips, holding her, feeling the way she moved them. Her pussy continuing to slide up and down my cock. She was starting to pant and moan between each kiss.

After a few minutes she sat up, letting me look at her body. She leaned back and slid her hands under her D cup breasts and started to bounce up and down on my cock. Letting me see her body and the way she arched, bouncing and rocking up and down on me. She started to dirty talk as I watched her, moaning out
“Fuck, I love your cock”.
“I love you being inside me”
“Tell me you like my breasts”
“Tell me you love my tight body”.

And I told her,… I told her how fucking hot she looked fucking me. And it just made her start to ride me harder and harder. She planted one of her hands in the middle of my chest and she closed her eyes and just started to work her hips back and forth. She looked like she was ridding a mechanical bull the way she was grinding her hips. And this moment too still lives on in my memories, so vividly.

I want to say how long this is going on is normal, but it isn’t. Normally, I would have lost my load 10-15 min in. But something about the nerves of being with the first new girl in 10 years, and also how quickly this was happening. Well, I’m the type of person that thinks too much and gets too in my head, and now she had been riding me for nearly 15 minutes straight. Her body was glistening with sweat and her skin was wet to the touch. I pulled her close and whispered to her “Maybe you should let me take over”. She nodded in agreement and crawled off of me, and without any instruction from me, she laid on the bed next to me on her stomach, and slid her knees up the bed and stick her perfect ass up in the air.

Megan “Like this?”

Me “umm..yes, always”

I rolled over and slide behind her, as I did she slid her ass up higher in the air, and I slid back inside her from behind this time. Fuuuuck her ass looked amazing as I started to bounce against it. She really must spend hours at the gym sculpting that ass. I grabbed it, held it, ran my hands over it and she started to moan back at me as I fucked her harder

Megan “Do you love my ass?”
Megan “Tell me how much you love it”
Megan “You can own this ass, it can belong to you…just keep fucking me”

At this point she’s driving me crazy. She starts to wiggle her ass as I plunge away, shes rocking her hips back against me. This girl doesn’t know how to sit still. She reaches down under herself and is rubbing my balls as I fuck her now.

But…but… I think I’m just broken. It must be the hangover, or the nerves or I contracted rare disease where you can’t cum no matter how long you fuck. How can I live like this!!! I’ve been taking her from behind now for another 15-20 minutes and she’s arched and moved in every way possible. She looks incredibly hot, and I’ve been fucking her hard this entire time. But the damn thing just wont fire. Did I forget to load it? How do you load it? Fuck…I forgot how my dick works. This time I’m the one covered in sweat and looking exhausted. She looks back at me

Megan “Are you close?”
Me “I don’t know… I think I’m just not used to using a condom all the time?”
Megan “Aww… maybe we can try something different then”

She pushed my sweat soaked body back down onto the bed and pulled the condom off me. She grabbed my shirt and she spit on my cock, and used to shirt and her spit to whip some of the condom lube from my cock. She seemed like she’d done this before, I remember thinking. She leaned down and took me into her mouth. She looked up at me with her dark brown eyes and held me in her mouth. Her head didn’t move much at first, she just held my cock in and moved and slid her tongue around me while her mouth flexed around me. It felt amazing, she slid me back out of her mouth a little, so just to tip was insider her mouth. Her hand gripped my shaft and she started to stroke me faster and faster. Her tongue swirling around the tip inside her mouth. Her eyes never left mine, she had this look like she wanted approval from me, and she wouldn’t look away until she had it. Her breasts were hanging down and brushing against my thighs as she kept on sucking me.

It was too much, I was getting so close. I told her “I’m close…”. She was letting her drool slide down my cock as my shaft and her hand became wet, she just started to stroke me faster and it feel better and better. Then I felt my cock started to pulse and her lips wrap tightly around me. Her eyes went wind as I felt my cock pulse inside her mouth. She effortlessly swallowed each and elver pulse and then ran her mouth down my cock and sucked off any mess there was left..and then collapsed in exhaustion next to me in the bed.

She later told me, she had a couple of small orgasms while we were going at it. But that the real big orgasms, she seemed to only be able to give herself with a toy. But that she’s a big people pleaser…so I shouldn’t worry. We collapsed after that and fell asleep. I’m terrible at sleeping next to someone new though, so I woke up at 5am and tossed and turned until 6am, when she woke up and realized I wasn’t asleep, she gave me head and swallowed all of me again and said she should head out and beat the traffic home so she could nap before her work started at around noon.

Source: reddit.com/r/gonewildstories/comments/92pi1q/that_time_i_went_on_my_first_real_internet_date