When I first heard that there were teen dating sites, I assumed that it was some sort of joke. I was in my mid twenties, and every dating site I had ever been on or heard of was very strict about requiring the users to be over 18. So when I heard that teenage dating sites existed, I had to check them out, out of curiosity more than anything else.
Like most dating sites, I needed to make a profile to look around. My profile was actually pretty honest. I used a real picture of my fully bearded adult self. I even selected my honest age, 24. It was the oldest age that I could select. Which was just stunning to me on a website that let you choose an age as low as 13. I guess their idea was that some teenagers who started on the site would eventually grow up into their twenties and still stick around. I dunno. The only thing that I didn't select honestly was my location... after all, I was just here to look around, I didn't want to run the risk of running into some sting operation or some neighborhood kid who might recognize me.
My first experience on the site was... underwhelming, to say the least. I got a few messages from random people (mostly guys, surprisingly) telling me that I was too old to be on the site, a little bit of random smalltalk with girls who posted sitewide messages saying things like "message me", and that was about it for interaction. The most interesting thing was checking out the profiles: most of them were boring girls talking about how much they loved sports and god and just wanted a friend. Which, granted, would have interested me if I was a in high school and looking for a real relationship. but some of them were more risque: they were filled with bikini pictures and had surveys about sex positions and hooking up, and profile descriptions talking about BDSM and roleplaying and stuff. There was nothing that would have looked too out of place on an adult's OKCupid profile, but coming from 14-year olds, it was surprising.
I didn't know what I wanted, but I knew I wanted... something. I started messaging some of the girls and taking some of their surverys and commenting on their pictures. It was fun, until my profile was unceremoniously deleted without warning. I wasn't sure why my profile was deleted, but I had a good idea: I was the adult hitting on girls on the teenage dating site. But it was too late for that to slow me down; I was already hooked.
I was back with a new profile within a few days. I was still being mostly honest. I picked a new location, but still used my own pictures. And instead of leaving my profile blank, I stared filling it in with things like, "Looking for a hot teenage girl who wants to have some fun ;)". Pretty much nothing ambiguous about who I was and what I wanted. And it worked, mostly. I still got messages chastising me for being there, but I surprisingly got some girls who were interested. I was listed as being from Los Angeles or New York or wherever, and they were from all of the country, but they were interested. I think to some degree we knew what we were doing was wrong: I didn't want to give out any identifying contact info, and neither did they. We'd exchange contact info or skype or kik or some other messaging service not liked to my real identity before my profile would get banned, and we talk on there.
The conversations were always the same: we'd awkwardly chat about whatever, I'd pretend to care about their high school drama, and we'd awkwardly flirt. They'd be curious to talk to an older, experienced guy about sex, and eventually they'd unsolicited start sending me sexy pictures. Sometimes in lingerie or a bikini, sometimes fully nude. Either way, they were hot. I don't know why generic nudes or average looking teenage girls turned me on so much more than regular porn, but they did. I'd get the pictures, and we'd keep talking for a while, but things would fizzle out soon. There was no way for them to escalate things, and even if the girl was really into me, I wasn't interested in anything resembling a "relationship" with one of these girls. Hell, I was still half afraid that they were FBI agents.
I eventually got into a pretty regular cycle with the site. I'd make a profile with real pictures of me and a random location in America, fill it in with explicit survey questions like "How far would we go on our first date" and "what sex toy do you want me to use on you." I'd get off-site contact info for some generic middle-America high schoolers looking for attention and validation from an older guy before my profile got deleted. We'd chat and flirt until she ran out of sexy pictures to send me or realized that I didn't have any more to my personality than pretending to listen and looking to sext.
It was the same routine for me for over a year. I could be from New York or Tacoma or Dallas or wherever. All of that changed when I got a message from a 14 year old girl named Jennifer. She was petite and blonde, and even though she was wearing a swearshirt in all of her pictures, she looked like she had a decent rack. She liked soccer and puppies and was a freshman in high school. Her message to me said, "Hey, you look like fun :P" None of that was unusual. What was unusual was that she was from Great Falls, the same city as me.
The was the first time I realized that I could actually meet one of these girls for real... I was nervous, to be honest. I think that if I had actually listed my real location in my profile, I would have been too afraid that it was some sort of FBI setup to respond. As it was, I was from Louisville or St. Louis or wherever. Other than my pictures, there was nothing linking my profile to me. And those were the pictures I had up on facebook and regular dating sites, anyone in the world could have stolen them and made a profile. It was plausible deniability in my mind, and I could back out any time I wanted.
So I messaged her back with a different goal than usual. I normally made a point to never initiate things like asking for naked pictures, but now I was slowing it down even more. I wanted to take things so slow and take so little initiative that if I wasn't talking to a real teenage girl, it wouldn't be worth the time of whoever I was talking to to lure me into some sort of sting.
This time when we talked, I made a point to actually listen. When she talked about her life, I listened and related. I learned that she liked to be called Jenn or Jenni, never Jennifer. I learned that she liked comic book movies and writing superhero fanfiction. And when she talked about sex, I listened and tried to be caring without judgement. She was afraid that she'd be judged or called a slut since she wasn't a virgin; I assured her that people my age expected their partners to have sexual experience. She was embarrassed about meeting people online and being attracted to older guys; I assured her that it certainly wasn't a problem for me.
I actually told her a lot about me too. Nothing too specific, but I talked about playing sports in college and adjusting to life as an adult, about the movies and TV shows I liked, and lots about my sexual preferences and experiences. She liked that a lot. I never told her that I lied in my profile with my location, I simply told her that I had family near Great Falls, that I was familiar with the area, and that I was there pretty often.
We messaged each other pretty much every day. I found myself thinking about her even when I was on adult dating sites or out with girls my age. We talked for months while I was waiting for the invitation that I knew would come, and it eventually did. She told me that when I was in town sometime that we should get together, and I agreed. I told her I would be in town next week and that I'd try to find time to get together.
I didn't know how to set this up... I'd met girls from the internet before, but never someone her age. We talked about ideas for a while. She couldn't tell her parents about me. She couldn't even tell her friends and have one of them cover for her. We eventually decided that she could have her mom drop her off at the mall and that I could pick her up there. We'd be able to get a couple hours together... and then, well, we'd have to wing it. We didn't even talk about what we'd do together, but I agreed to meet her Friday evening at the mall. I booked myself a hotel room nearby, after all, she thought I was just in town visiting.
I was nervous when I went to pick her up. I was pretty sure that this wasn't some sort of FBI sting, but I was still afraid that someone would see us. That she would get get scared and make a scene. That something would go wrong somehow. Still, I didn't come this far for nothing, and I wasn't going to turn back now.
I sat in the mall parking lot and sent her a message, "Hey, I'm here. Parked outside the food court." Then I waited for her text back as I watched the crowd of people coming and going. That's when I saw her walking out of the mall. I'm sure that she just looked like a regular teenage girl to most people. She was wearing jeans and a sweatshirt and could have been any girl in America, but to me she looked like an angel.
She made eye contact with me through the car window, opened the passenger door, and hopped right in. She probably looked like any teenage girl getting picked up by her dad, even if I wasn't actually old enough to play the part. "Um, hi," she said shyly.
I silently let out a sigh of relief and smiled at her. "Hey, Jenni. What's up? You look great," I said, trying to act as welcoming and cheerful as I could. "What do you want to do?"
"Uh, you wanted to go back to your hotel, right?" she asked me back cautiously.
That's what I what I wanted to hear. I told her how much I liked that idea as I pulled out of the parking lot. I tried asking her about her day and school and how she was doing, but seldom got more than a word or two in response. When I asked her if she was nervous, she told me that she was, but excited too. I put my hand on her leg, and she smiled. That was a good enough for me as we drove to the hotel in near silence.
We got to the hotel, and I walked her to my room. It was on the first floor right near the back door, where it was unlikely anyone would see us. "Nice room," Jenni told me as she took a seat on the end of the king size bed and turned on the TV. I sat next to her, my leg barely touching her as she flipped channels. She eventually settled on an action movie, smiled, and told me it was one of her favorites.
I liked the movie too, but I didn't think that silently watching basic cable together was really what either of us wanted. Someone had to make the first move, and I figured it should be me. I put my hand on her cheek and turned her face toward mine. I leaned in and kissed her, gently biting her lower lip for a moment before pulling away. "That's needed to happen for a while," I told her as suavely as I could.
Immediately the mood lightened. "Yeah it did," Jenni responded as she leaned in to kiss me again. Our tongues explored each others mouths as my hand began rubbing her inner thigh. We finally fell back onto the bed together in full-on makeout mode. Eventually she ended up on top of me, sucking on my neck as hands ran up her hips and the sides of her body over her sweatshirt.
"I think we're a bit overdressed," I said as I slid my hands under her sweatshirt and pulled it off over her head, revealing her sexy teenage body and her red, lacy bra. "Wow. You look amazing."
"Really?" she asked excited.
I just smiled back as I sat up and removed my shirt. I pulled Jenni toward me and kissed her again, passionately. My hands ran over her bare skin and hers over mine. I moved closer and closer to her breasts before giving them a squeeze through her bra. "MMmm!" Jenni moaned into my kiss, wordless pleading for more. I squeezed again harder, and she began grinding into me.
I felt my cock twitch as she rubbed against it, and soon it was rock hard in my pants. I thought there was no way that she didn't notice it, and I was right. Soon she reached down and grabbed it through my pants. "You want that cock, baby?" I ask her playfully.
"So much!"
I pushed back on her hips so that I could start undoing my pants and I asked her, "where do you want it?"
"My mouth," she replied, surprising me with her confidence.
I looped my thumbs under the top of my boxers and pushed off my jeans and my underwear in one motion, before gently pushing on Jenni's shoulder, coaxing her down toward my dick.
I laid back as Jenni knelt over my my hard cock. She grabbed it in her hand and kissed the head lightly before taking it into her teenage mouth.
I was in heaven. I didn't realize until now that this is what I had spent months working for. I wrapped my fingers in her hair and thrust my hips up, pushing my cock up into her mouth. "Oh my god, Jenni, that's amazing," I moaned.
Jenni's eyes flashed up toward mine before focusing back on my cock. She sucked harder and tried to get it further down her throat. She wasn't at the best angle to deepthroat it, but her enthusiasm for the idea was incredibly hot. Pulling on her hair, I removed my cock from her mouth, guiding her to kiss and lick the shaft. "That's it baby," I encouraged her as her mouth worked all over my cock. She finally got into a rhythm, alternating licks and kisses on the shaft with taking the whole thing in her mouth. I smiled and moaned the whole time, trying to let her know how much I was enjoying it, my hands on in her hair, gently pulling it and brushing it out of her face.
Soon, I couldn't take it much longer. "You want my cum?" I asked as her tongue ran the length of my shaft.
"Mmmm fill my mouth," the teenage girl told me before wrapping her lips around the head of my cock. She sucked hard on the head and pulled on her hair, biting my lower lip, trying my hardest not to moan. She looked up at me, and making eye contact just pushed me over the edge. My cock exploded, shooting a hot load into Jenni's mouth.
Jenni closed her eyes and pulled away from my cock, almost grimacing as she swallowed my cum. She let out a little shiver before smiling at me. "That was fun! That was such a big load, but I liked it."
I sighed as I laid back in the hotel bed, surrounded by blankets and pillows. "Thank you! That was amazing. I don't know what I expected, but that I exceeded it," I told Jenni happily, grabbing her wrist and gently pulling her toward me. I gave her a quick peck on the lips before wrapping my arms around her in a hug.
We just laid in bed after that, cuddled up next to each other for a few minutes before I asked her hopefully, "so, what do you want to do next?"
She looked at the clock in the room and sighed, "actually, I think I need to get going soon. I don't want mom to get suspicious."
"Yeah, yeah, yeah," I reluctantly agreed.
We didn't leave immediately. We spent a few more minutes cuddling and kissing, but eventually I summoned the energy to drag myself out of bed and get dressed again. I gave Jenni one last big kiss as we left the room before deciding that I should keep my hands to myself while we're out in public.
Our drive back to the mall was uneventful, and I reassured her multiple times that she looked just like when I had picked her up and nobody would notice anything was different. Eventually, we got back to the mall and I let her out of the car. I tried my best not to stare as she walked away.
I wasn't sure if I would see her again. What I was sure of was that I needed to get back on that website. It was fun when I was getting sexy pictures from teenage girl, but getting one of them for real was beyond my wildest dreams. It wasn't the best blowjob I'd ever gotten, and we didn't even have sex, but something about the excitement and thrill of it was unlike anything I had experienced. I wanted more, and I was more confident than ever that I could get more.
