[FM] Losing my virginity to a redditor

Yup. Just as the title says. I did indeed lose my virginity to a guy who sent me a PM. Now a lot of people have asked me why I decided to lose it with a guy off of the internet. It’s really quite simple…the boys at my school don’t show me much interest (not to pity myself but it is the truth) and I’ve always been into older men, so I thought I would give it a shot. Now that we have gotten that out of the way, I’ll let you guys know about what your actually here for.

I put out two ads on reddit so see if any guys in the Chicagoland area would be interested in taking my virginity. As you can assume, I got a shit ton of responses…on both of them. I got close to 200 on each. The first time around, I got a response from a guy I really liked. He seemed really interested in meeting me and teaching me what to do; since it was my first time. We made plans to meet and everything but I had to cancel because something came up (very last minute plans that I was not expecting). I haven’t heard from him since. So he was a bust. After that failure I put out another (angrier) ad. No one really stood out to me until this guy (we’ll call him M) came along. I asked for some specific things that I wanted the PM’s to have in them. He gave me all of that and then some! He sounded really cool and smart and didn’t hit me with some stupid one liner about how he wanted my “hot teen pussy”. He was different and I like that. M also linked a pic of himself and I found him to be very attractive. He had this very sophisticated, gentleman look about him. I mean he is 38. We started making plans that day.

He told me he comes to Chicago every other week for work, so staying in a nice hotel in the city would almost me guaranteed. That idea was verrry appealing to me. And no, before anyone jumps to conclusions, I’m not using him to stay in nice hotels. I literally just want to get fucked and a nice hotel really adds to that experience. M and I were talking for about 1 week before we hooked up. That week really gave both of us time to talk about our turn ons and what we wanted to do with each other. It also built up a lot of anticipation.

Once the day came for me to finally get fucked, I was super nervous. Even though we had talked about it, I still wasn’t sure about what to expect. M got me an Uber at around 6 pm, and I was on my way. I got to the hotel and it was nice. Not too flashy but not shit. His room was on the third floor and the entire elevator ride I was texting my friends my location so they made sure I wouldn’t get murderd. Walking down the hallway I was shaking. I really didn’t know what to expect and I really hoped he looked like what he said he would in his pictures. Once I got to the door I was nervous as hell but ready for this happen. I knocked twice and he answered.

I was very happy with what I saw! He was even cuter in person. We said our hellos and talked for a little bit. Just smalltalk. He seemed nice and not like a psychopath. After we talked for a little bit he forcefully pressed his lips onto mine. I was wearing some leggings with thigh highs and no panties underneath and a shirt with almost all the buttons undone with a cute bralette under. As we were kissing, I undid my shirt. He noticed and starting groping my tits. M then started kissing down my body and took of my leggings. He loved what he saw underneath. While his hands were on my tits, his mouth was on my soaking pussy. He spread my lips a little and just went to town. Lapping up my wetness with his tongue and flicking my little clit. He was looking into my eyes the entire time. I was moaning pretty loudly at this point, it honestly felt amazing. After eating my pussy for a little while, he rolled me onto my tummy and got on top of me. I noticed pretty quickly that he had a thing about biting and sucking on my ears and neck. He loved to whisper in my ear what a good girl I was while simultaneously sucking my earlobe. M starting moving down my body with kisses and bites. He eventually got to my ass. He spread my ass cheeks with his big hands and started eating my ass. Licking around my asshole and occasionally putting the tip of his tongue inside. This was something I had never felt before so it got me grinding my ass into his face and begging for more. Moving his face down from my ass he would lick my pussy again. Sucking on my clit while fingering me hard. He went back and fourth like that for a good five minutes before coming back up to my neck and biting it. M also loved yanking my hair back and whispering in my ear. He slowly got off of me and took his cloths off. I could see in his eyes how much he wanted my mouth on his cock. He got on his back and I rolled over so my moth was right in front of his cock. I took it in my mouth and he already had his hands on the back of my head. Forcing my head down onto his thick cock. My throat would expand around his dick and go super deep. I gagged a decent amount. He would let me breath for about half a second before thrusting back into my throat. After doing that for 5 minutes he yanked me by the hair and brought me to his lips. After sucking his cock so hard I had a lot of spit coming out of my mouth and we made out with it going between each other’s mouths.

Flipping me onto my back and putting my legs on his shoulders he thrust into me. Going nice and slow at first and then going super hard and pounding me. There was no in between. After cumming from him annihilating my pussy he flipped me back over on my back so my head was hanging off the side of the bed. He wanted me to deepthroat his cock again. This position intimidated the hell out of me because I knew it would make me take is cock super deep into my throat. M slowly put his cock into my throat all the while I was gagging like crazy. Wish I could say I was a master deepthroater but I’m just not. He did that for a few minutes but I was having a lot of trouble with it and vomited on his cock a little. Not my proudest moment. We took a little water break after that and he got me a towel to clean my face with.

With us both deciding that I probably shouldn’t suck his cock again he decided to fuck me again. This time he made me guide his cock into my ass. Anal really wasnt a huge deal for me since I have been stretching my ass for a few months now. He put some lube on his cock and went crazy. He was pounding me like no tomorrow and I was loving it. It seriously felt amazing. I brought some of my toys along so we could add to the fun, so M decided to get out my dildo. I was already soaking wet so there was no need to even put lube on it. He was pounding both my ass and my pussy at the same time. This was probably my favorite part. Having both a cock in my ass and pussy was stuff I only saw in porn and I am happy to report it feels fantastic. To add even more to the fun he got out the Magic Wand he got me and put it on my swollen clit. This sent me into overdrive and I came twice from all that stimulation. My pussy and ass were pulsating like crazy and that made his cock twitch and he dumped a huge load into my ass. I was shaking like crazy and pretty overwhelmed with everything that just happened over the two hours we were fucking.

I laid on his chest for 10 min in silence. It was super nice to just be calm after that intense fuck session. I got up and walked to the bathroom and cleaned myself off (not before I scooped some of the cum out of my asshole and tasted it, it was great). M and I ended up talking for about an hour after that. We got along great and got to know eachother a fair amount. After all that he ordered me an Uber and I was on my way (he gave me the magic wand and I have had fantastic orgasms with that thing since). When I was walking out of the hotel I could feel his cum leaking out of my ass a little bit too.

We’re definitely gonna do this again because he kind of wanted this to turn into a fwb situation. So I will probably end up writing more stories about my sexual experiences with him and other guys too! Hope everyone enjoyed the story :)

PSA: don’t expect him to comment because he wants this to stay as private as possible. We also didn’t take pictures because in the heat of the moment I wasn’t concerned with snapping a few pics.

Source: reddit.com/r/gonewildstories/comments/7e5kt2/fm_losing_my_virginity_to_a_redditor