Taking the girl of my dreams from my best friend and losing my virginity to her [MF]

This is my first post here, but I wanted to contribute something instead of just reading. This is going to be the story of how I lost my virginity to the girl we’ll call “Kaylee” for anonymity. This was in high school (everyone in this story was 18 at the time.) Fast forward through the first few paragraphs if you’re not into the backstory thing.

So me, in high-school I was the type of kid that got along with everyone. I didn’t believe in “cliques” so if you were cool with me, I was cool with you. I was heavily involved in my schools JROTC program and my entire world revolved around my truck. My Ford Ranger was the most badass thing in the world to me and me only, haha. I knew that I wanted to be a police officer right out of high school so I didn’t really do the typical high-school parties and stuff because I was too scared to get in trouble and mess things up for myself.

I’ll describe Kaylee. Kaylee was about 5’09”, which is taller than girls that I prefer being that I myself am only about 5’11”. Kaylee had great tits. They were DDD’s if I remember correctly. She was also extremely thick for a white girl. She had the ass that would make you double-take as she walked by and wonder how she managed to put on those bootcut jeans with the rhinestones on the back pockets. Her thighs were even thicker, just the kind you want wrapped around your head I guess. She also had a little belly on her, which drove me absolutely wild. Her hair was almost platinum blonde, and Kaylee always had the best perfume. Kaylee’s personality was intoxicating. She had gone through some childhood trauma in the past but managed to fight her way through it and find joy in a lot of things. She was absolutely hilarious and I basically fell in love with her immediately. The bad thing was, however, Kaylee went to another school a couple of towns over so I really only saw her on the weekends since I worked every day during the week after school.

Onwards. Kaylee dated this guy (I won’t even mention his name) that I was not a fan of whatsoever. He treated Kaylee (and everyone else for that matter) like absolute shit. Just a terrible guy. Kaylee would later go on to tell me that he was pretty abusive to her and I had no reason to disbelieve it. Halfway through my senior year, they broke up for good. I was ecstatic. Unfortunately, my best friend (We’ll call him Weston) beat me to the punch. They started talking and eventually began a relationship. When I mean relationship, I mean he’d pick her up and drive around for an hour or two and drop her off. Clearly, this was not working for her because she thankfully broke up with him after about a month. I waited a couple weeks to talk to her, because I still had to manage a friendship with Weston and not seem like I just wanted to be the next guy in line for her.

I ended up commenting on one of her social media posts that I’d later jack off to because her ass was about to bust the seams of her jeans. She messaged me later that night and we exchanged phone numbers. I stayed up all night talking to her and eventually asked her on a date that weekend. I picked her up in my truck, brought her flowers, met her folks, and off we went. We had such a good time and I really didn’t want it to end.

Kaylee knew that I was a virgin, and she was not. She always told me she thought it was hot, and would always tease me that she wanted to take my v-card. I wanted her to snatch it away from me with a vengeance. A couple weeks into our newfound relationship, she sent me a picture of her ass in a G-string. I was at work, and had to excuse myself to go in the bathroom to stroke my cock. I told her how hard she made me and begged her to send me another one. This time, however, she sent me a video of her playing with her pussy. Side note, Kaylee’s pussy was stupid fat. Like the kind you have to spread it just to find her honey hole. And I loved it. She had big beautiful pussy lips and the tightest, cleanest asshole I had ever seen. No pornstar I’d ever watched could match what she had in her pants.

The following weekend I was at her house later than I should’ve been. We were laying in her bed and I was wearing gym shorts and a shirt, she was wearing one of my shirts and a pair of panties. Out of nowhere, she asked if I had ever had my cock sucked. I thought about it for a second, thought about lying and saying yes, but eventually the word “No” fell from my mouth. Like clockwork, Kaylee got on her knees and put her hair in a ponytail. I was so fucking nervous. She pulled my gym shorts around my ankles and whipped out my cock. Now I’m not the biggest, about 5″ soft and decently thick. Kaylee immediately started sucking on the head of my cock, looking me in the eye as my cock slid down her throat. I was in pure heaven. The warmth I felt flowing through my body as her head bobbed up and down on my rock hard cock was mesmerizing. About 5 minutes into it, I felt my balls began to churn and I warned Kaylee that I was going to cum soon.

She stopped sucking, started stroking, and asked “Are you going to cum in my mouth, daddy?” and I could’ve blown my load right there (P.S., this is how I found out I had a daddy kink) and Kaylee went back to sucking. The head of my cock was hitting the back of her throat each time her head went down. I felt my toes curl automatically and I rammed Kaylee’s head down on my cock as far as it would go. My cock shot rope after rope of hot cum down her throat for a good 10-15 seconds. She swallowed every drop that I gave her and wiped her mouth before she sat on my lap and made out with me.

The thing about Kaylee, is that she was always horny. Kaylee’s pussy was very sensitive for reasons that I won’t go into detail about out of respect to her, but she could cum if you rubbed her pussy over her pants. Every touch of her flower shot shivers up her spine and that fact alone made it almost impossible to keep my hands away from her warm mound. Anyway, Kaylee told me she was going to teach me how to eat pussy. Lucky for her, I had some experience eating my ex’s pussy and I thought I was pretty good at it. Without a second thought, Kaylee got on all 4’s on her bed and started grinding. I made my way behind her, and pulled her neon green G-string to her knees. I smacked her fat ass a couple times, each time she moaned into her pillow since her grandparents were sleeping on the other side of the house. By this time, I was hard as fuck and ready to go again (gotta love being 18). I didn’t think Kaylee was ready for it, although I was, so I didn’t try and fuck her.

Without hesitation I immediately plunged my tongue into Kaylee’s asshole. Her asshole was so tight, but I grabbed her waist and pushed it as far into her as I could. Kaylee was moaning even louder now, to the point where I thought I should stop before we got caught. Who was I thinking? I wouldn’t miss this opportunity for the world. I started rubbing Kaylee’s clit while I worked my tongue in her ass and she reached back, grabbed my wrist, and had her first orgasm in my mouth. Feeling her asshole clench and release against my tongue almost made me cum again. Finally, I moved down to Kaylee’s fat pussy that had formed a wet spot on the blanket she was perched on. I started licking her clit to the point where she started shaking. I sucked, nibbled, and licked her clit until she started shaking. When I decided that wasn’t enough, I slipped a finger in her pussy and I was absolutely amazed at how tight she was. I knew she had been kind of a whore before me, so I kind of figured she’d be well used.

Boy, was I wrong. I felt Kaylee get ready to cum again, so I started reaching for her g-spot with my index finger, sucking on her clit with my mouth, and I had shoved my thumb into her asshole. (Thank you porn for teaching me that.) and that sent her over the edge. She came hard as fuck all over me. I thought she had squirted, but it ended up being the mixture of my spit and her pussy juices flowing down her legs. Kaylee was out of breath and pulled me up to her mouth so she could taste herself. We laid in bed together naked, exploring each other’s bodies for about an hour until I realized it was 3 in the morning and I had to be at school in 4 hours.

While I was in school the rest of the week, Kaylee would send me random pictures of her tits, pussy, or ass. She would tell me how bad she wanted my fat cock in her mouth again and told me how wet she was thinking about me eating her pussy again. I had made plans to take Kaylee to a truck meet (Southern boy in high school, give me a break) that Saturday. After confirming, Kaylee told me to buy some condoms because she wanted to ride my cock. I had never bought condoms before so I was super nervous. I remembered how great her pussy was and manned up, went to Walmart and bought a 4 pack because you never know.

Saturday came and I picked her up at 4. We drove to the truck meet and had a great time. We managed to snag a few beers from some people we met, so we were pretty buzzed and she started rubbing her ass against my cock over my shorts. She bent over to pick something up and caught me staring at her red lace thong over her designer jeans. She knew I had a panty fetish and she knew exactly what she was doing. I couldn’t wait to get her home.

During the hour drive home, I couldn’t keep my hands off of Kaylee. I kept rubbing her thigh, occasionally rubbing her pussy over top of her pants because remember I told you guys she loved that? Out of nowhere, Kaylee takes her pants to her knees and starts rubbing her clit. She had put her back to my passenger door and was now facing me with her pussy in plain view. I could see how wet she was, and if I couldn’t, Kaylee slid a finger inside of her cunt and put it in my mouth. I never knew a pussy could taste so sweet. Kaylee fingered her pussy to orgasm number one that night in my truck. I was so mesmerized by what she was doing that I hadn’t even noticed that I was bulging out of my pants again.

Apparently she did, because she undid my belt and my shorts to relieve some pressure. Kaylee started stroking my cock through my underwear, which caused me throw my head back and moan for her. Kaylee told me to pull them down, at which point I happily obliged. Kaylee took my hard cock in her mouth once again. She bobbed her head up and down just like the good girl that she was. I could see the reflection of her pussy and asshole staring back at me threw the passenger window, which made me cum in no time. Kaylee loved my cum in her mouth almost as much as I loved busting my nut in her mouth. She took her panties completely off, hung them from my rearview mirror, and told me I had to leave them there. I didn’t mind that whatsoever.

Finally. We made it to her house. It was about 11:30 at night so her folks were asleep. It was ON the second we pulled in her driveway. I shoved her up against the side of my truck and plunged my hand down into her pants and felt what was left of her cum on her pussy lips. I looked her in the eye as I pulled my hand from her pants and put my finger back in my mouth. Her legs became weak at the sight of this and she moaned ever so slightly. She grabbed me by the wrist and dragged me to her room.

Once we got to her room, it was like a movie. We were too busy pushing our tongue’s into each other’s mouths to realize how much noise we were making, pushing shit off of her dresser and knocking other stuff over. To this day, I don’t know how either of her parents didn’t wake up. By this point, we had basically stripped each other and were standing in her room completely naked. I grabbed Kaylee’s fat ass and lifted her onto the dresser. We made out for a couple more minutes, accompanied by her stroking my cock and me rubbing her pussy. Kaylee looked me in my eye this time, and said “I want you to put your big dick in my pussy, daddy.” Fuck. I moaned. My knees got weak. My heart was beating faster than it ever had before.

I reached into the pocket of my shorts that were now on the floor and pulled out a condom. I was in such a rush to put it on that it broke. Fuck me, right? I had left the other 3 condoms in my truck on accident. I told Kaylee this, and reached for my keys to go grab the other ones. Kaylee grabbed my wrist and told me that she didn’t want me to wear a condom. Kaylee said “You’ve cum in my mouth, I want you to cum in my pussy, baby.” Her voice was so soft. Common sense left my head immediately and I said fuck it. She grabbed my cock and started running it up and down her pussy lips to tease me and so I could feel how wet she was for me. She was kissing my neck and asking me if I liked it. She asked me if I was ready for her pussy. I told her yes, but in my head I knew I wasn’t.

Kaylee stroked my cock a couple times to spread her pussy juices on it and guided it into the entrance of her soaking wet pussy. Again, I was a virgin 30 seconds ago. Everything I knew to this point was from porn. Kaylee told me to fuck her slow to get used to it. I thrusted my cock in and out of her hole for 2-3 minutes until I felt I had gotten the hang of it. Kaylee must have agreed, because she wrapped her legs around my waist and told me to fuck her. No other instructions, just “Fuck me.” I sawed in and out of her pussy like my life depended on it for another few minutes. Kaylee was reaching down and rubbing her clit with one hand and running the other hand down my chest, pinching my nipples as I fucked her pussy. She had to bite her tongue to keep herself from moaning and waking everyone up. I heard her whimper each time I thrusted into her.

Kaylee knew that I was going to cum soon and reminded me that she wanted it in her pussy. I started sucking on Kaylee’s tits and got that feeling in my balls again. I pumped a few more times and before I knew it I came harder than I EVER have before. I knew there was so much cum filling Kaylee’s pussy. I couldn’t bring myself to pull out of her for another minute or two, which was fine because we both had to catch our breath anyway. Kaylee told me that I made her cum, but she wasn’t done with me.

Kaylee made me lay on her bed and we 69’d for a few minutes until I was hard again. Kaylee got to her feet and started to ride my cock in reverse cowgirl. Watching her fat ass clap for me was fucking ecstasy in my veins. I have always been an “ass guy” so there was nothing I loved more than her bouncing up and down on my cock. Her pussy juice was running down my cock each time she bounced on me. I reached up and put a finger in her asshole while she rode me, and a minute later she told me to put another one in there. This time, I felt Kaylee’s pussy pulsate and contract on my cock and she suddenly stopped riding. She threw her head back and put her hand over her mouth to keep her from moaning. I knew she had cum, and she came hard. Since I had cum twice in the last hour, I still had a few more minutes of fucking in me.

Kaylee dropped to her knees and swallowed my cock for a minute or two because she told me she wanted to taste her pussy. She bent over her bed, reached back and rubbed her spit into her asshole. Kaylee told me that I was going to fuck her in the ass, and I obeyed like a good boy. I grabbed hold of my cock and pushed the head of it into her waiting asshole. Kaylee squealed in pain but told me not to stop. Finally, I was over the edge and my entire cock was in her fucking asshole. I could not believe how tight it was. I stroked her ass for about 3 minutes and knew that my time was running short. I felt my balls churn stronger than I ever have, probably because of her moaning “Fuck my tight ass, daddy. I need your fat cock in my fucking asshole.” I asked Kaylee if she wanted me to cum in her ass, but she denied.

I told her I was going to nut, and she pulled herself away from my cock, turned around, and licked my dick from my balls to the head. She swallowed my cock again, this time taking it down her throat while cupping my balls. I came for the third time that night in her mouth and I almost fell to the ground. I couldn’t believe that Kaylee took my cock in her mouth after it had been in her asshole.

We took a shower to clean ourselves up and I climbed into bed with her. We cuddled, talked about our future and where we would go from there. Kaylee and I had sex just like that almost every day for the remainder of our relationship, which would ultimately last about 6 more months. Kaylee moved to Alabama and has since had a kid, which is no surprise to me. I haven’t talked to her since 2016.

I really hope you guys liked my story. Sorry it was so long, but I wanted to include every detail to paint the picture for you guys.

Source: reddit.com/r/gonewildstories/comments/rlzyzh/taking_the_girl_of_my_dreams_from_my_best_friend