Let my high school crush take my anal virginity! [FM]

Hi, friends :) I’ve been active in this community for a while, I’ve even posted once or twice but ultimately took down my posts for unknown reasons. So hello!

I’m 22, 5’2, cute and curvy, with a thick ass and some big ol titties :) I’ve got long red hair and freckles all over! My names Amelia ? hope that helps with the visual :)

This requires some backstory: I lived in Colorado for a spell during my sophomore year of high school. I met this cute guy named Aaron in between classes and we exchanged phone numbers during the year. He would call me and we would stay up late talking about anything and everything, I loved talking to him. We quickly figured out he lived about a mile away from me in the neighborhood right next to mine. One night, he called me and asked me to come over, and that quickly turned into me going over there once or twice a week in the middle of the night.

Aaron was the first guy I ever “did stuff” with. He is tall, black and Asian, and has a thick cock that I love. He was the first guy to ever finger me, go down on me, and the first guy I ever let get close to fucking me. I also practiced on him, giving him blowjobs and handjobs all the time. I had a gigantic crush on him and relished seeing him when I did. I spent my last night in CO with him just anxious about moving again, cuddling and making out and getting very close to giving him my virginity.

We kept in touch as I moved away, and I’d send him an occasional nude from time to time over the years. It had been about 4 years since I’d seen him when I came back to CO to meet up with some friends. I found time to see him and we smoked a bowl together and ended up having sex. It wasn’t anything GWS worthy, but it definitely had been something we both wanted for years and was fulfilling to finally fuck him after years of fantasy.

About a year ago, Aaron and I stopped talking because I straight up was just being a bitch. I had my reasons back then, but I don’t see them now. So about a month ago, I messaged him and apologized. He was mad that I’d reached out and I just basically said thank you for responding at least, couldn’t be mad that he didn’t want me back in his life. But a day goes by and he messaged me back again, and it just turned into us being cool again, which I was so grateful for. Aaron means a lot to me, I was grateful he had seen that I was being a dumbass and was forgiving me for it.

We started getting flirtier over the days and I ended up sending him some videos I’d taking of myself using my new suction dildo, and he went crazy for that! He had always asked me for videos and I had never done so for him. I wasn’t in tune with my body like I am now! So anyway, he starts asking me when I’m coming back out to CO and I honestly told him I didn’t have a reason to anytime soon. He surprised me and asked me “what if I flew you out here?” And after some debate, we picked a date about 2 weeks out and he booked the flight. It was going to be a nice break from my job and I get to be fucked by this guy I still harbor feelings for? I’m down to clown.

Prior to my trip, Aaron and I had talked about kinks and who we’d slept with since seeing each other, swapping stories back and forth. I told him how I’d been able to make myself squirt on occasion and I knew he took interest in that, never having made a girl squirt before. He later asked me if I’d ever had anal sex, to which I said no. I had tried with one of my boyfriends but with spit as our only lubricant, we didn’t get very far. But I told him I’d be up for it with him if he wanted to try! I made it clear it most likely wouldn’t happen on that trip but could definitely happen another time! I wanted to prep and get some plugs and do some research, prep for the event. Plus, I hadn’t given him my actual virginity back in the day and I told him I owed him one, and I intended on letting him fuck my ass eventually.

I got there on a weekday afternoon and spent the afternoon by myself in downtown Denver. It was a dream. I got to shop, got on one of those scooters and explored the town, and drank some good drinks as I waited for Aaron to finish working. He got off around 6 so I met up with him and he took me back to his place. We got takeout, tequila and some weed and we were all set for a relaxing evening. We were sitting around on his couch, a few shots deep and getting pretty buzzed when he finally made his move. I was so nervous with him that I was hopeful that he’d make the first move so I didn’t have to, and thank fuck he finally did!

He was walking back to me from the kitchen and I was laying on my side on his sectional. He looked at me and his gaze darkened as his eyes dropped down to my ass. He slapped me firmly on my ass and said “is that ass still fat?” And I laughed and said “well yeahhh” as he leaned over and kissed me. His tongue swirled with mine as I remembered how much I loved making out with him; Aaron is a phenomenal kisser, probably definitely number one on my list. We were making out for a minute when he leaned back and helped me take my shirt and bra off. As quickly as my shirt was off, his tongue was swirling circles around my nipples, biting and sucking on them as he cupped them together with his hands.

His lips captured mine again as I decided it was his turn to feel as good as he was making me feel. My hands found their way from his neck to his cock, already hard for me in his joggers. I slipped down to the floor and took his pants down with me. I wasted no time and started sucking his dick with a passion, the tequila helping me turn it up an extra notch and making it even sloppier than normal. I kissed and sucked on his dick, tracing every inch with my lips and tongue, guiding him to the back of my throat, stroking him with my hand as I sucked his balls into my mouth, one at a time and then both together. I love sucking dick and love men who let me do what I want, and Aaron was sitting back and enjoying the show while moaning and groaning his appreciation for my talents. He thrusted into my mouth and guided himself all the way to the back of my throat while letting out a string of curses as I moaned against his shaft as he went deeper into my throat. It was truly so fucking hot.

After a few more glorious moments, he had me lie down on my back as he removed my pants for me, entering me in one swift motion, filling me to the brim. He fucked me like this for a while, choking me and letting me suckle on his fingers as he fucked me hard and fast. He pulled out and inserted 2 fingers in me, roughly fucking me with his hand. He looks down at me and says “you’re either going to squirt for me or let me fuck your ass.” It wasn’t a question— it was a statement of fact, which made me even wetter than I already was. Right after he said that, his phone starts blowing up and he actually had to take it— he was on call with his work and had to resolve something that room a bit longer than expected. I put on my shirt and watched some tv as I waited for him to wrap up. He left his apartment for a brief minute and came back and joined me on the couch.

“Come get a massage.” He turned me on my stomach and pulled my shirt up as he started fingering me again, this time more gently. He brought my wetness up to my ass and started fingering my asshole with my juices as his lube. He worked up the speed and kept edging me closer to an orgasm, never giving me what I ultimately needed and craved. He kept going and finally said “please let me just try” and I caved and told him to go get the lube, already knowing he was referring to fucking my ass.

He came back a moment later, dick already out of its confines and getting lubed up and ready to go. He got on top of me and started pushing the tip in. I inhaled sharply, not used to the pain. “Relax your asshole, just relax” he kept repeating to me. I was trying to, but found it hard to focus. I started exhaling deeply and found that really helped in relaxing my ass, so I kept doing that as he thrusted in, adding more lube as needed. I felt him add some more inches and held my breath as he started to pull out before pushing back in to me, slowly. He got to this point where i inhaled sharply and asked him to add more lube before he kept going. He complied and it honestly felt a lot better. I exclaimed and said “that’s not even half is it?” expecting the worst. He said “that’s actually the whole thing.” I felt my chest swell with pride and laughed a little bit in disbelief. His 7 inch dick was inside of my ass. I got turned on when I realized this, and started talking dirty to him.

“Do you like fucking my ass?” He picked up the pace as he moaned. “Does it turn you in knowing you’re the only guy to ever fuck my ass?” again the pace picked up. “I love feeling that big dick in my ass. Do you want to cum in my ass, make it yours?” Another moan as he grabbed my hair, railing my ass now. “Ohhh take this ass, it’s all fucking yours, no one else has fucked this ass, yessss Aaron fuck my asssss.” He came in my ass shortly after, leaving me on the couch to catch my breath as he cleaned himself up.

We laughed a few minutes later about the situation and thanked our friend tequila for lowering our inhibitions. We fell asleep and he took me to the airport the next morning. We’re already planning our next trip to see one another next month, and I can’t wait to see him again and see what else we can explore with one another! 10/10 experience, it was exactly what I needed.

Thanks for reading. ♥️

Source: reddit.com/r/gonewildstories/comments/i5ocnt/let_my_high_school_crush_take_my_anal_virginity_fm