Finally [F]ucking [M]y High School Crush

I know some people are only interested in the sex, so if thats you, skip to **THE SEX STARTS HERE**, for everyone else, enjoy

My senior year of high school I developed a crush on Ally. Ally was your stereotypical all American girl; 5’4, blonde hair, blue eyes, nice body, outgoing and popular. The kind of girl everyone in the senior class knew. I, on the other hand, was the epitome of average in high school. I wasn’t ugly or fat or anti-social, but we were definitely in different social circles. Truth be told, she didn’t even know who I was (I went to a really big high school).

Flash forward to last week, I’m 24 now, and living in my hometown after graduating college. I’d long forgotten of my high school crush and was content with my life. I had matured a lot since high school; I’d hit the gym, grew a beard and bought a nice car. In essence, I had the prototypical millennial ‘glow-up’. I felt my phone vibrate in my pocket and checked it, seeing I got a notification every guy loves “You’ve got a new match!” – Tinder. Cool. I open it up and see she’s already messaged me. A great start no doubt. I open it up and look at her profile, and it says the words every guy on tinder wants to see “here for a good time, not a long time”. Even better, I think, she’s messaged me first and is DTF, ya boy is getting laid AND HOLY SHIT ITS ALLY! I didn’t recognize her at first as her hair was a little darker then I remembered it, and she had gained a little weight since high school. Where as in high school she was the stereotypical thin cheerleader, she now had fully grown into her body and was what is best described as “slim-thicc”. I don’t know about you, dear reader, but slim-thicc girls are my kryptonite. To say I was awestruck, happy and excited is an understatement.

We started texting each other and I wasn’t surprised to learn that she didn’t know me in high school. I really hate when people are the same people they were in high school, and Ally seemed to have also really grown and matured since then. She seemed even a little shy talking to me, but overall our conversation was fun and flirty. I finally grew a little bold and actually asked her directly if she was looking for a FWB situation. It was bold, but I was a little buzzed and figured fuck it, I have nothing to lose. She replied instantly, sparing me the post risky text regret. She told me that she had just moved back home to go to grad school and wanted exactly that. She explained she was in need of dick due to her stressful school schedule, as I’m sure anyone who’s been to grad school can understand, and she also explained that she really wanted more friends in the area, as all her friends from high school had either moved or just had grown apart. I told her that that was perfect with me, I was in the same boat. Internally I was screaming. I was going to finally have the opportunity to sleep with my high school crush, but I would also get a FWB situation out of it.

We set a time to hang out and met at a local bar to watch the Titans-Patriots game. We were both rooting for the Titans and got wings and beers. The conversation was flowing great and I was genuinely having a great time; theres nothing better when you hang out with someone and it’s as great as you expect it to be. As the game ended we were ecstatic, and we knew we wanted to continue the night. She looked at me with a devilish grin and a twinkle in her eye and said “I ubered here, do you have a condom?”

**SEX STARTS HERE**

I let her know I did, and we walked to my truck, and drove to a side street with no traffic lights and little traffic. There’s nothing sexier than having sex with an old crush for the first time in the back of your truck, but I digress… She unbuttoned my pants and then proceeded to devour my cock in her mouth, smearing her lipstick on my shaft. It was heavenly and I felt like I could cum just at the thought of all that was happening. I pushed her off and began undressing her, revealing the most perfect pair of 34DD’s with tiny hard nipples. I began to play with them and bit her softly, causing her to moan loudly and caused a noticeable amount of heat to radiate from the crotch of her yoga pants. I slipped my finger down her panties and felt the absolute smoothest and tightest pussy I’ve ever felt. I probably fingered her for 30 seconds before she took her pants all the way off, slipped a condom on me and lined herself up to take me cowgirl.

Even though she was soaking wet, it took a minute to get inside her, but when I did, both of us moaned in pleasure. She felt absolutely fantastic, squeezing my dick perfectly. After a few long, deep strokes and getting acquainted with each other, she started riding me. It was pure heaven, and I couldn’t resist choking her with a free hand. She seemed to be really enjoying it and rode me harder, shaking my truck like she was trying to break the suspension. I don’t know how long we went before she looked me in my eyes and asked to take me missionary. How could I say no to an offer like that? I flipped her on her back and slowly entered her, making sure to tease her before I began pounding her like my life depended on it. After a few minutes I felt myself building and eventually exploded into the condom, her legs wrapped around me. She kissed me as I slowly exited her, smiling, happy with what she had just done. I offered to help her finish, however she said not to worry about it tonight, she was getting a little nervous about being in my truck. As I drove her home we continued chatting like we were old friends, laughing and joking and singing badly to Wild Thoughts by DJ Khaled. As I dropped her off, she hugged me tight and told me that she’d see me next week and was looking forward to me making her squirm.

Overall, it went about as great as it could have, and I’m extremely happy to have (re)connected? with Ally. If anyone is interested, I can write about how next week goes.

Source: reddit.com/r/gonewildstories/comments/ekjpu1/finally_fucking_my_high_school_crush