My experience sleeping with my High School crush [MF].

First off I want to say that I’ve never wrote any of my stories before, so I want to apologize for this being long. I’m going to be as detailed as possible so bare with me. This is the story of me sleeping with my crush. We will call her C, and I’ll be D.

I’ll start with the description and background story. In High School I wasn’t cool. I didn’t think I was. I dressed pretty nice and every year I’d hear rumors about which girl might like me, but I was basically oblivious to “being cute”. I’m 5’9, Strawberry Blonde hair, blue eyes. Back then I was super skinny. My crush seemingly has stayed the exact same. 5’0, right at about 100lbs. The epitome of petite. I’ve always liked curves on women, but C has always been my ideal. Huge brown eyes that have that make you want to buy her a puppy. Brown hair. The perfect “Girl Next Door” look.

C dated one of my best friends early in High School so she was off limits back then as a sign of respect to my buddy. That never stopped me from utilizing her as my masturbation inspiration for years. She went off to college, I went off to the Army. When I left my hometown I basically disappeared. I hated where I grew up because I never belonged. So I cut off most ties with my hometown, and the people in it.

Fast forward ten years. I’m out of the Army after serving 5 years 8 months and 13 days, living in beautiful Savannah, GA, and not super skinny anymore. I’m about 185lbs of dad bod muscle with a big red beard. I still dress nice, and became semi-aware that I’m relatively attractive. I had just gotten out of a relationship and surprisingly wasn’t going through my normal “man-whore” cycle of sleeping around with the plethora of college girls with daddy issues. I get a Facebook request from C. I hadn’t kept any tabs on her (or anyone really for that matter…had a new life), so checking her pictures I was pleasantly surprised to see she was literally exactly how I remembered her. Gorgeous, with a hint of natural submission, coupled with more life experience. She messaged me first.

C: “D! Wow! How have you been?? You live in Savannah, GA? That’s crazy. I see you escaped too. I live in Charleston now.”

Casual conversation/chatting ensued, with no flirting. I believe I held back out of reverence. We did our normal catching up, before the breakthrough happened.

C: “Well it sounds like you’re doing great. And looking really great! It’s super cool that you live close. We need to get dinner if we are ever in each other’s cities.”

D: *shocked* “Thank you. You look gorgeous as always. I’m actually planning on being up there for business in a week. I’ll be flying into the city before driving back to Savannah. We could get dinner before I head back yea?”

C: “Definitely! And what do you mean as always?”

D: “Come on. You know I had a huge crush on you. Like huge. I just never acted because I was a dork and also you previously dated *Friend*.”

C: “What?!? No. I had the crush on you. You were that quiet guy who had no idea they were attractive.”

I had heard that before, that I had no idea I was attractive. So the ground had been set. Numbers were exchanged. Minor flirting during my business trip but nothing in depth. Mutual attraction. I go on my trip and end the trip flying into Charleston. I sent her a text, and she met me at a restaurant. Dinner was nice. She showed up wearing a cute little sun dress that accented her petite physical features. Maybe I was oblivious to it in High School but C had a gorgeous ass that made the dress poke out.

We chatted and it was getting late, so I fully intended to get headed home. Charleston is about 2 hours away so I couldn’t get any drinks. She then shot that idea down, stating that her roommate was gone on vacation and she had plenty of room for me. It didn’t take long to mull that thought over, so I accepted as long as it wasn’t a inconvenience. Off we go…

Her apartment was small and cute. Perfect for a teacher with a roommate. We share a glass of wine, which was in abundance because apparently teachers drink a shit ton of wine. More harmless flirting, before we decide to call it a night. I didn’t want to assume I was sleeping with her so I told her the couch would be fine. She helped set it up for me. We say goodnight and she heads off to bed. As I’m kicking back she comes out in an oversized t-shirt and my heart skipped a beat. I’m going to skip the sappy emotions that were going on in me but I can say that the High School inner me was giving Now-Me a huge high-five. She had this look in her eyes. C walks out to the couch as I sit up, without the chance to put my shirt on. She comes over to me and straddles me without saying a word. She looks at me and says “I couldn’t go to bed without kissing you.” Before she comes in for a gentle kiss. Our lips meet, followed by parting way for our tongues to gently slide off of each other. I pause to tell her “You have no idea how long I’ve wanted to do that but didn’t.”

We go back to kissing deeply. As things progressed, my dominance took over from the reserved reverence. I picked her up. And carried her down the hall to her room. She had candles lit (she totally had this planned. Smart girl.) and bed still made. I placed her down on the bed and climbed on top of her. My cock (which is a thick 6 inches) was throbbing and pressing through my shorts. I feel her grinding against it, as I look down to watch and see she’s wearing a very small thong. Going back to kissing her and moving down to her neck. I start to pull up her oversized shirt, and run my hands over her perfectly perky B-cup breasts. She lets out a rather loud moan which drove me crazy, as it was a precursor to her being way more vocal and aggressive in bed than ever anticipated. I slowly kiss down her body before coming to her hip bones. I kiss and nibble on it moving inward. At this point she was arching her back and trying to grind into me. I pull her panties to the side as I slowly run my tongue over her clit. The immediate reaction created a primal instinct in me to continue. I slid two fingers in her and motioned the “come here” technique. With her grinding into it and me alternating from flicking my tongue to sucking gently on her clit, she orgasmed hard. Her moaning followed by “oh fuck. I’m cumming. Please. Come here now.” I raise myself up as she bends forward. Taking my cock out in one swift movement. I assist on pulling off my shorts the rest of the way. Her mouth immediately wraps on my cock as she stares up at me with her gorgeous brown eyes. If I have ever been as close to cumming from that alone, than let me tell you. She breaks contact and wraps her little hand around my cock, as she says “mmm. D. This is too big for me to take all the way. I need to help lubricate it.” (Bless her because I’m not TOO BIG). She spits on before stroking it and sucking more. This sloppy style is exactly what I need, but that primal instinct gets the best of me and I pull back. I reach down and pull off her panties and climb fully back on top of her. I tease the lips of her pussy before pressing the head of my throbbing cock into her. I ease in with how tight she is, and let out a sigh as I slide fully inside.

C: “oh. My. God. Fuck me.”

I oblige the request and grab onto her firm ass as I start to thrust into her with acceleration. As I start to vary my motions, her breathing speeds up again.

C: “D. I’m going to cum. Don’t stop. Seriously. Don’t fucking stop.”

I keep the exact pace up as I feel her clinch down and then immediately release. Her contractions push me out, to which she apologizes for. “That is literally the first time that’s ever happened. Oh my god. Let me ride you.”

D: “good. I want to feel you ride me.”

C climbs on-top of me. And immediately lowers herself down. We kiss as I raise my hips up and thrust from the bottom. I grab onto her and start to slam into her. She starts to rock her hips with each of my thrusts, which make for this perfect sexual cohesion. After roughly 20 minutes of varying pace and intensity, mixed with passionate kissing, she looks at me.

C: “D. Please. Cum. Deep. I need to feel you. Fill me up.”

With that one statement she checked off just about everything that was perfect about the entire situation. I continue my thrusting till I start to cum. I feel her tense up as I’m shooting deep inside her, and she’s lets out a very pleased moan. I pull her onto me and kiss her deeply. Followed by cuddling and us both looking at each other. At that exact moment I realized how deep I was about to fall in love.

Now. I could end there but I’m sure the questions would come. We ended up dating for a few months. Had more fun experiences. Got pretty serious and then she broke up with me. Crushed me hard. As much as that hurt I still occasionally look her up on social media to reminisce.

TL;DR : Former high school dork reconnected with High School crush. Had sex.

Source: reddit.com/r/gonewildstories/comments/93h6k7/my_experience_sleeping_with_my_high_school_crush