[M]y [F]irst hookup.

This will be a longer story, but its my first attempt at writing something like this, so I hope its good! Here goes!

My first relationship ever lasted 2 and a half years from 17 to 19. We were eachothers first kiss, lost our virginity to eachother, and were eachothers first bad breakup. It wasn’t a great relationship, but I learned alot about what I like. Mainly that I really, really like sex.

After we split up, and I took some time to myself to heal, I started looking for someone to scratch that itch again. So I downloaded Tinder, Bumble, the usual, and searched. Im a pretty average looking guy, on the more attractive side of average, but average nonetheless. I had a couple dates, some with women I considered way out of my league, but they all ended in basically the same result. Getting ghosted. Even the ones that I felt a real connection with. Needless to say, I was a bit disappointed, and I still hadn’t gotten laid. I was several months in at this point, so I knew some changes had to be made. Instead of going on dates, I decided to just look for a hookup.

Another month goes by, no dice. At this point, I start to think my ex was the only woman I’d ever get to fuck, and almost started to miss her. Almost. So I think, ya know, maybe ill just take a trip out of town, go visit some friends, and clear my mind a bit. I drove 2hr south of where I was living at the time, hung out with some college friends, and got a hotel room. As the night was winding down, I decided to open tinder, and update my account stating I was only in the area for the weekend, to see if thatd up my chances. And I got a hit.

Sierra, as we’ll call her, was a pale skinned, curvy blonde woman a year older than me, with nice features, and only a 10min drive from my hotel. Even better, I was familiar with the area and didn’t even need GPS to get to where she lived. We talked for a couple hours, she was aware of the situation, and was looking for the same thing as me. We both needed to cum.

Now I need to say, I was a very sheltered kid, so while it wasn’t a surprise that I was a horny little bastard, heading to a strangers house at 1am to fuck was way out of my comfort zone. But I proceeded, heart racing, to her front door. She opens, thank God its actually her, and leads me inside holding my hand the whole way. She lives in a nice town home with several other girls for college, and tells me to keep quiet heading in. My mind is going a million miles an hour as we get to her room.

She walks us in, closes the door behind us, and flops on her bed playfully. “So what do you wanna do first?” She asks, smiling at me. She’s got a great smile. I have to stop myself from catching feelings. This isn’t a date. “To be completely honest, ive never done this before….hook up, that is. I’ve had sex before.” (Clearly a master at romantics here) She giggles at me. “You’re so cute. Come sit with me and ill take the lead” Thank God. I know what I’m doing, but initiating with someone new was a scary concept. I obey her command. She puts a hand on my leg, near my crotch, and my dick immediately starts to grow. Its been far too long since I’ve felt someone else’s hand there. She leans in for a kiss, and I follow, meeting lips in the middle. We start with a few pecks, then lock in a passionate makeout session. Shes a great kisser. At least I think she is. She doesn’t seem to have any complaints either, letting out soft moans between her breaths. She takes one of my hands and places it on her chest. I take the hint and grab a handful of her D cup breast. “Under my shirt” she whispers, pulling away from my lips for a moment. Again, I obey, reaching under her shirt and feeling her soft breasts and now very erect nipples. I give one a light pinch, and she moans into my mouth. Im already in heaven by this point, when she grabs my now rock hard cock thru my pants and strokes the length. She pulls away from my lips again. “Fuck. I wanna see that”. I nod, and she pushes me back onto the bed and undoes my pants, pulling me put of my boxers. “Wow…bigger than I expected, can I suck it?” “Of course!” She smiles and leans down, firmly grasping the lower half of my shaft. Her small hands make my cock look great. She starts licking around the tip before suddenly swallowing me whole. She’s quite a bit more experienced than me.

After a short but amazing blow job, I ask to see her pussy, and she lays on her back, beckoning me to undress her. I pull her shorts off to reveal her beautiful hips and plump, wet pussy. I spread her legs, and she bites a finger looking at me seductively. Im excited. This is what I excell at. My thoughts of making my ex cum 4-5 times from oral alone flood my mind, and motivate me to do the same with Sierra. I kiss down her thigh till I’m right next to her slit, and ever so gently give it a lick from bottom to top. She gasps. I kiss her cleanly shaven pubic area and look her in the eyes. “Please eat me out, I want it so bad”. Say no more. I plunge my face into her pussy and start going to town. She tastes incredible and is soaking wet. In less than a minute she’s cumming in my mouth and my face is covered in her juices. She pulls me up for a kiss, looks in my eyes, and says “Please fuck me.”

I pull the condom out that ive been keeping in my wallet for quite some time now and slide it on as I resume my position over her, holding myself up with one hand, and guiding my cock to her pussy with the other. As I make entrance, I feel her tight, wet lips constrict around me. I usually hate condoms, but it was the only barrier between me lasting or blasting. “You’re so fucking tight.” I say to her as I slide my entire length in. She lets out a deep moan of pure pleasure as I completely engulf myself in her warmth. I remain buried in her for a moment, before beginning to thrust. I start out gentle, and she whimpers lightly every time I reseat myself at full depth. “Harder baby, fuck this pussy good” she demands. I obey.

I manage to make her cum twice during the first round, switching thru three or four different positions, starting with missionary, some doggy style in the middle, with her beautiful ass in my face, to on her back, legs open, while I kneel below her and pound away. “Oh my god, I’m cumming, where do you want it?” In between gasps, she manages to reply “Paint my pussy baby!” I pull out, and rip the condom just before blasting a massive white load all over her pussy and lower stomach. “Oh my god, there’s so much! It HAS been a while for you” she giggles, still panting. She swipes a finger thru the mess and sticks it in her mouth. “Mmm…. you taste good” and swipes again. Im over the moon. Confidence and heart rate thru the roof, I collapse next to her.

“That was incredible… now what? Do you want me to leave?” I inquire. She rolls to her side to look at me. “Are you kidding? No!” She laughs. Her laugh is intoxicating. “Stay the night with me!” I don’t have to check out of my hotel till 11am. I can stay. “Plus, you gotta fuck me in the morning. Its my favorite way to wake up.” This is new for me. “How?” I ask, intrigued. “If you wake up before me, just put it in. I give you my consent. If I’m awake first, can I play with you?” “Of course, thatd be amazing!” I reply. “Great!” She says with an excited smile.

We clean eachother up, get back in bed, and she falls asleep with her head on my chest. Before I doze off myself, I think to myself if I’d ever wanna try dating again after this. At the moment, I couldn’t think of a reason to do so.

If you read this far, thanks so much, and I hope you enjoyed! I can continue this story, and I can tell others! My DMs are also open to messaging about anything!

Source: reddit.com/r/gonewildstories/comments/upqp81/my_first_hookup