[MF] The First Time I(19) Ever Got Handsy With a Girlfriend(18)

Hello. Fan of the subreddit, enjoy all your fun stories. I’m not a very sexually experienced person, mostly because I’m not very outgoing with new people. I need to just say screw it and put myself out there more.

Little Bit of Backstory

Anyways, although this story isn’t the juiciest, it happened back when I was brand new to the dating game. I was 18 going on 19 then (21 now) and usually just focused on gaming and school. Girls were of no concern since I had no mojo. Out of respect I’ll just refer to her as Chloe. She was a friend of a friend and just turned 18 (grade below me) at the time. High School lunch was fun, our little group always had each other cracking up. We’d even play Mario kart on my friend’s Switch.

Over a couple months of knowing we went from friends to having crushes on one another. At 18 I was like 5’8’’, bright blonde hair, dark glasses, not thin but not husky, slight muscle definition as I do work out. Chloe was a little taller than me, dark eyes, brown hair, big smile, luscious lips, tan skin, average bust, cute little butt. She almost always dressed in graphic t-shirts and usually no makeup. But she made sure she looked good, never felt like “one of the guys”, and had a wonderful sense of humor.

Eventually we got to texting over the summer and told one another we liked each other and we wanted to hang out with each other without everyone else around. The dates were a little awkward but we felt that spark and kept seeing each other. Keep in mind we were each other’s first ever bf and gf. So it wasn’t until like our 5th time together I kissed her.

We progressed to some sloppy making out moments where I will admit there was a 5% chance of our teeth clicking together because we were so new at things. Each time I realized I wanted a little more and would caress her butt or rub the skin of her back. I’d always make sure she was okay with things and she kind of just let me do my thing. There was even one time I got a little excited and was able to place her hand on my clothed privates to which she rubbed a little.

The Actual Event If You Wanted to Skip to It

Even though we were still figuring things out I’m pretty sure we both had this sexual energy being built up over our dates spent together. One night after dinner together, before bringing me home, I had her pull over (we’d take turns driving each other) in the lot of an apartment complex in my neighborhood. It was summer time so it was warm out but cool in the evening so we could shut the car off. I remember I was wearing a soft plain red t-shirt and khaki shorts. She wore a grey t-shirt with a white lettering phrase on it and short jean shorts (which I loved on her). With the middle console in the way we actually slipped into the backseat and sat there staring at each other for a moment.

We were a little nervous but we wanted to have a little intimate time together since we were young and wanted to experience it, and both our homes had parental figures looming about. I cupped her cheek and she placed a hand around my shoulder and we went at it. It wasn’t the most romantic kissing but the passion was felt. The making out went on for quite some time, I thought that alone was a lot of fun. Just the thought of actually having someone to do that with could make me skip a breath.

Over time our lips pressed together tighter and the flesh kissing got wetter. Tongues would touch but Frenching never really worked with us. Once we got to the point where things felt warm and we were softly breathing into each other during the exchange I decided to see where I could lead things (I wasn’t looking to go all the way). I rubbed her lower back and soon slid my hand underneath the hem of her shirt and felt her smooth skin. I pulled her closer to me and felt the faintest laugh from her on my lips.

I was hard at this point and feeling a little confined. But that’s when her hand went to my crotch and started rubbing the area. Now comedically enough, I was hard to the point my member pushed into my short leg so she was rubbing basically nothing. I slowly grabbed her hand and moved it an inch over and she felt the hard mass in length realizing what had happened. Our kissing grew deeper as she rubbed me through my pants and I was lost in my mind as this was the first time she ever initiated something. She’d let me play around with her a bit but normally kind of just held onto me in turn. I was happily surprised to say the least.

Now although I appreciated her attempt to engage in more intense foreplay, my khakis rubbing against me kind of hurt. I pulled back from her and said “I love this, but you’re going to rub me raw. Is it okay, if I… pull it out?” (Heart is pounding as I do this) You know what Chloe said? “It’s okay, I want you too”. Simple and awkward but in the moment I smiled brightly. Thinking about hearing that for the first time still gives me chills. It just meant a lot knowing a girl I liked wanted to feel me and give me pleasure in that way.

I undid my belt and my shorts and pulled them down to my knees. My 6 inches were at full go, she grabbed onto it and as our lips reunited she started jerking me off. There was no rhythm at first, but the feeling itself of having someone else do it was amazing in itself. I told her she could grip it a little harder and that’s when she started getting creative. She’d go back and forth from continuous short and fast strokes to slowing things down for longer more intense ones that often made my hips shift and got me to moan a little.

As I continued to have my horniness escalate, I pawed at her more. I fumbled with her shorts in hopes of returning the favor. Couldn’t get the damn button apart for the life of me. She was kind enough to laugh it off and undo her pants for me before going back to my cock. I slid my hand into her jeans and rubbed her through her underwear. Now I didn’t know about how to pleasure women then like I better understand now, so I kind of just rubbed in circles on the outside. She’d moan herself a little so I know I was doing some good. My brain had honestly flown South for the summer as the sensation of her playing with me was overwhelming for the first time.

She was leaning into me now, really getting into things. She really liked to kiss and I think she was honestly fine with me just doing that and was happy to do the stimulation for me. I wanted to give her some kind of extra attention so I pulled her shirt up to her neck and let it sit there. She didn’t stop me so I kept going. I messaged her bra a little before pulling that up too (I would have loved to take it off but I didn’t want to kill the mood if I took too long. How do you get those off smoothly?).

I held her back with one hand as the other fondled her breasts. I’d use my thumb to rub her nipples which I believe I got to stiffen. She continued with the occasional long and hard strokes on my dick which would cause me to lose my train of thought. Our necks were pushing our lips into one another as we kissed faster and faster. I could feel us losing time as she was on curfew so I pushed her onto her back on the seat and licked my way up her stomach and kissed her boobs. I then kissed her deeply as I jerked myself, feeling the urge build up as she held onto me, I eventually released onto a towel in her car (we weren’t thinking).

She kissed my cheek as I tried to calm my breathing. I would have wanted to get her off as well but she was needed home. She drove me to my house, told me she had a lot of fun, kissed me goodnight and I watched her drive off.

So that was my first ever sexual experience back when I had absolutely no clue what I was doing. But it is a memory I fondly look back on. However, we did eventually mutually break up a couple months later. It was a few things. It was hard for our schedules to work as I had a job and she had sports. I tended to always want to fool around which bugged her a bit and she acted really immature at times which bugged me. I hold nothing against her, glad it happened, wish her the best, she on the other hand thinks it’s too awkward to be around me anymore. I guess I ruined her for me lol.

I do have 1 more story about me and Chloe where we go even a little further. If you want to hear more just let me know. Thanks for reading.

Source: reddit.com/r/gonewildstories/comments/nuv7vx/mf_the_first_time_i19_ever_got_handsy_with_a