First Handjob with my High School Sweetheart

Posted by: Age: 16 then Posted on: 1 comments
1 likes 5881 views Category: Male-Female Tags: handjob, aroused, clit, panties, wet, Mutual Masturbation, Orgasm

I'm grateful to my high school sweetheart for unlocking my inner sexual animal.

 

My next big masturbatory adventure happened when I was 16. I mentioned I was a Catholic school student in my previous story and at this time I was still a serious believer - no tomfoolery with girls until marriage. I had been dating my high school sweetheart for probably four months when this happened.

She came from a large family in a small house and I had an average-sized family (a mom, a dad, a brother, and a dog) in a medium-sized house. So when we just wanted to hang out and watch TV we would by default opt to hang out in my basement. My parents always let us be and even gave us the courtesy of letting us know when they were coming downstairs - gave us lots of time to reposition on the couch! (In hindsight, I don't think I appreciated that courtesy until writing this story.) We'd kiss and cuddle with a little light fondling, but that was it. I'd dare never attempt anything further.

I didn't think there was anything special about this night. We were sitting in the basement, watching TV, and per usual decided it was time to get her home and we could both go to bed. The usual goodbye ritual involved a long hug and steamy french kiss. (She was a great, soft, passionate kisser.) Tonight was no exception.

Except, out of nowhere, she thrusts her right hand onto my dick and squeezes.

I stopped kissing - definitely didn't move her hand! - but she'd have none of that. She drew me back in with her other hand as she started stroking me through my pants and underwear. It took maybe all of 10 seconds for me to surrender to her. I was at her disposal. She pushed me back onto the couch and straddled me, going straight for my belt and pants. She freed my now 6" cock from my shorts and pulled on me like a seasoned veteran. (For the detail minded, I'm circumcised with enough skin left to slide up and down over my entire length.) She bounced up and down with every stroke while stifling my moans with her tongue. Her quickening urgency consumed me, and I warned her I would be cumming. She aimed away from face and I unloaded over her hand and onto my lifted shirt and my (then-hairless) chest.

I'm left panting with a spinning head with an aroused 17-year-old on my lap. Having done no prior research on girl parts or girl fun (I was an awkward kid, so I never really had friends to gossip with; my Catholic sensitivities sure didn't help), I was at an utter loss what to do next. Surely I had to return the heavy petting favor, right?

I was given some advice about confidence growing up: fake it until you make it.

I unbuttoned her jeans (first time into a girl's pants!) and slipped them down low enough (first time seeing a girl's underwear in place!) to give me access to her mound. With her still on my lap, I twisted my right hand around and slid it into her panties. First bush, first folds, first wetness, first clit. Basically, I frantically (but with focus) moved my hand back and forth over the bony and bumpy parts of her wetness. She wriggled and breathed more heavily. When my hand got tired, I changed directions. She'd wriggle more and bite her lip. I'd quicken to match her pace, and up and up and up we went. After what felt like an eternity, she fell forward onto me, bracing against my shoulder for support. She spasmed three times, little whimpers and oomphs in between each.

And there I was, a 16-year-old boy wrist deep into the hot, wet, heaving folds of my high school sweetheart with my own cum running back down to my crotch.

After a come-down cuddle, I grabbed a towel and washed up. She gathered herself, we both re-dressed, and quickly left my house in order for me to drive her home. I thanked her profusely like any geeky boy would. We never discussed why she did it or how we both wanted it. I savored her scent on my fingers for days (although I probably just imagined it for the days after). But it began a wonderful two years of Friday night handys, exploring and experimenting with each others bodies and teaching each other about how we worked. (But that's the end of that fantasy. We never "did it" but eventually did move to penetration, toplessness, and nipple play, and I gave her oral only once after much convincing and promising I didn't need reciprocation. That's it.)

It was a great foundation for the years ahead. It remains a great memory I replay in my mind. And I still love a woman who makes the first move.

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