Finger Licking Good

In an effort to break away from the masturbation theme, I thought I’d move up to the next level this week and recall the first time someone else touched me “down there.”

The first time I got fingered was by my first “real” boyfriend in high school. I’d had a couple one-sided “boyfriends” (guys I liked, but who didn’t know it) and I went steady with a few others, but it was just kid stuff that lasted only a few days, or, at most, a week. Although my first kiss was with one of them, that’s as far as it went.

My first real boyfriend, Josh, started by touching my butt (over my jeans). I didn’t say he could do it, but, when he did, it was so exciting that I made only the mildest of protests. After that, whenever we would make out, his hands would be all over my ass, grabbing and groping. At the same time, he’d press his hard-on against me. This was beyond sexy to me back then – a real penis, right there, digging into my thigh, or tummy, or crotch. Much to my joy, he came in his pants a few times while we made out and dry humped. I felt like this was a huge accomplishment on my part, even though all I did was be there as something for him to rub against.

We would sneak out to the woods behind our school after classes (each telling our parents we were doing some kind of legit after-school club or sport). That’s where it was, as we were rolling around in the leaves, that Josh undid my button and unzipped my jeans. After that he groped my butt, rubbed his bulge against me, and tongue kissed me like crazy. Meanwhile, I was dying for more. I was unzipped! What next!? Maybe he was waiting for me to unzip him. I was clueless back then, but that would probably have been the right move.

Eventually his hand came back around to my front. A little titty action – under my shirt, over my bra. Then his hand moved down to my belly. I remember my clit literally throbbing – just like all those sappy romances said it would. His hand made it down to my panties. He ran his fingers over my underwear, driving me crazy. I don’t think he was consciously doing it as foreplay – he was going slow, feeling out if it was okay to touch me “there.” He took my silence as consent – I should have said something…”Finger blast me!”…but I was too embarrassed to admit how much I wanted him to touch my pussy.

It took a little time, but he began toying with the waistband of my panties. They were my white pair with little duckies on them. I couldn’t manage to speak, but I moaned to let him know I was liking where he was going. This apparently did the trick and his hand ventured down. He paused at my pubic hair, combing through it and sort of pinching my mound between his thumb and forefinger. It didn’t feel bad, but it also wasn’t what I was hoping for. I remember arching myself up in an effort to get him to go lower.

He soon got the hint, and just like that there were fingers moving toward my vagina – fingers that weren’t my own! He found my wetness with his middle finger and zeroed in on that spot. It was glorious. His finger circled my hole. I couldn’t tell if he was teasing me or if he was just trying to figure out where everything was. He wiggled the tip of his finger in.

Josh must have noticed a change in me…I think I may have stopped actively kissing him in anticipation of what was about to happen. He pulled away and looked down at me. His eyes were so big and beautiful. It was as if he was asking me if what he was doing was okay. I nodded yes to his silent question. We looked into each other’s eyes as he slowly pressed his finger deeper. Yes, I know it sounds a bit corny, but we were teenagers in love forever and ever!

I think I was saying “Yes…yes…yes…” as he digitally penetrated me. It was as far as I’d ever gone and it was a big deal to me. A boy literally had his finger in my pussy. I think I may have hyperventilated a little – either that or the dizziness was from pure horniness. He pulled back before going too far, swirled his finger around, and went back in nice and slow. It was wonderful. I was so fucking happy in that moment. I knew it wasn’t the same as losing my virginity, but for me it was about as close as you could get.

We resumed kissing as he continued to play with me. My clit was aching to be touched, but I don’t think he knew anything about the mysteries of the clitoris yet. I wanted to take his cock out of his pants and return the favor (just using my hand), but I was afraid that if his cock was naked, and my pussy was naked, that things would go too far. I wasn’t ready to go there. God, I was such a scaredy-cat! I grabbed and groped his hard-on through his pants hoping that would keep him happy.

I’m pretty sure this was one of the times he came in his pants, but I can’t say for sure. I just remember our frenzied make out session eventually calming down, his hand resting on my pussy, my hand gripping his bulge. Time was up and we had to hurry to get back in time for the late busses. He pulled his hand out, held it up, looked at his fingers, and sniffed them. I grabbed his hand and pulled it away, telling him that was disgusting. Sure, I did that myself after I’d played with my own pussy, but I was afraid my smell would be weird to him. We buttoned me up, and I pulled my shirt down into place. That’s when I caught him putting his fingers in his mouth. I fought to pull his hand away again, unwilling to admit I was turned on that he wanted to taste me like that.

It was the longest bus ride home that day. I was squirming in my seat the entire time. I was sure the other kids on the bus, at least the other girls, could tell how horny I was. I ran straight to my room, pulled my pants and panties down to my knees and attacked my pussy. I rubbed my clit like mad standing just inside my bedroom door. I came in a matter of seconds, dropping to my knees and rubbing for as long as I could stand it. After the tremors had passed, I got completely naked, lay on my bed, spread my legs wide and slowly began touching myself. I realized I hadn’t locked my door, but it felt too good to stop and get up.

I reimagined the whole make out session. The feeling when he pulled down my zipper. How his probing fingers moved over top of my panties. The exquisite sensation of his fingers toying with the waistband. The tickle across my pussy hair. Then his fingers on my cunt (Yes, I had already picked up that word from Dad’s porn stash). His fingertip, dry at first, then wet with my juices. Sliding, slippery, unsure where to go or what to do. Then rolling around my opening, searching, exploring, discovering. I tried to recreate the feeling with my own fingers, but it wasn’t the same…it was good, but not the same.

I finger fucked myself for a bit, then went back to my clit – the way I wished he had. I was bouncing up off my bed and doing everything I could not to scream out loud with happiness as I came. I lay there panting, naked, legs open, fingers caressing my virgin pussy…one step closer to becoming a woman…

Whew – okay, now I’m all worked up after that little trip down memory lane! You know what that means…

And, just so you all know, I did eventually give Josh some hand action and a few lame attempts at oral (made him come with my hand, but was unable to succeed with my mouth). We never really went further than getting naked together and fumbling around with each other’s junk. I shouldn’t admit this in our “me too” era, but I did, at times, wish he would “force” himself on me and just shove his cock in my pussy, but I was still afraid of “going all the way” for some stupid reason (I blame my mom). Sadly for me, he was too much of a gentleman to take me like that (or he was just as scared as I was).

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So, how was it for you? Do you remember the first time you fingered a girl (or were fingered)? The first time a girl touched your cock. The first time you touched a cock? Any regrets from back then?

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6 thoughts on “Finger Licking Good

  1. Rachel?

    Has anyone ever mentioned that you are SEXY AS HELL.???
    Your writing always, always, just turns me on and on and on!

    Thanks for this entry and for every single word you write and are willing to share.
    Fondly,

    Ironic990

  2. What a really good subject, thank you for sharing your first nubile experience.
    To answer your question, the first time I was sexual with a girlfriend was in mid High School. We had been dating for about a month when we took a day trip with her family, during which we had plenty of time to ourselves. Nothing happened during the day, beyond aggressive kissing and pressing ourselves against each other when out of sight, but it was still incredibly arousing for the both of us.

    That night on the way back we were in the back of the truck, under the cover of a blanket, when we both crept our hands towards each other crotches (both wearing jeans, that’s a regret). Neither of us orgasmed, but it was the most erotic thing I had ever done (it turns out the gf knew what she was doing) and I easily masturbated 5 times in as many hours after I got home. More happened later with her, but that’s a story for another time :)

  3. At 16 years old I was good friends with the school body president who had graduated a year prior. I moved away after my freshman year and was paying him a visit over summer break. On this day he had company- 2 gals about his age. He was trying to hook up with one of the girls and needed my help with keeping the friend entertained while he worked on his conquest.

    I was a 16 year old virgin with zero experience with the opposite sex. During the visit my buddy and one of the girls (the blonde) went to his apartment bedroom and had sex multiple times. The walls were paper thin and the closed door activities were easily heard.

    I stayed in the living room with the other girl, a brunette. The sex sounds were erotic and it made me feel very nervous. It did not take the brunette very long to figure me out. During our short time together we kissed like crazy, stripped to our underwear and she jacked me off while I kissed and sucked on her breasts. I was shy and fumbled through the entire experience but managed to have my most intense experience.

    I am still good friends with my buddy but never saw those girls again.

  4. I don’t think I’ve ever felt anything hotter than my girlfriend’s panties, covering her hot hairy pussy, after an hour of making out. And then, moving them to the side, and that pussy being so wet and open. Teasing the clit, teasing the lips, and then slowly sliding my finger into her. Sigh. To be a young stupid teenager again.

    Thanks so much, Rachel, for posting. I finally created an account to comment, but I check this site everyday flippin’ day. For years now. Years and years. I don’t think there’s anything hotter on the web than your website.

  5. The first pussy I fingered was Tonya’s, she was 14 years my senior. She was old enough to know what she wanted and bold enough to tell me. She directed me to a spot inside her pussy that if I rubbed while sucking on her clit, she would quickly cum all over my face.

    Andy

  6. Oh Rachael, you are an erotic delight, and it’s *always* a thrill to read your real life experiences… so envious of those lucky men who got to play with you!

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