Sessions with Doc Jenny: The College Girl and the High School Loser

October 4, 2014 (3 years ago)
Posted in Story: True Story, Taglish | Categories: Erotic Couplings, First Time | Tags: , ,

I was out with my family one summer during the early years of Punta Fuego when it was still really exclusive and was all the hype. I would normally sit by a tree and read or tan while my brothers and sister frolicked around in the sand or in the water.

So while I was sitting by the sea one morning, I noticed a bunch of high school boys that kept walking by me (or behind me). I felt like they were trying to get my attention as a bunch of them gathered somewhere else would get rowdier or louder as maybe one or two of them neared my location. I guess they thought it was "cool" if they sounded really loud as if they owned the place.

There were maybe seven of these boys and less than half of them (maybe three of them) had female companions and so the rest were by their lonesome.

So this went on and I kept seeing them around the place like at the jacuzzi's, bowling alley, billiards, restaurant. What struck me though was one particular boy. I noticed him because even though they're supposed to be friends (I mean why would they bring the other boy to Punta Fuego?), the other boys seemed to be bullying him around. This boy was your typical, off-the-shelf, couldn't-be-more stereotypical nerd: fat, pimples, messed up hair, thick glasses and this look as if he hadn't taken a bath for a week.

But I guess my heart went out for him because he kind-of resembled my baby brother who was also a little chubby kid (then).

One night as I was walking around alone, I saw them hanging out by the billiard tables again. Then I see this kid by himself in a corner just watching his "friends" play billiards as they showed how macho they were to the 3 girls they were with.

So I go there and ask him "may I sit with you?", as I beamed him a smile. The poor thing actually got shocked and was only able to stutter something which I got as a sort of "yes."

I chat him up and asked him what the heck was up with him and the boys and why he didn't join them. He told me he doesn't really know how to play billiards, or any sport for that matter and that he was keeping away because he's allergic to chalk (what the fall?!). That's when I also found out that his family were the members of Punta Fuego - needless to say that was probably the reason why these boys invited him.

I only noticed that we probably got the attention of the other guys because the rowdiness actually quieted down a bit and I could see the boys (and even the girls) staring at the two of us through my peripheral vision. Some of the boys were actually whispering to each other while staring at us while the girls would even point at the two of us and laugh.

As I mentioned, really reminded me of my little brother and the protective ate in me was really getting pissed-off at the attitude of his friends. So I got up and said in a loud enough voice: "Tara na. Show me your room." then grabbed his hand to go. The boy was still semi-shocked that I half-dragged him our of the billiards hall as his friends looked on in quiet disbelief.

We walk to their house which was not too far away and I ask him if he's ever been with any girl before after I've closed the door to his room.

He only shook his head as he was still staring at me in disbelief.

By the way, I was wearing spaghetti-strap tops and a sarong as a skirt with my two-piece bikini underneith.

I smile at him while I removed my top and my sarong to show him my white bikinis. He sat down on the bed and I sit down next to him and kiss him as I hold his leg and move my hand up his crotch.

His breathing got faster, almost hyperventilating, as my hand neared his dick and then he convulses as I touch his dick on top of his shorts. He actually came!!!

I break the kiss to confirm if he did cum and he only manages a sad-face while saying sorry. I laugh at him and tell him that it's okay and to go to the restroom and wash up.

I wasn't too worried. The boy was young and I knew for sure that he'd have liters of cum reserved and may be able to produce liters more at his current state of libido.

So I meet him at the doorway of the bathroom as he come out draped in a towel. I hug him and kiss him again. He hugs me back and tries desperately to kiss me but only ends up sucking my lips and wetting my mouth area with saliva. I ask him to remove my bra and he fumbles over the knots.

This time around, I guess because of sheer libido taking over, he pushes me back to the bed and lays me down. He starts sucking and licking my nipples and mashing my boobs and it actually felt very good, in a sloppy-wet kind of way.

I push his other hand down to my shaven pussy (gotta be well shaved if I were to look good in a bikini right?) and I let out a yelp in pain as he grabs my entire pussy.

I teach him to go slowly and which were the right places to touch. I remember being surprised that his hands were calloused and rough. It was his first time and he still hasn't gotten the rhythm right yet so I couldn't get to a high enough arousal to orgasm so I actually remove his hand at one point and just rubbed my clit myself and had him keep on sucking my boobs.

After I cum, it was my turn to push him down on the bed. I remove the towel covering his crotch and this maybe 4-inch dick shows up. It was very hard though and rearing to fight so I think, what the heck.

My plan was to suck his dick and then to straddle him cowgirl-style but as I hold on to his dick, believe it or not, this boy cums for the second time!

I was just too exhausted at that point so I just covered him up with his towel again and lay next to him. He tells me "sorry po ate" at some point. I just had to laugh mentally at that "ate" statement because there I was, laying naked beside a kid whom I just got to cum twice and he calls me ate.

I just smile and gave him a light peck on the cheek and told him I'll j... Read More

About the Author :

Joined: October 4, 2014 (3 years old)
Writings: 4

Send PM · Female · Offline

Hi There!

I'm a Psychologist by profession and I've joined another adult group as a way for me to destress from my sessions with my patients.

I've been sharing my stories in the said site, before another poster suggested that I might want to share my stories here as well.

So here I am!

My current hobby is discovering pick-up lines or opening lines used by guys in PM which would pique my interest enough for me to respond.
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