*For more than a year, ominous rumors have been privately circulating among high level* gossipers at my high school. Everyone mentioned below is 18 or has recently turned 19 years old. Except Sylvia’s mom who is in her late 40s. [Part 1](https://www.reddit.com/r/gonewildstories/comments/l4ekgz/dr_sylvia_or_how_i_learned_to_stop_worrying_and/) is about the very first time Sylvia and I hooked up. [Part 2](https://www.reddit.com/r/gonewildstories/comments/l4wnxx/dr_sylvia_or_how_i_learned_to_stop_worrying_and/) details our second encounter.
Things have been friendly but only platonic between Sylvia and myself since that April evening in her den. She isn’t dating someone who’s not me, so that’s good. But I’ve been wanting more benefits to go with our friendship for almost 2 months now. And I’ll find out she feels the same way when my parents leave town during June of our senior year. It’s finally my turn to host some debauchery. I gather together 2 flats of tallboys, 2 packs of Camel wides, a half ounce of weed, and a handle of vodka… *shoot, a fella could have a pretty good weekend in Vegas with all that stuff*. Between the twenty-odd people I invited on this Saturday afternoon, these basic supplies last less than 8 hours.
Thankfully things stay under control. My small event dwindles down as the supply of *foreign substance to introduce to our precious bodily fluids* diminishes, and before 11pm I find myself sitting alone on the couch next to Sylvia as the last of my other guests are leaving. “Weren’t you going to get a ride with Alice?” I ask with a yawn as I tilt my stoned head lazily to the right to make eye contact with her.
“You want me to leave?” Sylvia responds with disgust in her voice and a deadpan look on her face. Despite her best efforts, she’s not able to hold the serious expression for long, her face changes to match mine as I pick up on her factitiousness and soon we are both grinning ear-to-ear. We embrace and finally make out for the first time. I lead her to my room and we shed most of our clothes on the way. *For reasons which at this moment must be all too obvious.* (That’s the last Dr. Strangelove quote, I promise.)
She lays back on my bed, her legs dangling off the edge, and I kneel down to get to work with my mouth. Her juices are already heavily flowing so I don’t linger long before standing up and sheathing myself with a condom. I study her body from above as I place my hands to her sides and my tip enters her in missionary while I am still standing at the edge of the bed. She let’s out a loud grunt, and leans forward to grab my back with both hands, pulling me closer. Then she snarls her lip at me, and holds my eye contact as I finish sliding all the way into her wetness before rolling back her eyes with a loud “Ohh.”
I delight in her reactions, how today it seems she is not holding anything back. I immediately want to bust. I manage to hold my form for a minute or two of fast deep strokes. We switch to doggy and 5 claps in she’s started really throwing herself back into me. I press my palms into her voluptuous cheeks with all my bodyweight. My breathing gets louder and labored when I finally give up and let my nut go. She’s giving me affirmations as my ejaculate is expelled deep inside of her, inflating the reservoir tip of my condom.
“Yes baby! You are filling me up so good!”
Later she would tell me she really liked the way the kegels I was doing during missionary, to hold my orgasm back, felt inside of her. We would have some great pillow talk this night as we lay together in my bed and the chat continued as I gave her a ride home. The following day would be a completely new chapter in my life as I finally learn to stop worrying about my size. She thought I was the girthiest partner she’s ever had and that only 2 of the other 10 were longer than me. It was mind blowing to learn that not only did I have a nice/beautiful cock, with it’s clean circumcision and slight up-curve shape, but that she thought I also had a big one.
She explained her preference for girth, how she liked being filled that way but too long of a dick could hurt. And she also went further into the finer points of grower vs shower. Grower was a term I had never heard before she called me one in April. Really all of this stuff was completely new territory for my young self, and it was fascinating.
We would go on to have more than one tryst a week for the rest of the summer. Things would start winding down mid-August, as we approached the inevitability of us each honoring our commitments to separate universities located on opposites sides of the continent. Some of our hookups were of course more memorable than others. Like the time I came by with a six pack of canned Corona, a handful of joints, a pack of cigs, and then we had sex for hours in the middle of the night, out in the open, on a blanket, in a park.
But the most memorable session takes place near the very end, back in the den at her parent’s house, the place where she first gave me head.
This den is hallowed ground to me. It’s one of the most sacred spots in my sexual history. Sylvia referred to it once as her “command center” within her parent’s place. They owned a beautiful old house that was filled with squeaky doors and creaky floorboards. The den was on the ground level, everyone’s bedrooms were up above, with her parent’s one facing the rear yard. The den faced the front of the house and from within you could hear the front yard’s gate opening whenever someone was coming home. Regardless if she had snuck me in while her parents slept, or if we were home alone, we always hooked up in the den. From the den’s strategic position the noisy house could provide us with ample warning, no matter where someone might have been approaching from.
It’s 2am and still miserably hot outside. I park at the intersection where she always goes to smoke. Sylvia greets me with a kiss and we’re ass-grabbing each other as we make our way up the block to her front gate. In the moonlight, I see her raise her index finger and touch it to her lips when I exhale just a little too loudly while she’s maneuvering the gate’s rusty lever. She uses an even lighter touch when we get to her front door knob and we finish this practiced routine by tip-toeing across the foyer in total silence until we get inside the den with the door closed behind us and the TV turned on. A paused episode of South Park pops up, she presses play on the DVD remote, and cranks the volume.
Then, in no time flat, she has tossed the remote, her shorts, and her t-shirt to the floor, revealing only a black thong underneath. I drop my pants and am standing across the small room as she climbs onto the familiar futon. When I look up again after having shed my shirt, I am treated to the sight of her naked legs pointed straight up in the air, her feet high above her head and her upper back pressed against the rear of the futon. Her huge teenage tits are supporting themselves and only their round sides and center cleavage is visible as the rear of her knees blocks her nipples from my view. She’s holding both her lower thighs in her hands and she slides her butt closer towards to me as she grabs the rear waistband of her thong. After shimmying the thong halfway up her legs, her fingers head back down to fully spread open her vulva. She stares into my eyes as I feast on the sight of her now totally bare and gaped pussy.
“I got a little carried away with my razor today. You like it?”
I’d never seen her before without at least a fully grown landing strip. She would shave the rest of her hairs around that large patch occasionally. But tonight everything is gone. She then takes her finger from her mouth and touches herself with it, I can see wet grool already emanating from within her inner lips and onto her fingertip. I finally stammer out something like yes, it looks so smooth. To which she says-
“Come taste it.”
I kneel in front of the futon, grab her hips, and work my mouth slowly down her soft, freshly-shaven mound until I’m covering her clit. She has told me what she likes best down here by now. I purse my lips around her clit to create really strong suction that I hold while moving my tongue. My tongue is slow and gentle at first, then I increase the pace as her moaning gets more intense. She told me that when I had stopped my clitoral assault right at the start of her orgasm the very first time I went down on her, that I had almost ruined it. Her preference was for really strong motion across her clit the entire time she was climaxing and I knew this about her well by now. I also knew exactly how to edge her which I did tonight for at least 5 minutes.
Neither of us are paying any attention as the South Park end credits theme starts blaring through the TV. I have my left hand spreading her vulva and just as she thinks I’m continuing with my edging of her and am about to let up again, I decide to go for broke with my tongue pace while simultaneously entering her with 2 curled fingers from my right hand. She starts shuddering and I increase my tempo to the max. I’m now racing my tongue across her clit as fast as I can and am poking hard at her g spot with my fingers using the same feverish pace. She would tell me later this was the best orgasm of her life. It lasts for over a minute. She’s convulsing and letting out loads of loud ohs and moans the whole time.
The South Park end credits theme stopped right in the middle of her pleasure cries. All of the sudden it’s nearly silent in the room as I have finally stopped my two pronged attack and her loud breathing has begun relaxing. Then I hear the creaking of floorboards.
“Fuck- you need to hide in the bathroom.” She whispers with terror in her eyes. I stand up and start walking towards my pants when she says with even more concern in her voice “No, go!”
I can now hear the movement she’s hearing right on the other side of the wall and I propel myself with a quick jump-step through the open doorway, narrowly missing the sink. I don’t have time to close the powder room door behind me as I hear someone turning the knob to open the door to the den.
“What are you doing down here?” It’s Sylvia’s mom’s voice, she sounds startled to be seeing her daughter.
“Watching TV.” I can hear Sylvia reply sheepishly but I can’t see her. The door to the powder room is open at a 90 degree angle. I’m cowering fully naked behind it, truly in fear now, with two hands covering my erection. I take a look at myself in the mirror above the toilet, the soft glow from the silent TV screen is the only light in the room but I can still see Sylvia’s wetness glistening all over my face. I try to wipe a bit off. When I look the other direction, through the small crack between the edge of the door and the wall. I am able to make out the South Park DVD menu displayed on the TV. I can also see the remote on the floor, it’s all the way across the room from the futon where Sylvia is laying.
There’s a moment of lingering silence. I imagine that Sylvia’s mom is noticing the status of the TV and the remote and is realizing that her daughter is full of shit. “In the dark? Are you naked?” Her mom asks each question somewhat incredulously, pausing only briefly between them.
“It’s hot.” Sylvia replies, not untruthfully. I hear the floorboards creak again as her mom steps further into the room. “Mom!” Sylvia protests her mother’s advances loudly. “Leave me alone!”
“I don’t know what you are doing down here. I thought I heard a scream.” She continues advancing across the room, I can see her mom’s short frame silhouetted as it passes by my view of the TV through the door crack. She is skinny with short black hair and is wearing a bathrobe and slippers. If she had turned to look through the crack, she would have seen me staring at her. Instead, she takes a step into the doorway of the powder room. I press myself against the wall as flat as I can. I see the door opening wider, she must be pushing it. The door gets open to about a 150 degree angle before stopping as it presses up against my erection.
“MOM! PLEASE!” Sylvia yells in a panic. I’m pretty sure I hear her get up off the futon. I continue to hold my breath. Her mom just stands there and continues to press the door into my hard cock for another 3 seconds. Then finally the pressure on my tip eases up a bit.
“Go to bed.” I hear her mom say simply. Relief floods over me when I see her silhouette again through the crack as she’s walking back across the room and exiting the den. Sylvia walks to where her mom had just been standing, we’re still being totally quiet listening to her mom make her way through the house and back upstairs. Sylvia presses the door back into me, the same way her mom just had.
“Ow.” I whisper. She opens it back to 90 degrees, then peers her head around it to look at me. She gasps, drops her jaw, and covers her mouth with her hand when she sees me and realizes that my hard cock has been what the door was pressing against this whole time.
I still have my back against the wall and she watches as I start to stroke myself gently with my left hand. With just a moderate pace and 8 seconds time, I make myself spurt all over the floor. Sylvia’s head is still leering around the corner at me watching as I pleasure myself while we are less than a minute removed from the peak fear of this terrifying ordeal.
“Oh my god.” She says somewhat disgustedly when she realizes I’m climaxing. She turns away and leaves the powder room immediately after seeing the first couple shots of my cum flying out, leaving me to finish sputtering alone. I wipe up my mess as best I can in the dark then get dressed while she starts the routine of silently opening her front door to sneak me back out. We then silently mouth goodnight.
It’s still a mystery to me today as to whether or not Sylvia’s mom knew I was there, standing right behind the door she was pressing. Sylvia has never summoned up the courage to ask her, as far as I know. Sylvia and I did get together for a few more nights of hot times after this, but things were never quite the same. And ever since that night, I’ve fetishized the idea of being caught.
Source: reddit.com/r/gonewildstories/comments/l5njlp/dr_sylvia_or_how_i_learned_to_stop_worrying_and
Wow, one heck of a night.