Fucking a school teacher silly while her best friend watched. Or: mountain vacation sex [MF] [F] | 2016

This was years ago, but always fresh in my mind. Shelly (32) was a middle school English teacher. Shoulder-length, straight, chestnut brown hair, rich brown eyes, olive skin with a tan, 5’5” and a set of DD’s that we’re her favorite feature (they were spectacular). Shelly and I (23 at the time) for about 4 months has one of those hit, passionate, raw relationships that they write about in coming of age novels. I, feeling like a king for being the young guy who landed the smokin’ hot older girl, her with a confidence boost for landing the younger guy, turned that summer upside down.

Shelly was living in Florida with a long-time boyfriend. After breaking up, she moved up to the coastal town I lived in to stay with her friend, who happened to be my best friend. We met casually at a bar one night when my band was playing; I thought she was gorgeous and loved her body, we chatted for a bit but that was that. I never really thought anything else about it until I saw her again at a 4th of July party. My friends and I went down to a party on the harbor and she met up with my best friend and joined us. We said hello but never really separated again for the rest of the night. Conversation was natural and fun, we set a date for later in the week.

Friday came around, we had dinner and drinks, grabbed a 6 pack from the gas station and walked back down to the harbor and camped out on a bench facing the water for the next 3 hours. It got dark and she turns to me mid conversation and asks, are you going to kiss me? Fuck yes. This girl I’d take charge and I dig that. We make out for half an hour when I feel her hand move to my lap. She starts rubbing my dick through my jeans until it was rock hard. She looks around and next thing I know she’s got my dick out and I’m getting a public hand job. I’m very in to exhibitionism so I knew this was going to be fun.

Fast forward a few months and we’re dating exclusively, meeting each other’s friends, using titles etc. Her best friend (cute, girl next door vibe) is married to a very wealthy, prominent man in town. They invite us up to their mountain house for a weekend if drinking, cooking, and relaxing.

Shelly and I leave work early on Friday and make the 3 hour drive up to the mountains. On the ride up she informs me that her best friend and her husband are swingers. Cue that record scratch movie moment where time freezes. She assured me there will be no swinging and that they know she’s not, nor would she ever be, a part of that world. But she tells me, I don’t want you to be alarmed if you see them walking around naked. Right. No problem, thanks for the heads up.

We get to the house and are greeted with drinks and invitations to the hot tub on the porch. Shelly and I settle in and make our way to the hot tub with a few more drinks in tow. Shelly had been teasing my cock the entire car ride up, so I’m in hair trigger mode as we sit down in to the water. She looks fucking amazing in her white two piece and my mind is running, I end up getting hard, the kind of hard that doesn’t go away. Shelly somehow brushes unintentionally against it and smiles. She tells me to stand up, pulls my shorts down and starts giving me one of the most erotic blow jobs I’ve ever experienced. Open air, tipsy, mountains, cool night air. We hear her friend inside so she pauses and tells me to sit, and takes my shorts all the way off but tells me not to get out of the hot tub. Her best friend Kelly (yes, I know, best friends Shelly and Kelly, but it’s true) comes out, topless, the first set of fake tits I’d seen to this point, followed by John, her very naked husband and his monster hog - which should have its own name, maybe even area code. I don’t know whether to stare at her tits or this porn cock flopping around. We are joined in the hot tub but Shelly never lets go of my Dick. Instead, she continues to give the most subtle, slow, handjob under the jets.

A few hours pass and we are all getting tired. Shelly has relinquished control of my shorts. Kelly escapes to their bedroom, Shelly goes downstairs to our bedroom and I go help a fully clothed John clean up our bottles. After some small talk and good nights I head downstairs to Shelly completely naked and asleep on top of our bed. I can’t go to sleep with this nuclear reserve of cum still in me so I kiss her and she wakes, wraps her arms around me and rabidly sticks her tongue in my mouth. I send my hand straight down to her pussy and start rubbing her clit. I’m wasting no more time, I’ve got to taste her. I climb in to and kiss my way down to lick one of the prettiest pussies I’d ever seen. Even after months of dating I was still in awe of it. I’m licking and tongue fucking her for awhile when I can sense she’s close, her breath is short, her moans are closer and louder when are Started to hear “shell...OH!” Kelly had come downstairs, in her bathrobe, to make sure we had everything we needed, and I had forgotten to close the door, which was right at the foot of the stairs and opened right to the perfectly framed view of the bed. Where we were naked, with her legs wrapped around my face.

Kelly apologizes and starts to turn to head back up the stairs when Shelly surprises me, maybe both of us, and says “it’s ok, you don’t have to go, but neither of you gets to touch” and pulls my hair guiding me up. My now painfully hard cock slides in to her as I see Kelly take a seat on the stairs.

I start pumping in deep and hard but at a normal pace. Shelly turns to her friend and says “tell him how you want him to fuck me” she smiles. “Ok. Fuck her from behind, but face me” we do just that. “Harder and faster” Kelly opens her robe exposing her naked, tight body, and starts rubbing her clit. “Watch her while you fuck me” Shelly instructs. My mind can’t make heads or tails of what is happening, but I’m in to it so I’m doing exactly as I’m told. “Harder and faster” Shelly buries her face in to the bed as my hips are pounding on her ass cheeks. “Harder, FASTER” Kelly is being authoritative but speaking in a hushed tone so as to not make this a party. She’s playing with her nipples too now as I’m pounding as hard and fast as my body can possibly move without my heart bursting. Shelly is griping the bed quilt and screaming in to a pillow when Kelly instructs “stop” I stop and think I may pass out from the rate of speed, Shelly collapses on to the bed and says she Came hard several minutes ago and that my balls slapping her clit so fast was amazing. “Turn her over” I turn her on her back and start fucking her with her legs wrapped around me. “I’m close, where should I cum?” “Cum on her tits” I jump up to my knees at her side and unleash a fire hose of cum on to her DD’s. Shelly says that she’s was about to cum again so I slid my hand Down and rubbed her clit. I knew she loved her nipples and clit played with together so I sucked her nipple in to my mouth, licking the cum off and almost instantaneously she came with a body shuddering orgasm. We both looked at Kelly who closed her robe, smiled, stood up and said “I’m gonna find John” and walked back up the stairs.

We fucked a lot that weekend but that was the most mind bending sex of my young life to that point. Shelly definitely was responsible for a few years of seeking out older women.