I had been married to my new wife for 3 years when her son Mark started dating Tiffany. They were both 18, seniors in a catholic high school, promise rings and chastity pledges all around and heading to the same college upstate. Early on they had a lot of study dates, and this story begins on one of those. My wife was working late and the two were studying on the couch under a blanket while I watched TV, just a normal Thursday evening.
My stepson was average-looking, but Tiffany was nearly an archetypal male fantasy come to life. 5’6″ but usually stood 5’8″, couldn’t have been a pound over 110. Her bra tag says 34B but it looks a bit small on her. Cheerleader, of course, not the head cheerleader but definitely the most attractive. Better than A-student and they go to a tough school. I have no idea how Mark found such a beauty, but good for him!
About 8pm on this study date, the kids were giggling and laughing until Tiffany asked if I would go pickup a pizza she ordered. I was bored, so what the hell, and she popped up off the couch to grab her keys so I could take her car (mine was in the shop and my stepson was being a jerk). The cheerleading outfits were my favorite, and she did not disappoint tonight. Mostly red with blue stripe trim, skintight top and a skirt that stopped just short of proper. I grabbed the keys from her and headed out.
Before I left I had a smoke and then started towards the car. My stepson’s bedroom has these tall, narrow windows behind the bed visible from the side of the house, and a mirror on the wall in front of the bed, so when you walk past you can see the far wall and a slice of the bed in the reflection. The blinds are usually closed, but they were open, which I noticed because there was a teenage cheerleader standing at the foot of the bed in front of Mark pulling her hair back.
Her flat stomach was on full view with her arms up, and she gave a cute little head shake as if she was being playful with my stepson. I was behind them and to the left, so I could see her in full view and Mark from behind leaning back slightly on the bed. It was dark out and I was hidden, so I figured why not take a little look.
When she started to sway slightly, and ran a hand across her stomach and up to her breast, I settled in to watch. This was a show for his benefit, suggestive but demure, hands caressing, pushing, kneading. She reached out and tapped his nose playfully with her finger and then moved closer and dropped her hand to his lap. I couldn’t see it, but from the movement, he must have his cock out while she was stroking him.
Leaving him hanging (hah!), she peeled off her top to leave a frilly bra that looked, again, a bit too small to contain those breasts. Then she sunk to her knees, bent over, and I lost sight of her as her head dropped into his lap. Fortunately the mirror took over with a view from the back and her teen ass bent over in the skirt, the bobbing ponytail, and Mark’s closed eyes were clear indications of a blowjob in progress.
But my eyes were on the hem of the skirt pulled up over her ass. It was just high enough that I could see her completely shaved and tightly closed textbook-definition-of-simp/innie pussy from behind. I wondered if she lost her panties on the couch before I left (that giggling)… I licked my lips subconsciously.
Too quickly for me personally but probably plenty for him, she picked her head up and reached behind to undo her bra. I though I was prepared, but the sight of these 18-year old perfectly perky tits was breathtaking, like, I audibly gasped there alone in the dark. She pushed her breasts together and gave a little pout, impossibly cute, then a little mock tit-job and they were both laughing. She probably wasn’t quite large enough, but I chuckled with them.
As she stood up, the swaying and the hands started again, oh god, the swaying… He took the hint I think and was pushing his trousers down and off while she watched. For the first time I realized I had no idea how far they would take this, Mark and I didn’t talk about sex that much and with the promise rings? He kept going with his shirt, and she flashed up the hemline of her skirt playfully giving both of us a glimpse of that bare pussy before dropping the skirt to the floor. It seemed that chastity pledges weren’t going to stop them and virginity was long gone, so I unzipped and grabbed a hold of myself to enjoy it as well.
She turned around to face the mirror and stepped back towards him, her ass about even with his head, and leaned forward, giving his mouth access to the pussy I had gotten to see earlier. I couldn’t see anything from behind him again, but she was leaning forward so her tits hung down in the mirror very nicely. It was like an intermission.
Then she lowered her ass from his face into his hidden lap for Act 2 (but dammit, I’m not going to see anything!). I can see those tits in the mirror though, leaning forward and her head turned around, reaching behind her into his lap, obviously struggling to get the angle right. Teenagers… “Get the lube, Mark” I thought… and he heard me!
He laid back on the bed and reached into the nightstand, but my eyes never moved from her, because now I could see his lap and her amazing ass hovering over his cock was my entire world. I stared as he put some lube on the tip, leaned back again and she slowly, exquisitely, lowered herself onto his shaft. Her head was back, eyes closed, as she settled and took a deep breath. My stepson and I were equally hard in that moment even if I had to tend to myself.
She raised herself up just as slowly and arched her back, giving me a simultaneous front and back view of his dick pulling out of those lips, all the way to the tip. Then she dropped quickly, and I recognized instantly the movement that drove me nuts when my wife did it, slow withdrawl and a quick drop, the alternating of cool air and warm moistness… my hand was pumping furiously at this point. Did my wife somehow tell her about that? Did he?
I usually last about 5 minutes once that starts on me, but he lasted… about 5 strokes, pretty good for an 18 year old! Then in a flash she had her head in his lap, cock deep down her throat, as he was thrusting and obviously pumping in load after load. This time I got to savor all this without obstruction, my eyes flipping back and forth from the naked teen ass and now bright red dripping pussy bent over in the mirror, to the top of her head in his lap…
I must have cum harder than anything else in my life standing there in the dark. Instantly lightheaded, I closed my eyes and lost my legs in that moment, and fell to my knees as another blast of cum hit the bushes and splashed on the bricks.
By the time I regained my wits she was gone. He was limp, lying on his back, and I took off before they started to wonder about the pizza. Fortunately for everyone they went off to college shortly afterwards and then broke up. I never told him or anyone.
I think it was best that way, since my last memory of her in that final moment was better than any porn before or since. Those beautiful pussy lips in that mirror from behind had been a metaphor for her in my mind. First seen closed tightly as if bashful, clean and smooth, playfully hinting at her sexuality beneath a demure skirt. At the end swollen and pink with sex and lust, presented to me like a whore, creamy with arousal, gaping open as if seeking a cock to fill it. Burned into my skull is an understatement… more like augmented reality whenever I looked at her, and a constant companion behind my closed eyes for the rest of my days.
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First story in a while. Editors and feedback appreciated.
Inspired by a thread called Thankful for the View from gonewildstories that can’t be linked for some reason.
Source: reddit.com/r/sexystories/comments/7ixod9/my_trip_for_pizza_reveals_a_teens_secret_mmf_voy