The spring of 1995 was a great time. I had just turned 18 at the end of my senior year and was legal to buy porn, which I did in copious amounts. After baseball practice I would bring home Playboy’s Book of Lingerie or Cheri or Club or Swank, and in the hour of free time I had before my parents returned from work I would have 60 minutes of bliss perusing the gorgeous, painted glamour models on their glossy pages, big hair, big tits, trimmed pussies, sensuous eyes with way too much makeup, and provocative lingerie. I would strip naked, lower my pelvis to my cheap mattress with the foam egg-crate cover and rub myself along its softness, fantasizing about Kelly, Janelle, Colleen, Danielle or Miss Chaplin, the college teacher visiting for that semester. The porn was just a trigger, what really got me off were my wild fantasies of the impossibly hot girls on the cheerleading or softball teams who loved making saucy comments to rile up us boys. I cut a hole in my fitted sheet and plunged my cock down into the soft foam, trying to imagine what Jenny’s, what Robyn’s, what Kathy’s or Kimberly’s pussies looked like as they rubbed themselves off at night. My room stunk of jock sweat and male pheromones, day and night. A football program stashed under the mattress had long since fused together on the cheerleading team’s group picture and bio page. My mother discreetly avoided mentioning the source of the funky aroma, but flatly refused to enter my room.
In the spring my father had done very well at his work and he and Mom were rewarded with a two-week, all-inclusive trip to San Juan. For short vacations, they were comfortable leaving me in charge while my brother was away at college. But for something this long, they felt safer with an adult minder, especially if something went wrong like a fire or a bad accident and someone needed to be in charge. Enter Erin. She was a sex therapist (really!) who lived in the neighborhood, was in her early 40s and had just gone through a divorce. Erin was confident, brassy, and very forward. She got a kick out of playing I-know-what-you-boys-are-up-to. I was a dirty, coarse kid but I had a horniness that obviously shone through.
Because of her work, Erin talked openly and provocatively about sex and her sex life, especially how hard it was on the dating scene and how forlorn she was for attention in the aftermath of the divorce. It was sophisticated and hot, like the dialogue from a mature TV show or movie. One night she asked me if I had a girlfriend and I said no, not yet, girls were too much work and I was trying to get into college. “Oh, honey,” she said, swatting me playfully on the shoulder, “you’re going to ask one of the Rams’ cheerleaders to homecoming and you’ll be spending all of your time in the shower getting nice and clean and smelling good for your girl.” The way she said it, the look in her eye, I could tell Erin was thinking about me.
She was crying out for sexual attention. I overheard her in the back yard talking to my Mom. “Christ, I need to get laid,” she said one night. "I'd fuck my sister-in-law. We're still on good terms."
“Erin!” my Mom shot back. Her husband was an awful man and treated her very badly. But Erin replied something cynical and dismissive, noting that she had needs, too and would be happy to use other people for a change. I went to my room that night and nearly pulled my dick out by its roots, looking at Erin’s bedroom window from mine and wondering what she was doing to herself in there, trying to imagine who she was fantasizing about. The thought of her cavorting on her bed with another woman was intoxicating; I'd only understood such things on the glossy pages of a porn magazine, totally made-up, posed-out, high-fashion lipstick lesbian sex presented for the pleasure of the male gaze, not for women.
So when Mom said Erin would be minding the house while they were gone, I put up no fight. It didn’t really matter, I had my own car, I was 18, and responsible for myself. Erin would just be coming over to help, basically. I was still going to cook my own food and get myself to school. In fact, I didn’t really know what Erin’s schedule was. She was unemployed, living off the divorce settlement, and filled her time cleaning the home, watching our premium cable TV and taking care of our many small pets.
One day I came home, my metal baseball spikes clacking on the brick walk through the back yard, and saw her reading a Cosmopolitan with BIG SEX NEWS blaring from the cover, sipping what appeared to be a vodka-and-tonic. She was relaxing on a chaise longue, wearing a modest swimsuit — bandeau top with a sensibly-cut panty, red with white polka dots. Erin was wearing smoky stunner sunglasses under her jet black pageboy haircut. I remember watching her lift the frosted highball glass to her lips to take a long sip of booze.
“Hi,” I said, not really knowing how else to break the ice.
“Your bedroom smells like cum,” Erin said without looking up, absolutely stunning me.
I gulped for a reply like a goldfish that had fallen on the floor.
“What are you doing in there?” Erin said, turning a page sharply. “Is that all you boys do all day?”
I know I turned bright red. My face was hot to the touch. Still I had no reply.
“Don’t you ever do homework or study or anything like that?” Erin teased. “Is it just nonstop for you?”
My heart was pounding. It was one thing to be accused of beating off by a male friend on the baseball team; that was something to conceal or to deny. But a woman, especially an older woman, not related to me, it’s very hard to describe how arousing this was. I stood there, blinking.
“Honey, it’s natural,” Erin said, taking off your sunglasses, “but think of your poor mother and anyone else who lives in the house. Maybe go outside or in the garage once in a while.”
“OK,” I croaked weakly. “I’m sorry.”
“Don’t be sorry,” Erin said, “it’s your body, but try to have some consideration for others.”
I practically floated an inch off the floor as I walked back to my room, light-headed. Erin was coming on to me for sure. When I got to my bedroom I stripped out of my practice sweats and stood there, tangy and salty with sweat and musk. If Erin wasn’t there I’d be fucking my hand. But if Erin already knew how much I was beating off — and seemed to like it — why not?
I was humping the mattress and gazing upon a bevy of Playboy Playmates, grunting with passion and barely concealing my activity when there came a soft knock on my bedroom door. “I put some clean towels in the bathroom for you,” Erin said matter-of-factly. Oh, that did it. That sent me over the edge.
“Thank you,” I groaned before burying my face in my pillow and emptying my teenage balls into the mattress, panting and heaving with lust. The small of my back and nape of my neck glistened with sweat. I lay there for a long moment, feeling the burn in my thighs and ass cheeks, as I finished my orgasm.
“You’re welcome,” Erin said finally. She was obviously standing by the door to listen to me get off. It was Tuesday. I had 10 more days with this woman.
You must be logged in to post wall comments or like a story. Please login or signup (free).