Wednesday was Jeremy’s usual day for playing D&D. Honestly I have no idea why he never invited me to those things. I’m really good at fantasizing, and I’m really good at roleplay. Seriously, we could probably have tons of fun together. Anyway, he was usually busy for the evening, and on top of that, he and the boys were supposed to be going to see some show together. Since he was definitely not going to be home for hours, I made plans of my own.
After school, I returned home to clean up a little and get changed. I wanted to wear something eye-catching, but not too obvious. I picked out a plain white dress with a scoop neck and short sleeves. The dress came almost down to my knees, and I pulled on a pair of sheer white stockings that came up to above the knee. I walked back and forth in front of the mirror. None of my bare thigh showed, but I was certain I could manage to reveal some skin if I wanted to. Underneath, I had a pair of plain white panties and a matching demi bra with lacy edges. Finally, a pair of three-inch heels with criss-cross ankle straps, and I was looking pretty good. To me, anyway. Then I headed out the door to Jeremy’s house.
Of course, he wasn’t home, I knew that. But I was hoping his dad Bill would be. I’d come by a few times and even had dinner with the family once, so I was starting to at least be a familiar face. It wouldn’t be too strange for me to pop in unannounced, or at least that was my wish. As I pulled around the corner of Jeremy’s street, I eased my little Mazda over to the side of the road. I parked along the sidewalk, a good five or six houses down from Jeremy’s. Damn. Bill’s car was in the driveway, but so was Diane’s. Jeremy’s mom was funny and actually pretty cool, but what I really wanted was some alone time with Bill.
I’d never really spent any time alone with him, but he was half the reason I was seeing Jeremy. Good-looking older men really turned me on, and Bill was hot. Not, like, movie star-hot, but just what I liked in a man. Tall, with a bit of a belly. He had glasses and hair that was probably thinner than when he was my age but hadn’t receded too far. He had just the right wrinkles around the eyes and mouth, just the right graying stubble on his cheeks, and hands that were cracked and lined with age. God, I was getting wet just thinking about it on the side of the road. Too bad his wife was home.
I wasn’t really expecting to get laid that night, but my mind started wandering, thinking about those beautiful hands running along my 18 year old body, and his wide, full lips kissing my puffy nipples. I put my hand between my legs and started rubbing myself. With my other hand, I touched my side, my belly, and moved up to squeeze and fondle my little A-cup breasts. I imagined it was Bill touching me. I rocked back and forth in my seat, hand pressed against my panties.
It was still daylight. Anyone in one of the nearby houses could probably see me clearly playing with myself, but I wasn’t really worried about that. I was just getting worked up. I looked over at the shift knob between the seats. It was an automatic transmission, and the shifter was firmly in the Park position. I climbed over to straddle it, one knee on each seat. I held up my dress and pressed my pussy against it without trying to remove my panties. “Oh,” I said, finding it vibrating ever so slightly with the car still running. “Mmmm.”
I allowed both of my hands to run up and down my body, playing with my tits through my clothes. I moved my hips back and forth, rubbing up and down against the shift knob. I started pressing harder and harder, feeling the hard knob press into my lips and vibrate against my clit when I held my body just so. I thought about trying to fit it inside me, but it was too big and it probably wouldn’t go. I settled for rubbing against it through my panties, faster now as I could feel my panties getting soaked. One hand kneading my boob, I stuck two fingers into my mouth and sucked on them, coating them in spit, dreaming of Bill’s cock.
I could feel the car rocking as my bucking became more violent, but I didn’t care at all. My orgasm started to well up inside me and I moaned out loud as it overwhelmed me. I thrust my pelvis against the shifter one last time and my knee slipped off the seat, almost tipping me over. I hunched over the knob as my orgasm pulsed through me, one leg out to the side to steady myself. Panting, at last, I slid over to the driver’s seat and slumped there. The shift knob gleamed with fluid that had soaked through my panties. Great, now I probably wouldn’t be able to drive anywhere ever again without thinking about it and probably getting turned on.
I slowly caught my breath and looked around me. Most of the shades were drawn in the windows nearby; I didn’t see anyone looking out that might have been watching me. It didn’t matter anyway. Up ahead, I could see that Bill and Diane’s cars were both still in their driveway. Oh well, I’d had my fun. I might as well just head on home.
I shifted into Drive and pulled back out onto the road. I absentmindedly licked my fingers that had touched the shifter. The taste of my own pussy juice was kind of sexy. As I drove past Jeremy’s house, I saw the door open and Diane walking outside. She was looking behind her, saying something to someone in the house. I looked straight ahead, pretending I didn’t see her and hoping she didn’t notice me. Glancing in the rear view, I saw her walking to her car in the driveway. She wasn’t looking down the street, so she probably didn’t see or recognize me.
I drove around the block and parked again, one street away. Was she leaving? I looked down at the shifter again. Maybe I could find some alone time with Bill anyway. I waited five minutes, talking myself out of touching myself again. Then I drove around the block once more. This time when I drove by her car was gone. I passed by their house and circled the block one last time. This time I pulled into the driveway. I trotted up the steps and took a deep breath before ringing the doorbell.
After a few seconds, the door opened and Bill stood there. “Hey, Penny,” he said. “Jeremy’s out today, I think he’s going to be home pretty late.”
“Oh, I know,” I said. “I’m just a bit lonely today. I was wondering if I could . . . you know, hang out with you for a little while?”
“Oh!” he said, surprised. It took him a moment to get his bearings, and then he said, “Of course! Come on in.”
I followed him into the kitchen, where he stood awkwardly for a moment and drummed his fingers on the countertop. He was wearing a t-shirt over a collared shirt, and beige slacks. I thought he looked just adorable. “Can I get you something to drink?” he asked.
He was getting a glass from the cupboard. “What are you having?” I asked him.
“Oh, I was just going to have a glass of whiskey,” he said. “Got the place to myself for a few hours.” I looked at him, and he met my gaze. “You’re too young for a whiskey, of course.”
“I have had whiskey before, you know,” I told him. “I have to drive home, though. Just a water will be nice.”
He poured me a tall glass of water, with ice, and put some ice in his glass. I followed him into his study, where he kept the few bottles of liquor they had on hand. His study was beautiful, with a matching leather chair and loveseat. The walls were darkly stained wood, and there were several shelves of books and knickknacks, with some interesting artwork on the walls. I looked around the room as he poured himself a tall glass of whiskey. “This is a nice room,” I said. “I haven’t seen it before.”
“Well, this is where I get my private time,” he answered. “Here, and my workshop.”
“Oh, yeah, didn’t you say you build models or something? That sounds amazing.”
“Yes,” he said. “I was actually just going to work on something tonight, since Diane’s out. She doesn’t like me to hide away in there all the time, you know.”
“Oh no, that’s terrible,” I said, really leaning into it. “I think it’s wonderful that you have such an interesting hobby. I love men that work with their hands. Maybe you can . . . show me what you’re working on?”
He took a sip of whiskey, paused, and said, “Sure, come on. You can see it. It’s not much.”
“I’m sure it’ll be fascinating,” I said, and followed him to his workshop, which was the garage.
Obviously it was something he worked hard on over the years. There were dozens of models around the garage. Hanging from the ceiling were some airplanes, and there were a few small buildings and other vehicles on the shelves. Most prominent though were a bunch of sailboats, complete with tiny ropes and fabric sails and stuff. A large boat was half-constructed on a little table in the middle of the room.
He walked me around and showed me a bunch of different things, and I ooh’ed and aah’ed and asked him questions. Some of it was really cool, and I giggled and put my hand on his arm when he demonstrated the tiny working anchor on one of the ships. He showed me the one he was in the middle of, and what it would look like when he was finished.
“Oh, and the little steering wheel turns and everything!” I said. “Oops, looks like your glass is empty.”
He looked at it as though he hadn’t been sipping on his whiskey the whole time we were in there. “So it is,” he said.
“I’ll get you another one!” I said cheerily, taking it from his hand and hurrying out.
He began to tell me that I didn’t have to, but instead he followed me back to the study. I was looking at the few bottles on the sideboard when he walked through the door. I was leaning forward much farther than I needed to in order to read the bottles, turned halfway away from him, and sticking my ass out as far as I could. Hopefully he could see the tops of my stockings below the hem of my dress. “It’s this one, isn’t it?” I asked, pointing to the bottle.
“Um, yes,” he said.
I poured a little into his glass, but not too much. “Should I get some more ice?”
He shook his head, still standing by the door. “No, it’s quite good without it,” he said.
“Here, let’s sit over here,” I said, crossing over to the loveseat. I set the glass down on the coffee table in front of me so he’d have to come over to me instead of sitting in the chair further away. I slipped off my shoes as quickly as I could and sat down, curling my legs up beneath me on the loveseat. I put my hand on my leg, subtly tucking my dress into my lap to lift the hem up over my knees, making sure I revealed bare skin on my thighs.
He walked toward me slowly, and I said, “Come on,” patting the other side of the loveseat.
He sat down in a very ‘dad’ way, plopping back into the seat and then rocking forward to put his hands on his knees. He was just about to lean forward to reach for his glass, and I snatched it up instead, holding up to my face. “Is this a pretty good whiskey? Maybe I should have just a little taste,” I said.
“Oh, I don’t think–” he began, but I put it to my lips before he could finish. I really only took a tiny taste, because I didn’t want to cough or sputter. I rolled it around my tongue and then swallowed it quickly, licking my lips afterward. I made sure to make eye contact as my tongue slid across my upper lip, and then back across the bottom one.
“Mmmm, that is pretty good,” I said, handing him the glass.
He took a much bigger sip, and set the glass on the coffee table in front of him. “I kind of like the taste of whiskey,” I said softly. “But I think it tastes better on the breath of a handsome man.”
He licked his lips. “Well, Penny, I don’t think that’s probably–”
I cut him off again as I shifted my position, tucking my legs to the other side of me and leaning toward him. “I don’t think you’d cheat on your wife,” I said. “But maybe you could just kiss me once?” I laid a hand on his chest, moving it ever so slightly up and down. “That wouldn’t be such a big problem, would it? I just want to know what it’s like to get kissed by a real man.”
As I said this, I moved my face closer to his until I could smell the whiskey on his breath. Before he could protest again, I brushed my lips across his, feeling the tingle of the slightest contact. At that point, I really couldn’t stop. I moved my head sideways, brushing my lips along his again, then leaned in just slightly and opened my mouth.
He groaned, a deep, sensual moan that set me on fire. As I began to kiss his lower lip, he finally started kissing me back. At first our mouths opened and closed on each other, and then I grew bold enough to slip my tongue in. He seemed hesitant at first, but his tongue began to join mine, and I leaned into it, mouth wide, tasting the bitter whiskey on his tongue.
I gasped and moaned aloud, relishing every delicious moment. My hand slipped down to his waist, and then moved across the front of his pants to feel his obvious boner. I moved my hand up and down its length a few times, and groaned into his mouth to imagine it inside me. Suddenly he grabbed my wrist and pulled my hand away from his lap. “Penny, don’t,” he said. “I can’t. I just can’t.”
“Ohhh,” I said, disappointed. I thought I sounded kind of whiny, and I regretted it. I quickly moved to kiss him on the cheek, and then on the earlobe, and the neck. I whispered, “But I want you so badly.”
He exhaled heavily, obviously conflicted. “No, I’m sorry, I can’t,” he said. “I can’t have sex with you.”
I pulled away from him slightly, so he wouldn’t feel the need to stand up to get away from me. “That’s okay,” I said, still sounding a little petulant. “I won’t tell anyone we kissed. I know how to keep a secret.”
I ran my finger up and down his arm, trying not to break contact entirely as I sat curled up next to him. “I understand you don’t want to sleep with anyone besides Diane. I’ll keep everything we did here a secret. I won’t tell anyone we kissed.” I moved my mouth closer to his ear, and as I did so, I moved my hand down to my crotch. Very softly, I whispered, “I won’t tell anyone else that I masturbated in my car thinking of you.”
I made it obvious that I was masturbating again. I rubbed myself through my panties and moaned softly in his ear. I moved so I was sitting on my knees on the loveseat, facing him. “See, I was touching myself just like this,” I said, then leaned away and straightened up a little so my tits were closer to his face. His breathing was ragged, and he moved his hand onto the side of my thigh.
I grabbed my tit with my free hand and started massaging it. “Fuck, I love it when you touch me,” I moaned, swinging my hips back and forth in front of him and rubbing up and down my pussy lips with my fingers. He held his hand on my thigh and squeezed gently, but he didn’t make a move to touch me otherwise. “You don’t have to do anything,” I breathed. “You don’t have to do anything, just sit right there.”
After a moment, I got to my feet, standing on the cushions of the loveseat. I moved to straddle him, putting one foot on the armrest beside him. My pussy was directly in front of his face, and now I held my dress up so he had a clear view of me rubbing myself. “See, you can just watch, okay?” I said, now so wet I could smell my pussy. I wanted him to smell it. I wanted him to want it. “You can just watch me play with myself if you want, Bill.”
I was so close to his face that I could feel his hot breath through the fabric of my panties. I pressed my fingers into them hard, so he might be able to see my pussy lips. My juices soaked through the fabric and made my fingers wet. I was breathing heavily now. “Do you like that, Bill? Do you like to watch me finger myself?”
He exhaled sharply but didn’t say anything. I took my first two fingers and stopped rubbing myself with them to press them against his lips. He opened his mouth and sucked on them, and groaned deeply. “You like that taste?” I said.
“Uh-huh,” he mumbled as he sucked on the ends of my fingers. I pulled them out of his mouth and he moved his head forward slightly to follow them. I pressed my pussy against his face and I could feel him open his mouth, breath hot and hard against my dripping panties. I moaned very loud this time. He worked his mouth, opening and closing it, massaging my pussy. I rocked back and forth, pressing his head into the back of the loveseat, saying, “Fuck, yes, Bill, that feels so good! That’s so good, just let me fuck your face, please. I need to. Please, yes!”
I was getting louder and louder, grinding against his face, rubbing my clit over his nose and circling my pussy all around his gaping mouth. My one leg was still up on the arm of the loveseat, knee bent. My stocking was slipping down below the knee and bunching up there. “Oh, fuck, Bill,” I said, and moved my leg long enough to slip my panties down. I got that leg free from them and put it back up on the arm of the loveseat, leaving my panties to hang around my other ankle. I stuffed my bare pussy in his face quickly, before I lost any momentum.
His tongue came out and went up and down the outside of my lips like a paintbrush. His light stubble was scratching against the inside of my thighs. “Oh, fuck, Bill,” was all I could manage to say. I had my hand on the back of his head, jamming it against my wetness, dress falling around his head as I fondled my tits again with my other hand. He began to slide his tongue into me, and then to caress the outer parts of my vagina, slipping across my clit, plunging back inside. His lips kept working, slurping up all my juices as they poured out of me and I continued to grind against his face.
I moved my hand from my tits to my ass. I reached underneath me from behind to coat my fingers in the fluids that were now running down both my legs. I pressed my middle finger against my asshole, and then I slipped it inside. I still had my hand on BIll’s head, shoving my pelvis against his hot mouth as hard as I could. I began to slide up and down, catching the tip of his nose at the top of every stroke, coating his face as he frantically tried to drink up everything flowing out of me. I moved my finger in my ass along with every stroke, moving faster and faster. “Oh, fuck, Bill, I’m going to come!” I shouted. “I’m going to come for you!”
My orgasm was already breaking over me as I finished my sentence. I shoved his head hard backward into the cushion of the loveseat. My legs were shaking furiously and I let my weight rest on his face so I didn’t collapse. I let out a scream that turned into a squeal, and my orgasm rolled over me in waves. I let out a high-pitched squeak with each one, and it seemed to last for ages. My face was hot and I couldn’t hear anything from the blood in my ears.
At last I started to regain my senses. Bill was not deterred by my violent assault on his face, and he continued to work his tongue, lapping up all my sticky mess. I stepped backward, down onto the floor, chest flushed and heaving with massive breaths. He, too, was breathing heavily, and no wonder–he’d hardly had any air for the last ten minutes. I looked down at the massive erection that pressed against the inside of his slacks.
“You want me to take care of that?” I asked. I knelt down slowly and placed my hand on his leg.
“Oh, fuck, Penny,” he said. I moved my hand up his thigh to where his cock strained against his pants. I scooted forward so I was between his knees. “No,” he said, before I got to undo his belt buckle. “No, I think we need to stop now.”
I looked up at him with my best puppy dog eyes. “If you really want to,” I said.
He looked at me for a few long seconds and I thought he would change his mind. “No,” he said at last, and stood up. “No, I can’t do this, I’m really really sorry. You’re so beautiful . . . I’m sorry.”
I stood up in front of him. Standing on tiptoe to reach his face, I kissed his mouth and then his cheeks and his stubbly chin, licking up some of the pussy juice that coated the entire bottom half of his face. “Okay, I understand,” I said. “But any time you want to, all you have to do is ask.”
He mumbled something, wiped at his face ineffectively with his hand, then reached for his drink. I said, “I guess I better go before Diane gets home.” I kicked my panties off where they still dangled around one ankle, and I bent over to slip my heels back on, making absolutely certain to display my whole naked ass to Bill as he stood there.
“Yes, you’d better go,” he said.
I turned to leave, panties in hand, and I stopped at the doorway and nodded at his stiff cock. “I hope you think about eating my pussy when you masturbate,” I said. “That’s what I’m going to be thinking about in bed tonight.”
Source: reddit.com/r/sexystories/comments/rtavvc/my_chance_at_last_mf_masturbation_oral