Alpha Male

How I slept with my girlfriend’s momIt was 2008. I was 19, dating this really cute scene girl, Kristen, who was a year younger than me. She was a tiny thing, skinny, and a bit of a myspace celebrity. She had perky tits and a thick ass that just begged to be grabbed. We had been dating for a bit and despite my shyness, Kristen initiated the physical stuff. We were making out in her parent’s basement, which we did often, when she just reached into my pants. I remember how it tickled as her hand slid over my lower stomach and below the waistband. These were the scene days so my pants were pretty tight, super slim fit, so she really had to put in some effort. I was semi-hard already, obviously, but I remember when she broke lip contact as she got her hand around my member. Her eyes widened and she started to freak. “Fuck! Donny, this is big!” she paused, but didn’t let go. She stared at me for another few seconds, and then “Pull it out, oh my god…”She helped me maneuver out of those awful pants (what the hell was fashion then?!?) and once it was free, my penis went as hard as it could. She didn’t let go… After too many seconds, she took a deep breath, leaned over, kissed me hard, sliding her tongue into my mouth, and then did a fucking dive and stuck her mouth around the head…Well, she tried. See, Kristen was barely 5 feet tall, and my dick is about 8 inches, kind of thick, and she wasn’t used to opening her mouth that wide. She was surprisingly still a virgin. I wasn’t, but it had been a while because of teenage depression (yay…). Anyways, Kristen was horny, and ready to give me her V-card, but this was new territory for her. Still, she was determined, and started jerking me with both hands while licking and kissing the head. After a bit, she pulled her head up and slowed down the jerking, told me she wants me to cum in her mouth. I asked if she was sure, and she just got a devilish grin. This made me feel confident, so I started telling her what felt best.”Squeeze me a little more… and keep the tongue action on the tip of the head. Mmmm, jack it a little slower, pull a little more…” I knew she watched plenty of porn but damn, she had done her homework. It felt so fucking good but I had a brief panic as I felt that electric tingle start building. I can shoot a pretty big load, and I hadn’t jacked off that morning, so it was going to be a lot. I tried to say something to her but as I was about to pop all I could manage was a stuttered “ah baby are you gonna swallow?””Mhmm” she garbled without missing a beat, as she sped up everything just enough. I was panting and groaning, it was the best I’d ever felt.“Oh shit!” as I unloaded in her mouth, I felt her lips tighten around the head, and three strong shots quickly filled her mouth. My entire body jerked, which she wasn’t ready for, and she moved back as I started shooting more, losing her lip’s seal around my cock and cum shooting all over her chin and dripping onto her shirt. She was a cum covered mess. The hottest, sexiest mess I’d seen yet, still with both hands gripping my penis as she licked the cum up. She swallowed as much as she could, smiling and caressing my package.Still catching my breath, I told her I want to return the favor, but as I reached to pull down her sweatpants, we heard the footsteps coming down the stairs. I quickly stuffed my dick back in my pants as Kristen ran to the bathroom. I tossed her my hoodie because she didn’t have another shirt. I made awkward small talk with her folks while she was cleaning up in the bathroom. They asked if I wanted to stay for dinner, but I declined and said goodnight. Kristen walked me out to my car and whispered she wants to fuck ASAP. So I bought a pack of condoms on my way home and we planned to do it the next day.I was beyond ecstatic and could hardly wait. The thought of finally plowing my sexy piece of a girlfriend had me rock hard all night. I jacked off twice that night thinking of her. But things don’t always go as planned, do they?Sometimes big things don’t easily fit into small holes. I knew Kristen was probably going to be a bit tight, I’d slipped a finger in once or twice, so I brought some lube too, it was strawberry flavor. Kristen had the same concerns, so we agreed to take it slow. The foreplay was amazing, she really got off on sucking my dick (WIN!), and I was working her pussy up. She put the condom on me, then we both took some lube and applied it to the other. We were huffing and puffing in anticipation, but with her on her back, legs spread wide, I couldn’t get more than the tip into her pussy. I sat on the couch and she tried to climb up and slide down my pole, but it wasn’t happening. We agreed it was probably some nerves, and we would work at it, and pleasure each other in other ways until we figured it out. This is where I should have realized something though, as I pulled her bare ass to the edge of the couch to repay the oral she gave me the day before, and worked that pussy and clit with vigor, my dick didn’t soften at all, like not even slightly. It took me like, 10 minutes to get her to cum (with some help from her, showing me where to rub and then just taking over clit duty as I licked her with two fingers inside of her) and my dick didn’t let up even a little. I obviously didn’t realize then, and maybe my erection stayed so hard because I knew a blowjob was coming, but it was the fact sarıyer escort that I couldn’t go soft until I came, combined with bad punk fashion trends, that put me on the path of fucking Kristen’s mom.Kristen gave me a fantastic blowy as her afterglow waned, though more controlled and less messy than the day before (that babe could swallow, let me tell you, I always come a fair amount). And as we had about 2 hours after her school let out on weekdays before her mom would come home, we licked each other’s goodies every day and still tried to have sex, but that remained a challenge. It was maybe two weeks later that my life changed. I was never the brightest guy, we had run out of condoms. I always wore one when we tried to have sex, but considering that we couldn’t make that work yet, I didn’t restock. Plus, Kristen loved swallowing cum and getting facials that I figured I’d just pull out anyways. All that said, we were at it again. We had even started putting on some music to help the mood, and I had almost my entire penis head between her labias when she had to tap out. It was okay, we would switch to 69 or something, and this was further than normal, so we were happy, ready to cum, and determined to keep on trying. I started to pick her up to put her pussy over my face when she said she just wanted to rock my world. She got on her knees and started doing her amazing two hand jacking off while sucking and licking the head. Fuck she was talented.Remember the music we were playing? It was loud enough that we didn’t hear the footsteps of her mom coming down the stairs. I just remember moaning in pleasure, followed by the shock of hearing the door opening and her mom loudly gasping, and Kristen pulling my dick out of her mouth. No cumming today I figured, plus, y’know, we were probably in trouble.“Oh my god, Kristen, oh MY GOD! Donny, put your clothes on! Oh my god, Kristen PUT YOUR CLOTHES ON….” She was yelling pretty loud, “GO TO YOUR ROOM YOUNG LADY! DONNY PUT YOUR GOD DAMN CLOTHES ON AND… AND… KRISTEN GO TO YOUR ROOM!”Kristen grabbed her clothes and ran to the stairs, saying “shit shit shit shit.”In my head, I was saying “shit shit shit shit.” Seemed it would be awhile before we could try this again, if ever. Mrs. Sharff watched her daughter Kristen walk upstairs, then turned around wide eyed.“Why are you still… out, Donny?!?” she asked desperately. “I’m sorry Mrs. Sharff, I can’t get my dick in. The pants are too tight.” I had to have looked scared, trying to hide me dick from my girlfriend’s mom. I was rock fucking hard though; solid as a steel pipe, and I couldn’t hide it at full mast. Didn’t help that she was wearing a nice looking sundress. She was a bit older, about 60 I think? She had Kristen at 41, but stayed fit and had a lovely glow from her natural tan, but I had never focused on any of that before.She stared at me incredulously, “what the hell Don? I want you out of this house!”“I’ll go, but I can’t walk out like this, I’m sorry. It’s not going down.” She was pissed.“You need to leave Donny, I… I can’t have this. You need to go. Figure something out!”I wasn’t sure what to do, so I started jacking myself off. “I’ll try to be quick Mrs. Sharff.”“Fucking hell Donny, I didn’t mean like that!” she yelled, taken aback.“I’m sorry, I think I just need to cum, I’ve had this happen lately. If I cum, it’ll go down and I’ll leave” I stammered. I was freaking out and this was the best I could think of in such a weird state. I sped up while realizing I was staring at her still, wide eyed as I jerked off.Deadpan she remarked “Don’t make eye contact, this is weird enough. I don’t believe this.” She was still pissed it seemed, but she hadn’t left the room. Still being dumb, I moved my stare from her eyes to her chest. Her breasts were smaller than Kristen’s, and saggier, but for the first time, I realized I liked them. She was not pleased with my new staring direction and crossed her arms over her breasts. My eyes moved to her nicely manicured fingernails, then down to her legs. Her… sexy… legs? Was it the raging erection, and the stolen pleasure from being caught that had me at an otherworldly level of horniness, or was I really turned on by her mom? I kept jerking as she turned sideways, not liking my gazing of her legs. “Oh god Don, seriously?” as I now stared at her cute, tight little ass. She turned back to face me and asked, “Fine, what will help. I am so pissed right now, I need you gone.”“I don’t know. Would you touch me?” I asked between my heavy breaths, I was working hard. “Absolutely not” she quickly responded.“Can I touch you then?” but she started to open her mouth again, so I cut in, “or show me something?”She just threw her hands in the air, exasperated. “What, you want a little skin? Fine, here” and pushed her boobs together to exaggerate her cleavage tauntingly.“Can I just go be with your daughter then? Look, I’m really trying here. This is weird for me too,” I pleaded.“Damn it Don, what do you want, huh? What? You want me to touch your thingy? Okay, fine,” she said as she walked closer and let her fingers slide over the top of my penis, just once though. Fuck though, that was it. I was enamored by this 60 year old woman in front of me. That did it, I was dumbstruck and even hornier now, if that could happen. I pushed my hips forward, my face begging for her to touch me more. She pushed esenyurt escort me away but softly, and stole a glance at my junk.“Don, you are piece of work, or of shit, not sure yet. Sit down.” Her eyes started darting back and forth between my dick, my face, and the door. She closed the door to the room and pointed again to sit.I sat on the couch and she sat next to me, on my right. She leaned into me and reached her right hand over and gripped my penis. I could swear I saw a shudder as she touched me, and sharp breath she took. She wrapped her fingers around and started jerking me. I was shocked, confused, and the hardest and largest I had ever been. “That really is something,” she said under her breath as she kept working my dick with her hand, I could barely hear her. She had a good grip, and I was still all lubed up from messing around with her daughter. She worked me from the top to the bottom, and back to the tip. Her fingers and hands were older, wrinkled, veiny, but her bright red nails were perfect, and with her leaning into me I was over the moon, but didn’t feel closer to cumming yet. As her breathing got heavier, the hot breath on my neck, her warm touch, my dick out in front of and in the hand of my girlfriend’s mom, the girlfriend I desperately wanted to fuck but couldn’t because her pussy was too tight…! It was too much, I reached my arm over Mrs. Sharff’s head, my other hand grabbing and cupping her left tit, pulled her face to mine and planted a heavy kiss. It wasn’t returned.“WHAT THE HELL DONNY” Oops, my bad. She didn’t let go of my cock though, and I was still holding her tit. “That is too far, dammit. Dammit! Donny, you need to finish and leave, I’m serious.” She wasn’t as loud as before though. “What the hell will work if a handy doesn’t?”“Well…” I started, staring into her eyes. I put my hand on her cheek, “Mrs. Sharff, please listen. I can’t fit in to Kristen so she gives me head to make me cum, that’s what it’s been for a long time” I explained. She just returned my gaze, but her eyes softened. She gave the slightest nod and I slid my hand a bit behind her head, gently guiding her head down to my penis. She licked her lips as she lowered and took my penis further into her mouth than her daughter ever could. Her tongue work was better too, I should have came right then, but something held it back. She kept jacking me off too, working her hand and mouth in tandem. It was pure bliss: hot, wet, electric.She stopped to take a breath. “Strawberry?” she asked with a chuckle before taking me back in her wonderful mouth, then pulled off once more, “I like strawberries…” She returned to pleasuring me with her mouth and hands for a few minutes. She had briefly paused to catch her breath when I noticed my phone had a notification. Mrs. Sharff said, “Donny, this is… well this is something, but you still need to hurry. Imagine if Kristen came down to find us.” I nodded, and quickly opened my phone to see the text Kristen sent me saying she had a girlfriend pick her up because she was so shaken and was spending the night at her friend’s. She ended the text saying to call her later and hopefully her mom hadn’t beat me up too much. I looked up at Mrs. Sharff as she fixed her permed hair, always dyed a chestnut brown to hide the gray. She was obviously worked up, and fixing her twisted up dress. I stared at my girlfriend’s mom wide eyed, “She left 20 minutes ago, Rachel picked her up, she’s sleeping over there…”For a moment I thought Mrs. Sharff was mad again, as her expression was one of shock and surprise, and then she pulled me in and kissed me deeply. Our tongues danced as she grabbed my dick in one hand and my ass cheek in the other, pulling herself into me. I held her tight, running my hands up and down her back and ending up full palming both of her ass cheeks, reaching around and under and caressing her pussy through silky and wet panties. I had heard older women didn’t get wet but she proved that notion very wrong. We were both breathing heavy as we played with each other… it was intense.She pulled back from my lips, “Fuck me Don, oh god,” and pulled down onto the couch with her. I haven’t mentioned that this was a basement theater, the couch was deep and enormous, plenty of room for the fun we were about to dive into. I lifted her legs and pulled off her panties, revealing the most beautiful pussy I had ever seen. She was completely shaved, and small lines of liquid drops started running down into her ass crack. I went in face first. I had to taste this woman, she was everything I had ever wanted and didn’t even know. I licked around her twat, then stuck my tongue in deep as I could. Her taste was divine. She was moaning and squeezing my head with her soft, hot thighs. I then moved to licking her clit but as I started to insert my fingers, she stopped me. Pulling my head up by my hair she panted “Fuck me, not your hand, fuuuuck me. God, stick your cock in, don’t tease me anymore!”I positioned myself on top for missionary and slid my tip up and down her pussy lips a few times, then pressed in to enter her. I moved slow, scared from my defeats when trying to fuck her daughter, but I was able to enter and we both shook, breathing heavy, grunting, making guttural a****l sounds of ecstasy and id. I kept pushing in, further and further, until my balls were comfortably cradled between avrupa yakası escort her ass cheeks and my penis was fully in my girlfriend’s mom’s pussy. I gave one last push to be as deep and connected as possible, causing her to whimper in delight. I had never been with anyone that could take all of me. In pure bliss I started to rhythmically fuck her tight vagina, my penis perfectly lubricated from the lube and her spit and juices. I matched her movements best I could. The sex was sensual but carnal, and neither of us let up until I felt her pussy widen more and more before clenching around me.“Don’t stop, DON’T STOP! AHHHH!” she screamed as her entire body seemed to spasm in orgasmic bliss. I tried to adjust after some moments and she grunted in response, putting her hand on my belly to not move. I stayed there, buried in her pussy for another few seconds before she relaxed.I pulled out and helped her sit up. “I need all of you,” and helped lift her sundress. She helped me get it off and then undid her bra straps before I got the chance, then pulled me in for another deep French kiss. She pushed me on the couch, climbing over me and sliding down over my still rock hard dick. She began to ride me, I grabbed her tits and lifted my head to suck on her nipple as I fondled the other tit and switched off a few times before she tilted forward to kiss more. She rode me hard at first, and then slowed, with more back and forth motion than just vertical. It was bliss, it was all bliss and every so often between the kissing and fucking I would have the briefest realization that I was fucking my girlfriend’s 60 year old mother completely raw. It was mind blowing, but the sex even more so and I would quickly be pulled back into our carnal fuckfest. This was the hottest sex I had ever had.We tried doggy after, Mrs. Sharff’s ass was smaller than Kristen’s but bounced more, until I grabbed each cheek tight to really pound her properly. She was screaming louder than I’d heard yet and orgasmed again on my dick. I fell back this time as she came, my penis pulling mostly out and her pushing the rest of me out as her pussy contracted. I was covered in her juices. It was amazing, but she was getting worn out and asked to switch back to missionary. I got on top again, entered her perfectly shaped pussy, and we kissed passionately while I thrust in her and squeezed a tit here and there before kissing again. I slowed as she came a third time, but she told me to keep up the pace. “Mrs. Sharff, I can feel my balls heating up, I think I’m going to cum soon,” I panted. I had barely spoken after the sex started.She smiled, and between heavy breaths blurted out, “Finally!” with a laugh, and I kissed her again. She pulled my head up and said “I think we can drop the Mrs when you are inside of me, just call me Diane.”“Yeah,” I said back with a smirk. “I’m gonna cum Diane, I’m gonna cum, this feels so good.” “I want it, cum baby, cum for me!” she begged.And then another example of my dumbness, I realized right as I was about climax that I wasn’t wearing a condom and freaked again. In one quick motion I pulled my cock out of her lovely dripping pussy, started jerking, and shot 4 big ropes of cum across her body, with three of them making it to her face. She made a loud sound of shock as the cum hit her face. I moved over her and kept jerking my dick, dribbling cum across her belly, her tits, neck, and once I was aimed for her face, shot two more big splotches of cum, covering her face from the forehead, on her glasses, and in and around her mouth. I unleashed a flood, but all I can say is it was the hottest sex I had had at that point, with a ton of build up. Diane had her hands up to catch more cum, but I shoved my penis into her mouth and kept jerking. Another shot went right onto her tongue, I could feel her licking. As I came down from the most intense orgasm ever, I looked at her, covered in cum, looking shocked.“Don…” she paused, “I was not expecting that” she stammered, seeming confused. “I didn’t have a condom Mrs. Sharff, err, Diane,” and I trailed off, realizing what she meant.“I’m 60 for goodness sake, you could have finished in my pussy,” she said lightly. I thought I had upset her, but a cum covered smile ran across her face, and she laughed. “Next time, you can cum in my pussy. How often do you get to do that going bareback at your age? Still though, I have never in all my years seen a man cum like that.” After a minute to catch our breaths, she asked me to help her up, and invited me to join her in the shower to clean up. She rinsed herself off first, telling me I had to pay for her next perm because of all the cum in her hair. I got in as she was soaping herself up, and she started to suds me up. I pulled her in for a kiss, and we made out a bit before I turned her around and pushed my now hard again dick between her legs, up to her pussy lips. All she said was yes, and I fucked her from behind in the shower, but this time I did finish in her pussy. She was right, I had never done that without a condom and holy fuck it felt great. After the shower we kissed a little more before I got dressed and headed out. The entire experience changed my world, and made me realize my fetish for older women. At Diane’s request, I kept dating her daughter for a bit longer, and though Kristen and I eventually had sex, it stayed difficult due to my size and Kristen couldn’t handle it for too long. We split amicably, occasionally fooling around when she visited town during college breaks, but I kept sleeping with her mom whenever I could. I eventually started hooking up with other older women, and now I can’t get enough action from grannies and older MILFS.



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