So, before I start, I want to say thanks to all the support I've received. Your guys' messages are super awesome to read. With that, I want to announce that there WILL be a PART 6 to this story. There was another important event between us that I want to share with you guys. This is gonna be a long one since I have a lot of info to get out in two parts. PART 6 will be the part to close this story out so I can move on to some of my other interesting experiences. Hope you enjoy!
"About the other night...it can't happen again," she said to me as I stood, nervously, outside her door. It was a few days after my super hot three-way that wasn't a three-way. I hadn't seen my MILF since that night and it worried me so I had knocked on her door to talk to her. "I was horny and in the moment and I wasn't about to come out there and stop you. But we agreed on the rules yes? So it won't happen again and make sure you know where to draw the line when Kaitlyn is here." "Of course, I'll be more responsible," I said. "Ok, don't worry, we're good." She put her hand on my face and kissed me. Still holding my face, she said," come back later. I've got some outfits I want to try on for you." Things were going to be ok.
Fast forward to the week of Thanksgiving of 2015. Things were more serious between Kaitlyn and I, we'd officially become a couple around the beginning of November. But when I wasn't going on adventures or clapping her phat ass, I was porking my insanely fine, 41 year old MILF. When I say her sex drive was insane, I mean like the Joker insane: no matter what I did, her sex drive would break out and we'd go again. Thankfully, I was still young and had the stamina to match hers. If Kaitlyn had the same drive and we'd had more time together, my nutsack would've become more shriveled than it's supposed to be. Kaitlyn was the romantic part of my life and the sex I wasn't having with her was more than made up with my MILF.
As a respectable boyfriend (am I though?), I met Kaitlyn's family, even spent some weekends throwing some BBQs at her home. They LOVED me, her mother especially. Barely a few weeks into dating, her mother had already begun to throw hints that Kaitlyn had always wanted to be married to "a respectable, handsome man such as yourself." Thankfully Kaitlyn always shielded these questions for me as I sat there, smiling and laughing awkwardly. Her younger sister (17 at the time but I remember her having an ass like her sister's) and older brother (never found out his age) enjoyed my company and got along well enough I considered myself always welcome. Her father was a different story: he was always friendly enough, but something about him let me know he didn't like me very much...which made stealing moments with Kaitlyn in his house that much better. We'd go into the kitchen to grab a drink or something and, with everyone in the next room, I'd shove my hand between her legs, feeling her heat up almost instantly on my fingers. Or I'd come up behind her and grab her tits while pushing my crotch into her ass, letting her know my intentions. She'd push me off, with a smile, jerking her head in the direction of everyone in the next room. But sometimes....a tiny moan would escape from her or she would push her ass back into my crotch. I would take her right there if possible but it never happened, more out of respect than anything. But the rush of possibly getting caught was amazing.
Two weeks before Thanksgiving, on a Saturday I think, Kaitlyn got news that her grandparents from Boston had passed away (a car accident). Of course they made plans to travel out there immediately. I offered to come with to be there for support but was rejected nicely. "My dad...you know?" "Yea, I know." "It's just they were so close and I think you being around would make him more upset." "I know, you don't have to sugarcoat it. It's cool." She was gone the next day.
My family had left to spend Thanksgiving in Mexico so I would be spending mine in Vegas...but not alone! My MILF was also staying cause she had to work. At this news, all the free time we had was spent having sex in every place we could think of where we hadn't yet left a mark. Outside by the pool, in the pool, on the exercise equipment, on the kitchen stove, on the washing machine...fuck, even IN the washing machine (you know that porn? Where they get stuck?) Eventually, it got to the point where a few days after Kaitlyn left, I wasn't even sleeping in my room anymore. I was staying in hers. To save those precious seconds from having to move from one room or the other. But the Monday before Thanksgiving, my MILF and I got a very unexpected visitor...her son/my friend Jonathan.
He had stopped to spend a few days with his mom before heading further north to Seattle where his dad lived. He was happy to see me of course and I was happy to see him too....but not so much. I know I was being selfish but him being there meant no more sex with his mom. We hadn't gone more than a few hours since Kaitlyn had left without doing something pleasurable to or on each other. Of course this meant I had to sleep in my rented room again....but I didn't let any of it stop from getting what I wanted. Like with Kaitlyn in her parents' home, I was stealing moments with my friend's mom when he was close by. To my immense pleasure, she didn't deny me my treats.
Once, we were watching a movie in the living room and she went into the pantry to "grab some snacks". She called for some help moving something and when Jonathan scoffed at the request, I jumped up immediately. "I got it bro, don't trip," I said as I hurried to the pantry. The moment I was inside and the door had closed behind me (the pantry door wouldn't ever stay propped open, it kinda swung shut on its own) I rushed forward and grabbed my "snack". We made out furiously as I slipped one hand under her shirt while the other grabbed a handful of her ass, pulling her closer into my rapidly expanding bulge. I kissed a trail across her jawline, down her neck, and over her cleavage before she pulled her blouse up, freeing her tits with that amazing bounce I had come to love. Not wasting a second, I sucked on her tits as if they were made of candy. I didn't know when I would see them again! As I sucked, I had moved my hand between her legs and had begun to rub her pussy through her tights. The heat coming from her pussy, I mean fuck, it was like the heat from opening the oven door! Her hand was inside my shorts, jerking me off over my boxers (I wore boxer briefs at the time so it would've been uncomfortable if she had tried to reach in to jerk me off).
We were stopped when Jonathan called," Can you guys grab me some chips? The hot ones?" We quickly jumped apart as if a lightning bolt had just struck between us. With her tits still hanging out, she quickly caught her breath (being athletic had its perks) and called back,"of course honey, I got it!" Not taking her eyes off me (and me not taking my eyes off her tits) she grabbed the bag of chips and placed it between her tits. She asked,"can you take these to him please?" I stepped over to her and slid my hands over her erect nippers before grabbing the bag of chips. She grabbed my dick through my shorts before I could turn to leave. "Don't you dare jerk off," she whispered," that's for me!" The commanding way she said it almost made me cum.
We had a few more of those stolen moments over the next few days. Whenever Jonathan would do something that would take him more than a few moments, such as a shower or a trip to the liquor store next door, we scrambled for a hot make out session or a blowjob or anything to quickly get off but we never risked sex. During sex, you'd miss some pretty important things cause you're so focused on the act itself. If we had sex, we ran the risk of Jonathan stumbling upon us. It'd be pretty hard to explain to my friend why he walked in on me balls deep in his mom, don't you think?
On the night before Thanksgiving, Jonathan wanted us to hit up the Strip to "get some bitches". His mom encouraged this but I couldn't figure out why. I worried she was so desperate to get laid she was rushing us out to bring someone else over as a substitute for me. As the night went on, however, I learned this wasn't the case.
We ended up at OMNIA at Caesars a little while later. My friend is a huge party guy so he got a VIP table with bottle service, all at his own expense. He was taking ME out for a night on the town. If anyone has ever been to OMNIA, you know the scene and what everyone does: dancing. It's a bit crowded on the dance floor but who cares when you're frequently being sandwiched between beautiful, sweaty women who want nothing more than to grind against your equally sweaty self. I ended back at my table with a woman named Tatiana (I remembered her name cause of a movie quote. "Its Tatiana...calls me at 3 in the morning and wants to fuck-stein, who gives a shit what her last name is" 100 points if you can name the movie). Tatiana wasn't insanely beautiful (in terms of beauty, maybe a 6) but she was well stacked in both departments. I mean, she jiggled in the best ways. Quick thing about me, yes looks do sometimes matter but at that age, I was more about body than anything. I have done some unspeakable things to some questionable looking women because they had a rocking body.
While Tatiana and I talked, I worked my charm (I had every intention of getting laid since I hadn't had any since Jonathan had shown up). My phone was going off in my pocket. I ignored it. Using the loud music as an excuse, I kept my head next to Tatiana's ear, so that she could feel my warm breath on her neck. Her hand rested on my thigh as we spoke. I took my chance and kissed her neck, working my way up to her lips. We made out for a few minutes while my phone continued to vibrate in my pocket. When we broke apart, she smiled and said," I'm gonna grab some drinks and we can continue this somewhere a bit more private." She left and I finally looked at my phone. I was stunned...
I had about 15-20 texts from my MILF; some were texts, some were pictures. She started out by saying how bad she needs me, how she can't wait for Jonathan to be gone so we can continue our "laycation". The rest of the texts were a mix of body parts and what she wanted to do with them. But the pictures...FUCK! They started out as lingerie shots and gradually worked into nudes. Stolen moments weren't enough and seeing these pictures drove any intention of fucking Tatiana out of my mind. Her last text (which had come maybe 5 minutes before I looked at my phone) shut off my head brain and fully activated my cock's brain; "I need you in my ass" (it was the peach emoji but you know).
No hesitation: I stood up and started to leave as Tatiana came back with our drinks. "Hey, where you off to?" "Work emergency, gotta save my job. I'll call you!" I wasn't even finished speaking before I was on my way out. I heard her call," you don't have my number!" Just as I reached the exit, Jonathan caught my arm. "Where you going bro?" "Work thing, gotta save my job." "Shit, want a ride?" "Nah man, I'll grab a cab. I'll see you at the house." He winked and said," I don't think I'll be at the house tonight, maybe in the morning." "Cool bro." I hopped into a cab in front of some guys who couldn't figure out who was going to pay for the ride. I told the driver," hey man, get me to [address] as quick as you can." I tossed him a hundred and, without a word, he took off. This guy must have been an extra on Fast and Furious cause the way he drove, I found myself gripping the seat and door handle as he wound his way through traffic. I think he might have even jumped the curb once. I texted her during the ride. "Omw home, Jonathan gonna be out late." "Hurry," she responded.
In almost no time at all, I was jumping out of the cab and running up the path to my front door. I was nervous: I felt like we were about to fuck for the first time again. I must have been making a lot of noise fumbling with my keys cause before I could get the right one in the door, it opened and I was yanked inside. My MILF didn't even let go of my clothes as she closed the door behind me, so I kind of boomeranged into her. She jumped into my arms and I caught her by her ass as she wrapped her legs around my waist. As we started making out (or trying our best to eat the other's face off) I realized she was completely nude. Her tits were pressed up against my chest, almost reaching my chin due to their magnificent size. I used my hands to tease her as I carried her to her bedroom, causing her pussy to start dripping.
She couldn't wait, apparently, as she reached down underneath her to undo my pants and bring forth my cock. I helped and, very quickly, my pants dropped, revealing my painfully throbbing cock. I looked down for a second before we crashed into the wall next to her bedroom door (behind the L-shaped couch, remember cause it's important), me pinning her to the wall. "Just here, like this," she whispered urgently. She was starving for it as badly as I was. (I'd always wanted to do this position) Still holding onto her ass, I leaned her against the wall while positioning her over my cock. I looked up into her face; she had a desperate look, her eyes were hungry, she was biting her lower lip in anticipation, and she was breathing hard. We locked eyes as I drove my cock into her soaked pussy with a satisfying squelch. It DID feel like the first time: every inch of her felt fresh, as if I had not been exploring her body for months. As I literally pounded her against the wall, I noted everything about her: the way her pussy contracted on my dick, the way she was shouting my name along with God's, the way her tits jiggled with each thrust, the way she smiled as she satisfied her NEED for my cock. "SHE'S MINE! THIS COCK HUNGRY BITCH IS MINE!" (That's not the way I normally think, I was just completely lost in the moment). All of it made my pleasure soar through the roof and I began to go faster, harder than I'd ever had before. We were grunting like animals, sweat and other bodily fluids drenching our bodies (she had begun to squirt and it was like a fountain shooting up from our crotches) but I kept going. I felt like I could've have kept up that rhythm for a year at least, but I had other plans for her.
To her surprise, I stopped, pulled out, and lowered her to the floor (standing not laying down). Before she could say anything, I shoved her over to the couch and bent her over the back of it. She knew exactly what I was intending, as I noticed that she began to spread her ass apart. I lifted her left leg and placed it on top of the couch, so as to give me more space to work with. I got down on my knees behind her and brought her starfish to my lips. Thankfully, I had lots of ass-eating practice under my belt thanks to Kaitlyn. My MILF's ass wasn't the dump truck Kaitlyn's was, so my face wasn't buried with no chance for air (which I find hot as fuck just to be clear), but it was definitely appetizing. A fruity, floral smell came from her asshole, it was like eating dessert. Her knees (the one I could see) buckled slightly as I plunged my tongue further and further up her ass. Eventually, I added a finger to carve up a bit more space for myself.
After indulging in my appetizer, I stood up and positioned myself for the main course; she looked back at me with anticipation for her serving of sausage. I started slow, as is recommended, but was caught completely off guard when, before I was even close to halfway, she lowered her left leg and drove herself all the way into my crotch, making me go balls deep in her ass within a second. The suddenness of being fully drilled into caused her to collapse across the back of the couch, shuddering violently. She went limp with pleasure, as evidenced by her ass sticking straight into the air and her arms hanging loosely at her sides. I might have thought she had passed out if she hadn't been breathing so hard. I grabbed her hips and went to pound town.
I didn't jackhammer away like a rabbit on steroids; I took my time. With each thrust, I pulled her into me at the same tine, making sure my cock was reaching the deepest part of her ass. She must have never done anal before because man...even the most (legal) virgin pussy in the world couldn't have been this tight. My cock was being squeezed so hard it was practically suffocating in there. She must have been feeling a mix of pleasure and pain for she was letting her moans and grunts come out with explosive breaths (if you've ever watched porn with Daphne Rosen, the way she moans, that's what I mean). I picked up her leg again and placed it on the couch. Now I felt like I was going deeper than before. I reached over, grabbed her ponytail by its base, and jerked her upright so that her back was completely arched while I continued to pound away. Her animal-like lust took over and she began speaking so dirty, I made a mental note to shower right after. "OH MY-- GRUNT FUCK MY ASS! COME ON! GO-- GASP FUCKING DEEP! DEEPER! MAKE MY ASS YOUR NEW CUM DUMP! GASP MAKE ME YOUR LITTLE BITCH! MAKE ME YOUR LITTLE-- GRUNT BITCH SLUT (whatever that means)! GASP/GRUNT" I don't know if I could have gone any deeper, I was so far up her ass, I couldn't even see my cock come out when I pulled back to thrust again. She came at least twice more while in that position (her face was so close to mine I thought she was going to take a bite out of my face from the pure pleasure of it) but I wanted a different one to bust my nut in her ass.
Still deep inside her, I pulled her backwards, guiding her to the floor. Obediently, she got down on all fours....I pushed her upper body closer to the floor while keeping her ass (which still had a tight grip on my cock) sticking straight into the air. Her chest and face were flat on the ground, I could only hear her breathing to let me know what she was feeling. I started again, slowly at first. Her moans were soft, almost loving but as I picked up speed they turned into growls and grunts of animal lust again. Her cheeks weren't even clapping; I held them as far apart as they would go so as to let me in as far as possible. My balls (hanging pretty low from the heat) were slapping a steady beat against her clit (yes, they were dangling pretty low), causing her to cum again. We were drenched in sweat by this point. My knees were sliding on the ground so much I had to use my feet to keep myself steady. Her tits were making small circles on the ground as she slid back and forth with each thrust. Her hair had come undone but it too was wet with sweat, so there was no point trying to pull it back again.
The slipping and sliding everywhere was hot but I was getting no closer to busting. I tried a different tactic: I let go of her ass and grabbed her hips, letting myself fall backwards onto my ass, bringing her along to sit comfortably on my dick. I laid on my back and said," bounce, baby." Still facing away from me she placed her hands on my legs, rested her legs at my sides, and began twerking a steady rhythm on my cock as if a Cardi B song had begun to play. She didn't even have to rock her whole body; she had total control and only bounced her ass up and down. The pleasure I got from watching her ride my dick with her asshole was crazy. I enjoyed the view: her ass twerking, jiggling on each impact, my cock spreading her tiny hole wider on each thrust, the way she moaned and yelled out with each slide on my flagpole. I could feel the fireworks starting to light in my balls. "Oh fuck, imma cum!" I called out. The Cardi B song in her head must have started playing at x2 cause she picked up speed.
BOUNCE, BOUNCE "fuck, her ass is still so tight!" BOUNCE BOUNCE "she's working my cock so hard!" BOUNCE, BOUNCE, BOUNCE "she's screaming so fucking loud! Imma fill this ass up!" These thoughts ran through my head as she rode me. In one quick motion, I sat up, grabbed her shoulders and pulled her against me as I blew my fattest load ever up her ass (I hadn't nut in a few days, following her commands of cumming only for her). She leaned against me as I shot a river hot jizz in the tightest space I've ever stuck my dick in. I grabbed her tits and, with each pulsating shot, squeezed them hard enough to elicit some deep, aching moans from her. We fell backwards, her on top of me. As we lay there, I could feel my cum leaking out of her asshole, down my shaft, and over my balls. I could also feel some other fluid running down as well; she had started to squirt as we fell back. I could hear her juices splashing the ground in front if us as she shuddered on top of me like a human vibrator.
When we both came down from our respective highs, she turned over, laying her awesome tits on my chest; my cock slipped out of her ass with a soft, slimy pop. With a small grimace, she said," I'm gonna need some ice for my ass tomorrow. It's gonna be sore for a while." "Yea, that happens when you get fucked," I laughed. "So, Jonathan's not coming tonight?" I shook my head. "I think he was planning on going home with someone." "Then...spend the night in my room?" she asked, with a smirk on her face, knowing my answer. We scrambled up, cleaned the mess on the floor, and ran to the shower in her room. In the shower, we explored each other's bodies while the steaming water ran over us. We soaped each other up: I spent a good amount of time making sure her tits were especially clean.
As I dried myself off after the shower, she walked to the door leading back into the bedroom. Opening it, she looked back at me, smiled, and walked away with the most seductive, sensual swing of her hips. My cock was instantly hard again. I dropped the towel, crossed the room in a few long strides, and picked her up from behind before she could reach her dresser. I tossed her onto her bed facedown and climbed up after her. Picking herself up on all fours, her ass sticking straight up, she looked back at and said," fuck me like your dirty cum slut." I happily obliged: grabbing her still soaked body, I slipped my cock into her swollen pussy and proceeded to rock her headboard against the wall for a few hours...
We were awoken by a knock on the bedroom door around 5 or 6 in the morning. "Mom?" Oh fuck! Still naked, I stood up and dragged her to the center of the bed before dropping to the ground and trying to be completely still. "Yea honey?" she called. I heard Jonathan enter the room. "You know if [my name] came home ok last night? He took off from the club for a work thing but I thought he'd be here by now." "I heard him come home but we didn't talk. It seemed like he came here to put some work in but then he left. Maybe his girlfriend finally got back?" "Maybe." "And where'd you go all night?" He laughed. "Out." She said, with a disapproving tone in her voice," you two need to choose your girls carefully. Find somebody who's nice and gentle. Not some little skonkas (street way of saying slut). I'm gonna get up now so get out of my room, or your going to see more of your mom than you'd like." "Gross," he said as he closed the door. I heard her get out of bed, cross the room, and lock the door. She came around to where I was still laying. "You should stay in here for a little while until he goes to sleep," she said. "What do we do till then?" I asked." With a smirk, she said," I can think of a few things..." I sprang to my feet and tackled her onto the bed. We slipped into the covers, where we did more than just a few things.
In my jeans, my phone vibrated with a text from Kaitlyn that I wouldn't see until later in the day. "Hey babe, Happy Thanksgiving. I miss you! I'll be home tomorrow night. I wanted to talk to you about something important when I get back...meet me at the airport at 8 tomorrow night. I love you " (it was filled with a ton of emojis but you know)
Thanks so much for reading! I know this one was crazy long but I had to get everything out to make sense. No, Jonathan never found out what we were up to. I probably wouldn't have any legs if he did. Sorry this one took so long to post. I don't have much free time these days so I could only write a little at a time. That and when I'm writing out the details of these memories, I get hard and need to handle business. PART 6 will be the last part! Let me know what you guys think so feel free to message me! Thanks for the support!
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