That Breakthrough Weekend

In high school I joined the millions of kids from split households. My older sister had already left for college, so she was sad when my dad walked out of our Westchester County home, but her life didn't change much. Dad was a successful investment banker, with all the trappings: money, never home, and of course affairs. Mom was devastated, naturally. Because of his income, she'd become a stay at home mom, and therefore did well in the divorce. She took a job in her old career, public relations. Her years out of the workforce, however, meant she pretty much had to start in an entry level job, which affected her self-confidence, already battered by Dad tossing her to the curb for a younger, fresher model.

As in many divorces, I stayed with my mom but visited my dad every second weekend and more time during vacations and holidays. At first I didn't look forward to those times, but after I turned eighteen I discovered that my dad, having money, had young women flocking to him in droves--women not much older than me. And these hot women, all way out of my league, put up with an amazing amount of crap to be close to my dad's wallet, if not to him. The power of money to attract hot women was eye-opening. I had heard of that, but seeing it in real life was a revelation. Moreover, wherever we went, there were always more women than dad, so I had the pick of hotties who thought they could get to my dad through me. Once I figured that out, all I had to do was boost the illusion.

Teenage heaven.

My mom, meantime, seemed to be torn. On one hand my occasional absences freed her from constraints as she sought to resurrect her love life. On the other, she said she missed me. I missed her, too, truth be told.

Her various club and gym memberships and no job obligations meant she was in superb shape--firm 38C rack, flat stomach and beautiful heart-shaped ass. To my mind, she would have been a perfect MILF model if she wanted. However, mom was a strict and strait-laced mother, firmly persuaded of what's wrong and what's right. So, despite my fantasy fodder, she made sure I understood that mom was mom, and firmly out of reach.

Visiting my dad, therefore, presented hopes more realistic, as I learned to fly under the umbrella of his wealthy bachelor lifestyle. One of the weekends I was to stay with him and his live-in du jour, Allison, he'd been invited to a party with several of his investment banker coworkers and a bevy of these hot chicks on the make. Most men were single, or acted as if they were, same with the gals. Some came from health clubs, or friends of friends, but what they all had in common was youth and hotness. The party was catered, hosted by a DJ, and held in a penthouse apartment in Manhattan with an open rooftop for dancing, eating and whatever.

At first I was intimidated by the crowd, as I, just over eighteen, was younger than everyone else. Dad simply told me Mom would never let him get away with leaving me alone in his condo, and there'd be more than enough for me to do here, so I simply got dragged along. He was right--I apparently was the only male not a hedge fund manager, broker, investment banker or an unattached guy with a bursting wallet. The women must have figured I was one of those, and since I was younger than the others, I had to be more successful, and therefore worthy of throwing themselves at. Why would I try to talk them out of such crazy delusions?

Alcohol and drugs flowed freely. Since nobody else was under drinking age, nobody thought to offer me anything else, so beer was a given. At the door to the open rooftop patio were several bowls with pills of various colors and, gasp, condoms. In passing, I slipped several condoms in my pocket. Who knew? Little ole Gunnar might get lucky, and better be prepared, right?

We'd arrived a little late to the party, so everyone else was lubed up, and loud music was beating out on the rooftop. Although not a fan of the thumping beat or the noise, I did appreciate that it rendered conversation nigh on impossible--to introvert me a godsend. Dad and Allison disappeared into the gyrating throng, leaving me by myself to sink or swim.

In less than ten minutes Barbara, a brunette model or wannabe, introduced herself and asked me to dance. Well, asked might imply spoken words, which were impossible in the din. All she did was flash her body and hold out her hand. And what a body! Slim and tall, she wore a short black stretch tube top, short black skirt, and little else, exposing acres and acres of flat tummy and legs. Flinging her body and head around, hands in the air, to the thudding beat, she flashed her prominent nipples and even her G-string as if auditioning for a spot in my next porn movie, or hoping to get a car of her own, maybe a college education paid for by a sugar daddy, or access to a fortune in the divorce. I couldn't help getting hard at her wanton flashing of her sexy body at me. Not in my wildest dreams had I imagined anything like this. Being a fringe member of the nerds, at school parties I had no shot at the cheerleader crowd or the hotties. This, though, was a radically different world. These ladies made our high school cheerleader "in-crowd" look like plodding mudhens and waddling ducks.

After a few dances, Barbara moved on to the next candidate for sugar daddy, to be replaced by Heather (I think that's what her name was), a blond health club honey bee wearing an LBD with the emphasis on the L. Like the previous honey, she, too, was slim, emaciated to perfection to quote the guy who wrote Bonfire of the Vanities. Her LBD neckline plunged to below her belly button, which she carried off with her marginally exposed taut B-cups. When she leaned forward in a dance move, she hunched her shoulders to reveal her hard nipples, and when she turned around, she backed in all the way until she made sure Little Gunnar was standing at attention and saluting her fully.

The music slowed after a few dances, and Heather plastered her lithe body to mine, arms across my neck, wide-pupil eyes gazing into mine while grinding against the steel in my slacks. Halfway through the first slow song I took a chance and started kissing her while my hands had a full grasp of her tight health club buns. Her tongue instantly invaded my mouth with determined abandon. We danced toward a dark spot at the edge of the rooftop where the owner had dragged his mini-forest of potted shrubs and trees to clear space for the dance floor. After a few more songs of vertical making out, Heather seemed ready for more action, and what horndog would deny her? My hands drifted below the hem of her skirt and groped their way up the back of her thighs to her, gasp, naked toned ass. No panties! I sank two fingers into her shaved treasure and they slid in with no resistance. Our tongues kept dueling and her body began undulating as her first orgasm overtook her.

I led her in the darkness to the roof's railing, turned her over it and, after rolling on a condom, slid my steel into her. She was so wet I slid in all the way in one thrust. Her hands stretched along the railing and her slender body bounced off it as I pounded into her, still shaking my head in surprise. Remembering something I'd seen on a porn video, I grabbed her hair and pulled her head backwards. Her mouth was wide open and her eyes closed as she surrendered to her passion. After fucking her for several heavenly minutes, her pussy spasmed around me, and as I spurted into the condom, her eyes rolled back into her head and she collapsed on the railing. For a moment I feared she might topple over, so I pulled her back and lay her on one of the plastic chaise lounges parked in a corner.

Holy shit. I wondered if the gal was high on something, just drunk, or both. We hardly even knew each other's names.

I needed a drink, so I left her there to give her some space to recover in privacy and went back inside. Armed with a fresh cold beer, I headed back out to the roof when I almost ran over Allison, my dad's girlfriend. She sat in a corner, head in her hands and tears running rivers down her cheeks. I sat next to her and put my arms around her shoulders. "Hey, Allie, what's the matter?"

When she saw it was me, she fell on my chest and grabbed my hand. "Your dad just fucked Brandi right before my eyes, like I wasn't even there."

"Come, let's get away from the crowd." I took my stepmother's hand and wandered inside, in search of some privacy and a little less noise. I opened a door, but closed it when I saw a girl being spit roasted with her minimal clothes still on. Three doors down, the room was empty. How many bedrooms did this apartment have? I shook my head--my dad lived in a world I had no clue existed. Anyway, I lay down on the queen sized bed and tapped my chest. Allie lay down next to me, put her head on my chest and continued bawling, eventually slowing down to mere sobs. So, these hot little bimbos had feelings. Imagine.

I held her and patted her back gently. What else was I to do? It's not like she was my girlfriend or anything. When the sobbing subsided, my stepmother lifted her head. "Do you think he's done with me? Or is this just a one-party fling?"

I shook my head. "I have no idea. You have to remember, I knew him as a husband and father for 18 years. In that time, I have no idea if he had any affairs or not. Our first sign was when he walked in one day and said he's outta there.

"But let me ask you this. Even if it is a one-party fling, how do you feel about it? You have to know if he does it once and you take him back, he'll do it again."

"You're right. Thank you for being honest with me." She settled back on my chest and I kissed her forehead. She lifted her head again, this time with fire in her eyes. "You know, fuck him. If I mean that little to him, then fuck him." Then, to my shock, she leaned forward and kissed me on my lips. Her tongue parted my lips before I could catch my breath.

Being as red-blooded as the next guy, I let my hands cup her thong-clad ass as my tongue joined that party with all the gusto I could muster. We rolled over 'til she lay on her back. To test how serious she was, I took one hand and cupped her breast.

She only moaned and kissed me harder. I squeezed her breast and pinched her nipple, and got an even stronger response. Was this girl looking for a revenge fuck? Well, okay. What's the worst that could happen?

While still kissing, I let my hand drop to her naked thigh and slid it up slowly under the hem of her skirt. Again, the only response was her spreading her legs as wide as she could. For panties she had on a minuscule little thing, more like a G-string. I rubbed over it, sliding my hand over her clit and her parting lips. More moans. This was happening. My wildest day, with no warning.

Still kissing like crazy, I slipped two fingers past the almost non-existent string of floss and into her now-slippery pussy. No pubic hair. I idly wondered if any women under thirty still had hair there. Focusing back on the task at hand, I buried my fingers and began stroking in and out.

Her moans turned louder, and she broke our kiss to start giving me instructions. "Almost there, Gunnar. Yes! Like that! So good... Faster. I'm... aaaaaaaaah, fuuuuuuuck!! Shuddering repeatedly, she came. Her body vibrated like five thousand volts were coursing through her.

As she came down, she looked at me. "Thank you, my friend. I really needed that. But you didn't get anything out of it. Fuck me. Take off my panties. I want to feel that big stick of yours in me. Help me get over your sonofabitch dad; make me yours."

I wasn't sure I wanted her to be mine, but whatever, no way I was passing on pussy. Grabbing another condom, I slipped off my pants and underwear and rolled it on. Then I got rid of my other clothes, rolled between the legs of this horny hottie stepmom and simply fucked her. Unlike the more passive Heather earlier, Allie was alive. It was almost as if she was venting her anger by fucking me from below. She pounded upward angrily, matching me thrust for thrust, grunting and chanting all the way.

In less than five minutes, she got into another vibrating orgasm, but I just kept pounding. After my earlier peak with Heather, I knew I was going to last. And I did. I pounded Allie through two more climaxes, until I finally came again.

She literally wilted as she came down. Between exhaustion and the misery of being dumped, she wilted like a flower.

I pulled out and gently kissed her. "Allie, he doesn't deserve you. Move on. You're beautiful and young. Guys will line up around the block to have a chance with you. Thank you for a wonderful evening together."

Tears formed in her eyes and she hugged me. "Thank you, Gunnar. You are a wonderful young man. I know you'll find the right woman, and when you find her I know you will treat her right. Thank you for indulging a jilted slut."

"Allie, you're anything but a slut. I think you're an awesome woman. Where are you gonna go tonight?"

"I don't know, I haven't thought about it."

"Come home with me," I said. "When dad comes home you'll find out the lay of the land. Worst case, you can sleep with me. I can think of a million things worse than that."

She chuckled. "Okay, let me get dressed. Maybe I can pack and leave before your dad makes it home. I'll call someone on the way home. Good thing I have tons of friends."

As it turned out, my dad didn't even make it home that night. I helped Allie pack and took her to a friend's house. How she worked it out with my dad wasn't my business.

I was alone when my dad arrived back the following morning late, this time with another hottie, I presume the one he left Allie for last night. I said nothing, just kept playing video games like nothing happened. He looked like he was into his new girlfriend and I asked if it would be better for him if I went back home. The relieved look on his face belied his neutral response. So I packed up and left.

--

When I arrived home, it was empty. I parked the little roadster Dad bought me in Mom's attached double garage, so when she returned, she would know I'm back early. I went up to my room and crashed, leaving the door open, so she wouldn't knock and wake me. The party and drama (code for sex) left me exhausted. I wondered about Allie. I never thought to get her number, so I couldn't stay in touch.

I awoke with the lovely smell of dinner floating into my room. Stumbling down into the kitchen, I saw my hot mom bustling and bending, getting stuff in and out of where they needed to go. Despite my sexual marathon the day before, her slacks drawn tightly over her full and sexy ass immediately got Little Gunnar straining against my underwear.

"Hmm, smells nice, Mom, what's cooking?"

She dropped her oven mitt and rushed over to me with a big hug. "Hey, Gunnar, to what do I owe the pleasure? You're supposed to be coddled in the lap of luxury with your famous father."

"Yeah, well." I kissed her cheek while pulling back my lower body to keep (now) Big Gunnar in witness protection. "Dad and Allison broke up, and he arrived home with a new catch, and I just felt in the way. Besides, he can't cook like you." I didn't add that ogling her in her tight outfit was a nice side benefit of my decision.

"I wasn't planning on cooking anything fancy, but when I saw your car in the garage, I turned right around, went shopping and here we are," she looked at the kitchen clock, "about twenty minutes from eating. Would you mind fixing the mashed potatoes in about fifteen?"

She knew it was my favorite kitchen job, because I had the freedom to add as much butter as I wanted. And I wanted a lot. Always. I couldn't tell her that wasn't all I wanted. "Hey, don't change your plans just for me. I'm totally happy to just sit and play games or whatever."

"Oh, well. I've already called the President and one of our State senators to beg off our biggest fundraising party of the year, and told them to send the President of France back home, because I can't make it anymore--my son came home unexpectedly."

We laughed--I always loved her sense of humor. I dropped my eyes to her full rack for a brief moment and said, "So, you told Bethany she's got to chase tail alone tonight."

Shaking her head, she grinned. "Not even that. We were just going to grab a bite and go to the movies. But you're a much better to-do, and she understands."

Wait, was she flirting with me? My super-prim mom? And was that a a glance at my crotch before the wink? I moved to stand behind the kitchen island to hide the incriminating evidence. "Well, I tell you what: after dinner, why don't you go fix yourself up and we can go dancing at the Troubadour?"

"What? Really? You don't have to do that for your old mom."

"'Have to' has nothing to do with it; 'want to' is the proper term. When's the last time you went dancing with no agenda other than a little exercise?"

She walked around the island, reached up and planted a warm kiss on my cheek. "Well, okay, if you absolutely insist. Shall I call Bethany and ask if she wants to join us?"

"No, this is just you and me. Our first date."

She looked at me a little funny. "What do you mean by that?"

"I'm now an adult, and I want to take out the most important person in my life, for the first time. I think you're beautiful and I want to spend time with the most beautiful girl in town. Unless you'd rather just sit around and eat popcorn."

"Okay, buster, I think I'd like that." She tested the potatoes with a knife. "I think these are ready. Do your thing, but stand over there; I need to get the chicken out of the oven."

After dinner, we put everything into the dishwasher, and headed to our rooms to get ready.

--

The Troubadour was an easy-listening piano jazz bar with a live pianist on the weekends. Very much the opposite of the previous night's up-tempo bumpa-thumpa noise orgy. Neither was really my scene, but I wanted to show my mother a good time. Being dumped unceremoniously by her husband had hurt her deeply. To my knowledge she never dated or put herself out there to find another man. But I knew from comments by her friend Bethany she was still a woman 'with needs.' So I thought if we hung out at the easy bar, a guy would hit on her, and who knows?

When she came down the stairs, my mouth dropped. She definitely had not lost it. Dressed in a tight dark green dress made for dancing, she looked stunning. My mother had never presented herself as a sexual being, or was it last night that had opened my eyes to many things? I couldn't help getting tight in my groin when I looked over her body.

"So?" she said with a shy smile as she twirled for her son. "Think they'll throw me out?"

"Oh hell, no. They'll start charging the guys admission just to look at you!" I exclaimed.

With a laugh, she threw the keys to her Lexus at me. "Okay charmer, you drive."

--

We were fortunate to find the last table at the edge of the dance floor. More to parade her before the gathered male clientele, I took her out on the floor after placing our drink orders. With a shock, I realized I had never danced with my mother before. She fit perfectly in my arms and moved with the most natural grace and ease; you'd swear we were partners in a (slow) dance contest. Totally amazing. Not only did we sway together easily, but we fit like we were made for each other. My mother was the cliché stone cold fox, and the natural ease with which we danced put a giant smile on her face. "Gunnar, you're a natural. Have you taken dance classes I don't know about?"

"No, I guess we were just made for each other." I gave her lips a soft peck. "You are stunningly beautiful, I can't say that enough. You're making me so proud by being my partner."

She blushed and pressed her body into mine. "Charmer."

"You know me--I call it like I see it. Don't be surprised when we sit down and men stand in line to dance with you."

It wasn't exactly a line, but she did have a steady stream of dance requests. A few times couples would come over and I would dance with the guy's wife--not something I'd heard of, but apparently it was a thing in this club. All civilized and decent. Despite my misgivings, I had a really good time, and my mom's constant smile told me she did too.

As the evening progressed, she had several drinks. With the dancing she obviously didn't keep count, but I could see her getting progressively more giggly and flushed. I guess some of her partners had pressed their peckers into her. She was flattered and, who knows, maybe a little turned on? I decided to join in, and the next dance, another slow one, found my mother dancing tightly with me. My cock was hard as steel and, unlike earlier, I did not hide it. In fact, as I felt her press into me, I squeezed Little Gunnar to let her feel what she was doing to me. She uttered a long sigh and laid her head onto my chest.

Then, taking a big chance, I lifted her chin to me and planted a light kiss on her lips. After her initial surprise, she pressed back softly. A few lines more into the song I rubbed my tongue along her lower lip while looking her in the eye.

Her breath caught, but she didn't protest, and maintained eye contact, almost as if challenging me to see how brave I was. As the song wound down, while keeping eye contact, she opened her mouth and met my tongue with hers. I almost exploded in my pants.

We stayed on the floor for the next song, still connected, like several other couples. As the next song flowed onto the floor, our kissing became more brazen and sexual. My hands drifted down her back and squeezed her ass, pulling her into me. Her only response was to moan softly and push harder. My lips traveled up her jawline and nibbled on her ear as we in effect made out on the dance floor.

I decided to amp it up a bit to test the water. "You are the sexiest woman in the room, mom. I want you."

She kissed me again, with total abandon this time. "Let's take this somewhere a little more private, son."

In the car, I let my hand rest on her thigh and she put her hand on it. This felt encouraging.

When we pulled in and closed the garage door, she leaned over. When we kissed, her tongue was in my mouth before I could even turn off the engine.

When the windows began steaming up, she broke the kiss and whispered. "My bedroom. Now."

In the bedroom the only light source was the night light and the glow from our street lamps. Compared to her, I had a closetful of clothes to get rid of. She stepped out of her sandal-type shoes, pulled down a zipper and stood before me, completely nude. My brain fried and I fumbled to get rid of my clothes. She reached down and stripped off my slacks and underwear. Little Gunnar stood at attention so hard it pointed at the ceiling, ready to fire its seven-gun salute at this hot woman.

She patted the bed for me to lie down, and lay on top of me in a 69 position, offering me her drooling womanhood to savor, while taking my titanium rod into her mouth and going to town. Softly I kissed her opening and ran my tongue through her folds. This was my mother, always so conservative, buttoned down and together, surrendering herself to me. Never in my wildest dreams did I imagine her such a wanton, wild woman. As my tongue split open her inner lips en route to her clit, she pushed her lower body down onto me, moaning around my hard dick.

"Finger me," she groaned.

While my tongue flicked across her clit, I sank two fingers into what now was her slick warm tunnel. I rubbed her g-spot as I slid my fingers in and out of her hot wet pussy, undulating with pent-up passion. A huge orgasm broke over her as she nearly decapitated me, clasping my head between her clamping thighs as she screamed my name.

Fortunately, she crested in time for me to gasp for breath from her unclenching legs. Not having come yet, I turned her around and flipped us over, so I lay on top of her. Lifting her legs over my shoulders, I plunged (now) Big Gunnar into her squelching wetness and began fucking her hard and fast.

She looked up at me with a huge smile. "My little boy is a man now. Show me. Ugh, that feels so good. Give it to me, baby, give it to me."

Always happy to obey my mother, that's what I did. "I'm getting close, you sexy thing," I gasped between grunts. "Come again, come with me."

Closing her eyes she matched my thrusts, until I exploded into her. Thanks to the two Manhattan hotties earlier that weekend, I had lasted far longer than usual, and I felt my mother's walls grasp me as my spurting triggered her climax, too.

Puffing and sweating, we lay together on her bed. As I regained my breath a little, I turned toward her. "That was without question the hottest sex I have ever had. I have no idea how Dad could walk away from this. There is no woman on this earth more beautiful and sexy than you."

"Thank you, my darling. Bet you had no idea your boring old mom had anything like this in her tank, did you?"

"Not a clue. But I am the happiest little clam on earth to make that discovery."

She pulled the sheet and a blanket over us, turned on her side and snuggled into me, pulling an arm over her shoulder and onto her soft, motherly breast.

Sleep overcame me as I dreamed about more nights like this.