Cumming Between a Mother + Daughter

Note to the reader: The daughter in this story, Rachel, is 18 years old.

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I think that every woman eventually reaches a point in her life where she realizes that the dependable and motivated man is much more desirable than the good-looking, vacuous, douche bag. Unfortunately for me during high school, I was the nerdy and reclusive type. Still very athletic—I could run a 4:30 mile and bench press more than my own weight—but getting a girl my age to notice me was impossible. They were too busy letting themselves be chased and fucked by those great looking douche bags that would never amount to anything. I told myself that high school just wasn't my time, and that I'd have to wait until girls—no women—found me attractive for what I was. Fortunately for me, an older woman found me in my teenage years and I've been lusting after them ever since, but that is another story altogether. At any rate, as I graduated from college and then grad school shortly thereafter, my career took off and women started to take notice of me—at client sites, conferences, even out with friends—and that's how I met Lauren.

We were both in Las Vegas; she was with a bachelorette party and I was with some old college friends living it up. I saw her from across the craps table we had joined (because inevitably a group of males in Las Vegas will seek out a bachelorette party). At only 5 feet 2 inches with 34D-25-35 measurements, any man would be staring. But it was also her deep, Latin brown eyes that could almost smile at you themselves that drew me in. It was her turn to throw the dice, and I quickly saw my chance. I put down several hundred dollars after her first roll (much more than a 25 year old paying back grad school loans should put down) in hopes that luck was on my side. After 44 consecutive rolls (indeed a hot streak), I was up several thousand dollars—and the noise from the table and those around us was incredible. After her last roll, a seven and out, the cheers died down but my friends understood my motive had nothing to do with money. I pocketed my winnings and walked over to her with a 500 dollar chip in my hand and said "I believe you've earned this." She smiled shyly at me—which I found almost unbelievable as most insanely beautiful women are anything but shy—and told me she couldn't accept it. After a bit of bantering back and forth I said 'May I at least buy you a drink?'

And that's when we found a quiet place at the hotel bar, just the two of us, and talked for hours. I discovered the reason for her shyness—she had been hurt too many times by men and always found that she ended up with the wrong one. Little did she know that at 33 and completely drop dead gorgeous, she was exactly my type and that I was exactly the type she was looking for—the stable and ambitious man who would finally take care of her as a partner—an equal. After several more drinks and sharing things about one another, she told me, in detail, about one of her high school relationships that ended badly—this one more notable than the others in that she became pregnant and soon thereafter a single mother. She looked at me to see my reaction, stating 'this is usually the part where you run away while you still can.' I smiled, and let my eyes drift over her gorgeous body—her long black hair flowing down to her neck, her luscious round 34D tits almost pouring out of a dress a size too small (she must have obviously borrowed from a friend). 'I'm not going anywhere,' I replied.

All trips to Las Vegas do come to an end and it turned out that Lauren lived in Miami. Not ideal as I was in New York at the time, but I did ask for her number and we talked several times over the phone and finally I worked up the courage to lie to her and say 'I'm actually going to be in Miami for work—we should get together.' She hesitated, but as I pressed her as to why not, knowing she wanted to see me, she explained that her teenage daughter never approved of men she dated and that she was certain that her daughter would an interpret a guy that she met in Vegas as the same caliber. 'Why don't you let me worry about that?' I said confidently.

By Friday of that same week I was I checked into a hotel not far from Miami Beach. As I was getting ready for my first date with Lauren, she called and asked me to meet her at the restaurant. I quickly realized that she hadn't told her daughter, but I decided that when the time was right, Lauren would be the one make the introduction. We ate, drank, laughed, and talked through the night and didn't even notice it was getting closer to 1am. Lauren, with her eyes wide, exclaimed that she must get going. I knew exactly why—past curfew, as far as being a responsible adult and role model to a teenage daughter who was left at home awaiting Lauren's arrival by midnight. We jumped in a cab and instead of dropping me at my hotel, I insisted that I would see her home. After all, I wasn't going to miss out on a first kiss. We pulled up to her house and I told the cab driver to wait. I walked Lauren up her side walk, thanked her for the wonderful evening, wrapped my arms around her tiny waist and planted an ever so soft kiss on her lips—feeling them gently part and her body slowly melt. I pulled away, perfect gentlemen that I was, and said goodnight. As I turned to head back to the cab, I couldn't help notice the one upstairs bedroom light on and blinds quickly closing as I looked up. This sneaking around Lauren's daughter wasn't a good start....

The next morning I called to see if Lauren wanted to get together, maybe go to the beach. I was dying to see her little body in a bikini; and there was no better place than Miami. Again, sounding hesitant on the phone and dropping her voice—'Rachel knows about last night. She doesn't know much about you, but she is upset—worried that I'm getting myself into yet another mess with some guy I just met in Las Vegas.' I told her I was coming over, and after her initial protest I assured her that I wanted a relationship with her—and that the only way that could happen was by at least introducing myself to her daughter and hopefully striking up a friendship with her. I hung up the phone, intent on winning over Lauren's daughter, but having no clue how to do so.

Arriving at her front door, I took a deep breath, and knocked. Any nervousness I had melted away as Lauren answered the door already attired for the beach—a light, low cut, button down shirt squeezed her amazing tits together with absolutely no bikini to be seen. My mind raced with thoughts of what could be underneath, by my eyes roamed over her luscious globes noticing the subtle blue veins towards the surface of her skin. In an instant I pictured the throbbing veins on my cock as I pressed it between her tits. I quickly remarked how gorgeous she looked—a playful glance from her letting me it was okay to look as she took my hand and led me into her house. Walking behind her I could not help but notice the short, flimsy skirt that she had on that I swear would upend itself at the slightest breeze. Once again I found myself wondering what must lie beneath.

She walked me into the kitchen, a young teenage girl eyes intently buried in a copy of Candide by Voltaire pretended not to acknowledge my existence or her mother's—much to Lauren's chagrin. 'Rachel put the book down and say hello to Thomas.' She looked up, at me, and but for her Latin brown eyes—the exact same color as her mother's, I don't think I would have recognized both Lauren and Rachel walking down the street as mother and daughter. At a lanky 5'7 and with a much paler complexion than her mother's olive skin tone she almost looked liked Lauren's distant cousin. 'So you're the next guy I see.' She said after surveying me for all of 5 seconds and resuming her book. 'It would appear so—everything is as it should be.' I said with a wry smile, knowing the book she had in her hand quite well. At this, she finally looked up at me and I knew then and there how to win Rachel's approval. At a young age, she saw her mother struggle and continue to date the ignorant douche bags and she vowed to live differently—to use her mind. Granted, she was beautiful enough to be popular amongst all her high school class on her looks alone, but she knew that wouldn't be enough for her. She wanted more for herself, and more for her mother. In short, she was a nerd with ambition, and so was I in high school. After a 5 minute conversation on other Enlightenment thinkers I asked if I could borrow a book from her, explaining that I would need something to read on the beach. She said I was welcome to anything I wanted and as I was perusing through the stack in front of her I asked, much to the surprise of her mother, if she might like to join us at the beach. Lauren was even more surprised when Rachel nonchalantly replied 'sure, I guess I could use some sun while I read. Let me go upstairs and grab my things.'

As Rachel left the room, her mother threw her arms around my neck, bringing my lips to hers and kissing me passionately for the first time—a deep kiss that lasted as my hands trailed down her back, gently squeezing her round Latin bottom through her skirt and underlying bikini, my cock starting to bulge in my trunks, pressed between us. She pulled away with a devilish grin—but I had to let her know that I was more than an intelligent and stable guy that could build a rapport with her teenage daughter. I had to let her know that I wanted her. She went into the kitchen and packed a few things in the cooler as her daughter came down the steps in beachwear of her own. It was like a Sari—not covering her entire body—indeed her long and slender legs were very much exposed, but I had no idea what kind of body she had underneath. I shook the though from my mind and soon we found ourselves at the beach.

It was sheer agony setting up an umbrella, laying out the beach towels over the white sands—I kept longing to see the bikini Lauren had on underneath her flimsy button down and skirt. What is more, I think she knew what sort of agony she was putting me through by taking her time. I whipped my shirt off, revealing, might I add, a very toned physique complete with flat stomach—not an 8 back, but at least 4. But my eyes were ever on Lauren as she slowly undid each button... Eternity ensued until at last she slid the light button down jacket down her arms falling softly onto the sand. Only two small triangles of solid black, connected to one another and around her neck and back with flimsy white strings remained. Her heaving 34Ds were perky and needed no support from the bikini—and it even looked as if they would not be contained within the tiny material and my thoughts immediately went back to how stunning she looked in that dress in Vegas—maybe it was one size to small, but I was beginning to think it wasn't borrowed from a friend at all, but intentional. She didn't stop there, as she hooked her thumbs into the waistband of her skirt and slid it down her legs, kicking it off. Every man within site was staring and I will readily admit I was, but I quickly remembered my surroundings, and that her teenage daughter sitting on the blanket opposite me. I quickly glanced over at Rachel and noticed that she too was looking at her mother, but her focus then zoomed in on me for a few seconds—trying to see my reaction. I tried looking out at the beach, pretending not to be at all interested in her mother's gorgeous 34D-25-35 body and praying to god that my trunks wouldn't start bulging right then and there. Lauren sat down, laying back on her elbows and soaking up the sun like the goddess she was.

Then she turned to me and said 'Oh! I forgot to put sunscreen on before we left the house, would you mind Thomas?' Rachel quickly interjected 'I brought some Mom, you should really wear a higher SPF.' And she promptly sand down behind her mother, rubbing it into her skin.

I thought to myself 'So she wants to be friends, but can't stand the thought of me touching her mother? This won't do...'

Lauren closed her eyes as Rachel finished her neck, back, shoulders, and then handed the bottle to her mother who gave me that same devilish grin as she poured some down her tits, letting it cascade between them down onto her tummy. Then her hands start to rub her breasts, squeezing them together, and rubbing them several seconds after the lotion was completely applied. I couldn't help but think to myself what a naughty fuck she was going to be if she was willing to tease me like that in front of her own daughter. I genuinely thought that my bonding with her daughter put her into sexual overdrive. Again, trying not to keep my eyes glued too much to her mother, I looked at Rachel, sitting directly behind her, watching her mother's every move; her eyes behind sunglasses but with what seemed a look of disapproval. She quickly stood up, removing her sari wrap asking for Lauren to rub some on her. I was immediately struck by the similarities between mother and daughter now—past the Latin brown eyes I had thought them not even remotely related—a 5'7 blonde with a slim frame couldn't possibly be Lauren's daughter. But as Rachel stood there in her much more conservative bikini (by Miami beach standards) she had the same body type as her mother—albeit a younger 34C-25-36 on a much taller frame. She sat down in front of her mother as Lauren applied copious amounts of sunscreen to her daughter's neck, back, and shoulders. 'She has such light skin' Lauren commented as I watched her apply it liberally—Rachel almost enjoying the attention she was receiving solely because of the lack of attention her mother was giving me. I decided to take the moral high road and apply my own sunscreen, grumbling to myself internally.

After that, the three of us talked, ate a light lunch from the cooler, and I even made a special point to converse with Rachel about intellectual subjects that were on her mind—I know how lonely high school can be when your intellectual stimulation comes from individuals who have been dead for over 300 years. She responded to me quite well and Lauren sat smiling, knowing that the two of us were going to get along just fine. As for me, I was genuinely enjoying the conversation with Rachel, but I was glancing at her mother thinking of all the naughty things she was going to do to me now that her daughter finally approved of a man she was dating. She could let down all those barriers she's had for years and I desperately wanted to know what kind of wildcat was behind that wall—and if I could possibly tame her with my cock. Something told me the answer was 'no' and that just made me want her even more. What I couldn't understand is why Rachel would be so warm while talking to me, then so cold as soon as my attention drifted to her mother.

As the sun was setting, we made our way back to Lauren's house. She made a light dinner and just the two of us had wine out on the patio—Rachel making her way upstairs to her room. We talked for hours, falling in love a little more with each passing minute. Lauren commented on how her teenage daughter, with how intelligent and wise she is, has never liked a single man she's dated. I shifted the conversation to us and how I had fallen for her and how I had wanted her—right now. I grabbed her wine glass, setting it down on the table and grasped her hand, leading her upstairs.... 'Show me your bedroom.' She smiled that same shy smile I saw when I first met her, but I kissed her passionately on the lips, pulling her body against mine, letting her feel how hard I was. She melted in my arms, much as she did on her first kiss. She quietly grabbed my hand and led me up the stairs to her bedroom, closing the door behind us.

We kissed again, this time our mouths finding the napes of each other's necks, my tongue nibbling on her ear while she grasped the bottom of my shirt, lifting it up over my head. I quickly did the same to her light tank top, only the clasp of her bra separating me from my prize. With that same naughty grin on her face that she gave me at the beach, I thought I was in for another tease but she quickly removed the clasp of her bra and let it fall to the ground. At last, her magnificent, 34D, naked breasts in front of me—and they were worth waiting for. Her nipples were already rock hard, her areolas perfectly round and maybe an inch in diameter. My hands gently cupping them as my eyes looked up from her tits into hers, silently asking if it was okay. She just smiled and kissed me, my hands gently kneaded her breasts, gently squeezing her nipples between my thumb and forefinger. She moaned softly into my ear, breaking our embrace to tell me that we had to be quiet. Rachel was only in the next room over and that anything above a whisper and she would hear. I assured her that her teenage daughter in the next room wouldn't hear a peep from me, but, with a fiendish grin of my own, I said I would not be able to guarantee that she wouldn't be able to hear her own mother. Her eyes wide with lust and fear, I grasped her by the waist and pushed her onto the bed, tugging her skirt and panties down with my fingers. Bending low, and looking up into her Latin brown eyes with my own Aryan blue I let my tongue drag up and down her completely bald, wet slit. She cooed with delight, 'It's been years since a man as licked my pussy' she said in a hushed voice, but still well above a whisper. My tongue breaking away while my forefinger gently circled overtop her clit, only long enough to ask her 'insinuating you've been with a woman?' She laughed as I gently blew softly on her pussy lips, 'Why is ever man obsessed with two women together? It's just a phase all teenage girls go through—experimenting their sexuality with one another. It's perfectly normal and my high school girlfriends and I used to lick each others pussies.' she said softly as she laid back, propping herself up on her elbows—her perky 34Ds in plain view as I resumed eating her pretty little bald pussy. Her eyes rolled back in her head in sheer ecstasy as I parted her pussy lips, sliding my middle finger deep inside her as my tongue continued to roll over top her exposed clitoris. Propped up on pillows now, her hands start to caress her tits, squeezing her nipples while reaching a crescendo, in almost perfect rhythm of my finger sliding deep inside her, my tongue quickly flickering over her clit. The moans escaping from her soft lips with each passing minute were also increasing in volume—well past a whisper, but it didn't matter—Rachel was listening intently through the wall from her bedroom from the very beginning...

Her mother had never brought a man home with her before; she would always just return home, hair a bit disheveled and Rachel would know. With her ear pressed against her paper-thin bedroom wall she listened as they kissed and touched, knowing his hands must be cupping and kneading her mother's breasts—she understood his desire from the very start, his reactions at the beach on affirmed it. Rachel had already slipped on a tasteful babydoll nightgown that she loved wearing—practical for sleeping and it made her feel sexy. Her mother even started calling her 'babydoll' because she wore it around the house so often. It was already a couple of years old, her 'go-to' outfit for sleepovers with other girlfriends in her earlier teenage years. She had grown since then—taller so that it barely covered any thigh at all—she loved the feel of the hem lightly touching her bottom. She even wore thongs with this babydoll so she could feel the material on her barely covered bottom. Her breasts had also grown—she went from a 32B to a 34C almost overnight last summer, her tits almost pouring out the top, the straps strained to contain them. She knew they weren't as big as her mother's, but she loved how she looked in her babydoll, imagining that her breasts were just as desirable. 'It's been years since a man as licked my pussy,' she heard through the wall, her ears picking up every word between her mother and Thomas, her pussy slowly soaking her thong. She knew she shouldn't be listening in on them, but she let out a soft moan as she cupped her hand around her pussy through her thong and rubbed her palm gently over her clit, putting her ear back to the wall just in time to hear her mother say 'It's perfectly normal and my high school girlfriends and I used to lick each other's pussies.' Rachel bit her lower lip, trying to stifle a moan as she closed her eyes and pictured Thomas between his mothers thighs, licking her pussy with reckless abandon—and probably better than any high school girl could do.' She decided that she couldn't take it anymore, that she needed to see for herself.