18yr old daughter and 40yr old mother go on vacation together.
There’s a saying you’ll all be familiar with, ‘like mother, like daughter’. Well, that was me and my mom. Although we considered ourselves to be more like sisters as I grew into an adult, the saying did describe us pretty accurately.
The good, the bad and the ugly. I developed my mother’s traits and followed her advice, and when she advised me not to make the same mistakes as her, I did anyway. So I didn’t always follow her advice.
My names Pippa and I’m a 5ft 5′ curvy brunette. My mother Annie is also a curvy brunette, but she’s two inches taller and a bit curvier.
When I was eighteen and my mother was forty, she booked a ‘girls’ holiday to Hersonissos, Crete. The apartment she booked was an adult only complex. Not that kind of adult only, you perverts! It just wasn’t family friendly.
Mom and I shared a two-bedroom apartment, and we joked about being able to bring guys back to our own bedrooms, but we pinky promised not to ditch each other for a guy. If we did meet any guys, we’d tell them we were sisters.
On that very first day we settled by the pool with only a few couples sunbathing. I was wearing a new khaki two-piece bikini and mom was wearing a new red halter neck bikini.
We quickly caught the attention of the men when we removed our cover up dresses, but let’s be honest, that’s standard anyway.
I took it in my stride like any other vacation. I didn’t feel sexy or self-conscious. The latter was only moments away though.
I’d already prepared my sun protection inside the apartment. Mother clearly hadn’t. Brazen as you like, she sat down on her sun bed, removed her bikini top, then started rubbing sun cream into her big boobs, whilst talking to me about an excursion she fancied doing later in the week.
From behind my sunglasses, I looked around the pool. All male eyes were on my forty-year-old mom rubbing up her tits with sun cream. I was so embarrassed I tried to hide my shame whilst agreeing to the excursion.
I didn’t know what I’d agreed to. I just nodded and squirmed on the sun bed beside her.
“Are you not joining me, Pippa? she then asked.
“What? Topless?” I whispered harshly.
My mother teased me. “You’re not embarrassed, are you? Has my confident Pippa lost her outward confidence all of a sudden?”
“No!” I sat up in defiance. I hated the way my ego responded to her at times, needing to be like her.
“You’re on vacation. There’s no jealous, insecure boyfriend to tell you to put them away, so embrace your femininity, Pippa,” she dared me. “Give those pale girls a suntan.”
My mom laughed quietly to herself and then sat back on her sun bed, with her legs sprawled out as she sat up and opened a novel. I could see her watching me out the corner of my eye, smirking.
Like mother, like daughter, I decided, I reached behind my back and unclasped my bikini top. My heart was racing as the men turned their attention from my mother’s exposed tits to watch me, her daughter, exposing mine.
Dropping my bikini top onto my bag, I sat back on my sun bed with my legs sprawled out and heard my mother chuckle into her novel.
“Reading something funny?” I asked sarcastically.
“Watch you don’t burn your boobs, Pippa,” she chuckled again.
Damn! I hadn’t thought about that. I wanted to run back to the apartment to rub sun cream into my breasts, but I knew I couldn’t do that, not really.
“You’re enjoying this more than the men,” I giggled nervously.
“For different reasons,” my mother grinned. “Forget them. Embrace your body and stop worrying about what other people think. Bikini or topless, men are men, Pippa. They’ll look and admire, stare and lust. You already know this.”
I cleared my throat and sat up, then leaned down into my bag for the sun cream. Feeling the weight of my full, round breasts as they fell away from my body, I felt the weight of the men watching me.
My mother was quickly into her novel when I squirted sun cream into my hands and began rubbing it into my exposed breasts. She didn’t smile, laugh or tease me.
Once I’d finished my nipples were rock hard and my pussy was drenched. I was now embarrassingly aroused.
My mother and I sunbathed topless by the pool everyday of the holiday. I even started applying my sun cream at the pool. It was a constant turn on for me, showing off in front of men with their wives and girlfriends sat beside them.
We only put our bikini tops back on when we went for a dip in the pool, or when it was time to leave. I left Crete with a lovely pair of tanned breasts, and a newfound level of confidence.
In the evenings, my mother and I ate out in restaurants. We wore our new dresses and turned heads pretty much everywhere we went. It felt amazing experiencing this with my mother, because I’d only ever experienced it with my friends.
Something else I noticed. The age of the men we attracted were a lot older than me. Whenever I was out with my friends, I noticed older guys getting a good look at us, but none ever approached us. I mean, we were in our late teens.
However, my mother was forty years old, so guys my own age rarely approached us during the holiday. The few that did were too immature and cocky. They left with their tails between their legs as their cheesy chat-up lines were no match for my mother. While some of them impressed me, she’d heard them all before.
On the last night of our vacation, we planned to party hard. My mother was well up for getting drunk and dancing until the early hours of the morning. It was music to my younger ears. We’d so far had an amazing time.
Long days sunbathing topless by the pool together. A picturesque boat tour around the island of Crete, and beautiful food and lovely wine in the evenings, until it was time to sleep and do it all again the next day.
My mother exited her room ready to party, while I stood in my bra and knickers, dithering over two outfits to choose from. “How do you always look so amazing, so fast?” I moaned.
My mother was wearing a stunning pink-dye-print cami dress. It was fairly low-cut, and it hemmed mid-thigh, showing off her bronzed thighs and cleavage.
Even her hair and make-up looked stunning in the time she’d taken to get ready. “You’re spoilt for choice. I told you not to bring too many outfits. Let me help you.”
My mother stepped up to the foot of my bed and looked over the two dresses I had laid out. “Go for the black one,” she picked out.
“It’s a bit risqué,” I mulled. “Even by my standards,” I quickly laughed.
“You’ll look fabulous. Tonight, we’re two ladies hitting the town for a bloody good time!” We laughed and I picked up the black dress. “Now hurry up, Pippa. Your mother is thirsty,” she smiled and softly patted my bum. “I’ll have a cigarette outside while you slip into your dress.”
While my mother smoked on the balcony, I stood topless in front of the mirror and stepped into the black, sheath, mini dress. It was backless and low cut, with a deeper V at the centre of the outfit, revealing my entire cleavage.
“Sex on legs!” my mother joked when she returned.
“Says the MILF dressed for cock!” I joked back.
“Watch your mouth, young lady! I’m your mother not one of your slapper friends!” she laughed.
Dressed in our newest, sexiest outfits, we grabbed our outfit matching handbags and set off for the bars of Hersonissos. It was to be an experience I’ll never forget.
As soon as we walked along the strip, bar staff were pulling us inside for their free shitty, mouthwash tasting shots. Bar hopping until midnight, my mother and I were having an unbelievable time drinking, dancing and getting chatted up by so many guys.
Surprisingly, my mother knocked back every offer from the guys who wanted to buy us drinks.
“Don’t ever put yourself in a situation where you can get spiked, Pippa,” she educated me. “Predators are wolves dressed in sheep’s clothing. No guy or free drink is worth the risk, especially in this environment, where the guy is only looking to get his dick inside you! Pull on your intuition. Suss the guy out before deciding if you want to sleep with him.” I knew my mother was drunk, but she spoke wise words.
We eventually ended up at a lively bar playing trance music. My mother was reliving her youth from the late 90’s. It was hilarious and so much fun. As we danced a couple of handsome guys at the bar were seriously eyeing us up. They looked to be in their thirties. We both noticed and giggled.
“Which one do you want, Pippa?” my mother drunkenly laughed, shoulder barging me gently.
I laughed and blushed. We had joked about this back home, but now it was real, I felt I couldn’t pull with my mother. “They’re too old for me!”
“Don’t be so ridiculous. Too old for you and too young for me to date perhaps, but not to have some good old fashioned vacation fun with.”
“You’re crazy!” I laughed.
“Come on, let’s go call their bluff!” My mother practically dragged me off the dance floor towards our two handsome admirers.
I was blushing bright red, hiding to the side of her as she stood at the bar beside the men. “I’ll have a double gin and tonic, and my daughter will have a double vodka and red bull, when you’re ready, guys!” she told them.
I could have died, and what happened to the advice about free drinks and telling people we were sisters? I thought.
“Daughter!” The guy closest to my mother nearly chocked on his drink. He was about five-ten with short blonde hair and a toned looking body underneath his not too tight shirt.
“We were betting on whether you were sisters or friends!” The other guy laughed. He was slightly taller and stockier with longer dark hair. He was slightly more handsome too.
My mother giggled flirtatiously at the two men and then reminded them of her order. The blonde guy introduced himself as Jonny before buying our drinks. The dark-haired guy said his name was Paul and shook our hands softly.
I felt completely lost. Not knowing what to say, other than giving my name, I accepted the drink and the four of us went and found a table.
Jonny quickly slipped in front of me behind my mother, making sure he got to sit beside her. Paul then kindly offered me to sit first, before siding up to me.
Clearly the guys had already picked us before we could pick them. I didn’t mind because I didn’t believe anything would happen, and I did find Paul the more attractive out of the two. Although they were both good looking guys.
I managed to relax into the conversation and forget about the age differences, until my mother and I learned we were well off the mark with their ages.
Jonny was actually born the same year as my mother; she was only three months older than him. Paul then looked awkwardly at me before confessing he was forty-two.
My mother didn’t seem to mind that her eighteen-year-old daughter was sat beside a man old enough to be her father. She had become so wrapped up in Jonny’s blue eyes and smooth talking, they eventually went off to dance, leaving me alone with Paul.
He could see I was nervous, so instead of hitting on me, he asked about my life back home, and if I had a good time in Crete. He told me he and Jonny were business partners.
What I didn’t realise, however, was that Paul was in fact hitting on me. My mother would later laugh at my naivety when we discussed it very quietly on the flight home.
He had slowly but surely gained my trust without me even realising it. I didn’t once catch him checking out my cleavage, even though he very politely complimented my hair and dress several times.
Maybe I didn’t want to catch him. He made me feel good and relaxed while my mother and his friend danced and flirted outrageously on the dance floor.
Paul asked if I fancied joining them, but I couldn’t bring myself to dance with such an older man. He might have looked ten years younger, but I knew he wasn’t. Most of the guys I’d seen smiling and eyeing me up in the bar did actually look to be around my age.
Then Jonny and my mother returned to the table. We drank some tequila shots before my mother insisted on taking me to the lady’s room.
“How are you getting on with Paul?” she grinned.
“He’s cute.”
“He’s nice. You want to take Jonny back to your room, don’t you?” I laughed.
“Correction. I am taking Jonny back to my room,” she giggled drunkenly.
“I thought we weren’t ditching each other for guys, sister!” I made a point.
My mother suddenly looked surprised. “Are you not interested in Paul?”
“He’s older than you!” I laughed.
“So,” my mother shrugged. “How many times do I have to keep telling you, you’re on vacation.” I sighed and freshened up my face. “Listen to me, Pippa. Do you like the guy or not?”
“Yeah, he’s nice,” I confessed.
“And what if he was twenty years younger?”
“But he’s not.”
“But if he was?” my mother smirked.
“Then it would be different,” I giggled.
My mother laughed. “Stop being so uptight. Dance with the guy. If you don’t change your mind then I’ll ditch Jonny and we’ll go back to the apartment, just me and you.”
I didn’t feel guilty, but I knew she was right, as usual. I did like and fancy Paul. It was only his age, and the fact I was ‘pulling’ with my mom holding me back.
“Ok. I’ll dance with him,” I giggled once more.
Like two besties, my mother and I rejoined the guys at the table. We had one final round of tequila before taking to the dance floor. I was drunk but in control of my decisions.
The music had mellowed to a more progressive type of trance. The place was still buzzing but people weren’t jumping around to the bass anymore. It allowed for Paul to dance closer to me, so I relaxed and moved my hips with my arms bent in the air.
Glancing towards my mother, Paul and I laughed as she ground up against Jonny. He had his arm around her waist and his thigh between her legs. Moving rhythmically to the beat, my mother was in slut-mode, rubbing herself against Jonny’s thigh.
I returned my attention to Paul, whose gaze was burning down from above into my cleavage. It was clear he wanted some of what his friend was getting. I smiled at the hope in his eyes as we continued dancing.
It was then I actually let go of his age. Flicking my eyes back to my mother, I gradually found myself becoming a little jealous.
Jonny wasn’t holding back because my mother was leading him. Paul, however, was holding back because of my hesitancy, but I could see how much he wanted me. Like mother, like daughter, I said to myself.
“What’s on your mind?” I asked Paul with a wry smile.
“Nothing much,” he grinned.
“Your eyes say different,” I continued smiling.
Paul continued grinning. “Can I be honest with you, Pippa?”
“I expect nothing less!” I laughed.
Paul looked me in the eye and then blatantly ran his gaze up and down my body. I blushed at the silent compliment as his eyes paused over my cleavage before returning to look me in the eye again. It was his clearest indication yet.
“You’re the hottest thing I’ve seen in a while, Pippa. I think you’re great. If maybe you can look past the age difference, then maybe we could have a really great time together.”
“Thank you, Paul. I really like you too.”
He smiled as I looked at my mother and Jonny again. They were now snogging each other’s faces off as if they were my age.
Like mother, like daughter, I stepped closer to Paul and turned my back to him. He didn’t hesitate in putting his hands on me for the first time that night. He held my hips, and we began to move from side to side with the music.
I pushed my ass into his groin and laughed. Paul whispered into my ear that I was ‘sexy’ and then he pulled me tight against him. My ass was now grinding against the front of his trousers. I felt warm inside and gooey between my legs.
Paul moved one hand from my hip, sliding it round to my tummy. He then started grinding his crotch into my ass. At that point I knew we were going to end up in my room.
I looked at my mother to find her grinning at me. She winked and then continued her dirty dancing with Jonny. Yes, we were definitely taking these guys back to our rooms.
Having come alive and having something hard and excited poking into my backside, I spun my body and wrapped my arms around Paul’s neck. He put his hands on my hips, and we kissed passionately on the dance floor.
Wow! I was kissing a guy older than my mother, who was getting off with a guy only a few feet away. My arousal went higher still, and I started panting while we kissed.
Suddenly feeling I was in competition with my mom, I broke the kiss and asked Paul what his plans for the night were. He chuckled and slid his hands down over my ass.
“There’s this really hot girl in a black dress,” he spoke seductively into my ear. “I was hoping to help her out of it.”
“Do you think she’ll let you?” I teased. Paul cupped my ass over the dress and squeezed my cheeks.
“If she does then she’s in for a really good time.” Paul squeezed my cheeks again as I clung to his neck, moving to the music. I was so turned on now.
“You sound so confident,” I gasped. “What can this lucky girl expect once you’ve helped her out of her black dress?” Paul kissed me softly before answering.
“She can expect to be treated like a lady for starters,” he assured me. “Then she’ll be kissed and nibbled all over. She doesn’t know how good I am with my fingers and tongue yet. I think she won’t know what’s hit her if she lets me go down on her.”
Coming over all giddy, I kissed Paul again. I wanted to grab the front of his pants and squeeze what I suspected was a good-sized cock. “Do you think she’s good with her hands and mouth?” I murmured. I was becoming too hot to speak properly.
Paul grunted and pulled me in really tight. His fingers went under my dress and squeezed my flesh, lifting me up on to my tippy toes. “I think she’s probably better than she realises, and I think she’s great with her tits too.”
I missed a breath, so I sucked sharply in his ear on the next one. My nipples were hard inside my braless dress and my clit was throbbing.
“Do you like her tits?” I was teasing while my sanity hung by a thread. This game was sending me around the bend. I’d never played at something so erotic before.
“She knows she has great tits. It’s why she’s wearing the black dress. I sure hope I get to fondle them later.”
“Ohhhh,” I gasped.
“Are you two love birds ready to get out of here?” It was my mother, holding a grinning Jonny’s hand. Saved by the bell, I thought. Saved from groping a man’s cock on the dance floor and appearing sluttier than my mother.
We left the bar like two couples, which effectively we were for the evening. The cool air outside immediately hit me, letting me know I was more drunk than I realised. I was still in relative control though. Only my libido was out of control.
I was then starkly reminded I had just pulled on holiday with my mother. Joking and laughing as we trotted off down the strip towards our hotel, I knew I could never tell anyone back home about this. A few thousand people on the internet was ok though.
Laughing my fucking ass off!
I’d had one night stands before, only two, but two nonetheless, and they certainly weren’t anything like this. It was very surreal kissing my mother goodnight before she took a stranger into her room for no strings attached sex, and then I took a stranger into my room for the same.
Made worse by the fact he was twice my age. My damn nervousness was returning to scupper my night. However, as soon as Paul closed my door, he took complete control of the situation… and me.
He was right in his assessment. I’d have no idea what hit me until it did. Kissing me urgently, Paul took hold of the dress straps on my shoulders and kissed across my face and down my neck. His soft lips then travelled across the top of my right shoulder, where I felt the dress straps begin to move down my arms.
Giggling excitedly at the pace he was moving at; I unbuckled Paul’s belt and unzipped his jeans. We hadn’t been inside my room for more than a couple of minutes, yet, he had my dress falling down my body, exposing my full breasts while I pulled out his cock and tugged on it.
Long gone was the indecisive Pippa. Age was just a number now, as Paul scooped my breasts into his hands and sucked on my excited nipples. His cock grew bigger and thicker in my hand before I had to get down on my knees and take him in my mouth.
Paul groaned and fondled my breasts while I cupped and gently squeezed his balls, sucking hungrily on his cock as I looked up into his eyes.
Releasing my inner slut, I started licking his balls before tracing my tongue along the sensitive underside of his throbbing shaft. I then swallowed the head and collected his pre-cum with my swirling, eager tongue, before licking back down to his balls again.
We maintained eye contact as his fingers became entangled in my hair. I knew he wanted to fuck my face, but he remained the gentleman for now.
After a while, I stopped giving him head and lifted my breasts. Paul grinned and groaned as I crushed them around his shaft. He then slid his length through my cleavage. It felt so hot and dirty being on my knees in front of a man twice my age, letting him fuck my young tits.
In fear of shooting his load all over them, Paul eventually helped me to my feet and kissed me passionately once again. He then led me to the bed, where he promised to return the favour, tenfold.
As Paul started kissing and nibbling me all over, as promised, I heard moaning and grunting coming from the room next door. I started laughing with embarrassment and put my hands over my face. Jonny was fucking my mom hard on the other side of the wall.
Her gasps and moans were loud and genuine. Paul chuckled and asked if it was the first time I’d ever heard my mother with another guy. It wasn’t, but it was the first time hearing her while I was at it myself.
Trying to block out the noisy sounds of my mom’s raw passion, I closed my eyes and concentrated on what Paul was doing to me.
He teased his way around my body, taking his time with my breasts, areola and nipples. He kissed and licked his way down my tummy and all over my shaven pubic mound, before burying his head between my spread legs.
Wow! I now had a forty-two-year-old guy eating out my eighteen-year-old pussy. True to his word, Paul was good with his fingers and tongue. Amazing in fact. It didn’t take him long to finger lick me to an awesome climax.
I wondered if my mother and Jonny could hear me moaning loudly that I was about to cum, because the moment I started screaming out in ecstasy, my mother could be heard grunting out her orgasm. It was quite surreal.
Paul then lifted my legs onto his shoulders and rubbed the engorged head of his cock into my pussy.
“Now it’s your mom’s turn to listen to her daughter getting fucked!” he chuckled and drove his thick cock straight into me.
Forcing the air from my lungs, I gasped for breath when he pulled back out. I then groaned loudly and begged for more. Paul looked only to happy to oblige my pleas to get fucked.
He immediately started thrusting in and out of my body, telling me how wet and tight I was. As if I didn’t already know that.
Like mother, like daughter, I was getting fucked hard while my mother sounded to be getting the same treatment in the next room. In some bizarre way, I suddenly became competitive.
“Take me from behind!” I demanded. Paul chuckled and we changed positions.
Deep doggy always has me screaming like a banshee. Not from terror, but a deep, hard fucking.
Facing the wall, separating the two bedrooms, Paul entered me from behind, yanking my head back by my hair, and then fucking me like a vacation slut.
I received the hardest, deepest pounding of my young life, Paul and his cock had me screaming like said banshee. There was no way Jonny and my mom didn’t hear me getting fucked to orgasm.
I started laughing the moment my orgasm subsided. Paul then got me to go on top. As I softly sat on his cock and gently moved my body, the action in the next room sounded a little crazier.
My mom was repeatedly moaning, and her bed was just as noisy. Instead of trying to block out the noise this time, which I hadn’t been able to do anyway, I took my time riding Paul’s cock while I listened.
As he squeezed, played and sucked on my breasts, he became lost in them, while I gradually bounced my way to another climax.
I became lost in the sounds of my mother getting fucked. I reckoned she was getting it from behind, because it sounded so animalistic, and the bed was rocking and squeaking so loud.
I’d heard my mother having sex before, but not like that. Her moaning stimulated me, and my movements became in tune with her gasps of pleasure. I closed my eyes and visualised the scene inside the next room.
Jonny working tirelessly to satisfy my insatiable mother, while she clutched at the bedding with her face all screwed up in agony and ecstasy.
My nipples were being sucked so hard by Paul while his cock was buried deep inside me, I put my hands on his chest and continued visualising the scene next door.
I began to bounce vigorously on Paul’s cock, matching each and every one of my mother’s screams of ‘Ah! Ah! Ah!’
Moaning in unison with my mom, like mother, like daughter, we soon came together. I heard Jonny start grunting and then Paul wrapped his arms around me before he started grunting, and just like that, both rooms became silent, except for Paul and I panting for breath.
Slowly removing myself to fall beside him, I lied on my back recovering from some great sex. I felt his cum leaking out of my satisfied pussy as I drifted off to sleep.
I don’t know how long I was out for, but when I woke, I was all alone. I then quickly realised my mother was at it again. Her screams and groans were much louder than before.
Where’s Paul? I wondered, before it became obvious. Slipping my naked body out of bed, I went into my mom’s room.
There was my one-night stand, on his knees behind my mother, giving her one hell of a pounding from behind, while Jonny knelt in front of her with his cock buried down her throat. I wasn’t shocked, surprised or angry. I wasn’t even jealous.
Jonny looked at me and smiled. He then moved away from my mother and got off the bed. I stood naked in the doorway, watching Paul fucking my mom just as hard as he had fucked me. She looked and sounded so slutty, moaning with her big tits swinging as she got fucked. It was filthy. I was aroused once more.
“Let’s go to your room, Pippa,” Jonny grinned. I watched his fit, naked body walk towards me, or rather, I watched his hard cock coming towards me.
Giggling at the madness I’d just walked into; I was quickly escorted back to my room by my mother’s one-night stand. I couldn’t protest, something inside me just went with it and allowed him to take me away.
“I actually wanted you when I first saw you dancing with your mom in the bar, but Paul insisted,” Jonny told me. I was neither impressed nor insulted by his confession. “You’re both smoking hot, but you’re the one I really wanted to dance with.”
“You mean fuck!” I laughed.
“Paul said you’re tight. I knew you would be,” he grinned and laid me on my bed. “Have you and your mom ever done this before?” he smirked, positioning himself between my spread legs. “I love your tits.”
“No, have you and Paul?” I threw back at him, as he grabbed and squeezed a breast.
I was already wet with Paul’s sperm still inside me. Jonny groaned as he started pushing his cock into me. “We’ve done this a few times, but never mother and daughter.” With that, Jonny pushed into me, enjoying how tight I was compared to my mom, in his words.
It felt nice. He felt nice. Forgetting where his cock had been the last couple of hours, I wrapped my arms and legs around his body and clung to him while he fucked me with hard, deep thrusts.
It didn’t take me long to cum on his cock, especially while I listened to round two of my mother getting fucked again. As soon as I climaxed, Jonny flipped me over and took me from behind. He drove into me, and mom and I started groaning through the walls again.
I don’t know when she came and eventually stopped, because Jonny fucked me so hard, much harder than Paul, that I buried my head in a pillow and screamed my head off. Soon enough, I had my second guy of the night shooting his cum deep inside me.
Paul and Jonny left together while my mom and I remained in our beds. After they left laughing and celebrating, she came into my room to see me.
She offered me a cigarette and we sat up in my bed smoking. I didn’t care that we were naked, and we had just shared the same guys, I’d deal with that in the morning.
This happened many years ago, and even now we still laugh about it when we pull out the photo album, of course we didn’t take any photos of the action, you perverts! X
