Join the best erotica focused adult social network now
Login

From Virgin To Fuckboy

"This is the true and actual account of how I lost my virginity to a much older woman, my girlfriend's mom."

239
36 Comments 36
10.8k Views 10.8k
5.4k words 5.4k words

Author's Notes

"OK, so I wrote this a very long time ago, maybe one of the first stories I ever wrote. And I wrote it so I wouldn’t forget the woman or the moment my life was shaped into the person I am today. It’s a true story and exactly how it happened. <p> [ADVERT] </p>And that’s why I have been reluctant to ever share it but, since I have been doing some formatting and editing for Foxysue ‘s true life experiences it has urged me to share one of my most exciting experiences as well. Thanks for reading."

It was the 3rd of December 1980, and the summer was shaping up to be a hot one in South Australia. It was my last fortnight of trade school for the year when I met Lisa. She was the most beautiful girl I have ever seen at the tender age of seventeen. I would find out later she came in a close second to her mother, Heather.

It was Monday morning, and I had slept in, so I was already late for the Gawler train. I only just had time to jump in the last carriage as it was about to pull out of the station. I usually sat in the front carriage to get off the train first, so I didn’t miss my connecting bus to trade school.

The last carriage was always full of school kids. I say that, but they were the same age as me, having only turned seventeen a week earlier. I left school in year eleven after getting an apprenticeship. But I was working now, so I was clearly cooler than they were. Well, in my mind, anyway.

So I sat there trying to ignore their shenanigans. I reached back, slid the window behind me open, pulled out my Marlboro Reds, and lit one up. Acting cool, I blew the smoke out the window. Just to point out, these were the days of the old trains with no aircon and the doors didn’t shut and the windows opened. How nobody fell out is beyond me.

It was then I first laid eyes on her. Looking across the carriage sitting opposite me was a living angel. Her beautiful long curly red hair hung down under her wide-brimmed straw hat. The blue band told me she went to Emmanuel Girls' College. She had alabaster skin with a light dusting of freckles across the bridge of her nose and cheeks. But it was her piercing green eyes that set my heart on fire.

She was wearing a tartan box pleat school skirt. It was clearly rolled up at the waist, making it much shorter than allowed at an all-girls school. I could just make out the visible pattern of the lace bra under her white cotton blouse. She had white socks pulled up to her knees and a pair of black school shoes. One foot pointed at me, swinging up and down from her crossed legs. I won’t lie; I was lost in those damn eyes.

“Hey, idiot!" She said, startling me out of my trance.

“You're not allowed to smoke on the train."

I looked her up and down, then said, “Oh yeah, and who’s going to stop me?”

At which point, she got up and walked right up to me. Sitting down next to me, she pulled the cigarette out of my fingers and threw it out the open window.

“Hey, what the hell?” I snapped at her.

“Don’t you know smoking sucks? It’s bad for you. And besides, I don’t like boys that smoke,” she said, smiling at me.

“Oh yeah, well, I don’t remember you being my girlfriend, so I don’t really care what you think,” I said, taking the packet of smokes out of my top pocket to light another one up.

Before I knew what had even happened, she snatched the packet of cigarettes out of my hand and launched it out the window as well. Now I was pissed off.

“What the fuck, why the fuck did you do that?” I snarled at her.

“I told you before you can’t be my boyfriend if you smoke, so you will have to give up,” she said, her gorgeous green eyes scorching into my very soul.

“And I told you before you aren’t my girlfriend. How do you know I don’t already have one?” I retorted angrily that she had thrown my smokes out of the train.

“Do you?”

“Do I what?”

“Do you have a girlfriend?”

“No, not right now,” I replied.

“Good, then it’s settled. You are my boyfriend, and I will be your girlfriend. I’m Lisa, by the way,” she said as she held my hand in her lap.

“You're batshit crazy! You can’t just say I’m your boyfriend and expect me to go along with it.”

She looked at me briefly, then leaned over and kissed me. At first, I was reluctant, and then her tongue pushed against my lips forcing them apart, and I kissed her back. I don’t remember much of the rest of the trip, as my lips were glued to hers most of the way.

When the train pulled into the station at Adelaide Central, she reached into her school bag and pulled out a pen. Taking my hand, she wrote Lisa and then her home phone number on the back of my hand.

She jumped up with the rest of the school kids and started to get off the train.

“Hey, boyfriend, what’s your name anyway?”

“Kevin, my name is Kevin.”

“Well, Kevin, call me tonight after 6:00 pm.” She blew me a kiss and was gone in the crowd of people out the door.

I sat on the train momentarily, stunned by what had just happened. I missed my connecting bus, making me late for school, and the rest of the day went by in a blur. I just couldn’t get this crazy beautiful girl out of my head.

I called her that night, and we talked for a couple of hours about nothing and everything, and for the rest of the fortnight, we met at the train station every morning and kissed each other all the way to Adelaide station. I never smoked another cigarette since Lisa threw my smokes out of that train.

Lisa’s school broke up for the Christmas holidays, as did trade school. Over the two weeks I had known her, I learnt Lisa’s parents had a bit of cash. Her father was in real estate; her mother worked part-time in the real estate office. But most importantly, they had an in-ground swimming pool, and I didn’t know anyone who had one. So we had arranged for me to come over the following weekend for a swim.

Now Lisa’s parents were meant to be working. Apparently, they had a few open homes and an auction on. Saturday came, and I rode my motorbike the thirty-six kilometers to Gawler from my hometown. It was a hot day, around thirty-nine degrees Celsius. I knocked on the front door, and no one answered. Then I remembered Lisa had told me to come through the side gate if she didn’t answer the door.

I opened the side gate and walked past the garage stopping dead in my tracks when I saw the most beautiful woman I had ever seen. A strawberry blonde woman in her early forties was resting with her arms folded on the side of the pool.

“Well, hello, you must be Kevin. The boy that has been keeping our phone tied up for the last two weeks!” She said, looking over the top of a pair of sunglasses.

“Umm, hi. Yeah, that’s right. Sorry to disturb you, but no one answered the door, and Lisa said to use the side gate,” I said, looking around for her.

“Lisa did try to call you earlier, but your mom said you had already left. Lisa was called into work at Coles. She doesn’t normally work Saturday, but several girls called in sick, so she had to go to work at the last minute,” she said, her legs floating out behind her.

“Oh, alright, well, I will head off then. Sorry to disturb you, Mrs. Manning. Can you let Lisa know I dropped by?” I said, about to return to the gate.

“What’s the rush, Kevin? You are here now, and it’s a stinker of a day. You might as well have a swim to cool down before you head home.”

Oh crap, I thought. I hadn’t bought my bathers. I was planning on using it as a line to get Lisa to go skinny dipping with me, well, hopefully.

“I’m sorry, Mrs. Manning, I forgot to bring my bathers. Maybe next time.”

“Wait, am I to understand you came all this way to spend the day by the pool with my daughter, and you didn’t bring any bathers?” She said, raising her eyebrows.

“Umm, yeah, I realised I didn’t have them when I got here, Mrs. Manning,” I said, realising Lisa’s mom might be onto my intentions.

“Firstly, you can drop the Mrs. Manning crap. Call me Heather. And secondly, I don’t think you forgot your bathers. I don’t think you had any intention of needing them. That little stunt might have worked on my naive daughter, but it doesn’t work on me!” She said.

“Honest, Mrs. Manning,” I started to say before she cut me off.

“Heather, remember. And you can stop right there, young man. As far as I know, Lisa is still a virgin. Well, according to her diary, she is anyway. But she wasn’t planning on staying that way for much longer. Now as you can understand, that puts me in a very difficult position. You both clearly had some intentions of screwing like a pair of rabbits today. Am I correct, Kevin?”

Oh fuck! I thought for sure I was in deep shit. I had no idea how to answer that, so I responded with the most polite answer possible.

“Mrs… sorry, Heather, I really like Lisa. I had no intentions of doing anything other than maybe trying to convince her to go skinny dipping with me. I promise I hadn’t even thought about sex with Lisa until now. I swear,” I stammered, trying to convince what I thought was an angry mom.

Heather looked at me, not speaking for what seemed like forever. I even thought about making an escape and just sprinting for the gate.

“I see. So you like skinny dipping, do you? I suppose you and your friends do it all the time. You all get naked and go swimming somewhere?” She said sarcastically.

I looked at Heather; she hadn’t moved. She was still leaning on the side of the pool with her arms folded, her chin now resting on them.

“No! I have never been skinny dipping. If Lisa had agreed, this would have been the first time,” I replied, feeling a little deflated all my plans had gone to hell.

“Never been skinny dipping, huh? Are you still a virgin as well?” Heather asked, taking me by surprise.

I didn’t know what to say. Jesus, my girlfriend's mom was asking me questions I really didn’t want to answer.

“Yes,” was all I could muster, embarrassed while I looked down at my feet. Plus, it was as hot as hell standing in the sun in jeans and a jacket on. I just wanted to leave.

“Well, we can do something about one of those things today, and we can work on the other one. Let’s see how things go,” Heather said, standing up, naked from the waist up. At the time, it was all I could see. I couldn’t believe she was flashing me the most amazing tits I had ever seen. 

The truth was they were the only woman’s tits I had seen, besides my mother's, accidentally. They were so different than my previous girlfriends. They were large and round. The nipples were so long and thick.

“Well, don’t just stand there with your mouth open like you have never seen a naked woman. Strip, get those clothes off. You wanted to go skinny dipping. Well, now is your big chance,” Heather said, looking at me intensely.

“Umm, I don’t think that’s a good idea. I think I should just leave,” I stammered in shock, staring at my girlfriend's mom's tits and getting a boner.

“It wasn’t a question, Kevin. Get your clothes off and get in the pool now!” Heather said sternly.

I looked around to make sure Heather's husband wasn’t around, waiting to beat me stupid or something. I removed my jacket before pulling my tee shirt over my head. Still unsure, I hesitated. Heather just gave me a look, and I knew she was serious. Undoing my jeans, I slid them down my legs.

I sat down on the lawn and undid my shoes, pulling them off, then my socks, followed by my jeans. Standing back up, I put my hand over my crutch in an attempt to hide my raging hard-on as it tried to push past the waistband of my jocks.

“Lose the jocks, mister. It’s only fair. I mean, it was these that made the lovely-looking cock nice and hard, wasn’t it,” Heather said, squeezing her perfect tits together.

There was no turning back now. I was about to get naked in front of my girlfriend's mom. This is insane. I thought as I hooked my thumbs into the waistband of my jocks and quickly ripped them down my legs. Stepping out of them, I quickly jumped in the pool's cool water, hoping it would help my cock go down.

“See, that wasn’t so bad, was it?” Heather said when I surfaced, wiping the hair out of my eyes.

“It’s weird. You're my girlfriend's mom. I shouldn’t be seeing you naked, and I certainly shouldn’t be naked in front of you,” I said as Heather approached me.

Heather stood so close her nipples were almost poking me in the chest. I almost died as she reached out and grabbed my hard cock.

“Your mind might be telling you that it’s wrong, but a hard cock never lies, and yours is telling me you liked what you see,” she said, sliding her hand up and down my stiff shaft.

I almost pinched myself to see if I was dreaming. Lisa is really beautiful, but her mom was next-level stunning, and I could see where Lisa got her looks from. The only difference is Heather has blue eyes. Looking around again to ensure this wasn't entrapment, I reached out and put my hand on her large firm breast.

“Lisa’s diary says you are the best kisser she has ever had.”

I didn’t even get a chance to answer before she leant in, pushing her lips against mine, her tongue sliding into my mouth, her arms wrapping around my neck as she kissed me like I had never been kissed before. When I was sixteen, my best friend's nineteen-year-old sister had spent hours teaching me how to kiss, so I was pretty good at it, or so I had been told.

My arms went around Heather's waist and pulled her in close, her large hard nipples pressed into me, my hard cock pressed against her stomach. I can’t tell you how long we kissed, but Heather looked at me when she pulled away and said, “Wow.”

She kissed me again, took my hand, and led me up the stairs and out of the pool.

“Lisa was right. You are a good kisser. Time to see what else you are good at, though,” she said as she threw me a towel.

We dried off, and she again took my hand and led me into the house. As we walked through the house, my head was spinning. I didn’t know what would happen, but I was damn sure I had given up worrying about it.

We entered the master bedroom, and Heather led me to the bed. Turning me around, she pushed me back on the bed before kneeling between my legs. Looking directly into my eyes, she grabbed my cock and slowly stroked it.

SofiaNashh
Online Now!
Lush Cams
SofiaNashh

“Have you ever had this gorgeous cock sucked before, honey?” She said, licking her lips.

I just stared back at her and just shook my head.

“Good, I want to be your first at everything, If my daughter wants to lose her virginity to you. I’m going to make damn sure you know what you're doing, and she isn’t disappointed her first time like I was!”

Holly fuck, I thought, is this really happening? Not only is she going to let me fuck Lisa, but she is also going to show me how to do it. My heart was racing, and my cock twitched as her fist slid up and down it.

Looking into my eyes the whole time, Heather leant forward and ran her tongue along the underside of my seven-and-a-half-inch shaft. She did this several times before wrapping her lips around the head and flicking her tongue repeatedly across the top of my knob. Slowly she slid her mouth down my shaft until her nose was nestled against my pubic hair.

While she swallowed my cock down her throat, she somehow tickled my balls with her tongue. I thought I would faint; it felt that good. She began bobbing her head up and down on my dick, making obscene gagging noises. It was all I could do to stop shooting my load into her mouth, and then my balls exploded without warning.

I’m sure the first jet went straight to her stomach. The second was somewhere in her throat, the third in her mouth, and the fourth, fifth, and sixth splashed across her face and perfect tits.

Heather’s face was covered in cum. It was splattered from her hair to her tits and everywhere in between. Long strings of thick white goo hung from her nose and chin. Heather got up and disappeared from the room, returning with a wet washcloth. She was wiping my cum from her face, neck, and tits when she returned. My cock was still rock hard and pointing toward the ceiling.

“For future reference, it is very impolite to cum without warning your partner. Having said that, I had forgotten just how good a teenage boy's cum tastes. It’s been a lot of years since I have had the pleasure to suck such a beautiful young cock,” she said, sitting on the bed next to me.

“Oh, I’m really sorry. It just happened. It even surprised me,” I said, apologising.

“No harm done. I would have liked to have the entire load, that’s all, but the first jet almost choked me, and I had to pull your cock out of my mouth. I’m a big fan of eating cum, not wearing it. But chalk that up as your first facial,” Heather said, smiling at me after cleaning my cum from her face and breasts.

“I promise I will try not to cum so soon next time.”

Heather cocked her head and looked directly into my eyes. 

“You seem pretty sure there is going to be a next time. Would you like to cum again for me?” She asked, wrapping her hand around my cock.

“I would like that very much,” I said, maybe a little too eager.

“Hmm, so would I. It has been a long time since a man has cum that much on me or in me, and I liked it very much. But now it’s my turn,” Heather said, sliding back up the bed, grabbing a pillow, and sliding it under her bum.

“So Kevin, tell me what experience you have had with girls. Because this is where the learning begins, and I want an idea of just how many bad habits I need to fix.”

Honestly, I didn’t know what she was talking about at the time. Learning, what learning? I thought she was just going to put my dick in her, and we would fuck. Boy, was I ever wrong! I must have had a strange look on my face because she asked me again.

“Have you gone down on a girl? Fingered a girl? First base?”

“I have fingered lots of girls,” I said proudly.

“OK, show me. What you have done to so many lucky young ladies,” she remarked, the hint of sarcasm not lost on me.

Until now, I hadn’t really looked at Heather's pussy. I was so gobsmacked by her tits and the head job I just hadn’t looked properly. But now there it was, pushed upwards from the pillow under her bum. Heather had her legs spread wide, and I saw my first real vagina.

It’s true I had fingered a dozen or so girlfriends, but not like this, not openly on display as Heather's was. I had put my hand in their panties or up under their dress. Only once had I been fully naked with a girl, but she was shy. So she had the covers over her and got undressed under them, then I slid in and did the same.

That was the closest I had come to losing my virginity. But as I rubbed my cock against her pussy I had blown my load, and by the time we tried again, we heard her parents' car pull in the drive. We never got another chance before we broke up.

So here I was, just turned seventeen, lying between my gorgeous girlfriend's mom's legs staring into the most beautiful sight I had ever seen. It was Heather's pussy that gave me the appreciation for long, thick labia and big clits that I still have today.

Heather’s pussy was capped off with a big triangle of soft red pubic hair, but she shaved the rest around her pussy lips and bum. I was intrigued by how smooth and soft the skin was around her pussy, as I ran my fingers up either side of those long fat lips.

Heather propped herself up on her elbows and looked down at me, smiling.

“This is the first one you have ever seen, isn’t it?” She asked, smiling like a Cheshire Cat.

“Sort of, yeah. I have seen plenty of bush, but I have never seen one close up like this without hair everywhere,” I said.

“Do you like it, or does it look gross?” Heather asked, I’m sure fishing if I liked how it looked, and I did very much.

“I love it. I have seen lots in magazines and stuff, but yours is so beautiful.” And I was genuine; I loved Heather's pussy. She set the benchmark for every woman I have been with since.

Heather sort of went into teacher mode. Holding her lips apart, she started explaining to me each part of her pussy and which parts to touch, and how to touch them. It was then that I fell in love with long thick clitorises.

Heather pulled her clit hood back, exposing her almost inch-long clit to me before asking me to lick it. I looked at her, not sure if she was serious or not. Did she really want me to lick her pussy?

“Don’t you dare be one of those men who doesn’t pleasure your partner before you just stick it in and wham, bam, thank you, ma’am, roll off after emptying your nut sack. Look, just suck on it as I sucked on your dick. Just put your lips around it and suck it. Run your tongue around it,” she said, holding her erect clit out for me to suck.

I lay on my stomach, my face inches from her open, very wet pussy. I couldn’t believe how it smelt. It had a robust feminine smell, hard to explain. Still, it was different from smelling my fingers after being with one of my past girlfriends.

"Go on. I promise it won't bite. Gently run your tongue up either side of my labia. Then run it between my pussy lips, drive it in as deep as you can, then run it back up the outside. The aim is to tease me with your tongue until I can't stand it anymore, and I have to beg you to fuck me."

Her labia, as she called them, were long and thick, and I wasn't sure about it. I had never seen a pussy like this before in any magazine. Then again, I had never seen a pussy without hair on it. I did as Heather instructed and gently ran my tongue along the outside of her long lips. I can't explain the taste. It wasn't horrible. There just wasn't anything to compare it to.

I used my fingers to pull her lips apart. I couldn't believe how wet and sticky Heather's pussy was. I opened her lips wide, forming a little love heart with a little penis at the top. Her pussy was bright pink inside, and I had a sudden urge to taste it.

I did as Heather instructed, running my tongue from the bottom to the top, my tongue flicking across what she had called her clit, which looked like a tiny dick that caused Heather's body to shudder and goosebumps suddenly appear over her entire body.

"Hmmm, that's perfect, Kevin. You are doing a fabulous job. Now repeat all of that but don't forget to push your tongue in and out of my pussy a few times and then suck my clit."

I pushed my tongue deep into her velvety folds of flesh. The more juicy fluids that ran out of her pussy and I tasted, the more I wanted to drink them down. Heather had me hooked. I could have lain between her soft mature thighs forever and drunk from this incredible fountain.

Running my tongue up through her lips again, it lapped over that little dick, and I felt Heather tremble. Oh, she liked that, so I licked it some more, flicking it with my tongue. Heather grabbed my hair and held my mouth down on it.

"Oh God, yes, that's it. Suck my clit, you beautiful boy. Make me cum."

So I did as instructed. I puckered my lips and sucked on it, my tongue flicking rapidly on the end. Heather's thighs clamped tight around my head, her arse lifted off the bed, and suddenly there was a lot more sticky clear fluid than there had been before. Plus, Heather was moaning and swearing.

Eventually, her thighs released me, her body went limp, and she breathed heavily. I had no idea what an orgasm for a woman was. I knew I shot jizz out of my dick like a cannon, but I didn't know what happened to a woman until that moment. And I felt proud that I was able to give Heather one.

"Kevin, that was something else. Are you sure you haven't done that before? You are very good at it. You made me cum much quicker than my husband."

That was the first mention of her husband, but I didn't mind because she just told me I was better at whatever we did than he was. 

"Wow, thanks, Heather. I really enjoyed that. Honestly, I wasn't sure at first, but I loved it and could do that all day."

"Well, you can do that to me anytime time you want. I had an amazing orgasm. Now how about we fix that other thing."

"What other thing? I don't think this day could get any better."

"Oh, trust me, it is about to get a whole lot better."

Heather sat up and pushed me onto my back then she straddled me. I could feel her pussy making my hard cock and balls wet as she sat down on me.

Heather leaned down and kissed me again. It was like nothing I had ever experienced, and I melted into her body. Her beautiful breasts pressed hard against my chest, and her pussy leaking juices all over my crutch. She was right. Maybe it could get better.

"OK, Kevin, I will ask you this because it's the right thing to do. Would you like to fuck me? Do you want to give me your virginity?"

"Fuck yes. Is that an option right now?"

"That's all I need to know."

Heather lifted up, took my cock in her hand, and lowered herself down on me. I can't describe how that first moment my cock disappeared inside Heather felt, but the instant warmth and softness was overwhelming. You can only lose your virginity once, and I thank my lucky stars every day that I lost mine to Heather.

But of course, just like Heather had predicted, it just got better and better until her head was thrown back, her hands were behind her on my thighs with her back arched, and she bounced up and down on my cock as if her very life depended on it.

I reached up, and I grabbed her large tits as they bounced up and down and pulled on those long thick nipples. It felt like forever, but it was only a few minutes, and I felt my balls doing what they did when I jerked off.

"Heather, I'm going to cum again."

"Fuck yes, cum for me, baby, cum inside me. Let me feel you cum."

Heather started screaming as I squeezed her tits really hard, and my cock jerked as jet after jet shot out from my cock deep inside her. Again Heather's body began shuddering, and she started screaming and swearing before she collapsed on me in a sweaty heap.

We lay there for a while, and my cock got a little soft but was still hard. 

"I forgot what a young cock like yours is capable of. You are still hard. Did you enjoy that?"

"Did you have to ask? Shit, that was the best thing to ever happen to me. I loved it."

"Mmm, me too, very much. Your cock is quite a bit bigger than my husband's, and you hit me in places he never has. And it feels like you aren't done yet," she said, sliding off my cock and sliding down the bed.

I couldn't believe it when Heather put her mouth over my cock and started sucking me off again. It had just been inside her, and she was hungrily sucking and licking my cock shaft and balls.

Looking up at me with those beautiful eyes, she said, "I want you to take me from behind. I want you to fuck me as hard and as fast as you can. Don't be gentle this time. I want you to fuck me like you hate me."

Heather crawled back up the bed on her hands and knees and stayed that way next to me.

"Get behind me, Kevin, and fuck me like the bitch I am."

When I got behind Heather, she was leaning forward and had her legs closed, and all her pussy bulged out from between her legs. My cock leaped when I saw it. I fell in love with long thick hanging lips and big clits at that very moment.

I fucked Heather five times that day, and it was an affair that lasted another nine months, and yes, I fucked Lisa. The week after Christmas, we dated for a few months, and then she found out I was fucking another girl from my hometown and dumped me. But to my knowledge, she never found out I was fucking her mom, Heather, for another six months after that. It only ended when her husband found out he was being cucked.

When you are seventeen, you don't think much about the important things in life. You are too busy living. It was only years after Heather that I realized the actual effect she had on me and how she shaped me sexually for the rest of my life.  

Like right before I fucked her from behind and seeing her bulging pussy with all my cum leaking out of it. I couldn't resist licking it clean; well, more like devouring it and giving her another orgasm, something I still love doing today with my sexual partners.

I will happily spend hours eating pussy before thinking about fucking my lover. It's no secret if you have read my profile that I love the hotwife lifestyle and love eating my wife's freshly fucked pussy. Everything I love doing today I did my very first time with Heather. And I think an experienced mature woman is the best gift a naive seventeen-year-old boy could get. Long live the MILF.

Published 
Written by Kevtheledge63
Loved the story?
Show your appreciation by tipping the author!

Get Free access to these great features

  • Create your own custom Profile
  • Share your erotic stories with the community
  • Curate your own reading list and follow authors
  • Enter exclusive competitions
  • Chat with like minded people
  • Tip your favourite authors

Comments