Simons Mom

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first times

Simons mom

So, just to set the scene here: my name is Andy, and I was 18 years old when this happened to me. I’d always been a pretty geeky kid growing up. Into science, fantasy, dungeons and dragons, sci-fi and comic book conventions etc. All that jaz.
So as you can imagine, me and my chosen group of friends didn’t really have much experience with the girls, or was ever paid any attention to by them either for that matter. So when the chance to go on holiday with my friend (Simon) and his family out to the lakes came up, I jumped at the chance. Why? Well, not only would I have a blast with my best friend out there, but also his mom was incredibly, ridiculously hot! All of our friends thought so, and we often teased him on it (all in good humour of course) which he took in his stride.
So the thought of maybe getting to see her in a swim suit made my dick twitch and swell a little in my pants. I mean she was stunningly beautiful. In her early 40’s insanely pretty, long blond hair down to the middle of her back, with a figure that celebrities pay thousands to try and achieve. Her breasts looked to be an E cup, all natural and they were still firm and in the right place, and she had an ass to die for.
Me and Simon had both just had our 18th birthdays so our folks were fine with us letting our hair down, staying in our own seperate cabin by ourselves, and even drinking. We’d always been the sensible types so our leeway was pretty liberal.
We arrived there all excited and looking forward to the week long break ahead of us. We settled in right away. We had a great cabin, overlooking the lakes and swimming pools (it was a fairly busy resort type place) and we started having a great time from the off. The first night there we all had dinner together, and then drinks. We played some card games together and just generally had a nice relaxing evening after a long drive.
But the second day there, that was when I got my wish granted.
We all headed down to the lake front where there are bars and sun loungers. We planned a day of sun and swimming. I’d gotten excited already at the prospect of maybe getting to see Simons mom in her beach wear, but I could never have imagined the treat that was actually in store for me.
We found a nice spot of beach area close to one of the bars, it was fairly busy but we found 4 sun loungers all together, with a table in between them. So we settled ourself down into this spot. Me and Simon got the loungers under the parasol for shade (we were pale geeky dudes) and Simons mom and her husband took the loungers in the sun across the table from us.
She was wearing a long maxi sun dress that hugged her perfect figure right down to her ankles. Her feet were so pretty, and perfectly formed in her sandals, and her long blond hair was tied back in a pony tail. She looked amazing!
As we started to get comfy and settle into our loungers, I was secretly watching her as she stood, shielding the sun from her eyes with one hand whilst looking out towards the vast lake at the water skiers and jet skis bombing around. She was smiling, and she looked so beautiful. Her partner Mike (who wasn’t Simons dad, but they got on pretty well) decided to go over to the bar to order us all a drink, which just left us 3. Simon was laid back on his lounger with the latest Star Wars book, and I was laid perched up on my elbows looking out at the lake (but really eyeing Simons mom up)
Then it happened. My fantasy, my dream finally came true!
She dumped her bag next to her lounger, laid her towel over it, and then reached down to the bottom of her dress and grabbed the hem. My heart literally started thumping against my rib cage, I was so excited. I thought Simon must be able to hear it it was so loud. She began to lift the stretchy material of her maxi sun dress up her legs, revealing inch by inch more and more of the skin on her perfectly shaped legs. Up past her knees she pulled it, and she wasn’t stopping there. She carried on pulling the dress up over her thighs. My cock started to swell immediately as it filled with a sudden rush of blood. I had to sit up, or the bulge would be more than visible. My sudden movement caused her to glance my way and she smiled as she pulled her dress up over her buttocks and waist and turned toward her lounger. If she hadn’t been wearing sun glasses I could’ve sworn that she’d winked at me as she did that. Her ass was smooth as silk, and the small bikini bottoms she had on had half disappeared into her ass crack, giving me a full image of her pert full cheeks.
As she had her back to me she continued lifting the dress up over her breasts and off entirely. She was wearing a very flattering green bikini underneath. Each cup of material was just enough to cover the large breast it contained within. The cups were connected at the front by a thin string with beads on it. My cock was rock hard, and I mean full mast. I had to lean over and pretend to be looking for something in my bag for it to not be visible.
She turned around to face me still smiling, and sat down on her bed. “Are you two going for a swim?” she said to me as she lifted one of her legs across the other and began undoing the fastener on her sandal.
“Oh, erm, probably in a bit yea” I replied awkwardly. I still had to remain in a leant forward position in order to not offend her with my swollen member. She kept smiling at me as she slid her sandal off her shapely, smooth foot, and then did the same with the other.
Now I’d never really been into feet before, but this felt like she was teasing me with her body, and I’d never wanted to suck someones toes as much as I did right then. She pulled off her other sandal and swivelled round on her lounger to lay back on it. Her legs were crossed at the ankles giving me a good view of the soles of her soft pink feet, and she was propping herself up on her elbows, making her breasts spread out slightly and bulge out of her bikini at the sides. It was an amazing sight, the sun baking her golden skin. She was still smiling at me as I was leaned over trying to hide my erection. It was a mischievous smile I thought.
“Simon” she said “Mike’s going to need a hand carrying 4 drinks, go and help him” Simon looked up from his book with a confused look on his face and said
“He’ll just use a tray, he’ll be fine”
“Go and help him, and ask him to order us some snack food while you’re there. Chips and things. I’m peckish” Simon huffed, but started to get up “you coming?” He said to me as he got up. “Nah, I’ll stay here” I replied, as I didn’t fancy waving my stonking great hard on around.
He looked a bit miffed, but he shuffled off towards the bar anyway. That left just me and his mom. She got up into a sitting position and turned back round to face me “you won’t be offended if I sunbath topless will you Andy?” She said matter of factly as she was already reaching around her back to undo her bikini top.
Now I’d already clocked a few topless sunbathers scattered around on the loungers near us, but I never dreamed that this would happen.
“No, I’m fine with that” I said rather sheepishly. She was smiling her beautiful smile at me as she fumbled with the knot on her back. Then she frowned “can you undo this knot for me please” she asked as she got up and turned her back on me. I got up, and immediately slouched over again as my erection caught on my swim shorts.
Luckily her back was turned, but I could see her smiling as her head was slightly to the side while she waited for me to help her. I think she knew, and was enjoying my predicament. I was trying not to let other people around us see as I fumbled with the knot on her back. Finally, I picked it free and undid the strings.
I quickly sat back down in anticipation as I knew what was about to happen, and my dick was surely going to explode. “Thanks!” She smiled, as she turned back around to face me and sat back down.
I know she was doing this on purpose to tease me, and enjoying every second of it too. But not as much as I was in my youthful excitement. She pulled the strings back from behind her and lifted her bikini top up and over her head. Her large breasts actually bounced as each one popped out from the cups that were holding them. I think she intended to make them bounce. The way in which she pulled the top off (keeping it close to her chest as she lifted it up) meant that they had no choice. They were so big. I felt like I watched the whole thing in slow motion as her breasts jiggled around after being freed from their constraints, and she turned around in her chair to lay back properly in the sun.
In case you hadn’t guessed already, in my naive and inexperienced predicament, I actually came. It was just too much for me. I had never ejaculated without masturbating before, and I didn’t even know it was possible. But here I was, bent practically double, my leg and abdomen covered in my own jiz.
This remarkable woman had made me orgasm without even touching me. I stared at her in wonderment, laying there in the glaring sun. Her beautifully browning skin was glistening in the bright light, and her large breasts were spread out over her chest, the skin on them ever so slightly paler. Her nipples were a dark pink and standing firm and erect, whilst her areolae were crinkled and tight supporting them. She was clearly aroused by the thought of me seeing her semi naked.
As I ejaculated I must’ve made a grunting noise, as she turned her head towards me and said “you ok Andy?”
“Mm hmm” I nodded. She smiled again, that mischievous smile and turned her head back towards the sun.
This was the point where Simon and his step dad returned.
“Oh my god mom!” Simon yelled at her
“Shut up Simon” his mom returned lazily as she didn’t even move, laying there in the sun with her hands behind her head.
“Put your tits away!” He screamed
“We’re all adults here Simon, grow up” she countered, still not flinching. Mike just chuckled as he placed the drinks down on the table clearly not fazed by any of it, and lay back in his own lounger. But Simon looked mortified.
“Let’s go for a swim” he blasted at me, clearly wanting to get me away from his semi naked mother.
Luckily, since I’d completely emptied my nut sack into my shorts and down my leg, my cock was starting to go back down to at least a semi. So I could stand up again (albeit with a slight bulge)
“Sure” I said, not wanting him to be upset, and we took our drinks down to the water front.
He was clearly upset by his mom, but I thought he was being childish. Yea sure, I would’ve given my right nut to witness what I just had, but still I thought he was being unreasonable. She can do what she likes, she’s a grown woman. We argued for a little about it, but decided to leave it as we clearly had a difference of opinions. We went jet skiing instead.
By the time we returned later in the day, Simons mom and Mike were sat up having a drink together. She was wearing her dress again. They were a little tipsy as they’d had a few throughout the day, and it was edging into the evening. Simon was still pissed at his mom, which he clearly showed by his attitude towards her. They just laughed at him, and told him to stop being a baby (I kinda agreed with them)
Later that evening, Simon and I were back at our cabin laid on our beds just chilling and talking. We’d had a fair few drinks by then as well and we were having a nice night. But then the subject got turned back to his mom sunbathing topless in front of me. He was so mad at her, and was calling her a fucking whore and other derogatory names. I ended up losing my temper with him.
“Look dude, nobody gives a shit except you! Why don’t you just let it go already?!”
“Yea, I bet you’re sooo happy you got to see her tits arnt you?!” He bellowed at me
“For fuck sake, grow up they’re just tits!” I replied, but yes he had a point. I was very happy to have seen them.
“Going to have a good wank over that tonight I bet! Why don’t you take some pictures next time?!”
That was a great idea, I thought. Why hadn’t I thought of that earlier.
“Dude, you’re being pathetic” I told him. But he was obviously a little too drunk to be reasoned with, so I said “I’m going for a walk”
“Whatever” he muttered, as he turned over in bed.
I stepped out into the night air, and it was refreshingly cool after the hot day. Still warm enough for me to be wearing my shorts and tee shirt though.
It was blissfully quiet around here at night time. I could make out the distant laughter and hubbub of the water front bars bustling with people below us (it was around 10pm) but they were far off down the hill.
I set off walking down the stoney gravel pathways that connected the holiday cabins to each other, separated by bushes and trees. I passed a few darkened cabins meaning they were either empty, or the occupants had gone to bed already. Just a little further down the path was the cabin I recognised as Mike and Simons moms. The lights were still on there. Must be still drinking, I thought to myself as I started in that direction on my way down to the beach.
As I got closer to Simons moms cabin, I began to hear a faint rhythmic slapping sound, the sound of a man grunting, and... yes, that was Simons mom moaning too! Oh my god, they’re fucking! I thought. My heart pounded again, and with my cock beginning to swell, I quickly looked around me. There was no one around, and all the other nearby cabins were dark. Dare I? I wondered. I couldn’t resist.
Her cabin had all the curtains open, and all the lights on. I quickly nipped onto the grass up against the side of it to soften my footsteps. The sounds were coming from further round the back. I peeked into the living area window. I couldn’t see them. There were empty cans, and glasses scattered on the coffee table, and take out food cartons. The bedroom door was open at the other side of the room, and I could just make out one of her feet high in the air, and the back of Mike thrusting. But the rest of her and everything else was obscured by the door.
I need to get a better look at this, I thought. My heart pumping fast with excitement and fear of being caught, I make my way around the back of the cabin to the bedrooms at the other side. It’s completely sheltered from the paths by bushes round here, and I relax a little. I made my way along the wooden wall of the cabin to the bedroom. The sounds of them grunting and moaning became much louder as I approached their bedroom window. Slowly I raised my head up to the glass, scared to death that I might be seen but the overwhelming need to witness this for myself overriding my fear. I peeked in through the window.
If my cock wasn’t fully hard on my way round the back of that place, it was certainly bursting now. Literally pumped up full of blood. Im sure what I saw would’ve made me come instantly again, had I not already ejaculated earlier that day.
From my angle, Simons mom was laid on her back on her bed, her legs spread wide, each one of them being held apart by Mike. One leg out to the side of her, the other leg over his shoulder (this was the foot I could see waving in the air from the living room window) I had a view from the side of the bed from this window, and I could clearly see them both. Mike thrusting his cock deep into her. Both of them grunting on each thrust and she was groaning in pleasure every so often.
I couldn’t see the actual penetration as she was still wearing clothes. A short mini skirt hitched up to her hips to allow him inside her (obviously no panties) and a small crop top covering her hypnotically bouncing breasts.
I remember thinking I was disappointed that she wasn’t naked, but I still pulled out my cock and began masturbating to the scene. It was so rock hard that my bell end was actually shining in the moonlight.
Mike held her legs wide open as he pummelled away at her vulva. But just as I thought he might be about to come in her, he pulled out his dick. Mike was huge! His cock slid out of her as he pulled away, and inches and inches of it were slowly appearing before my eyes before the tip finally plopped free and bounced up on his erection. It must’ve been about 10 inches long, and girthy too! No wonder she was groaning so much. My respect for her grew even more for being able to take this monster on a regular basis. Mike spun her around so that she was on all fours, and hitched that tiny skirt up over her ass to her waist.
From my viewpoint outside, I could see her from the side. If I poked my head further into the window I could see Mike behind her, but it was risky as she would then possibly be able to see my whole face. I decided to risk it as her head was face down into the mattress anyway, her ass in the air. I also did not want to miss Mike penetrate her with that ginormous cock.
Just as I was getting myself into a good position, shuffling along further into the window with my hard cock in my hand, Mike aligned his mammoth dick up to her protruding pussy (that I could just about see bulging out between her buttocks) He pushed the tip of his Bell end into it and she gasped. He continued to slide his long thick shaft into her, she cried out as it slid deeper and deeper in until she had taken the full thing right down to his balls. It must’ve been poking her in the stomach!
He started to slide it out and back into her, she groaned loudly as she took it repeatedly. I could not believe my luck seeing this. I was masturbating furiously, the best wank I ever hard, I was so aroused. I was about ready to pop my load up against the side of the cabin right under that window frame, when Mike grabbed hold of Simons moms long blond hair (neatly scraped back into a ponytail) and pulled it, yanking her head upwards and her face towards me.
I’d gotten so complacent with my vantage point giving such a good show that my whole face was visible to her in the bottom right hand window panel. Her eyes locked onto mine. We stared at each other for a full second before I ducked down onto the floor.
Shit! Fucking hell! Thoughts were racing through my mind. Oh shit, oh shit, oh shit! I’m fucked! She saw me! Oh my god, I’m in so much trouble. As I lay there on the ground slumped against the cabin wall, my heart was now pounding out of fear rather than arousal. I kept thinking all sorts of things like; what’s Simon going to say? what’s Mike going to say?! Is he going to want to fight me? What’s going to happen now?
I started to put my dick away and move to get the fuck out of there pronto. Perhaps just deny the whole thing, like it wasn’t me. I mean there’s no way she could be sure it was me surely? But then it occurred to me that while I was freaking out on the floor, the sounds of them fucking had continued.
Yes, she was still getting fucked in there. I could hear the slapping of her buttocks against his lap as he was repeatedly thrusting his cock into her. She was still groaning from it, and he was still grunting on each thrust. There had been no pause in their sex session, not even for a second. That means... she hadn’t said anything to him?
I started to think that maybe she hadn’t seen me after all. But I knew she had. We had locked eyes. Her expression had noticeably changed when she saw me to a look of mild surprise. But yet there she still was, getting fucked by that monster dick loud and clear.
On the water front earlier that day when she had exposed her breasts to me, I had felt that she wanted to do it. She had that mischievous look about her as she had stripped, and looked delighted at my awkwardness and obvious arousal. This could only lead me to conclude, she doesn’t mind me seeing this?
Breathing heavily, still unsure about this situation, I slowly rose up the wall again to the bottom of the window frame. My heart pounding, I peek over the windowsill enough to see just the top half of her body.
She was still on her hands and knees on the bed, Mike was still behind her fucking her hard. He was still holding her hair, and her face was still pointed towards the window. She saw me again. I bobbed down again frightened, but then slowly back up. She was still looking at me. Her eyes locked onto mine again as she was being fucked.
And then there it was. The confirmation of my thoughts and ultimate conclusion. There was that beautiful mischievous little smile of hers. She was looking right at me, right into my eyes, and she smiled as she was getting fucked.
This. Was. Hot! I thought as I stared at her. Mike couldn’t see me, and he had no idea. My view was just of her down to the waist. I began to masturbate again, making sure that she could see the movement of me jerking to her. Her smile became even wider as she was continuously pounded from behind. She was loving being watched, and she was loving me wanking over her.
She shifted her position just slightly, so that she could whip off her thin crop top in one fast motion (Mike having to release her hair) before landing back on her hands on the bed. Her large juicy breasts swung madly with the movement as they escaped their cage, and continued to do so as she was being fucked.
I was almost driven mad with arousal at this sight. I was in love with her tits before, but seeing them swinging around like this as she was being pummelled from behind was just sending me to the edge. I was about to cum, and so it seemed was Mike.
He pushed her head down, pinning it to the mattress. But she turned it just in time to keep her face pointed towards the window (so she could see me) and his thrusting became faster and harder. Simons mom cried out with each strike of his lap against her buttocks as she took that huge cock to completion.
He now grabbed her by the ass, placing a hand on each of those beautifully smooth cheeks, thrusting faster and giving her the full length on each pass. I could see her teeth gritted and her brow wrinkled in pain and pleasure as she was staring right into my eyes, being forced to accept his monster cock.
Then he gave one huge thrust and cried out as he came inside her. Her mouth was open in shock. I was able to see by her expression that she had felt him unload his cum deep inside her. She was panting, but still looking right at me as I wanked off at her.
I came just as Mike pulled his massive dick out of her. It was watching his Bell end pop out of her pussy, bouncing upwards as it was still fully erect, and flicking a mixture of both his and her cum juices up her back and across the side of her face that did it for me.
She watched me, smiling that gorgeous smile of hers while the cum splashed over her face, as I ejaculated up the side of the wall. God knows what my cum face must’ve looked like, but I came everywhere. I literally painted the side of that cabin, I have never cum so hard before or since.
Mike then flopped down on the bed besides her. His huge cock hitting him in the stomach as he did, and I quickly ducked down as I was sure he would be turning to face her, and I didn’t want him to see me. It was the most intense moment of arousal I have ever felt.
I tucked my cock away and made my way back to my own cabin. By the time I got in, Simon was snoring. I lay there in my own bed wondering about tomorrow, how his mom was going to react to me, and ended up thinking: Maybe I could get more out of her....


written on
2021-12-15
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