“Ahhhh!” Harry moaned, ramming his hips forward... sending the girthy item straight into her moist slit – balls deep in one motion.
The mature woman roared with delight, her back arching instinctively with overt satisfaction. Nicole always loved feeling a virgin shaft penetrate her deepest parts, in the most wanton, taboo, erotic of fashions!
“So hot...” Gwen sighed, rubbing her own clit at the spectacle. “I want to be fucked just like that...”
“And indeed you will,” Nicole smiled. “But right now, it's mommy's turn! Now rail that tight pussy, virgin boy!” She barked.
Harry had no other notion on his mind. He pumped back and forth, in utter shock as it were at having his dick actually inserted into a woman... the stepmother of his very own girlfriend at that! The way her pussy gripped the sides of his love lance – how he saw her lips stick to the skin and pull out with his cock, being dragged away from Nicole's body. How far he stretched her!
The way his manhood glistened with her liquids... how he loved the sight of her massive tits banging back and forth with each of his thrusts.
“So tight... oh my god,” Harry bit his lip. “Soooo tight! Holy fuck!”
“Me! Me! Me!” Gwen whined, still furiously rubbing her own clit. “Give me a deep dicking!”
“Alright you impatient little slut,” Nicole rolled her eyes. “I'll cut this short and let you have a turn. But I hope you were paying attention...”
“Oh, I was!” Gwen reassured her.
***
***
And with that, Nicole popped the dick from her cunt and scooted over to the side.
“Let's do a side to side ramming, Harry... I can't stand to be without a cock in me for that long today,” Nicole confessed.
“I want the dick!” Gwen whined.
“And you'll get it! Come over her, kneel down beside me on all fours with your ass pointing toward Harry, next to mine. And pull those panties to the side!”
“What do I do?” Harry scratched his head, eyeballing the two delicious pussies before him.
“You, Harry,” Nicole began. “Will fuck us both! Two to three pumps per cunt and then you fuck the other one, back and forth until the first person comes.”
“Is it a contest to cum the fastest?” Gwen asked.
“Don't worry about that, honey... we're all winners here already.”
“Yeah, maybe if I get a deep dicking first! Hurry up Harry! Get that cock in me, but don't jam it in like a brute like you did in my mouth. Just ease it into me nice and slow...” Gwen barked.
Harry wasn't sure he could abide by the request. With his dick still coated in Nicole's precum... my god! He took hold of Gwen's ass, spreading those beautiful cheeks a bit and... rammed his cock into her pussy! No hesitation or gradual penetration – but yet another smooth insertion, balls deep.
“HARRY!” Gwen moaned, gripping at the walls. “Oh my god that felt so good! You're so fucking lucky my cunt was drenched, or that would have really hurt!”
“I could see you dripping,” Harry smiled, already going to town on her pussy, ramming like a wildman.
“Two to three pumps, ahem...” Nicole intoned, raising an eyebrow in contempt.
“Oh, right...” Harry blushed.
And with that he extracted his meatstick from Gwen and placed it back into Nicole... railing her pussy long and hard! Until Gwen whined, begging for the dick and so back Harry went – over and over! He fucked one girl, and then the next, and then back to the other!
The tightness of Gwen's virgin pussy... the depth and warmth of Nicole's matured goods. Both were equally impressive to him. But, being a recent virgin himself... he didn't have long at this taboo game.
Harry would fuck one girl, while grabbing the ass of the other and so forth. However, despite the great enjoyment he was experiencing... Harry felt that familiar sensation rising up in his balls. The 'oh shit I'm about to cum' feeling. And indeed he was...
“Guys... guys... guys!” Harry cried out.
“Oh fuck,” Nicole smirked. “He's going to cum! Do it in me!”
“No! No! Do it in me, Harry! I'm your girlfriend! Give me that creampie!”
The young man gripped the ass of Nicole, with his cock still buried in Gwen's southern slit as he debated which hole to blow his seed into. He knew an opportunity like this would never present itself again, and so he had to choose wisely.
Youthful, nubile Gwen?
Or mature, sexy as all hell Nicole?
“Hurry up Harry!” The women shouted at him.
And in that moment, he withdrew his mighty cock – right as it was about to explode... Harry gulped audibly, his eyes darting from one pussy and then back to the other.
The fulfillment of all his lewd fantasies was happening right before him... but strangely he'd never thought this far ahead. He never imagined himself being in this position – and so hadn't a clue where to blow his load.
“Harry quick!” They shouted. “Fuck me! Fuck me!”
“I... I... I...” He sputtered, placing a hand on both women.
When suddenly the brilliant idea occurred to him.
“Jerk me off into Nicole!” He roared.
Gwen spit in disgust, but obeyed quickly as Harry inserted his big, meaty rod back into the MILF's cunt – where she cooed like loving bird.
The younger girl then set about jerking the hefty shaft of Harry, for just a few strokes as it were – until he moaned loudly, his load of hot seed blasting out into Nicole's warm cunt.
“Oh god!” The three of them said in unison.
“I can feel it!” Gwen laughed, noting the big bursts of cum rocketing through the young man's cock.
“Oh, so can I...” Nicole nodded. “So can I!”
“Best back to school present ever!” Harry yelled.
Story 16
I was still young and inexperienced. You could say I never really had a type, or much cared to pick one. Women were all the same to me – nothing but seductive, mouth-watering mysteries – who just happened to leave me with sweaty palms, a racing heart, and a raging excitement in my nether regions…
Despite working out routinely, watching what I eat, trying to perfect my body in every way I could, there remained this lingering fear in my mind. The great unknown that was a woman’s tempting slit. But of course, being a young nineteen year old virgin, with a healthy imagination and buckets of sexual frustration… I did partake quite often in the act of jerking-off! It was my only release from this all-consuming craving.
There were days I might choke the chicken, as they say, maybe ten times or more! The feeling in me was truly insatiable. No matter how many times I took hold of the aching pole, and no matter how many times I allowed him to spray freely, he always begged for more. Simply touching myself just wasn’t enough to satisfy the hunger!
Supposedly your body can’t tell the difference – but my mind sure could! Staring at porn only killed the initial urges, the superficial desires. Those were enough to tide me over for a while. However… after the fifth or sixth orgasm, when I still felt as horny as I did at the start, I knew the problem wouldn’t go away! Some more… deviant methods were required.
And the real damn problem was I couldn’t for the life of me manage to snag a girlfriend! That would have changed everything, I’m sure. But until I could work something out on that front, in the meantime, I was left to stroke like a madman – fantasizing over every moderately (and some times quite ugly…) female I took sight of!
To make matters worse, my dad and I had lived together alone for a number of years. Ever since mom died, in fact. But he had just remarried an older woman. Probably in her late 30s or early 40s. I never did ask and women don’t seem prone to telling. Anyway, she was an attractive lady I can admit. A nice well maintained body, definitely. She had moved in not long ago. That caused a little hiccup in my routines, as you can imagine. Just little things mainly. For instance, I liked to sit at the computer late at night and jerk off when my
dad had gone to bed. It was my private time out in our computer room, so to speak.
But Rachel, my stepmother (I guess you’d say), was a bit of an erratic scheduler herself. She would awake and wander around at random times. Maybe stop off at the bathroom or make a little snack in the kitchen. Innocent things, sure… but I was busy trying to masturbate! And who knew when she would show up, appearing out from the shadows or something. The last thing I wanted was to be sitting there, jerking it to some fat-boobed girl porn, and have my stepmom come barging in!
Yeah, that would make for some interesting breakfast conversation the next morning…
***
***
Now, just to state something here, I wasn’t one of those creepy perverts who dreamed of being caught in the process of pleasuring myself. I didn’t harbor those naughty urges to be accidentally discovered or spotted by my stepmother. A nice peaceful area was my preferred choice. So I had done everything I could to ensure this. I started putting porn on my phone so I could sneak off in a more remote room, getting down and dirty with my lonesome. Don’t forget, I was jerking off like ten times a day. These were frequent shots, so to speak.
Unless I had some prior obligation or responsibility which prevented me from handling the goods, then I most definitely would be cumming as often as I could. And strangely enough, through this habit of mine, I had learned that my refractory period was nonexistent! No matter how many times I came, so long as the mental urge remained strong, so did my cock! The damn thing just would not die down! That was part of the problem, actually. Jerking off and cumming failed to relieve my urges. It might sound like heaven, but… oh, who am I kidding! It is awesome! I just wish I had a woman to share in the joy with – hopefully before I got so desperate to start naming my hands…
Take today for instance, it was around noon when the urge gripped me again (you might say it never left). It would be the sixth for the day. And it was definitely an intense one. Not something I could refrain from handling for a while. One of those that needed to be dealt with ASAP!
The problem was… Rachel! She would flit in and out of the various rooms doing god knows what! Cleaning or inspecting or cooking or whatever. I never knew where she’d show up next! Last I knew, she was in the living room watching tv while her lunch cooked in the microwave. I figured the laundry room would be a good choice for now.
And so I ducked in, shutting the door as quietly as I could. But I knew the hinge would make a loud noise if I closed it all the way, and the sound would probably send Rachel running over to investigate. So I had decided to leave it ajar somewhat. At least this way I could also hear if my stepmom was shuffling on the other side, or approaching from the far room. It seemed like a quality plan – and being so horny, I didn’t care to think over the finer details.
And then I set about doing the dirty work. That’s right, I whipped out the phone and queued up some of my favorite porn. Today’s choice was a big boobed woman with a tight ass, not unlike the shape of my stepmom, but with the pornstar camera angles, it’s hard to tell for sure. But I’d rather not fantasize about my dad’s wife, not yet anyway. I’m not that desperate!
It felt so great to be pleasuring myself again… Watching my cock grow hard to this video was always a turn on. I imagined how it would feel if the girl on screen was right here in the room with me, down on her knees, my dick pressed roughly against her mouth. She’d spread those lips, ahhh yeah! She’d spread them and take me inside! I bet it would feel so warm and hot. I wonder if she know how to flick her tongue around the tip – oh god, she did! I saw her doing the exact motion I wanted, right there in the porn scene. If the woman could only do it to me! That would make my plight so much better! A hot, sexy mature girl slobbering my knob! God, yes!
I was jerking hard and fast, starting to breathe heavily, but making a conscious effort to keep the noise down – in case Rachel had walked past and overheard anything. It might be kind of off-putting if she barged in on me mid ejaculation! But the way my cock felt, I couldn’t care less in this moment… Oh god, you know that heavy pulsating you feel just before cumming? The way your dick throbs and you feel the tightness in the tip right before the hot goo comes flying out… That’s right where I was, holding the phone in one hand and pleasuring myself with the other.
This was going to be a big load, I could tell! But as I looked around the room, not wanting to spray my nasty stuff all over the walls, I noticed there wasn’t anything for me to use! And I sure as hell didn’t want to soak it up with my own shirt! But damn… I felt so good, I couldn’t stop now! I just had to explode!
And so I grabbed the first thing I could reach – it was a pair of Rachel’s panties, sitting on top of the washer – I felt my jizz come rocketing out as I caught the liquid with the soft material, rubbing her underwear along my shaft to sop up any semen that had dripped down the pole after the initial burst.
The strange thing was… and I do feel a little funny admitting it, was that the sensation of her soft panties on the skin of my cock felt incredible! It was like a foreign hand of a goddess or something, stroking me along. Almost as if I wasn’t even participating! They were so smooth and welcoming…
This was by far the best orgasm I had experienced in recent memory. Hell, in any memory! I couldn’t believe how turned on I was by the underwear – and knowing they belonged to my busty stepmom didn’t seem to bother me in this moment. It was just her panties, after all. And knowing the material had been pressed against some real feminine bits made it all the more enticing.
However, they left me feeling so aroused that I was forced to unleash another load… right after I frantically jerked myself yet again. This time I held her panties around my shaft with one hand, letting the material massage the head of my cock, amplifying every sensation to a degree I had never known before!
With my eyes closed, I could almost imagine a sexy young girl wearing a pair just like these as she rode my cock, having pulled her underwear to the side. I would so love to have that friction of these panties sliding along the side of my meatstick as I watched it disappear into her pussy! And I could put my hands on her ass, feeling the panties gripping into her skin, all the while having the sexpot bounce up and down on my throbbing dick.
And speaking of throbbing… it was at this point that I felt that familiar sensation of my rod squeezing inward, as another load of cum fired from the tip, straight into the panties. I looked on, seeing the goo absorb into my stepmother’s panties… The purple, delightful things in my hand!
That was two intense orgasms, right in a row!
And somewhat oddly, at the end of them both, I actually felt MORE aroused than when I had started. It must be from this new method, using a pair of tantalizing panties to blow my load in…
It was at this point that the first alarming thought occurred to me – what was I going to do about these cummy clothes?! They belonged to my stepmom for Christ’s sake! What, was I just supposed to put them back and pretend like nothing happened? Let the goo dry and harden on them? Wait for her to try and put them on, only to discover that someone had jizzed in her underwear!?
And, I mean, this was an impressive load. Not some little drippy-drop orgasm. I had coated the damn things with two hefty blasts of juice. She may as well have dunked them into a bucket of glue! That’s how drenched they looked.
I did the only thing I could think of: toss them back into the dirty clothes pile, hoping she wouldn’t notice and just wash the things again… and not inspect them too closely! That might be a real mess, literally…
***
***
“We’re going out for a bite to eat, Johnny,” my stepmother called to me. “Did you want to come?”
What a fitting choice of words… just not the kind she had in mind!
“No Rachel, but thanks. I think I’ll just wait here for now,” I replied, already thinking of what naughty business I could get myself into.
“Do you want us to bring you back anything? So
me special sauce?” She asked.
I already had plenty of that saved up…
“No thanks! I’m just fine! You two have fun,” I smiled.
“Ok then,” they responded.
My father and Rachel then opened the front door and left summarily.
It was about time! I had refrained from cumming for at least three hours now… My balls were on the verge of detonating! Although, last night, I did jerk off several times – thinking back to how amazing those panties felt on my naughty bits.
That is also why I seemed so anxious to have them leave! I had been waiting all day for a chance to sneak into the laundry room and secure another pair of her underwear. My cock already throbbed with enthusiasm. I could tell by the bulge in my pants that I wasn’t the only excited one here!
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