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Dreams of Hypnosis (JustASweetBoyGirlThing X Lord DreamCrusher)

JustASweetBoyGirlThing

JustASweetBoyGirlThing

Planetoid
Joined
Nov 23, 2023
'Pleasure Island'

What a sleazy name for a store, it made Jacob feel gross just looking at it. He has his hoodie up (despite it being the tail end of summer) and sunglasses on (despite it being night) as he walks inside, looking around nervously to make sure nobody can see him enter. Jacob finally left for college last week, just a state school 2 hours away from home, but he has a room all to himself and no parents who can barge in randomly. This has given him the privacy to explore his sexuality a little.

He gives a nervous little wave to the person at the register and starts looking around, eyes anxiously darting everywhere. There's so much to look at, but he doesn’t wanna seem like a creep. Just focus, get it and leave. He walks up to a big wall full of dildos, clearly intimidated by it. All the toys here seem way too big for him, having only ever used his fingers before. Maybe he should get a butt plug or something to start with?

He stands there, biting his lip, heart pounding, not sure if he can work up the nerve to buy anything, considering just leaving. It's alright, breathe, this was just a practice run, you can come back some other time.
 
While the store wasn't exactly busy there were a few other people inside browsing the various sections, mostly men but a few women as well; or at least individuals that presented themselves as female in any case. The atmosphere was one laden with shyness and regret, of individuals trying to scuttle in and make their purchases before hurrying out lest they be recognized. The middle aged man working the register didn't care, he had been in this business for a long time and whatever other people were in to wasn't his concern so long as he could keep the store stocked with things they wanted to buy in any case. One individual however stood out from the rest, or at least she would if Jacob had been paying attention to his surroundings instead of his anxiety, and she spied the near trembling panic the young man was in and made it her point to saunter over while indecisiveness still gripped him.

"First time purchase?" She said aloud when she reached him, looking first at his face and then shifting her focus to the wall of dildos. Her voice was soft, smooth, and naturally sweet in a way that was relaxing and non-threatening, however she was confident and self-assured in a manner that suggested she was more than just some common floozy. When Jacob would manage to look over and take stock of who she was he'd see a beautiful woman in her late twenties, possibly early thirties, that was a few inches shorter than he was. Her skin was smooth and white with a sun-kissed hue, vibrant and healthy but far from any true tan, and her dark brown hair was long and straight as it spilled over her shoulders and extended down to the middle of her back.

Her clothing was far more ridiculous by comparison and yet she pulled it off without any trouble. Covering her chest was a light blue cropped top that exposed the underside of her modest but perky breasts while her nipples strained against the thin fabric to make their presence known; It looked like a slight jiggle could make her tits drop out at a moment's notice. Meanwhile her waist was clad in a flowing pink miniskirt that was so short it could only cover her groin when she was standing perfectly still and left the lower half of her ass hanging out. The only way she could even be considered modest with that skirt on was the fact that she wore a tiny, black thong underneath though it too barely concealed her snatch and the thin string at the rear was entirely swallowed up by her fat ass.

By actual body shape the woman was somewhat bell-shaped with a petite frame that widened out vastly at the hips to accentuate her absolutely dumptruck of an ass. Her breasts by comparison were somewhat average in size, maybe a C or a D-cup at a glance, but were comparatively large on her body to make them look delicious and perfectly suited for her build. To cap everything off she wore black leather boots than covered her shins and an odd necklace that rested atop her breasts over her shirt. The necklace was in a shape reminiscent to the symbol for female but not quite right. It also pointed straight down instead of at an angle. The metal was a pale green-gray, though shifted more towards gold somehow depending on the light, and the rounded top was inset with some kind of pink gemstone that almost gave off the impression of a pupil-less eye. Still the amulet was pretty and oddly alluring, almost like it called to the mind when one looked at it.

"Nobody here is going to bite you or anything... not unless you asked at least. Take a breath, you'll be fine. No need to run away. I'm Amalia by the way. I don't work here or anything but I can offer some advice? Help you out? From one previously closeted person to another I can tell you that taking the first steps of exploration can be far more rewarding than you might have guessed." Her candor was odd for the type of store they were in but nobody else was paying them any mind, at least not beyond ogling the woman's gorgeous body and revealing outfit anyway. Still she seemed as genuine as one could be in her desire to help him but wasn't attempting to apply any pressure to make a sale of such. Further proof of that might be found in the fact that she was holding a few choice DVD's in her left hand, having been browsing herself before coming his way.
 
Jacob instantly felt his shoulders tense as someone spoke to him, and his anxiety only grew as he saw it was this gorgeous, scantily clad woman addressing him. His eyes couldn’t help but to stare down at her barely covered tits before he quickly turned his head to the side, not wanting to stare. He, in contrast to the woman talking to him, was wearing a very baggy hoodie and jeans combo chosen specifically to hide the feminine hips and bubble butt he was so embarrassed of.

As she continued to talk, instantly clocking that he wasn't straight, his face only grew redder and redder. He turns back to her as she offers her assistance. He thinks for a moment, tucking his shoulder length brown hair behind his ears before clearing his throat and speaking quietly.

"I-I just, um, I don't know what size I'm supposed to start with." Jacob was not used to people being so candid about anything sexual. Having gone to catholic school his whole life, he was taught to be very ashamed of his own desires and not to talk about them.

“Oh I’m uh, Jacob, by the way.” Not wanting to be rude to anyone who would take the time to help him, he held his hand out to shake hers. He stood awkwardly and stiffly with his hand outstretched, like a wooden soldier.
 
"Hi Jacob~" She said sweetly and with a wide smile. Contrast to his stiff and awkward posture Amalia was relaxed and calm as she reached out to take his hand in a firm shake, one that was perhaps a bit surprising for her stature but hardly strong enough to be concerning. Still she didn't linger on the brief contact and focused on his actual conundrum of where to begin, looking to the wall again as she hummed softly. "Everyone is different but, well, I'd buy three things to start with. You want a small plug, something to help ease yourself into things. You need to learn how to relax your muscles and get comfortable first. However, you are already here and interested, so you should buy a simple dildo too for when you feel ready to move to the next stage."

Looking at the wall would afford plenty of options and narrowing down to her suggestions would certainly make things easier to manage. Of the buttplug selection there weren't very many designed for true beginners so it was mostly a matter of picking what color he might want in that regard. However, for dildos, she still had a little more to say in that case. "Pick something silicone. It's softer, more forgiving. And hey, don't go too big at first yeah? Stick between five and seven inches. You can always buy something bigger later on if you find yourself unsatisfied. Of course, the last thing is lube. Look for something water-based so it's safe with the toys."
 
Jacob nodded along to Amalia’s words, glancing between her and the toys. The strangely candid woman gave him a mix of emotions. He was thankful to have someone to help guide him through uncharted waters, but he was only made more nervous by her indecent outfit. He couldn’t help but feel that she was coming onto him, even as he told himself that she was just being friendly.

He picked up the three items she recommended. The butt plug he picks is made of pink silicone, and has an octagonal pink gem in the base. The 5 inch dildo is modeled after a circumcised cock with protruding veins and modest balls, also in pink silicone, Jacob clearly has a preference. The lube is the cheapest water based one they have, the two toys are already gonna cost him most of the money he made delivering pizzas this week. He turns back to the woman, considerably less tense than before, but still blushing.

“T-Thank you, Miss, I hope you, um-“ he glances at her DVDs “-H-Have a nice night.” He quickly turns towards the counter and tries to walk away before he can further embarrass himself in front of the nice lady.
 
Amalia didn't make any comments on his choices but just remained stationary with a faint smile, happy to help as it would seem. Though, when he stammered his thanks and moved to spin away towards the counter, she did pipe up to stop him. "Wait." She spoke with enough of an edge to make it sound almost commanding yet still friendly. Pulling the necklace up and over her head, making her breasts jiggle and bounce enticingly all the while, she extended it on offer and moved to slide it over his head while he had his hands full.

Amalia would step back and nod her approval at the look of it resting over his hoodie but otherwise had no further intentions to impede him. "Back when I was still nervous and shy, before I knew who I was and what I wanted, someone gave this to me. They told me it would help me attract what I desired. I didn't believe them at the time but, well, I'm happier than I ever used to be so maybe it worked? You should have it. Hope it helps you like it did me, Jacob." She intended to do some more shopping and thus wouldn't follow him to the register, just giving a little wave before turning and walking off to give him a perfect view of her fat ass swallowing the fabric of her thong and bouncing with every hip-swaying step she took.
 
The necklace is around Jacobs neck before he can realize what’s happening. He looks down at it, eyes seeming to lock onto it for a moment before he shakes his head and looks back up. As Amalia turns to leave he can’t seem to force any of his questions past the lump in his throat. He winds up just shyly waving back, staring at her ass as she walks away. Once he realized that he had gotten hard he finally moves to pay for his things and leave.

…

That night Jacob strips down in his dorm room. The space is sparsely decorated, two posters on the wall depict an old campy zombie movie and a local punk rock band respectively. Across from his bed there’s a small monitor with a crack in the upper right corner, and a Nintendo Switch hooked up. He discards his clothes into a laundry basket next to his bed, looking at himself in the mirror for a moment.

Jacob wasn’t very tall for a guy his age, standing at just under 5’8. He didn’t have a lot of muscle, but thankfully he didn’t have a lot of fat either. The bit of chub he did have seemed to gather in his hips and ass, much to his dismay. On his chest, accompanied by a few sparse hairs, was the strange necklace Amalia had given him. He wasn’t sure why, but he thought he looked better with it on. His 6 inch cock was slightly thicker than average, and was currently rock hard and dripping as Jacob looked at his toys laid on his bedside table.

After staring at them for what felt like hours he finally decides he’ll try them tomorrow, Friday. He has class in the morning but that night he can stay up as late as he wants, it’s just practical. Successfully justifying his nerves, Jacob puts the toys in a drawer, pulls on some boxers, hits the lights, and gets into bed. He curls up with his blanket and let’s his breathing slow down, the events of the day racing through his mind as he begins to pass out.
 
A haze would envelop Jacob's mind as sleep took him and he would wander before it cleared. It was daytime, the sun was high in the sky and the weather was warm and welcoming, and he was walking along a street somewhere downtown as cars drove by and various shops and businesses blended together in the background. Exactly what street this was no one could say, though there was an instinctive understanding that it was local for some reason that could not be explained.

The sidewalks were fairly busy with people walking by, mixing and mingling as one would expect, however the warm breeze felt much more... potent upon him than usual. With this realization he'd note a few passing glances presented him with expressions that were scrunched up as they looked his way; they didn't approve of what they saw and were judging him. He would realize soon enough the reason why; He was completely naked without even any socks or shoes on his feet. The only thing that he did have upon him was that necklace resting upon his chest.
 
Jacob didn’t know how exactly he got here or how long he had been walking, and it takes him a few steps to notice his own lack of dress. Panicking, he put both hands over his flaccid manhood, which had instantly started getting hard from all the attention. He looked all around at the judging eyes on him, feeling them stare through him, making him feel like a pervert. Blushing profusely, he quickly ran towards the first building he could find in desperate attempt to gain some privacy. He had to run in an awkward sort of half waddle to keep his sensitive balls from slapping too hard against his thighs.
 
Rushing inside the nearest store would reveal it to be a boutique catering exclusively to women. Racks and shelves of cute jeans, short shorts, skirts, and dresses filled the place as well as some simple accessories such as sunglasses, purses, or hats. While the floor plan was fairly open the racks of clothing did provide some opportunities to hide his nudity, though he couldn't escape notice by one of the employees all the same.

The woman had to be close to his age with how youthful and vibrant she appeared; long blonde hair, green eyes, and a wicker sunhat. In contrast to the curvaceous beauty that Amalia had present at Pleasure Island this woman was petite all around with a snug-fitting pink work shirt that proved she was rather flat-chested and a white skirt that came halfway down her thighs. While there was some surprise on her face regarding his nudity she took it far more in stride that he might have suspected. "Oh you poor thing. I don't know how you managed this but let's get you some clothes." Grasping Jacob's arm and pulling him deeper into the store she moved with a purpose, trying to guide his eyes to various items to see what he might be interested in. All effeminate of course but nothing slutty or whorish. "Maybe a sundress would look good with your hair? Ooh, knee-high socks and a skirt? Don't worry about the price, I'll cover everything for you this time."
 
The blushing boy was all the more embarrassed to be pitied by yet another attractive woman in yet another store he felt he didn’t belong in. This felt different though, for one the circumstances were hardly his own doing, at least he didn’t think they were, but it was hard to tell at this point. This woman also seemed to be less considerate and more… eager, in a way that Jacob found equal parts unnerving and unexplainably exciting.

He looked at all the clothes presented him, eyes lingering on a black skirt and knee socks, imagining the femboys online that he’s so often gotten off to. Certainly he couldn’t go with something like that, not when just seeing it put such dirty thoughts in his head. He grabbed a pink sundress with red roses all over it, instantly throwing it on over his head. It manages to cover him up, going down to just below his knees. Embarrassingly, however, the boys hard on is immediately visible. As soon as he notices it he throws his hands back over his crotch, shamefully staring down at the floor.

“T-Thank you, um, I-Is there any underwear I could put on?” It’s only after getting the dress on that he starts to realize there are jeans and other more practical outfits here, but the nice woman had suggested such feminine clothes, and he didn’t want to picky when someone was being so helpful to him.
 
The young woman smiled at his choice of the pink and red sundress. "I think that looks great on you." Though his follow up question of underwear made her giggle a bit, her laughter almost infectious as it was clear she was happy to help him out and thought nothing of this situation. "Of course, come on!" Again she dragged him by the arm to another section where panties were displayed on shelves for his perusal. Again the designs were very cute but still fairly modest; Various types of fabric or cotton with many bright and colorful prints on them.

"You've got to pink something that blends well with your dress. Maybe these white panties with lemons on them?" She lifted the pair and stretched them between her hands to display the pattern more clearly though even she herself wasn't really sure if they were the best pick. It almost felt like she would favor whatever he chose but the woman was clearly trying to push him a little bit. "Though you could certainly go with a pink or red pair to match if you wanted, maybe a black pair if you liked the contrast." The sundress was made for warm temperatures and rather thin. While it wasn't see-through or anything colors as dark as black might show through to a limited fashion.

Conveniently there was another set of shelves with socks right next to the underwear, though oddly all the sock types came up to at least the middle of the lower leg or up to the knee. "Oh, you need some shoes too and maybe socks. We have some cozy sneakers but maybe you'd prefer some sandals? Or low heels? I can go grab you whatever while you decide on the underwear. Just tell me what you'd like."
 
The woman was clearly getting some sort of joy out of this, and Jacob fully assumed it was at his misfortune. Still, clothes are better than no clothes, and she seemed to have his best interests in mind. As she showed off the underwear he felt his blush grow worse, crawling down his neck, threatening to consume him. He decided to wait until the woman had left to pick a pair.

“J-Just sneakers, whatever you have, I-I’m a men’s 9 but I’m not sure what that is in, um, girl sizes.” As soon as she walked away he looked back to the underwear options. At first he considers taking the black pair as it seems like the least feminine, but he worries about them being visible through the dress. This leads him to the pink pair, which he would attempt to slide on as unceremoniously as possible. He shuddered a little as they are pulled snugly (and to his surprise, quite comfortably) onto his girly butt, only further embarrassing him. Fitting less well was his boner, which he awkwardly tucked into the front of the panties as best he could. He also put on a pair of white socks, reluctantly going with the thigh highs as they covered the most skin.

Looking at himself in the mirror he was a little stunned. Sure, he was clearly not a woman (at least not a cisgender woman), he had an Adam’s apple and totally flat chest, but his figure filled out the dress rather nicely, and those thigh highs made his legs look almost hot. It reminded him of those femboys he looks at online. With some makeup he could probably… he shook his head. What was he thinking? He’s just covering up, that’s all this is. He turns to look for the friendly employee.
 
The young woman returned right on time when he had just begun to think about where she was. "Here, these should be perfect." She handed him a pair of pink sneakers that matched both his dress and his panties exactly. The design was fairly standard and looked like Converse with white soles and laces. However, instead of a star on the outsides of each heel these had a white heart sewn on. She waited for him to take them and try them on, to which they would fit equally perfectly, before she spoke up again as friendly as ever. "Now isn't that better? I think you look great and I hope you have a great rest of your day." She wasn't exactly shooing him out of the store but expected that he would want to leave now that he was dressed. She couldn't resist adding one more thing at the very least, though otherwise remained available if he had anything he wanted to ask her further. "By the way I really like your necklace."
 
Jacob shyly thanked the woman before quickly exiting the store. He didn’t want to be walking around town in a dress, he had to get… where was he going? His head felt so fuzzy trying to remember. His rushing slows down as he begins hesitantly walking down the sidewalk, looking around to try and remember where exactly he is.
 
Once back on the street he'd notice the glances from the strangers in passing had turned from judgemental to friendly with small nods of approval and brief smiles. The change was drastic and notable, though perhaps not all that odd considering he had been naked before. After a few more minutes of this travel, this haze in which everything seemed both familiar and unfamiliar all at once, his mind would slip from the dream until the sound of his morning alarm brought him back to the reality of his dorm room.
 
Jacob awoke and immediately looked all around him, confused. Oh, a dream, obviously. It felt so vivid, he couldn’t recall ever being so lucid in a dream. He dresses himself slowly as he recalls the events, while he was never one to search for divine meaning in dreams, he couldn’t help but pick it apart in his head. By the time he was buckling his belt he had come to a satisfactory conclusion, that the dream was merely some manifestation of the embarrassment he felt being approached by that woman at the sex shop. Feeling content, almost smug with this resolution, he consciously chose to forget the dream and move on with his day.

He grabbed his sweatshirt but hesitated to put it on. Its supposed to be pretty warm out today, but I feel naked without my sweatshirt on. Compromising, he tied the sleeves around his waist so the whole thing hung down like a skirt. He looked at himself in the mirror, enjoying how it looked, wondering how he hadn’t done this sooner. He began to realize he was gonna be late for his intro to Shakespeare class, quickly grabbing his backpack and rushing out.
 
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Jacob's morning class went smoothly if perhaps not terribly exciting and, aside from his decision to wear his hoodie around his waist, one couldn't really say anything had changed. Even that small decision was just that, a small and practical one that no one would bat an eye at much like Jacob himself thought little of it. The class boiled down to what most college courses ended up being, a large body of students listening to the teacher provide a lecture while they attempted to jot down or type up what notes they figured would be important for later.

Obviously not every student took such things seriously and Jacob would be able to spy at least one individual goofing off on his laptop rather than focusing, playing some kind of video game but from afar it was impossible to tell exactly which it was. Aside from that minor distraction though the students were fairly well behaved or, at the least, were non-disruptive. The class would conclude on time and leave him free to do whatever he pleased for the remainder of the day, not to mention the coming weekend that he had too look forward to.
 
When Jacob returned to his dorm he took some time to finish a small assignment for another class, send out an important email, and order a textbook he needed for yet another class. Only when he had nothing else to focus on did his anxious eyes drift back to the drawer with his new toys.

After stripping down once again he pulled out the butt plug and the lube and set them on top of the bedside table. He got on all fours and then rested his weight on one of his forearms, reaching his other hand back and teasing his virgin asshole with a lube coated finger. He’s able to get the first finger in without much trouble, his flaccid dick beginning to twitch to life, drops of precum dropping onto the towel he had put down ahead of time. He has a bit of trouble with the second finger, grunting in discomfort, but quickly adjusting, his cock growing to its full 6 inches as he teased his prostate.

Upon trying to get a third finger in he winces and pulls his hand out, panting. He holds his three slender fingers up to the toy, seeing that, at its thickest point, the toy is just slightly thicker than his three fingers. He sighs, opting to end the attempt here. He knows he can take more, he’s just scared.

Determined not to make the night a waste, he pulls out the dildo, sticking it to the wall and kneeling in front of it. Just the sight of the silicone cock right above his face tickled some part of his brain that he was still discovering. He leaned in and took the tip into his mouth, trying to imagine how he would service a real cock. He bobs his head haphazardly on the first few inches as he strokes himself, until he gets a bit too confident and tries to deep throat it. He can barely take half of it down before he pulls his head off, coughing and gagging. That’s enough for tonight. He finishes himself off on the floor, emptying his balls onto his stomach, catching his breath as he rests on his back.

After quickly cleaning up and washing off in the bathroom he shared with three other rooms, he hopped into bed and promptly passed out.
 
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Again the haze of slumber sunk into Jacob's mind, aided by his new-found necklace even though he obviously couldn't understand this. Suddenly he felt the heat of the sun beating down upon him as he walked through the desert. Dressed in the same outfit he had selected from his last dream, there was no memory of why he was out here or how he got here but the sands were endless as the dunes rose and fell and the shimmering heat radiated enough to make wavy lines in his vision.

Not a single cloud hung under the blue sky and looking around would reveal his footsteps stretching onward as far as he could see, marking the path he had taken to get to this point yet even still affording no clear place to return to. There would be a sensation that he needed to keep moving forward for some reason but the heat was draining; his muscles were weak and his tongue was swollen and dry. Dehydration was setting in and he needed water soon.
 
Jacobs eyes squinted in the bright desert sun as he trudged along. Dragging his feet through the sand made the walk all the more difficult, but he couldn’t find the strength. Having sweat through his dress he decides to take it off, holding it to his face for a moment in an attempt to cool off before just rolling his eyes and tossing it aside, delirious from the heat. Now in just panties and sneakers, he continues his walk to somewhere, anywhere he can find some comfort.
 
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His walk would continue for some time as the heat remained unbearable. With sweat beading down his now shirtless body he'd grow weaker as time went on, feeling unable to manage whatever his task truly was. Just before it got to the point that he might consider giving up however he saw a strange object as he rounded one of the dunes. It was no oasis with palm trees and water but rather some kind of statue.

Getting closer to the statue would reveal more detail and show it to be the carving of a humanoid figure standing on a small pedestal though lacking in fine details and more of a rough outline. The stone was a dull gray in color yet smooth to the touch, lacking any coarseness or roughness that rock would normally be associated with. It also was warm on contact, though much cooler than the surrounding air or sands. The concerning thing however was the fact that the statue was anatomically correct with a large scrotum carved between the legs and a proudly erect penis sticking straight forward complete with a small opening for the urethra. In terms of scale the statue did stand a few feet taller than Jacob did but, even with the pedestal, it left the cock at face level.

Having approached to look things over he would also see a small wooden sign post nearby that simply read "Suck for Water" as well as a small metal plague that was inset to the statue's thighs. This plaque was a bit harder to read due to a thin layer of dust blocking out enough of the engraving to make understanding impossible. Though he could easily brush a hand over the metal to reveal what it said if he so desired.
 
Jacob was totally bewildered at the strange sight before him. Was this a mirage, some kind of trick? While he didn’t quite believe what he was seeing, he was desperate. Totally ignoring the plaque on the thigh, he walked up to the statues large cock, taking a few deep breaths to steady his nerves. It’s just a statue, and it’s not like anyone is around to see.

He leans in and places his hands on the thighs to support himself, unintentionally beginning to wipe the dust off of the plaque. He put his lips just around the tip and begins softly sucking, shutting his eyes tight and trying to pretend it’s just a straw.
 
Wrapping his lips around the stone cock revealed the same warmth that the rest of the stone had, cooler than the surroundings and comfortable, and the smooth nature of the rock meant it was comfortable if not a bit awkward considering the shape and the circumstance. Once suction was applied he'd receive a faint trickle of clean water, perhaps the best-tasting water he'd ever enjoyed, but it was a faint trickle and thus not anywhere near enough to truly satisfy his thirst as the few drops dribbled onto his tongue slowly.

His fumbling hands brushed away the dust of the plaque, though its placement meant that he couldn't see it while servicing the statue as such. When he would pull his lips away at some point his eyes would catch the writing clearly: THOUGHTS OF COCK. Upon reading this Jacob would indeed find his thoughts drifting towards the sexual nature of this scenario, on how he was effectively forced to give fellatio to a statue in order to recover from dehydration, and yet such thoughts lingered and refused to be shaken aside so easily.

Thankfully the thoughts were faint, distant even, but they were there all the same; making him keep considering cock in all ways sexual from sucking to, well, even the thought of being taken from behind. If there was one benefit of all this it was perhaps that it revealed what he was doing wrong; he needed to really push himself to suck the statue's cock if he truly wanted a proper drink.
 
Jacobs eyes opened wide when he tasted the water, causing him to read the plaque. Initially he tenses up, but as thoughts of cock keep entering his mind he feels himself grow even more dehydrated. So thirsty.

He leans in further, taking 3 or 4 inches and bobbing his head up and down. Everytime he returns to the tip he swipes his tongue along the statues piss slit, humming softly with approval over the cool refreshing taste. He’s far too caught up in relieving his thirst to notice his own manhood coming to life and making a tent in his cute pink panties.
 
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