“Well, just promise me that you’ll take your time and think it over, alright?” Bethany said, setting Ulysses down on the small platform in the corner of the room. The full sized woman took a moment to survey his tiny accommodations, having never seen a Lilliputian's living quarters before. The rest of the room decor read perfectly like what one would expect from a girl like Jenna. A perfectly made bed with cute white and lilac sheets. A well organized desk and a myriad of different plastic totes, all labeled with their contents. However, it appeared that Ulysses had his own little space carved out for himself, with a miniature model home positioned at the end of a long shelf that stretched across the entire west wall of the room. The neatly painted “dollhouse” appeared to offer him a fair bit of privacy while the rest of the shelf offered an assortment of different accommodations. He had a small turf field and track to move around on as well as a cute looking bonsai garden with a smattering of adorable tiny furniture that looked like it offered him the ability to spend some time “outside” without taking on the risks of actual wildlife. The giantess’ lips curled up into a smile as she inspected the area. There was just something so cute about this whole little setup.
“I’d invite you inside, but… you know. Social distancing and all that.” Ulysses joked, unsure of how to deal with the awkwardness of the situation. Mrs. Bloomfield snapped back to reality when she heard her student’s voice and turned to look at him.
“Such a gentleman. But I think I should get going.” Bethany paused as she surveyed the rest of the room. “Are… are you going to be okay here by yourself?”
Ulysses clenched his fist as a small bit of frustration Welles up inside of him. “Yea, I’ll be fine. I am an adult. I’m just small.” He replied flatly. Bethany frowned a bit at his response, realizing her faux pas too late.
“I’m sorry, I didn’t mean… I’m sorry Ulysses.” She said sincerely, the sadness on her soft face instantly melting away any amount of irritation that her words had caused him.
“No, no worries. Honestly. Happens all the time.” He said, hoping to alleviate the tension. However, this just caused her frown to deepen.
“Ulysses, that doesn’t make it alright. You must know, I have a great deal of respect for you. For the choices you make. It takes a great deal of courage to embark on a journey like this one. And I hope… I hope I get the chance to be a part of that journey.” She said, her voice sounding both somber and sincere.
“I… thank you, Professor.” He replied. “I’ll get back to you, I promise.”
With that the giant woman took her leave, pulling the door shut behind her and leaving Ulysses alone with his thoughts. The young lilliputian sat down on the hammock hanging off the side of his small house. Jenna had knit it for him after he had made a comment about wanting to be able to be near her while she read and now it was his favorite place to sit and relax.
“Holy fucking shit.” Ulysses said sitting back, his head now reeling from the insanity of Mrs. Bloomfield’s proposal. He couldn’t get the image of her massive tits out of his mind, picturing the massive globes nearly spilling out of her low cut shirt. God how he wanted to just dive into her cleavage the minute she made that crazy offer. And her ass. That crazy, juicy, mind boggling ass of hers. Goddammit, what he wouldn’t give to lodge his body all the way up into that magnificent booty. It was something he had thought about countless times as he choked the life out of his own dick. And now suddenly, that was all on the table.
“Fuck. Fuck!” He shouted, storming up from the hammock in a fit of panic. All this craziness, it wasn’t about having his way with Bethany… not that he would even know what to do with her. Goddammit. There was another goddamn problem. Ulysses didn’t have any sexual experience to speak of. With lilliputs like himself and especially not with gulliverians. What the fuck was he going to do? And Mr. Bloomfield? Jesus Christ what the fuck was he going to do about that? Worship his cock? What the fuck did she even mean by that? Ulysses started to pace back and forth, his breathing becoming more and more rapid with each passing second.
Ulysses took a deep breath as a strange sense of serenity washed over him. His mind entered a frantic state of focus as a fuzzy plan began to take shape within his head. Immediately he ran into his miniature apartment, racing up into the viewing lounge where he had a gulliverian sized smartphone poised like an in house movie theater screen. Once again, it had been Jenna’s idea. A way for the two of them to watch YouTube videos together. He had his own computer that was more appropriately sized for a man of his stature. However, for what he was about to do, it seemed appropriate to put it up on the big screen.
Ulysses began typing on the massive screen and brought up a search for porn. Now it wasn’t that Ulysses hadn’t ever seen porn before, but he was much more accustomed to letting his imagination run wild whenever he felt that primal call. However, if he was truly going to go through with this insane opportunity, he was going to need to better equip himself. And so, sitting before his massive screen, Ulysses pulled open PornHub and searched up something simple to start with.
Big booty blonde gets fucked. Pretty standard, Ulysses figured. Immediately the video illuminated his viewing gallery as a large, muscular man entered into frame and started off with some stupid dialogue about being in the doctor’s office with a swollen dick. Ulysses rolled his eyes as he sat nervously in his seat. After a few more minutes of annoying, nonsensical acting the man unzipped his pants and unfurled an enormous cock that hung between his hairy legs like an anaconda. He didn’t realize it, but Ulysses had the same expression of awe and disbelief as the busty blonde playing the role of the horny nurse.
From that point forward, the pacing of the scene picked up dramatically. The young nurse quickly offered up a solution to try and alleviate her patient’s engorged erection, falling to her knees as she began to sloppily and hungrily drag her tongue across the long shaft. Ulysses watched with an uneasy curiosity as she began to suck on the man’s cock. He had never really even considered the idea of interacting with another man sexually. Though he didn’t really know if this uneasiness was a result of his own lack of attraction for his own gender, or if it was a case of inexperience induced nerves. Not to mention the fact that he couldn’t even do the things that this chick was doing. At least not to a gulliverian. No, this video wasn’t going to help him at all. He needed something more… specific.
Gulliverian couple with Lilliputian. Ulysses typed his new inquiry into the search bar, unsure of what to even expect for results. Much to his surprise, tens of thousands of videos were returned for him to pour through.
“Jesus fucking Christ.” He muttered, tracing down the list with his eyes; studying the various titles and thumbnails of each video. By this point, the tiny man’s nerves were largely offset by the mounting curiosity within. Apparently intersize sex was a bit of a hot commodity online, despite the fact that Ulysses hadn’t himself ever really heard of or known any intersize couples. With a deep breath, he calmed himself and clicked on the first video that appeared on the list.
Unlike the previous porno, this video didn’t start with what seemed like a strange cliche storyline. Instead, the opening frame showed a young blonde woman, probably similar in age to Ulysses himself, sitting on a large bed in her lingerie. From there, her scene partner entered the room, wearing what Jenna had described to him as a “banana hammock.” For a while, the pair sat on the bed making out, their hands readily exploring each other as the young lady began to remove what little clothing covered her slender frame. After a few minutes of kissing and heavy petting, the man pushed his partner back on the bed and stood before her, his hands hooking into the waistband of his own skimpy underwear. And when he finally dropped his tight cock holster to the floor, what Ulysses saw made his stomach drop.
As the gulliverian man entered the nude, Ulysses finally saw their Lilliputian partner for this video, desperately clinging to the man’s cock. The tiny woman took deep ragged breaths as she was introduced to fresh air once more. Ulysses was completely unable to take his eyes off of her as she dangled from the giant’s penis. She looked so tired, completely soaked in what he had a hard time believing was her own sweat. However, despite how much this ordeal terrified him, Ulysses was unable to tear his eyes off of the screen.
There was a voracious gleam in the eyes of the gulliverian woman as she watched her partner approach with the lilliput in tow. She playfully began to lick at the tip of the giant cock before proceeding to slather both it and the small woman with saliva as the trio began to participate in the most terrifying blowjob Ulysses could have ever imagined. He watched the helpless woman desperately cling to the dick as the giantess’ lips passed over her body time and time again. Finally the foreplay appeared to come to an end as the sexy giantess blonde fell onto her back with a giggle. The giant man approached, roughly flipping the giantess over before the camera panned down to zoom in on the exhausted lilliput, lying face down on the large fleshy rod as it began to gently tease the giantess’ wet lips. Then, much to the shock and horror of the confused student, the giant on screen proceeded to ram his erect cock inside of his partner, burying the tiny woman completely inside of her.
Ulysses began to hyperventilate. Is this what he was signing up for? He pictured a giant man picking up his tiny defenseless body and pinning him to the shaft of his monstrous cock before plunging him into the dark abyss of Bethany’s hungry cunt.
“Oh fuck, she’s squirming so much.” The man on screen moaned. The camera remained focused on his hips repeatedly rocking up against the woman’s cheeks. His strokes appeared to be intentionally short enough to avoid letting the undoubtedly tired lilliputian slide out of the larger woman’s snatch. The two full sized actors appeared to be getting a tremendous amount of enjoyment from the frantic struggling of their costar.
Ulysses was so enraptured by the frightening video that he did not even hear the door to his room open. He was also completely unaware that Jenna had just returned from her errands and was now quietly walking across the room towards her bed. It wasn’t as if the gulliverian was trying to sneak up on Ulysses, however, after she finished sending an email on her phone, Jenna was about to announce herself to her tiny roommate but was interrupted by a weird noise coming from his miniature habitat.
“Fuck… I’m gonna cum.” Jenna’s eyes went wide as she came to the realization that Ulysses was in his room watching porn. She nervously looked back and forth, trying to determine the best course of action. Part of her wanted to simply walk out of the room and come back later, however she had just gotten back and felt that would be even weirder than just breaking the tension all at once.
“Uhhhh, Ulysses?” Jenna said loudly. There was a loud sound that she could only imagine was Ulysses knocking over some furniture in a desperate attempt to silence the video. The sound finally stopped before Ulysses called back out to his roommate.
“Uhhhh, yea. Hold on. Just a second.” Jenna stood awkwardly outside of Ulysses private space until the lilliputian came walking up onto the roof to meet her. “Hey, you’re back. I didn’t hear you come in.” He said, his voice slightly wavering as he spoke. Jenna stared at her tiny friend for a long moment, studying him intently before she finally spoke.
“Yeah… sorry about that.” She said, running the back of her neck as she trudged forward through the awkwardness. “I uhhhh… is everything okay? You seem a little… upset?”
Ulysses shook his head, trying to clear his mind of all the things he had just seen. Immediately he wanted to tell Jenna about Mrs. Bloomfield’s offer. But a part of him was worried that it was out of line. At the same time, Jenna was a little bit worried that her tiny roommate was watching porn in a weird state of mind but she wasn’t sure how she could safely broach the subject. The pair shared a long moment of silence where they simply stared at one another awkwardly. Ultimately, Jenna decided to simply change the subject for the time being.
“Alright. Well, you’ll never guess wh-“
“Mrs. Bloomfield wants to fuck me.” Ulysses blurted out loudly, unable to hold this secret in for one second more. Jenna’s eyes went wide and she blinked a few times, almost as if her braid had to hard reboot after processing that sentence.
“I’m sorry… what the fuck did you just say?” She asked, reaching her hand down so that Ulysses could comfortably step into her palm.
“I, uhhh. Yea, she invited me over to…” His voice drifted off as he mindlessly stared forward into Jenna’s chest.
“To fuck? Wait, seriously?” Jenna asked, still in obvious disbelief. Ulysses nodded his head meekly, causing Jenna to erupt into a fervor of social celebration and horny jealousy.
“Holy fucking shit Yule! That’s batshit crazy.” She said, causing the tiny man to get helplessly swept up in her exuberance. He didn’t quite understand it. He absolutely hated it when people tried to use a nickname with him. Hell, he even hated the name Yule when friends from highschool tried to get something to stick. But whenever Jenna started using it, there was just something about it that finally felt… good.
“Yeah it’s… wild.” He said, still a bit in disbelief himself.
“Seriously. I can’t fucking believe it. Wait, what did you say?” She asked, coiling her hydra-like fingers around him and bringing him closer to her gargantuan face. “Please fucking tell me you said yes! Oh my god if you blew my one chance to know what her fucking pussy tastes like, then I’m seriously going to beat your fucking ass.” She said, knowing that they were both fully aware that she would never in fact harm her miniature friend.
“Well I, I told her yes. But…” Ulysses’ voice softly faded, unsure of how to explain his predicament to the smoking hot coed who certainly had no shortage of opportunities with equally hot gulliverians to explore her sexuality with.
“But what? This is a once in a lifetime sort of… oh.” Jenna fell silent as she began to piece some things together. Suddenly things started to make a bit more sense to the giantess and her heart began to ache for her tiny nervous friend. “Is that why you were… watching porn?”
Ulysses could feel his skin shifting into a bright shade of red as he realized that Jenna must’ve heard or seen something when she came in. He cursed himself internally for being so stupid and waited for the pretty giantess to burst into laughter at the sight of the tiny virgin.
“I…I…” He searched for the words to say that would lead him out of this awkward encounter without looking like a total fucking loser, but came up empty handed. Despite this, Ulysses was surprised to look up in shame only to find Jenna staring at him with a look of care and understanding in her eyes.
“Hey, it’s all good man. There’s no judgment here. Were you, like, looking for tips or something?” She asked. Ulysses gave a half hearted shrug before nodding his head. Jenna smiled gently and carried Ulysses over to her own desk, setting the small statured man on the small sofa beside her own laptop. “Let me ask you something and please, please don’t take offense to it. It’s just a genuine question. Have you ever had sex before?” Ulysses let his head drop for a moment before he shook his head no.
“Hey, it's okay. There’s literally nothing wrong with that. Plus, college is where most folks begin their journey of sexual exploration. And there’s not exactly a ton of lilliputian chicks on campus, are there?” Ulysses shook his head no again. “Exactly. So there’s literally nothing to be ashamed of. So chin up, okay?” Jenna said, using the tip of her finger to gently lift Ulysses head to meet her gaze. As the giantess beamed down at him with a genuine smile, he felt the stress lift from his shoulders immediately.
“All that being said, porn is an absolutely awful way to learn how to please a woman. Trust me. You don’t want to go down that road.” Jenna said, shaking her head with a soft chuckle.
“Well, I don’t want to go in there completely unprepared! Plus, there’s something else…” Ulysses admitted, scratching his wrist nervously. Jenna cocked her head curiously.
“What?”
“Well, apparently inviting me into the bedroom is actually a bit of a birthday gift. A gift for Mrs. Bloomfield’s husband.” Jenna stared at Ulysses for a moment before a lightbulb seemed to click in her head.
“Ohhhhhhhhhhhhh. I see your predicament now.” Jenna paused for a moment, deep in thought. “Are you bi? Like, do you have an interest in men?”
Ulysses shrugged his shoulders. “I don’t… I mean I didn’t think so. But thinking about it, I wasn’t like… immediately put off by the whole thing.” Jenna nodded her head solemnly thinking about the situation. “I mean, Mrs. B said she was going to expect me to “worship” his cock. What does that even mean? And how big are gulliverian penises anyway?” Jenna began to filter back through an archive of memories of the different dicks she’s seen in her lifetime. Immediately she was reminded of an encounter she had with a man she met at Shotty’s bar. A slight smile crept onto her face before she managed to contain herself.
“Uhh, well. I mean, it can vary. Like, a lot. Some on the smaller side might only be a couple of inches long.” Ulysses considered the math. He knew his own body was a bit less than a half inch in height on the gulliverian scale. So that would mean a penis more than six times taller than himself would still be considered small. Immediately his mind was drawn back to the man on the video and how the shrunken actress compared to its length and girth. “But, I mean I’ve seen some truly impressive cocks. Fuck, there was this guy I met last year, Eduardo, his cock was gigantic. It was about 7 inches long. Truly the biggest one I’ve ever seen. Here, look at this thing” She said excitedly, removing her phone and scrolling through several hundred photos until she managed to dig up the selfie she was searching for. She flipped her phone around to show Ulysses a picture of her from last year, lying her head on a man’s abdomen. Standing beside the redhead's smiling face was the infamous 7 inch cock of lore. The stiff, veiny hog stretched the entire length of Jenna’s head, a feat that Ulysses couldn’t accomplish with his entire body. And while Ulysses was grappling with the possibility of being faced against such a monstrous cock in the war for Bethany’s pleasure, Jenna was staring at the photo wistfully, remembering fondly all of the evenings she had spent getting split open by the massive schlong.
“Jesus Christ.” Ulysses muttered softly, forgetting that the transceiver around his neck would allow the redhead to hear even his quietest squeaks. Snapped out of her daydream by Ulysses outburst, Jenna shook her head.
“Honestly, it's a crapshoot. He could have a normal dick or he could have a really small dick.” The giantess shrugged. “Or he could be hung like a goddamn horse. You just don’t know. The cool thing about dick’s is that they’re honestly pretty simple. Or… at least straightforward.” She clarified, realizing that Ulysses size would likely make it far from “simple” to please a normal sized cock.
“And what about… Mrs. Bloomfield.” The small man asked timidly. Jenna shot him a sideways glance and followed it up with a wide smile.
“Vaginas are a bit more… complex. What makes a woman purr is entirely dependent on that particular flower.” Jenna shrugged, heaving a deep breathy sigh as more and more thoughts continued to pervade her mind. This whole situation was just crazy for her. She pictured Mrs. Bloomfield getting bent over a kitchen countertop by her muscular husband and his fat cock. She then imagined the shrill scream the blonde smokeshow would let out as her tight pussy was completely stuffed. Then, with Ulysses naked on the counter before her, big titted Mrs. B would lean forward and drag her tongue across Ulysses tiny body, stroking his own throbbing boner with her slimy muscle until he came little splotches in her mouth. “Fuck.” Jenna whispered, starting to get worked up by her own little movie scene.
“Well, any tips for learning how to please this particular… flower?” Ulysses asked, still confused by the vague concept of what he was even supposed to fucking do. Jenna snapped back to reality and returned to the conversation.
“I guess my best advice is going to be to play to your strengths. Your size could certainly be an advantage in this situation.” She said, quickly picking up her phone and sorting through her contacts. All this talk of big dicks and hard fucking was starting to get to her, and now Jenna was feeling a bit nostalgic. She sent a quick text off to a contact labeled “eDuarDo 🍆” before she returned her attention to Ulysses. “First off, being the size of a sentient sex toy is obviously going to be a big turn on for these people if they singled you out specifically. Basically just moving around and squirming up and down is gonna at the very least yield you some points.
Ulysses thought for a moment. The big dick porn star did mention something about how amazing it felt when she squirmed. He figured it would at least be easy enough to just flop his body around as a last resort.
“Here, want to do… like a demonstration or whatever?” Jenna suggested. Ulysses was stunned by the offer, not at all sure about what exactly she was proposing. The ginger giantess could see the unmitigated train of thought running rampant through her friend’s mind and decided to clarify a bit. “Relax you weirdo, I’m keeping my shorts on. But, here, get on.” Jenna lowered her hand onto the desk and Ulysses all but scrambled into her palm. She chuckled and rolled her eyes as she stood up and gently set him down to the seat of her chair. He looked up at the giantess who gave him a polite smile before spinning on her heels, displaying her massive wide bottom to him. He glanced down at his feet and realized that she had placed him dead center of the seat and she was starting to sit. Jenna squatted her body down, moving carefully as to not squash Ulyssed under her cheeks, but not slowly enough to trivialize her lesson. As her soft, wide booty came crashing down towards him, Ulysses acted on pure instinct and ran forward on the seat towards where the shadow of her crotch met the light shining between her thighs. As soon as Ulysses appeared between her thighs, Jenna allowed herself to plop fully onto the chair, knowing that he was safely between her legs.
“Alright, one point for Yule. Nice job man.” Jenna says. “There’s probably gonna be a lot of that when it happens. Hands, feet, tits, butts, balls. You’re gonna wanna stay quick on your toes and not get squished by anything.”
Ulysses nodded promptly. He knew that Jenna wasn’t actually going to hurt him, but his heart was still beating fast from having to scoot out from under her admittedly perky bum. However, his focus was now on the insane sight before him. With her soft, pale thighs on either side of him like twin mountain ranges, Ulysses was staring down the canyon that led directly to Jenna’s cotton shorts covered crotch. As he stepped forward he was immediately overwhelmed with a radiant heat and a very particular aroma. It was obviously some sort of flowery fragrance that came from some kind of perfume or her laundry detergent maybe? But there was also something else to it, something very distinct yet unfamiliar to the small man.
“Alright, so obviously, this is my pussy.” Jenna said plainly, reaching down to pull her simple red short shorts a bit tighter. The cloth constricted around her crotch as the slim amount of excess fabric was pulled up into her buttcrack, giving Ulysses a remarkably clear view of the general outline of her sex. Two plump mounds came together to form a small valley between them where Jenna’s shorts began to take on a slightly darker hue, almost as if the narrow stretch of fabric was being hungrily consumed by her enormous body. “You can see my lips, labia, if you’re not familiar. There’s so much you can do here to get things moving. Rubbing, gentle pinching, honestly just sort of making your presence known down here is gonna be pretty important. Here, why don’t you come a little closer. See if you can climb your way from the seat to riiight… here.” Jenna said, placing one finger gently on her crotch a short ways above his head. Ulysses nodded his head and began to approach, taking note of the increased heat and aroma with each and every step that he took moving forward.
The task before him was certainly daunting, despite the clear enough instructions from the giantess whose immense crotch sat in front of him, Ulysses was still perplexed on how to accomplish his task. He peered upwards towards Jenna, searching for some sort of assurance, however her face was obscured by her large tits. He let out a heavy sigh and gently placed his hands against the mound of Jenna’s vulva. The titanic woman did not immediately react with anger nor did she reprimand him for crossing any boundaries. So, with an invigorated confidence in his assignment, Ulysses began to try to scale the mountain wall of Jenna’s warm pussy, using the texture of her booty shorts to help him proceed upwards.
Jenna could feel the tiny man beginning to gently squirm around her crotch, trying to solve the puzzle of how to navigate a giantess’ cunt. A slight smirk crept onto her face as she closed her eyes and leaned her head back gently. Not that she had anything but purely platonic feelings for Ulysses, she would’ve been lying if she said that the idea of having a lilliput squirming around in her underwear wasn’t acting as a bit of a turn on right now. Suddenly her phone chimed, signaling a return text from her former paramour. She bit her lip as she read the heavily flirtatious message. She was going to need to do something about this pent up energy soon.
“Remember that Mrs. B won’t be wearing shorts when you get down there. Try not to use them as a crutch.” Jenna’s voice carried down to Ulysses who was hanging from the fabric of her shorts, dead center in the middle of her vagina. He looked to his left and to his right. What the hell else was he supposed to do? The rounded lips trying desperately to escape confinement inside her shorts hung out just beyond his own tiny body. Despite trying not to focus on this fact, he realized that if Jenna were to simply stand up suddenly, he could be completely enveloped in her monumental sex.
“Okay. So, no shorts? No shorts.” Ulysses repeated to himself. He was now drawing heavy, rapid breaths as the exertion from scaling the massive woman was beginning to get to him. Each inhale he took laid the heavy scent of Jenna’s eager sex on his tongue. This resulted in an awkward boner that was now dragging against his friend’s massive pussy. He knew in reality that she’d never be able to tell, but it was awkward nonetheless.
“Okay, alright. I’ve got this.” The small man assured himself, angling his thing frame so that his hands and feet were propped against opposite lips. This position provides him the leverage he needed to start shimmying his way up to the giantess’ clit. Ulysses finally managed to right himself, getting a bit of firm ground beneath him as Jenna’s slouched posture allowed him to sit just above the whole of her juicy mound. The small man chuckled to himself, lightly slapping his hand down on the small nub that she had signaled him to climb onto.
“Gahohh.” Jenna released a surprised groan as the sudden sensation of being essentially flicked on the clit caught her very much off guard. She lifted her shit and leaned forward to find Ulysses sitting on her crotch, waving up at her. She stared at the tiny man for a moment, trying to get a grip on herself. For a split second, the sight of her tiny friend standing on her pussy as her recently stimulated clit thrummed with excitement, Jenna considered the possibility of simply plucking him up between two fingers and sliding him down the front of her shorts. After all the work he had done to get her all revved up, it only seemed fair that he got to ride it out to the messy conclusion. However, she quickly shook that idea free from her mind.
“Alright, nice work.” Jenna said, reaching down to gently pluck Ulysses off of her shorts and set him down on her desk, closer to her face so he wasn’t talking directly into her pussy. “One note. Don’t ever just smack a woman on the clit. It’s actually a huge note. Don’t do that.” Ulysses could feel his skin turning red. He should’ve realized what a dumb idea that was.
“Sorry. I just got excited about the climb.” He admitted. Jenna shook her head and waved him off.
“No worries. It’s a learning experience. And honestly it’s good to be excited. That’s the big thing! If you’re all having fun in the bedroom, then that’s what matters most. But my advice to you is this… if you can manage to climb her lips and gently get your hands on her clit, you’re golden.” Jenna reached down to fish her shorts out of her crotch. Her phone chimed again and she gave it a quick peek. Things with Ed were picking up quickly and she needed to cut this educational segment short for the evening.
“Just keep in mind that this is supposed to be a fun experience. It’s normal to be nervous, but I can promise you that once you get in there, they’re gonna have to fight you to get you out of her pussy.” Jenna chuckled as she placed her hand down for her tiny friend to climb on. The giantess carried Ulysses back to his own house and set him on the roof. She gave him one last warm smile with a final bit of confidence. “And look, if things don’t go well, you can always call me and I’ll get you out of there. Hell, if things go sour, I’ll help you take care of your virginity problem.”
“Wait, seriously?” He asked. Jenna paused for a moment as she realized what she had just said and how strange that must’ve seemed to the tiny man.
“No I mean… I just mean that if…” Jenna tried to explain herself. “I just mean that if things don’t feel right, you don’t need to do things that make you feel uncomfortable. You’re very cute and if you put yourself out there, I think you’ll find that plenty of people will be interested.” She left a long pregnant pause before she continued. “And… if you wanted to like… I don’t know, put some notches on your belt or whatever, before you go out and try to pull on your own. I’d be cool with that.”
Jenna stared down at her tiny friend, unable to stop the slight blush from coming to her cheeks. “I mean look. I would just drop you in my panties and you’d be like a living vibrator. Talk about job satisfaction…” She said nervously laughing at her own crude joke and silently kicking herself for digging the hole that much deeper. Ulysses didn’t know what to say about that. It was a bizarre shift in his dynamic with his best gulliverian friend, but it was an offer that certainly didn’t offend him. All in all, this was turning out to be a ludicrous day.
“Uhhh, thanks Jen.” Ulysses said sheepishly. The pair shared a long moment of somewhat awkward silence, each one looking for the words that would get them past this strange crossroads, when suddenly Jenna’s phone began to ring loudly. Ulysses sighed a sigh of relief as she quickly turned her focus towards the device. Ulysses watched the young woman’s face light up as she examined the screen, before turning it to face his direction.
“It’s Eduardo! I hit him up after you got me thinking about big dicks…” Jenna said playfully, giving her roommate a knowing smirk as she picked up the call.
“Heyyyyyyyyy Eddy.” Jenna said, her voice dripping with excitement as she greeted the big dicked latino. Ulysses listens closely for a moment. He can sort of make out the voice of a guillverian man, low and somewhat gruff, but he couldn't make out exactly what he was saying to Jenna. However, the look on the cheery redhead’s face told him everything he needed to know about the contents of the conversation.
“Yeah? That’s fun.” She said, gently twirling a lock of her hair with one finger. “No, no it’s nothing like that…. Yea, no my friend and I were just talking and we got onto the subject of the biggest dick’s we’ve ever seen.” The giantess paused, waiting for a response to the bait compliment. Whatever Eduardo had said brought an entirely new smile to the coed’s face as she began to giggle cutely into the phone.
“Yeah, crazy right? Well, obviously I had to tell them about the biggest cock I’ve ever seen…” Jenna paused once more before letting out a loud, boisterous laugh, that Ulysses recognized as different from her flirty laugh. No this was a legitimate belly laugh that bordered on a piggy snort. Jenna clapped her hand over her mouth to stifle her laughter. She looked down at Ulysses with an expression of pure shock on her face. Jenna moved her hand from her mouth, she silently mouthed the words OH MY GOD to the tiny man who chuckled and returned two thumbs up.
“Oh yeah? Well you should see it now. I think it's gotten bigger since you saw me last.” Jenna leaned to the side, shooting a quick glance down towards her butt. Clearly, like any sane person attracted to the female form, this Eduardo knew to properly appreciate Jenna’s round, bubbly butt. Ulysses could help but steal a glance for himself as she leaned towards the door, aiming the sexy booty in his direction. As her jiggle cheeks returned to the surface of the chair, Ulysses couldn’t free his mind of what Jenna had told him just moments ago. He was eager and excited for his opportunity with Mrs. Bloomfield, but there was something different about Jenna’s proposition. There was something more… real, about it. Almost as if Bethany was a figment of his overactive imagination, like he was a conscious character taking part in a vivid dream come to life, but Jenna? She was his friend. They knew each other intimately and although Ulysses didn’t really put a ton of effort into seriously pursuing dating, it occurred to him that there wasn’t really anyone else on campus, or even in his life that he trusted the way he did Jenna.
“Yea? Well, why don’t you come pick me up?” Jenna asked flirtatiously. She looked over to Ulysses and gave him a quick wink. She nodded her head knowingly and moved one hand down to her crotch and began to rock her hips back and forth in the chair, pantomiming getting railed in her chair. Ulysses smiled and nodded back, celebrating his friend and her imminent dicking. He began to do some suggestive dancing of his own, placing his hands in front of his hips as he began to thrust back and forth in the air, fucking the imaginary woman from behind as he waved his hand back and forth across her ass. Jenna began to silently laugh at this display, jumping out of her chair and backing up towards Ulysses as she brought her ass back towards his house, assuming the complimentary position to the one that he was miming.
The giantess began to bounce her ass up and down, pretending to be taking backshots from her tiny friend. And because she was still focusing on her phone call as she danced, Jenna did not notice that Ulysses was no longer bouncing his hips in faux sexual display. The Lilliputian was now completely and utterly mesmerized by the incredible sight of the collegiate woman’s massive booty bouncing directly in front of him. Her massive cheeks peeked out from under her short little shorts, unable to free themselves from the depths of her steamy crack. The way her butt bounced with each shift from side to side caused another rapid gasp from the tiny man who had to apply conscious effort not to buckle at the knees as his best friend's gigantic butt rubbed against his house. He thought back to being stuck on the chair as she had begun to sit down on him. He imagined simply not running into the safety between her thighs and simply allowing this adorable giantess to plop her entire rear end onto his tiny body. And though a fear of being crushed was unfortunately all too common for people like him, Ulysses could not deny the sudden and immediate reaction that his dick had to the thought of being Jenna’s cushion.
“Cool, see you in a bit!” Jenna said, standing up to her full height. Ulysses watched with a dry mouth and tight pants as her squishy round globes gobbled up even more of her shorts, rendering them much closer to a thong than to anything one could consider outerwear. While still staring at her phone, Jenna unceremoniously stuck a finger into her crack and pried her shorts loose, ridding herself of a wedgie and creating a serious struggle for the tiny man staring straight into her ass. The plucky ginger spun on her heels and looked down at Ulysses who tried to conceal his boner, but thankfully was a bit too small to notice. She gave him an eager smile and clenched her fists together tightly. “Well, ya girl’s gonna go get dicked down hard tonight. So I’ve gotta get ready.”
Ulysses watched her begin to gather up some clothes in an overnight bag. Clearly he shouldn’t expect her to return home tonight.
“Get it girl.” Ulysses said in solidarity. He was genuinely happy for his giantess friend, simply because she appeared to be tremendously happy herself. “If Eduardo has any lilliput friends who end up getting involved tonight, have them write down some tips for me, would ya?”
Jenna snorted as she laughed. One thing she found supremely refreshing about Ulysses is that he didn’t seem to have any of that irritating possessive nature that plagued just about every other male friend she had ever had. And thankfully, her offer and their little “training exercise” didn’t do anything to change that fact. For that, she was truly grateful.
“Heh, I don’t know about that, dude. If I know Eduardo…” Jenna said, slinging her bag over her shoulder and checking her phone. “And, I know Eduardo. Then tonight I’m getting some backdoor play.” Jenna reached around and squeezed one of her own asscheeks, giving Ulysses another long look at her butt. “And I don’t know about you, but I’m not sure if that’s somewhere a lilliput would want to find themselves. I mean, I know we both appreciate a nice ass, but could you imagine actually being up in this bitch? My butt could literally swallow you whole. Anyways, I’ll be back tomorrow and we can talk some more, cool?”
“Cool beans.” Ulysses said, literally the first time he had ever uttered that phrase before. Jenna gave him a curious look, picking up on the odd turn of phrase. She chuckled as she proceeded out the door. Ulysses was still stunned by the whole interaction, not moving a muscle for several minutes. The miniature man was simply rapt in thought, considering the implications of participating in anal sex with a giantess. His mind quickly shifted from Jenna’s cute, bubbly butt to Mrs. Bloomfield’s immense, godlike ass. And just like that, his mind was made up; there was nothing at all that was going to deter him from a night with Bethany Bloomfield. Now, he just needed to prepare.