This is one of my more goofy stories. I hope you like it. If expansion is not your thing, this story is probably not for you. Comments fuel my desire to write, so please let me know what you think. Thanks for reading.


Roger Rabbit straightened his polka-dot bow tie and stood up straight, displaying himself as handsomely as he could. Unsure he was presentable looking; Roger checked his appearance in the round mirror sitting at the make-up table next to him. His red overalls were clean but he noticed the orange tuff of hair resting between his big rabbit ears was messy, and matted it down quickly. Just as he was about to get the result he wanted, the dressing room door opened.

Roger smiled proudly and held up the bouquet of flowers he bought, his furry tail fluttering back and forth. His grin widened in excitement as the loveliest creature he had ever laid eyes on glided into the room. Jessica Rabbit, Roger’s wife, shut the dressing room door behind her, muffling the roar of thunderous applause.

Jessica’s figure was both extremely slender and totally exaggerated. A tightly clad red dress covered in sequins clung to her body, seemingly holding in her crazy curves with difficulty. The hourglass the gorgeous woman possessed was nothing short of breath-taking, always leaving Roger stunned.

Jessica’s legs were long and graceful, and lead up to the first more than generous curve of her form. Her wide hips and gratuitous rear end contrasted with her pencil thin waist, something small enough for Roger to fit his hand around. Above her midsection Jessica sported two obscenely giant breasts, barely contained by the strapless heart-shaped neckline of her dress.

The epic size of her chest could not be overstated, and it was a wonder she could stand up straight. Her breasts were truly titanic, and she exposed as much as she could to show off. The two monumental orbs were pushed together seductively, forming deep cleavage. Jessica’s top and bottom were sexy and sturdy constructs of sex appeal, while her middle was tiny and delicate.

Her pretty eyes were adorned with purple eye shadow, and her ruby lips were full and vibrant. Her long red locks reached the middle of her back, which of much her dress exposed. She was a perfect woman, and she was perfectly Roger’s.

“Hunny Bunny! I am so glad you came!” Jessica exclaimed, smiling as her high heels clacked over to her husband.

Jessica knelt down and planted a sweet peck on Roger’s cheek. The cartoon rabbit thumped a foot in approval and a loving sound hummed in is throat.

“You were spectacular tonight! You look absolutely lovely too dear,” Roger praised, love drunkenness glazing over his eyes.

Jessica stood up and scratched his ears in gratitude. After patting him on the head, Jessica walked over the table and sat in her chair. Roger followed her and leaped onto the table, staring at her in amazement.

“Did you like the show, dear?” Jessica asked, removing her long purple gloves slowly, which revealed more of her smoothly pale flesh.

“As always love dove. You were wonderful,” Roger assured.

Jessica grabbed the rabbit by his face and hugged him tightly, burying his head in between her two impressive breasts.

“Thank you for being here, I always love knowing you are in the audience, watching me,” Jessica thanked sweetly.

“I always watch you, Jessica,” Roger spoke into her chest.

Jessica released her hold on the furry creature and looked him in the eyes. She loved her husband so much, and knew the feeling was mutual. She realized he really did love watching her, all the time. Jessica wanted to reward her devoted husband.

“I learned something knew Roger…would you like to see?” she asked hesitantly.

“I love new things! Show me!” he cheered.

Jessica Rabbit stood from her chair and walked into the center of the room. The woman stretched her arm out to her side, bent her elbow away from her body, and made a small fist in front of her face. With a sultry look in her eyes, Jessica extended her thumb suggestively and placed it past her full lips. Roger’s expression was confused, but he eagerly waited.

After a moment of seemingly nothing happening, Roger became perplexed. He then noticed that his wife’s cheeks were slightly puffed, and she was blowing onto the thumb inside her mouth. He gasped when the effect finally came to fruition.

At first, it seemed that Jessica’s dress was tightening around her breasts, the fabric stretching thinner by the second. Upon closer examination, Roger realized that his wife’s boobs were steadily growing, increasing their already ridiculous size. The sparkling red dress started to tear, and threads unraveled. It could not hold the amplifying bosom for long. The expanding rack overflowed the red dress for a last struggling moment, and Jessica’s oversized breasts sprung free.

Roger stared at his wife’s two perfectly naked and round tits, now exposed to the air. Her areolas were perfectly circular and her rosy nipples were immaculate. As her nipples hardened, Roger longed to feel their softness underneath his palms.

If Roger weren’t flabbergasted already, his wife’s bubble butt was also enlarging, ripening to shelf-like status. The thin dress tore as her new rear end plumped outward, still heart-shaped and supremely defined. The impossible woman was growing at two ends, and her already excessive figure had now totally shattered the concept of ridiculousness. Jessica removed her thumb from her mouth, and her breasts and ass ceased their expansion.

The impeccable rack had grown to a preposterous proportion, and sacrificed none of its perk. The immensely large knockers hung high on Jessica’s chest, and the underside of her boobs rested near her belly. Previously wearing E- cup bras, Jessica couldn’t even guess to the size her tits had ballooned. The previously large breasts had morphed into completely flawless udders.

“What do you think Hunny bunny?” Jessica asked cautiously, giving her new baps a shake.

The motion sent waves through the sublime funbags in hypnotic fashion. Roger’s jaw literally dropped the floor as he witnessed the unrivaled pliable boobs sway side to side. He felt a craving begin within as his lust kick started. The rabbit used both hands to lift his jaw back into place, and sat on the table, totally stunned. Jessica walked to him, her swaying sending small tremors through her titties.

“Oh no, you hate my new massive milk-makers,” she lamented, her nipples inches away from Roger.

“They’re…They’re filled with milk?” Roger managed to ask, his daze still in full effect.

Jessica responded by lifting his face and shoving her left nipple into her husband’s mouth.

Roger welcomed the surprise, and immediately sucked on the supple bud. His furry, white rabbit ears danced in excitement as warm, creamy nectar oozed into his mouth. The milky present was sweet like honey, and Roger lapped it up, savoring the incredible taste. After sufficiently working Jessica’s left nipple, Roger focused sucking milk from the right breast.

Jessica smiled warmly as Roger drank his treat, small gasps of pleasure escaping her every so often. Roger gripped both of her heavenly soft tits and squeezed more milk out, most going into his mouth, some leaking over the planet-sized chesticles.

“Come now darling, I’ll give you all the milk you want, but only if you give me what I want,” Jessica said, grabbing Roger’s package.

Roger made a goofy face as he was groped, not expecting the aggressive move. He did not protest as Jessica unsnapped his overall buttons and pulled down his clothing. The crimson haired beauty stopped undressing Roger at his waist, and looked him in the eye.

“Do the red carpet roll out I love so much,” she demanded, licking her lips sexily.

“Of course,” Roger agreed as Jessica yanked his clothes down to his feet, freeing his genitals to the air.

Roger Rabbit’s penis was coiled upwards like a party blower, and his large testicles hung in a furry sack below. Following Jessica’s request, Roger thrust his hips forward and his flaccid penis unraveled as a roll of carpet would. The silly cartoon cock was incredibly long, and his penis head rolled past the edge of the table.

Jessica squealed as she watched his member unroll, loving when he displayed his impressive length. Roger’s rope did not remain flaccid for long; the sight of his wife with milk dripping from her breasts was too sexy. The dick grew hard slowly, eventually standing strong and proud, wider and longer than any normal cock.

Roger Rabbit was the owner of a gargantuan phallus, a penis only a cartoon could possess. It stretched out farther than a foot, and it was thicker than Jessica could fit a hand around. Comparably, it was wider than Jessica’s small waist. It was huge by any standard, especially compared to Roger’s short stature.

Jessica leaned over and placed the erect head near the entrance of her maw. Roger felt her warm breath on his rabbithood, and need blinded his thoughts. His wife smirked right before she took the plunge.

Jessica pushed the super-size dick past her pouty lips and began to engulf as much as she could handle. Her warm mouth accommodated only a few inches, but she forced her throat down on the penis, battling her gag reflex as she did.

Once her oral cavity had become accustomed to the immense invader, Jessica fucked the cock with her small mouth. The muscled and veiny cock spread her esophagus thinly, the outline of his dick inside her throat clearly visible. Jessica choked and her eyes watered as she struggled with the serpent.

“Yes, Jessica! Your mouth is so warm and wet. I can’t believe you always swallow my entire prick,” Roger applauded, loving how far in her throat he was.

Jessica’s red, full lips slipped up Roger’s cock, all the way to his engorged head. She teased the tip with her tongue, then plunged back down his shaft. The cartoon goddess’s throat was stretched incredibly, and the outline of Roger’s phallus could be seen testing her oral passage. Her ability to suck his cock was more than impressive, it was unreal.

Roger reveled in joy as Jessica polished his pillar, coating it in her saliva. The determined wife’s head became a blur of red hair as she quickly slid from base to head, and then head to base, on Roger’s turgid penis. She allowed the dick to assault her throat as she failed to hold back her tears. Beads of pre-cum began to ooze from the rabbit and Jessica caught his tasty gifts of the sweet load to come.

Swiftly unsheathing his log from her mouth, Jessica swooped down and licked Roger’s finely furred scrotum. The cartoon bunny gasped in pleasurable surprise as she tongued his sack and sucked a huge, round testicle past her lips. Jessica eagerly tongued the big egg, savoring the salty and sweet flavor.

After a sufficient amount of time, she shifted her attention to the other ball, polishing it ravenously. Jessica alternated her focus between the two spheres, sucking intensely as she did. As she toyed with her husband’s balls, she gripped his shaft tightly, jerking with great skill.

“I’m getting so close Jessica,” Roger cautioned softly.

Jessica ceased her good work immediately, pulling away from her husband’s genitals. A groan of protest escaped Roger, desperately wanting her touch again. Before he could ask why his wife would do such a thing, she answered him with her body.

Jessica smiled devilishly and groped the undersides of her gigantic and whopping titties. She lifted them, displaying their gravity-defying quality, pressing them together seductively. Her round and perfect nipples hardened in the air and begged to be sucked on. Jessica hovered her two perfect chest pumpkins over Roger’s throbbing cock, not quite touching him.

“Do you want my big tits, darling? Do you want me to use my stupidly heavy breasts to pleasure you? Do you want me to put your king size cock between my crazily, grossly, huge chest hangers? Do you want to feel them?” she teased, of course knowing the answer.

“Please, dear. Please use your bombastic boobs on me. Please use them,” Roger begged.

Jessica pushed her gargantuan titties over his massive mast and the member disappeared into her impossible cleavage. Invited warmly and snugly, the erect dick made a home between the breasts, surrounded by cozy bliss. Roger’s wife began to move her blimp-like breasts along his shaft at a slow and steady pace, teasing more to come. Amazed at her ability to cover his entire prodigious penis with her chest, Roger grew harder.

“You’re titanic tits are astonishing, Jessica,” Roger said in a goofy and lovey-dovey tone, enjoying his flesh cage.

“I love tit-fucking you Roger. Your dick is so humongous. How could I not love rubbing it in between my jumbo juggs?” she revealed, picking up the pace of her tit job.

Jessica worked her unrealistic udders expertly on Roger’s colonnade, sending his pleasure into an overload. She began to juggle her breasts, alternating each funbag up and down, pushing and sliding her husband’s cock around in her mammary ravine. The squishy cushions bound him inside her comfy tit enclosure.

Roger freely hummed and moaned as he approved of the job his wife was doing. He felt the pressure of his ecstasy gathering inside him, Jessica’s soft prison massaging him too well to hold out for long. His rabbit feet began to thump in the air involuntarily as his release approached.

“I want you to shoot all of your cum from this billy club,” his wife commanded, looking him in the eyes with hungry intent.

Roger needed no more persuasion. Jessica dared him to hold back his semen as she squeezed his dick with her big boobs. She pushed her mammoth mammaries together more snugly, sensing her husband’s inevitable climax. His testicles strained delightfully as the muscles in his body locked, preparing to let his load free.

A puff of smoke appeared above Roger’s ears, and when it cleared an illustrated thermometer was visible. As he reached the point of no return, his new creation responded in kind. The mercury rapidly rushed to the top, breaking the container with much fanfare.

“Jessica! You’re making me cum!” Roger happily howled.

Roger’s cock solidified as his first wave of jizz readied from his large balls. Jessica pushed her behemoth breasts down to allow Roger’s engorged head to pop out of her cleavage. She engulfed the pulsing top just as a stream of white sperm jetted from the organ. The thick load bull rushed the back of her throat, forcing itself down into her stomach.

“Swallow it all! Swallow all of my sticky goo!” Roger yelled out with a silly tone.

Jessica undertook the extreme challenge as wave after wave of liquid pummeled into her mouth. The semen was so thick Jessica could have chewed on it. She swallowed the delicious seed as quickly as possible, but did her best to savor the wonderful taste. Taking his cum like a champ, Jessica wanted one more thing before his climax finished.

The red headed bombshell retreated from the penis head between pumps of cum, and displayed her face and breasts before it.

“Paint me, darling. Paint me with your incredible gonad gravy,” she begged, holding her chest hangers up.

Roger fired a rope of splooge directly into Jessica’s face, the big stream nearly drenching her. Jessica laughed pleasantly as he continued to shoot loads onto her chest melons, soaking them in white, creamy fluid. Roger finished with a final blast, landing directly between her deep cleavage.

“Oh yes darling, you moisturized me so well,” the covered woman said.

The red head scraped a thick strand of sperm from one of her huge honkers with a lovely finger. Her tongue sexily licked it clean, delighted with the special zest. Jessica proceeded to gather the cum on her breasts and face, sucking it down, savoring the tangy flavor. After completing her task, she licked her lips clean, her skin now glistening. All of her husband’s cum was now in her belly.

Roger was just beginning to recover when Jessica slowly removed the rest of her tattered and torn dress. Jessica led Roger over to the couch, opposite the table, and sat him down. The rabbit eyed her long and sexy calves, her legs smooth and pale. Her shaven and clean womanhood was damp with desire, and Jessica turned to display her magnificent ass.

Her husband took in an eyeful of the shelf-like bum as she shook it side to side, the sway mesmerizing and seductive. The pliable flesh danced and bounced, the buoyancy of the two cheeks fluidly springing around.

Jessica’s effort did no go unappreciated. The recently flaccid penis began to rise as Roger gazed at his wife. She looked over her shoulder at him and smirked, the sexiness of her body confirmed. Jessica backed up slowly until she pushed the growing organ in between her fat ass lobes.

“Oh Jessica, that feels so good,” Roger murmured.

Roger’s cock rose to full mast as he was slapped back and forth between his wife’s elastic ass portions. When Jessica felt her good work, she positioned her hot pussy entrance before Roger’s throbbing cock head. Her husband inhaled deeply when he realized what was about to happen.

Jessica’s hot slit hovered mere centimeters away from Roger, and his hips tried to shorten the distance. Before his slow and sneaky approach created any result, Jessica lowered herself down on the drastic dong. As his head passed her entrance, Jessica’s face contorted.

“Oh god! You are so fucking thick! You are pulling my tight twat apart!” Jessica lamented, secretly loving her pain.

She continued her journey down the veiny shaft, grimacing as inch by inch was stuffed inside her. When the impaled woman looked down, she observed the most astonishing side effect of having Roger’s elephant trunk in her.

Roger’s broadness was so vast, his circumference was so great, and his width so substantial, Jessica witnessed an obscene sight. The outline of Roger’s colossal cock stretched Jessica’s skin in her pelvic area. His muscled pole crammed his wife’s pussy so completely; Jessica could see every move he made in her vagina happening on the screen that was her pelvis. As she progressed down his log, she could see his head reaching farther into her, just by looking below her abdomen.

The silhouette of her husband’s massive dick stretching her out only got Jessica hornier, and the pain of his invasion started to subside. The top of her fit thighs hit Roger’s lap, and she realized she had fit all of him inside her comparably small pussy.

“How did I fit all of you in my oh-so-snug cunt? Holy fuck Roger!” she exclaimed, amazed at her own ability.

When she thought her husband’s organ was as far as it could reach in her body, he pushed his hips upward, hitting her cervix intensely. Jessica shouted in pleasurable pain and responded by grinding on him in reverse cowgirl.

“You are so deep, Roger! You are punishing my cervix! You hurt me so good darling,” Jessica proclaimed, her grinding into Roger becoming more violent.

“You are so tight Jessica! I could never get tired of being inside your perfect twat,” the well-endowed rabbit complimented.

Roger matched Jessica’s riding by shoving his hips upwards, stretching her pussy to the limit. Jessica cried out as her crevice was tested, and proved she was an expert at taking her husband’s member. The form of Roger’s impressive spear could still be seen on Jessica’s exterior, pounding into and out of her. His colossal cartoon cock shone with his wife’s wetness, a sign of approval from the red head in heat. Jessica had never felt so full as the lovers’ sex gallop turned into a sprint.

With the pace of their fucking increasing, Jessica’s mammary mountains moved up and down uncontrollably. The vast and supple chest decorations fluidly twirled and rebounded, responding to changes in pace of the lovers’ sex ride. Her huge knockers rashly and recklessly bounced around, smacking her face as they bobbed. Seeing the opportunity, Roger decided to tame the unrestrained dynamic duo.

Subject: Jessica

Age: 26

Gender: MtF

Bra: DD

Hair: Blond

Jessica was taller than most women I knew, but more womanly than any other. Stacked, her height wasted no curve, giving her an amazingly spankable, chubby butt. She had thick, luxurious hair that she wore in an impromptu bun of gold. All night her eyes allured me with a “come hither” quality. She had candy pink lips and a tongue made of promises.

We had the greatest of nights. We’d played some old video games for maybe two hours, sharing beers and old stories about hobbies, and mutually admiring our niche tastes in music. Already, we felt like an intimate couple, an incredible match. We shared an incredible dinner at this Thai restaurant she knew. We both had such identical tastes, even in curry, that I felt like I’d finally met a perfect match. Even just going out with her, and just holding her hand gave me a sort of tingly thrill all over. Her hands were way bigger than mine, but the two felt just right pressed together.

We were both pleasantly full of curry and loaded on Singha by the time we got back to her apartment. She told me to sit down and said she had a surprise for me. I did so and she stood in front of me, towering over my short, skinny, seated self.

“What’s the surprise?” I asked her. Somehow I sensed what was coming, though, like electricity in the air. My loins stirred to life like a science fiction creature, stiffening and rising, confined against my pant leg.

Jessica leaned in, her voice husky and promising with hot breath in my ear. “My roommates are out of town…”

I turned to make eye contact and we fell into a passionate lip lock. She straddled me, let her hair down, and thrust her round, feminine tush on top of my cock through both of our jeans. I grabbed her shoulders– more solid than most other women I’d been with, but all statues of goddesses are sculpted from stones heavy, firm, and beautiful. I held Jessica closer. She looked back, our eyes met, and her wet tongue slipped into my mouth.

When she pulled away, my hands slipped down from her shoulders across her back. I lingered at her hips for a second, shyly, while I felt her breathing in concert with me, then continued down to her butt where I squeezed and held tight. Her ass was amazing and so cushiony-big, like no woman I’d ever been with before. I pinched it.

My lover moaned eagerly and started grinding her hips down into mine. “Are you getting hard for me?” she asked.

I nodded. I was already completely rock hard. “Yeah, baby, yeah…”

This hot transwoman grinded down on me hard and made some kind of bemused sound like she was laughing or scoffing that made me think she wanted it bad and was losing control. She lifted her butt up, turned around to dry hump me reverse cowgirl style right there on the couch. I gripped eagerly down on her plump booty meat in those jeans and spanked her with both hands as hard as I could, repeatedly, to encourage her. She moaned a little harder and rubbed her rear against me a little harder every time. Her booty jiggled deliciously under every strike of my palms on her pockets.

My erect cock throbbed against her. For a second I thought I was going to jizz in my pants, but I found a rhythm of deep breaths that made it work. With one hand I grabbed onto the waistband of her jeans and starting pulling down at them, bucking my hips up into her, and with the other I wound up for the mother of all spanks.


“Oooohh!” she cried. She tried leaping up from my lap, but I pulled her back down by her waistband onto the throbbing lump in my pants.

“Oh, honey, oh honey…” she moaned, still squirming from the spank, still swirling her ass on me through our jeans. I felt it then, something hard like metal rub into me for a second. Jessica turned, grabbed my face and kissed me long and hard. I didn’t hear her undo her pants, but she stood up off me finally, rubbing her butt and shedding her jeans in the same motion.

There was her wide, beautiful butt in cute, semi-see through cheekies with a ruched back and tiny, pink bows at her left and right hip. I reached up to grab one of those gorgeous moons, but without looking back she swatted my hand away. I blinked and saw what it was that had pushed into me while she rode me: the end of a metal butt plug beneath her underwear. Wrists at her hips, she walked one step, two, out of her jeans, swaying her hips. I sat mesmerized with my hand on my groin watching that juicy booty wiggle ’til she reached a door and leaned on it.

Without turning around, standing to show off her incredible curves with her back arched, she asked, “You wanna see my bedroom?”

“Yes!” I shot up to my feet, clearly ready to plow into that.

She remained more controlled, opened the door slowly, and sashayed into her room saying simply, invitingly, “Take off your pants.”

My pants were already half down. I stumbled and stood in her doorway. Jessica was bent over her bed, pulling out her plug. It was a steel toy about the size of my cock, but visibly thicker, bulb-shaped. She set it on a nearby stand with a set of dildos whose size flabbergasted me. They must have all been anywhere from 8-11 inches. My todger flexed, but felt like it was cowering.

Jessica turned around to face me and her unfastened bra slid off, revealing her mountainous, proud bosom. She put her arms around my shoulders and looked down at me. Our eyes met. She made a little face and said matter-of-factly, “You’re short.”

I didn’t think this what how she meant it, but my eyes immediately darted to the little table of dildos twice my size and bigger. I blushed a little and giggled nervously. I tried to stay debonair and grabbed her by the hips to show my confidence. “It’s alright, I like tall women.”

She leaned down and whispered in my ear, “Touch me.”

I took one of her breasts in each of my hands, feeling first where they landed upon her hard nipples and caressing her sensitive areolae. I spread my fingertips their full span across her gorgeous flesh, and as I let them wander I stood on my toes to give her a kiss. Just beneath her bosom, my thumbs traced two entrancing bands of sacred, scarified flesh.

“You’re so fucking sexy,” I whispered. I ran my fingers through her gorgeous fucking hair and felt as much as heard her wanting sigh, like from the same lungs. Slowly, I lowered myself from her lips, breathing one controlled, slow exhale down Jessica’s neck, and started making out with one of her big, amazing tits.

Again, she moaned, louder. There was something in her need, something corrupting that spread like an erotic web of milky heat throughout my brain. My naked cock touched hers, standing out of her panties and erect, or getting there despite herself. Rubbing them together, hers was clearly bigger. I felt it dig in against me. I imagined thrusting my hips at her bountiful cleavage.

Holding her tight, I flicked my tongue quickly a thousand times like a serpent across her nipple. She went, “Mm, yes,” and I just about lost it. I had only enough restraint left to nibble rather than chomp on her teat. But I had to have more.

Her push at my shoulders interrupted, parted us. She looked down at me, stroking her bitten nipple and pursing her lips. “I know what you want,” she said.

Like she’d read my mind, she got down on her knees, pushed me against the wall, and took my hard length between her tits. Only, then something happened.

“Where’d it go?” Jessica asked. My entire hard length had disappeared between her massive mammaries. She spread her boobs apart and went, “Peekaboo!” Then closed them back together over my cock again laughed.

My heart dropped into my loins and the hot web in my brain spread throughout my entire body, making my toes and fingertips tingly. I trembled with lust and embarrassment. She had corrupted me completely. I thrust my hips, totally devoid of thought, entirely given to my carnal urges. Whenever I changed the angle and thrust hard enough the head of my dick peeked up, she swooped down and kissed it, trying to get her lips around it. There just wasn’t enough for her to suck like that.

I couldn’t take it anymore. I had to be inside her. I squirmed, trying to get out of her cleavage, then tapped and lifted at her armpits. She stood over me once more. She had gone soft, and her jewels dangled cutely between her legs.

“What is it?”

“Turn around.”

“Oh…” Jessica spun, wiggled her butt at me, and spanked it. “Does somebody want this ass?”

“Yes,” I said.

Demurely as possible, she asked, “Are you gonna fuck me hard?”

“Yes.” I had run out of words.

Jessica sprawled forward onto her bed, laying on one side, and picked a small bottle of lube off an end table. I shucked my underwear off my feet and laid down behind her, rubbing myself, trying and failing to control myself against her influence. She reached back and grabbed me, lubed up my cock like a madwoman with short, rapid pumps of a fist filled with cold and wet. There was this loud, squelching sound in her lubed-up palm every time her tight fist stroked just a little too long and slipped off my dick.

I pulled her body into mine and felt the heat of her tall buttcrack against my hard tool. In my excitement, I fumbled it at her ass, trying to get it in.

“Everything okay back there?” she asked.

I grunted with surprise and told her, “Sorry, I’m not used to–”

“It should slip right in.”

I blushed, then I spanked her again, even harder for all my want and frustration.

Jessica rose up, rubbing at her butt. “Ooh, honey… let’s… try another position.” I got out of bed with her as she she stood at the edge of the bed and planted one foot on it, spreading her ass wide. “How do you like that view?”

“Very much,” was all I could say.

“Come and get it.”

Well, I tried. But for one thing, she was so tall that when she stood like that, her ass was very nearly pressed on my chest. No standing on my toes was going to help. I put a foot up on the edge of the bed, too, trying to get it in, but it was one of the most awkward positions I’ve been in. My cockhead poked at her behind and I managed to get it between between her wide, wonderful ass cheeks, but little more. I tried grabbing her shoulders to pull myself into her, but it didn’t quite work. I tried to cover it up by turning it into a massage.

“What are you doing?” she asked.

“Just… preparing.” I kneaded my thumbs into her upper back in a circular motions, to show I was serious about massage.

Jessica didn’t buy my bluff. She gave me a bemused, skeptical look. “Let’s try this.”

She laid down on the bed, flat on her stomach, and once more spread wide in anticipation. Her hole was already stretched out by her plug, and eagerly needed me. All my desire had built up inside of me, it was like a dam suddenly burst. I couldn’t hold back any longer. I got on top of her without a moment’s hesitation, pinned her down, picked my hips up, and dropped them down into her, burying my dick in her sweet, open hole. Her sphincter contracted around the head of my member, squeezing it tight. Her powerful ass flesh squeezed my entirety. I thrust in and out with abandon, closing my eyes, grunting, clenching my teeth, just letting her have it, letting loose that web of hot corruption she’d put in my brain for a few minutes, completely lost to the world in the act.

When I lifted my head from her back and looked, though, Jessica was busy playing a game on her phone. She bumped her butt back at me a couple of times, but then it was like she’d just given up trying to hump me. I knew I wasn’t exactly deep in her, barely past her sphincter if past at all, but could I have really been that bad? Then it hit me… with that plug, she’d basically had me inside of her all day without a problem. Maybe her plug was even bigger than I’d first guessed. She genuinely needed something bigger. Something the size of her toys… something more than twice my size.

“Did you get it in?” she asked, not even looking up from her game.

I clenched my teeth, tried my signature hip-drop, thrust as far and as hard as I could.

“Hurry up and finish.” Jessica sighed. “I got shit to do.”

Oh, shit. That did it. That hot, tingling web in my head, in my veins and body, was hers and I was her fly in it, helpless against the command in her voice. I felt a familiar, urgent twitch throughout my loins, pulled out, and came all over her lower back.

Jessica made some sort of noise I couldn’t identify and finally looked up from her phone at me, at her back. “That feels so weird… it’s so wet… y’know, you didn’t have to pull out. It’s not like you can get me pregnant.”

“S-sorry,” I stammered. “Old reflex.” I laid down on my back next to Jessica, spent and smiling despite myself. A bit of my semen dripped onto me.

My hot transsexual lover– perhaps no longer so in love with me– crawled forward a bit and grabbed a tissue from an end table. She tossed them at me, asking me to clean her up. I obeyed.

As soon as she was clean, Jessica got up, her hand covering over her own flaccid member, and grabbed her biggest toy from off the other table. I looked up at her pathetically. She gave me a wicked smirk and idly started sucking at the head of this big, black, basically foot long rubber dick. She deepthroated it like only the last inch was a nuisance and came up for air, a strand of her saliva strung between its head and her lips.

My flaccid penis twitched with envy and impossibility.

“Good luck getting laid with that three inch dick,” Jessica told me. “I mean, I shrank mine with estrogen, and it’s still bigger than yours.”

The hot web all over my insides turned to a numbness. “W-will I ever see you again?”

“I’ll be honest,” said Jessica, still wildly horny and idly nuzzling at the giant dildo in her hand. “I don’t ever want to see you again.” She put an (I thought unnecessary) emphasis on YOU.

“W– w– I– can’t we just be friends?”

She made a patronizing frown. “I don’t wanna get your hopes up, little boy.” After a second she added, “Actually… I think I’ll just stick to women from now on.”

I tried to speak, but nothing came out. I thought I might cry.

“Here,” said Jessica. Before I could react, she threw a strap-on at me. “I think you need that more than I do. Now, excuse me… but you can go.”

Into the bathroom she went with her toy, closing and locking the door because, no, she did not want me to watch. I laid there in numb shock until she started moaning aloud with real pleasure, probably with the whole toy inside her, reaching places I could never hope to without… well, without the toy she had just given me. It was true.

I got dressed and decided to slink out as quietly and as quickly as possible, hiding her gift to me in a bag so nobody on the street would guess. The sound of her excitement followed me out the door and into the night. The erotic, hot, or numbing web passed out from my dizzied innards at the first touch of a chilly wind and shame rushed in to fill the gap. It had seemed like such a perfect night, with such a perfect woman, but my wishfulness and expectations had gone too far, let me dream too much, and now all I had imagined had come toppling down into another pile of romantic rubble. I guess we weren’t such a perfect fit after all.

May 2018
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