A Sissy Surprise

By smallbutmighty.


Caleb’s wife’s black boyfriend’s car was in the driveway when he got home from work and he knew she would also be taking a big cock at that very moment. He let himself in, and one of their neighbors, old Frank Costa, was sitting on the couch waiting for him.

“Hey, Caleb,” he said with a smile.

The small man set his backpack down and tilted his head back to greet the old man, prompting him to run his 60-year-old hands up Caleb’s shirt while the younger man sighed with contentment.

“Hi, Frank,” Caleb said with a dreamy smile. “Did you have a good day?”

“It was a good day because I knew I’d be coming to see my favorite sissy slut,” he said with a wink.

There was a loud moan from the bedroom.

“June is having some fun by the sounds of it,” Caleb smiled. “She loves that big cock of John’s.”

At 4:30 in the afternoon, the living room was brightly lit, with sunlight pouring in through the front window. Plants hanging from the ceiling were green and well-tended, too, adding to the feeling of positive energy in the house.

The TV was off, and the room was still, adding to the ambiance of the moment that twenty-eight-year-old Caleb was sharing with his guest, the next-door neighbor. From the other side of the wall, the sound of his wife’s creaking bed filled the house. Over the knocking of the bedpost, the woman’s moaning was audible to anyone who happened to be in the house at the time. Somehow, the sound of sex that was ringing out seemed to encourage the sissy and his guest, who were sharing a tender smile.

“I’m glad you came over,” Caleb said, smiling up at old Frank with a sparkle in his hazel eyes as he fished the man’s cock out of his pants and wrapped his left hand around the base.

At that moment, the sissy male was on his knees, resting on the backs of his legs while his guest sat spread-eagle on the couch. He’d already managed to drop his trousers and panties, leaving him naked from the waist down and exposing his rock-hard babydick. At its base was a tiny, almost undetectable patch of hairs that were matted with pre-cum that was flowing from the end of his four-inch erection.

Feeling Frank’s hot, stiffening cock against the soft skin in his palm sent a strong shiver through him that was born of desire. Unable to resist, the twenty-eight-year-old began a slow, sensual stroking of the nine-inch thick, veiny cock. At the same time, he leaned in far enough to nuzzle his soft cheek against its moist glans.

Shutting his eyes for a moment, the sissy let loose with a soft moan while he luxuriated in the hot cock he was stroking. Instinctively, the cute brunette let his saliva-coated lips graze the crown of his lover’s manhood, sending another shiver of lust through his sissy body. His sissy clit twitched on its own when he tasted the man’s pre-cum on his lower lip.

And just like that, Caleb gave in to his proclivities.

Planting a series of kisses around its diameter, the sissy tightened his grip around the meaty cock and gave it five firm strokes. When his lips had completed no less than four full revolutions around the sticky glans of his lover’s cock, the sissy slipped his experienced mouth over the mushroom-shaped head. With his hand still working near the base, the horny sissy treated himself to the top half of its length. At the same time, he greedily licked, sucked, and swallowed every drop of pre-cum that his lover’s cock was producing.

“Damn, sissy, I’m glad I came over too,” Frank groaned, reaching down and running his hand through the sissy’s layered brown mane. “I figured you’d be horny when you got home. Especially with your wife June in the throes of taking John Hastings twelve-inch black cock. I could hear her moaning from next door, the dirty slut.”

Without interrupting his pleasure-filled worship of the man’s cock, Caleb smiled up at him. He nodded with a contented sigh while his fingers and mouth worked their magic. Feeling another naughty sizzle roll through his 5’4” frame, the experienced sissy reached out with his right hand and cupped the man’s balls. Right away, the 60-year-old drew a sharp breath and worked to regain his composure, biting his lower lip as the pleasure in his loins threatened to peak early.

“Are you just going to suck cock this afternoon, buddy?” the man asked with a knowing tone, watching as the sissy shook his head no. “Then you need to pull off, Caleb. I’m ready to shoot my load.”

With a mischievous smile, the horny sissy increased the suction that he was administering to his lover’s aching cock. At the same time, he used his experienced hand to stimulate its base with an even more sensual stroking. Frank responded to the twenty-eight-year-old’s playful groping and sucking by reaching down and giving Caleb’s right nipple a little pinch, prompting the sissy to give his beau a challenging smile. In contrast, he sucked diligently on the end of his cockhead.

“If you keep that up, you’re going to end up with a mouthful of jizz, slut,” the man warned with a grin.

Pulling the long shaft out of his mouth with a wet slurp, a naughty smile spread across the twenty-eight-year-old’s face. Gripping Frank’s shaft just below the glans, he pointed the end of the cock at his grinning face and teasingly said, “Maybe that’s what I want.”

With that, he opened wide and gave the hot prick a half dozen daring strokes while he maintained eye contact with his beau. Realizing that the sissy male was about to trigger his climax, the man took a different approach.

“Why don’t you come up here so I can kiss you?” he suggested, watching with a triumphant smile of his own as the sissy immediately released the death grip around the end of his shaft and stood up straight.

With a soft moan, the sissy male leaned into his guest, and the two fell into a deep, tongue-filled kiss. While the sissy was moaning around a mouthful of stiff tongue, he reached down and wrapped his paw back around the base of Frank’s cock. With the hard-as-steel cock back in his possessive grip, the horny twenty-eight-year-old felt a flurry of romantic feelings envelop his tummy and chest. His naughty smile had melted into a warm, glowing smile of sheer ecstasy as he rested his right hand on the meaty shoulder of his lover. When he felt Frank’s strong grip on his slender shoulders, the sissy sighed deeply into the man’s mouth and enjoyed their make-out session.

As he kissed the horny twenty-eight-year-old, Frank was unable to resist the allure of letting his hands explore the sissy’s 100-pound body. He ran both of his hands down the length of Caleb’s lanky arms, using his fingertips to feel the fine fuzz that lined his warm forearms. Letting them roam further, Frank ran his fingertips up Caleb’s blue t-shirt, feeling his hot-to-the-touch torso and his imperceptible nipples. Letting his hands travel back down, he felt the fingers of his right-hand brush across the sissy’s slightly protruding navel, feeling its warm skin and making the sissy male squirm a little.

Leaving the sissy’s belly button, Frank ran his hands down a little more, running his fingers along the bald pubic bone of the little sissy, feeling the heat that poured off of his sissy erection course between his digits. He let his hand roam behind the sissy’s babydick, which was standing up at a 45-degree angle. Frank toyed with the wispy collection of pubic hairs that were sprouting at its base, noting that they were gooey with pre-cum before the old man made his next move.

“You need a fresh shave down here,” he said. “I can feel a little hair where there shouldn’t be any.”

“Sorry, Frank,” Caleb pouted. “I will do it tonight.”

“Good, girl.”

When his fingers left the sissy’s pubic bone, he traced them along Caleb’s inner thighs, then they found their way to his hot taint. This brought out a needy moan from the sissy temptress that poured into Frank’s mouth while an oven-like heat encased the ends of his fingertips.

When his fingers finally found Caleb’s hot, moist pucker, the sissy gave his hips a slow, sensual stir, and his grip tightened around the base of Frank’s cock. Using his middle finger, the man used the tip to tease its lips and was rewarded with a fresh flow of ass juice and something else that trickled out around his nail.

“What do we have here?” the man asked knowingly, breaking their kiss and raising an eyebrow as he waited for the twenty-eight-year-old to respond.

Without skipping a beat, the horny sissy smiled shamelessly and said, “It’s from earlier.”

“Turn around, sissy. I want to get a good look at what we’re working with today,” the man said with a wink, pulling his fingers out of the sissy’s crack and steering him by the hips so that he was facing away.

As soon as he felt Frank’s fingers parting his buns, the man’s wet tongue wormed its way up his hot asshole. Right away, a luscious burn engulfed his midsection, and he began to moan as the man ate him deep. The sissy’s moaning began to drown out the moans that were emanating through the wall, loud and guttural as he reached back and tried to press the man’s face deeper into his ass crack.

When his rim job ended, the sissy male wasted no time at all in laying on the couch and pulling his knees to his chest. He bit his lower lip and watched with horny anticipation as Frank crawled up to his exposed, winking hole and placed the head of his drooling cock against it. When he felt the heat of Caleb’s flexing asshole wrap itself around his glans, he took a deep breath and used his fingers to push the head in.

“Fuck, I can’t believe how hot and ready you always are, Caleb,” the man groaned, feeling his crown melt into the hot, tight entrance that the sissy was offering him. “You never get enough cock at your boi pussy, do you, sissy?”

With a set of bedroom eyes that were trained on his top’s face, the horny twenty-eight-year-old shook his head no through a breathless moan.

“You’re a bigger slut than your wife,” Frank moaned as the sounds of a woman orgasming screamed through the walls. “If that was possible.”

When the head was completely engulfed, the two shared a warm smile, then Caleb licked his lips, enjoying the aftertaste of his lover’s pre-cum as it danced on his palate. With very little effort, Frank sank another four inches into the sissy while he continued to speak to him.

“How many dicks have you taken already today?” he asked, earning him a sigh of relief from the sissy as the heat and tightness of Caleb’s rear end wrapped itself around his submerged length.

“I got laid this afternoon at work by my boss,” the sissy said with a tender tone, watching as his top sink the rest of his cockhead into his welcoming bottom, then gazing up at him with a grateful smile.

Frank’s pubic bush was smashing into his crevice, scrubbing the insides of his cheeks and making them burn sweetly while he gazed up at his lover.

“I also sucked some guy’s cock in the bathroom, too. I didn’t know him, though,” Caleb added.

“That’s hot, Caleb,” the man said, slowly pulling back with his hips before pushing back in.

Soon, he was maintaining a steady rhythm as he ran his rigid man cock back and forth in Caleb’s tight rear end.

“Ahhhh!” Caleb sighed as the unmistakable tingle of anal sex began to run its course through his sexed-up body. “That feels so good, Frank.”

“Your hot little tush feels good to me too, slut,” the man reciprocated as he fed the sissy male continuous strokes of hot cock.

Neither of them was overstating their case.

Caleb’s body was alive with carnal energy as his top ran his long, thick cockhead along the hot lining of his chute. The deep thrusts that were being administered had their intended effect, to be sure. The sissy was filled with delight, and his boi pussy was juicing heavily as he held his legs in place for his stud. He felt like he was climbing a tall ladder, with every rung bringing him closer to his ultimate ecstasy.

With every new stroke of hot cock that he accepted, his body climbed further and further, closer to the top than the last step. Just when he thought he was standing on the top rung, that he had reached the pinnacle of anal ecstasy, Frank leaned down and planted a French kiss on his mouth. With his sissy box being engulfed by the flames of gay passion, Caleb found himself climbing another ten rungs up the ladder of carnal pleasures.

On the other end of that union, Frank was rapidly approaching sexual rapture. His cock was being squeezed with unmerciful contractions by Caleb’s overflowing pleasure hole. He knew that he was about to drop a hot load into the sissy and that once it happened, their union would be complete.

Being a devoted top for the gay sissy male, he prepared himself for the moment by initiating a kiss with the moaning bottom. As he puckered his lips and leaned in, he stopped to cast his eyes on the twenty-eight-year-old’s face and smiled to himself. He was well aware that the sissy had achieved a brand of rapture, a pleasure so deep that there wasn’t a single word in the English vernacular that could describe it.

Caleb’s tiny sissy clit looked like a tiny monument that was made of stone. It was standing at full attention, and there was a seemingly endless bounty of pre-cum running out of his piss slit. His hairless little nut sack was pulled tight to his scrotum, and his testicles were bulging through the smooth skin that encased them.

From his position on top of the sissy male, Frank could see the tiny collection of pubic hair that Caleb was sporting, now glistening with so much pre-cum that they sparkled from the light that poured in through the window. Letting his gaze wander a little further down, he saw that the sissy’s hole was visibly throbbing around his thick cock as he drove in time after time.

The look on Caleb’s face told a tale older than time itself. It framed the narrative of a sissy who was in the midst of his ultimate ecstasy. It spoke volumes about pleasure so deep, so delicious, and so sinful that words could never do justice to its beauty. The smile that had spread across his sissy, cherubic face looked embedded there, almost as if he were frozen in time.

At the same time, there was a raw, almost animalistic element that Frank couldn’t place. The only thing that he could be certain of was the reality that Caleb was a completely sated sissy and that his work was finished.

Seeing that he had taken the sissy bottom to the height of anal pleasure filled him with a positive stimulus that spread endorphins throughout his body. Leaning in to kiss the sissy, Frank slipped his tongue into Caleb’s mouth and felt the sissy male’s body tense up. At the same time, the dreamy smile that had beset the sissy bottom seemed to deepen again.

He felt the sissy’s anal ring grab his stalk with an unmerciful series of compressions. At their onset, they were rhythmic and evenly timed, but out of nowhere, the pattern faded, and they came on in chaotic waves.

As Frank was reconciling this new, intensified pleasure that was coursing through his body, he felt Caleb’s feet come to rest against his shoulders while the sissy’s arms wrapped loosely around his neck. The sissy had a look of complete satisfaction on his adorable face, his bedroom eyes now filled with devotion instead of passion. Realizing that he had taken the sissy to a new sexual summit sent the man over the top.

He drove in with force as he delivered the final ten thrusts into Caleb’s throbbing asshole, feeling the cum in his balls race to the end of his cock. When he was at the point of no return, he slid deep into Caleb’s sissy pussy with as much gusto as he could muster, making sure that the head of his cock touched every nerve ending along the way.

When his load spewed forth, it was with the force of a high-powered water launcher. Each shot erupted with unchecked power, squirting out in five high-pressure streams that gave Caleb nothing but pleasure as they painted the walls of his sissy pussy. The first shot felt the best to the contended bottom, putting the exclamation point on a major rear-end service that had taken him to the highest of clouds and left him floating.

The second shot only added to his bliss, shooting hard into the hot, gooey pool of cum that he’d already accepted and encapsulating the cock that was unloading inside of him. The third shot felt like heaven as it bullied its way through the thick cum pocket that had accumulated in the deepest corner of his sissy pussy. He could feel it push all the way in like a bullet, and then it rushed into any available space it could go to.

When the fourth and fifth shots erupted, he was delirious with pleasure as the load began to overflow from his hole, running into his crack in both directions. He could feel Frank’s load running down his crevice and all over the small of his back, where it cascaded over the vertebrae of his spine. At the same time, there was hot semen pouring over his taint and streaming around his nut sack until it matted into the pubes behind his rigid, tingling, sissy clit.

When Caleb knew that his stud had finished breeding him, he cupped the back of Frank’s head and kissed him for another full minute. He loved how the man’s cock felt as it rested in his clutching chute, stirring around the thick load of cum that he’d put there. When they finally broke their kiss, they shared a tender smile while Frank slowly withdrew his cock.

As soon as it was out, the sissy sat up and wrapped his lips around it, eager for the chance to worship it again. Caleb’s stiff cock was burning with naughty pleasure, producing pre-cum at an accelerated rate. At the same time, he moaned hotly around the cock in his mouth. Frank’s massive erection was lined with thick dollops of cum that dangled from every inch, giving the sissy male nothing but pleasure as he sucked them into his mouth and swallowed.

After a pleasure-filled afterglow licking and sucking his man clean, the horny sissy pulled the cock out of his mouth and moved in for one last kiss with his suitor.

As their tongues danced, both man and sissy realized that the house was quiet. The creaking of the bedpost had stopped, and Caleb’s wife was now sleeping soundly beside her bull. The sissy male shared a knowing smile with his top as soon as it dawned on him that his wife of eight years was asleep. He could feel that same sleepy afterglow creeping in on his exhausted body.

“Are you all better now, Caleb?” Frank asked, watching as the glowing little sissy nodded in the affirmative.

“Do you think you might want to come see me again tonight?” Caleb asked with a hopeful smile, prompting the man to run his fingers through the sissy’s brown hair. “I was kinda thinking that maybe you could see me in my room for a nightcap.”

“Oh yeah?” Frank asked, and the sissy nodded with a starry-eyed smile. “Do you think you’ll be up for another ride by then?”

The sissy nodded his eager answer with a look of longing in his sissy eyes, prompting the man to gush as he considered the horny disposition of his sissy host. Giving in with a wink, Frank leaned down and shared a final kiss on the lips with the sissy, earning him a dreamy sigh from the sissy male before they both got up and put their pants back on.

 

The End.

 

*AI has edited this story to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story was submitted directly to this website. Thank you so much for sharing your story with us.

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