When She Goes Away

Note: this is a companion piece to "Business Trip." When Jill goes away, Big Mike will also play. Also, to me the sex in here is all gay, gay, gay. Billy wouldn't think so, because she's a woman in a man's body. Big Mike wouldn't want to call it that, that's why he has sex with pre-op transexuals. I gave Billy her preferred pronouns, and I'm not judging Big Mike at all.

Jill and Big Mike had a marriage that suited them both. Both highly-sexed, night in and night out they pleasured each other regularly, but once in a while each of them wanted something different, something the other didn't begrudge or feel jealous about, but wasn't interested in being part of. Jill's business trips and conferences gave them the chance to indulge, kept those kinky desires from building up, and made their marriage a success.

This was another of Jill's trips away. Big Mike knew she'd be trying to get two young bucks for the night. He understood her desire to validate her sexual attractiveness, and to be sexually exhausted. He didn't begrudge her those occasional threesomes, he just preferred his sex one-on-one.

His other preference was for young, skinny, effeminate, transvestites: ladyboys, t-girls, twinks, cute crossdressers. After all, every quality a man wants in a woman Jill had in abundance. Big Mike had an itch that womanliness didn't scratch. So tonight he was playing with the most recent of his nearly androgynous little friends.

At dusk he drove his Pontiac GTO over to Billy's shitty apartment on the shitty side of town to pick her up.

Billy must have been watching for him. She ran out to the car wearing a tiny silvery tube top with spaghetti straps for a pointless bra running up over her shoulders, a matching miniskirt, and spike heels, with silver false eyelashes, silver eyeshadow, and silver glitter in her bleached hair (short on the sides, long on the top). She had a silver backpack.

Big Mike smiled as Billy slid herself into the passenger seat. She led with one foot and spread her legs wide enough that he could see her slim but long cocklet, dangling almost to the hem of the silver skirt. On their first date, Billy had her cock tucked up in a thong. She liked to pretend she didn't have one. She was saving money for her top surgery and then all the rest. She dreamed of the day she'd be a "real woman." By now she'd learned that Big Mike loved her cock. So she made sure he could see it.

"You look good enough to eat, sweetheart," Big Mike told her, licking his lips to make his salacious double meaning clear. "If you are the silver medal, I'd like to see the gold, 'cause I think the judges must be blind." He gave her a kiss. Their tongues played the tango. He wasn't that into kissing his male lovers, but Billy liked the illusion of man and woman, and he liked Billy.

The GTO sped across town to Chez Jacques. Big Mike had a reservation for two. They drank champagne and ate the finest French cuisine. Big Mike didn't give a shit who saw him with the twink; Jill knew what he was up to, and no one but Jill, and to a much lesser degree Billy, mattered to Big Mike. He enjoyed the outraged looks from the country club set as he put his hand on Billy's knee and hand-fed her oysters for an appetizer and strawberries at desert, all washed down with the bottle of champagne. At one point he smeared some whipped cream from a strawberry on Billy's lower lip, and leaned over to lick it away. Billy was innocent enough to take it all as an elegant evening out, Big Mike perverse enough to get turned on by rubbing his unnatural desire in the faces of the smart set. The waiter and maitre d were mercenary enough to remember Big Mike's past 25% tips and keep their mouths shut while giving excellent service.

Dinner over, Big Mike walked Billy out of the restaurant, one hand resting possessively on her boyish butt. Imagine holding a grapefruit in your hand. That's Billy's butt cheek in Big Mike's massive mitt.

The bucket seats in the classic GTO didn't allow for cuddling on the ride back to Big Mike's place. Billy put her hand into Mike's lap. The swelling there made her cocklet stir in anticipation, tenting up the skimpy silver skirt. Big Mike's nickname was far from false advertising.

"Pull your skirt up," growled Mike. "I want to see you play with yourself."

Billy was happy to oblige. As the GTO's big engine roared, and they raced across town, she stroked her slim, pale member into a full boner.

"You love my cocklet, don't you, Big Mike?" She said. "What are you going to do with it?"

"I'm going to suck it, Billy," said Mike. "I'm going to take it all into my mouth and throat. I'm going to lick your balls, and I'm going to stick my tongue into your asshole."

He reached over to encircle the femboy's cock with his big hand. He worked his thumb along the underside of the shaft, across the sensitive frenulum and meatus. Precum oozed from Billy. Mike gathered it with his thumb. He lifted his hand to press his fingertips to the side of Billy's face.

She turned and took the thumb into her mouth, sucking it clean. "And I'm going to do all those things to you, Da-- Big Mike. I can't wait to swallow your cum." She often called her lovers "Daddy" but Big Mike didn't like it. He called her "Honey," and "Sweetheart." She just called him "Big Mike."

At the house, Billy moved to tug the little skirt down before getting out of the car.

"Leave it," Mike said. "I want to watch your cocklet sway as you walk. I want to see your ass shining and wiggling in the night. If the neighbors see you too, so much the better. You are beautiful. They've all had an eyeful of Jill plenty of times, anyway."

In the same spirit, Mike left the front door open as they stood in the entryway and kissed. Billy slid down Big Mike's muscular form, like a child shinnying down a tree trunk. Billy pressed her face against Mike's bulging pants-front, smiled up at Mike, licked his lips, and pulled the zipper down. "I've been wanting this all night -- ever since last time." She reached her silver-nailed fingers through the fly and hoisted Mike's cock out. And out. And out.

Mike's equipment was a size-queen's wet dream. Billy's delicate pale hand could not fully encircle the engorged shaft, and when she wrapped both hands around it, the purplish glans protruded two inches beyond. She held it like that as she puckered her lips to plant several delicate kisses all over it. Then with her lips against the end opening, she slid her pointed tongue tip just into it.

Mike groaned with lustful pleasure.

Billy licked delicately at the frenulum.

Mike's big hand rested gently on her bleached and silver-spangled hair.

Stretching her jaw, Billy took the entire glans into her mouth. Her pale skin and lipsticked lips contrasted with the darker tone of Mike's shaft. Billy worked her lips at the rim of Mike's glans, bringing more moans of pleasure from the big man. She took one hand from his shaft to brace herself against his thigh. The other pumped up and down the exposed shaft in time with her lipping on the rim.

Mike's hand grasped the top of Billy's head, like an athlete with a volleyball.

Billy edged further and further onto Mike's cock, until the tip of the glans touched the back of her throat. The gentle pressure of Mike's hand encouraged her efforts. The two of them rocked together, there in the light of the entryway before the open door.

Mike's groans became more like grunts, the pressure of his hand and the thrusting of his hips stronger and faster. Billy gasped on the out-strokes and gurgled on the in.

Big Mike's phone rang with the special tone indicating the call was from Jill. He extracted his cock from Billy's mouth. "I have to take this call, Sweetheart. It's my wife. Let's go to the couch anyway."

He pushed the door shut, and answered the phone. It was the video call he'd been expecting. "Hi Jill! How's it going?"

She moved the phone to show him the two young men in bed with her. One visibly had his fingers busy at her nipple.

"Hi Guys!" Big Mike said. HIs phone was near his face. They saw nothing of his surroundings, just his face.

"Guys, here's the deal: Jill is going to do shit with you that you've probably only dreamed of, but you are NOT porn actors making porn. Treat her with respect, concentrate on HER pleasure. Make sure she cums first and frequently. If you do, it's going to be a long night with a lot of fun. Also, get your phones and send me your contact info."

The young men scrambled to comply. Quickly Big Mike grabbed a screen shot and texted it to the two. He had them show him the image: the two of them each sucking on one of Jill's love-melons, her face outside the frame. "Okay fellas. Turn your phones off. This is your souvenir picture, no more. Jill doesn't need shit out there fucking up her business career. Thanks for being cool, now have fun and pump her full of cum. Jill, I love you!"

That done, Mike turned his attention back to Billy. "Now where were we?"

"I was sucking your dick."

"What should we do now?"

"You should fuck my throat."

"Sounds good. Sit on the couch, sweetheart." He stepped out of his pants, stood before her and hoisted his cock to her mouth.

Again Billy stretched her lips around the massive glans, lipping the rim. Now Mike's hands were on the sides of the femboy's head. He pumped his hips, starting with small and gentle motions and gradually increasing the depth and speed of his facefucking. Again Billy gurgled as the glans hit the back of his throat and gasped each time Mike pulled it out. Billy worked saliva into her mouth, and each withdrawal pulled sloppy strands out to run down her chin and drool onto her boney chest. She swallowed as the glans hit her throat.

Then on one in-stroke, as Billy swallowed, Big Mike held her head firmly with both hands and jammed cock into her throat. More than half his man-meat was wedged into the twink's face. For an instant he held it there, reveling in the sensations as Billy's abused throat spasmed around his head and shaft. Then he pulled back, again dragging out a cascade of slimy saliva.

He held his cock against Billy's lips, looking down at her. "You okay?"

She nodded her head and gasped, "I like it! Do it some more."

Big Mike began a slow sawing of his cock into Billy's throat. Each penetration took him a little deeper, until Billy's nose touched Mike's lower belly each time. Saliva ran down Billy's chin, and down the underside of Mike's cock. It trailed across his balls and drooled sloppily from them. The slimy dangling strings waggled back and forth with MIke's thrusts. the chin drip and the ball drip swung to join, broke apart, and fell to the floor. A goey puddle grew there.

Mike stopped and had Billy lie on the couch, with her back propped on throw pillows and her head over the arm. He fucked her face again. Now the slime sheeted across her cheeks and into her eye-sockets. Her eye shadow ran outward and upward, beyond her eyebrows. Mike's balls swung against Billy's nose with every thrust. He repeatedly buried his thick fuck stick full length in her throat, and held it there longer and longer.

Finally, after Billy gasped and recovered for the umpteenth time, Mike sawed in and out just his glans, again letting Billy's lip stimulate the rim. His movements became faster and faster, and he pushed deeper and deeper. Then he buried himself full length. Billy's throat spasmed. Her body thrashed in distress. She involuntarily pushed at Big Mike's thighs with her tiny hands and toothpick arms.

Then Big Mike climaxed. The muscles in his back rippled and his buttocks tensed and released while his hips jerked forward and back. His vision darkened with the violence of his release. His cock exploded, pumping rope after rope deep into Billy's throat.

Only then did he relent, pulling his cock out and standing silently nearby as Billy struggled to sit, gasped, and wiped saliva across her face and down her torso. Mike's final throat assault had brought tears to Billy's eyes. Now her red-rimmed eyes, smeared eyeshadow and lipstick, and saliva-shiny, spittle-flecked face testified to the intensity of the face-fuck. She bent over, coughing and gagging. A mixture of cum and spittle sprayed from her mouth to the slime puddle on the floor. A dot of the same mixture leaked from one nostril.

When she finally finished that, she sat up. Mike had stalked to the kitchen and brought drinks: his own favorite beer, and Billy's hard seltzer. They sat side-by-side on the couch, sipping.

"That was great, Billy! You were great, " Big Mike said, throwing his arm around the femboy's shoulders.

"Was I really good for you, Da-- Big Mike?" Billy asked.

"The best, honey!" Big Mike used his arm to pull Billy in, and bent to kiss her face. The slimy nastiness of the throat mess excited him. Soon he was pressing his lips against Billy's and probing her mouth with his tongue. HIs off hand played across her pale, wet chest, pushing the silvery tube top down, and dragging the strap of the cute peek-a-boo bralette off to one side. His thick fingers found her nipple. He pinched and rolled it. Then he stopped kissing her mouth and bent to tease the nipple with his lips, teeth, and tongue. HIs hand fell to her waist, where he pulled the tube-like skirt up to find and fondle her erect cocklet.

Billy leaned her head into Big MIke's shoulder, relaxing into his strength, savoring the sensual pleasure of his tongue on her nipple and his hand on her shaft.

Big Mike gently laid Billy back on the couch. He loomed over her, then bent to put his mouth on Billy's stiffy. His tongue flicked her frenulum, then slopped around the sides of the glans. His lips tightened around the rim and worked the shaft.

Little Billy sucked more cock in a week than Big Mike had in his life, still Mike was easily able to take Billy's entire cocklet into his mouth. He slid his lips down the thin shaft until his nose pressed against Billy's pale lower belly. He could feel a muscle tremor, a barely noticeable twitching that gave away Billy's intense arousal.

Mike pulled his mouth off the cocklet and licked it up and down. He clasped the upper part in his big hand and ran his thumb over the meatus, Billy's pee-hole. He sucked Billy's shaved balls into his mouth, first one, then the other, then both at once. He licked the shaft again, swallowed the entire thing, and then managed, using his hand, to push Billy's balls into his mouth with it. Again, this is not due to special cock-sucking skill; it shows that Big Mike is big in every way, and little Billy is little. With cock and balls inside his mouth, Big Mike worked his jaw, cheeks, and lips like a liquor connoisseur savoring a vintage.

Now it was his turn to let saliva drool from his mouth. With the balls pulled up tight, there was a clear line to the femboy's hole. Mike worked his fingertips over the area, eventually circling the pucker to poke at the tight hole. He slid his index finger in and upward to press Billy's prostate.

Billy moaned his pleasure. Mike pulled the finger out and raised it to Billy's face. Billy sucked that finger like it was a little dick. Mike let Billy's balls slide from his mouth, then let his cocklet pop free, too. "Taste your sex!" Mike ordered. Then, "pull your legs up. I want to tongue your hole." For himself, he loved the nastiness of sloppy head, ass licking, teabagging -- the more taboo, the better -- but he knew Billy liked pretending she had female parts, and talk about cocks, balls, and ass could spoil her mood. Mike treated his playmates sweetly, so he could treat them roughly.

Billy pulled her legs up, and Mike dove in, swabbing his tongue over her hole, pushing the tip inside, feeding saliva into it. Meanwhile, he jacked the slender cocklet for all he was worth.

When Billy began to pant, and her cocklet twitched in his hand, Mike pulled his tongue from her rosebud and wrapped his lips around her glans. With the wet slackness of the rosebud, he was able to press two fingers inside. Again he stimulated her prostate.

"Oh, fuck! Oh, Mike! Yes, suck me, Mike," Billy moaned. Her cum flooded Mike's mouth and he held it there. Billy twitched, spurted, and softened.

Mike knelt upward, the fronts of his thighs pressing against the backs of Billy's. He pulled his fingers from Billy's ass to dribble some cum from his mouth into the palm of his hand. He smeared the cum around and into Billy's hole.

His own cock was now erect once more and throbbed against Billy's pale, softening cocklet. Mike dribbled more cum from his mouth into his hand, and massaged it all over the head of his cock. Then he gripped Billy's outer thighs, pulling his ass up off the couch. He braced it with his thighs, then used the one hand to line his cock up with Billy's cum-lubed hole.

Mike slammed his cock into Billy like a railroad spike being driven by a steam hammer. Billy's experience stretching his hole as a bottom-boi, and the slathering of cum greased the skids, but Mike's cock was the hugest Billy had ever experienced. His ass-ring burned, the passage stretched. He felt like he'd been kicked in the balls as his guts rearranged to accommodate the anal invasion. He shrieked, muffled it, grunted, and gasped in shock and pain.

"Are you all right, honey?" Mike asked. He stopped moving, but his cock was buried in Billy's backside already.

"Uh huh," Billy moaned out. "Well, I will be. Can you, um, pull out for a sec?"

Mike complied, holding his cock poised at Billy's gaping hole.

Billy spoke again, "If you lie on your back, and let me ride for a little, I'll get adjusted, and you can ream me as hard and deep as you want."

Mike laid down on the floor while Billy fished in her silvery backpack for her lube. She pushed a glob inside her hole, rubbed more on the outside, then massaged the remainder onto Mike's cock as she steered it toward her backside once more. She teased the big man, sliding just the glans in, then lifting off, dropping back on, sliding off again, then deeper.

Within a minute she was bouncing on Mike's pelvis, the big cock penetrating deep into her. Her pale skin gleamed with sweat. The silvery garments and the little bralette were bunched around her waist. Her cock, semi-hard, bounced and flopped as she slid up and down Mike's pole.

After a few minutes of that, Billy bent forward until she was nose to nose with Big Mike. "This is so good, Mike. It feels so fucking good. I love your big cock buried in me, Mike. Are you going to cum inside me? I want your cum in me."

"I'm going fill you up, honey. But first... uh, uh, uh..."

"Do you want to fuck me another way?"

"Yeah, I want you on your knees, I want doggy, baby."

Billy lifted off, quickly slid to her knees, put her forearms on the floor, and rested her head on them.

Big Mike moved behind her. He couldn't help himself from saying, "Your asshole is gaping wide open, baby. I can see the rosy red lining way inside it." He bent and ran his tongue around the rim of the open hole, collecting globs of slippery lube. Then he put both hands on Billy's skinny hips and slammed his cock back into the hole. He pounded her furiously. He used one hand to collect the lube his tongue had picked up and reached around to rub it onto Billy's glans. He clutched her cocklet tight in his fist. With his other hand he slapped her ass, moving from one cheek to the other as he pounded away, raising pink blotches on the pale skin.

Finally he brayed his lust into the air, his big cock throbbed, twitched, and erupted, spraying a fountain of cum deep inside Billy's bowels.

That triggered a sympathetic orgasm from the femboy. She dribbled jism into Big Mike's pumping fist. He held her tight in that sticky cumpocket as he collapsed on her back, forcing her from her knees to the floor.

After a minute Mike slide to one side, pulling Billy along so they spooned. He still clutched a handful of cum and cock, while his softening cock took some time to slide from Billy's hole.