Jake's Surprise Pt. 02

Jake was sucking Sissy's mosquito bite nipples as his rough hands raised her up and down on his slut hungry cock. Her hands were on his thighs, supporting his pumping her body...her head looking up at the ceiling enjoying how he bit her nipples.

It had been a month since Jake got his first blowjob from Sissy. Sometimes he saw her once or twice a week, other times he was taking advantage of her most of the week. It all depended on how busy his work schedule was.

"Uh uh uh uh" Sissy moaned.

The bouncing on his cock continued, the bed creaking in response. Sissy looked at him, her eyes locking on his. She brought the her arms onto his shoulders, her face glazed over with pent up sexual tension...waiting for the release that she craved so much.

"Kiss me," Jake demanded.

Sissy leaned in and kissed his lips and started tonguing his mouth. It was the first time they had kissed. Sissy's breath caught in her throat, she wanted to cry. It was odd that such a tiny thing could mean so much to her, but it did.

Her body suddenly orgasmed, her prostate well massaged and titillated. She was gasping for air, her body seemingly no longer hers to control.

"F U C K" she screamed!

But Jake wasn't done with her. He quickly laid her down and pulled her legs wide open. He began railing her boipussy like a freight train going downhill. Sissy pulled her tiny scrotum back so Jake could have his way with her. She was orgasming again as Jake pummeled her behind.

"Gah! Oh fuck yes!" Jake hollered. "Mmm, yeah take that cum, little girl!"

He fell on her kissing her deeply, then one of his hands started pinching her nipples.

"Who's my little slut? Who's my delicious little whore?"

Sissy couldn't take it, her tears started running down her face.

"I am. I'm your slut, I'm your whore."

"Hey, what's wrong?"

She shook her head, not able to talk about it yet. She took several breaths to calm herself. After several deep breaths, she said,

"You kissed me!" in an emotional voice.

Jake didn't know what to say, he didn't understand why that was a big deal. Then it came to him, the scene in Pretty Woman with Julia Roberts. In the movie, she says "No kissing" because it was too intimate.

Jake reached down and kept kissing her. He crawled around in bed and dragged her on top of him like a blanket. He spent the next several minutes kissing her as deeply as she wanted. Sissy responded by pulling away and playing games, giving Jake tiny kisses on his lower lips, rimming her daddy's lips with her tongue. All the while, Jake's arms caressed his sissy's back with his arms.

"Better?" Jake asked.

Sissy collapsed on his chest. Her hands rubbed his chest, the hair longer now. She started licking and kissing Jake's nipples. Jake smiled, he liked it.

"Better!" Sissy whispered, falling asleep on top of Jake.

************

Jake pulled into work, and jumped out of his truck. He walked into the trailer on the job site, he checked his mailbox for paperwork. He rifled through it, tossing the crap and getting the stuff that deserved his attention. Looking over it, he signed the relevant materials, and walked them over to Darlene. He handed them to her and was about to walk away.

"How come you never smile at me anymore Jake," she asked.

"Huh? What do you mean? I'm just in a rush, that's all." he smiled.

"You got yourself a girlfriend, didn't you?" She gave him a wondering eye.

He gave her a confused look. Shrugged, and started to walk out.

"One of these days I'm going to seduce you Jake, and you're gonna love it!"

Jake knew exactly what she was talking about. As he walked to his truck, he remembered he had made innuendo's to her, and straight up flirted with her several times. That had all ended the weekend he had come across Sissy. He made a mental note, if she could tell, others might suspect something too. That got his wheels turning.

Later that day, once he had a chance to relax a bit, he thought about Sissy and his 'problem' with Darlene. He could probably easily get Darlene in bed, but did he want to anymore? He did not have an answer to that. It would, however, help with office gossip though. His other problem was, despite using Sissy like his personal prostitute...he knew she was developing feelings for him. The more Jake thought about it, the more he was confused about how he felt about Sissy. He definitely didn't love her, and she was easy enough to be around because they were constantly fucking...but he knew this couldn't last the way it was going.

Suddenly, he remembered a phone call from years ago. Back when he had been dating his soon to be ex-wife. His brother had called him out of blue, they had shot the shit. When the conversation seemed like it was ending, his brother had asked if he was going to make an honest woman of Tricia, his girlfriend at the time.

"Where is this coming from?" Jake had asked.

"Oh nothing," his brother sidestepped, "Marlene had asked me about you two."

"You mean she asked if I was going to propose to Tricia any time soon?"

"That about sums it up."

"So that time we had dinner at your place, and the women were in the kitchen talking...sounds like they were laying the groundwork," Jake observed.

"Maybe, but you gotta admit, you've been dating her *cough* *fucking* her for three years now. Let me tell you brother, guys take relationships for granted. Women take them as a possible marriage. That's the difference between men and women."

"Huh, yeah I can see that. I'm just not sure she's the one."

"Look, if you're waiting for a fairytale romance, that ship has sailed. At some point you have to face facts, you aren't getting any younger. Neither is she. And she has a biological clock. Women will cut their losses and move on. Then you'll be sitting around thinking 'what did I do'. The truth is, it's 'what you didn't do'."

"Hmm, I'll have to give it some thought."

Well, damn it, thought Jake, he had married Tricia. It lasted another three years before they got divorced. Jake just figured he wasn't lucky at relationships. He loved the sex, but he just didn't clue in well about people's emotions. And that's the pickle he was in. Once again, he had a girl falling for him, and he just wanted sex.

"Fuck," he exhaled.

**********

It was Friday, and Jake was going to happy hour. The week and blown by, and largely because he had been so busy. Work had piled up and he was ready to get out and blow some steam. There was no way he was going to work late today, not Friday. Right after work, he drove to Taps, a restaurant/brewery. He sat at the bar, and ordered his favorite beer and onion rings. The game had just started and didn't notice when Darlene walked up behind him. She gently tapped him on the shoulder.

"Oh hey Darlene, I didn't expect to see you here."

"Why don't you join me and Maxie at our table. You walked in and went straight to the bar without noticing us."

"Uh, I guess I did, didn't I?" he grimaced. "Sure, I'll join you."

He followed her to a table where Darlene had been sitting with Maxie. He sat opposite both of them and gazed at them. Darlene was close to ten years older than him. Maxie, he had only seen a few times around the office. She looked Asian, but he couldn't put a finger on it.

"I was just telling Maxie I plan on seducing you, but she says I'm bluffing. What do you say Jake?"

Maxie had a wicked grin, both ladies seemed to have several drinks in them already.

"I'd say that depends on how drunk you are and how likely I can get both of you in bed." Jake said with a straight face.

Both women blushed. Jake didn't flinch.

"Check please!" Darlene said.

Maxie lived closest, so they went back to her place. Her husband was away camping and had taken the kids. Almost as soon as they walked in, both ladies were stripping Jake's clothes off him. They quickly took turns riding either his face or his cock. Theys shared him as best they could. Once both women had climaxed, Jake made sure to spew his milk on both their faces.

"Lick it off each other," Jake commanded.

They gleefully did so, then took turns cleaning his rod free of any lasting cream.

"I don't want to hear anything about this at work. I'm serious." He said without a hint of joking.

Once he stepped out, he knew Monday word would spread like the flu. He smiled knowing it with certainty.

**********

But that didn't help him with his Sissy problem.

Luckily he had an idea. After work, he drove home slowly in his complex looking for her. When She spotted him she started walking towards his place in a circuitous route. Once he was inside his place, he heard her knock. He opened the door and she sauntered in, looking as slutty as ever.

She had on tiny jean shorts that showed off some of her cheeks. Her top was tiny and tight, her nipples hard and poking at the fabric. She was leaning into him, looking up. He sucked in her tongue as she groped his thickening man muscle.

"Let's go for a ride," he said.

"Yaz! Fuck me like you always do daddy!" she started to kneel, her lips parting in anticipation.

Jake stepped back, "I'm taking you somewhere," he clarified.

They both got into his truck and he drove them 20 minutes away to a black colored nondescript building. Jake opened the door for her, and she walked to see walls covered in lingerie and sex toys.

"Pick some outfits that will make me fuck you like a good little whore that you are," he said before kissing her.

Sissy walked slowly looking at the merchandise, then looking back at Jake. She looked like she was going to cum right there and then.

She chose a bondage outfit, leather straps that would circle her body in a quasi-outfit, and hooks and eyelets to bind her. She also chose a tight fitting short 'dress' that was almost a fishnet except it had a lacey theme. It was white, then she saw a little fake bridal gown.

"Ohmygawd! I can be your little slut wife!" she hopped and clapped.

When they got back to Jake's they quickly got to fucking, Jake treating her like a rag doll. He had her climb on top, reverse cowgirl, but then had her lay back. Her back was on his chest as he pumped her up and down on his rock hard meat. One hand grabbed her nipples and groped her pubescent little tities. His lips kissing her neck from below. The other started groping her tiny dick.

"My clitty doesn't deserve your hands," Sissy said.

"What did you call it?" Jake wondered aloud.

"My clitty; as a femboy, I don't like my 'thing'. I should be a girl so I can be your cumslut all my life. I live to be fucked like a sex doll and serve my daddy's wishes." Sissy explained

Jake started fucking her harder and harder, jack hammering her from behind. The way she spoke made his dick harder. He moved her so his cock could wail on her ass. He now had her laying her back near the edge of the bed. He lifted her ankles and towards her shoulders. Slamming into her now, sissy's ass was wide open for all his abuse. Her hands held her clitty back so it didn't interfere with her daddy's pleasure.

Jake started cumming into her shitbox at the same time her clitty started spitting little splatters of cum. Jake rubbed his hands all over her clitty, wiping up her small donation. Palming his hand on her face, Jake made her lick her cream. Sissy eagerly licked his hands and fingers clean.

"I want to eat your ass Daddy! Can I please rim your beautiful manly shitter?" she begged.

Like before, Jake wasn't sure what she was asking. Sissy got up on her knees, letting Jake's cum ooze onto her hand and also licked it clean. Jake watched amused. When sissy finished, she got up and gently moved Jake to the bed.

"Kneel on the edge daddy," she asked.

Jake did so, and then felt Sissy nudging his back to get on all fours. Once he did, he felt Sissy kneeling behind him...

...and a wet warm tongue started moving around his sphincter. It darted around and her lips massaged his butthole.

"Holy shit!" Exclaimed Jake. He leaned forward crossing his arm and resting his face above a pillow. He felt Sissy spreading his cheeks apart as she kept orally massaging his anus.

"Gawd damn, that feels good!"

Sissy started stroking his meat as she dined on his anal flesh, it was getting harder and sissy wanted to swallow it some more. Sissy had Jake so wound up with her analingus, he face fucked her for her effort. Sissy's make up ran as his abuse of her slutmouth brought happy tears to her eyes.

God she loved her Daddy.

**********

A week later, Jake took Friday off, and went back to the sex store. He was alone, and as he entered it was the same lady as before.

"Can I help you?" She asked.

"I was here before, and wanted to take some pictures. Is that okay?"

"As long as you don't use them to make money, be my guest."

Jake used his phone to snap pictures of some contraptions from several angles. He saw something that caught his eye, he glanced at the girl and she gave him a knowing smile. He purchased his find, all the while she gave him 'fuck me' eyes. As he was leaving, he gave her a smile. She smiled back, "Don't be a stranger, come back any time!"

From there, Jake went to Home Depot and started buying lumber and jointers. Once home he started doing what he did best; building things. Using his assorted power tools, he referenced the pictures and got going. Once he was done, he looked them over and smiled with pride at his work.

He went upstairs and moved stuff around in the spare bedroom. Then he had the task of moving his crafty work up to the room. He then measured the beams in the ceiling and tested to see which were load bearing. Once he knew which ones, he drilled into them and installed 'eye screws'. Using some leftover chain, he installed his find. He gazed upon his work and smiled.

Once he was done, he took a shower and made himself a burger and heated up some fries in the broiler. Nothing like hearty food after getting work done.

**********

"Hey! Bring that hoist over to the westside, we're going to need it!" Jake spoke into his walkie talkie.

The large truck lifted its support struts and then slowly moved over. As the crew went about their business Jake walked over to the water cooler, some guys milling about. As he approached, some of the guys had lecherous smiles.

"What?" Jake knew where this was going.

"Nothing man," one of them said, unable to stop smiling.

He looked around, most of them looked away. "What?"

"How was Darlene?" someone said behind him.

He spun around, no one made eye contact.

"She was amazing," he copped to it, "she was really pent up and let me have it, I destroyed her pussy!"

A huge collective guffaw let loose.

"But you didn't hear anything from me!" He smiled, and walked away.

**********

Jake got home...it had been a long hard day. He kicked his boots off and took a long hot shower. Once he was done, he got dressed in his basketball shorts with a tank top. Wandering over to the couch, he put on Netflix and started catching up on one of the shows he had been binge watching. Before long he fell asleep, snoring filled the living room.

There was knocking on the door, it sounded urgent.

He got up bleary eyed, and opened the front door. It was Sissy.

He didn't notice she was in an extremely emotional state. Her red puffy eyes testament to her crying her eyes out, her chest still heaving from her labored breathing.

"C'mon in, I'll fuck you good once I'm fully awake," he muttered.

"Jake! I need your help...my mom kicked me out of the house," she sobbed. "She found out I stole some of her hormone replacement pills..., I have nowhere to stay!" she started bawling all over again.

Jake sobered up quickly, took in her disheveled appearance and everything she had said started to register. He was silent, his mind was doing some internal algebra, and solving for X.

"I'm sorry, but you can't stay in my spare bedroom," he said sadly.

Sissy sobbed even more, her body shaking with her distraught emotions. Her life had been annihilated in a single evening.

"Follow me, I have to show you something," Jake said as they walked down the hallway.

Jake opened the door and stepped aside, "It's got a bunch of crap in there."

Sissy stepped into the doorway and looked. The room was empty, except for a pillory, a rack, and a swing chained to the ceiling. Jake had created a BDSM dungeon.

Sissy was shocked into silence, her mind ripped from her current predicament.

"You're gonna have to share my bed I guess!"

Sissy turned to him, her jaw dropped open. Jake leaned in and kissed her, reaching for her bottom and squeezing it hard.

"Your ass is going to be raped on a regular basis from now on" he whispered into her hot breath.

Sissy was speechless, if she had a cunny it would be wet. Instead her sphincter started twitching of its own volition. Then a light bulb turned on in her head.

"I have just the thing!"

She ran to the front door, and grabbed the backpack she had left on the step. She tossed it inside, then went around the corner from the front door, and got the two wheeled suitcases and dragged them inside. She rifled through them to find what she was looking for. When she found them, she rolled them up to her chest and ran to the bathroom.

"Give me a minute!" she said as she passed Jake. Jake smiled, knowing he had made her day. His cock stiffened knowing he was about to give a class A deep dicking.

"Go in the spare bedroom and close your eyes," she begged.

"Alright, will do."

He sauntered in and faced the door with his eyes closed. He heard her heels on the floor as she walked in. "You can open your eyes now Daddy!"

She was standing there in a white mini-skirt dress, but it was a lacy fishnet type. It was sleeveless, but she was wearing white silk gloves that reached past her elbows. Her red thong clearly visible under the lingerie-dress. Her hair was quickly styled and was capped off with her faux bridal veil.

A marriage made in debauchery and fuckery.

He took her then and there, yanking her panties off, but leaving everything else on. Hoisting her up, he placed her on the swing. It came with stirrups and hand holds which Sissy quickly intuited and got herself in position. The seat held her bottom and carried a majority of her weight easily. Jake dropped his shorts, and lubed his cock monster with a coconut oil based lube.

The swing changed everything.

Her backside was Jake's sex toy as he pushed into her hard and fast. Fucking her like a rag doll as the swing allowed him a harder and faster thrusting than previously possible. Sissy was beside herself, her legs started spasming uncontrollably within minutes as she had the start of her analgasms.

"Fuck me like it's our wedding night Daddy! Claim me as your cumslut whore... please swear you'll never stop fucking me like your sex slave...!"

Jake kept it up, pounding her boipussy with reckless abandon. As Sissy had her body used, he reached forward and started choking her with both hands. He used this grip to slam her onto his engorged phallus. Over and over he slammed her towards him. As he squirted his man's milk into her bussy, he released her throat.

The sudden rush of air made Sissy's asshole explode with pleasure. Her make up was ruined from the tears, looking just like a two dollar whore, which Jake found incredibly erotic. Her clitty dumped cum onto her stomach. Jake leaned over her and licked her cum into his mouth and then dumped it into her waiting mouth. His hand massaged her clitty as it shrunk.

Jake had her clean the cum off the floor with her mouth and tongue. His cock getting hard again as he watched her do so.

"Well, if you're staying with me, I guess that makes you my girl," Jake smiled.

He hugged Sissy into his hairy chest as she shook with relief. Her sobs were filled with joy as she realized he had made an honest woman of her, albeit a slutty whore of a woman.