Jake's Surprise

Wednesday, when Jake took his lunch from wiring the new office spaces they were building, he didn't expect to return to the rest of the day off. He drove back to the site, and saw his crew sitting around.

"What's going on?" he asked one, his arm leaning out from the rolled down window.

"Supervisor told us to stop work, some shit with the permits." he shrugged.

"Fuck!" he muttered, and drove his truck to the trailer instead. As he got out, he saw his supervisor walking out of the trailer. He saw Jake and raised his hand, not in a wave, but in a 'stop' kinda way.

"Before you get started, let me explain. When the developer added two more office spaces, they didn't think to apply for the new permits. Trust me, someone over there is getting their ass chewed out. We should be back to work on Monday. They are going to try to expedite it through the city, seeing as it's an addition and not a whole new development."

"What about my crew? They're out of pay for two days minimum, and what if we aren't back on Monday? I mean I still get paid as a foreman, but I know what it's like losing a few days' pay."

"We are planning on spreading them out at other job sites, for the time being. But you Jake, you can cool your heels and relax. Look at it as a surprise four day weekend. I was just heading over there to tell them the news."

"I'll give you a lift then," Jake said.

They drove 30 yards to where the crew was standing around and Mike, their supervisor, explained everything. He asked Jake to get them in a batch of threes, and then gave each trio their new site for the next few days.

"I know it's crappy to drive out to your temporary sites, but at least you'll be getting paid. You'll be working under the foreman at those new sites. Cross your fingers and I'll see you guys back here on Monday." Jake smiled, to encourage his men, not because he was happy about it.

Jake got in his truck and drove home. As he got close to his condo, he remembered a few years back coming home early and catching is wife fucking a neighbor. He had almost beat him senseless, but had remained calm enough to get pictures and as they quickly tried to get dressed. The divorce had been ugly, but he had come out ahead due to her infidelity. He shook his head and cleared his mind. Fuck it, shit happens he thought. Good thing they hadn't had kids yet, or he would've been paying alimony and child support.

As he entered his community, he slowed down even though kids were in school. As he turned into the path that took him past several garage doors to his end, he saw a teenage girl walking in the same direction. She was wearing a mid-thigh skirt, and white stockings. Her shirt was tied up with a scrunchy, showing off her exposed midriff. As he passed, he glanced at her. She was thin, blond and had tiny tits. Just before he looked ahead, he saw her pulling a lollipop out of her mouth.

That gave him dirty thoughts.

He hit the remote just after passing her, and rolled to a stop to wait for the garage to open. She caught up...as he glanced at her again, she used the lollipop in a very suggestive way.

"You're kinda young to be dressed like that, aren't you?" Jake said.

"I'm 18, and very legal." she said, still sucking the lollipop suggestively.

"Yeah, well I like my women a little more full bodied and more grown up."

"Your dick won't know the difference if I suck it."

Jake just looked at her. He had heard some 'kids these days' stories from his coworkers, but this was too much.

"Well let's put that to the test, let's see what you got?"

He pulled into the garage, and she followed him in. Getting out of the truck, he opened the connecting door to the kitchen. She followed him in. Jake was in the living room just past the kitchen, he unbuckled and unzipped and dropped them. His meat was only slightly aroused, since she wasn't really his type.

"Sit down, close your eyes," she said.

He leaned back to the couch and sat back. The leather felt cold on his ass cheeks, but he didn't mind. He closed his eyes and felt and heard her getting on her knees. Her hand took his meat and raised it, then he felt her tongue licking his balls, and sucking them into her mouth. His cock started getting stiffer. She rolled his testes around her mouth, her tongue massaging them for several minutes. Then her lips started kissing all around his jewels, kissing and sucking at his flesh, all the while her hand gently stroked in thickening cock. He was getting pretty stiff, and she hadn't ever started blowing him yet. He peaked, and saw she had her eyes closed and her other hand was under her skirt.

Jake smiled, closed his eyes and just enjoyed it.

Her mouth was doing magical things to him. Her tongue was sliding up the underside of his johnson, then down. She did this several times before she started rubbing it around her face.

"I love your cock, it's as big as my face!"

Then he felt her taking him in, her mouth so warm and wet. She toyed with the mushroom, her lips cradled it, rubbed it before inserting it deeper. Her lips massaged his shaft, her tongue trying to wrap around it. All the while her hand still stroked it.

Now she started taking him as deep as she could. She thrust her face down on him, fucking his tool with her slut mouth. On and on, her mouth worked his pole.

"Fuck my face," her tiny voice said. "Fuck it hard! Please!"

Jake looked at her, her eyes begging him. Jake took his construction worker's hands, and started shoving her down on him. At this point, her mouth was a pussy for him to bang. He stood up, and started ratcheting her face on him.

"Gak gak gak gak gakgakgakgak."

Then he blew his load.

Sticky rope sprung out and dove right down her throat. She swallowed load after load. Jake let his dick keep spitting, the twitching muscles sending orgasmic shock waves up his spine.

"Holy shit girl, that is the best blowjob I've ever had!"

She looked up at him, wiping her lips with her tongue, smiling a slutty smile. Her tiny pubescent tits were open, and her pink nipples aroused.

"I try my best. Can I call you 'daddy' then?"

Jake chuckled a little, "Sure, whatever makes you happy. Just promise you come around and blow me like that again."

They composed themselves and he walked her out. He grabbed her ass as he opened the front door. "Well, you know where I live. I got the next couple days off. Swing by if you want more."

She smiled, "Don't tempt me, daddy! And call me Sissy. I'll be your sissy as long as you want." She walked away with a bounce to her step and skipped around the corner.

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

Sissy collapsed on her bed and smiled a deep smile. Her fantasy was no longer a fantasy. She had done what she had dreamed about doing all through high school. Next time, she wanted to take off his shirt, hopefully it was nice and hairy. And a construction worker too! She couldn't wait to feel his rough hands all over her.

She started pinching her nipples, then her hand reached for the night stand. In the little drawer she got her sex toy. A six inch dildo.

She was going to fuck herself with his cock and cum in her mind.

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

The following day, Jake got up and started getting ready for work...then he stopped. He crawled back into bed and fell asleep. When he did wake up, it was just after 9am. He did his morning ritual, and then made himself a hearty breakfast, instead of the quickie he usually ran out of the house with. Once he was done, he relaxed and turned on the TV. He cued up the DVR, and round the recent UFC fight he had missed, and started watching it.

Maybe a few days off wasn't so bad, he thought.

After watching several fights, he headed over to the gym and hit the weights. By the time he was done, he picked up lunch and headed home. He left the food on the kitchen counter and took a shower. With a bath towel still wrapped around his hips, he got his lunch and sat down to eat. But before he began, he opened up the sliding glass door and front door, allowing a gentle breeze to waft in. Yeah, he liked days off.

"Knock, knock" Sissy said from the other side of the screen door. Jake had a mouthful of food that he was chewing.

Jake looked over, and thought, why not? To Sissy's enjoyment, he did have a hairy chest. He had trimmed it a week or so back, and his half grown chest hair was hairy enough, but still had a trimmed look. He smiled, got up and went to the screen door, opening it.

"Nice of you to come back." as he swallowed the food in his mouth. "I've been thinking about that blowjob." he smiled lasciviously.

She tugged at the towel, it came off. His cock was already aroused, and he stood there on his front step nude, dick out in the fresh air. She dropped and started sucking it right then and there.

"Okay, let's get inside before a neighbor walks by," he said, taking her inside.

He walked her to his bedroom. He noticed she was wearing pink and white thigh high stockings. This time she was wearing tiny booty shorts, and a simple bralette, also pink. Her hair was in ponytails. The final touch, a pink leather collar with "cock slut" in gold handwriting script.

She rearranged his pillows so he could recline against the headboard. Then she patted where she wanted him to sit. He did so, his rigid cock ready for a nice mouth massage. He sat back, relaxed on his pillow, his legs opened wide, his member pointing to the ceiling. She crawled onto the bed, and placed herself between his legs. Her face was soon wrapped around his rod. Jake closed his eyes and let himself go, enjoying her feminine wiles. Her arms were draped over his thighs as she bobbed up and down, greasing his pole with her saliva.

Jake moaned, then placed his hand on the back of her head. He didn't shove her down on it this time, he just enjoyed having it there. Part way through, she rose up, stringy saliva coated her lips.

"I'm going to fuck you now," she said, her eyes glazed with lust.

She kicked off her shoes, and pulled off her tiny shorts, she sat on him reverse cowgirl, pulling her tiny panties aside. Her anus parted easily enough, and she took several thrusts to ease her way down on him. His hands came around and played with her mosquito bites. She was right, his calloused hands were rough, and her nipples loved it! He wasn't even pinching them yet, but they hardened into little baby toes.

She started rising and falling on his shaft. Her hands used his strong arms as support as she drove herself up and down on him. He helped lift her and drop her on his hammer. She felt tighter than any pussy he had in recent memory. Their bodies were clapping with the rhythmic cadence they fell into. Her legs spasmed with her first orgasm, but she didn't stop her pace. On and on, she rocked against his body. Her body craved more, her body wanted his cream to fill her.

"Gawd, oh gaad..." she moaned, "yes, I love it daddy. I want more!"

Jake couldn't take it anymore, the feeling too sweet, too tight for him to hold onto it any longer. He pinched her nipples as he filled her purgatory with his heavy cream. She leaned forward and twerked her ass on him several times, milking all his cream into her.

"Oh My Gawd!!! That was so good! Thank you, I love my gift daddy!" She played her role.

Jake squeezed her tiny ass, then spanked it several times. His devilish smile was relaxed and contented. She climbed off him, and her panties popped right back into place. She sighed a deeply contented sigh, and slowly got her things. Naked, he walked her to his front door. In the door frame, he pulled her in and kissed her, shoving his tongue in her mouth. His right hand cupped her tiny breast, then went down and reached between her legs.

He felt a tiny knob.

There was no cleft, there was a small bump.

She stepped back. His eyes were wide open in shock. She gave him a sad look, she had got so caught up in her reckless lust, she hadn't avoided his discovery.

She quickly walked away, hoping he wouldn't turn violent.

He stood there, nude, at a loss for words or even thoughts. Her tiny body rounded the corner in no time. After several moments, he stepped back inside and closed the door. A creeping sensation washed over him as he realized 'she' was transgender. His stomach tensed. His mind reeled. He went and showered again. Trying to wash her off of him.

Then, unbidden, a thought flashed across his mind. Her ass had been so tight.

N0!

He wouldn't go down that path! He got dressed and decided he needed to get his mind right. In a large mason jar by his bed was an assortment of coins and small bills. He grabbed the money and drove himself to the nearest strip club. He spent the next several hours stuffing dollar bills into big titted women. He got several lap dances before he left as well. He even managed to get the phone number from a stripper. She moonlighted as an escort and stripping was a good way to screen men.

When he got home, he made himself a steak dinner, complete with roasted corn on the cob and mashed potatoes. Eventually he called it a night and went to sleep, after changing the sheets. In the wee hours of the night, he woke up with a massive boner. His dream was slipping away, but he had no doubt about it. He had dreamed he was fucking Sissy in a bondage outfit.

He grabbed some Melatonin pills from the bathroom and dry swallowed them. He fell asleep to a dreamless oblivion after that.

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

It was now Saturday, and he woke up just before noon. Although he hadn't drunk, he felt like he was hungover. He dialed up the number of the stripper/escort and arranged to have her come over later in the day. While he spoke with her, he asked her to wear lingerie. The more lace, the better.

After spinning his wheels and keeping himself occupied for most of the day, he got text from the stripper. She was on her way. He decided to make it worth her and his while. He shaved and showered, and dressed as if he was going on a date. He quickly cleaned up his place and lit some scented candles he had got as a joke gift from coworkers. He looked around and was pleased with himself. Then the doorbell rang.

He opened the door, and there stood a blond, just below his height. She had a push bra that made her large breast clearly visible. Her sleek tight fitting dress showed off her round backside and legs as well. The outfit capped off with 'come fuck me' shoes. He held the door as she strutted into his place. She looked around and smiled, appreciating the effort on his behalf.

"Nice to visit with a gentleman. You would be surprised how gross some men are." she genuinely smiled.

"Would you like a drink?" he asked. "Red or white wine?" he offered.

"Red, merlot if you have some," she said.

He walked into the kitchen, where several bottles were on the counter. He found a merlot, and used the wine bottle opener to pop it open. He poured two drinks and handed her a glass. She took it and had a sip.

"Mmm, it's good! I taste a hint of plum and it's velvety. I think I can almost taste the oak of the barrel." she smiled. "You're a man of culture."

She leaned in and kissed him, he set his glass down and put his hand on her waist. Setting her glass down, she put her arms around his shoulder as he kissed her deeper. They made their way to his bedroom. The scented candles gave the room a vanilla aroma, and with the window partly open, the occasional breeze stirred the scent in the air.

"Excuse me while I get into something more comfortable." She said, going into his bathroom.

He partially disrobed and climbed into bed. She came out, and was wearing light blue lace lingerie. The bra and panties matched perfectly, and she had straps clipped to her thigh high matching stockings. She also had a gold chain wrapped around her waist. She posed for him, then shifted to another striking pose, she climbed into bed and crawled towards him seductively.

His boxers were tented, and his meat excited.

She slipped off his boxers and sat on his meat, her panties pressing it against his stomach. Leaning forward she french kissed him, as he groped her bra. After a few moments, she undid the clasp and the bra fell off allowing him to rub her breasts. His rough hands fondled her as they continued kissing. After sometime, she leaned over to her purse and got a condom that she placed on him with experienced ease.

She sat on him, taking his cock into her. He rolled her so he could be on top and started shoving his meat into her willing pussy. She moaned and ran your hands over his back as he pounded her pocket with his hammer. He was motivated to win back his manhood.

When he started to soften.

He thrusted into her harder, but there was no denying his equipment wasn't as rigid as before.

Unbidden, and unwelcome, Sissy's blowjob came to his mind and his dick hardened. He tried to shove that thought out of his mind, but it kept coming back. And as he played back his rape of her mouth and then her ass in his mind his cock grew even bigger and angrier.

"Oh fuck yes!" the stripper called out. "That's a good cock!"

He pounded at her, angrily since he was thinking of fucking a young boy. His cock spat his cream into the condom suddenly. He kept thrusting into her, his johnson remaining stiff. He was able to continue fucking her, while his cock was rigid, but somewhat numb. Eventually he stopped. He doubted he would come again so soon.

"Oh baby, that was a good fucking! I love it when someone treats me right..." she smiled contentedly.

"You're very welcome," he smiled at her, hiding his shame.

They pawed each other for a bit before she got ready to go. She was very loving and draped herself on him as he walked her to the door. "You have my number, call me anytime you need some relief."

He handed her $300 discreetly, then she turned and walked out.

He looked at her walking away, his mind confused with the turn of events.

As disgusted as he was with himself, he couldn't avoid the fact that thinking of Sissy made him harder. She had been a proxy for the skinny girl looking boy. His mind was having a hard time processing what was happening to him. So he went for a walk.

He walked down the hill to the gas station for no reason other than to clear his mind. When he arrived at the Chevron, he bought a lottery ticket and a Monster energy drink, just going through the motions. He started walking back to his place. As he passed the pool, he saw a thin teen boy. It was Sissy, he knew it, but she wasn't in one of her outfits. He stopped, and waited as she was walking by.

"So that's what you really look like," he said calmly.

"I'm sorry about the other day. I should have come clean from the start." Sissy said.

"But then I wouldn't have fucked you." Jake said quietly. "It's no different than what most guys do to get laid," he admitted.

They walked a few steps in silence.

"I used to get beat up by guys at school," Sissy said "I'm pretty sure it's because they hated to admit I turned them on. I finished school in a continuation high school. I think the principal did it to keep the jocks from getting kicked out, not to protect me."

Jake smiled a grim smile, reminding him of what he must have been like in high school.

"Well, if you want to come by again, I might not mind." he was surprised to hear himself say it.

"Really?" Sissy said, a sense of longing in her voice.

"Yeah, really," Jake said, knowing he was speaking the truth. "Here's my number. But let's try to keep it under the radar."

"Yes daddy," Sissy smiled, knowing what he meant.

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

It was Monday, and Jake was back at work. The crew took it in stride, they at least got paid, even if they had to drive farther than usual for a few days.

"So what didja do with your time off? One of his crew asked.

"I went to a strip club, and after a lap dance, the stripper gave me her number. So I spent the weekend fucking a blonde," he said with a wicked grin.