He Tricked the Trickster

She grabbed the sides of her thong and pulled. She stretched the elastic waistband and, in turn, the material in the crotch area, causing it to slide into the crevice between her thick, white, hairless outer labia. She reached down with both hands and pulled the fabric higher into her crotch. She tugged with alternate hands causing the thong to saw across her clit.

"Ohhh," she moaned loudly and threw her head back.

Vanessa stripped off her panties and exposed her pussy. She masturbated, rubbing her clit and pushing a finger inside her vagina. Her left hand grabbed and squeezed her breasts. She moaned and her pussy gushed fluid as she rubbed harder and faster. Her breathing increased.

Strange sounds emanate from the mask. Her body spasmed and she released a guttural scream and her hands stopped moving. She closed her legs and curled up in a ball on her side.

Sienna kept filming even though her friend was still. Thirty seconds of inactivity passed before the redhead shut off the camera.

"Send it," Vanessa said as she removed the unicorn mask. Sienna didn't edit the video. She sent it out into the ether. Vanessa went into the bathroom and sat on the toilet. Her friend followed and said, "That was hot. Did you orgasm?"

"Maybe. I think so." She peed and added, "I don't know. I've never done anything like that. I've kissed boys and let two touch my breasts. No one has fingered me. Not even me. I masturbated to keep Justin interested. In the beginning, it was all for show, I did stuff I've seen on the internet. It felt good so I did it faster. My boobs ached so I squeezed them. In the end, I felt a warm explosion spreading throughout my body. I wasn't in control. My body had these violent convulsions and I kind of blacked out."

She wiped, flushed, and got up to wash her hands. She was nude. Sienna could see her inner thighs were shiny and her vaginal lips were engorged.

The phone beeped. They read the messageSorry. I doubted you. I hope this doesn't come across as 'I expect us to have sex'. If we have sex, it'll be our decision. Maybe I'm an insensitive jackass, but I don't enjoy the dithering and angst high school girls feel about sex. It is understandable and natural, but I lived through it when I was in high school and twice more when I dated women younger than me. The 'I don't know if I should/can/know how?' is old. Is it horrible of me to say 'I want a grown-ass woman, not an immature woman-child? I want a partner who has her shit together, who doesn't create drama, and who's honest about her feelings and needs.

They shared the phone, read the message, and Vanessa quickly typedNo. You're not asking too much as long as you're a grown-ass man who has his shit together!

Seconds later they gotLet's go on a date. Are you free tonight or Sunday?

"It worked!" Sienna said triumphantly.

"Yes, but as soon as he sees me, he'll know I lied to him about who I am and how old I am."

"If only you could continue the charade. If you went on one date and he'd learn how great you are. He already thinks you're funny and beautiful. He loves your ass. If at the end of the night, you said, 'Hey. It's Vanessa' I'm sure he'd forgive the lying and understood you only did it so you could get to know each other."

"Brilliant!" Vanessa shouted. "Next Saturday is Halloween. We could go to a costume party. I'll be Sweet Cheeks. He will be Prince Charming. We'll have a wonderful night. He'll fall in love with me! And, at midnight, when I reveal my true identity, he won't care because in the hours we spent together he realized I'm smart and fun and girlfriend material. He won't care about my age."

"Yes! Lots of women marry older men."

Vanessa, still naked, typed her response.I'd love to get together. I can't this weekend. I have work and family commitments. Invite me to a Halloween party for next Saturday. I already have the costume!

It's a date. A friend is throwing one. I wasn't going to go, but now that I've met you...It starts at ten and goes late. Give me your address, and I'll pick you up.

Can I meet you there? I have to work Saturday. I'll be done in time for the party.

"That's good," Sienna said. "Having a job makes you sound older."

"And it lets me hide who I am," Vanessa said.

That works. 9733 Springfield Pike. Past the new Walmart

Great. I know that area. I'll text you on Saturday with my ETA. Goodbye

"I have a date with Justin!" Vanessa screamed. The girls hugged and jumped and shrieked. When they calmed down, Vanessa said, "Help me pick out a slutty outfit. We're going out tonight."

"Why slutty?"

"You heard him. He wants a grown-ass woman, not an inexperienced high school girl. What if we kiss and he wants more? I haven't done more. I've not touched, sucked, or fucked a dick. He'll know that I'm exactly the scared, clueless, kid that he doesn't want to deal with."

"How do you kiss and do more wearing your unicorn mask? And if you take it off, isn't the jig up?"

"Well...I'll wait until we're someplace pitch dark or ask him to play a game where we wear blindfolds or put one on him and tie him up."

"If you goFifty Shades of Grey on him on the first date that'd show you confident, experienced, that you know what you want, and aren't afraid to go for it," Sienna said.

"Exactly the message I want to send."

"So why do you need a slutty outfit?"

"Because I've never had sex. I can't fake my way through a blowjob from reading Cosmo and watching porn. We're going out to find some dudes and suck dick."

"Do I have to?"

"Come with me? Yes. I need someone to watch out for me. You don't have to give blowjobs. I just thought since you're as inexperienced as me, this would be a chance to fix that. We'll go to the next town over where no one knows us. Nothing beats practical, hands-on experience."

"I'll go."

The women had dinner with Vanessa's parents, hung out in her room, and got dressed to go out. Vanessa put on a tight white tee-shirt with no bra. Her nipples and areolas were easily visible. She completed her outfit by putting on a short jean skirt and a thong.

"You look like a slut!" Sienna teased. "If I'm going to be with you, I need to make some changes." She pulled off her green, sleeveless shirt, unhooked her bra, and removed it. The redhead had light pink nipples. Her breasts were bigger than her friends. She put her shirt back on and twisted from side-to-side. Her breasts wobbled and bounced.

"Damn, girl! Look at your boobs quake. You're showing a lot of sideboob in that shirt. Are you okay with that?"

"Yes. This tart is letting the girls go free tonight!"

The young women stood in front of the bathroom mirror and put on makeup with extra flair and a heavy hand. Vanessa giggled and said, "I haven't worn this much makeup since I was five and I got into my mother's lipstick, rouge, and face powder."

At ten o'clock, the young women got in the car and drove fifteen miles to another town. While Sienna drove, Vanessa used an app to find where the young people were partying. She said, "There's a big party at Timmy Swenson's house. His parents are out of town." She put the address into the phone and the cell phone spat out directions.

"So what's the plan?" Sienna asked nervously.

"I have a simple plan," Vanessa said. "To suck as many dicks as I can. I will be a cocksucking expert after tonight."

The women parked, checked their hair and makeup, adjusted their boobs, and got out of the car. As they walked to the front door, they could hear the party. They knocked, a random guy opened the door, and said, "Hey. The keg's in the kitchen." He walked away.

"I need a beer and then I'm going to work," Vanessa said. They got a cup of beer and drank it quickly. Sienna asked, "How are you going to do this?"

"Like Nike says 'Just Do It'. See that guy over there with the print shirt."

"Yes. He's kind of cute."

"I'm going over and ask him if I can suck his dick."

"What? No hello and getting to know him?"

"Nope. I'll never see him again. I'm here to practice and learn. Not to make friends," Vanessa said. She put her cup down, walked across the room, and tapped her target on the shoulder. She whispered in his ear. He looked taken aback and then nodded.

He led her upstairs to an empty bedroom, locked the door, and turned toward Vanessa. She knelt in front of him. He undid his belt and pants, she pulled his pants and underwear down, and she stared at his erect dick which was inches from his face.

She grabbed it and shoved it into her mouth thinking "Oh, my God! I just put a penis in my mouth! What now?" She did nothing.

"Aren't you going to move or do something?" he asked.

His words jolted her to action, she bobbed her head, and wondered, "Am I doing this right? God, I hope so. Should I actually suck?" She sucked, hollowing her cheeks.

He groaned. She thought, "I must be doing something right. Careful with the teeth. Keep bobbing and sucking and stroking his shaft. What else did Cosmo say? Play with his balls." She grabbed his testicles.

"Ow. Don't squeeze my balls so hard!"

"Sorry."

To herself, she added, "I fucked up! I was supposed to be gentle with his nuts." She went back to what she had been doing: tonguing his cock, sucking, and bobbing.

"This is tiring. My jaw aches," she said in her mind. "What do I do when he cums? I wonder what'll it taste like? What if I gag or puke?"

"I'm close," the guy announced. "Oh," he moaned and thrust his dick into her mouth as he came.

"Oh, shit," she thought. "Ugh! It's warm, slimy, and salty. Try to swallow. Nope. I'm not swallowing his jism." She let it ooze out of her mouth. "Shit. Bad idea. It dripped on my top." She closed her mouth and caught his spunk.

When he was done, he pulled out, sat on the edge of the bed, and said, "Thanks. What's your name." She looked around the room, saw a box of tissues on the nightstand, ran to them, and spat his sperm into a fistful of tissues. She dropped them into a trashcan, hurried out of the room, and said, "Thanks. Bye."

^^^

While Vanessa climbed the stairs with the guy in the print shirt, Sienna watched and said, "She's right. This party is a safe place to experiment. No one knows us. I should take advantage."

She scanned the room looking for the least confident dude in the room. She saw a short, young man standing alone in the corner who had acne scars on his face, a large cowlick in his hair, and would never be mistaken for an alpha male or movie star.

She walked up to him and said, "Hi, my name's Marylou." The guy looked at her with an expression of surprise on his face.

"Are you talking to me?"

"Yes. What's your name?" She smiled.

"Ernie." He gave her a goofy grin.

She engaged him in small talk. His answers were monosyllabic. She made her move, and asked, "Ernie, would you like a blowjob?"

"Really? YES!"

They went upstairs. A couple was leaving one of the bedrooms, they slipped inside. Sienna locked the door. When she turned around, Ernie's pants and underwear were around his ankles, and his hard prick was jutting away from his body.

"Looks like you're ready," Sienna said and giggled nervously. She knelt in front of him and took his penis into her mouth. She was scared and unsure of herself and instead of sucking his dick, she chewed on it. She didn't kiss or lick or stroke him. She gently gnawed on his cock.

Ernie grunted, groaned, and came in her mouth. He didn't complain. She didn't stick around to hear a critique.

As she went down the stairs, she told herself, "God that was nerve-wracking. I can't believe I broke the first rule - No Teeth. He didn't complain, although some of his groans sounded more like moans of pain than pleasure. What's up with dicks? They're weird looking. His cum didn't taste as bad as I imagined. It was like swallowing lumpy oatmeal. Hopefully, now that I've got one under my belt, I won't be so nervous, and, next time I'll do better."

^^^

Vanessa returned to the party and found Sienna. She took her cup and down the beer. "How was it?" Sienna asked.

"Scary. I didn't know what I was doing and I was afraid I'd do something wrong and he'd yell at me. I made a big mistake causing him to cry out in pain and complain that I was too rough with his balls. When he ejaculated in my mouth, I couldn't bring myself to swallow so I spit it out on some tissues and ran out of the room."

"I sucked a guy too!" Sienna said triumphantly.

"How'd you do?" Vanessa asked.

"Terrible! I didn't open my mouth wide enough. Basically, I chewed on his dick, but he orgasmed."

The women laughed. Vanessa said, "This trip out of town was a good idea. I need to practice." Sienna nodded and the women got another beer. They drank, swayed to the music, and calmed down.

Vanessa said, "I'm ready to try again. The guy in the corner has looked our way. I'll try him."

"He's scruffy looking," the redhead said. Her comment didn't deter her friend, Vanessa walked over to the young man, smiled, introduced herself, pulled him to her, and whispered, "Can I suck your dick?"

"Is this a joke? Did Eric put you up to this?"

"No. I'm serious."

"Okay. Lead the way."

He followed her upstairs. The first bedroom was locked. The second was not and they went in. They kissed. He tasted of cigarettes so she broke it off. She slid to her knees and went to work freeing his cock. She pulled his pants and boxers to his knees.

She looked at his penis. It was tiny. A nub. She leaned forward and slurped it into her mouth without using her hands. "Oh. He smells. When did he last wash? Don't puke. Don't puke," she told herself.

She worked his dick with her lips and tongue. She felt his dick grow and become firm. "Damn. His little dick is getting really long." She could no longer fit all of it in her mouth. She had room to add a hand and she stroked him.

He laughed and said, "Darling, is my length surprising you?" He grabbed her head, held it still, and fucked her face.

"Aah!" she squawked. He didn't stop or slow down. "Mmm!" she squealed in protest. It didn't change his actions. He held her head and pistoned his dick in and out of her mouth. She stopped trying to please him and shifted into survival mode. She opened her mouth wide and focused on breathing.

"Oh. Oh," he groaned. "Here it comes!" His first blast went in her mouth. She gulped it down worried that more was to follow and she might gag. The guy pulled out, stroked his cock, and painted her face with his cum.

A tear fell from Vanessa's right eye. Scruffy didn't appear to notice or maybe he didn't care. He tousled her hair, laughed, and said, "Thanks, darling. Hand me your phone and I'll take your picture."

"No! No thanks."

"Suit yourself." He got dressed, tucked his penis into his pants, and walked out, leaving Vanessa on her knees. She cried, found a tee-shirt in a hamper, cleaned her face, composed herself, and went downstairs.

She ducked into a bathroom, peed, cried some more, and thoroughly washed her hands and face. She went to find her girlfriend.

"What happened?" Sienna said immediately, noticing that her friend was in distress.

"He was rough and smelled and he shot his cum all over my face!" Sienna enveloped her friend in her arms and hugged her tightly. "We can leave."

"No. Dad always says that you learn more from bad experiences than good ones. I learned a lot from that guy. I lost control. I didn't speak up. I let him use me. That won't happen again." She marched off to select another guy.

"I should take another turn too," Sienna said. She walked off in the opposite direction and approached the first unattached, cute guy she saw. She smiled, talked to him, and got a bad vibe. He leered at her braless boobs and behaved in a creepy manner that made her skin crawl so she moved on.

When she walked into the next room, a young man smiled at her. She stopped, smiled, and said her name was Marylou. They talked. After he proved to be a normal person, she invited him upstairs.

They got on the bed and kissed. Soon she had his pants off. When she saw his penis, she said, "Wow. You're thick. I can't fit your cock into my small mouth. I can give you a handjob."

"Please try. My ex used to take the tip into her mouth and massage it with her tongue while stroking my shaft with her hand. If you take your top off and work the tip, I'll come."

Sienna took off her shirt.

"You have really nice breasts," he said politely.

"Thanks" she answered and she executed the move he suggested. "This is easy," she thought. "I don't have to open my mouth super wide, take him deep into my mouth, or worry about my teeth or gagging." She stimulated the tip and stroked his shaft until he cried out.

"Oh, fuck! I'm going to cum!"

He exploded into her mouth and moaned. She swallowed and waited for him to finish. A half-minute later, she said to herself, "Damn! Stuff is still dribbling out. How much cum is in him?"

She giggled as he groaned and said "Oh, Marylou. Oh, Marylou" over and over. His voice got softer and weaker and reminded her of a device with a dying battery.

^^^

While this was happening to Sienna, Vanessa eavesdropped on the conversation of a group of guys. The young men drank and kidded each other as they talked about girls, fishing, and football. A couple were vulgar and boastful about their success with women.

"Strike those two from the list," Vanessa said to herself. She noticed a big guy who didn't talk much, but when he did he was funny and never at the expense of another person. A tall blond guy in the group also caught her eye.

She joined the group, said hello to everyone, and she answered the expected questions: What's your name? Who are you? Are you new in town? While doing so, she smiled and gave the blond guy the eye. He asked her if she'd like a beer, she said yes, and they walked off.

"Instead of a beer, how about a blowjob?" she suggested.

"Hell, yeah."

They found a room, she found his cock, and sucked it. She thought, "Here we go...I hope I do better. Ok... Hmmm, this isn't too bad. He seems to like it. Now apply some of the things you've seen in porn and the advice you've gotten fromCosmo."

She tongued the underside of the tip of his dick and said to herself, "This is going well. No teeth have scraped him. He's moaning. That's a good sign. Ah! What the fuck! He came!"

"Mmm," she voiced her displeasure. He filled her mouth and kept ejaculating. She was forced to swallow to keep it from spilling out and getting on her clothes.

When he was finished, she released his penis and complained, "Hey. What happened to the courtesy warning?"

"Sorry, babe. When you did that thing with your tongue, I lost it." He shrugged, got dressed, and left the room. She followed moments later, stopped by the bathroom to gargle with mouthwash, and went downstairs.

"You're the talk of the party," a voice behind her said. Vanessa turned and saw Ken, the big, quiet, funny guy she'd met earlier.

"Why?"

"Words out that you and your friend are handing out blowjobs like candy at Halloween."

"Is being friendly a problem?" Vanessa asked, putting on a brave front.

"It's obvious what you're doing. You and your friend crashed an out-of-town party where no one knows you. You're practicing on strangers you never expect to see again."

Vanessa opened her mouth. She was about to lie like she'd been doing all evening, but instead said, "You're right. We're inexperienced and we don't want to embarrass ourselves with guys we want to date."

"It's a good plan and necessary because the consensus is you're not very good at giving oral sex," he said it as a statement of fact in an even tone. He wasn't berating or belittling her.

She looked up at him and said, "This is the first time my friend and I have given guys blowjobs and it's been a disaster. We tried to prepare by talking to our girlfriends, reading magazines, and watching videos, but when presented with a big, hard penis in the flesh, we get nervous, forget what we'd learned, and mess up."