Testing the Girlfriend Pt. 01

Author Note: Part 1 is the background and build up of the story.

Mark had always felt like a lucky guy. He was relatively good-looking, at 5'9" with shaggy brown hair and a moderately athletic build. He was attractive and interesting enough to have a few girlfriends through high school and college. Athletic enough to keep in good hiking-on-the-weekends shape. But, for some reason, he'd landed an absolute bombshell out of college, Tiffany.

Tiffany (all of her friends called her "Tiff") and Mark had met at a bar, after Tiffany had been successfully rejecting college bro after college bro, though Mark caught her smiling after each one. He made some off-hand comment he couldn't remember, and she laughed. They chatted, she saw him the next morning getting coffee, and they realized they lived in the same building. A few weeks talking, and they were dating. Six months later, and Mark was a pretty happy dude.

How, Mark couldn't understand. She was 23 and a year out of college; he was 26 and working a job at a car dealership. She made most of her money as a waitress, but was also doing quite well posting thirst traps on Tiktok. And Mark could see why. She was blonde (not naturally), tan, 5'4", and gorgeous; relatively small waist, with a flat influencer-girl stomach, but DD tits and a nice ass that stayed impossibly round in a thong. Maybe part of her attraction to him, Mark thought, was due to the fact that she definitely fit the "dumb blonde stereotype." Not an idiot, but she was spacey and clueless at times. And had a robust sex drive--Mark thought her pussy walls were probably all cum at this point, although she wasn't big on cumshots or swallowing, and Mark had never broached the idea of anal.

Tiffany liked to show off. Maybe it was the influencer side, but Tiffany absolutely loved being the center of attention. The last steakhouse they went to, the waiter had to ask Tiffany to cover up; her red dress was painted on, and apparently not well enough, as while she leaned over to eat her mashed potatoes she apparently flashed every businessman at the bar. When they went out for drinks, she wore a skirt that could only be described as "a belt", and Mark caught more than one guy staring at her bare ass. Tiffany didn't like wearing much underwear, and was usually in a thong or g-string. At the beach, she found every reason possible to tan topless. Especially when the bros were out playing beach volleyball nearby.

Mark was a lucky guy.

All of this attention made him feel a bit strange; he felt constantly nervous that Tiffany would cheat. She could get any guy she wanted. He knew she wouldn't; and yet, the thought kept bugging him. It was even more confusing that he got a hard-on every time he thought about it. A few times, he had weird dreams where Tiffany would come back home after a night out alone, and she'd smell...different.

Lucky for him, he thought, he saw an ad for a sex therapist doing free first consults. Maybe a therapist, someone who dealt with sex all day, would be able to help him work through this. Why did the thought of his girlfriend going out alone? He went ahead and decided to give the therapist, Jessica, a call.

The call that changed his life.

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He probably should have been suspicious of Jessica's qualifications on the first Zoom. She was 24 and very cute. And wearing a way-too-tight white tee-shirt with no bra. And with clear nipple piercings. She looked like she was trying out for a sex worker ad, but sure enough, she started talking with him about his sex life. After a few intro questions, and a bit of what Mark swore was flirting, she broached the subject of Mark's concern.

"What do you think about Tiffany? Do you trust her?"

Mark paused. "Yes, I think so. I mean, I don't have a reason not to. She's never done anything. But, I don't know, I feel like she would. Maybe? I don't know. She's kind of stupid. And really hot."

Jessica laughed. "Slow down! Don't worry. This is a common concern. What do you want to learn about her?"

"I don't know. I want to know what she'll do. I almost don't care, I just want her to be mine! Although," he took a breath, "I do get, you know, excited when thinking about it. Which is crazy!"

Jessica paused. "Well, Mark, what do you think about when you think of her cheating?" Jessica's hand seemed to slide from the mouse on video downward, and her arm moved towards the middle of the screen, but Mark didn't notice.

"I mean, it does turn me on. Oh no, does that make me weird?"

"Tell me what thinking of her cheating does, specifically. What do you do? Do you touch yourself?"

Jessica's arm moved a bit, pressed against the side of her bra-less breast and squeezing it towards the other. Her nipple became even more pronounced, and Mark caught a little bit of a catch in her voice at the end. Strange, he thought.

"Yeah, I mean, I'll be honest, I've thought about her cheating. And I've jacked off to it. But I don't think I'd ever want it!"

Jessica's tits heaved for a second after Mark said "jacked off", straining against the shirt. Mark saw a little sweat build up on her forehead, and heard a faint buzzing over the speakers. "Man, she must be taking this seriously if she's sweating" Mark thought.

"Mark, tell me about touching yourself. How big is it? And do you stroke it hard or slow? How tight do you grip it?...for therapy, of course!" Jessica said, her voice raising in pitch a bit.

"Well, I mean, probably 6" and pretty thick I guess. I grab it pretty tight, put some lube on there, and stroke it slowly until I'm ready to bust. Then I bust in a napkin and call it good." Strange therapy session.

Jessica visibly convulsed, leaning forward, her tits swaying. "Oh God, that's helpful Mark" she managed to say after a few seconds. She looked directly at the camera and smiled. "I have an idea for you."

"Why don't you let her...try and cheat? And watch to see what happens. Set her up with a friend you both know, but not too close. And make sure he's attractive. Better yet, find a house party that a bunch of your attractive friends are at and send her there. Tell your friend what's up, and ask him to hit on her. Ask him to keep you informed of what's going on, so you don't feel disconnected. And see what happens!"

Mark thought. "I mean, sure, I guess I could try that. It's making me hard thinking about it, so it can't be bad, right?"

Jessica smiled slyly. "Sure, Mark, I'm sure it's going to go great for...one of you!" And she hung up.

"Well, that was weird" thought Mark.

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Mark was watching football with some of his old college buddies over the weekend. He didn't really know these guys super well other than James, who he and Tiffany both knew from the football team. James wasn't much of a success after college, but for some reason he'd hung out with Tiffany (she swore they'd never hooked up) and Mark had watched the team on the weekends. He was a big guy, about 6'2", with a muscular build and a group of equally attractive friends. Jessica's suggestion popped into Mark's head. "Am I really going to do this?" he thought? Fuck it.

"James, I've got a question for you" he said out of earshot of the others.

"Shoot, man. What do you need?"

"Well, you know Tiffany obviously. I'm kind of worried she might want to cheat on me, and I was hoping you could, I dunno, hit on her for me? I want to see what happens."

James' eyebrows went up. "I mean, sure man, but most girls say yes to me. I can hit on your girl, but how far?"

Mark took a breath. "Well, I mean, I need to know if she'd cheat or if she's just flirting. So I guess as far as it takes. But keep me in the loop! I want to know everything that's happening!" Mark grabbed some chips and munched, before followed up with "I'm sure it's fine, she's not actually going to do it."

A pause. James thought about it. "I mean, OK man" he said, and grinned.

Something about the grin felt...off to Mark. "I'll test her, see if she's willing to cheat. And I'll keep you up to date on EVERYTHING that happens." He put a big emphasis on the "everything."

"Uh oh, what am I doing, I should just call this off" thought Mark. But a tingle in his nuts made him work up a smile for James. "Thanks man."

"No problem. Hey, I'm having a party at my friend's house this Saturday. It's a pretty nice place. You can bring here there and we can do...the test there!"

"Sure, man, I'll swing by." Mark knew that Tiffany would certainly be ready for a party.

James' grin broke into a full-out smile. "Awesome, see her then!"

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"Oh, Mark, we're going to James' house tonight? I love those guys!" said Tiffany, sitting across the couch from Mark. It was 4pm on Saturday and Mark was getting ready for the evening.

"Yeah, some fancy house party? I'm not sure. Either way, we should dress up and be ready for a good time." Mark knew that the words "dress up" would trigger slutty-Tiffany-mode.

"Aww, OK, I'm happy to look good for those guys. They're all super cute." She smiled and stared off out the window. "What should I wear?"

"I dunno, babe, pick something fun and surprise me. We'll head over around 7."

"OK!" Tiffany bounced away to her closet. "I'll start looking now! Will there be other girls there?"

Mark thought out loud "Yeah, probably. He didn't say, but it will be him and his guys for sure. I'm sure they'll bring some other girls!"

"Ooh, OK, got it!" said Tiffany. "I'm going to blow those sluts out of the water!"

A few hours later, she came out ready to go. "Let's go Mark! This is going to be so fun!"

Mark had to pick his jaw off of the floor. She normally slutted it up, but this was something else. Black heels with red bottoms, knee-high sheer black stockings with lace on the top, then a whole lot of bare leg with what looked like...the bottoms of garter belt fasteners sticking out of a black pleated skirt? Generous with the "skirt" definition. it was a 4" piece of cloth that didn't even try and hide the bottom of her ass cheeks.

As she walked, just the air moving past ruffled it enough so Mark could see she was wearing bright pink panties. She spun ("well, that just removes all mystery" thought Mark) and he saw that it was in fact a thong, not panties. Moving upward, her flat stomach was exposed below a sheer lacy red top that cupped her tits beautifully, pushing them up and holding them at attention. The top was basically a bra with enough lace underneath to make it pass as a top. Her soft natural mounds jiggled enticingly as she walked: Mark wanted to shove his face in them then and there. She had on a full face of makeup, with dark black mascara, bright red lipstick, and her hair down in flowing blond curls.

She looked ready to fuck.

"Wow, you look nice" was all Mark could say.

"Thanks, babe! I can't let those other girls out-dress me!" She smiled. Mark thought to himself that she probably wasn't dressing up for the girls. She did love attention, after all.

"OK, let's go."

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As Mark pulled up to the house, he engaged the plan. Tiffany sure wasn't going to pass on a party, especially when she was right outside; Mark didn't have to stay for this, he could just come up with some excuse to leave her with James. It wouldn't be a fair test if he were influencing the outcome.

"Baby, I'm so sorry, I just found out I have to finish something up at work! But don't worry, you look so nice. You should still go to the party! I'll drop you off here and pick you up later, just give me a call."

Tiffany frowned, then smiled. "Aww, OK! I really wanted to hang out with you, but I'm sure James and his friends throw a great party. Thank you!" And she leaned over and gave him a kiss and hopped out of the car.

Mark watched her walk away and up the steps, the thin pink strip of her thong up her ass becoming more visible with every step she took. "Well, here it goes" he thought. James came to the door, gave Tiffany a hug, waved to Mark, and Tiffany walked in.

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Well, Mark was something, thought James. He understood where he was coming from, but damn, Mark had to see what Tiffany was. A huge slut. More importantly, a huge dumb slut. She clearly liked Mark, and James had no doubt that she wasn't actually planning on cheating on him. But if he put the moves on, well, he wasn't so sure she'd resist. Oh well, Mark's loss. James pulled his phone out and started streaming video of Tiffany walking to the bar. "Oh my god" thought James, "this girl was perfect."

It was going to be a fun night, and just like Mark asked, he was going to let him know EVERYTHING that happened. He texted the link to the site to Mark so he could keep informed. The site would let multiple people stream video to one place, so Mark and his friends could all make sure Tiffany was staying true to her man. Or something.

The house party itself was popping off. James had his 4 good friends here, who were all aware of the challenge; in addition, he'd invited about 30 other guys and girls he knew. The house was gorgeous, a big mansion his buddy's dad owned. They had a DJ in the corner, solid lighting and smoke, and a great dance floor with a bunch of couches around. The bar area had some tables and chairs, and the vibe was a great EDM house party. Everyone was dressed to kill. Tiffany definitely took the slut award, but the other girls were all in various states of attire--from standard cocktail dresses to borderline Playboy bunny. Just the place to impress someone like like Tiffany.

She chatted up some girls at the bar and grabbed a very fruity drink from the bartender James had working that night. After a few minutes, James walked up behind her and tapped her on her bare shoulder. "Hey girl! You're looking beautiful tonight. Like the party?"

Tiffany looked around and with huge eyes. "Yeah, it's amazing! I didn't know you lived in a house like this! Must be expensive!"

James definitely did NOT own, or live in, this house. Or anything remotely as impressive. Well, what she doesn't know won't hurt her. "Yeah, I'm doing pretty well. Large house, large pool out back, large everything baby!"

Tiffany laughed, looked up and down at James. Yup, she's into me, he thought. "Awesome, I didn't know you were doing this well! And the music is so nice!"

James smiled. "Grab a drink! And why don't you come dance with me? It's only fair that you reward the man of the house with a dance!"

"I mean, as long as Mark won't mind. I think he'd be OK with it."

"You're too beautiful not to dance. Plus, I think you'll like me as a partner."

"OK, James, then I'm yours!"

Oh, you have no idea, he thought.

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After a few dances, and a few drinks, Tiffany was loosening up. She had started facing James (not bad at all, he thought; her tits swayed up at him and, on a few songs, almost jumped out of her top), but now she'd turned around and was grinding. James had told his friends to join them and give her some attention; while the rest of the dance floor was pretty full, Tiffany had 5 guys all around her complementing her.

"Oh, your hair looks so nice!" one guy said. "Your hair is so sexy tonight girl!"

She took each compliment, beaming.

"Aw, thanks!"

They danced for 30 minutes or so, girls and guys coming in and out of their circle, James attached at the hip to Tiffany the whole time. As the music died down between songs, James decided to act. "It's time" he said to the other guys in on the plan; they would know to start up live streams to Mark at their discretion. He grabbed his phone and started his POV stream immediately; it would notify Mark automatically.

"Listen, Tiffany, you're the most beautiful girl here. You deserve an awesome guy." James grabbed her hips and pulled her towards him with his left hand, his right pointing his phone at them from the side. His cock was rock hard at this point, and he was certain she could feel it. And it wasn't small: his 9 inches of dick was jammed squarely into her ass cheek.

"Oh, James...You're so...nice" Tiffany murmured. The music started again, and she spoke up. "Mark is a great guy. If I wasn't with him...but I am!" He heard the hitch in her voice. Definitely doubt. Would she stop him? Would she hold out for Mark and end this right now?

She continued to dance.

James smiled into the camera before aiming it at Tiffany's ass. He pulled up her skirt (meaning, slid it 2 inches upward) so her ass was fully exposed in the thong. There it was, a little strip of pink the only definitive piece of cloth keeping her "not naked."

She groaned. Her eyes closed. Another guy aimed his phone at her front, capturing her reaction for her boyfriend on the other end.

James spoke up so that Mark would definitely hear. "He won't know anything, and plus, don't you want me? We'll keep this our own little secret." Ironic, as she was in the middle of 5 guys gawking at her almost-naked body.

"Oh, I want you" she sighed. "But I really shouldn't!"

"Oh, come on, let's just have a little fun. I'm rich, this is my house, and you're on my dance floor looking like a sexy little slut." At the word slut, James felt her shudder. "You owe me this!"

She didn't say anything, but kept grinding. Her right hand came up to her breast, seemingly subconsciously. "Success" thought James. "We are going to DESTROY this girl tonight!"

He undid his belt buckle and slid his pants down. His cock popped out, immediately crushed against her bare ass. A little gasp escaped her red lips.

"Oh, James, is that..." she shuddered again. "Oh, your dick is...big." Subconsciously she scooted backward, feeling his length with her skin. Her ass was smooth and firm, sliding over his thickness.

James tossed his phone to a friend who kept it going. He slid his hand upward from her waist, first under, then cupping her left breast; her right hand still held her other. He pulled her close, grinding his dick into her until it slid between her ass cheeks and against her panties.

She moaned this time. "Oh, fuck, that's good."

"I know, sweetheart. Let's have some fun tonight."

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After a few more songs, James had fully dropped his pants. His friends surrounded him in a circle, hiding them from the rest of the house, although James was pretty confident, they'd find out soon enough. Throughout the songs he and Tiffany went through what were essentially Tantra poses: dick-to-ass, pussy-to-dick, standing doggy style (it took James everything he had not to fuck her right there), and finally James spun her around. One tit had just started popping out of her top, and he could see just the top of her areola. Her eyes were starting to glaze over from all the attention.

James took a step back, hands on her shoulders. She kept moving with the music, looking down at his erect cock then back up into his eyes. Her lips parted slightly, seemingly of their own will. He looked down at her; her black stilhettos moving on the floor, her uncovered gap from the stockings at her knees up to her pelvis, skirt hiked up to below her bare belly button. Her tight stomach sloped up to the red top holding up her beautiful, full tits, one about to expose itself to him. Her red lips parted, her hair running down in blond curls, and her eyes. Her eyes staring at him, inviting him to ask for more.

The music pounded. "Tiffany, why don't you keep dancing, but on your knees."

She paused, her waist and tits standing still for a moment. She looked at James, seeming to pause, then smiled. "Yes, James" she said. The way she said it, his dick grew another half an inch.

"I've got to, uh, text a buddy. Don't mind me" he said as he took his phone from the friend and held it, clearly pointing at her. She didn't seem to notice. God, she was dumb.