The Bet

By Anonymous1234

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Tags: cheating, girlfriend, oral, voyeur, webcam

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Shy girlfriend finally gives into sharing fantasy at a college party
The Bet

Chapter One

It all started with a bet. It was no secret between Stacy and I about my little kink. We had talked about it in the past, especially in bed after a long, hard session. No matter how much I tried I kept coming back to the same fantasy; I wanted to watch. I know I know it's weird, I'm even a title weirded out by it, but there is no denying how much it turns me on and how much it turns her on...

Stacy is gorgeous. Young, hot, nice tits and the best ass on the planet. Despite all this she was shy and nervous about showing it off. Oh I know she had a wild streak, she had it before we got together, but now, four years later my sweet, innocent, little, girlfriend was a bit of an introvert. Yet whenever I talked about sharing her, watching her, and having a stranger take her like a dirty slut her tight pussy would soak the bed and I'd end up with claw marks down my back. So I knew I had to do something and I naturally started pushing her towards it.

After months of trying I had pretty much given up; for although the sex had never been better it didn't seem like she was going to budge. Then one night while we were getting ice cream she brought up a party she was going to with her best friend for the next weekend. When I asked Stacy the theme she turned bright red and said,

"Well it's called Anything for a Buck. They hand everyone one dollar of Monopoly money and you trade it for anything you want like shots, or dances..."

"Or sex?" I practically yelled

" Well yea people trade for sex too, but you know I won't do that, I mean it's not like anyone would want that from me..." She said with a sly, little grin.

With that little comment I of course knew she wanted to play our usual game so I pushed her some more.

"Ha. Okay babe, what are you going to wear then?"

"I was actually going to match with Jessie, she is wearing a like secretary type outfit, everyone is going in costumes" she quickly replied giving me the impression she had thought about this quite a bit.

"So what does that entail? Short skirt, white button shirt, and heels?" I responded, " like when we role play sexy CEO haha?"

"Yes. Just like that. I was thinking that black lace bra and fishnets too..." She said looking away from me.

Now I was starting to get excited. I couldn't believe she was thinking like this. If she was going to dress like that maybe she was finally ready to try out our fantasy for real.

She looked at me now, biting her lower lip, silently looking for approval, searching my carefully neutral face for some sort of reaction.

Quickly I replied, " Well if you're going out like that then you better wear the outfit right. Keep the shirt undone enough to see your bra and wear that matching black, lace, g string. "

Stacy flashed me a grin and said "Oh yea, don't worry I was already thinking that. Plus that bright, red, lipstick that you like. "

I liked it when she wore it because her lips looked amazing when they were wrapped around my cock and she knew it. And now I knew what she was thinking. She was deliberately doing this to look sexy, slutty even, but how far was she going to go? Well she gave it away with her next comment...

"But anyway it doesn't matter because no guy would want me even dressed up like a hot, secretary haha" she said with a fake sad face.

"Ha! Want to bet! I will bet you anything you could get any guy you wanted to fuck you until you couldn't walk. And that's before you are done up. You would barely make it into the house before someone would offer to bend you over. " I shouted with a laugh.

"Fine. What's the bet then?" She quickly retorted.

"Okay you seriously want to bet? Fine. I bet that you could walk into that party and pick any guy you wanted and get him to fuck you. " I said, "and if I'm right you've got to blow me for an hour and if I'm wrong ill buy you a day at the spa."

Stacy, now visibly flushed, parted her lips, looked me dead in the eye and said,

“Deal. Friday night then.”

Chapter Two

By the time we got home that night she was so worked up she practically ripped off my clothes. I pushed her down and pulled off her tight jeans while she pulled off her shirt uncovering her perfectly shaped tits in a bright green bra. Her panties matched, I love when she does that. I clawed off her thong and buried my face in her waiting pussy, running my tongue up her slit.

She started bucking her hips as I flicked my tongue across her clit and ran it up her slit. I slowly stuck a finger in her pussy sending a spasm of pleasure through her body as I hit her spot. While I thrust my fingers into her wet cunt I furiously sucked on her clit. She grabbed the back of my head forcing my tongue deeper moving her hips with such force I knew she was close. Just as her movements reached their peak she screamed and clenched her legs around my head. Her sweet cum splashed across my chin and mouth as I continued to lick her to keep her on her high.

Finally she said, “ No more! No more, I can’t take it, I need you in me now.”

I needed no further encouragement. I took my rock hard member and slammed it into her waiting pussy. I grabbed her arms and pinned them over her head while I grabbed her left breast with my other hand. As she squirmed against me I thrust myself in hard, stretching her tight, hole. I started driving deeper and harder into her so that skin slapping and moans were echoing through the apartment.

“You like it rough don’t you babe. You know this is what is going to happen to you on Friday night” I said, as I started moving faster, feeling the familiar sign of orgasm. “This is how you’re going to get fucked as a dirty, party girl.”

I quickly flipped her on to her stomach and pressed my self into her again. Now I had the perfect view of her amazing ass as it bounced in time with my cock. Running my hands up and down her smooth back I could feel her tighten as she came close to cumming for a second time. She arched her back to, letting me penetrate further into her.

“He’s going to bend you over just like this and rail you until you can’t move.”

At those words I felt Stacy tense up and release all over my dick cumming more than she ever had before. She turned her head and looked back at me with utter lust in her eyes and it was then that I knew there was no turning back. She wanted it.

Stacy pushed herself up onto all fours, thrusting her ass back towards me begging me to fuck her harder.

“Come on fuck me! Use me like a dirty little slut. Fuck your slutty party girl! I want your cum all over me!” She breathlessly said through clenched teeth.

My tempo increased to a fever pace as countless dirty images flooded my mind. In a grunt I pulled out. Right on cue she flipped around and grabbed my bursting cock and directed it all over her tits and stomach. My cum splattered her body dripping down towards her still wet pussy. I rolled off her and fell across the bed with a sigh of utter exhaustion.

“Wow, I can’t wait until Friday night.” I whispered between heavy breaths.

“Ha,” Stacy snorted,” You may win the bet, but I’m the one who will get my brains fucked out.”

Chapter Three

As Friday night rolled around I sat at the office scrambling to get some last minute work done. Leave it to the boss to give me a big project on the night I finally get to carry out my fantasy. Just as I am packing my things up I get a text from Stacy.

“So lover, what’s the deal? Do you actually want to do this bet? It is okay if you don’t want to. “

Instantly I reply.

“Yes. No getting out of it now. “

She quickly responds,

“So what are the rules then? What’s the actual bet?”

“The rules are simple. I am proving that you could fuck any guy you want. All you have to do is find a guy you want and then seduce him in whichever way your feminine wiles desire. No matter what you decide to do, you must ask him if he wants to fuck you. If he says yes then I win the bet and get my blowjob. If he says no then you win and get your spa day.”

Almost as soon as I send my text I get Stacy’s

“Okay. Deal. ;)”

With that I knew the night would be interesting.

An hour later I arrived to the apartment just as Stacy and her friend Jessie were leaving and let me tell you, wow…. They were both dressed like the twin secretaries on one of those movies where most of the dialogue is moans and grunts. Stacy had told me what she was wearing before, but words don’t do justice seeing it in person. She had managed to close just a single button on her shirt letting her lacy, black bra show up top, and her sexy stomach down below. Her tight skirt barely covered her underwear, coming just a few inched down her thighs. The fishnet tights she was wearing ran all the way from her fuck-me heels to under her skirt. She topped the whole ensemble off with one of my bright, red ties, done up sloppily around her neck; it matched her lipstick. She oozed sex appeal.

They both looked at me and could tell from my expression they looked good. Stacy wrapped her hands around my neck and pushed her lips to mine, slipping her tongue into my mouth. She pulled herself in with a very sexual, very primal growl and bit my lower lip. Moving to the side of my head she kissed my neck.

Brushing her lips ever so lightly against my ear she whispered,

“Well good luck, I hope you win”

With that she released me and sauntered over towards her car.

“Love you baby, I will get back late, don’t wait up.”

Jessie turned to get in the drivers side and shot me a wink; the kind given the coconspirators in some sort of plot. Well I guess Stacy has a wing girl for the night.

Like I said, I knew it would be interesting.

Chapter Four

The night seemed like it dragged on for hours. Every time I looked at the clock it seemed to be at best, standing still, and at worst moving backwards. I would glance at my phone every few moments waiting for something, anything; I needed to know. I was so horny I couldn’t concentrate on TV and although I craved a release, I knew I had to wait for some sign. Around 12:30 I was starting to get tired and it looked like I wouldn’t be hearing from Stacy any time soon. Just as I was getting into bed, my phone vibrates with a text.

In my rush to grab it off the table I knock it down and pull the lamp off with it. God damnit, that really pissed me off, but in hindsight it was probably more sexual frustration than anything. It was a text from Stacy.

“Hey babe, how’s your night going?”

I could practically hear the shit-eating grin on her face as she said that. I quickly replied,

“How do you think? Tired, horny, nervous, horny, and also a little more horny.”

“Haha, oh I’m sorry babyyy. Want me to make it up to you?” Stacy said. “Switch on your computer and look at your email.”

With a grumble that was part frustration, part aggravation, and part not wanting to get out of bed I moved over to my laptop and opened my email. In it was an invite to a webchat. Now my curiosity started to grow, what was she doing?

I clicked on the webcam and onto the screen popped Stacy.

“Hey baby! I’m so glad to see you. I have been having the best time. Me and my new friend Mike have been hanging out all night.” She said with a wink and a grin.

I could tell Stacy had had a few drinks by the way she was talking very fast and loud. She always would get super wet when she was like that.

“Oh yea babe, where is this Mike fellow?” I stated sternly, trying to keep a smile from creeping into my face.

“Well let me tell you what I have been doing all night silly.” Stacy replied, “First we got here and they gave us both five monopoly dollars to use however we wanted. So of course, I spent all but one on drinks. But you were right, I wasn’t even halfway through my first beer before this guy saunters over to me and asks to exchange a dollar for a dance. He was cute so I said yes and followed him out into the middle of the floor. We started up pretty fast, but he was a pretty terrible dancer, couldn’t keep his rhythm and the whole time he was trying to grind his dick into me.”

My own dick twitched at that comment as I tried to contain my own excitement.

“Anyways after that song his friend cuts in and offers to show me how someone actually dances. I looked up at him. He had dark hair, was a little shorter than you, and had some muscle. I liked him so I said yes. We started moving to the beat and I found myself grinding my hips into him. One of the dirty dancing songs came on and he twirled me around so my ass was right up against his crotch and we started really going at it on the dance floor. He moved perfectly and with each passing sway, he would push into me. By now all I was thinking about was our bet so I decided to play along and push my ass back into him.”

Now I was really turned on. Here was my sweet, introvert of a girlfriend telling me how she was grinding her ass into some stranger’s crotch on the middle of a dance floor.

“Then a slow song came on and he started dancing with me back towards a darker corner of the room where it was much harder to see what was going on. I spun around and pushed my chest into his as his hand drifted down and grabbed my ass. At this point I could feel his hardon through his pants and my pussy was practically on fire. As we danced he slowly pushed his hands lower and was playing with the end of my skirt. Suddenly his hands slipped under my skirt and grabbed m, ass. God it felt so good and so wrong to have another man’s hands on my ass for the first time in years.”

By now I could see her skirt was a little rumpled and just talking about this was turning her on even more.

“He slowly ran his right hand around my thigh until he was just inches below my pussy. There was no way he couldn’t tell I was soaking wet and he could definitely feel the heat coming off my pussy, I wanted him and he knew it. He started walking his fingers up my thigh until he was just a hair away from actually touching it. At this point it was like I was in a trance, but I knew I had to do something, so I told him that I don’t even know his name and he would have to wait for that. He introduced himself as Mike and we really hit it off.”

I groaned with displeasure. Why would she have stopped him? She is just being a tease.

“ Well anyways we laughed and flirted a little ways, but I was so nervous I had to get some air. So me and him walked back to the bar area got a few drinks and then went and sat outside. Even though I was super nervous I knew I might have a shot at this, and I wanted to prove you wrong. Dancing is one thing, sex is something different.”

I snorted causing her to arch an eyebrow.

“We found a bench a little ways away from the party off in the dark and started nursing our drinks. Suddenly, Mike turned to me and handed me one of those silly dollars. He wanted to trade it for a kiss. Just as I turned to say something to him he grabbed me and pulled me into him on the bench. He pressed his lips to mine and I let out an involuntary moan. I couldn’t get enough of him and grabbed the back of his head and pressed my body into his. It was so hot, I melted into his arms. I felt him reach between my legs and slowly work his way up to my thong. It was happening so fast and I couldn’t do anything to stop it.”

Now she had my attention and my dick was fully erect just thinking about her making out with this guy she barely knew.

“Just as I put my tongue into his mouth he pressed his fingers to my panty-covered slit and it sent a jolt up my body and my pussy soaked itself all over again. He knew I wanted him and with a quick twist slipped his fingers in through the fishnets and underneath my panties. I arched my hips to give him better access and he pushed his fingers right into my sopping wet pussy making me moan louder than ever before. He starts thrusting his fingers in and out of my little cunt, tickling the clit and flicking my spot, I am telling you they were like magic. He started going faster and harder grabbing my tits under my bra with his other hand and then, suddenly I was cumming all over his hand. Then just as I came down from my high I heard a giggle and saw another couple watching us from the driveway and knew we had been caught. So we quickly fixed ourselves and went back inside, but now my panties were covered in my cum and there was no way people weren’t going to notice” Stacy said, reliving the moment.

I was so excited, at some point in her story I had came and I didn’t even realize.

“Oh Stacy, baby, that is so fucking hot, see I told you that you could do it. I guess I win the bet.” I stated triumphantly.

“Not so fast lover boy, the bet was to get a guy to fuck me, getting fingered on a bench in the backyard does not count as fucking.” Stacy said with a grin. “And that’s what brings me to why I web cammed you. I figured, as long as you’re quiet you could watch.”

‘Watch what babe?” I stammered hesitantly.

“Well baby, I told Mike to go get us some drinks and then meet me up here in 15 minutes. I asked him to come fuck me.”

Oh boy. Definitely an interesting night.

Chapter Five

Before I could even get in a word of protest Stacy pushed the computer away and hid the webcam where her new lover wouldn’t see. I could hardly contain my excitement as I watched my sexy, and now apparently slutty, girlfriend saunter over to the mirror and adjust her outfit. She fixed her hair, straightened her skirt, and flicked off her heels. Just as she had finished reapplying her makeup there was a knock on the door.

Stacy practically ran over to the other side of the room where I couldn’t see and opened the door. I heard some voices, one obviously Stacy, the other must have been Mike.

“So you’re more of a slut than I thought you were. You didn’t tell me you had a boyfriend?” Mike said with a fake disproving tone.

“Ha, what my boyfriend doesn’t know won’t hurt him. Besides he said I could cut loose tonight and have fun. You are fun so why not?” Stacy said, dripping with sex appeal.

“When he said cut loose, I don’t think he meant fuck some guy you barely know.” Mike said with a jest.

“Oh, well if you want you can call him and ask permission to use me?”

“Ha, fuck that, he’d say no and then I would be shit out of luck. I think I’ll take me chances with him not knowing.”

With that Stacy let out a little squeal as Mike picked her up and threw her on the bed. Now they had crossed in front of the camera and I could see everything. I instantly clicked record and stared intently at the screen. He pressed himself on top of her with what was obviously urgent need and they started making out. I saw Stacy’s hands reach up and unbutton his shirt until his bare chest was hanging over her. She then reached down and started stroking the large bulge in the front of his pants, her hand slowly sliding up and down getting him harder.

Mike then slipped his hand into Stacy’s shirt and grabbed onto her right breast. He played with her nipple until even I could see it through the webcam, sticking straight up begging to be sucked on. Suddenly he stopped and stood straight up. With a growl he reached down and ripped off her shirt flinging buttons all across the room. Stacy let out a gasp, part surprise and part pleasure as she laid there with her shirt ripped off and her bra showing.

Mike grabbed her shoulders and slid her off the bed so that she was on her knees in front of him, eye level with the ever-growing bulge in his pants. Stacy reached up and pulled off his belt, throwing it across the room in a sexual fury. She needed that dick, now. I could see her hands shaking just so slightly and she couldn’t undo his pants. Mike reached over and helped her with the button and quickly she reached up and tugged them down.

In an instant she jerked off his boxers letting his cock spring free. Stacy let out a small gasp at its size. It was perhaps the same length as mine but very, very, thick around. Her small hands could barely grip it all the way. This new cock entranced her and for a second I thought she wasn’t going to do anything.

At that instant Mike reached down and unclasped her bra letting her perfect tits hang free. Then he slowly directed her towards his waiting member, twitching in anticipation.

“Oh I don’t know Mike, I don’t think I can fit that all in my mouth, that is such a big cock.” Stacy said nervously.

“Well if you’re going to be a slut and cheat then you better act like a slut. And what do they do?” Mike said with a grin.

And without another word Stacy’s little mouth engulfed the head of the cock. Her red lips stretched to accommodate his impressive girth and for a quick second she flashed her eyes at the camera, knowing this is what I have always wanted.

She placed one of her little hands at the base and worked her mouth over the head licking and sucking. With her free hand she grabbed his ass and pulled him closer then slid it down and started fondling his sack making him gasp in pleasure. Stacy really started getting into it now, maybe because it was so big, maybe because it was a stranger, or maybe because she knew I was watching. Knowing her, it was likely a combination of the three.

Her head started bobbing faster up and down his length. She started jerking her hand up and down his shaft as she continued to work as much of his head into her mouth as she could. She started to slide her other hand from his sack back farther until she obviously reached his asshole. Mike let out a groan of pleasure as she tickled him there while simultaneously jerking him into her mouth. Then she flipped his dick up towards his stomach and ran her tongue down the length to his balls. Taking each one in her mouth gently she flicked her tongue back and forth while rubbing her hand on the tip of his cock giving him spasms of pure pleasure.

Suddenly Mike growled, “Enough. I can’t take any more of this. Get up I want your pussy.”

He grabbed her under her arms and lifted her onto the bed. Stacy’s eyes went wide with excitement and she knew what was coming next. Before she could react he pushed her skirt up from her waist and then ripped a hole right in her fishnets giving him direct access to her waiting cunt. With a tug he pulled aside her g-string and pressed himself into her.

Stacy arched her back and let out a long moan as she felt her first new cock enter her in years. Mike reached over and grabbed her tits with one hand and then used his other to grab her waist and pull himself in deeper. He started rhythmically thrusting into her, slowly working his way deeper, letting her get use to his size. Abruptly he thrust his full length into her making her cry out and her whole body shake. I knew that look, she had just cum all over his hard cock before they had barely begun.

Mike started going faster, slamming his dick in and out of her soaking wet pussy, making her moan with every pump. He placed both his hands on her waist and started pounding her little cunt for all he had. Stacy wrapped her legs around his back and pulled him into her, wanting as much as she could get from him. She reached her arms around him and grabbed onto his back urging him on with her moans and bucking hips.

Now their pace became fervent, as they both got closer to orgasm. In a cry of pure pleasure Stacy closed her eyes and came all over this stranger for the second time that night. Her heat must’ve sent Mike over the edge as I saw him tense up then slam his cock as deep as it could go.

Stacy’s eyes went wide as he pumped his cum into her then her expression changed to one of lust, loving the feeling of another man’s cum deep in her pussy. Mike slid his cock from her, covered in a mix of his and her cum. As he pulled himself away I could see the mix of their juices spill out onto the bed, staining her fishnets and underwear. Stacy led out a deep breath and tried to calm her breathing, basking in the post-orgasm glow.

Panting Mike looked at her and said, “Sorry, I should have asked first I just couldn’t stop you were so wet and tight.”

Stacy looked up at him with glazed eyes, “It is fine I’m on the pill, I love it when a guy cums in me.”

She glanced down at her pussy, still wearing her lacy g-string and fishnet tights. They were covered in cum and torn where Mike had forced his way into her. She reached down and stuck a finger into her dripping cunt, feeling how wet she was. Stacy shuddered with a surge of nerves as she realized what she had just done. She had actually fucked another guy, and while I was watching to boot.

“Well I guess I really am a little whore now.” Stacy said to the room with a laugh.

Stacy started to rise from the bed and gather her things when Mike glanced over to her,

“Where do you think you’re going?” Mike said to her with a dark look “I am not done with you yet.”

She looked up at him and saw his cock slowly harden again. Mike stalked over towards her still splayed out on the bed. When he got to her he stood her up then slid down her body kissing her neck and working his way to her breasts. He placed one of her nipples in his mouth while he fondled the other with his hands. At the same time Stacy reached out and grabbed his still wet dick, stroking him, getting him hard again. He ran his hands down her body until he reached her tights and in one tug pulled them down to the ground.

I sat there mesmerized by what I was watching on the computer. No only had I watched her fuck him once, and cum inside her, it looks like she was about to do it again. I didn’t think my own dick could take any more, but I stiffened once again as I watched Mike slide off Stacy’s g-string and toss it across the room. Stacy unzipped her skirt and tossed it aside as quickly as she could so that she was now naked in front of him.

Suddenly he reached to her hips and spun her around so that she had her hands on the bed and her ass towards him. She flipped her hair over and looked over her shoulder, shooting a glance towards the hidden camera and wink for me. She stuck her ass into the air and arched her back giving him easy access. Mike took the cue and pushed himself into her waiting pussy.

Grabbing her hips he slammed himself into her, there was no need to warm-up, and it showed because he fucked her as hard as he could. The room filled with Stacy’s moans and slapping skin as his balls slapped against her pussy. Stacy’s tits were bouncing in time with her ass as her slutty, wet, pussy got fucked from behind.

Mike slid himself in and out of her faster and faster their breathing getting heavier, their cries more urgent. Stacy reached around and rubbed her clit, her pussy growing wetter with each passing thrust. Arching her back, Stacy buried her face in the bed while he grabbed her ass and pounded her as hard as he could. The entire bed was rocking back and forth and both of them were covered in a sheen of sweat.

Then Mike pushed her down until she was flat on her stomach, and her ass in the air. She tensed up and I saw her once again cum for him, soaking his cock and giving him a renewed vigor to stroke into her harder. Stacy must have sensed he was close, so she pulled his cock out and twisted around onto her back. In a grunt Mike’s face twisted and he started to cum. Stacy carefully aimed his cock and splashed his cum all over her chest and stomach.

He collapsed onto the bed, his now softening cock still slick with Stacy’s juices. They both laid there panting on the bed with those grins you can only get when you’ve done something bad that was too fun not to do. Mike rose from the bed and started collecting his clothes, stopping to grab Stacy’s still-damp panties, laying on the floor.

“I am taking these are a souvenir. But I am not letting you go tonight. What time do you have to be home?” Mike said as he put on his shirt.

Stacy still lay there on the bed covered in cum and out of breath.

“I don’t have any time to be back.” She replied quietly.

“Well I live just a street away, after the party why don’t you come back with me and you can have more of that.”

“Okay, I’ll see.”

With a wink Mike gathered his things and left the room leaving Stacy to gather herself. She started picking up her ripped clothes to try to get some semblance of order, and then she turned towards the camera and me.

“Well, well, I guess you won the bet sweetie.” She said to me with a sexy voice.

I couldn’t help but notice how good she looked. She had cum all over her tits, and I could see it leaking out from between her legs. There was no way she could walk back through the party without people noticing how thoroughly she had just been fucked. I wanted her so bad I almost couldn’t control myself; I wanted to drive straight to that party and fuck her for the rest of the night.

“I think I’m going to go stay at Mike’s place, I mean I don’t want to drink and drive after all. I will see you in the morning babe. “ She said, and quickly turned off the webcam.

A few minutes later I got a text,

“Good night, you know I love you”

Wow. I am glad I let her go to that party.

Chapter Six

Stacy came home the next day wearing someone’s white tee shirt and a pair of running shorts. As soon as she came in the door she threw her arms around me and kissed me deeply. She smelled like sweat, alcohol, and sex and I immediately felt myself start to stiffen.

“I missed you baby. I love you. Are you mad at me?” She said as she looked up at my eyes.

“Oh of course not babe, that was a dream come true thank you so much.” I said quickly, “So what did you do the rest of the night?”

“Oh well I stayed and drank some more. Jessie ended up going home with a guy she has been sleeping with and Mike had offered me his place. So I went an stayed at his overnight.” She said while looking away from me.

“Oh yea? And what did you and him do?” I laughed.

“Well what do you think?” She laughed back at me, “I went back to his place and he fucked me twice more then we fell asleep and he then he fucked me again before I left”

I felt myself grow hard hearing her say it. I reached my hands into her shorts and felt her pussy, still wet with their mix of cum. With a wink she starts walking towards the bedroom stripping off her shirt as she went.

“Come on lover, come fuck me harder than him,” She said as she looked over her shoulder at me, “If you can.”

Yeah. I am definitely happy that she went to that party.