Chatting with Chrissy
- 4 years ago
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First Date Bets With Chrissy free porn video
The best way to describe Chrissy physically was "cute face with a hot body". She had as pretty a smile as I'd ever seen, and bright blue eyes. Her hair was straight, brown and about armpit length. From her photos, she still looked fit with a nice flat stomach, and perky round boobs. A 32C if you forced me to guess. Moreover, whether she wore jeans or a bikini, she couldn't hide her big curvy ass (probably a 36) that stood just above her long shapely legs. I had already jerked off multiple times to a photo of hers on the app where she was posing on her knees in a bikini at the beach. I wondered how many others had done the same.
I got to the brewery five minutes early and grabbed an outside bench table for us in the corner. On this hot Sunday afternoon I was wearing jeans with a tight black T-shirt to subtly show off my fit body. I'm 29, 6'3" and regularly workout and play soccer to keep myself in shape.
About 10 minutes after I got there, I saw Chrissy walking towards my table. She was wearing a white sleeveless button down blouse and tight black shorts that ended at her mid thighs. Her long legs had no other coverage downwards for miles until you reached her feet where she was wearing low-top sneakers. She was turning a head or two in her direction due to her legs out on display, and her shapely round ass pressing hard against her tight shorts. I knew she was cute from her photos. In real life though, she was STUNNING! "Hiiii", she smiled as she extended her arms out for a hug. I pulled her in for a big hug and could feel her boobs pressing against my chest. Her body smelled of Jasmine. "You look stunning", I said. "Thanks, you're not bad yourself", she giggled and blushed. As she sat down opposite to me, I noticed I could see the outline of a black bra through her thin white top. What wouldn't I give to get my hands underneath....
We ordered a couple beers and our conversation was easy, organic, and fun. Two rounds in, and we were getting pretty flirty. She was playfully punching my arm whenever I made fun of her. And I would find excuses to touch her arms and forearms. I caught her staring at my arms and chest on multiple occasions, and I sure was guilty of staring at her breasts numerous times. I didn't know if it was deliberate or she just needed a stretch, but at one point she raised her arms overhead and stretched her torso out for a good 5 seconds, sighing deeply. Her sleeveless top rode up to her upper belly, exposing her flat stomach and belly button. I saw she had perfectly shaved, white, silky smooth armpits. As her breasts pushed to the front of her top from her stretch, they showcased her voluptous torso beautifully. I was already aware that she was well endowed in the curve department, but internally felt like a kid in a candy store admiring her torso.
As we continued to talk, she mentioned she liked sports, hiking, coffee, wine, and light beers. She still hooped, not fazed at being the only girl in her neighborhood's pickup basketball games. While she lacked some strength and speed to the boys, she played hard with sheer determination, unafraid to play physical and dirty if she needed to. I learnt that she was very competitive about nearly everything, and came up with a plan to use that to my advantage.
"Bet I can chug my glass of beer faster than you", I casually teased, after I returned with our third rounds from the bar.
"Oh you're on. Prepare to lose, mister". Exactly what I wanted.
"What do I get when I win this bet, Chrissy?".
"It doesn't matter, coz you won't. But when I win, I want you to pick up the entire tab for the evening". She gave me a competitive smile that I found cute rather than threatening.
"Oh Chrissy, I would have offered to do that anyway. But fine, you got it. And we still haven't decided what happens when YOU lose".
"Aargh... fine. I've seen you staring at my boobs since I got here. So if you win, which you won't, I will unbutton my top 3 buttons so you can have an easier look at my cleavage".
I couldn't believe she was so proud and confident to make this bet.
"What? I don't think I've been ogling that much? I mean... you're sexy!". She blushed and giggled as I said that.
"I was kidding about you ogling. Ok only half kidding actually. I've seen you look in that direction a few times. Honestly, I find it quite flattering .... since I clearly find you attractive as well". She was smiling and blushing even more now.
After a pause of few seconds, she said "So what do you think about the conditions?"
"Deal, you're on!", I replied.
We counted down and began chugging our beers and while Chrissy was an above average beer drinker, I finished my glass a good 5 seconds before her.
"Grrr... get that stupid grin off your face".
"I will. As soon as you unbutton your top".
"Fine", she pouted and unbuttoned the top 3 buttons down to just below her breasts.
A new world had opened up to me. I could see so much of her cleavage now. Tops of her big, round milky white breasts visible almost down to their centers where a thin, black lace bra was annoyingly in the way. Her bra was straining hard trying to contain those mounds.
"Are you happy?", when I had been staring for a good ten seconds.
"Yup, couldn't be better. Sexy bra by the way. Thanks for dressing so provocatively for me."
"You're welcome", she pouted sarcastically. There was a look of vulnerability on her face and she was turning more pink by the second. Maybe it was the heat, or her embarrassment, but droplets of sweat were starting to appear on her forehead, chest and armpits. And wait a second... are those her nipples poking through her bra? Is she turned on by this embarrassment?
I wondered how much more I could push my luck with her today.
"You know...", I said thoughtfully after a few more minutes of casual talk, "if you were seeking revenge, I'm willing to go again, and we can do something to even the odds a little bit in your favor".
"You bet your ass I want revenge. What do you mean by evening the odds?"
"Well... how about we let you pick which beers you and I will be chugging this time as long as they are still both pint sized. And you can have a headstart. Say 3 seconds?"
"That works for me. What are we betting on this time?"
"That depends on how big of a revenge you're seeking, Chrissie".
After deliberating for a minute, Chrissy loosely lashed out, "If I win, you have to wait on me for the rest of the evening. Not just that, but I own you for the rest of the evening, for me to do whatever I want with you. Needless to say you will pay for the bill for our evening here."
"Wow, that's a lot. You sure are in the mood for some revenge".
"That's the deal. Are you scared?", she taunted.
"Nope not at all. But in return, if you lose again, then you're the one paying the entire bill. And similarly, I am the one owning you for the rest of the evening. Are you game?"
She seemed a bit nervous at it and contemplated the risk versus reward as she bit her lower lip. Eventually her pride made the decision for her.
"Deal", she said at last. YES! My fantasies were about to come true.
"Why don't you go to the bar and get us our beers? And remember, you don't get to button your top up".
She scowled at me and slowly got up, but sure enough she returned a few minutes later with 2 glasses of beer. There was a knowing smile on the bartender's face who had served her, no doubt
very pleased with the view he had been treated to.
"Here's your beer", she slid a pint glass of a dark stout towards me and kept an easy-drinking lager for herself. This would be tough. But if I won, the rewards were infinite.
"Ready?" she said, as she started chugging.
Three seconds later I started chugging and was attempting to catch up with her. I was drinking faster than her, but she still had a lead. Second by second I was catching up though, and by a quarter glass left, I had caught up with her. Chrissy saw me catch up to her, and her eyes widened as she took in the possibility that she might lose this. In a last ditch effort to win, she tilted her glass a little too much and the remaining beer spilled all over her front. Added to her misery was the fact that I had finished my glass without a spill.
"Oh my God, oh noooo!", she shuddered as she took in the implications. In addition to her pride being crushed, her top was half open, and she had beer all down her body from her chin to her belly. All of this in public at an outdoor brewery. And now she was owned by me for the evening.
"It looks like I win again. I understand if you're feeling uncomfortable with the situation and want to back out of our bet agreements", I said.
"No! I made the agreements knowing the possibility for defeat existed. And I am not one to back down now. I will honor the bet", she replied proudly.
"Are you sure about that?"
"I am. I have been in many difficult and embarrasing positions before. At work and in sports. Even when I thought my teams would likely go on to lose the game, I have never given up. And I'm not starting now". By now her eyes were starting to tear up. I gave her a minute to get them in control.
"Ok, in that case, I want you to remove your bra. Hand it over to me. Then go back to the bar, and get us two more stouts." Knowing she didn't like the dark beers, this was another subtle step of asserting dominance on her. To show Chrissy that she was no longer in control of her situation now that she had agreed to go through with it.
Slowly, hanging her head in shame, Chrissy reached behind her back, removed her bra, and handed it to me under the table. I ran my hands on the bra, feeling the warmth inside the cups where her breasts were resting, and some cold dampness on the outside where beer had made its way.
"May I please put these 3 buttons back on?"
"No, you may not. Although I will be nice to you, and not make you unbutton any more. For now. Plus, I don't think the buttons will help you at this stage".
It was true. With the beer spillage, major chunks of her thin white top had become see through. And with her bra gone, nothing was left to the imagination about Chrissy's big white jugs. Of course, it didn't help that Chrissy's nipples were hard and practically poking through her top. I stood up to get a downblouse view and had a clear look at those pink nipples of hers, standing proudly on Chrissy's large circular light-brown areolas. God was I feeling lucky right now....
As she made her way to the bar, three different bartenders saw her and rushed to the front of the counter to take her order. They took their sweet time to fulfil her order, making sure all three got plenty of treat for their eyes. Chrissy could feel three pairs of X-rays on her but felt powerless to do anything in that moment. She tried mentally to ride out the storm, and oscillated between staring at the wall and closing her eyes. She couldn't bring herself to meet the gawking gaze of the bartenders. After about 5 minutes, they finally served her. They gave her an extra beer for free, partly as a thanks for the eye candy for future fap sessions. But also knowing it would make it difficult for her to quickly walk back to our table with three glasses, giving them longer to stare at her behind.
When Chrissy was returning with the three glasses, she was the epitome of a slutty, sexy barmaid who works for her tips. With her rack on display, her long legs and that cheeky booty underneath those black mini-shorts, she turned more than a few heads. She tried desperately to hold the three beer glasses close to her chest to hide what she could, but it wasn't much help. Her breasts were big, her bra-less half-open top was see through, and there was always something that was visible to the patrons as she slowly tiptoed back to our table. Chrissy knew it was futile to try and cover up, but she did her best anyway. She was a classy, graceful professional in her circles, but she realized that she looked like a frat house slut in her current predicament.
"Nice of you to return with an extra beer", I remarked as Chrissy finally reached our table.
"The bartenders threw that in for free".
"Perfect, I want you to go ahead and chug that extra one".
She made a face but somehow managed to get through the first stout. At this point she was 5 beers down, and feeling the effects. Which was good, because "I'd be a lot more embarrassed in this scenario if I were perfectly sober", she thought to herself.
"Ok Chrissy, I am going to ask you more questions about yourself"
"What do you want to know? You already know my work, hobbies, where I'm from".
"Not those boring details, Chrissy. I want to know your private details. And remember, since I own you for the evening, you're obligated to be truthful to me".
She nodded her head slowly.
"Have you ever had a dick in your ass?", I asked.
Just when I thought she could turn no more pink, she blushed even more. "Yes", she whispered as she nodded her head slowly.
"Oh wow Chrissy. Aren't you the naughty girl. I didn't expect this when I came across your cute photos on the app. You seemed so innocent".
Chrissy said nothing but hung her head in shame.
"Have you ever been with multiple men at the same time"?
She embarrasingly nodded her head again. "Unhuh". Her big blue eyes staring into mine scared for what I was going to ask her next.
"Tell me about the first time it happened".
Her eyes opened wide in shock and she took a few deep breaths to steady herself. Finally, after a deep sigh, she began.
"It was in college. I had made a high stakes bet with Bryce, the captain of the guys' team about how many points I could score that evening in our match against our rivals. In our away game matchup, I'd scored 52 on poor Lakeview College. But the head coach of Lakeview was Bryce's uncle, and he had been given insights into stopping my game by his nephew. I was double/triple teamed and flagrantly fouled the entire game. Even though we won the game, my bruised, hurt body could only manage to score 16 points despite my best efforts, well short of the bet target of 30.
After the game was over, before I could even rest up or shower, I was asked by Bryce to follow him into the mens' dressing room where the other 4 members of the men's starting lineup were waiting for me with their phones and dicks out. Over the next many hours, the 5 guys had their way with my sweaty, tired body. I was double and triple fucked multiple times in circles, and each member got to have each of my three holes for their pleasure. They took tons of photos of me in numerous degrading positions. Thankfully, they never publicized it, to protect themselves as much as me. I was in and out of it, but I remember the session ending in a bukkake. I remember lying naked on my back on the floor in complete exhaustion, my entire body, face, hair completely sticky from all the semen. The boys just continued to humiliate me by complimenting my "sluttiness", and objectifying my body. They acted like they owned it and continued to take photos. The worst part of this entire predicament was knowing that I had willingly agreed to get into this. And while I was given the choice to back out, I agreed to every single thing that was done to me due to my pride around the bet I had made".
By now Chrissy was sobbing silently as she was sharing this humiliating, degrading incident.
"You don't have to keep going. You can stop".
"Thanks", she managed to whisper as she sniffed and continued to sob quietly. I got off my seat, sat next to her and gave her a big hug as she sobbed on my shoulders for a minute.
After she regained her composure, I said, "You know. We don't need to continue this further" and made to hand her her bra.
"No, I want to keep going. I'm not stopping now", as she pushed my hand back towards me. She continued, "Plus.... considering the conditions of the bet, you've been quite respectful to me when you could have done a lot more".
"Ok, Chrissy. We shall continue. Next question. Are you wearing panties tonight"?
"Yes, I am"
"Describe them to me".
"Umm... they're cheeky pink lace panties", she replied confidently. Having gotten the tears out of her system, she was actually feeling secure and proud despite her predicament now.
"Do you shave your pussy?"
"Yes, I'm completely shaven down there currently".
I handed her a pen I was carrying. "I want you to use this pen and your fingers and make yourself cum. Right here".
Her intially wide eyes recovered quickly from the shock, as she unbuttoned and unzipped her shorts. She slightly raised her ass and rocked her shorts gently to slide them downwards down to her sneakers, hoping to not attract any attention to herself. She was lucky that we were in the corner seats and no customers were behind her. She debated doing the same with her panties, but her fear of completely exposing her crotch took the better of her, and she decided she would just pull her panties to the side to get the pen inside her pussy. She knew she'd been turned on for quite a while since this date started, but wasn't prepared for how wet she would be down there. As she pulled her panties to the side, her fingers felt stickyness over the entirety of the region that was covering her crotch and she shuddered.
Finally managing to pull her pink panties out of the way, she inserted the pen in her pussy. It slid in easily thanks to her natural lubrication. Chrissy started to flick it in and out. First slowly, but then going deeper each time and increasing her pace. Her left hand meanwhile was on its own wavelength. She first ran her left hand through her hair, before tracing it down her neck, shoulder and settling on her left breast. She started to squeeze that breast slowly, increasing the strength gradually. She got to a point where she squeezed too hard, causing herself to cry from the pain and pleasure and moved the hand to her right breast and started to work on that breast. Her eyes were closed, and her mouth was half open. She was breathing deeply and slowly. Despite trying her hardest to be quiet, she would occasionally moan.
Chrissy seemed to have zoned out her surroundings completely and was fully engrossed in her pleasure. She either was unaware, or no longer cared, but her left nipple had escaped her top and was visible for anyone to see. Luckily for her, it seemed that I was the only one who knew of her nip slip so far. What a lovely pink puffed, erect nipple it was. After a while, she took this hand down to her clit and started rubbing it. The double whammy on her vagina and her clit had her very close to an orgasm, and she was starting to thrust her hips forward and back. Her moans were turning into audible groans and deep sighs. Her breathing was a lot slower and deeper. Soon, her hips were gyrating more and more, and her moans were becoming more frequent.
Feeling left out, I pretended to drop something, and looked underneath the table. Her pussy was sopping wet. It was indeed clean shaven, very pink, with large dark-red pussy lips. As the pen was slipping in and out of her pussy, it was making splashing sounds with how wet she was. A finger was working on her clit causing an extra shudder from her every time it pressed on the clit. She seemed to be right on the edge of her orgasm but unable to push over the edge. Perhaps due to the public nature of her activity, even though most people had left with the Sunday afternoon coming to a close.
I made my way up to my seat and reached out towards her exposed left nipple. I grabbed it and squeezed it hard between my forefinger and thumb, causing her to yelp loudly and her body to start convulsing into an orgasm. I continued to grab onto her nipple, as I saw her face tilt up towards the sky, her back arch, and her body continuing to shudder for 15 seconds, when I finally let it go. About a minute after her orgasm subsided, she opened her eyes, looked at me and smiled, continuing to breathe deeply.
"Thank you", she whispered softly.
Her face had a radiant, confident glow from her post orgasm bliss. She had a lingering smile on her face, and she took her time before she tucked her left nipple back in. Not in the least bit shocked or embarrassed by the situation anymore.
"Show me the pen", I replied.
She pulled the pen out of her pussy and handed over the pen to me, and about 8 inches of it were coated with her thick pussy juice.
"It's dirty. I want you to clean this up for me nice and good".
She took the pen and started to lick it and suck on it seductively. She swallowed all the liquid that had been present and smacked her lips.
"That's much better", I said when she handed it back to me.
"I'm ready to head out from here and enjoy your body more. Let's finish our beers and get out of here".
We chugged the last two beers (her a lot slower than me). I gave her permission to reposition her panties and shorts, before she made the last walk of shame to the bar to pay for our evening's worth of drinks. Her bra still in my hands...
The date continues in Part 2 -->
Cathalina
- 18.01.2023
- 27
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