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After I caught Kaylee cheating, we slowly reintroduced ourselves back into the lifestyle, with her hooking up her old fwb Chris (you can read that story on my profile). After sleeping with Chris again, Kaylee was fully down to keep hooking up with other guys. Swiping on tinder, snapchatting, sexting & exchanging photos with random dudes again.
Only a couple days after Kaylee hooked up with Chris, she was over at a friends on a Saturday helping her friend pack and clean up her house because she was moving. Her friend knew about our lifestyle, and was asking her a bunch of questions. “How do you find all these guys” “Who’s been the best” “Show me photos of them”. Her friend was curious and intrigued. Kaylee told her friend who was single at the time, to get on tinder and do the same, but she was a little bit intimidated to hook up with random guys. Their day went on and they moved some boxes & furniture into her friends new apartment. Once at the new apartment they had a glass of wine to relax and that’s when her friend started asking more questions. “So, how often do you hook up with these randoms?” “Your boyfriend Brayden doesn’t get jealous?” “You have to start telling me all the details”.
Kaylee got back to our place at around 5:30pm and told me that her friend was asking a bunch of questions and was really interested. She told me she was kinda horny after answering questions damn near all day and was going to swipe on tinder for a couple minutes. She laid down on the couch and swiped for a few minutes, matching with a couple of guys. Then we decided to start making Dinner. We were both in the kitchen and she got a message on tinder from a guy named Daniel. With most of her matches she would show me and asked if I know who he was. With 99% of her matches I have no clue, but I had met Daniel a few times before, he used to date one of my friends from my hometown while they were in university.
Kaylee was surprised and asked about him. I told her that he was a nice guy, good looking, wouldn’t cause any problems. I told her to reply to him, just don’t mention you have a boyfriend cause I don’t think he’d be into that. After they exchanged pleasantries on tinder, he quickly told her to add him on Snapchat. He was quick to ask what she was looking for, which she said “something casual”, he said he wanted the same and started complimenting Kaylee on her photos.
A cheesy compliment is the best way to get Kaylee to start revealing more. So her next few photos she made sure she had lots of cleavage showing, which he loved and started asking for more. Kaylee told me she was going to the bathroom to send him a photo in her bra. I obviously had no problem with that, and she quickly left the kitchen and returned a couple minutes later with only a bra and thong on. She saw me looking at her with a confused look and she said “what? I thought he would like a photo of my ass too”. I just chuckled. He sent her a dick pic which she said looked above average. They kept snapchatting while Kaylee and I finished making and eating dinner. While eating, Daniel asked Kaylee if she wanted to come over later. Kaylee asked if I was fine with her fucking someone I knew, I said yes. So she told him she could come later in the evening.
After we ate, Kaylee told me she was going to shower. Before hopping in the shower, she sent Daniel some full nude photos of her tits.
For context, Kaylee is about 5 foot 5”, 160lb. D cups, nice plump ass with light brown hair. Her boobs are definitely a focal point among most guys.
Daniel replied to her nudes with compliments, telling her how much he loved big tits and couldn’t wait for her to come over.
After Kaylee’s shower, she went to our bedroom to get dressed. She came out wearing a black mini skirt that was just long enough to cover her ass with a black low cut tank top with no bra on. I asked her why no bra, she told me Daniel seems to love tits so why bother with a bra. Then she lifted up her skirt to show me her purple g string. She looked so sexy, I wanted her for myself. But she told me to wait until she got back.
She continued messaging with him for about another hour while we sat on the couch. until he asked if she was ready to come over. She said “send me your address”, which he did. She typed it into her phone and laughed. I asked what she was laughing at. She told me, “I was literally at his apartment building today, he lives in the same building as my friend just moved in to” she thought it was funny and would be hilarious if she ran into her friend while going to his apartment. But if not told me she was going to tell her friend tomorrow. Which I also thought was funny.
She got into her vehicle and called me on her drive over. Once she arrived at his place, Daniel told her he’d come meet her at the front doors. I told her to keep me updated if she could.
She ended the phone call and I decided to clean up our apartment to keep myself busy and to kill some time. After an hour and a half I heard my phone go off. I figured Kaylee was on her way home but her text read: “Things are good, I’m just waiting to fuck him. I already sucked his dick and swallowed his cum fyi”
Some more time past and I was starting to wonder what was taking so long, her hookups usually last an hour to an hour and a half. But at this point she had been there for over two hours. Finally about two hours after her previous text, she texted again. “On my way home”
She walked in our apartment, hair quite messy, face a little red, but with a big smirk on her face. I asked how she was doing, she said great, I gave your friend a present! I was a little confused and asked what she meant. Kaylee then pulled up her skirt to show me that she didn’t have her thong on. She said “I decided on the way over there that since you kind of know him, I thought it would be nice if I left him a memento, so I left him my thong”. I thought it was really hot, pulled her in for a kiss and told her to tell me everything.
He met her at the front doors when she got there, gave her a quick hug while letting his hand brush her back down to her ass. She said she was immediately attracted to him, he was hot, fairly muscular, fit. When they got into his apartment, he grabbed each of them a beer and they sat on the couch talking and slowly got closer. He eventually put an arm around her and she leaned into him making sure he could basically see right down her tank top.
It didn’t take to long after that for his hands to start exploring, grabbing her boobs and then sliding his hands down her tank top while telling her how nice her tits were. She started grabbing and rubbing his dick while he continued to feel her up, moving from grabbing her tits to rubbing her clit. He said “God, I love that you didn’t wear a bra” Kaylee then sat up a bit started making out with him. It was wet and sloppy but fun. He then stood up grabbed Kaylee’s tank top and pulled it off, then slid his shorts off. His dick sprang up right in her face. She grabbed it, traced the tip of his dick with her tongue, getting it all wet. She then started sucking him, going fast with enthusiasm while massaging his balls. He was moaning loud and she knew he wasn’t going to last, so she pulled his dick out of her mouth, and stroked his long cock for a few seconds before putting it back in her mouth. She continued deep throating him, then sucking on the head of dick, then licking his shaft. He then grabbed her hair and she started going fast and hard with his dick in her mouth. He told her “I’m going to cum”, and she kept him in her mouth, swallowed and then he pulled out. She grabbed his dick, licking his head and shaft to clean up any excess. He pulled up his shorts and Kaylee grabbed her tank top to put back on.
Kaylee said she was disappointed they didn’t fuck. But after she put her shirt on, he said “give me some time and we can do more”. Kaylee then asked to use the washroom, which is when she texted me to give me an update. They sat and hung out drinking their beers for about 30 minutes, Kaylee was cuddled up with Daniel and started rubbing his dick over his shorts again.
She said she could tell he was slowly getting hard. So mid conversation with him, she starting pulling his shorts down. With her head on his lap, she stroked him and softly sucked his dick till he was fully hard again. He then striped Kaylee top off, sucking on her boobs, then she took her skirt off. He commented on her thong, calling it “cute”. He ate her pussy and rubbed her clit making sure she was soaking wet.
Kaylee asked “do you have a condom” and he said no. She got up, grabbed one from her purse and handed it to him. He ripped it open, put it on and grabbed her, throwing her back onto to the couch. She loved the aggression. She got into doggy style and he slowly entered her. Fucking her slowly and passionately while grabbing her ass with one hand. He started to thrust harder, in and out. Occasionally slapping her ass. The thrusts got harder, the slaps on her ass more frequent. She said she burried her face in the couch to try to contain her moans while she orgasmed. Eventually he flipped her over, fucking her missionary. She wrapped her legs around him and squeezed. He told her, I’m going to cum soon. He pulled out, stood up, took the condom off and came all over Kaylee’s tits.
Daniel grabbed some Kleenex to help Kaylee clean up. After that they laid down naked on the couch cuddling for a bit still fondling each other, until Kaylee told him she better get home. They got dressed, Kaylee subtly kicked her thong to the side of the couch on the floor to leave for him and then he walked her to her vehicle and gave her a kiss goodbye.
After Kaylee told me all the details, I took her into the bedroom, striped her clothes off and softly ate her out. She told me to fuck her, so I did. We fucked for a bit and I told her I wanted to cum in her mouth just like Daniel did. I laid down while she sucked me off and she swallowed my load.
The next morning, she texted her friend. “I had to come back to your apartment building last night, there’s a hot guy who lives a few doors down from you lmao”
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