After Kaylee had sex with Owen and officially fucked another guy for the first time while dating me, we were both riding a high.
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Kaylee 23f at the time, wasn’t sure how I would respond to her sleeping with another guy, which is why the first time took her over a year of talking about it to make it actually happen.
But once it did happen, we couldn’t contain our excitement. With us living apart and only able to see each other on the weekends we spent most of our next weekend together fucking 4 or 5 times a day.
The best news for me, was that she enjoyed the thrill of having sex with Owen. She would tease me saying “I took his entire cock in my mouth” “I let him do whatever he wanted to me”.
The downfall was Owen starting texting Kaylee asking to go on actual dates and asking if she’d possibly be open to a relationship in the future. This turned her off, because she was in love with me and only wanted Owen for his dick. She didn’t want to lead him on so she told him no, and slowly stopped replying to his messages. That didn’t stop him from trying to talk to her and occasionally sending her a late night booty call, with him telling Kaylee how much he loved the sex and wanted to see her naked again. She wanted to fuck him again, but was to concerned with how clingy he was.
We did have security cameras in our home, but they were only connected to an iPad I had left with her when she had sex with Owen. The both of us decided that the next time she did this, I should have the iPad with me so I could watch. We were both turned on by this, I liked being able to watch while I was out of town at my job and she liked the thought of putting on a show for me.
So after she decided she was done with Owen, she did what any girl who wants some dick would do, and opened up her tinder again and casually browsed, but she wasn’t in a huge rush to find a replacement.
Her patience didn’t last to long as only two weeks after she hooked up with Owen, she wanted to hook up with another guy. She texted me during her lunch break at work. “I’ve had a stressful day, I’m going to see if any guys want to hang out tonight”.
It only took her having sex with one other guy, and instead of asking if it was okay with me, she was just going to go ahead and do it. I found it really hot, so I told her to go for it and let me know if she found one she liked.
When Kaylee got off work at 5, she told me she was snap chatting a few guys. One guy named Jake was down to fuck, but he would only send dick pictures and was making up excuses for why he couldn’t send a face picture. She said he had a nice dick, but didn’t want to fuck him if he wasn’t willing to send a picture of his face.
Another guy named Chris had been messaging her. She texted me again “This guy named Chris is hot but he doesn’t seem very sexual” (boy, was she wrong). I asked what she meant by that and she texted me back saying “well I was snap chatting him till 1am last night, sending him revealing photos but he just doesn’t come across as a hookup guy, more of a relationship guy and he’s 29, so maybe he’s not into it.”
She didn’t text me again for about for an hour, so it was about 6:30pm by now. Then out of no where said “Hey, Chris is coming over at 9”. I texted back asking if she had talked to him more and she said “Yes, he might be freakier than I thought, also his dick is huge”.
I asked her if they had been sending pictures to each other. Kaylee texted saying “I was horny and said fuck it and took some naked photos when I got out of the shower and sent them to him, he sent me some videos of him jerking off”
For reference; Kaylee is about 5 foot 5”, 160lb. D cups, nice ass with light brown hair that she usually does in a ponytail or bun. 27 years old now, 23 when this took place.
Kaylee then said she was going to make some supper and do some chores and would keep me updated. I decided to turn on some tv and watch sports while I anxiously waited.
An hour later at 7:30 Kaylee texted me again. “Christopher just asked if we’re really waiting till nine” then she sent another text right after “I told him our address and to come whenever he was ready”
I opened up the iPad to look at the security cameras, and they wouldn’t connect. So I texted Kaylee to tell her. She replied saying “Well I just pulled them up on my phone and they’re working, so I don’t know what the problem is, maybe we can watch together after”. I was a little annoyed, but oh well.
15 minutes later she said “He’s on his way, I’ll text you after we’re done ????”
I patiently waited, pacing around waiting to hear from her again. Knowing she was with someone who she described as having a huge dick was a thrill itself.
An hour past and no message from her and I started to worry a little bit, so I texted her saying “what are you up to”. No reply.
20 minutes after that I finally get a text “Oh my god, I can’t feel anything”. “He just left.” “He was amazing, my whole body is Jello”
When I finally got to see the video I couldn’t believe what I was watching.
Kaylee was once again wearing Lululemon short shorts, this time though she wore a black lace bralette with no shirt. She answered the door when he knocked, he came inside and they exchanged hellos.
She was feeling confident and wanted to be a little bold. She pulled him into the living room where a camera directly overlooks and they started kissing, his hands exploring her body while she used one hand to undo his belt. Kaylee got his belt undone and then dropped to her knees right there.
She undid the button on his jeans, and pulled his pants and underwear down revealing (in her own words) “the biggest dick I’ve ever seen”. Which he later sent her photo proof that he was 8.5”.
Kaylee quickly put it in her mouth to lubricate it with her saliva. Then slowly stroked him using both her hands. When he started to get semi erect, she looked up at him and said “You’re dick is beautiful”. She felt embarrassed she said that, but was caught up in the moment.
She then started to give him a blow job. She kept one hand on the base of his dick, while sucking on the tip, easing herself on to him. Once she knew he was fully hard, Kaylee started going farther down his shaft, until she was fully deep throating him. He had one hand grabbing her ponytail, but was gentle with it. She deep throated him for a minute and then continued by licking his balls up to his shaft and then softly sucking on the tip of his dick.
Kaylee got up and led him to the bedroom, where he grabbed her from behind grinding his dick on her ass and kissing her neck. She then took off her shorts,thong and bralette, while he took his shirt off. He told her to lay on the bed and ate her pussy while she rubbed her clit, she was so horny that she came extremely fast.
After she came, she told him to grab a condom. He put it on and slowly entered her dripping pussy, She said he was so big that she didn’t know if she wanted to scream in pain or in pleasure. After starting with missionary for some time, he grabbed her legs and threw them on his shoulders and started pounding her faster. Kaylee said she was in complete ecstasy, it was like nothing she had felt before with any other guys she’d ever been with.
He then told her to get in to doggy to which she obliged and he started fucking her from behind, which lasted quite awhile, Kaylee said doggy was amazing, until he stopped and told her he wanted to do anal.
Kaylee had only ever done anal with me, which she loved but we hadn’t discussed if she would do it with another guy. Kaylee told me after that she knew I might be mad, but wanted to please him, even though she knew it would really hurt with how big he was. So she ultimately said yes.
He took off the condom he had on, grabbed a new one to put on, while Kaylee grabbed the lube from the bedside table.
She applied the lube and then laid down flat on her stomach. He slowly entered her, while she moaned and gasped. He slowly fucked her ass until she warmed up to it, then he picked up the pace a little bit. They continued for a long time. Chris had got more comfortable and said to her “where have you been my whole life?”
Kaylee gets super turned on by little comments like that and at that point she just wanted his cum. Kaylee told him, “you better cum in my mouth”
He pulled out of her ass, took the condom off and laid down beside her. Kaylee quickly got between his legs and started sucking his dick like her life depended on it. It only took a short time before he unloaded inside her mouth.
She collapsed on the bed beside him, laying there out of breath, sore, tired but in complete happiness. She said they laid they together for about 10-15 minutes.
Not long after is when she finally texted me. “Oh my god, I can’t feel anything”. “He just left.” “He was amazing, my whole body is Jello”.
She called me shortly after to tell me all the details. Even telling me “I hope you don’t mind but I let him fuck me in the ass”. At first I didn’t know how to feel, but as she explained the rest of the details, I was so turned on that I told her she could do whatever she wanted with him, anytime.
This was the first time they met up, but it definitely wasn’t the last.
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