For a variety of reasons, I’ve always had a hard time staying faithful in relationships. Porn addiction, sex addiction, whatever you want to call it. One of my guilty pleasures was using Omegle for cam sex. I don’t know if it’s anything like it used to be, but damn there were some hotties on there! This story took place about 6 years ago now. At this point I was in a relationship going on a few months, but I figured what the hell, I’ll log on and see what’s happening. I didn’t have any cam sex that night, but somehow ended up talking with two girls across the country from me for about an hour. One of them was a little chubby but had a cute face, but the one I was really attracted to was Holly. She was a redhead (my favorite), freckles, 19, pretty skinny as far as I could tell but it was hard to get a good look at her body with how the camera was facing. We exchanged numbers after talking for a while. Figured it would be like the rest of the numbers I collected off sites like that – chat for a few days before things fizzle out.
My girlfriend Natalie didn’t live with me but she normally was over quite a bit, so I didn’t really text all that frequently with Holly or anyone else. When Natalie wasn’t there though, I talked with Holly frequently via text, phone call, or video chat. We got along great and I really felt a strong connection with her. But, I felt like I screwed up as far as what my intentions were (sexual, of course). We had become friendly really fast and neither of us broached any sexual topics at all. I was afraid to do so and ruin the short-lived friendship we had. What a bummer. I was resigned to just being in the friend zone here (not like it mattered, she literally lived across the damn country from me).
We continued talking. I had told her plenty about my life (except for having a girlfriend, wasn’t sure how she’d feel about that). One day, she calls me while I’m at work. She says she booked a flight to come visit me for a few days. WTF?? She hadn’t even checked with me on the dates or anything. I was freaked out. She couldn’t stay with me obviously, which is what she was planning. I told her I was sorry but I was going to be out of town for work during that time. She sounded very disappointed and I felt bad. I told her I will check to see when I can get some time off and call her back.
After I thought about it, I knew Natalie was housesitting for a family friend in a few weeks. She would have to stay there as there was a big puppy there she had to keep an eye on. I called Holly back. Those dates worked for her. She said she’d change her flights and a few minutes later she texted a picture of her flight schedule.
I was a nervous wreck for days. So many times I felt like backing out but there was nothing I could do. I also had no idea what Holly’s intentions were. Would she really buy a flight to come all the way here just so we could hang out and be friends? I had no idea if she was even attracted to me. This was how I justified it as far as Natalie was concerned – this girl is just a friend and nothing is going to happen. I told her a friend was coming from out of state to visit for a few days and that I might be slow to respond.
The fateful evening arrives and I pick Holly up from the airport. We hug, make small talk, I get her bag for her, and we head back to my place. It’s a little awkward and conversation doesn’t flow as easily as it had over the phone or webcam. I’m beginning to wonder if this was a massive mistake and I’m stuck with her here for 3 days.
We get back to my apartment and get her unpacked. I had no idea what the sleeping arrangements were going to be, as I only had one bed and a couch. We sit down and watch a few episodes of Portlandia (we had discussed at length in the past about how much we enjoyed it) and she started to lose steam.
“I’m exhausted. 3 different flights to get here with semi-long layovers makes for a long day. Plus, it’s 3 hours later back home.”
“I totally understand, that’s a crazy long day. You can go crash in my bed, I’ll sleep out here tonight on the couch”, I said.
She nodded and that was that. I laid on the couch wondering what the hell I was doing with my life. Omegle was a dumb site anyway and now I have a stranger from the east coast sleeping in my bed while I’m stuck on the couch. And I have to work tomorrow, so she’s going to be hanging out by herself in my apartment all day. What could go wrong??
In the morning, I wrote her a note as to where to find some things, recommendations for lunch if she wanted to pick something up, etc. She texts me good morning about 10 and we talk throughout the day. We make plans to go to sushi for dinner and hit some bars. If anything is going to happen, I figure tonight’s the night.
After work I went home to find her dressed in a gorgeous sunflower dress – very light and springy. It looked amazing on her and outlined her curves beautifully. I hadn’t really noticed her body until then. She was about 5’6″, perky tits that looked like they’d fit in my hands perfectly (spoiler alert: they did) and legs that somehow looked like they were longer than mine even though I’m 5 inches taller. As far as I go, you can do the math on my height. I was pretty skinny at this time but had recently started going to the gym and working with a personal trainer so I was starting to add muscle definition. One thing I’ve always had going for me is the V (or Apollo’s belt, if you will) which we will come back to later.
We go to sushi and have a great time. We are at a place that has the boats that float by and you pick up what you want. We ate a lot and then headed to the nearest bar. We drink a fair amount but neither of us are wasted, just a nice buzz. Luckily my apartment is close by so we walked both ways. As we walk back, even my buzzed self doesn’t want to pull anything and have it backfire, I still had no idea what was going through her head.
We got back, both of us lay down on the floor and we put on some more Portlandia. I figured the chance was over and hoped my buzz would just help me forget the fact that this was going nowhere. But then, I look over, and Holly is staring at me. I will never forget those big green eyes looking at me. Before I had the chance to react, she leaned in and kissed me. We began passionately making out. Before long, she gets on top and starts pulling off her clothes (and mine). I was not expecting this, but damn was I happy.
I unhook her bra to reveal those perky tits that had been teasing me from inside her sundress all evening. I pulled her down and immediately took them in my mouth. She gasped as I grabbed her ass and gave it a smack. When she took off my shirt, she immediately noticed my V.
“Oh my God, you have a V. Sexiest thing ever”, she said as she started kissing down it slowly before hitting my jeans. “These are coming off now.” I wasn’t going to object.
She pulls them off and out comes my cock, bursting through my boxers. She wastes no time in taking it in her mouth and giving me one of the best blowjobs of my life. I have no idea how she generated that much saliva but my dick was soaked by the time she was done. I pushed her off and decided I needed to return the favor.
I started licking her clit while slipping a finger inside her. She was super wet already. Her moans picked up in volume as I slipped another finger in while continuing to lick her clit, sometimes taking a break to shove my tongue inside her. Oral is such a turn on for me, both giving and receiving, and I feel like I’ve failed if I don’t get a woman to cum from me eating her out. I did not feel like a failure that evening.
She came in about 5 minutes. I figured she needed a break so I rolled off of her, but I was wrong. She immediately got up and mounted me before I could even ask if I should get a condom. God it felt so good inside her though. Her pussy was made for my cock, it was like a glove. I grabbed a hold of her ass and spanked her while she rode me. Instinctually, I grabbed her throat (not a good thing to do if you haven’t talked about it beforehand). She immediately raised her head up to expose as much of her neck as possible though so I knew I had the green light. I choked her with one hand while I played with her clit in the other. I could feel her contracting on my dick, cumming again. I had alcohol in me though, which meant I could last way way longer than I could sober.
I roll her off of me and tell her to get on her knees. She happily obliges. Her ass looks so good bent over in front of me. I enter her from behind and now she’s getting really loud. I spank her, pull her hair and am getting pretty rough now. She loves it. I feel like I could do this for hours but soon enough I feel the welling up of an eruption.
“Fuck, I’m gonna cum”, I grunt. She starts bucking her hips faster, encouraging me to do so inside of her. I don’t let up and start shooting spurt after spurt deep into her pussy. She drained me of every drop.
I collapsed on the floor next to her. We both look at each other, beaming, and I realize that 2 more days is not going to be enough time.
Source: reddit.com/r/gonewildstories/comments/gk3n8r/met_and_fucked_a_girl_off_of_omegle_cheating
Fantastic story! How did things go with her and with your gf?
Very hot how she didn’t give you a chance to ask about condoms, and had you finish inside her!
Love to hear about the next 2 days