My first Omegle encounter [M/F] | 2016

This happened about four or five years ago. I was a pretty socially awkward guy but I did really enjoy getting on Omegle and Chatroulette and webcam sexting girls on there. Never did I think that I would actually meet one of these girls.

In this instance, after disconnecting with my last partner, they showed up on my screen. One was a slightly larger girl but with a really cute face, the other was a skinny redhead, hair down to her shoulders, curly, and a great, tight body. I talked with them both for a while, flirted a little bit, got their Facebooks, called it a night. No big deal. They lived in South Carolina and I was in Oregon, so I never thought meeting up would even be an option.

I started texting Tracy, the redhead, and that escalated to drunk dial phone calls. We started to Skype as well, and she asked if she could come and visit me. She had never been to Oregon and likes to travel. I told her she could crash with me if she stayed over - I've got a comfortable couch. A week later, she arrived.

I picked her up at the airport around 9 pm - she looked exhausted from a long day of travel. We grabbed some dinner and headed back to my place to watch Workaholics. Watched a couple episodes before she tells me she needs to sleep. I let her take my bed and sleep on the couch that evening. At this point, while attracted to her, I'm not even really thinking that we are going to hook up and she's just there as a friend. Definitely turned out not to be the case.

I went to work the next day - didn't want to wake her up so I just left her a note. We texted a bit throughout the day and made plans to have sushi downtown and check things out. Sushi went great, and from there we hit a couple of different bars in the area. At this point we are starting to get a little more touchy and flirty. After three or four drinks each, we head back to my place and put a movie on.

For some reason we were both laying on the floor instead of the couch right above us. She looked at me with intense green eyes for a moment before pulling me closer for a kiss. I immediately became rock hard - it was one of the most passionate kisses I've had. She gets on top of me, straddling my cock, and immediately pulls her top off and unhooks her bra, exposing her beautiful, pale B-cups. We claw at each other hungrily - each of us taking turns pulling off the others' clothes. When she pulled off my last layer, exposing my dick, she blew me for what seemed like 20 minutes. Thankfully I had some alcohol in me; I last longer when I do. I repaid the favor, flipped her off of me and gently started licking her clit while I slid a finger in. She was extremely wet but also really tight - I had to work at her with a finger before being able to get two in. She squirmed and moaned in pleasure as I started to more intensely lick her clit. I could feel her body tense up as she came into my mouth (and on the carpet).

We took a short break before I led her to my bedroom. I was still rock hard as I brushed the tip against her pussy - it was still soaked as I pushed myself inside. What an amazing feeling it was - she was so tight it took about five minutes of slow thrusting before I could fully get all the way inside. I loved playfully biting her erect nipples while fucking her, which really got her wild. She was yelling and I lived in an apartment, but didn't think about it until after. We switched to doggy, where I had an amazing view of her tight ass. I spanked her until her ass was bright red. I once again was grateful for drinking because I would have cum way earlier otherwise.

She screamed she was going to cum again, and I was close as well so I went for it. Grabbed her thighs and pulled and pushed her harder and harder until we are both screaming. We cum at almost the exact same time - I collapse on top of her, leaving myself inside, enjoying her pussy pulsating against me. At this point I knew I was in for a fun week with her. I pulled out and we laid next to each other, drinking in each others' bodies, laying in our own fluids (lots of cum with a little bit of her blood) before passing out to do it all over again the next morning.