This story is lengthy, so I marked where the sex begins. Also, it would help to describe myself when I was 24.
>*I am white with black hair, a thick beard, and blue eyes behind a pair of black-framed glasses. I am 6 feet tall and 220 pounds. My cock is 5 ¾ inches hard and thicker than most, or so I have been told.*
I also feel the need to put up a disclaimer. This story does involve cheating, so if that bothers you, you may want to stop reading right about now.
**—PART ONE—**
When I started college in 2006, both of my roommates played *World of Warcraft*. I always enjoyed watching them play, and they wanted to get me to play along with them. So when *The Burning Crusade* expansion launched in 2007, I decided to join them because they said they were going to start new characters anyway. Since then, *World of Warcraft* have been a huge part of my life, even though I no longer play it. You might be asking yourself what this has to do with sex, but I assure you it is relevant to the story.
However, before I started playing *World of Warcraft*, I was mostly involved in roleplay forums. One of the groups I participated in decided to try out this website called IMVU. It was pretty much a virtual instant messenger where you can customize your avatar to look however you wanted. Most of the group didn’t like it too much so they returned back to the forums, with myself and a few others staying there.
The group on IMVU dies out within a few months because we could not find decent people to roleplay with. I decide to stay there anyway, since I already spent some money into the site. I ended up meeting a few new friends on this site, with one of them being my best friend to this day, who we will call Paige. We were both around the same age, and we both had a lot of similar interests. After a few days of just getting to know one another, we end up sharing our personal info and start communicating outside of IMVU. Within a few months of us getting to know each other better, I eventually ask her out, and she says yes.
Our relationship did not last a month. While we got along really well, this was the first time she was involved in a long distance relationship, which was also the same for me. She also hated having her picture taken, so I had no idea of what she looked like. That really did not matter to me, to be quite honest, because we were just online and our interactions were only text based and to turn someone down based on their looks in a relationship that isn’t even visual or physical is pretty shallow, at least in my opinion. But because of that, I always wondered if she was being honest with whom she was. Then there was the bombshell she dropped on me: I was the second guy she ever dated and while she was bisexual, she preferred women. After she told me she still felt uncomfortable being in a relationship with a guy, we just went back to being friends, but this time with benefits. And by benefits, I mean we continued sexting and watching porn together.
Let us fast forward to 2008 when I am still playing *World of Warcraft* but I was a bit more serious about it. Back when I played during *The Burning Crusade*, it was mostly just for fun with friends. When *Wrath of the Lich King* launched, I decided to start getting involved in raiding and PvP, since my friends no longer played. While I was leveling a new character on a different server, I ended up questing regularly with a group of people from the same guild. Since I was the healer of their group and they saw I was skilled, they sent me a guild invite. I was eventually well liked and trusted, with it only taking about two weeks before I was promoted to a high ranking officer.
After a month in the guild, some of the officers hinted that a member had been asking about my personal life. I asked them who it was, with them telling me it was someone I had helped a few times before. I found out who it was, and we will call her Jess. She knew how to play her character very well, but she lacked the skills to make gold. Since I pretty much lived in the auction house, I helped her out with gem and enchant costs, since she was also a member of our 10-man raid team. I start talking to her a bit more and she admitted that she has a crush on me. I had started liking her as well, so we got to know each other a bit better and eventually started dating.
While we were getting to know each other, I ended up telling Paige about it and saying that the benefits part had to be put on hold. She was a bit upset about it, but she understood and was happy for me.
Jess and I usually communicated through Skype, when we were not on *World of Warcraft*. She was also hesitant about showing herself, but eventually she did. She had light brown hair, green eyes, and a mole on her cheek like Cindy Crawford. She had a very thick build and was the same height as me. She only sent me a few sexy pictures during the time we dated, but she had what appeared to be C-cup breasts and a very big ass.
We had been together for almost a year and I felt that we should talk about visiting each other. Jess liked the idea of it, so I got a plane ticket and flew out to her. As much as I enjoyed spending time with her, the visit really wasn’t all that great. I spent 3 days with her and nothing too sexual happened (not that I wasn’t expecting it, but more hoping it would). We say our goodbyes and I fly back home.
Now let us fast-forward to year two of our relationship, when Jess made plans to come visit. This did not happen however, due to some unexpected car trouble that was more important. I told her not to worry about it and I just said I would start saving up to come visit much sooner.
Let us fast-forward once more to about 2 ½ years into our relationship. A guild incident happened in *World of Warcraft*, which started causing problems outside of the game. We started talking less but we were still a couple. I tried my hardest to keep our relationship intact, but Jess kept getting more and more distant. I eventually bring up that I could possibly come visit her within the next month or two, to which she tells me to not worry about it. I was just frustrated at this point and just stopped talking to her for a few days. My thought process was if she wants to talk to me, then she can message me. This carries on for a couple of days and while all of this was going on, Paige offered her support. A week goes by and nothing has changed between Jess and I.
A few days before she was supposed to leave for her family vacation, Paige messages me. She asks if I still had plans to visit my girlfriend, to which I told her I wasn’t sure. She then tells me that her friend was supposed to go with her on her to Florida but she had to cancel at the last minute. Since I live in Georgia, she asked if I would like to stay with her, since everything was already paid for and she did not want to be alone. I told her I would think about it.
I actually already had my mind made up. Paige is my best friend and in the next state over, so of course I was going to visit her. However, I was still with Jess and while things were still on the rocks, we needed to talk about it. My intention was to just break up with her, because it seemed like I was putting in all of the effort into our relationship, but I did not want to do that with just a text message. I wanted us to be conversing with each other when I said it. So, I left a message for Jess saying we needed to talk, about us. I never hear back from her that day.
Before I went to bed that night, I tell Paige I will be more than happy to come hang out with her. She gives me the address to the place her family was staying and I left for Florida Thursday morning. Jess never replied back to my message.
Like I mentioned before, I did not know what Paige really looked like but through out the years, she did send me images of some Swedish model who she claimed to look like. I do not remember her name, but the model was known for doing cyber-goth photo shoots. The model was very attractive and if she wasn’t lying, I wouldn’t mind walking around the beach with her at my side. Besides that, all I knew was that she was into body piercings and that she always dyed her hair.
It was early afternoon when I pull up into the driveway of the address she gave me. I honked on the horn and a few seconds later, she walked out of the house. I did see the resemblance to that model, but to me she looked more like [this photo of Krysten Ritter](http://www.short-haircut.com/wp-content/uploads/2016/08/Female-Short-Blunt-Haircuts-with-Bangs.jpg), but her hair also has teal highlights in it. She was wearing a bikini top that matched her hair, and a pair of faded blue jeans. When I got out of my car, she walked over and gave me a hug. She was over 5 ½ feet tall and had an average build. As she hugged me tightly, I could feel her B-cup breasts press against my chest, noticing she had her nipples pierced.
After I brought my stuff into the house, I lie down on the bed and relax a bit. Paige sat on the edge and started telling me that they got here around noon and that the rest of her family was in the house next door, which meant we had this one all to ourselves. Normally, her parents and the youngest brother stayed in the house they were currently in, while she and the two older brothers stayed in the one we were in. The younger didn’t want to come along this year and the older couldn’t because his wife was pregnant and didn’t feel like traveling.
After I got some rest, she said we should go over next door so she could introduce me to her family. I changed into a fresh shirt and we made our way over there. She had told her youngest brother about me many times, since we were all into gaming. We both got along quite well. However, her parents didn’t know me too well, so they had their concerns. After an hour of talking with them a bit, they got to know me a little better and seemed to like me.
It was still sunny outside and Paige said we should head down to the beach, since the forecast made it seem like the rest of our stay was going to be cloudy. I agree and she grabs some beach towels while I go back to our house and get a change of clothes. We load up my car and drive a few miles down, closer towards the boardwalk. After we find a place to park, she gets out of the car and removes her jeans, revealing a teal and black thong bikini, which matches her top. For her build, her ass was a perfect size. I whistled at her and she just gave me the finger, even though she was blushing.
Now, I am not really a fan of beaches. I never learned how to swim and since I was always a fat kid, I hated taking my shirt off in public. So for the most part, I just sat on the beach or walked the beach at night. This was still the case, so I just sat on the beach in my tank top and swim shorts, just in case I decided to walk knee deep in the water. After a few hours out here, the sun was starting to set and we decided to head back to the house.
Before that though, I needed to stop by a liquor store because I noticed there was a severe lack of alcohol in our refrigerator. We stocked up on Smirnoff Ice, Corona, and a lot of cheap vodka before making it back to the house. When we got back, her mom came over and said they were waiting for us to get back so they could order pizza and asked us what we wanted. We ended up getting a Meat Lovers, a Supreme, and a side of breadsticks, since that would probably feed me and Paige for 2 days. We all ate together and we both left for our house shortly afterward.
The rest of the night was just the two of us drinking and watching whatever was on TV. I should mention that I only ever got drunk once and since then, I always stop before it gets to that point. So after about 3-4 hours of light drinking, mixed with the occasional sips of Gatorade and water, we both call it a night. I head to my room, strip down to my boxers, and curl up in bed.
I wake up two hours later with a slight headache. I decided to go to the kitchen and grab another Gatorade, since that usually helps. As I make my way back to my room, I notice that Paige’s door is open and the light is still on. I walk over and knock on the door. She doesn’t answer but I do hear audio coming from her laptop. I walk in and turn the corner, seeing her lying in bed and watching porn. She was covered up, so I couldn’t see anything, but I did notice some movement down between her legs.
She noticed I was looking at her and she just waved at me. I walked over to see what she exactly what she was watching. It was a lesbian scene with Sasha Grey and some other pornstar I did not recognize. We usually watched porn together online but this was the first time we were in the same room. Since I was still slightly hard after waking up, I put my drink on the nightstand and join her in the bed to watch it with her. It only takes a few moments before she notices I am stroking my cock, when she tells me to get under the covers with her. I do what she asks, while also getting closer to her.
As I got myself closer to her, I felt Paige’s hand run up my thigh. Her fingers were already wet from her pleasuring herself. She managed to find my cock and gripped her fingers around my shaft and started to slowly stroke it, while she went back to fingering herself with her other hand. We had sexted many times before so I knew exactly what she enjoyed. I took my right arm and spooned her, while my hand groped onto one of her breasts. As the scene carried on for about 10 minutes, she would occasionally stop stroking me to play with my balls.
When the scene ended, she told me to pick out the next video for us to watch. Since we both liked Sasha Grey, I just typed in “Sasha Grey threesome” since lesbian porn doesn’t really turn me on, unless there is a strap-on or some form of penetration. I ended up finding a video that had Stoya and Tommy Gunn in it. I started up the video and we returned to pleasuring ourselves.
**—SEX STARTS HERE—**
About halfway through the scene, with Paige still stroking me, I tell her I am close to cumming. She then lets go of my cock and tells me to lie down on my back. I give her breast a squeeze before doing so. She then closes her laptop and places it on the nightstand next to her. She throws the covers off of us and straddles herself on top of me. As I look down, I notice that she has her clit and labia pierced, along with a small patch of light blonde hair. She grabs onto my cock and slowly eases herself down onto me, biting her lip as she does. She then grabs onto her breasts with her hands and starts rocking her hips against me, telling me she wants my cum inside her.
I sit myself up and grab onto her hips, guiding her up and down on my cock. She then grabs onto the back of my head and pushes my face into her breasts. I press my tongue against her nipple before I take it into my mouth and suck on it. She lets out a moan as she starts to bounce on top of me. I then move my hands to her ass and spank her as she continues to ride me.
I return my hands to Paige’s hips and hold her down on my cock as I tell her I am about to cum. She then pushes me down onto the bed and places her hands on my chest as she starts to ride me harder, while I place my hands behind my head. Within a minute, I finish inside her, but she continues riding me. She tells me she is close, so I place my hands on her breasts and play with them. After a few minutes, she finally climaxes and collapses on top of me. She then pulls the covers on top of us and we both fall asleep.
Once again, I wake up in the middle of the night, with my headache still lingering. This time, it is to the sound of her typing away on her laptop. I roll over and ask her what she was up to now. She told me she always has trouble falling asleep on vacation. I return to spooning her and we watch Youtube. She then mentions the elephant in the room: my girlfriend Jess. I tell her that I messaged her shortly after she told me about her friend canceling on her last minute, saying we needed to talk. I also tell her that I was going to break up with Jess before coming here, just in case what happened earlier was going to happen, but I did not want to just leave it as a message. I then tell her she never replied back, since I checked on my laptop earlier before going to sleep, with the message still being marked as unread.
After about an hour of watching Youtube videos, she tells me she is horny again. Without me even realizing it, the whole time we were watching videos, my hand was fondling her breast. I also didn’t realize that she went back to fingering herself as a result of that. When she told me that, I started getting erect again. I told to restart the video we did not finish from earlier. She started the video close to where we stopped at, with us continuing what we did earlier.
We make it a few minutes into the video and I felt like I was going to cum if she kept stroking me. I let go of her breasts and pulled her hand away from my cock. I then gave her ass a slap and told her to lie on her stomach. Paige looked back at me and smiled before doing so. She then went to close her laptop but I told her to leave it on.
I got up and stood at the foot of the bed. I then grabbed onto her legs and pulled her closer to the edge, with them hanging off the side. As I rubbed my hand against her pussy, she moved the laptop to the middle of the bed where we could both continue watching. I then eased my cock fully inside her and started thrusting into her. When my thrusts started getting faster, she placed her hand down between her legs and started rubbing her clit.
I keep going at the same pace until the scene ends. I then start to slow down as I tell her to find another scene for us to watch. Paige quickly goes through her own personal collection and just picks a video at random. It ended up being an orgy video that had Alexis Texas, Sophie Dee, and Faye Reagan in it, along with other stars I did not recognize. She started the video up and skipped towards the middle of it and we went back to fucking. After a few minutes of slapping her ass and penetrating her at my usual pace, she told me to go harder. I do as she asks and she starts moaning my name over and over again.
Roughly five more minutes have passed and we change positions. We are both on the bed and I am fucking her doggy-style. I feel like I am about to explode inside her and she then tells me she is about to cum again, which was a huge sigh of relief. We both try to cum together at the same time, but I could not hold it in anymore. I finish inside of her, which puts her over the edge. As I pull my cock out of her, she starts rubbing her clit very fast, squirting all over the bed.
Paige collapses face down on the bed, with her legs shaking. I give her ass a hard slap before I go get us a fresh towel to clean ourselves off with. When I get back into the room, I see her chugging down the rest of my Gatorade from earlier. I sit down on the edge of the bed and tell her she made a mess. She gives a quick sarcastic remark and we both laugh. She then said she was really tired and was about to pass out. I told her that there was no way she was going to fall asleep in her bed soaked in cum. I then told her she could sleep in my room for the night.
She protested and offered to sleep on the couch, but she eventually agreed to it. When she tried to get up and walk, she had a hard time keeping her balance. I then proceeded to pick her up in my arms and carry her into my bedroom. After a few minutes of us getting comfortable, we both pass out for the night.
Source: reddit.com/r/gonewildstories/comments/8bcyvq/mf_what_happened_during_my_trip_to_florida
Hope you all enjoyed the story. This was only the first day of us spending a week together.
If you want to read about my other experiences that I have written about so far, here they are in chronological order.
[Zoe, or how I lost my virginity.](https://www.reddit.com/r/gonewildstories/comments/8a42oe/mf_what_happened_in_the_computer_storage_room/)
[Naomi, or how I ended up sleeping with my boss.](https://www.reddit.com/r/gonewildstories/comments/866h0u/mf_what_happened_when_i_helped_my_boss_with_an/)
So what was the epilogue to all this? What came of Paige and Jess?