The Happiest Place on Earth

Where is the craziest place you ever had sex? It’s a question we all get asked at some point. Some of us know our response without hesitation, some of us have to think about it for a moment and narrow down our choices, and some of us don’t have anything more exciting than the shower or living room. It has likely become obvious from my blog posts that my sexcapades have a knack for being in interesting locations. My craziest place might be the first crazy place I ever tried. Having sex in public places is kind of a turn on to me, and I believe it all started back on a high school field trip with a girl we’ll call Eve. Eve and I had cashed in our v-cards on each other a little over a year before (which is a funny story for another day) and at the time she was the only girl I had ever slept with. Being as young as we were, we rarely got the unsupervised alone time we wanted unless we skipped school or one of us had a parent out of town. Then one day one of our teachers got approval for a field trip to Disney world.

Now I could share with you the details of how the trip happened, but I am going to give you the cliff notes and get you to the part of the story where things get interesting. Eve paid for the field trip and got her permission slip in on time, I did not. My dad instead took me to Disney that same day, only with park hopping tickets and no school escort. I met up with Eve and the two of us managed to talk a chaperone into letting us ride one of the rides alone since nobody was in line but a small group from our school and there was no reason to sit more than two people to a car. We found ourselves alone on a ride that I never learned the name of, that circles around on a sky track through “Tomorrow land” cutting in and out of the various buildings in that area of the park. I even have a visual for you. The red line is the track that the ride took.

So the ride takes off, moving at the same slow pace that it would keep for the entire ride. Literally being a horny teenager, I reached instantly between her legs and slid my fingers up her skirt. She pushed my hand away, much to my disappointment. Then the car went indoors and suddenly Eve was no longer sitting next to me, she was standing up, pulling her panties off. I wasted no time unzipping my pants. She hiked up her skirt and climbed on top of me and started riding me like it was a race.  Suddenly we were outside. Eve stopped in a moment of panic and fell frantically back into the seat opposite of us. We looked around, noticing that nobody could see us very well from below and that nobody was in sight up high with us. She came back over to me and climbed back on top, only this time she faced away from me, reverse cowgirl style. This started as we went back into another building and continued all the way back outside and around a very long outdoor stretch. Then we saw the trolley that had all of the cars our class was on as it exited Space Mountain while we approached. Eve stopped moving but stayed on top of me with my cock still throbbing inside of her. As far as anyone was concerned she was just sitting on my lap. We turned into Space Mountain and I sat up, pushing her forward just enough to give me control. Eve leaned forward and I gave her all I had until we emerged back into the sunlight. We went back to the appearance that she was sitting on my lap.

Eve kept grinding, trying to get as much movement as possible without making anything obvious, though nobody was in view on the tracks with us and nobody below could see anything from their angle. We came up to the last building and we could see our class mates getting off the ride to our left right before we went in. As soon as it went dark Eve began bouncing up and down even more wildly than before. It was hard to tell whether she was desperate to get herself off in time, or trying to finish the job for me, but whichever she was attempting it appeared to be working. I felt myself getting close and I let her know it was about to happen. That’s when it became obvious that she was working on me and not herself, because without any hesitation for her own pleasure, she pulled up off of me and sat in the seat across from me and took my cock into her mouth so fast I hardly felt as though I ever ceased to be inside of her. Typically this would be followed by one to five minutes of blowjob before I popped, but this time was different. This time it was almost instant. She held still, waiting to make sure I was all done before making that oh so loved slurping noise as she brought her head up, swallowed, and smiled with an empty mouth. She picked her panties up off the floor and wiped her mouth and my dick both clean and stuff them into my pocket and laughed. By the time we hit the exit we were all clean and my heart was racing. I realized it wasn’t from the sex; I had sat still for the majority of it. My heart was racing because of adrenaline; I liked the rush I got from having just had sex outside around thousands of people without getting caught. I liked public sex.

Once we got off of the ride I took her panties out of my pocket and threw them away and smiled to myself at the fact that she was going to be walking around Disney all day with a skirt and no panties. Up until lunch when we had to separate, I stayed with her and her group and made sure to play with her pussy every chance that I could. This all happened twelve years ago, so I can’t fill you in on any witty comments I made or even promise you that there were any. It was a far cry from the best sex I ever had, in fact if I made a top 100 list it wouldn’t be on the list in quality of the sex. It would however be number one in craziest places I think. It was a rare combination of solitude on the ride, a lack of restraints, and total willingness from both people involved. It also didn’t hurt that we never considered the possibility of a camera being on the ride. I’m sure some pervert out there has an underage Disney ride sex tape floating around from 1999. Speaking of sex tapes, I have a good story about making one or two of them. While I try to decide what I want to write about next, I’d like to hear from you all either in the comments or on Twitter about the craziest places YOU ever had sex.

Twisted Sisters

When you have a blog dedicated to sex stories, it’d be golden to have a good threesome story to share. Unfortunately this is sexual confessions from the guy next door, not the guy up city in the penthouse. I am not saying that I won’t one day have my threesome story to share with you, or that us every day guys can’t swing a 3-way. What I am saying is that I don’t have one yet, so what you get today is the story of the closest thing I’ve had to one. Let me take you back on a short journey to about four months ago. I had been casually seeing a girl we’ll call Joan of Arkansas (Joan for short from here out) and I’ll call you awesome if you get that reference. Joan travels often, both for work and because her step dad is loaded and the family is almost always on vacation. Our relationship at best could be described as a series of hit & runs. A quick dinner here, a coffee date there, a quickie in the car before her flight. She had only slept over twice and both times she was gone when I woke up the next morning which made me feel used, in a good way. This particular time she had a few hours to kill before catching a flight, but she didn’t just bring her baggage she brought a passenger who we’ll call Cherry. Joan introduced Cherry to me as her little sister, telling me that they were catching a flight to yet another beach destination with the family. Obviously vacations were much needed after a long 3 day work week of dreadful 4 hour long days. I invited my roommate who we’ll call Shorthorn to come with me to meet the girls and catch a movie. Of course my motives were quite clear, I needed someone to pull the little sister away while Joan and I snuck off for some alone time. Shorthorn however had other plans, and I was taking this trip solo.

In my head Cherry was going to be 13 or 14 and an absolute buzz kill. The date would be the equivalent of trying to get laid while you’re date is babysitting. In reality however Cherry was nineteen, and aside from being physically attached to her cell phone at all times she was quite outgoing and funny. When I showed up to the theater by the airport to meet them they had already bought us all tickets to the movie. Well, their dad’s credit card had bought us tickets at least. I typically don’t like to allow a date to pay for anything for me, but it hardly felt like a date and I got the sense that money was something they had never worried about. Ever. I honestly couldn’t tell you what movie we watched that day. I recall not wanting to see it very badly and being distracted by Cherry’s insistent texting and Joan’s constant rubbing of my dick and nibbling at my ear like a drunk girl on prom night. I made the attempt to take a “bathroom break” with Joan and leave Cherry to hold our seats while she ignored the movie and texted people. Joan however felt that we should watch the movie and “find time for that afterwards”. So in the theater we sat, none of us watching the movie. Towards the end of the film Joan rested her head on my neck and began kissing around my collar bone in a way that I could only assume was an attempt to leave a hickey. I ran my hand across her knee and only a bit up her thigh and looked over at Cherry who was looking me square in the eye. The eye contact was strange because instead of an awkward look away she maintained the connection in a flirty approving way. I held the gaze, intrigued and slightly turned on.

As we left the theater we all went and sat in my car under the pretense of going to get ice cream. Instead we sat in the car talking. Joan and I laughed, joked, and flirted while dropping subtle hints that Cherry should go into the ice cream shop alone and take her time. The subtleness was either lost on her, or she had no intention of leaving. After a few awkward silences Cherry finally looked up from her cell phone and blurted out “She’s on the rag, I’m not cock blocking you.” Joan turned around with a look at Cherry that seemed like it could have physically caused damage.

Cherry: What? It’s the truth. So are you going to blow him or are we going to the airport.

Joan: Sorry, she can be quite blunt.

Cherry: I’m not going to walk around alone like an idiot by myself in a place I don’t know. You two do what you gotta do, don’t mind me.

Me: She’s blunt alright. Its ok, we can wait until you’re back in town.

Joan: I don’t mind doing it with her in the car if you don’t.

I took a second, staring blankly while in thought. Joan’s biological father is a preacher and despite our past encounters she had always seemed pretty reserved. I sensed that I had hesitated too long so I stumbled through an ultra smooth reply “Ummm, sure.” Yep, Smooth. You could call me Keith Stone with lines like that. Still, it was a good enough answer because Joan said nothing else before getting to the task at hand. I settled back in the seat while Joan began to work her magic. I glanced into the rearview mirror at Cherry who was once again making direct eye contact with me. This time I looked away, back down to Joan, or the back of her head at least. This went on for a few minutes with me glancing into the mirror at Cherry occasionally. Then during one glance Cherry smiled at me and raised her shirt up. I adjusted the mirror down a bit to get a peek. Joan raised her head up and looked back at Cherry.

Joan: You’re such a slut.

Cherry: Said the girl with cock breathe.

Joan: And you’re a bitch, and you’re not helping.

Cherry: Looks like you could use some help.

Me: *laughing the entire conversation*

Joan: Well unless you’re crawling up here, be quiet.

Cherry: My lips are sealed.

Joan went back to business. Cherry however sat up in the seat behind me and started rubbing my shoulders and neck. A massage and a blowjob, what a novel concept. Her rub down moved up my neck and resulted in running her fingers through my hair and playing with my ears. Then her lips were on my ear and as she took a teasing nibble at it she whispered “How does this feel?” as she kissed wet and soft behind my ear and down my neck before biting into my neck right where it meets my shoulder. She sat back, arching her back and unbuttoning her jeans. She pulled them down a little bit and turned her back to me. I was perplexed by what she intended to do. I kept looked back down at Joan who had not stopped or slowed down in the slightest. It was as though she was somewhere completely different than Cherry and I. Cherry sat down with her back against the center console facing away from me and laid her head back on Joan’s arched back. Cherry took my hand and put it on her tits and squeezed. She exhaled and pushed my hand down her body and in-between her legs. I played along, but I couldn’t quite shake off the weirdness of knowing that the girl with my dick in her mouth was the sister of the girl grinding against my finger. Still, I wasn’t about to stop it from happening. If it wasn’t weird to them why should it be weird to me?

Between the over-thinking of the situation and the focus I was dedicating to getting Cherry off, I believe Joan was at work far longer than she anticipated. I remember thinking that when Cherry cums it would turn me on enough to push me over the top and help Joan finish the job. But when Cherry popped, Joan stopped. Cherry sat up and turned over; now with her face down like Joan she whispered something into Joan’s ear. Joan lifted up her head and looked at me in the most devilish look I had seen from a girl who until this point seemed so innocent. She took my hand and started sucking my fingers. The same fingers that were just quite wet thanks to her sister. It was another strange mix of being extremely turned on and deeply disturbed. Then Cherry took a hold of my cock and stroked it a bit before very briefly taking over for Joan. It didn’t take long however before Joan took back over and Cherry retired to the back seat to button up her jeans and fix her hair.  Joan finished her dirty deed and cleaned up after herself quite well. The two of us got our clothes adjusted back to normal and there was a short awkward silence broken by Cherry.

Cherry: Well that was interesting.

Joan: You’re a whore.

Cherry: I was bored, why should you two have all the fun.

Me: That wasn’t the first time you two have done that… was it?

Joan: Together like that? Yes. We have never shared a guy in any way.

Me: You two were a bit comfortable for sisters.

Cherry: It’s not like we’re blood related. Our parents got married two years ago.

Me: Well that is a lot less disturbing.

Joan: Did you think we were really sisters?

Cherry: Dude, ewww.

Joan: Wow, you really are a freak aren’t you?

Me: I’m a freak? I wasn’t the one tasting my own sister’s love juice.

In retrospect the experience was a lot hotter knowing that there was no blood between the two who were so willingly sharing fluids. Try as I might, I have yet to pull off a threesome. What I have managed to do is keep myself as a possible rest stop on all of Cherry and Joan’s many vacations and road trips. The moral of the story is: If your roommate asks you to come on a double date, you do it no questions asked. Luckily for me Shorthorn missed out on that opportunity and I benefited from his absence.