A couple of Failed Threesomes | 2016

It’s Ashleigh again, and it shouldn’t come as a surprise that I had always wanted a threesome. Honestly, I want more than that: as many guys as possible in every one of my holes and hands. One of my biggest fantasies is an entire football team, in uniforms and pads, just running a train on me. But guys tend to be more shy about their sexuality than they claim, and even getting two who are comfortable with each other can be a challenge.

One time, in high school, I managed to organize a “tag team” . . . literally: Two guys would take turns and “tag off” to switch. It could have been much hotter if they weren’t making WWE jokes the entire time. Then in college, my buddy “Ethan” tried to arrange an “Eiffel Tower”. One guy from behind and one in the mouth. But by the time we actually got down to it, Ethan’s friend was so drunk that he couldn’t even get it up. This was fine by me, as I would prefer a little more variety than just being a spit roast while two guys high five. And thankfully, so was Ethan.

Ethan was hardly my type on the surface: Average height, average build, lighter brown hair, with a tan, but had hot piercing blue eyes. He’s wasn’t fat by any means, but he wasn’t in great shape. He definitely had the “dad bod” before that became a thing. Contrast this with me: 5’5”, tan, highlighted blond hair, 110lb or so, and pretty fit. And if you are keeping track from my last story, yes, I did gain the freshman 5lb, but most of it seemed to go to my boobs. A few months into college, I was wearing 34DD, which I doubt was great sizing, but I didn’t know anything other than Victoria’s Secret. I sarcastically wish Reddit were around then to tell me why my bra didn’t fit.

My attitude, my body, and a big state college meant I was getting laid more than I could have imagined. I had at least ten guys as my FWB bullpen to choose from on any given day, plus whatever else I could get on the side. Ethan never crossed my radar sexually. I met him in my math class, and he was a smart and absolutely hilarious guy, who was among the few engineers that could keep his eyes on my face if I was wearing anything more revealing than a hoodie.

One weeknight, I met him at a party and we started playing beer pong. Normally, I’m not that good, but Ethan and I just clicked. It helped that he spent most of the time bringing up sex with the other team’s families: sisters, moms, dads, grandparents, pets. I got in on the fun by loading up some gay porn on my phone. This disgusted just about everyone equally. We’d end each game by shouting “the Aristocrats”. We managed to hold down the table the almost the entire night, and all the sex talk made me horny as fuck.

By the time we lost a game, it was late. I wanted to fuck bad, and almost anyone was game in my mind. Ethan knew. Ethan: So, do you want to go back to my room. Watch some Family Guy? Netflix had yet to be invented, so Family Guy DVDs and chill was our option. I casually rubbed my hand on his crotch to see what I was working with. Not spectacular, but workable. I’ll give the nerd a chance. I thought. Me: How about my room? My roommate has the OC. I knew my roommates were out of town that weekend. Plus, my toys were already there and I mostly didn’t want to have to walk home if he turned out to be awful.

Oh my, how first impressions can be deceiving. We spent the ride home making out while going over ground rules, and holy fuck, Ethan was kinky. Before this night, the most sexual thing I had ever “done” in front of him was maybe a pelvic thrust while making a joke. Now he is seriously telling me he is okay with pegging and erotic asphyxiation on a “first date”. I drew the line at choking because I’d never done it and didn’t want a dead guy in my roommate’s bed. Part of me was worried that he was just a porn addict, but he was so sex-positive about everything, I knew that he had done at least some of the shit he was talking about.

As soon as we get back to my room, we rip each others’ clothes off. He throws me onto my roommate’s bed and goes down on me, gently at first, with just a little variation. He knows what he’s doing. Might have been licking the alphabet, but I never asked. I plug in my vibrator and we go to town. Right at average cock size, but he is good. The first thing he asks me to do is stick a finger in his ass, and he loves it. He asks me to slap him in the face. Harder the second time. Harder the third time! He is going progressively harder with each slap, and I’m going wild. I cum. A tingly, rolling orgasm. I’m warmed up and he wants to keep going.

We put one of my small vibrators in my ass, and just a little tiny one up his. He goes down on me again. This time he is more aggressive, with more tongue. Ethan seriously knew more about my anatomy that I did. We switch up and I put my legs over his shoulders. My body gets warm and shaky when I’m about to cum hard. I drop the vibrator and warn him. He hangs onto my legs and goes back to cunnilingus, saying, Just do it in my face. I squirt twice right in his face, and he is loving it. Side note: This is why I did this in my roommate’s bed. You don’t want to have to go to sleep in wet bed later. Plus she was kind of a bitch, and she didn’t think you had to wash sheets more than twice a year. I’m pretty sure I washed her sheets at least once a week after my antics, and she never thought she had to do it at all.

I grab a glass of water, and pull out “Big Red”, my biggest dildo: 12 inches. Ethan winces a little bit and asks, For me?. I respond Don’t you wish. I suction Big Red to the footboard. I bend over and he gently edges into my ass. I get myself wrapped around Big Red, and the “three” of us go at it. Now a real cock is always best, but a red silicone tube the size of my arm can be a workable substitute. I stick one of my smaller dildos in my mouth to complete the fantasy. I love anal because of how strong of an orgasm it can give me. My entire body will shake, I almost black out, and I squirt hard. Add the simulated extra penetrations and every part of my body is just screaming. I hold back for what seemed like forever. I wanted Ethan to cum. I may be a kinky nympho, but I’m not rude. He is moaning, I’m almost screaming. I finally feel him cum in my ass, and I just let go. I pull Big Red out and squirt hard, three or four times. Ethan stuck his face in there for the last one as I collapse onto my roommate’s bed. There is no way we didn’t wake the neighbors.

Thankfully for me, Ethan wasn’t a multiple ejaculation kind of guy, because I was spent. We got the sheets off the bed and stuck in an OC DVD. Before we both passed out, I had to ask: Me: Ethan, do you know any real guys who would do that to me with you? Ethan: Well no one as big as that dildo. Me: Size is optional if they fuck like you do. Ethan: But bigger is better. I know a few guys who might be ok with it…

And this is how the failed Eiffel Tower incident came to be. It turned out fine in the end, as Ethan and I just had more rough sex and ass play with toys while his friend was passed out on the other side of the room. But I can tell you, we did later organize a real threesome. I don’t want to call it a true “Part 2” as I don’t know when I will write it, but stay tuned.

Edit: Formatting.