Craigslist Chronicles Ch. 01

This story contains bisexual sex between 2 guys and a girl. If this isn't your thing, don't read it!

It all started the summer after I turned 18. I was a little bi-curious to say the least (actually I was more than curious, I wanted a dick in my ass!) but was always too scared to do anything about it. See I LOVED anal. I mean LOVED it. Honestly, I liked fingering my ass more than "rubbing one out." I got to the point where I could nearly fist my own ass! I felt like a pornstar.

A bit about me before I tell you any more. I'm about 6'2 with dirty blonde hair and hazel eyes. I work out a lot, so I'm in pretty good shape. I'm really lean, not huge and muscular at all.

One of my favorite things to do was go to craigslist and look at the different "mw4m" postings because yea I wanted a dick but I really liked girls. Then one day I found the perfect listing:

MW4 BI guy

Looking for a truly bi guy to be fucked by my gf and I. She wants someone to eat her pussy and I want a shaved ass to fuck. Must be HIV- and DDF.

Me-6'4 195 lbs 8.5" 26 years old

Her-5'5 120 lbs medium tits, nice tight ass

You- 18-22 hwp, enjoy anal, submissive

"This is it!!" I thought to myself. I quickly sent the couple an email saying that I was their man. While I nervously waited for their reply I started to get really hard and began playing with myself. Then I realized that I hadn't shaved in almost a week, so I ran upstairs and jumped in the shower.

I soaped up and shaved everything from my legs up. I was smooth and sexy and I knew it!Since I figured I had the time I began soaping up my ass again. I could feel my cheeks sliding against each other and my little asshole begging to be fingered. With an invitation like that, who was I to deny it? I began sucking on two of my fingers imagining they were the cock I would be sucking later that day then brought them down and slowly slid them into my asshole. I was so turned on at the time that I literally moaned!

After going to town on my ass for a few minutes I rinsed off and got out of the shower. I walked downstairs (naked cause who doesn't love walking around naked!?) and checked my email. To my surprise the couple had emailed me back already! My cock instantly sprang back to full hardness as I opened the email. I was so nervous I could barely breathe! I could feel my heart thumping in my throat and I felt as though I was going to throw up.

Dear Allen,

We would love to fuck you tonight. Please be at our place no later than 8 o clock. Come loose and ready;)

Sincerely,

Tom and Cindy

I was so excited I could barely concentrate for the rest of the day. Finally around 630 I started getting ready. First I grabbed my dildo (a nice, thick, veiny 6" deal) and started lubing it up. Then I got into bed and began fingering my ass while stroking my cock (7.5" not too thick). After I loosened my ass up a bit I started teasing myself with the dildo.

I began to slowly push it into my ass, just the tip at first, but gradually pushing more and more in until it was balls deep in my ass. I moaned out load and began stroking my cock again. I sat up and began riding the dildo hard moaning louder and louder till I was about to cum. I laid back and stroked my cock till I came HARD. Thick, ropy streams of cum shot out getting the whole way up to my face! I licked off what cum I could reach with my tongue then got up and got in the shower.

After showering again I looked at the clock and saw that it was already 7:20! If I didn't hurry up I was going to be late!! I put on shorts, long sleeve shirt, and sandals and hurried out to my car. If I was nervous before, I was near panic now.

Soon I arrived at Tom and Cindy's house. It was a decent sized hrick house with white pillars in front. I walked up to the front door and reached to ring the door bell. Before my hand even touched the bell, the door open and a man (Tom I assumed). "Hi, you must be Allen, come in!" He said to me.

"That's me!" I replied as I walked in. As soon as I was inside, I noticed that Tom was already naked! He was about 6'3 and seemed to be in good shape. He had black hair and dark brown, almost black eyes. I noticed all of this after I saw his cock. It was erect and covered in what I guessed to be Cindy's juices. It was at least 8.5" long and THICK. I started to get a little worried just looking at it.

"You like what you see?" Tom asked me

"I'm not going to lie, that's almost a little scary! I've never had a cock in my ass before and you are way bigger than my dildo!"

"Not to worry, we'll take it slow," Tom said as he winked at me, "However lets get some ground rules down before we go up to Cindy. So basically you are going to suck my cock and get fucked in the ass by me. Cindy is probably just going to watch at first, but you're pretty hot so she might join in pretty quick. When she does you'll be eating her out, then you can fuck her ass or her pussy. You can cum as much as you want, in either hole, but whenever you cum you need to eat your cum out of her. I'm going to cum in your ass at least 3 times before the end of the night, and I expect to keep my cock in after I've cum, so you're going to be pretty full. Sound good?"

"Of course!" I replied.

"Ok, take your clothes off."

"Right here?"

"Yes! Take them off!"

"Okay," I replied as I began removing my clothes. After I was naked Tom motioned for me to start going up the stairs.

"I'll be up right behind you, I want to see that ass." When I'd gone up a few steps I decided to tease Tom a bit, so I stopped and spread my ass cheeks showing my hairless ass and my nice pink hole.

"You mean this ass?" I said as I spanked myself.

"Mmmm yea, that's the one, now hurry up and go upstairs! I want to fuck that tight little hole," Tom replied as he smacked my other cheek.

I continued the rest of the way up the stairs and went into the only open door I saw. When I walked in, I saw what was easily the most beautiful girl I'd ever seen in my entire life. She was tall, at least 5'10, with long blonde hair and amazing tits. They weren't small, but they weren't huge either and her nipples were nice and small and erect. From there her stomach curved in in a perfect hourglass shape down to her ass which seemed to be amazing from what I could see.

"Hi...you must be Cindy" I stammered, still taken in by her beauty.

"Mhm, and you're Allen I presume?" She purred back, her voice oozing sexuality.

"That'd be me. Wow...I'm sure you hear this all the time, but you are amazing!" I told her.

"That she does," Tom said with a wink in her direction, "Shall we begin?"

"Sounds good to me, I can't wait to get at that cock." Cindy replied (and I really hoped she was talking about mine).

Tom went and sat down on a chair next to the bed and motioned for me. I walked partway there then got down on my knees and crawled the rest of the way, doing my best to look sexy. Once I got there, I began stroking his cock with one hand while I cradled his balls in the other. It felt even bigger than it looked! "Tom," I said, "I have a confession...I've never even sucked a cock before. I'll do my best, but keep in mind it's my first time!"

"Would you look at that Cindy," Tom said, "He's a virgin to sucking cock and he said he's never had one in his ass before either! Lucky us." This was true, I was a virgin when it came to cock. Obviously I'd nailed plenty of girls before, I'd even had sex with a shemale or two. But I'd never even had sex with a guy before. I wanted to be the fuckee not the fucker. If I wanted ass, I'd screw a girl.

In response to Tom's comment about being a cocksucking virgin, I decided to dive right in. I moved my hand further down his shaft and put the head of his cock into my mouth. It was far bigger than I expected, and I was almost wishing I'd found someone with a smaller cock for my first time. But now was not the time for regrets so I continued.

While the head was in my mouth I began stroking the shaft and playing with his balls. I started flicking my tongue around the head, trying to do to him what I liked girls to do to me. Then I took his cock out of my mouth and started licking up and down the entire shaft. I could taste Cindy's pussy on the cock so I'm guessing they were fucking before I got there. I decided to go deeper and put his cock back in my mouth.

I started going deeper on the cock, taking more and more of it into my mouth. I got about 2/3 of the way down before I gagged...hard. I honestly thought I was going to throw up. I quickly pulled back but kept his cock in my mouth. I really actually enjoyed the taste of it. I wasn't sure if it was his pre cum, or Cindy's juices that I liked, but whatever it was, I liked it!

As I took his cock further in my mouth again (but not to the point of gagging, not yet at least) I felt something at my asshole. I quickly realized that it was Cindy's tongue. She started rimming me, then full on eating my asshole. It was amazing! She was able to get her tongue surprisingly deep inside of my ass. I could have stayed like that forever, with her tongue in my ass and Tom's cock in my mouth. Soon though, she stopped and backed away. Then I felt something else at my ass. This time it was her hand. She began to finger me, just one finger at first, but quickly adding a second then a third.

Her hand was small enough that I really think she could have fisted me, but she didn't put any more than three in. She just took them out, added more lube, then put them back in. After repeating the lube, finger, lube cycle a few more times, she began to finger fuck me hard and fast. I started moaning around Tom's cock.

Cindy continued to finger fuck my while Tom grabbed the back of my head and forced me further down onto his cock. I started gagging again but was able to control it a little this time and thankfully didn't throw up (something tells me that would have ruined the evening). He kept my head down low on his cock, ALMOST to the bottom, then moaned loud and then let me up for some air. As I gasped he looked at me and said, "I want to fuck you're ass sooo bad. I'm going to make you scream into Cindy's pussy while you eat it I'm going to be fucking you so hard."

At that point he pulled me up and Cindy took her fingers out of my ass. Tom picked me up (he was surprisingly strong for his size) and threw me onto the bed. He pulled me up onto my hands and knees and started rubbing his cock against my asshole. I looked back and saw him rub lube up and down his cock, then smear the rest of it into my ass crack.

I looked forward again and was surprised to see Cindy in front of me already. I hadn't even heard her get on the bed!! She smiled at me and slid down a little so her pussy was right in front of my face. I could feel Tom teasing my ass with the tip of his cock as I began to lick Cindy's pussy. I started by slowly sliding my tongue into her pussy since it was gaping a little from Tom pounding it earlier.

As I slid my tongue into her pussy, Tom began to slide his cock into my ass. It was as if I could feel every single inch slowly pushing in, stretching my asshole in ways it had never been stretched before. True to his word, I moaned loud into Cindy's pussy as she moaned from the attention I was giving her. I began to lick all around right inside of her pussy, then I pulled back a little.

Tom was still slowly feeding his cock into my ass, at this point I'd guess he was about 4" in. He stopped for a moment to allow my ass to get used to his girth, which I was very thankful for. I began to suck on Cindy's "lower lips." After doing this for a few seconds I moved up and began to lick around her clit. As she moaned, Tom suddenly thrust the rest of the way into my ass causing me to moan as well. I felt his balls slap against my ass and he kept his cock there for a minute as I went back to licking Cindy's clit.

After he allowed my ass to get used to his cock, Tom began to fuck me, very slowly at first, with long deep strokes. He would pull his cock out until just the tip was still inside of my ass, then push it the whole way back in until his balls slapped against me. At one point he pulled his cock the whole way out and shouted almost triumphantly, "Look at that virgin ass gape!!"

"mmmhhhmmghhm!" was my reply as I was a little preoccupied with Cindy's pussy. It wasn't that I couldn't feel my ass gaping, or his cock pounding me, but I really wanted to get Cindy off. It's always my goal to make the girl I'm with cum. At this point I was literally sucking on her clit as if it was a little cock and fingering her pussy which was driving her wild. She was moaning even louder than I was!!

As if angry that I was giving Cindy a better time than he was giving me, Tom began to pound my ass harder and faster. He was still fucking me with deep long strokes, but the were much faster and his balls were slapping against me much harder. I felt like if anyone even touched my cock I would cum a gallon.

Soon, Cindy pushed my head away from her pussy as she came in my face. She didn't squirt, but she definitely gushed! She looked at Tom and said, "I want his cock in me RIGHT now!!" In response, Tom forced his cock all the way in and pulled me back onto him so that I was riding him. Cindy positioned her well lubricated pussy over my cock and slid down onto me.

Something about her pussy, I'm not sure what it was, drove me wild. She wasn't too tight, but it definitely wasn't loose. When she got to the bottom of my cock I said, "Cindy, I'm really about to cum, you should ride me quick if you want my cock before I blow!"

She responded by riding up and down which forced me up and down a little on Tom's cock. The sensation of having his large cock inside of me and Cindy's amazing pussy wrapped around my cock was too much. I began squirting stream after stream of cum deep into her pussy. I could feel my ass contracting around Tom's cock as I came, which in turn became to much for him and he began to cum in my ass!

Cindy slowly got off of my cock, careful not to spill any of my cum, and walked back around to the head of the bed where she was earlier. Tom, true to his word, didn't remove his cock from my ass after cumming and continued pounding me hard. I couldn't believe his stamina!

He forced me back into doggystyle which put my face right back into Cindy's recently creampied pussy. There was already a little of my cum leaking out which I hurriedly licked up. I started tonguing her pussy again, trying to get as much of my cum as possible. I could feel Tom's cum squelching around in my ass as he fucked me and the idea of it turned me on more than I would have ever imagined.

I continued slurping my cum out of Cindy's pussy until she said, "I think you've gotten most of it. Remember what I did to you earlier? It's time for you to return the favor."

I didn't even have time to respond before she'd rolled over onto her stomach and thrust her ass into my face. I'd never eaten a girl's ass out before, so I was a little tentative...until Tom thrust his cock in extra hard which forced my tongue into her ass. "In for a penny in for a pound," I thought to myself and began licking around her asshole. Surprisingly (or maybe I was just ignorant), it didn't taste horrible, it was just like licking anywhere else on her body. I began to enthusiastically rim her, again determined to get her off.

Tom started pounding my ass hard, and I realized that I was hard again. I wanted to get Cindy's ass nice and lubed so I could pound it. Tom kept fucking me harder and faster until all the sudden he came in my ass HARD. I could feel his cock spasming deep in my ass and I swear I could feel the cum leaking out into me. He moaned and slowly pulled his cock out, but not before reaching over the side of the bed and grabbing something. Once he'd pulled the whole way out he pushed something back in and I realized that what he'd grabbed was a butt plug.

"I'm just gonna take a little break...this has taken more out of me than it normally does," Tom said exasperatedly while he sat back in the chair that he had been in while I sucked on his cock. I turned back and continued eating out Cindy's asshole until it was soaked with my saliva. I then backed away and lined my cock up with her asshole.

I started teasing her ass while I reached around and began rubbing her nipples. I slowly began inserting my cock into her ass until I was balls deep. Then I began fucking her hard. I knew that I wouldn't be able to las long with the butt plug pressing on my prostate like it was and I wanted to make the most of the time I had in her tight ass.

Given the way she was reacting, I'm fairly sure Tom didn't spend much time with Cindy's ass. She was extremely tight and was definitely fairly new to the whole anal thing. I decided to make the most of it and began pounding in and out, hard and deep. I began playing with her clit with one hand while I spanked her with the other, then began pinching her nipples. Soon, she began to cum. I could feel her ass begin contracting around my cock and I couldn't hold it in any longer. I began to spray cum deep into her ass in what was easily one of the most satisfying orgasms of my life.

After I'd finished cumming I pulled out of Cindy's ass and collapsed backwards as she fell forwards. We were all exhausted to say the least. Despite Tom's boast of cumming at least 3 times in my ass, he couldn't move to fuck me and I was too tired to get up. Without realizing it, all three of us fell asleep.

I woke up the next morning spooning with Cindy, my cock nestled between her ass cheeks. Tom was still asleep on the chair as my cock began to stir. Cindy woke up as it poked her right in the ass. She looked back at me and said, "Again?" with a wink.

.....to be continued....?

This was my first story so any constructive (read positive AND negative) would be greatly appreciated! Also I'm considering continuing along this story line, but I also have a few other ideas I'd like to hash out, so if anyone would like to read more like this or something a little different (probably something strictly straight, maybe with Cindy) let me know!