Craigslist Chronicles

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

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Cindy wrapped her legs around my head forcing my tongue deeper into her pussy as she screamed in pleasure. "OH FUCK YES ALLEN!! MMM EAT MY TIGHT LITTLE PUSSY!" In response I slid a finger into her ass and continued eating her out. This caused another her to moan again and beg for more, a request which I gladly obliged.

As I slid a second, then third finger into Cindy's tight ass, I felt something at my own ass. I knew it was Tom who had probably just gotten home from work and was definitely very horny. I wiggled my ass in anticipation as Tom began rubbing his lubricated cock against my asshole. He teased my ass for a few more seconds then rammed his whole cock deep into my ass with one hard thrust. I gasped into Cindy's pussy and moaned as Tom began to fuck my ass hard and deep.

Over the past few months I had been spending more and more time at Tom and Cindy's house. It was at the point where I slept there more than I slept at my own house (of course sleep at their house was slightly less restful). Normally I would go over around 2 PM and spend time with Cindy, sometimes just relaxing, sometimes watching tv or movies, and a lot of the time fucking. Then around 5 or 5:30 Tom would get home and we would either fuck or eat dinner, then spend the rest of the night in bed.

After a few minutes of pounding my ass, Tom began to cum in my ass. He left his cock there for a few minutes until it was completely soft and Cindy had cum in my face. Then he pulled out and she got up. "We've got a surprise for you tomorrow," Cindy said in a sing song voice with a wink and a smile.

"What kind of surprise?" I asked excitedly

"Well if we told you it wouldn't be a surprise would it?" Tom replied.

"Good point..." I answered dejectedly.

"Don't worry you'll find out soon enough! Be here no earlier than 6:30 tomorrow!" Cindy said. I could hear the excitement in her voice, which was getting me excited! The next twenty four hours flew by and next thing I knew I was standing in front of Tom and Cindy's house again.

There was a note on the door that said, "Allen, Don't bother knocking, just come in. Then go into the downstairs bathroom and put on what you find. After that, cum on up to our room;)"

I did as the note instructed and walked in, then headed straight for the downstairs bathroom. When I looked inside I found a thong, a plaid skirt, and a bra. At first I was freaked out and seriously considered leaving. But then I thought of all the good times we'd had and decided that if they wanted me dressed like a girl I could do that. "Besides," I said to no one in particular, "Tom probably has a good reason for this, it must be some sort of humiliation thing."

I took the shirt and shorts I had on off (I'd long since stopped wearing boxers to Tom and Cindy's, they were just one more thing to take off) and pulled on the thong, skirt, and bra. I looked in the mirror and noticed that I looked nothing like a girl. I was way too tall and far too defined muscularly. My short hair didn't help either. Then I looked down at my legs and noticed that, "Wow, I have some nice legs, I'd almost think they were girls!"

I left the bathroom and headed up the stairs to Tom and Cindy's room. When I opened the door I was greeted with not one but two cocks!! Well more accurately one real cock (Tom's) and one strap on cock (Cindy's). "We wanted to preserve the cock to slut ratio, so you're the slut today!" Cindy said a little too excitedly for my liking.

"We've been planning this for a while, but the clothing was a last minute idea from Cindy. So slut, why don't you get down on your knees and suck on our cocks." Tom ordered.

I did as instructed and got on my knees in front of Tom and Cindy. It was obvious that Cindy was still getting used to having the big dildo swinging between her legs, but I swear I could tell she was enjoying it. I grabbed Tom's cock in my left hand and Cindy's in my right and began jerking them off. I alternated between sucking Cindy's cock and Tom's.

After a few minutes of sucking I could tell Cindy wanted more. They led me over to the bed and I got on my hands and knees. Tom walked around to my face and I immediately began sucking on his cock again. Cindy walked to my ass, lifted my skirt up, pulled my panties aside, and began to eat it out. She started rimming me, but before long was pushing her tongue as far into my ass as it would go. I continued sucking on Tom's cock, moaning around it, enjoying Cindy's tongue in my ass.

Soon she stopped eating me out and began fingering me; loosening and lubing my ass in preparation for her cock. I continued sucking on Tom's cock, varying my technique between sucking the head, licking the shaft up and down, and even deep throating it. While I blew him, I also cradled his balls with one of my free hands, I knew he loved that.

I felt Cindy's fingers withdraw from my ass at the same time I felt Tom's hands on the back of my head. Cindy pushed her cock against my asshole and I almost shivered in anticipation. After a few seconds of teasing, she rammed the whole dildo into my ass, the whole way down to its balls. As she forced herself into my ass, Tom drove his cock into my throat. I began choking and nearly gagged, but he held my head there while Cindy began fucking my ass.

After what seemed like an eternity, Tom finally let me up for some air. As I was gasping, enjoying the ability to breathe freely, Cindy asked, "You like that? You like my big hard cock ramming your tight little slut ass? Hmmm? Want me to fuck you harder? Want my cock deeper inside you?"

"MMMM yes Cindy, please!!" I replied. I didn't know what it was about the situation that was turning me on, but I was SO horny! It didn't help that my cock was in a thong and nobody was helping get me off. Cindy talking to me like I was HER slut instead of the other way around was interesting to say the least. Usually when it was she and I, I took control. That being said, I still found this turn of events extremely hot.

"Good boy Allen," Cindy said huskily as she began fucking my ass harder. Tom, who had let me up to reply to Cindy, grabbed the back of my head again and began to fuck my face. The sensation of the two of them fucking me from each side was insane. I felt like if Cindy would just stroke my cock once I could cum gallons.

After a few more minutes of deep fucking, Cindy slowed down and then stopped with her cock still fully inside of my ass. Then, while her cock was still inside of me, she began to try and finger me!! I couldn't believe it. I thought there was no way my ass could stretch ANY more, but there she was, sliding first one, then two, then three fingers into my ass! This in addition to the already large "cock" that was there.

If I could have said anything, I would have, but I was too busy dealing with Tom still fucking my face. As I felt Cindy force in the fourth finger, Tom stopped and took his cock out of my mouth. Cindy then removed her "cock" and fingers from my ass. I turned and looked at them.

"Come get on my nice big cock Allen baby," Cindy said. I couldn't refuse a request like that, so of course I complied! I got onto her in the same way she'd done to me so many times over the past few months. I tossed my leg over her and lowered myself onto her cock. I bent down and kissed her on the lips as I felt her cock slowly slide into my ass.

I began to ride her moaning the whole time, but wondering what Tom was doing. I knew he hadn't cum, so there was no reason for him not to join us. Then I realized what it was he was waiting for. Tom began to try and press his cock into my ass while Cindy's was still inside of me! "No, no!" I nearly shouted, "What the hell do you think you're doing!?!?"

"What does it feel like I'm doing? It's a little thing called double penetration. We always do it to Cindy, why not to you since you're the slut today?" Tom replied as he popped his cock into my ass.

"Fuck!!! Oh god!! OWW" I screamed. My ass felt like it was ripping in half. Tom slapped my ass as he continued to slide his cock in. Once he was the whole way in, him and Cindy allowed my ass to begin to get used to the stretching.

After giving me a few minutes, they began to push in and out of my ass. At first, they went in and out at the same time, and then they began to alternate. At one point, Cindy pushed in all the way and held it there while Tom began to pound me. He reached around and grabbed my nipples through the bra they had me wear while he fucked in and out, deep and hard.

I moaned loud as Tom sprayed his cum into my ass. After his dick had softened, he took it out of my ass. Cindy began fucking me from underneath. Due to my recently stretched ass and Tom's cum, she was able to fuck me faster than I'd even thought possible. She started screaming as she came from the strap on rubbing her clit.

As she came, I rubbed up against her just enough to make myself cum as well and I began to fill the thong I still had on with cum. Cindy pulled her strap on out of my ass and the three of us fell asleep in bed together, all well fucked and exhausted.

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As with Chapter 1, any feedback is greatly appreciated! I hope you enjoyed it:)