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Memoirs of a Bisexual: Chapter 6 - No Holes Barred

A slight change of plans leads to more discovery among best friends
This is a continuation of the series "Memoirs of a Bisexual." I recommend reading chapters 1-5 to familiarize yourself with the characters and timeline.

The following story is based on true events.

Chapter 6: 

Winter Break started and we were off from school for almost a month. Felecia went home to Louisiana for the holidays. I went back to my hometown and got a part time job bartending at a local restaurant. I needed the extra money for Christmas.

I was excited because Jeff had lined up an evening with his girlfriend, Layla, and her college roommate, Amanda. It was with those girls that Jeff and I started our sexual revolution and began exploring our bisexual curiosities. The four of us haven't been together since that one night. I was really looking forward to this night because not only did I get to play with Jeff, Layla and Amanda had started exploring their own curiosities, as well. Now with all of us back together for an evening, this could be quite fun!

I made arrangements with my job to get off work at 10pm and Jeff had made a reservation for a hotel room with 2 queen beds. The plan was for Jeff to meet the girls when they came into town and I would meet them at the hotel as soon as my shift ended at the restaurant. I was so excited, I could barely contain myself.

It was about 8pm and my partner behind the bar got sick and had to go home. This sucked because that meant I couldn't get off work at 10pm. I had to close, which meant that I would not be out of there until 1am. I was super pissed! So, I paged Jeff (Keep in mind, these were the days before everyone had cell phones). When Jeff called, I told him the news. He just said, "Hey Man, don't worry about it. We're still going to have fun!"

This made me feel better, but DAMN I wanted to be there now, not after midnight. But the time finally came and I was off work. I made a beeline to the hotel. Jeff had given me the room number so I went straight there. I knocked on the door and Jeff answered. I walked into the room and saw only Jeff and a king sized bed. I looked at Jeff, "Where are the girls?" I asked.

"Yeah, about that..." He said sitting down on the bed, "They aren't coming."

"Why not? What happened?" I exclaimed.

"Layla and I broke up." He said as if it didn't bother him.

"You two broke up in the last 4 hours?" I didn't understand.

"Well it was more like 8 hours ago." He said, "I called Layla to see what time to expect them, she said that we needed to talk. She knows about me and you hooking up and she was cool with it became she and Amanda have done the same thing. I also told her about Felecia and us hooking up that night. She seemed to be ok with it. Then she and Amanda hooked up with a guy and had a threesome. That kind of jabbed at me a little, but its only fair. So today when I called, she asked if we really should be in a relationship since we are having sex with other people and apparently have no intentions of stopping. She had a point. We are all exploring ourselves and each other, so why be in a relationship when we clearly enjoy sex with other people. So, I said 'No, we shouldn't be in a relationship.' She agreed. But I told her that we could still have fun together tonight. She didn't see it that way, so she decided not to come."

"So how are you with all this?" I asked, "I mean seriously."

"I'm fine, Dude." He smiled, "Like I told you earlier, we are still going to have fun. Since I knew it was going to be just us, I switched rooms to one with a king bed, so we can have more room to play with each other!"

I smiled back at him, "Hell yeah, Man! That sounds good."

I dropped my bag and started getting undressed. "I need to take a shower. I smell like bar food and alcohol."

I went to the bathroom and turned on the shower. I finished undressing in the room in front of Jeff. Seeing Jeff watch me started getting my dick hard. I turned and went to the bathroom and got in the shower. I wanted to take a quick shower because I couldn't wait to get back in the room with Jeff. I grabbed the soap and started lathering up my body when the curtain opened. Jeff was standing there naked with a rock hard cock. He stepped into the shower with me. "I figured you could use some company, " he said taking the soap from my hand, "besides, I could use a shower, too."

He took the soap and started lathering up my body. By now my dick was standing at full attention, which he didn't hesitate to service. Jeff slid his hand with the soap down and started lathering up my cock. Then he started stroking my cock with one hand, took the soap and was lathering and massaging my balls with the other. That felt so good, I had to brace myself against the shower wall. Jeff took his hand and soap from my balls and slid it up though my ass crack' lathering it up, as well. He was taking a finger and teasing my asshole. This was a new sensation for me. He kept stroking my cock, not stopping as he teased my ass with his other hand. I could feel myself getting worked up, "Jeff, you're going to make me cum if you keep that up." I cooed.

"I don't think so," he said, "Not before I get some!"

He moved to the side so the jet stream of the shower could hit my body and rinse me off. Then he dropped to his knees and took my cock into his mouth. He sucked at a fast pace and was massaging my balls. This felt amazing. I couldn't help moaning and panting as he was sucking me hard and fast. I knew I wouldn't last long. I could feel myself starting to cum. "Oh shit, Jeff, that feels so good." I moaned. I had my eyes closed, really getting into this. My orgasm was building. Jeff could sense it, so he completely surprised me. As he kept sucking my dick, he slid his middle finger up my asshole. There was a quick shooting pain that immediately subsided. My cock started to cum. I was in ecstasy as he sucked my convulsing cock and fingered my asshole. As I was cumming, I could feel my asshole constrict Jeff's finger as he continued to fuck me with it. Finally, I exploded in Jeff's mouth. Jeff kept swallowing each squirt of my hot load that I pumped into his mouth. I thought my knees were going to buckle I was cumming so hard. As my orgasm wound down, I regained my composure and my balance.

Jeff took my cock from his mouth and stood up. "How was that." He asked smiling at me.

"Dude, that was hot! I loved it, especially the finger." I said with excitement.

Jeff didn't have any experience with Anal sex with anyone. Neither had I except for the one time I finger fucked Felecia's ass when she rode my cock. I guess this was another curiosity that was about to be explored. "Now it's my turn to lather you up." I said grabbing soap.

Jeff turned around to face the shower. He let the water from the shower hit his face. I took the soap and lathered up his back. I ran the soap around the front of him, lathering up his chest and stomach, then returning to his back. I worked my way down to his ass running the soap into his ass crack and rubbing his asshole. He let out a moan as he backed his ass against my hand. I continued to make strokes up and down the crack of his ass. Then I reached around front and lathered up his raging hard 9 inches and his balls.

I could feel my cock starting to come back to life. Jeff did too because he backed his ass into my rising dick. By this time, I had created a nice lather on Jeff's cock. I dropped the soap and started stroking his dick from behind. I stood behind reaching around and stroking his cock with my right hand. I had my left hand on Jeff's hip. My cock was fully hard and I slid it inside the crack of Jeff's ass and was rubbing back and forth across his asshole. Jeff was getting into this as he was rocking his ass back and forth across my cock. I thought about trying to penetrate his asshole with my now raging hard cock. I decided against it because Jeff was in a zone. He was rubbing his ass against my cock, I kept stroking his dick with my hand. Jeff was leaning his whole body against me as I continued jerking his cock and grinding against his ass. His head was thrown back against my chest, his eyes were closed and he was moaning and panting. "Oh fuck yeah. Don't stop, oh don't stop...that's it. Oh, I'm going to cum!"

I thought about stopping because I wanted his cock in my mouth, but I decided not to because Jeff was lost in the orgasm that was building. I didn't want to interrupt it. So, I kept stroking his cock. I felt his dick start to convulse. I didn't stop, I kept my pace on his cock. Then his dick exploded. "That's it, oh yeah, stroke me!" Jeff was screaming. His dick kept squirting and squirting its load and Jeff kept rubbing his ass against my cock. I jerked every ounce of cum out of him. We settled down and rinsed ourselves off. Jeff looked at me and said, "Let's get out of here and continue this on the bed."

We dried ourselves off and crawled onto the bed. Jeff lay on his back and propped his head up on a pillow. He looked at me, "I want you to pretend my mouth is a pussy and fuck it!"

I straddled his chest facing him. I lowered my dick into his mouth. I cradled the back of his head with my hand and brought his head to me. He had my entire cock in his mouth and was sucking me while I pulled his head up and down. I started grinding my hips as I was fucking his hungry mouth. The sensation was amazing. Finally, I stopped and pulled my dick out of his mouth. He gave me a puzzled look. "I'm going to change positions," I said, "I've been wanting your dick in my mouth as soon as I got here."

I turned around, still straddling his head but facing the opposite direction. I lowered my body onto his and took his 9 inch cock into my mouth. We were in a nice 69 position. I resumed my hip motions, fucking Jeff's mouth as I sucked away on his cock. I loved sucking his cock. He always had precum dripping for me to lick up. I played with the head of his cock with my tongue. The head of his dick was so big and smooth, I just loved the way it fit in my mouth as I sucked it. Remembering the shower, I lubed up a finger with my saliva and started playing with his asshole. I kept sucking his cock as I made little circle around his rim with my finger, applying a slight amount of pressure. This was amazing! I was fucking his mouth, sucking his dick and teasing his asshole all at the same time. I didn't want it to stop. Then Jeff pulled my dick out of his mouth. "I want you to fuck me!" He panted, "I want you to fuck me in the ass!"

This made me so hot. I rolled off of him. "Ok," I said, "How should we do this?"

Jeff got off the bed, went to his bag and pulled out a bottle of lube and tossed it to me. "I want you to fuck me from behind." He said as he bent slightly over the side of the bed, hiking 1 leg up on the mattress.

I lined myself up behind him. I was excited, hard as a rock and slightly nervous. I've never done this with anyone before. I lubed up my cock and placed a few drops on his asshole. I reached around and grabbed Jeff's cock with my lubed up hand and stroked him awhile. I wanted to get him hot. As I did this, I ran my cock up and down his ass crack like I was doing in the shower. After doing this and stroking his cock, Jeff was ready to go. He was moaning a little and breathing heavily. "Now go in, go in!" He cooed.

I applied some pressure to his ass with my cock and watched the head disappear into his asshole. I slowly kept going. I got half way in when Jeff gasped and clinched up. "Relax," I said to him. "I'm going to take this nice and slow." I reassured him.

Jeff grunted a little but took in a deep breath and I felt his ass relax. I slowly continued the penetration until I was all the way in. His ass felt amazing! It was so hot and tight, unlike anything I have ever felt before. I told him that I was all the way in and I was going to bring it out. I slowly withdrew my cock on the out stroke, but not letting it pop all the way out. Then I went back in, this time a little faster than the first. "How does it feel?" I asked.

"It hurts a bit, but feels good at the same time. Don't stop, though." He affirmed.

I kept fucking him slowly. Then I increased the pace as he got used to it. His ass felt so good around my cock. So tight. Jeff started moaning a little and rocking his ass back to meet my dick on the in stroke, I knew it was feeling good to him. "Oh fuck yeah," he said getting into it, "Your dick feels so good in my ass. Oh fuck me!"

Jeff reached down between his legs and started stroking his cock as I continued to fuck his tight virgin ass. He was really getting into it. He started to talking dirty to me, "Do you like the way my tight ass feels around your cock? Oh I love how you fuck me! I love the feel of your hard cock fucking my ass!"

I sped up my pace and was fucking him hard. The slamming of my balls against Jeff echoed through the room as I continued fucking my best friend. I didn't know how much longer I could last. Just then Jeff screamed, "Oh, I'm going to cum!"

Then Jeff's ass tightened and started constricting my cock as his dick exploded! Jeff kept stroking his cock as it was squirting his load. His ass kept squeezing my cock as he came. This was too much for me to handle. "Jeff, you're making me cum!" I said as more of a warning.

"Don't stop fucking me! Cum in my ass!" He screamed as he was still cumming!

Just then my dick erupted, squirting my hot cum in his ass! Oh, it felt so good squirting my load in his hot, tight ass! I had never felt anything like it. Jeff was still slamming his ass against my cock. Then as Jeff calmed down, he stood up. My cock was still buried in his ass as my orgasm finished. I reached around him and gave his cock a few strokes and massaged his balls. "That was unreal'" Jeff said as he caught his breath.

"Amazing!" was all I could say.

I pulled my dick out of Jeff's ass and went to the bathroom to clean up. Jeff got in the shower again. We both crashed on the bed and drifted off to sleep rather quickly.

The next morning I woke up to a nice sensation. I opened my eyes to see Jeff sucking my cock. Oh, that was so nice. I laid there on my back and enjoyed it for awhile. Then the urge hit me to return the favor. I told Jeff to maneuver to my direction. He did so and I took his dick into my mouth and started sucking him. We were in a sideways 69 position enjoying each other's cocks. Jeff started teasing my asshole with his fingers. It felt awesome. I knew he wanted to fuck me, but I felt intimidated by his huge cock. As he teased my ass more and more, I remembered how great it felt when he fingered my ass in the shower last night. Finally I convinced myself to try it. "Ok, it's my turn to get fucked." I said.

He looked up at me, "I was hoping you would say that."

Jeff came up to my end waiting for how I wanted to do it. "I want you on top." Was all I said.

I continued to lay on my back, Jeff maneuvered himself in front of me and spread my legs. Jeff lubed up his cock and dripped a few drops on my ass. He rubbed his cock over my ass to tease it a bit. He stroked my cock while he teased me. I was starting to relax as he played with me. It was feeling so good and I was getting extremely turned on. Then in one motion Jeff inserted the head of his cock a few inches into my ass. It felt good with a slight bit of pain, but I still wanted more. Jeff felt me relax so he slowly went deeper into my ass until he was balls deep. I had 9 inches of cock in my ass and it felt great. Slightly uncomfortable but I knew that would subside as he fucked me. And that's what he did. Going slow at first then speeding up ever so slightly until he was fucking me at a good pace. Oh it felt so wonderful having that cock slide in and out of my ass. I started stroking my cock as he fucked me. He looked down at me, "I've been wanting to fuck you for awhile now." He said.

"We'll now you got your chance," I said, "Your cock feels so good. Don't stop fucking me. I want you to make me cum."

With that he sped up his pace. I could feel and hear his balls slapping the back of my ass as he continued fucking me. This was starting to get intense. I kept stroking my cock, then I started feeling my orgasm building. Oh this was it! I looked at Jeff, "That's it. Oh fuck me! You're making me cum!" I screamed.

Jeff swiped my hand away from my cock and he grabbed it and started jerking me off. With my free hands all I could do was grab the sheets beneath me and hold on. This orgasm was getting more and more intense. I wanted to buck my hips or move in some way but Jeff was holding me down as he kept pounding his cock in me! Finally, my cock erupted and shot hot cum all over my chest and stomach. I could feel my ass clenching Jeff's cock as he continued to fuck me. Jeff kept stroking me, my cock kept squirting and my ass kept constricting Jeff's cock until it sent him over the edge. "Oh now I'm going to cum!" He yelled.

Then I felt his cock explode and shoot his hot load in my ass. Oh that felt so good in my ass! Feeling his hot cum squirt inside me was awesome! Jeff continued to fuck me until he had nothing left. He rolled off of me and lay beside me on the bed to catch his breath.

What a way to start the day. As Winter Break continued, Jeff and I had so much fun together. It was a little more difficult to find time to be together because when we were home from school we stayed with our parents. But there were times where we could get a few moments for a quick blow job or a nice fuck. We were still discovering each other and our sexuality. I loved Jeff's cock, but I also missed Felecia's pussy.

Now that Jeff and I have crossed another line in our sex lives with each other, I couldn't help but wish I could get him and Felecia together again for another adventure. But that's a different story.

To Be Continued . . .

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © AveryBi420 2012

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