Becoming a Bi Boy

This story is 90% true, I just had to change names and some minor details for privacy. Enjoy and please comment. I can continue if I receive positive feedback.

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The night started out the same as many nights before. Several friends gathering at the end of the week to let go of some stress and have a good time. It was how the night ended that would change not only my weekend, but my whole life.

Monica and I had known each other for over a year. We met through a mutual friend and hit it off fairly quickly. It was obvious to both of us that we made good friends, but that's where it stopped. Both of us were too independent and set in our ways to have had a serious relationship together. That didn't stop us from having our fun though. Several months after we met we went to a friend's party. After some drinks and laughs we made it back to her place and ended up sleeping together. The next morning we talked it over and that was when our friends with benefits phase started.

She was certainly a catch for any guy. She weighed no more than 105 and stood about 5'7" with her long shapely legs. Deep brown eyes with the long wavy hair to match. Her firm round 32C breasts and a tight firm ass that she got from running 5 miles a day. She was white/Mexican mix and her Hispanic features with light skin made many a man drool. I would always see the jealous look on other guy's faces when we were out to lunch or at a football game. I was about as average as you could get. I stood 5' 11" and 180 with an average frame. I worked out every day but I was no body builder. My short brown hair and brown eyes were nothing special. I wasn't an ugly ogre that women ran away from, but I wasn't exactly stopping traffic either.

It was the dream every young guy has I suppose. I was able to do all the things I enjoy with a hot chick with similar tastes and got to fuck her whenever I wanted, but we still were able to live our own lives. It worked out great for us. There was no pressure and no drama. Every couple of weeks if one of us needed some release it was only a phone call away. It was one of these encounters that my life changed.

I went over to Monica's place on a Friday night for a few drinks and some good conversation. We had both had a rough week at work and needed to blow off some steam. Her room mate Jeff came home from the gym about 30 minutes after I arrived. Jeff had only lived there about 2 months. I had only met him several times but he seemed like a cool guy. He had a dirty blond hair and green eyes and the typical jock look. He was about my size but was more built than I was. Jeff was also bisexual. He said hello and then headed off to shower and change. He joined us on the patio after he got cleaned up for a couple of beers and laughs.

As the night went on the alcohol began to have it's affect. All of us were a little tipsy and Jeff went inside to play a hockey video game and Monica brought me out another beer. After I drank it down, I asked Monica if she felt like fooling around. She said yes so we headed to her bedroom. Jeff knew our situation and paid us no attention other than a slight smirk as we made our way past him.

As the clothes came off we fell onto her bed and began kissing each other. Her hard nipples brushed against my bare chest and stomach as she kissed and playfully bit on my neck. Her skin was smooth and soft and I always enjoyed feeling her naked body against mine. Her soft full lips kissed her way down my chest, pausing briefly to lick my nipples.

She definitely knew her way around a man's body, and her touch mixed with the effect of the alcohol in my system had me on cloud 9.

Monica stood up to slide her sweatpants down exposing her glistening wet shaved pussy. I followed her lead as I removed my jeans and boxers allowing my swollen 7 inch cock to spring out from it's confinement. I sat on the edge of the bed and pulled her to me so I could suck her lovely tits. She moaned softly as my tongue drew little circles around her nipples. Her hand reached down grasp and slowly stroke my cock as I teased her nipples with my mouth. Then she dropped down to her knees in front of me.

The tip of her tongue traced along my balls as she gently stroked my cock. I laid back as she licked up the length of my shaft up to the head. Then after a few more sensual licks her mouth closed around my moistened cock. She started with slow deep sucks, allowing her saliva to coat my penis before she swallowed all 7 inches. Her pace picked up as she deep throated me over and over, every now and then releasing my cock only to lick and suck my balls. Monica was by far the best cocksucker I had ever been with.

Her expert sucking, combined with the alcohol had my head swimming. She told me to roll over which I quickly did. She had mentioned to me several months before this she had always fantasized about fucking a man with a strap on. She asked me if I ever would do it to which I quickly shot her down. And while I had since then given in to letting her lick my ass, which I very much had come to enjoy, getting fucked in the ass by her was off the table. That didn't stop her from asking me about it though. It seemed every time we fucked she would ask if I had changed my mind.

As I stood bent over the edge of the bed she knelt behind me stroking my spit covered cock and her tongue buried in my ass. As good as she could suck a dick, she could lick an ass just as well. I never thought I would like it as much as I did but it drove me wild. Tonight it felt even more intense than usual. Perhaps it was the beer talking, but I felt more adventurous as she worked my ass and cock over.

As if she could sense my inhibitions melting away she laid on top of me kissing my back and shoulders and rubbed her finger over my asshole. I was a bit surprised but for some reason I did not shy away from it. "Maybe I should have not drank that last beer" I thought to myself. When she saw I didn't pull away from her, I guess she figured it was time to test the water.

She moved back down to tongue my virgin hole again and I heard a bottle open. Moments later I felt her finger rubbing a cool liquid against my puckering hole.

"Go ahead." I said to her in my drunken daze. This was all new to me but I was unable to resist her.

Her lubed finger slowly pressed in to my ass and I felt my sphincter close around her finger. She excitedly gasped and remarked how tight I was. Why was I going along with this?

After a moment my ass began to loosen up and she added a second finger. It didn't take long of her fingering my ass for the pain to go away. It even started to feel good. Before long I realized I was actually pushing back and fucking her fingers with my ass.

I couldn't believe how good it felt. She withdrew her fingers and I was shocked that I let out a small whimper as she did.

"Oh, is someone feeling sad that his ass is empty?" She playfully asked.

I started to speak but she just put her finger to my lips to keep me quiet.

"Shh, just be quiet and relax. I promise you will enjoy this and if not we will stop. OK?"

I simply nodded my head at her. We both knew she had me.

I put my head down on the bed on the bed as she reached in to her bedside drawer and pulled out a strap on and stepped in to it.

She applied more lube to my ass and I felt her press the tip of her rubber cock against my hole. She slowly pressed in to me and the rubber dong slid inside making me gasp. She waited for me to get used to the size and then pressed again. She slowly worked it inside me until after only a few minutes I felt her hips against my ass cheeks. I couldn't believe it. Here I was with my long time fuck buddy burying her fake cock all the way in my ass.

Then she began to fuck me. She started slow steady then gradually picked up speed. Her hands gripped my shoulders as she pumped my ass like she had a real cock. My head was swimming and I moaned like a whore with every thrust. The more I moaned the more excited she became. Her thrusting got more and more deliberate and forceful.

She surprised me with a quick smack on my ass. " That's it, take my cock like a good little slut." She hissed at me. A whole new side of her had come out as she fucked me harder.

She pulled out without warning and my ass felt empty without the cock inside.

"Why did you stop?"

"Do you want it back?" She teased.

"yes." I said eagerly.

"Get doggy style on the bed." She ordered, and I complied.

"Now beg me for it."

I looked back over my shoulder at her.

"Please give it to me." I whimpered.

"You can do better than that." She said to me. "Make me believe you want it."

So even more pathetically I said to her "please fuck me in my ass some more."

"Fuck you with what?" She coyly asked me.

"With your cock."

"Then tell me," She said sternly. "Tell me what you want right now."

"Please Monica. I want you to fuck my ass with your hard cock"

"Louder." she ordered.

So I complied, as loud as I could without blatantly screaming.

"PLEASE STICK YOUR HARD COCK IN MY ASS AND FUCK ME MONICA!"

And with that she climbed up behind me on the bed and rammed her cock inside my eager ass. Amazingly, I felt relieved. I actually felt good about being used like a fuck doll. She pounded my ass like a woman possessed. My cock was throbbing and I moaned like a virgin from the assault on my sphincter. I was so caught up in the fucking I was receiving that I didn't even notice Jeff poke his head in.

Of course he had heard the commotion. How could he not have?

"Hey Jeff," she said casually.

I looked over at him as she continued to break my ass. I was getting fucked like a hooker on payday in front of a near total stranger but I didn't care. I just wanted to keep being fucked like the anal man-slut I was becoming.

"You know Jeff, he seems to enjoy cock in his ass so much, maybe he would like one in his mouth too." She happily said.

He chuckled "I bet he would. Let's see."

Jeff took off his shirt as he walked in front of me. He dropped his shorts and his thick and veiny cock was pointed at my face like a bullet. It had to be 9 inches at least. I just stared at it not knowing what to say or do, but he knew what to do.

Jeff placed his strong hand on my head and guided it towards his cock. In a trance I opened my mouth and took him in. He moaned as I tried to work more of his cock into my mouth. I pulled off and spit on it and ran my tongue over his head. I was on autopilot, thinking of all the things I liked when I get my dick sucked and tried to do it for him.

I jerked his dick to make sure my spit covered all of it and then dropped my head back on to it.

"Oh wow," Monica remarked. "He is taking to cock like a duck to water."

My lips slid up and down his shaft as she slowed down the pace and grinded her hips deep in to my ass. I looked up at him as my head bobbed up and down his stiff prick. He smiled down at me and I knew I was doing a good job so far. I tried to get as much of him in me as I could. Monica even helped by pushing my head onto his swollen rod as she fucked me.

For a brief moment I had a flash of reality. Just a couple of hours ago I had been just another average, everyday straight guy. Now here I was being powerfully fucked in the ass with a rubber dick, while a bigger and real cock took my mouth's virginity. And I was enjoying every second of it.

As my hand massaged his large nuts I could taste his salty pre cum coating my tongue. The taste turned me on even more and I fucked her cock as much as she was fucking my ass. He grabbed my head and began fucking my face. I knew he was close.

I heard Monica behind me squeal and slam in to me as she was overcome with pleasure. Her breathing was fast and heavy as the orgasm took over her At that same moment Jeff exploded into my mouth. I tried to swallow it all but some still leaked out of my lips. The salty goo blasting down my throat had sent me over the edge and I came all over the bed without even touching my dick.

Monica withdrew from my ass and collapsed on the bed next to me. I finally released Jeff's softening cock from my mouth and I rolled over onto my back. He smiled at me and congratulated me on my first blowjob. I simply smiled as my eyes closed and I passed out.