I felt bad for my friend Jake, I really did. We had been friends since we were freshmen in high school. Now we were 21, he was very good looking and in the shape of his life. The girls loved him, and he loved to play them. About 3 years ago, Jake had fallen hopelessly in love with this girl, her name was Hannah. Hannah was beautiful, blonde hair that fell to her back, nice chest, the most sparkling blue eyes you'd ever seen and she always smelled like strawberries. She was a cheerleader too. Jake really couldn't have picked a better girl to date.
They always had so much fun together. I knew that there was something different about Hannah, because Jake never seemed to have as much fun with anyone else he was ever with. Jake had sex with almost every hot girl in high school. I watched him pick up so many girls, and like it was clockwork, he'd throw them away. That's why it was so sad to see him like this.
Jake sat on the couch of our apartment moping around like he had been for the past week. He hadn't gone to any classes and he was only eating enough to keep him alive. He sat there on the couch watching the football game and looking more miserable than I'd ever seen a human in my life.
"Are you going to be alright?" I asked him. Jake just stared up at me as if he didn't realize I was even there. "Steph...sorry. I was just really into this game." He said. "It's cool" I said in response. My name was Stephen, but Jake called me Steph. It always made me felt a little weird because it sounded so feminine.
"Are you sure you're going to be ok?" I asked him again. "Yeah...well..I don't know..." he said. "It's just Hannah...I really miss her. I miss her looks, her smell...but I really miss the sex." He said. It totally came out of left field, but he was my friend, so I just let it go. "I understand..." I said. "I really need someone to take to the costume party next week too." He thought out loud. "Do you have a costume picked out?" I asked. "Not really..." He said with a blank stare.
Just then a thought came to mind. Hannah left her old cheerleading uniform for Jake one year before she went on vacation to Europe, a sort of "remember me by" gift. She also left her girly stuff all over our apartment. It had sort of become a running joke with all of our other friends that a girl lived here with us. I was probably small enough to fit into it so I walked to Jake's room and put it on. It's important to know that I'm not gay, honestly, and I've never even thought about cross dressing for fun, but the desperation that I saw on my friend's face made me depressed.
I slid some of Hanna's stockings up my legs then put on her red pleated skirt and grabbed the wig I planned to use for my Halloween costume and put it on. I found one of her bras and stuffed it, then put the top she had left on with it. I found some of her red lipstick in the bathroom and put it on. I walked back up the hall and hid in my room for a second before saying "Hey Jake, someone is here to see you!" I walked into the room he was in and stood with one hand on my hip. I swayed into the room as feminine as I could and sat down next to him.
Jake stared at me the whole time. His mouth was gaping open. "You make a really hot girl, Steph." I looked at him sort of sideways. I rolled my eyes and said "wow, thanks a lot..." I noticed he was smiling. "That's the first time you've smiled in a week!" I said. "No, seriously Steph. You're turning me on." He said to me. He stared at me like he was going to pounce me. "Steph, do you think you could...you know...help me out?" I looked back at him. I was very worried that maybe I had made a mistake. Dumbfounded, I responded...but I already knew the answer, "Help you with what?" I asked. "Could you give me a blowjob?" he asked. "No!" I said right away. The smile had faded from his face. I started feeling bad again
"Look Steph, Hannah didn't have any kind of sex with me for weeks before we broke up. I'm seriously dying here. Please, just do this one thing for me, I promise nobody will ever know. It'll just be a friend doing another friend a favor." He said. I looked at him with a concerned face. My best friend was begging me for help, and I felt terrible saying no to him. "You promise you won't tell anyone about this?" I asked "Yeah man, nobody will ever know" He assured me. "Fine" I said.
As I got on my knees, he spread his. I sat there looking up at him deciding if I really wanted to do this or not. He looked down and said "Thanks a lot, I always knew you were a good friend". I reached out and unbuttoned his pants. I pulled the zipper down. Each link in the zipper sounded like a death toll. I wasn't at all into this, but I wanted to help my friend more than anything. He lifted his hips and I pulled his jeans down. I could see the outline of his dick through his boxers. I pulled his boxers down and his cock came out like a switchblade knife.
I hadn't ever thought about his penis before, but for some reason it was bigger than I expected it to be. I was now staring at the reason for Jacob's popularity with the girls in high school. I reached out cautiously and pulled it towards my face. I didn't have time to stare. Jacob put his hand on the back of my head and pulled my face towards his cock. Instinctively, my mouth opened, and the dick went in.
I tried to think about what girls did when they sucked my dick. I wet my lips as he forced it in and out of my mouth to make sure they were soft. I pulled my lips over my teeth so that he didn't get scratched. My mind was racing a million miles an hour. I felt his cock poking the back of my throat. I was gagging a little bit. Jacob was so aggressive, probably a little sexually arrogant from all the girls that he'd fucked before. I was basically just going to be another "girl" added to his list.
I closed my eyes and relaxed so that I wouldn't choke on his cock. My right hand reached up and grasped his shaft. I started moving my hand with my mouth. Jacob moaned loudly as his cock penetrated deeper into my throat. I got used to the feeling and stopped gagging. "Ohhhh baby...You're so good. You're sooo much better than Hannah ever was." He said to me.
I began to enjoy what I was doing a little. I was only about 10 minutes later that I felt Jacob's grasp on the back of my head tighten the wig. He lurched forward driving his cock down my throat and grunting loudly. I opened my eyes, surprised that I wasn't gagging as his big hard cock was all the way down my throat. I could feel his soft pubic hair on my nose. His dick pulsed enormously 4 times. I only felt his jizz for a second as it went down what was left of my throat and filled my belly. There was so much of it, I could feel it warming me inside. I felt it pulse a few more times and his hold on my head loosened. His dick slid out of my mouth slowly, and completely clean.
His head was arched back over the couch, and he was breathing very heavily. I sat next to him and his breathing slowed. He picked his head up and looked at me. "That...was amazing. Thank you so much." He said. He smiled at me, and I smiled back. I got up and went into my room.
I tried to forget about what had just happened as I took off Hannah's clothes. I had just given my best friend a blowjob, maybe the best blowjob he'd ever had. Not only that, but I swallowed his cum. As I sat there digesting his semen, I thought things might be different now. Would we be closer friends, or would we not? But I knew that from now on, Jacob was a part of me forever, whether I liked it or not.