This all started when I was 19. I had the biggest crush on my brother's friend, Jay. He would come by our house about 3-4 times a week and play basketball with my brother and a few other friends. Every time he came around, I would do my best to make him notice me, but he never looked my way.
One night my brother and Jay were playing video games and having some beers. I wore some loose fitting sweatshorts and a tight tank top with no bra and came out of my room and asked my brother if I could join since I was bored out of my mind. Of course he said no, but to my surprise, Jay said "Just let her play!" I had no idea what I was doing, but I was having fun laughing and trying my best to flirt with Jay. Then Jay offered me a beer. I've had vodka before, but never beer, but I wanted to be cool so I said yes. It took everything out of me to drink it, I gagged at every sip.
We played for a couple hours when my brother and Jay decided to call it quits. My brother went to bed and Jay gave me a hug goodbye, something he'd never done before. I was pretty bummed that the night had ended early.
I got ready for bed and went into my room and turned off the lights. A couple of minutes later, I heard a very faint knock on my bedroom window. It scared the crap out of me, but for some reason, I knew it was Jay. I opened the window and let him in. "I'm too drunk to go home, can I just hang out with you until I sober up," he said. Of course I said yes. We talked quietly in my bed….. my brothers room was right next door and Jay didn't want him to know he was in his my room. We started talking about random things when he was complaining about his back hurting. I offered to give him a massage, but in reality, I just wanted to get his shirt off. I grabbed some lotion and massaged away. I had no idea what I was doing, but I was trying my best. "You better give me a massage after," I said. He chuckled and said "Don't worry, I will."
10 minutes later he got up and sat down next to me and said thank you. Then leaned in and kissed me. I couldn't believe what was happening. My heart was beating so fast. I immediately took my shirt off and we started making out. Jay's hands were all over my body and I was loving every minute of it. His right hand reached into my pants and I moaned in his ear when he felt how wet I was. He laid me down on my bed and I lifted my butt in the air and arched my back so he could take my shorts and panties off. He kissed the inside of one of my thighs and worked his way up and then back down my other thigh. Then next thing I felt was a slight lick on my clit. I was in heaven. It was the first time someone had ever eaten me out and it was everything I hoped it would be like. I came in 5 minutes. I wanted to return the favor and unbuttoned his pants. His dick was rock hard. It wasn't that big and I remember thinking "I could take this." I licked it up and down and remembered to look up at him to gauge what felt good. I wanted to give him the best blowjob of his life. "Put it in your mouth baby" Jay said. In one swift move I shoved his whole cock in my mouth. He let out a deep breath and I could tell he wanted to moan loudly. Every 20 seconds or so he would pull his cock out of my mouth and then I would go right back and suck some more. I knew he was going to cum any minute. "Do you have a condom?" he said. I didn't, but I knew my parents had some.
I put my shorts back on and told Jay to hide under the blankets. I snuck into my parent's bathroom and grabbed the condom box and returned. I closed the door and pulled the covers off of him. He was still rock hard. I gave him the condoms and he took one out. My heart was racing. "I'm a virgin Jay," I told him. "Don't worry Kate, Ill be really gentle with you," he said. With those words, I was calmed and my nerves went away. He pulled the condom over his dick and laid me down on my back, gently kissing my neck and working his way down to my tits. He was in between my legs and guided the tip of his dick into me. I let out a slight moan… at first it hurt, but the deeper he got, the better it felt. "You're so fucking sexy, I've wanted to fuck you for years," he said. "Me too…. fuck me" I replied. He was being so gentle with me and I loved that he took it slow, but wanted him to go faster. "Faster," I screamed. I remember his eyes got wide when he heard me say that and next thing I knew, he was pumping me hard and fast. He pulled out and took the condom off and came all over my stomach.
He grabbed some tissue and cleaned me up and started putting on his clothes. I got dressed and we stood up. He gave me a passionate kiss and told me thank you. "We should do this again sometime," I said. Then he jumped out the window.
Source: reddit.com/r/gonewildstories/comments/3xt5e7/my_first_time_with_my_brothers_friend
you should be more consistent about the fact that you were keeping quiet.
>"I’m a virgin, Jay" I said. "Don’t worry, Kate", he said. the names really took me outta the story.
Sounds like a good first time, thanks for sharing and hope he got you again and again!