It had been a week since I had my virginity stolen by Brad after his senior prom. Now that I was sixteen and had already cheated on my boyfriend Steve, I decided it was time to finally have sex with him. We had been going out for a few months and he'd been begging since about the first week, so it only felt right. Of course, we'd been doing oral stuff since we first started dating. I waited until Wednesday to tell him because I was still feeling the pain in my vagina from the first time.

"I'm ready," I whispered in his ear at school. He had soccer practice all week so I knew we wouldn't really be together to do it until the weekend.

"You're ready?... Ready for what?" He looked puzzled, his eyebrows raised above his soft blue eyes. Steve was tall and skinny with blonde hair and an athletic body, but not buff.

"For it," I smirked. I don't know why, I couldn't bring myself to say what it is without smiling. A big grin came across his face.

"My parents will be out on Saturday night. I'll buy some condoms. What time you coming over?"

"6:00." We parted and went our separate ways, kissing and smiling at each other each time we passed in the halls. And he started sending me dick pics on Snapchat leading up to it with captions that said things like "U sure ur ready?" I was ready, but I was also nervous. Steve had seen my vagina before and I let him finger it. He knew I still had my hymen, but now I didn't. And I was also living in fear that Brad would do something stupid and brag about what we did that night. But I was mostly just excited to find out what it would be like with Steve.

I spent all day Saturday with knots in my stomach. I barely ate and around 5:00, I got in the shower and made sure I was clean and fresh. I put on a little makeup and did my hair, dressing in a nice sun dress and heels. I wanted to look great for Steve.

When I got to his house, he was waiting for me at the door. He dressed nice, too, wearing a button down shirt and khakis. I walked in and he embraced me, kissing me passionately as he gently pressed me up against the wall. Then he kissed down my neck to my shoulders. Compared to Brad's gruff face, Steve's was very smooth as he unzipped the back of my dress and slid it off my shoulders, dropping it to the floor. He admired my body as he picked me up and began to carry my upstairs. I wrapped my arms around his shoulders and stared into his sexy face as he took me up to his bedroom, which was navy blue with a plaid bedspread and posters of his favorite rock bands on the walls.

As Steve gently lay me on his bed, he climbed on top of me and kissed me more before moving down to my chest. He reached behind my back to unhook my bra as he peeled it off and gently groped and sucked on my breasts. Steve loved my boobs and could barely make it through a minute of making out before he needed to at least hold them if not let them out to play. But usually I didn't let him go much further. I was filled with a different sense of anticipation knowing that today, his lips on my tits was just the beginning. I moaned softly as I spread my legs and wrapped them around his waist. He gently leaned in, pressing his hips into mine and I could feel it, his boner in his pants pressed between my legs. I thrust my hips up into his and without missing a beat, he jolted up and began taking off his shirt.

Steve's smooth, hairless chest was so lily white that it almost reflected the sun coming in through his window. He stepped off the bed to drop his pants and boxers. While Steve was blonde, his pubes were closer to red. He reached for his nightstand and pulled out a condom, but hesitated and set it down instead. He climbed back on the bed and held under my knees, lifting them up to my chest. He gave me a seductive look before leaning in to lick my clitoris as he gently fingered me. I was nervous as he stopped and looked closely at my vagina, then looked at me.

"Did your hymen break?" Fuck! I was hoping he wouldn't notice.

"Oh... yeah. It was an accident." I tried to not let on that I was lying to him.

"How do you break it by accident?" A solid follow up question.

Think quickly, Jackie!

"I was masturbating, trying to make myself ready for today. I accidentally broke it with my fingers."

Steve's face made an "O" as he clearly thought that was really hot. "I wish you would have let me watch." He leaned in to kiss me as he fingered me more, getting me good and wet. His kisses had become wild and sloppy, covering my chin with his spit and as he moved to suck on my left nipple, I found myself approaching an orgasm. Not my first ever, but my first with Steve and it definitely topped the one I had with Brad. As I came on Steve's fingers, he returned to kissing my lips, thrusting his tongue in my throat. We were both ready.

Steve reached for the nightstand, straining to grab the condom as he ripped open the package and took one out. The disgusting aroma of the rubber and spermicide filled the air. He remembered his health class lesson as he pinched the tip and rolled it on his erect cock. He got on his knees between my spread legs and angled his hips to put his head against my hole as he slowly began to push in. I didn't think it would hurt since I'd already gotten over the pain of Brad's dick and Steve wasn't as wide, but here I was wincing again as Steve spread me open.

"Oh fuck, you feel so amazing Jackie!" Steve's face looked full of pleasure as mine contorted in pain. Unlike Brad, Steve didn't stop to ask if I was okay, he just continued to fuck me slowly and gently. I watched him turn slightly red and start to shake as his voice got lower and he repeated the words "Oh fuck" as he quickly began to cum. I had a moment of disbelief. He was cumming already? As his orgasm stopped, he pulled out and slipped the condom off. I looked at it with disgust. Cum had never looked more unappealing than inside a used condom.

Steve laid on top of me, his warm hard cock pressed against my leg as the last drops of cum oozed onto my skin and he kissed me wildy. "You were amazing, baby!" I thought for a moment about how I should reply. Steve had not been amazing, but I didn't want to hurt his feelings.

"It was so hot watching you fuck me." It was the nicest thing I could say.

"You're so fucking hot, I could fuck you over and over, baby." My eyebrows raised up. I really wanted to get off, too.

"You want to go again?" I asked and Steve grinned. "Get on your back," I told him as I rolled over to grab another condom. I handed it to Steve, not trusting myself to put it on correctly as he covered his still erect dick with another one.

I climbed on top of him and his hands instantly rested on my hips as I angled my pussy against his dick and slowly slid down onto it. Now that I was in control, there was far less pain. I slowly began to ride Steve, finding the angle and spots deep inside me where I got the most pleasure. I took it deep, finding my g-spot as I started to moan. Steve began to thrust up into me and I cupped my boobs to stop them from bouncing too hard as we fucked each other.

I was getting close to orgasm as I pinched my nipples and enjoyed the mix of me riding Steve and him thrusting up into me. But I could also tell that Steve wasn't going to last much longer. I let go of my right breast and put my hand above my vagina, rubbing my clit in circles as I watched Steve's jaw drop. I began to cum hard on him, my juices running down his cock into his pubes as he began to moan. The instant my cum leaked down his dick, he began to moan hard as he came a second time. I remained seated on his cock, feeling it pulse as he blasted his cum inside the condom.

I slid of Steve's dick and laid on top of him, my breasts squeezed against his chest as I kissed him. "Thank you, baby. You were wonderful."

"I love you, Jackie." This was the first time he'd ever said that to me.

"I love you, too, Steve." This felt wonderful. This moment made up for the mistake I made with Brad...

... Little did I know that mistake would come back to haunt me eventually...