It was about halfway into the summer before senior year. Evan and I had been very sexually active throughout the year, and into the summer.
Most of the time we would do oral, but from time to time I would let him fuck me in the ass. I enjoyed anal, but not very much. It seemed that the more often I did it the less it hurt, but the less pleasure I felt. The less often, the more pain and more pleasure. If we did it too often, I wouldn’t even be able to get off. I tried to keep it at a fairly regular interval, and it was about time we did it again.
Evan came over right after my parents left for work. The night before I had sent him a picture taken through a mirror of me on all fours. He had a clear shot of my ass, and a finger in my vagina. I sent these to him mostly when I was inviting him over for anal. “Come over here tomorrow to get a piece of this ass” I sent with it.
When I let him in, we went straight to my room. My step-brother Alex was still asleep, but I didn’t want him to walk in on us in the living room. He had walked in on us before when I was riding Evan’s face, and that was pretty awkward. I didn’t want that to happen with me taking it in the ass.
We made out for a short period of time, but eventually got straight down to business. Before too long we were 69ing. I was on top of him, licking his cock while he ate me out.
I licked swirls around his head before I eventually plunged it in. I bobbed on his dick, letting it go all the way down to my throat, then almost all the way out. I let out a moan with every exhale, while I used one hand to play with his balls.
After a few minutes, I felt his dick throb a little, and knew what was coming. I prepared myself for the shot.
His cum filled my mouth. I could easily take it all without losing any, but he liked it when I made a mess. I let about half of his cum drop down his shaft and onto his balls.
I continued to suck his dick as he came in my mouth; his licking intensified and he firmly grabbed both of my asscheeks. When he was done coming, I made sure to get the last bit of his cum so there wasn’t a mess. Then I got up, and rode his face, enjoying his mouth magic.
After a several minutes of riding his face, I noticed he was hard again. Thoughts began running through my head. I was close to coming, but I wanted to stop.
“What’s wrong?” He asked as I started to get off of him.
“I want to have sex.”
“Like, real sex? I don’t have a condom.”
Monica had told me that birth control alone was safe enough, but I didn’t like the thought of him coming in me. She always got creampied when she had sex, but the thought of me doing it gave me anxiety.
“Just pull out and I’ll suck it, or if its bloody cum on my face or something?” I said finally as I shifted around him so I was next to his dick, in the cowgirl position. I grabbed it as I lifted myself over it and put the tip in between my labia. It brushed past my clit and gave me a pleasurable little tingle. When it was right at my hole, I began to slowly lower myself onto him.
It hurt a little at first, but felt really good as his dick stretched out the walls of my vagina. When I got it all the way inside of me, is when it really hurt. I sat there for a moment to get over the pain of my hymen breaking. As it faded, I began to rock my hips on him.
The pleasure was incredible. His cock rubbed up on my g-spot as I rubbed my already sensitive clit on him. I started to go faster and faster, and even lifting myself up and down on him instead of just rocking my hips. He grabbed both of my lightly freckled C-cup tits and squeezed, catching my nipple in between his fingers for a little extra pressure.
My moans were getting louder the longer I road him. I learned forward, supporting myself with my hands on his chest as I was about to cum. Suddenly, it was happening.
My vagina began to pulse as the pleasure shot throughout my body. My head was tingly, and my whole world turned to fuzz. All I could do was let out screams of pleasure. I couldn’t stop myself from bouncing up and down on his dick if I wanted to as my orgasm ran its course.
As it ended, I could barely continue to ride him, and he noticed. He rolled me off of him, and onto my back. He then positioned himself in between my legs, and propped them up onto his shoulders. His cock found it’s way to my still wet vagina, and he slipped it in again.
As he pumped, this new position rocked my world. I let out a scream every time he thrusted it into me. His dick was so much deeper this time. I did like the feeling of being on top, but this allowed him to hit my cervix. It hurt a little, but added a new pleasure that is hard to explain. I loved him this deep inside of me.
He fucked me like this for a good 10 minutes. I was getting close to coming again, but I wouldn’t get to.
“Fuck” he gasped as he pulled out of me. I got up and leaned toward him. His dick had a little bit of blood on it, as I thought, so I wasn’t going to take it in my mouth. He jacked himself off and began to cum.
I closed my eyes, opened my mouth and stuck my tongue out to catch his cum. The first shot hit me in the eyebrow/eyelid. Followed by one to my cheek and two in my mouth. The rest didn’t have as much power behind them and only made it to my tits.
When he was done, I swallowed what had made it into my mouth, opened my good eye and we both laughed. After cleaning up, we cuddled. We had sex another 2 times that day, and numerous times throughout the summer.
Source: reddit.com/r/Erotica/comments/cx44hy/4_losing_my_virginity