I started dating Evan 2 weeks into Junior year. He was tall, athletic, confident, and funny. He had blue eyes and medium-short, dirty blonde hair that stuck up in the front with no gel in it. He had abs and defined muscles because he worked out a lot. He was a receiver on the varsity football team, which was fairly impressive as he was a sophomore. He tried to be friends, or at least friendly with everybody.
It didn’t take long for our relationship to get sexual. He had a truck, and would drive me home every day after his football practice and my soccer practice were over. Often times I would blow him on the ride home. Thursday nights my parents would not get home from work until after 10 (they both worked at the same company), and those nights we would get a little wild.
We would get in whatever position he felt like that day and I would let him throat fuck me. He gave me a few facials, and came on other parts of my body but primarily liked finishing in my mouth. He would also eat me out. I loved sitting on his face, and would get really loud sometimes. I didn’t really worry about Alex hearing us because he made good use of his Thursdays as well.
It seemed like every few months that year, Alex had a different girlfriend. Each one of them was in his room every Thursday screaming in pleasure as he drilled into them. It actually made Evan a little jealous since I was still a virgin and didn’t want to have sex.
I had been on birth control for a few years at this point since my periods were extremely painful. The thought of having sex still made me nervous because I didn’t want to get pregnant. I had plans to go to college and couldn’t do that with a kid.
Our 6 month anniversary was approaching, and I had an idea to compromise and let him fuck me without risking pregnancy. It landed on the weekend, but we decided to celebrate it the previous Thursday. That day, we both skipped practice.
When we got home, we were alone. Alex was at practice, and our parents wouldn’t be home until after 10. We started with the mushy stuff.
“I got you something” Evan said as he handed me a small jewelry box. Inside was a silver necklace with a hummingbird on it. It was a cheap Hallmark necklace, probably from Walmart, but I didn’t care about what it cost or where it came from.
“I love it!” I said sincerely with watery eyes. I took it out to have him put it on me. “Thank you” I said as I embraced him.
We kissed for about a minute, then I broke it off. “I also got you something,” I said as I pulled out a mostly full dasani water bottle.
“What is it?”
“Well, I had to put it in a water bottle to hide what it really is from my parents. I’m still not ready for sex, but I thought that anal would suffice. I can’t get pregnant from that, so I got some lube to try it.
His face lit up, “I can work with that” he said excitedly.
I closed and locked the door, and started to kiss him. He took my clothes off, and I took his off until we were completely naked, on my bed. I worked my way down on him, and put his dick in my mouth. I sucked on it for a few minutes. I was hoping if I got him closer to coming I wouldn’t have to take his dick in my ass as long.
I took it out of my mouth and handed him the lube from my nightstand. “Start with a finger or two, and go slow.”
I got on all fours and let him finger my asshole. It was a weird feeling, but it wasnt painful. “Okay, I’m ready for your dick,” I told him after a minute or so. He put some lube on it and pressed his head against my asshole. It slid in pretty easily.
His dick wasn’t huge, but it wasn’t the smallest I’ve ever seen either. It was about 7″ long. When he put it in is when it started to be slightly painful. He started with slow, shallow pumps. The more he did it, the deeper he went. As he was going, the pain was pretty consistant; I was getting looser, but at the same time he was going deeper each pump.
With each pump, I let out a soft, slightly pained grunt. Eventually he got it all the way inside my ass and held it there. After a few seconds he started going again, ever so slowly picking up speed. The pain never went away, and the feeling resembled that of taking a big shit (yes, girls poop too) but there was something else there. I was horny, and felt some pleasure in it too.
As he sped up, my grunts turned into moans, I was enjoying this more the faster he went. I supported myself with one arm as the other reached back to my bald pussy.
I began to rub my clit while he was fucking my asshole. My moans started to get really loud. My messing with myself really made him pick up the pace.
“Oooh fuuuuuck!!” I yelled as I realized I was about to cum. I was about 60% there, then out of nowhere hit 99%. I buried my face in my pillow and screamed in ecstacy as lightning shot through my body from my asshole and clit to my head, and back. I had never cum like this before. For every breath of mine, he drilled my ass with several pumps, and I let out a shriek that must have gotten him to that point as well.
At the end of my orgasm, he began to cum. “Fuuck!” He let out under he breath as he began to cum. I felt my asshole start to fill up with jizz. He kept going for a while, his hot cum acted as a fresh lubricant inside my asshole.
After he finished, he slid out and laid next to me for a little bit. “Damn,” he said in between breaths.
When I got up to wash myself out, I could barely walk. My asshole was sore for the next few days after that.
Source: reddit.com/r/Erotica/comments/cwttau/first_time_anal_mf
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