Seth and I were approaching our third month anniversary and my ass was so sore from the poundings it was getting daily. In case you missed my last story, "Losing My Anal Virginity," I was sixteen and under a lot of pressure to have sex with my sexy boyfriend. After a month of dating, I compromised and finally let him fuck my ass. I wasn't a prude but was saving my pussy for love.

Seth was tall, almost six-feet, half Asian and White, and so sexy. He was also a junior and I was a sophomore, so I knew I had to compete with more experienced girls. And he wasn't a virgin when we started dating, which added to my anxiety about giving it up. Seth had become obsessed with fucking my ass ever since I had opened up for him two months prior and my poor little hole was so sore! I would often sit in my school desk sideways to relieve the pressure and often cried at the start of anal with him because it was so raw.

Was I in love with Seth? I wasn't really sure. I knew I liked him a lot and didn't want to lose him, so I had made up my mind that I would give myself until our third month anniversary to give up my vaginal virginity. I was so scared and nervous when I went to Planned Parenthood in secret to get birth control. I knew the pills would take a week to really work, but I started a month before just to be on the safe side. I didn't tell Seth because I knew the second he heard I was on the pill, he would be begging to fuck my pussy... more than he already was.

When we did anal for the first time, we had planned it out and picked a night when my parents would not be home. I was hoping for a similar level of planning this time, too, but I wasn't so lucky. One night while hanging out in Seth's basement, my purse tipped over and my pack of birth control spilled out. Seth reached down to grab it, looking confused.

"Kendall... what's this?" My heart started to race. We had been making out on his grungy basement couch, the smell of mold in the air. Moments before, he had been dry humping me and I knew his dick was already hard.

"I was going to surprise you on our three-month anniversary." My face was beet red, my heart was racing. Seth's jaw dropped as he dropped the pills on the floor and got back on top of me. He returned to kissing me, sucking hard on my bottom lip, pressing his boner into the space between my legs.

"I don't want to wait anymore," he said deeply between kisses. His big hands lifted my t-shirt above my breasts, groping them through my bra. "Let me fuck it, baby."

I didn't say anything but laid beneath him. His warm breath all over my face as his hands tugged the cups of my bra down, releasing my 32c breasts and pinching my nipples. I sat up and took my shirt all the way off, reaching behind to unhook my bra and dropping it onto the dirty basement floor. Seth kissed down my neck and began sucking my tits. I rubbed his back through his shirt, working the fabric up and grabbing the hem, lifting it over Seth's head. His smooth chest had a few hairs in the center and around his nipples. He leaned back up to kiss me and I rubbed his chest as he dry humped me again.

"What if your parents hear?" I asked.

"They know I have sex," he responded with no shame.

"They do?" My parents would kill me if they knew, why were Seth's parents so chill about it?

"Yeah, they caught me and Amber." Just what every girl wants to hear right before losing their virginity, the name of your man's ex. The one he lost his virginity to. Ugh! With jealous images of Seth fucking her now racing through my mind, he began to unbutton my shorts, peeling them off my legs. He wasted no time peeling my cotton panties off either, getting down between my legs and spreading my bald kitty apart.

Seth's slimy tongue began licking up and down the length of my slit, from my clitoris down to my opening and back again. I was still picturing him with Amber as he stimulated my virgin pussy, making it warm, tingly, and wet. He also worked his index finger in, slipping it under my hymen and slowly massaging it in and out as his tongue focused exclusively on my clit.

My breathing now heavy, I tried to keep quiet to not let his parents hear. Seth was coming so close to bringing me to an orgasm and I could feel my ass beginning to quiver, with painful anticipation of the anal sex that was not about to come. Seth's hands reached up to rub my nipples and I began to lose it, my legs shaking, my back arching. I covered my mouth and moaned into my hand, trying to muffle the sound as my little puss gripped Seth's finger tightly, oozing my juice around it. Seth looked up at me with a villainous smile, slowly sliding his finger out and standing up to drop his pants and boxers.

Seth's six-inch dick was beautiful, not too thick or veiny. His little black hairs lead from his naval down to his trimmed pubes. He typically liked me to suck his dick a little before he fucked my ass and on subsequent bangings, he would continue that tradition with my pussy. But today, he was too impatient to wait. He was like a seven-year-old on Christmas morning, unwilling to wait for his parents to get the camera ready before he tore open his presents.

Getting back on his knees between my legs, Seth angled the head of his rock hard cock against my vagina and began to push it in. I squirmed and winced as his eyes, full of lust, met mine and then averted to my tits. He had done this before and wasn't trying to hurt me, but also knew that you had to push past the pain in the beginning before you could get to the pleasure.

"You're so tight, baby. Relax your pussy," he whispered, as if this was something I could easily do.

It felt like Seth had been pushing his dick into my pussy forever, but in reality, it was probably less than two minutes before his pubes were starting to tickle my labia. I calmed down a little, knowing he couldn't get any deeper than he currently was. His beautiful brown eyes now met mine, which had shed a few tears. He leaned in, kissed me, and whispered in my ear.

"God, you're tight. You're so fucking amazing, Kendall!" Sucking on my neck, Seth put his weight on me and began rocking his dick out and in slowly, moaning and grunting. "Fuck!" His cock began to tense up inside me and he stopped moving as he began to moan.

"Are you cumming inside me?" I asked, shocked that this was happening already.

"Shhhh! Stay still," he commanded as he breathed heavily right in my face, his warm breath a little sour. After about thirty seconds, he relaxed. "Sorry, you're just so tight. I couldn't help it." He lifted off me as he slowly slid his dick out, bending my legs up to watch as his cum oozed out of me, mixed with a little blood. Seth grabbed some Kleenex and wiped up my messy puss to avoid getting it on the couch.

I relaxed, laying naked on the dirty basement couch and thinking about the way I had planned this to go, which was nothing like the reality. I had envisioned being in my room and a lot more romance leading up to it. A dinner date, maybe a movie, whispering to Seth that I was ready and tonight was the night, and cuddling all night in my empty house while my parents were out on a date or something. Instead, I had just lost it in his gross basement, his parents right upstairs, and my parents expecting me home in an hour.

"Are you okay?" Seth asked as he watched me stare at his water stained basement ceiling. I nodded my head yes as he leaned in to kiss my cheek, his sticky dick still hard and resting on my pelvis. "Let me try again," he said softly as he angled his dick back against my pussy and pushed back in before I could respond. My hands grabbed onto his shoulders hard and let out an uncontrollable pained grunt as he slid back inside me, deep.

"Fuck yeah," Seth moaned as he picked up speed, fucking my sore, tight pussy harder than before. He winced as my nails dug into his back. I didn't mean to cause him pain, but he stopped and pulled out, backing away and rubbing his shoulders.

"Get on your knees," he asked me and I sat up and crawled around to face the bookcase on the far side of his basement. It was full of family photo albums as Seth grabbed my hips and positioned his dick back into my pussy from behind. I was so used to being fucked in the ass like this, but the curvature of his cock in my pussy the other way felt so different. "Fuck yes," he moaned as his hands grabbed my shoulders and he began to pound me.

"Owwwwww," I cried softly as Seth banged my raw pussy from behind. His cock was rubbing my g-spot when I was on my back, but now he was hitting a different spot. Google would later reveal that this is my o-spot, but I was only familiar with my clit and g-spot that night. I began to moan as he stimulated it, his balls slapping against my clit as he thrusted in and out of me. His hands reached around my chest and cupped my breasts, pinching my nipples. This began to set me off.

"OHHHH GOOOOD!" I screamed, forgetting to keep quiet as my pussy began to quiver. Seth's thrusts slowed down, largely because my pussy grew so tight around his dick that he couldn't move too much. He began to moan, too, slapping my ass as his cock began to twitch inside me.

"Oh fuck, are you cumming?..." My eyes were rolling back, my jaw dropped, I couldn't speak. "Fuck, I'm cumming!" Seth blasted his second load deep inside me as my juices dripped down his balls and beadlets dripped off my clit onto the couch. Seth slowly pulled out and grabbed another Kleenex, wiping the juice and jizz that oozed out of my pussy.

We cuddled for a few minutes before we got dressed. My parents were expecting me home and I didn't want them to suspect anything like what just happened. As we got to the top of the stairs and opened the door, Seth's parents were at the kitchen table. I could tell they heard my screams and must have known that we just fucked.

"Would you like to stay for dinner?" Seth's mom asked me, not really making eye contact. I tried not to look too embarrassed.

"No thanks, Ms. Dano. My parents need me home tonight." I kissed Seth on the cheek and got out of there fast. After dinner with my parents, I should have studied for my geometry test. But instead, I took a bath. I kept spotting and felt dirty and was hoping a relaxing bath would help. Seth and I resumed anal sex for the next few days because my vagina was so sore and tender. But over time, I got used to having my pussy fucked and then Seth had to beg or do really amazing boyfriend things to get me to open my ass for him again.

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I hope you liked this reflection on the time I lost my virginity. I'm planning to write more soon, some real stories of things that have happened to me as well as some fantasies of mine. If you liked it, be sure to let me know. : )

xoxo

Kendall