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TITLE: Losing My Virginity To My Best Friend
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LOCATION: Fluent-in-simlish - USA
AGE: 22 - 30
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I was 18 years old when I made the decision to lose my virginity. A freshman in college finally exposed to a world outside my hometown. New people, new experiences, and new realizations about life.

I had always believed sex could wait until marriage, but by fall of freshman year I realized it also didn’t make me a bad person if I didn’t wait. But, I also didn’t want to just lose it to anyone. I knew it would likely hurt, and I knew that it would likely suck. But still, I wanted it to be special.

The only clear choice in my head was my best friend, Steven. We’d been friends all through high school. We were constantly at each others houses — talking, playing video or board games, or just hanging out. Goofy and ADHD, we could banter and mock each other but he offset my studious nature well.

My parents were going to a conference on a warm fall weekend. I lied, saying I was unable to come home, knowing they’d ask Steven to come to town to house sit. They wouldn’t know, nor would he, that I’d arrive the same night as him.

I caught him off guard as I walked through the garage door. The conversation is lost to time of how I explained my presence, but what came next is etched into my memory forever.

“And, actually, I kinda need to talk to you.”

“Oh, ok. What’s up?”

I remember how I hesitated the whole time I talked. I was overcome with a mixture of excitement, anxiousness, and embarrassment.

“Well, I have been thinking a lot these last few months. And…I mean…fuck. How do I say it?”

“With words?” Steven chuckled. “Just spit it out, Lil.”

“I think I’m ready to lose my virginity.” I paused. “And I want you to be my first.”

Steven was silent for a few moments.

“Are you sure? Why me? Also, what?!” He retorted.

“Ok, so look. You’re my best friend, I feel comfortable with you. We’d be learning together unless you managed to keep a secret from me. And likely the only way it would be any kind of special except for maybe waiting until marriage. But I don’t want to just sleep with any guy for the first time. And it’s not like I don’t know you watch porn.”

“I can’t say I’m not honored. Just shocked. But it would be nice not to go blindly into sex.”

I walked over and put my arms around his neck. We leaned in and our lips touched for the first time. He was a better kisser than I’d have imagined and I went weak in his arms. Grabbing his hand, I lead him to my room where we began to kiss deeply. As our tongues danced, I felt his dick growing hard.

Having never done more than kiss, I was unusually aroused. Our hands moved over our bodies and Steven slid his hands under my shirt. I released him to allow him to slide it over my arms. We alternated kissing and undressing each other until all that was left was his tented boxers.

“There’s kind of no turning back now, is there?” Steven asked, my hands resting on the waist band of his boxers.

“I’m fully naked, so not really.”

“Why the hesitation?”

“Outside of graphics in health class, I’ve never seen a cock before. I guess I’m a little…I don’t know…nervous?”

Steven took my hand and slid it through the split in the front of his boxers. I felt his warm, hard cock in my hand and the curiosity returned as I gently touched it. After finally releasing it from its cloth prison, Steven stepped out of them and picked me up to gently put me on the bed.

We touched and explored each other’s now fully exposed bodies. Steven’s hand quickly found its way to my thighs and began to gently tease the wetness that grew between. I became overwhelmed by gasps and moans as his lips left mine and began to kiss down to my breasts where his tongue teased my hardened nipples. I began to gently stroke and feel his dick.

Although I tried to tease him, the mounting pleasure made my hand release him. My body started tensing and I lost all control over it. My hips bucked into his hand as he rubbed my clit faster until I experienced my first orgasm.

I barely had time to comprehend what happened before he was kissing down my stomach until I felt his breath tickling me. As he began to use his tongue on me, my body became filled with electricity.

“Holy shit! Where…where…where did…you learn this?”

He removed his head, using his fingers to tease me.

“So…I may have a thing for women getting off. Yes, I watch porn. But mostly solo stuff or what they call porn for women. I just really find a woman cumming hot. So, I guess it’s a mix of what I’ve seen and what seems right?”

Immediately his face was buried between my legs again. He wrapped his arms around my thighs which were over his shoulders. I found my self writhing and near screaming from ecstasy even before the waves of orgasm took me.

Steven slid over top of me after his tongue brought me over the edge. He was gently kissing my head and neck as I felt his hardness pressing against me.

“So…” he whispered in my ear. “Now it’s my turn to be anxious. One, I don’t have protection. Two, guys don’t often last too long before cumming their first time.”

“It’s ok, hun. I honestly kind of want the real thing my first time I think. I can get plan b tomorrow if I need to.”

“Or I could try to pull out?”

“Pull out?”

“Pull it out before I come and finish elsewhere.”

“No, it’s ok.” I told him with a kiss. “Do it inside me. I want to experience it all.”

Surprisingly encouraged by his honesty, I grabbed him and positioned his cock at my entrance and shifted my hips.

“Well, if it all will fit.” I said to him with a smirk.

Steven slowly began to enter me. For the first time, I felt my lower lips parted by a hard cock. As he filled my pussy with it, my body slowly adjusted to the new feelings. His movements were slow and deliberate, helping to ease the pain. As whimpers turned to moans, he began to push into me faster. My hips began to meet his, creating a steady rhythm that had me shouting with pleasure.

My tight pussy enveloped his cock with each push into me. I could feel the flare of his tip and the twitches as he worked to hold back his cum. Steven began to softly moan and picked up his pace.

“I’m gonna cum, Lil. Are you sure you want it inside?” He panted out.

“Yes!” I shouted unintentionally due to the pleasure felt in my whole body. “Please cum inside me. Please, I’m ready for it.” I begged.

With a final twist, I felt the first shot come out deep inside me. His thrusts began to slow as my pussy milked his cock of his warm seed. He lasted longer than I thought from what he said, but would later learn just how long sex could last.

We used that whole weekend to explore and learn. I’d end up giving my first hand and blow jobs, and what makes sex amazing for me. Though we’ve fucked countless times since, and I’ve been with others, I’ll never forget that night at 18 years old. And still get wet thinking about it.

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