Turtlegeek Loses His V-Plates

Prologue: This is a prequel to my story "Taking Her Virginity." In this story, I describe how I lost my virginity! Although all names have been changed, this is a true story.

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My junior year in high school had just finished. With the summer ahead, I didn't anticipate much excitement in the next few months of holiday. Little did I know that by the end of the summer, my life would be rocked!

A bit of background on me... I was the typical geek, lanky, 5'10", having just turned 18. Being so shy and not very confident around girls, I had immersed myself in scholastic activities, hobbies and playing computing games. Although I had gone on a few dates, nothing really went further (much to my dismay).

My older brother Mike had just finished his sophomore year at university and was home for the summer. He and I have always been close and it was great to catch up with him. He had joined a fraternity in his freshman year. Here is where my story starts.

"It's great to catch up with you, bro! What have you been up to this past year!?" asked Mike, as we were lounging about the living room.

"Not much," I said glumly. Truth be told, I was actually doing quite well in academic matters. However, my nonexistent social life was always on my mind and it was quite frustrating.

"Well, mom says you're doing great at school." Mike then changed the topic. "How are the girls at school!? I bet you're having a great time with them," as Mike grinned at me. I thought to myself how much more self-confident Mike had become since he started university.

"Nope. You know, Mike... we're pretty close and I want to tell you something. Um... I'm still a virgin! Can you believe that?! I just turned 18 and I still haven't gotten laid!" I don't know if I was looking for comforting words from Mike or if I was asking for his advice indirectly. Mike looked at me thoughtfully and carefully chose his next few words.

"You know... it happens differently for each person. When the time is right, you'll know it!" I could tell that Mike was trying to cheer me up. He quickly changed topic and we made small talk for awhile longer. Later that night, we all went out as a family and everybody caught up with each other.

The summer drew on and I fell into my normal routine of geekery, mainly playing computer games and hanging out. Mike was out of the house often, running around and catching up with local friends, etc. As the summer drew to a close, Mike got ready to go back to begin his new semester.

"Hey, bro! It's been great seeing you this summer. You know that I'm getting ready to go back to school soon, right?"

"Yep. I'll miss you," I said. This wasn't a lie.

"Me too. Anyways, my frat always has a big party at the start of the new semester. It'll happen in a month or so. Why don't you come as my guest!? You'll have a great time!" Mike gave me a huge grin and slap on the shoulder.

"Thanks for the invite, but it would be so awkward for me. I wouldn't even know anybody there."

"Don't be silly. We know each other! Plus, I can introduce to my girlfriend Kristy. She'll also have some of her friends at the party and you can meet them too! What do you say, bro!?"

"Well... um..."

"I PROMISE that you'll have a great time!" Mike seemed very sincere and confident in his sentiments.

"OK," I say reluctantly.

A month later, I find myself at the frat party. I see Mike coming over to me with a cup in one hand, and his other arm wrapped around a girl. She must be his girlfriend Kristy. A thin pretty blond, great figure and confident walk, I understood why Mike would be attracted to her.

"Hey, bro! Glad you made it out to the party! Here, have a drink." I take a sip of the sweet concoction... clearly, spiked with alcohol. "This is my girlfriend, Kristy." Mike gives her a quick peck on the lips.

"We finally meet! Mike has told me a lot about you." Kristy gives me a cute smile. I sort of blush.

"Hopefully, good things" I say, trying not to sound awkward. After a bit more small talk, we start to mingle with a few other people. I did get introduced to one of Kristy's friends, Jen. She was a brunette, medium-sized, and had a great figure with a funny personality. I found it very easy to talk with her! During the party, I was careful only to have that first (and only) cup of alcohol. I didn't want to end up piss-drunk and making a fool of myself. As the party continued further into the night, the alcohol continued to flow freely. Mike came up to me, staggering slightly. Kristy was nowhere in sight.

"How are you enjoying the party, bro!?" At this point, Mike was a bit hammered.

"It's cool, I guess."

"Say, I have something for you in my room... upstairs, first room on the left. Here's the key. Meet me there." Mike is grinning and I cannot tell if it's because of the alcohol or something else. Curious, I walk upstairs, unlock his room door and enter. I'm startled to see Kristy there. She is naked on Mike's bed with her legs splayed open.

"Shit, I'm sorry! Mike told me to come up to his room and I... um..." I must have looked like a deer in the headlights.

"It's OK. Come in, close the door and sit next me." Kristy's voice is soothing. I must have been beet-red as I slowly walk towards her. As I get closer, I can see that her body is flush red. Her pussy lips are swollen and very moist. It's clear that she's been pleasuring herself.

"Mike's told me about your little problem." Kristy says to me, seductively. I can smell the alcohol on her breath.

"What problem is that?" I ask innocently.

"Your virginity," says Kristy as she licks her lips and looks straight into my eyes.

"Um... what of it?" I retort defensively.

"Let's take care of that. We don't have much time!" says Kristy. She pulls me to her and starts to kiss me. Of course, this is all unexpected and I'm almost in shell-shock. I think to myself. This must be Mike's surprise for me. He set this all up with his girlfriend! Although I'm completely inexperienced, I just go with the flow. As Kristy and I continue to make out, all my clothes came off rather quickly. I didn't know anything about foreplay at the time, but Kristy's cunt was already very wet when I first entered the room. At this point, I was as hard as a rock. "Time's a' wasting! I'm on the pill and I'm clean. Let's hook up!" exclaimed Kristy. I was shocked by her boldness.

I quickly mount her (missionary position) and the head of my cock is at the entrance of her cunt. I'm thinking to myself...I'm finally going to get laid! As I kiss Kristy deeply, I start to enter her pussy. The feeling cannot be described! Although her cunt was not that tight (as she probably wasn't a virgin), it felt great to me. Animal instincts take over and I started to fuck Kristy really hard and deep. I'm jackhammering her. I was balls-deep in her pussy and I remember shaking as I nutted violently into her. It felt like a ton of cum erupted from my cock as I emptied myself into Kristy's cunt. Mission accomplished! As for her, she didn't experience an orgasm. She probably punched my v-card, as a favor to Mike.

The entire fuck session (from making out to cumming in Kristy) was very quick. I would say it took about 5 minutes. She quickly pushed me off of her. I smiled breathlessly and said "Fuck, that was awesome! Thanks!"

Kristy responded sarcastically, "Yes, that's what you just did! You fucked me!" She then grinned mischievously at me. With no more small talk, we both got out of bed. I notice a ton of cum oozing out of Kristy's cunt as she puts on her panties. I smile to myself. We both quickly get dressed.

Just then, the door opened. Mike and Kristy's friend Jen walks in. Mike is carrying a bottle of alcohol, some cups and a condom.

"Oh, that's where you are, Kristy. I've been looking all over for you." says Mike.

"Hey Mike, thanks for setting me..." I start to say. Kristy quickly interrupts me.

"Your brother and I were just chit-chatting a bit. He's a great guy." Kristy says to Mike.

For an instant, I'm saying to myself "WTF!? Didn't Mike arrange for me to fuck his girlfriend Kristy?" Then, it dawns on me that Mike DIDN'T plan the fuck session and didn't know anything about it! it was Kristy's idea! That's why Kristy was in such a rush. Having realized this, I'm speechless.

"Here's your surprise, bro! You've already met Jen earlier tonight. She wants to get to know you better, if you catch my drift. Here's some rum to get things going. Kristy and I will leave the two of you now. Have fun!" With that, Kristy walks towards the door. She turns and winks at me. The door closes and I don't see Mike or Kristy for the rest of the night.

What happens next is blurred, in terms of memory. I remember drinking quite a bit of the rum with Jen, talking and laughing, and then making out. After that, I don't remember much. I must have blacked-out. I woke up the next morning with a hangover. I'm in Mike's bed and naked. I look over and see a very naked Jen, sleeping peacefully next to me. She starts to stir and opens her eyes.

"Hey, cutie! I had a great time." she says, as she cuddles with me.

"Did we, umm..., you know?" I asked innocently. As I said, there were some parts of the night that I couldn't recall. For example, did I actually fuck Jen?

Jen smiled mischievously at me. "Don't be coy. You're not as innocent as you look! After what you did to me last night, I've seen your wild side." She then gives me a deep kiss, tongue and all.

After some more chit-chat, Jen got up and took a shower. I noticed that her pussy hole was opened up and I could could see dried-up spunk around Jen's cunt lips. As I got up, I quickly realized that a cum-filled condom was still on my cock. The rubber had broken and much of it was wrapped around the base of my cock. The head of my cock was exposed. Well, that settles it... I had fucked Jen and nutted in her!

We exchanged cell numbers and went our separate ways that day.

Epilogue:

I thanked Mike for the fuck session with Jen. "My little brother is growing up!!" Mike said proudly. He then gave me a high-five and was grinning from ear-to-ear. I didn't have the heart to tell him that I had also fucked his girlfriend Kristy. If Mike had found out that his girlfriend fucked me, it would have hurt him so much.

Since Jen was in college and I was going to be a senior in high school, it was natural that we would go our separate ways.

I will never forget the time I lost my virginity to my brother's girlfriend, Kristy! It was short and primal, but life-changing. That, in addition to fucking Jen, gave me a lot more confidence around girls. In a period of 12 hours at a frat party, I had fucked two college girls, one who swiped my v-card.

When I entered my senior year in high school, I wasn't the same geek that I was (the year before). For one thing, I was no longer a virgin!

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Read my story "Taking Her Virginity" for the sequel.