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The First Time Chronicles - Part One: How Gary Lost His Virginity in High School

"It all started when a redhead walked into the room..."

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Author's Notes

"The First Time Chronicles will be a series of short stories about Gary and Amina Mitchell, describing some of their sexual firsts. <p> [ADVERT] </p>In this first part, Amina insists that Gary divulge everything about losing his virginity to a redhead when he was seventeen."

As I was celebrating my tenth anniversary with my beautiful wife, I happened to glance up toward the door. I stopped mid-sentence and gawked uncomfortably at the redhead standing near the hostess stand. Her hair was shorter, falling just over her shoulders rather than teasing the top of her ass as it once had. It had been fifteen years since I’d seen her, but it felt like fifteen minutes.

“Hey, earth to Gary,” a voice interrupted my silent reverie. “Where’d you go there?”

I turned my attention back to the love of my life and had to make a split-second decision whether to fess up or pull some lie out of my ass. I’ve never been good at deceit, and it hardly seemed wise to be less than honest with the woman to whom I’d pledged vows.

So, I went with the truth.

“I’m sorry, that was so rude of me. It’s just that I was surprised to see her standing there,” I said, trying to buy myself another moment to figure out what to say.

“Who is she?” Amina asked, her eyes narrowing with suspicion and her bottom lip quivering ever so slightly.

Come on, Gary. Don’t be a dick. Full disclosure is your best bet.

“She’s the woman I lost my virginity to in high school,” I blurted out.

Amina’s right eyebrow raised as she pursed her lips. It took a moment for her to respond.

“Well, she’s walking this way, so…”

“Gary? Oh goodness, I haven’t seen you in ages! How are you?”

“Um, I’m fine. I just, um, this is my wife, Amina,” I said, tripping over my words like an idiot.

“Well, hello, Amina; it’s lovely to meet you. I’m Serena, Gary’s A.P. Biology teacher when he was a senior.”

Amina gave me a look.

Seriously?

I grinned sheepishly and felt myself regaining my composure.

“Miss Johnson was my favorite teacher in high school,” I said, making Serena blush.

“Aren’t you sweet? And you were one of my favorite students. You were always so kind and well-mannered. Well, I am meeting some friends here, so I’d better check if they’re here yet. It was lovely running into you.”

I couldn’t help myself; I watched Miss Johnson’s delightful ass wiggle as she walked away. But when she looked over her shoulder and licked her lips in our direction, I felt myself grow hard.

As I resumed eye contact with my wife, my face was hot with shame.

“I’m so sorry.”

“For lying about your first time? Or watching her ass like you wanted to fuck it as she walked away?”

“Both?”

“You’re a piece of work, Gary.”

I felt like a piece of shit.

“Amina, how do I make this better?”

Now, my wife is not a prude by any stretch of the imagination. But I nearly fell out of my seat as the words came out of her mouth.

“Take me home and tell me every single detail.”

“Huh?”

She continued, “If you turn me on with the story of how you lost your virginity to that stunning redhead, I’ll let you fuck me tonight. Otherwise, you can eat my pussy, and we will skip your orgasm as punishment.”

My cock twitched.

“Who are you?” I asked seductively, extremely turned on by my wife’s sudden assertiveness.

“Get the check, Gary.”

“Yes, ma’am.”

The car ride home was silent. Amina wasn’t visibly upset but wasn’t warm and fuzzy either. I wracked my brain for details, wondering if sharing them all was a good idea.

As if she had read my mind, Amina said, “Don’t even think about holding anything back.”

“Of course,” I agreed.

When we got home, I wondered how this would all play out.

“Where should I start?” I asked tentatively.

“From the beginning, of course.”

“Before I do, I need to know, are you mad?”

“I’m not mad. I’m curious.”

“Just so you know, I didn’t ever tell you about Miss Johnson because I’ve never told anyone about her. I could have gotten her in a lot of trouble, and since I was a willing participant, I couldn’t fathom doing anything to hurt her.”

“I understand.”

“And, of course, I thought we agreed that our past was our past as far as sexual experiences were concerned.”

“You’re right. This is different.”

“How is it different?”

“I lost my virginity to a pimple-faced neighborhood boy who managed three full strokes before he pulled out and came on my belly, leaving me unsatisfied. You lost your virginity to a red-haired goddess with gorgeous tits and a perfect ass. I’m willing to bet you had an amazing orgasm. See the difference, Gary?”

“Why do you want to hear about it? I feel like this will only make you more upset.”

“Maybe I had a thing for redheaded women in college and want to hear every fucking detail because I miss those days!” Amina shouted.

I blinked.

Amina liked women? Redheaded women?

I wondered if now was a good time to mention that the tab at the restaurant had been accompanied by Miss Johnson’s business card in case I wanted to meet up sometime. Probably not, but my brain instantly went to the possibility of a threesome, making my dick hard.

Down boy!

“I didn’t know you were bisexual. Why didn’t you tell me?”

“Because the guy I was dating before I met you got weird and started wondering if I was comparing his oral technique with a female’s. He eventually told me the pressure to satisfy me was too much.”

“Well, he was an idiot,” I blurted out.

She laughed, causing me to let go of the breath I didn’t realize I was holding.

“Yes, he was. And maybe I’m stupid for wanting to know, but I promise you I’m not gonna get mad if you tell me. I know it’s weird, but I really do want to know how she seduced you.”

“So, it seems we both had secrets. I will tell you all about my first time with Miss Johnson. But then you must tell me about your first time with a woman. And neither of us will be angry with each other, deal?”

“Deal.”

I looked at my wife and realized that there was no turning back. I’d be honest; hopefully, she’d be turned on enough to let me climb between the sheets with her. If not, I’d treat her to some satisfying oral sex and take care of myself afterward by hand.

“Okay, but if at any point you change your mind and don’t want to hear anymore, please speak up.”

“Gary Mitchell, if you don’t start telling me every single detail right now…”

“Okay! So, um, I was supposed to have Mrs. Benson for biology, but she decided to retire a few days before school started. So, they hired this new, young teacher named Miss Johnson to take her place, and a bunch of us were talking shit about how we needed a teacher that could prepare us for college and that a brand-new teacher wouldn’t cut it.”

Amina nodded.

“So, in walks, this gorgeous redhead, and I think she’s a new student. I introduced myself and proceeded to include her in the conversation I’d been having with my buddies about how the school district should have provided us with a knowledgeable teacher since most of us were planning to take the A.P. test.”

“Ouch, how did that go over?”

“Well, at first, she just nodded and said maybe we should give the new teacher a chance. I shrugged and motioned to the chair next to mine. But she mumbled something about already having a seat up at the front of the classroom.”

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Amina chuckled.

“Yes, she got a kick out of the look on my face when I realized her seat was at the teacher’s desk. I was so embarrassed. But she didn’t call me out in front of the group. She did, however, ask me to stay after class.”

“Tell me more.”

“After class, she said that she hoped she could count on me to influence my classmates positively. She also made it clear that she was plenty qualified to teach the course and didn’t want to be harassed by students just because she was younger. I felt a mix of shame and something I couldn’t put my finger on at the time, but eventually, I figured out it was lust.”

Amina nodded. “Go on.”

“So, about a month into the school year, I stopped by her classroom at the end of the day to grab a notebook I’d left behind. She was sitting at her desk, crying. The gentleman in me felt it necessary to ask what was wrong. She was startled, not realizing she was no longer alone. She shook her head, wiped away her tears, and regained her composure. Apparently, a man had broken her heart.”

“And what did my knight in shining armor do?” Amina asked, smiling for the first time since the evening had gone south.

“I took her hands and told her a real man doesn’t break a woman’s heart. Then I felt my burgeoning erection and hightailed it out of there before I embarrassed myself. But the next day, she asked me to see her after class. She asked me what I meant by a real man. I stammered, as just being near her was causing a hard-on. Then she shocked the shit out of me and said to come back after school, and she’d take care of that for me.”

“She said that? That she’d take care of your hard-on for you?”

“Yep. So, my seventeen-year-old dick was at half-mast the rest of the day.”

That made Amina laugh, which made me relax a bit.

I paused. It felt unnatural telling my wife about how I fucked my first pussy. But she wanted details, and I was smart enough to know that leaving anything out would be considered lying.

“When I returned to her classroom, she told me to wait a moment and left the room. I was starting to wonder if this was some sort of trap and if she’d gone to get the principal. But a few minutes later she came back and said to follow her. We ended up in a storage closet. She pressed her body against mine and told me she needed to suck my dick. I wasn’t going to argue with that.”

Amina smiled at me. “Did she get on her knees?”

I smiled back and said, “She certainly did. And she unzipped my pants, took me in her hands, and looked up at me with those pretty blue eyes as she licked my entire shaft. It took a lot of thinking about football and tea at my granny’s house not to immediately shoot my wad on her face. Fortunately, she was hungry for cock, and she devoured mine like she’d been deprived for weeks.”

Amina’s nipples poked through her silk blouse, which we both noticed, and she blushed. “Fine, yes, your story is turning me on. The fact that I’ve seen the mouth and the blue eyes attached to the woman who sucked you is making it play out like a movie in my brain. Please do not stop now.”

“That’s pretty much what I said when she hesitated part way through. She said what we were doing was wrong and that she shouldn’t have brought me to the closet.”

“How did you get her to continue?”

“I promised if she finished me off, I’d lick her pussy, and then we’d never tell anyone what we’d done. So, she sucked me like a fucking vacuum cleaner, and I shot my load down her throat. Then, I helped her onto a countertop and spread her legs. She had no panties on; she later admitted she never wore them. I can’t claim I had any finesse at that age, but I licked, sucked, and nibbled on her sweet, juicy pussy until she grabbed my head and started grinding into my face. The look on her face, when she came, was incredible. I’d done that! I’d made her cum good and hard.”

Amina was rocking subtly in her chair. I was so turned on by the sight of her getting aroused by my story that I continued without prompting.

“And speaking of good and hard, my young man’s rod was ready for action again. She took one look at my raging hard-on and told me to be a good boy and fuck Mama’s pussy. She didn’t need to ask twice. I plunged into her like a rutting bull, and she thrashed about like a wanton whore. I kept ramming like a jackhammer as she bucked against me, her tits nearly bouncing out of her blouse. It was hot and sweaty sex, and I fucking loved it. I felt like a man when I made her scream, and I followed right behind her, filling her with my jizz.”

“You fucked her without a condom?”

“It was spur-of-the-moment sex. And afterward, she assured me that she was on the pill.”

“And nobody caught you, even with her screaming?”

“It was after school. No one was around except the custodian. And if he heard, he surely never said a word about it.”

“What happened next?”

“We got ourselves together and swore we’d never do anything like this again and wouldn’t tell a soul.”

“But…”

I grinned. My wife knew me very well. “But we were like two kids in a candy shop. She kept me after school at least once a week and took me to the closet. She taught me a lot about sex and how to please her. During sex, she called herself Mama and said I was her special boy. Initially, it was a little weird, but it turned her on, so I just went with the flow. I was having regular sex with a beautiful redhead and learning to be a real man.”

“How did it end?”

“I graduated and went to college. I missed the sex, but there was plenty more to be had, and I was considered a real catch since I was known for my experienced tongue.”

“You sly dog. I’ll bet you licked your way through a slew of girls.”

I looked at my wife and saw lust in her eyes.

Now, Gary. Bring it up now. If she will ever say yes, it’s now while lust is running through her veins.

“She left me her card.”

“What, now?”

“At the restaurant. Miss Johnson left me her card. Said to contact her if we were interested in meeting up with her.”

“We?”

“Well, she didn’t specify, but I’m not interested unless she meant both of us.”

Amina squirmed in her chair. “Do you think she likes women?”

“Only one way to find out.”

“Call her.”

“Are you sure?”

“Do it now, before I lose my nerve.”

I grabbed my phone and took the card out of my pocket. Dialing the number, I felt butterflies in my stomach. I remembered how it felt that first time Miss Johnson led me to the closet. Then she answered, and that voice made me instantly hard. I put her on speakerphone so Amina could hear.

“Hello?”

“Hello, Miss Johnson, it’s Gary.”

“Oh, Gary, you did call! I was hoping you would.”

“Yes, well, I, um…”

“Before you say anything, I want you to know that I think your wife is gorgeous. You’re a lucky man.”

Amina wiggled her eyebrows.

“I am a lucky man indeed. Say, listen. Your card said I should call if I wanted to get together, but I don’t step out on my wife, so…”

“Gary, my sweet boy, I meant I wanted to get together with both of you. Mama likes special girls, too.”

I grinned at Amina, who wiggled her eyebrows again and licked her lips.

“In that case, we’d like to get together when it’s convenient for you.”

“I’m free tomorrow evening.”

Amina nodded.

“That sounds wonderful, Miss Johnson.”

“Please, Gary, you’re an adult now; call me Serena. I can’t wait to taste your wife. I’m sure she’s delicious.”

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Written by techgoddess
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