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Amanda vs. The Field: Chapter 2

A man secures a date while working during the summer months.

Spankmasters
May 12, 2024
7 min read
virginVs. Ch. 02 Amanda Vs. The Field
Vs. Ch. 02  Amanda Vs. The Field
Vs. Ch. 02 Amanda Vs. The Field

Amanda vs. The Field: Chapter 2

I've been on multiple dates and have even dated more than one girl at the same time. Sometimes, I didn't choose either of them. Other times, they both ended up dumping me. I think it would be interesting to share these real-life experiences, with the names changed, of course. Here's the next story in chronological order.

This summer job was unlike any other. Most employees were college students like me. We spent most of our time gossiping and attempting to woo the girls who worked there. The people responsible for putting together the products were called table people, and they were mostly men. The bucket people, who moved the carts, were mostly women. These interactions provided numerous opportunities to ask these ladies out. Of course, we also performed our duties.

I first attempted to flirt with a bucket girl, which resulted in a date with Jenna. She suggested I come over to her dorm room to watch a movie. I had no idea college students still lived on campus during the summer. Upon entering her room, I noticed her long, dark blonde hair, always styled in a slender ponytail that matched her slender frame. The bouncing of the bucket with each step she took as she brought it provided a view of her big, bouncy breasts.

Jenna invited me in, offered me a soda, and turned on the movie. I sat next to her, but not too close on her loveseat. I soon noticed numerous pictures adorning her walls, all featuring the same guy. I cheekily inquired who this person was, hoping it was her brother.

She shivered and whispered, "My boyfriend." At that moment, I was completely clueless about my purpose there. I finished the movie, left, and didn't interact with her much after.

It's okay, there were other bucket girls. I continued online dating as well, and my next potential match was the adorable Sophie. We exchanged funny emails and seemed to be a perfect match. However, she was home for the summer. Then, an unusual situation arose - my roommate Ben, with whom I shared a living space, was also chatting with a girl named Sophie. We realized we were in love with the same girl. We started arguing over trivial matters.

I tried dating other bucket girls. I even had one date when our personalities didn't mesh well. I also pursued a Berean girl, only to learn they preferred dating within their own community.

One day, I noticed a girl I hadn't paid attention to before. Amanda was tall and thin with short blonde hair, wearing a pink tank top and shorts so short they revealed her muscular thighs. She wasn't incredibly beautiful, but her full lips made her kissable. We chatted a few times and then invited her to join us for free beer at Old Chicago every Wednesday.

She accompanied her roommate, who was also tall and thin, looking like a sexy librarian. Amanda stood at around 5'10". She wore a cute pink shirt and very short shorts. Her legs were toned and nearly muscular. Our engaging conversations led us to exchange phone numbers and promised to set up a weekend date.

We went on a few fun dates, sharing similar senses of humor and perspectives on life. We both came from rural backgrounds and were both inexperienced with dating, yet to even kiss after a few weeks. I realized I had to pursue the relationship, fearing I might be trapped in the friend zone. [

One evening before my friend was leaving for military camp, I dropped by her apartment. We were watching a movie with her roommate when she said she still needed to pack. She went to her room, leaving me alone in the living room. I was puzzling over what to do next, afraid she would announce she was going to sleep soon and I'd have to leave when she emerged from her room, I decided it was time to make a move.

In her room, she had only a desk lamp lit. She was dressed in fatigues and a tight army green T-shirt. My serious expression seemed to scare her, and she questioned me. I didn't respond but instead enveloped her in a hug and planted a kiss. We became passionate, our arms wrapped around each other as we locked lips. The situation reminded me of scenes in movies where I stop a girl at the airport and propose marriage. I was elated to finally kiss this girl I'd had a crush on for weeks. She asked what was amusing me. I shared my happiness about engaging in this act.

Admirable as she was, this woman had stunning, full lips. A wonderful kisser, she matched her height with me, making the experience feel natural. We closed our eyelids, engrossed in finding our way within each other's mouths. Suddenly, I opened my eyes, surveying her outfit. I raised her T-shirt by the hem and pulled it over her head. She, in turn, removed my shirt. She put her palms on my chest as I touched her waist. I enthusiastically admired her toned skin and trim stomach, allowing a glimpse of her belly button. I was eager to see her breasts but also uncertain about how far she'd permit me to go. I was inexperienced in the ways of women, and hadn't brought any condoms. Unhappily, Amanda hadn't concluded her activities yet. She loosened my belt, removed my jeans.

As I shed her fatigues, excitement soared contemplating undressing a hot military woman. She wore black panties. Her backside, slightly hidden by the jeans, appeared tempting. I fondled her bum gently from the backside. She giggled, a sweet, pleasant sound. She lay on the bed, her legs bent, awaiting my arrival between them. Straddling her thighs, I caressed them up and down. Their fairness, faintly adorned by fine blond hairs, mesmerized me. She shared that she had never shaved her legs outside of the knee line. I stared at the gentle curve of her behind and the bare ass I could almost feel against my hands. She teased me with a playful smirk, asking what I was going to do. Then, to my dismay, I hesitated. Admitting I'd never engaged in such acts, and wasn't prepared, I confessed I didn't have a condom. She seemed unsure as well but remarked finding a token of commitment would help her through camp.

In the following weeks, we encountered somebody named Sophie. We faced her, Ben inviting me to meet her. As we encountered her at a high table, I recognized her from her images, but she appeared heavier, around 250 pounds. She revealed her struggles with depression and an eating disorder, and how she didn't want a relationship right now. That was fine by me. Ben jokingly initiated, "You can take her!"

Over the past couple of weeks, it's been pretty quiet. I didn't hear from her, so I assumed she still liked me after the time apart. When she called, I was thrilled. She couldn't wait to see me and asked if she could come over to my place that evening? No problem. We had plans to go mini golfing, but when I opened the door, she looked stunning. She had on a tight, light blue shirt and short khaki shorts. Our embrace was passionate as if we'd been thinking about each other nonstop. It was intense, passionate kissing. We ran our hands all over each other's bodies and attacked each other's mouths with desire. My penis was as hard as it had ever been.

"We're not making it to putt putt, are we?" I asked.

"Forget putt putt," she said. We ripped off our clothes in the living room.

"I'd rather fuck you," I told her.

"I'm glad to hear it," she said. "I couldn't believe you turned me down last time!"

"I won't make that mistake again," I said.

"Have you done this before?" she asked.

"Just a couple times," I told her. "You've seriously never had sex before? You're so hot!"

"No, I've only sucked a guy's dick at a party once, but that's it. You don't want to hear about that though." She was now naked. She had a cute triangle of pubic hair and a beautiful ass. Her ass was a gorgeous heart shape with a pale, perfect texture. She threw herself on the bed, and I leaped on top of her, kissing her soft, big lips. I made a detour by caressing her breasts, her sexy biceps, and kissing her belly button, which made her giggle. Her body was sleek, almost fat-free. I caressed her lovely, large calves and ran my hands over her firm, milky thighs.

"Oh my God, lick my pussy already. I can't take it anymore." She begged.

"OK, I'm done teasing you," I said. I started kissing her hot, sexy lips and slowly made my way to her slit. You'll never guess how amazing it felt. I began licking her clit and slid my finger inside her. Her slit was so wet that it tasted sweet, and, to top it off, she had the most beautiful pussy I'd ever seen.

"Mmmmm, stick that big dick in me right now," she cooed.

"OK, I'll get a condom," I said.

"I'm on the pill. You can cum inside me if you want," she said seductively. Here, I got harder than I'd ever been.

"I've been waiting for this since I left your apartment 2 weeks ago." I moved on top of her and inserted my dick into her tight opening. From what I could see, she was in pain when I got in. There was blood on my dick. She really hadn't done this before.

"You feel incredible, Amanda," I said. "You feel so tight." That seemed to take her mind off the pain or she was feeling better after the initial entry.

"That's because I'm a virgin," she said.

"You feel warm, Amanda," I replied.

"That's because I'm a mammal," she said, in her sexiest voice possible.

Our dirty talk needed some practice. I'd only been inside her for a minute or so, but she was so tight without a condom. The sensation was beyond anything I'd ever felt. I was close to cumming, so I pulled out, saying, "I'm going to cum right now, but I don't want this to be over yet."

"Oh, I'm that good?" she asked. "Put it back in me. I want you to cum inside of me. I've always had a fantasy about a guy cumming in me."

I was back inside her. I tried to go slow, but her tight pussy pulled me in deeper and made me pump her hard.

"I think I can feel your heartbeat in your dick," she said.

"I'm about to cum," I said. I held it off as long as I could. Then I thrust my dick into her powerfully, let out an "Oh," and unleashed jets of cum in her deflowered pussy. I was utterly spent. I rested my head on her chest. To my delight, her heart beat fast. It was a little calming and reassuring.

"How does my cum feel inside you?" I asked.

She answered, "Warm."

"Are you my girlfriend?" I inquired.

"Do you want me to be?" was her question back.

"Yes" was my response.

A warm smile appeared on her face, she gently held my hand, and she kissed me passionately.

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