Erotic Couplings

My Girlfriend's Summer Fling: Chapter Two

Kelly shares the enjoyable summer moments she experienced with Charlie.

Spankmasters
May 30, 2024
12 min read
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My Girlfriend and Her Summer Fling Ch. 02
My Girlfriend and Her Summer Fling Ch. 02

My Girlfriend's Summer Fling: Chapter Two

I sat in my room, shaking slightly as I grasped my phone. I was anxious to see what Kelly was going to send me. My excitement was palpable, knowing that my girlfriend had taken my confession about liking porn stars quite literally.

On my laptop, I had a picture of Kelly she had posted just a few hours ago. Her hair was down, and she wore a little black dress that revealed her beautiful large breasts. One particular image stood out - Kelly had leaned forward, offering me a perfect view of her ample cleavage. Those large, milk-white breasts promised to spill over the dress at any moment.

In another photo, the dress was even shorter, just reaching her mid-thigh, cinched in at the waist. She wore tight leggings (known as pantyhose in the US) underneath. Combined with her height and heels, she appeared as a tall goddess. I couldn't help but feel jealous that Charlie's face was so close to her heaving chest.

The array of photos had left me aroused, and I couldn't bring myself to climax until I received the video. It was 1 am when she sent me a message, asking for permission to ride Charlie's cock again. It took until 2 am before I heard the first notification. In that time, I reflected on how far I had come over the last week in overcoming my fetish. But now, I was discarding it all.

Over the past week, I had sought advice from trusted people. The first was a friend from school, Jamie. We had a few drinks while sharing college stories. I didn't tell him the truth about my relationship, but I still managed to ask for his thoughts. In a lie, I shared a story about a male friend who had a threesome with his girlfriend. He laughed, and said:

"What a weirdo! Why do you care about that?"

That's what I was? A weirdo? A few days later, I sought advice from my stepfather. He was a tough guy but honest, so I approached him while he was working on his car. In another lie, I told him that it was my roommate who had been cheated on. He growled:

"How can you even consider taking her back? A real man would break the guy's nose and leave her!"

I wish I could say that hearing these words made me reconsider, but my erection remained strong as I opened the final file.

Kelly had sent a video.

My clammy hands worked quickly to open it without hesitation. It was the year 2012, so videos on phones weren't as clear as they are today. However, I could still make out Charlie, who was recording the intimate moment. In the background, his spare hand reached around and stroked the back of Kelly's head. Kelly was moaning as she sucked Charlie's unprotected cock.

With each time she lifted her head, her eyes faced the camera - at me.

I could hear the wet sound of her lips around his cock. His grunts were audible with every thrust into hers. The camera focused on Kelly's face, her mouth parted, moaning freely. As she wore no protection, her pussy was visibly wet from his penetration. His fast, powerful thrusts were pushing deep inside my girlfriend's pussy.

Another message appeared in my inbox. "I'm sending two more videos for you, sweetie!" Kelly wrote. I couldn't believe it. More?! I was already on the edge, but now my recklessness compelled me to click open the next file.

The scene was filmed with the phone's torch, turning it into a light source. Charlie was recording his own orgasm. He was thrusting into Kelly, causing her breasts to jiggle. The camera lifted, taking in her face as she enjoyed herself. As he finished, the camera lingered on her heaving chest and moistened lips, stained from Charlie's semen.

I couldn't wait any longer to release the cum I'd been holding back - a steady stream of pre-cum was dripping down my shaft now. But first, I had to see everything else. After what seemed like forever, I finally opened the last video I'd received. It began with my naked girlfriend placing the phone on what appeared to be a nightstand near the bed. There was no flash this time, making it the darkest video yet. But I could still make out her climbing into the bed. Charlie was lying flat, as Kelly carefully positioned herself on top of him.

She murmured how good it felt, how big he was. What followed was two minutes of my girlfriend riding his cock. From my vantage point, I could see her escalating her movements, her tits slapping against her chest with each thrust. Her moans grew louder as it was evident they no longer cared about making any noise. I loved watching her get more and more passionate, collegefuckbook.com appreciating her from a gentle rocking to an intense bouncing motion.

I could tell she was close to cumming. So intense was it that I couldn't control myself. My load shot out of me thirty seconds into the video, leaving behind a wet spot in my pajamas. Defeated and covered in cum, I continued watching the rest of the video. Kelly, still on top of Charlie, was grinding her hips frantically as she threw her head back in pleasure. Her hands rested on his chest, supporting herself as she rode him with a fierce passion.

The voices of my friend and stepfather kept replaying in my head. "Weird. Bitch. Pathetic." They were like an uninvited echo throughout the whole video. Eventually, Kelly climbed off Charlie's cock and picked up the phone to end the recording.

I couldn't help but feel a new low had been reached. Lying there in my bed, naked and covered in cum, I reflected on the choices I had made. I didn't blame the girls involved—they had simply given me what I requested. I couldn't deny it, or shift the blame onto anyone else. I was the one who chose to escalate things in the first place. Despite my best efforts to delete those videos, I ended up watching them again, each time making me harder.

Seeing her ride him in the dark, the way he caressed her thighs, the way her ass bounced off his balls, it was enough to make me cum again, even though I was limp.

It was just a few days later when I returned to university for my second year. Confidence was at an all-time low. I'd moved into a shared house with several classmates. Though Kelly and I had considered living together, we ultimately decided we were too young to live together. The past few months had brought drastic changes into our relationship - going from a shy, sweet couple to a shaky dynamic.

Our first date after the videos had been exchanged best showcased this. I was nervous and anxious about being seen with her. Was anyone else checking her out? Why wouldn't they? She looked incredible, with her hair in a ponytail, cat-eye liner accentuating her striking blue eyes, and a dress that swayed with each of her steps, revealing a hint of her cleavage. Even as she talked about her home troubles - her dad being a pain in the ass - I couldn't help but steal glances at her body, wondering what Charlie had done to her over the summer.

She wasn't the shy girl she'd been before, now oozing confidence. Her new, bubbly, outgoing personality left me questioning why she was even with me.

We made it back to her university house after, where she shared a room with Anni and two other girls. Thankfully, they had left the house, leaving us alone. We didn't waste any time—she was bent over her bed, panties around her ankles, awaiting me. I gave in to my frustration, gripping her hips as I thrust into her with all my might.

"Oh fuck! Harder, baby!" she begged. She never used to talk so openly about sex before, but I hammered away as hard as I could, desperate to satisfy her. All I could think about was how dissimilar this experience was from the sounds in the videos. It left me yearning for something that made her moan the way she had in those recordings.

Imagine this: Tommy, give it your all! Tug on my hair! What's going on here? She's never acted like this before. She used to be more assertive, and yet here I am, giving it my best shot, fearing I might cum before I can satisfy her or blackout. Sadly, I reach the former goal earlier than I'd like. I fall back, my dick now encased in a condom filled with sperm. She didn't look happy at all as she exhaled a deep sigh and pulled off the condom. With a practiced move, she tied it with ease.

Do you remember our early days together? I recall her telling me she was on the pill and wasn't fond of condoms since she was a virgin. Naturally, I assumed she had never used one, that is until she started dating Charlie. Now she's tying and untying condoms at ease. It's arousing to see her handling a condom full of sperm - had she ever swallowed Charlie's? Why now did she start meaning this girlish, skimpy panties? She tossed the panties in the bin before heading to the bathroom.

"Are you headed to yours?" Her tone was chilly, not knowing where this was coming from.

"Yeah, I'll be off soon." I replied, trying to understand her sudden need for condoms.

Why's she so insistent on wearing them? She knows I'm clean, and she should be too if she was with Charlie. Could she be hooking up with other guys? My jealousy was steaming up. I glanced at the bin, thinking there might be more condoms underneath the trash.

"What're you doing?" Her voice halted me, scared.

I was so naive; I asked her if she was sleeping around. Why the obsession with condoms? What's with the skimpy clothing? We argued, she got angry when I accused her of cheating. She got angrier when I questioned her not finishing.

"Was it my fault you didn't make me cum?" She retorted.

A piercing pain struck me as she said it. After years of self-loathing and hopelessness, I was more humiliated than ever. Ken and Charlie had both made her cum. But I couldn't.

I left, not knowing what to say. We didn't talk throughout the day, but to my surprise, I woke up to an apology. She was sorry for saying it, but never denied its validity. It was enough for me to consider seeing her the following day, expecting a passionate argument; instead, her response showed no trace of anger or frustration.

I opened the door to her and my jaw dropped. Her naturally dark hair cascaded down, accentuating her gorgeous face adorned with vivid make-up. I had never seen her with such polished make-up, her red lips especially. Her eyes were adorned with a stunning purple eye-shadow. She was shielded by a long trench coat, but her tall stature emerged from the coat due to her heels, making her nearly six feet tall.

"I took a cab over, let me in quickly!" She instructed, urging me to let her into my room. She was whispering and even seemed slightly bashful, even though her outfit was so provocative. In my room, she shed the coat to reveal nothing but her enticing blue corset. The see-through lace clung to her fantastic curves, her large breasts peeking through the bra cups, and the lace fabric vanishing between her inviting ass. She turned towards me. Strutting towards me, her heels tapping against the wooden floor.

"I'm sorry for what I said. I wanted to make it up to you." She whispered before kissing me. She slid her fingers down my waistband, pulling my shorts off and exposing my erect cock. While we were making out, she squeezed my hard dick with her fingers, her lips traveling down my neck, chest, and tummy. Kelly was on her knees with my rod nestled in her magnificent breasts. It felt like watching a porn star in the flesh, and my cock was thrilled.

She apologized for what she said last night. She wanted to make up for it. Her distinctive perfume filled the room as she traced her lips to my cock's girth. What a switch - she appeared to be a porn star on my behalf.

"Being a good slut for my boyfriend." She whispered, teasing me with her touch.

Her hands wrapped around my waistband as she pulled my shorts down, exposing my rock-solid prick. Kissing my neck, chest, and tummy as she sucked and licked me passionately. Kelly was on her knees as my dick stuck up between her ample drenched breasts. Theeping sound of her tongue rubbing against me, using my skin to rub against her firm breasts. I couldn't resist: "Kelly, what are you doing?"

"Being a good slut for my boyfriend." She repeated. Just to make sure I had all of the detail, her lips latched onto my dick, her body juxtaposed with the red liquid resting on her skin. She used one hand to guide her breasts around my cock, her lips and hands down to my happy trail, then moving her hands to my ankles. She eagerly took me in as my orgasm came so unexpectedly. As she moved her head, I felt her lips suck and release multiple ropes of cum, but she remained eager, her tongue dancing across my tip. To my amazement, she drank it all, savoring my essence.

Wow, that was intense! Kelly led me to the bed and spread her legs wide so I could sink between them. She leaned her legs on my shoulders and took off her outfit, revealing her soaking wetness. Kelly had me eat her out, and she really loved it when I listened to her specific instructions. It was mind-blowing when she finally orgasmed. Her body was dancing wildly around, and she had to cover her mouth to muffle her scream.

Suddenly, she was cupping my semi-hard dick.

"Do you want to fuck me like a slut now, sweetheart?" she asked softly. I hesitated, but if I could get hard enough... Kelly understood and grabbed my laptop.

"I'll help you get hard," she offered with a mysterious glint in her eye. My stomach fluttered when she opened my laptop and placed it on the nightstand. My eyes nearly popped out when I understood what she was doing: she was about to show me videos of her and her ex-boyfriend doing very naughty things. We watched in silence as I felt my dick getting harder by the second as we viewed the videos on loop.

It was mind-blowing how I pushed into Kelly from behind as she screamed while watching the videos on the screen. The sounds of Kelly's passion, the intense glare of her own sexual arousal. I was thrilling as she rode me. As hard as I could fare.

"Look at me, I'm such a slut, am I not?" she panted.

"Yes baby, you love cock, don't you? You enjoy seeing yourself ride dick!"

The sexual tension rose, and our words egged each other on. Just as she was about to mount me to reenact a position she had with her ex, she made me watch her as she pressed her face into the pillow to keep her passionate wails from waking the neighbours. We shared this fantastical moment as we watched her inzelbude on her own slutty behavior and riding my latex-clad cock in the same way she used to do with her ex.

Rewind the clock to earlier, and Kelly still had her head in my lap. She asked me if I had come teasing at the videos of her and Charlie. I struggled to get hard, but my resolve melted as she whooped and whined, urging me on. How long would she go on? How could I make her cum when she was enjoying her sexual acts with Charlie? We shared some moments in our naked state in front of my laptop and rejected her though. I didn't know how to make her orgasm, nor did I want to repeat the shame she felt about her past.

We both must have sensed things would go well when our words bonded us and Kelly's mood picked up. She decided to wear my pajamas, a far cry from her earlier lusty self. It was interesting how the chat made our conversation easier. Kelly wanted condoms even though she didn't know what was going on with her ex, and even though she didn't insist she had to cum in front of my laptop. She filled me in on her family's sexually vulnerable background.

In an eternity of guilt, Kelly's father had been a hardass, constantly judging her for her appearance and labelling her a whore for her revealing outfits. She confessed how she frequented parties and hooked up with guys over the summer, much to her father's dismay. Despite it all, she admitted that she had fun with her ex, but the independent woman she is was the one who made me orgasm.

Funnily enough, Kelly was just like me. I enjoyed her slutty behavior but regretted it afterward. Staring at her, I noticed that the same feelings of shame and embarrassment reflected through her eyes as we parted. It was concerning how similar we both had the same sexual past, and her position now mirrored mine when I was with Ken. The way Kelly's hands caressed herself, the frustration on her face for having slept with a lot of men. And, more strikingly, her fear of being seen as a slut.

I tried to soothe her, reminding her that all the naughtiness was in the past, and our shared experiences would make it easier for her to embrace her cravings. I thought that acknowledging our darkest secrets would help bond us. But instead, it was like trying to control something you couldn't. It soon became obvious that I wasn't strong enough to make everyone comfortable with their sexual desire. Emphasized for Repose

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