Group Sex

Her Girlfriend's Summer Romance

Tommy and Kelly look for summer entertainment.

Spankmasters
May 26, 2024
10 min read
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My Girlfriend and Her Summer Fling
My Girlfriend and Her Summer Fling

Her Girlfriend's Summer Romance

Me and Kelly wouldn't be seeing each other for quite a while. I was back home for the summer as was she. I told myself I should be thrilled about being given permission to sleep with another girl.

Why shouldn't I be happy? Why shouldn't I be out there at the club trying to pick up girls? Yet almost every night, I found myself at home in my room, jerking off while watching porn instead. My thoughts kept going back to memories of her with Ken. Reminiscences of my roommate forcefully having sex with my girlfriend.

Each time she posted a new picture on Facebook, these memories of Kelly with Ken would surface. There were plenty of them. A certain photo in a low-cut top made my cock twitch, the one where she took a selfie in a pub with a group of friends. The glimpse of her pink bra peeking out from her strappy top. Her huge breasts in focus.

I couldn't help but wonder if Ken was sitting there, looking at that photo. I wondered if the guys in the pictures were making a move on her. I tried to convince myself I detested the idea, but the mere thought had me dripping cum within minutes. I felt guilty and ashamed after each session of self-pleasure.

Kelly and I both agreed not to talk about sleeping with other people. I reciprocated by not mentioning Ken, too. We had decided that after this summer, it would just be me and her again. But I couldn't find myself approaching another girl.

The good news was, Kelly had invited me for a weekend getaway. She'd been working a summer job with some old school friends, Charlie and Jemma, and saved up enough money to stay in a hotel. I couldn't believe my luck. This was exactly what I needed to escape the mental prison I was in, the cycle of shame. All I needed was one night of passion with my perfect girlfriend.

The day arrived, and I was excited when I saw her in her cute floral dress. I ran to her, and we hurriedly dumped our stuff at the hotel. We went out to grab some food and drinks, and finally, that night, I was alone with Kelly.

She looked different, happier and more confident. She walked around with her head higher. I was attracted to her. This was her living life, while I was stuck in my room, wasting away. She even commented on how depressed I seemed. I had been for the past few weeks, but that didn't matter anymore.

When we got around to having sex, it was a mess. Clumsy and awkward. Even the process of putting on a condom made me feel intimidated. I couldn't help but focus on Ken cream pie-ing her. The thought kept flashing in my head as she put on the condom and mounted me. Her dress fell down, revealing her amazing breasts. I'd missed them so much. Her confidence, her body. After a while of her riding me, with my cock thrusting between those heaving, milk-filled breasts, the condom filled up.

I hated how she didn't reach an orgasm, and she tried to comfort me. But I was defensive and insecure because of it. Kelly asked me if there was someone else. That's when I had to come clean about my situation.

Kelly was shocked. She was surprised. She demanded more details, clearly upset that I hadn't found someone else. I felt lost, confused, and resentful because of my failure. But then she confessed something that took my breath away.

"Weren't we supposed to have a free pass this summer?" She asked. I was taken aback.

"Us?"

"Yeah. We agreed, right?" Kelly revealed. I felt sick with regret. Of course, I'd given her the same license, and now it seemed as though we had different interpretations of the agreement.

Kelly told me everything. It was excruciatingly painful. I had to know everything. No matter how excruciating it got, I insisted on details. Even growing angry with her.

"So?" I demanded. She was hurt, but also exhausted from having to explain. "You didn't think I'd do it?"

"What?!?" I asked, uncomprehending.

The date she had sex with Charlie matched the one of her skimpily-clad Facebook post. The same night I'd been jerking off in my room, jealous of the guy in the picture putting his arm around her and looking into her eyes. Charlie, her confidant since school, had been undressing her, taking off her leggings, and engaging in the very fantasy I was ashamed of.

They'd been pals for ages, and like any university students, nothing was more gratifying than heading home demonstrating how much they'd blossomed. While inebriated, she divulged to him that she was dating an open-minded man, a sexually liberated gent, so comfortable in their connection that he proposed being polyamorous throughout the summer. Charlie bragged about his academic year having been "spiritual" and he was no longer a reserved virgin. What commenced as friendly displaying soon developed into an intoxicated make-out session.

He was undoubtedly an attractive fellow, more appealing than Ken, and seemingly adorned his svelte figure with tattoos and piercings. As she disclosed to me what unfolded, I couldn't help but be enticed by the yarn while she portrayed it, as we resided in the subdued radiance of our hotel room. I felt guilty, here she was confessing, and I was commencing to savor the concept...again.

They paid a visit to his abode. Sneaking upstairs so as not to disturb his family. Charlie played the leading role, stripping down to his shorts and tossing her on the cleanly made bed. He eloquently removed her leggings, revealing her enticing limbs I dearly adored. She was embarrassed by how humid she was as he swiftly kissed her leg, advancing to her inner thigh, and soon pressed his nose and prickly chin against the loosened panties covering her womanhood.

He complimented how much he cherished devouring pussy, teasing her through the fabric. Kelly's head was spinning with booze, and as her panties were delicately peeled off with his fangs, she had to restrain her moan as the wandering, wet tongue of another man licked her lips. He flirtatiously teased her about how pierced tongues were more sumptuous.

Kelly concurred as Charlie flirted, using his digits to unfurl her captivating flap. His tongue traced her clit. His whole agenda was to achieve climax, a palm rose to stroke her cup-shaped breasts. He kneaded the luscious mounds, providing her with a surge of excitement so that his pierced tongue was soon coated in her ejaculate.

She'd been pent up, devoid of orgasm for weeks, she yearned for a moment of recuperation. Clutching her crimson cheeks, she held her moan down as the nose-tickling delight of her last boink subsided. When she pried her hands away from her muggy face, she beheld Charlie detaching a condom with his teeth. His equilibrium was already erect, he slipped the latex over his ample head and rolled it down his cock.

"How was it? Witnessing that?" I inquired. Kelly was trying to contain her tears as she confessed.

"Well... It aroused me." She quieted to me with a profound shameful tune.

She narrated she felts so inexperienced, even with the pointers learnt from me and Ken. Hearing that stung.

Charlie elevated her legs to her chest, the posture intensifying the experience for her. Kelly was entranced by how easily he slipped inside, as his face once more settled on her ergonomic nipple, bathed in her breastmilk. Deliberately thrusting her, his hips became more fervent, effectively slapping against the cushy flesh of her heinie. She desired conquest, not adoration, but being drilled so well she didn't inhibit him as he kissed her, fiery oral exchanges as she felt herself escalated to the limit. Nevertheless, prior to she could attain climax, he slowed down, rekindling teasing and fueling her excitement.

Charlie flipped her over. That way, her slender bum was illuminated. Without skipping a beat, he continued to pump her, her body losing cohesion as his hand encircled her neck. Fairly holding it, he transported her to the apex. Her back arched, her rear rose and glowed as his tattooed hips relentlessly fucked her. Kelly's moans became slightly too audible, necessitating him to shove two fingers into her gob to subdue her, her moans were followed by another climax.

Kelly characterized it as significantly more potent, when prodded for a comparison she could only reflect on when Ken caressed her pussy so vigorously she besmirched the sofa cushion. Hearing that generated a gush of liquid from my yard.

Charlie, in turn, concluded as the condom filled. Their bathed bodies, complete with fulfillment.

We'd not used rubbers. Kelly was on the pill (even though perhaps we should have been more sagacious with Ken), but Charlie preferred to be safe. Was it enough that he breached my woman? Am I now his tutor on sexually transmitted diseases?

The story had left me dizzy. I had no idea what to state, I was infuriated and aroused, both emotions stirred so enthusiastically I was distorting who I was.

"Did it make you feel bad?" I inquired.

"Certainly, not right away because I assumed we had an agreement, but afterwards." Kelly responded.

"When? Why afterwards?"

Last night, I was with Kelly in a hotel during the summer. We were supposed to have the best day of the season, but I've just found out she spent the evening with another man named Charlie. This is heartbreaking because he had her all to himself, and even now after our tryst, thoughts of their night of passion together still turn me on. It's not surprising that I'm aroused, considering her retelling of their encounter, but I knew she'd appreciate hearing the truth. As I looked at her – nude, protectively wrapped in sheets covering her ample frame – guilt overwhelmed me.

"Kelly," I whispered, "I'm sorry it's just…this is difficult for me to hear." My words were hushed, calling for an explanation but acknowledging her upset.

"I know, but why?" Her voice shook with both pain and anger as she pulled the sheets tighter around her, enclosing her crossed arms on her chest. She had every right to feel angry, as I'd given her mixed signals. As I considered how I could shed light on this dilemma, her voice confused me even more.

"Tommy, does it sound like you like it when I'm with other guys sometimes? Is that true?" she inquired with angst. My stuttering, stammering words were weak as I tried to justify my recent actions.

"Um…well…no…it was hot but, I want you to be my girlfriend. I want to have sex with you…it's just…" She listened to me as I mumbled my heartache and confusion, waiting for a clear explanation. However, my attempt to put my thoughts into words appeared feeble, hurting both of us and diminishing my image in her eyes. I sighed, trying another route.

"I think it's like watching a porno. Seeing you be sexual and stuff. That's why I like it." I admitted. Confessing felt liberating, sadly, it was my 19-year-old mind's best response. While it was an odd explanation, it simultaneously gained some of her trust back. Her wrinkled brow and pursed lips displayed perplexity, but at least she wasn't angered at me.

"Okay. We can talk about it," she answered.

After a complicated and disordered exchange, I felt relieved knowing she would not leave me. She admitted Charlie had asked her to be his girlfriend, which hurt deeply knowing she had sex with him just hours before I arrived. Regardless, she chose me – and, amazingly, she'd rejected him even though he pleaded with her. This conversation was tender and emotional. In the aftermath, I stated clearly that I wasn't comfortable with her being with other guys, but the turning me on part lingered. I apologized for the confusion; my ordeal was unlike anything I had experienced before. I returned to the porn fantasy that caused my unusual reaction, admitting my feelings.

"We didn't reach any conclusions yet." We'd both had challenging days. "If you meet up with someone and it happens, I don't want to know." I questioned. I sensed her reservations when she verified her position: "I won't do anything you don't want me to." Her soft lips comforted my mounting anxiety before answering.

"You don't have to share that now," she advised, "when you're more at ease." This statement eased my discomfort. I had strange desires on my mind, and my relationship needed wholesome communication to resolve our obstacles. My frustration caused confusion.

I was still horny, but there would be no more sex that night, thankfully, she graciously offered to give me release as I imagined Charlie's night with Kelly. While it was uncomfortable, the discharge cleared my mind. I realized I have a peculiar fantasy that entailed Kelly with other men while I watched, and I had to understand and work through this if I wanted to repair our broken trust.

As the sun rose, we both boarded our trains and headed home. We wouldn't see each other until university started again, but I felt like we had made some progress. The train journey offered me time to think about the next step. I no longer felt afraid that she would leave me; she had rejected Charlie for me. While Ken and Charlie might have more experience, I had her heart. She was the woman I wanted - only porn was the issue.

I believed that if I stopped watching it, I would clear my mind of these fantasies. However, at home, I found it harder than I expected for a 19-year-old.

On my first day back, I succumbed, thinking it was just one last time to relieve myself. The days that followed were tough. I was so full of desires that I fantasized about the nudes Kelly sent me during university, even the ones she'd sent Ken, constantly reminding me of my time with him. A week later, I was really struggling, caught in a spiral of desiring Charlie and Ken's shared pleasures with her. It felt like my fantasy was becoming more prominent and compelling me to crave it more. I was worried I was moving in the wrong direction.

As the last week of summer arrived, I had developed some progress. I hadn't touched myself for an entire week. I was spending time with friends and staying busy. I realized the key was to distract myself whenever I felt aroused.

However, one night, Kelly texted me.

Kelly: Are you still awake?

Me: Yes, what's up?

Kelly: I'm out right now. Charlie is being flirty. You didn't answer me when I asked if you were okay with me fooling around. So now, I'm wondering if you've changed your mind?

I couldn't believe what I was reading. After all my attempts to overcome my urges, here she was, asking me for permission. I thought I had escaped this, and that I was stronger for quitting porn. But my lust overwhelmed me in that moment.

Me: I don't know, it doesn't feel the same when I'm not there.

I should have said, 'go ahead, but I don't want to know,' but I couldn't.

Kelly: Well, I can send you something? Maybe a video? ;)

My rational thoughts disappeared as my heartbeat intensified. I kept rereading the message, overwhelmed by my arousal.

Me: Fuck, okay, but just this once! After all, you're my girl.

What I didn't realize at the time was that when Kelly asked me if she could fuck Charlie, if I didn't want it then she wouldn't, but she never told me what SHE wanted.

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