Celebrity Sex Stories

Cass is known for her street style sense.

An initial blunder led to secretive and uninhibited intimacy.

Spankmasters
May 10, 2024
12 min read
cheatingoutdoorpenetrationerectiontouchingfingeringwetillicitintimatearousalCass
Cass
Cass

Cass is known for her street style sense.

Cass was a vivacious person. She wasn't pretentious - she showed her true self to the world. She was a confident communicator, certain of who she was and what she thought. She lived with her father in a one-story house on the opposite side of town. The attic had been transformed into two rooms. Up a small wooden staircase from a room with a piano in it, the first room had a double bed in it with a door leading to Cass's room. Downstairs, there were various rooms off a central hallway.

Cass's mother lived elsewhere, as she had split from her father several years earlier. Her father was a reserved person. When at home, he typically watched TV or read, with a cigarette in hand. Cass's mother, whom I never met, was described by Cass as overbearing and annoying.

Cass often wasn't home on Saturday afternoons because she was attending singing lessons and occasionally participating in amateur dramatics. Cass had a pleasant singing voice, and her singing was important to her. However, I often got the feeling that she had been pushed to achieve this level early on.

My relationship with Cass was intricate. It started when we met at a church gathering. She took an interest in me and, displaying some of her mother's tendencies, encouraged us to find a secluded spot. By the end of an hour of lightly disjointed conversation and brief exits from the building, she had kissed me, I had responded, and we had seemingly become a couple. Those kisses weren't shy, either. She demonstrated that she wasn't playing around as her tongue danced with mine during those initial covert encounters.

Our connection, though, was more of a muddled and unsettled situation. At the time, we were both members of church groups. I was still a virgin and happy to accept whatever Cass offered. In that circumstance, this entailed a deeply repressed struggle with intimacy. Passionate kissing, touching through clothes, and even some rhythmic movement while fully clothed.

It was a recipe for disaster, as we both wanted to be together but felt it would be wrong given our beliefs.

As a result, we only lasted two weeks.

If I'm being honest, I was intimidated by being around a woman in a group of girls. Perhaps it was due to the church's teachings about the evils of sex for its own sake influencing my youth so much that, despite being of legal age, I had no experience of what a genuine physical relationship entailed. I'd learned more from porn magazines in some aspects.

Although Cass was only a year older than me, I believe her upbringing allowed her to move on with life. I was clueless and foolish and decided to tell her that the relationship wasn't working. We both struggled with the church's teachings vs. sex issue but I wasn't mature enough to discuss it with Cass. I felt out of my depth. As usual for a man.

The day we broke up was tough because, after I told her, she broke down on the sofa in tears, telling me that she had been looking forward to meeting me for a while and was very excited when the opportunity arose.

This was hard for me to believe, given that at the time, I wasn't particularly fashionable or attractive - I had shoulder-length hair, aviator-style glasses, and was essentially a slender beanpole who played a little guitar.

It was on that day that I began smoking, possibly in an attempt to alleviate the intense emotional distress I was experiencing. I'd previously disregarded the fact that many of my friends smoked, but that's when I gave in.

I'd never made someone cry so much. It was an emotionally charged situation for both of us.

Following our separation, I distanced myself from Cass for a while. I didn't realize how she had built herself up, despite her apparent confidence, to put herself in front of me that first night we kissed. I understood that, despite my emotional immaturity, I shouldn't rub it in by hanging around.

Not long after our split, Cass stopped attending church. It was approximately a year later when I randomly encountered her in the town center. I was apprehensive about her reaction but, in her usual straightforward manner, she was conversant and friendly. She had begun dating someone I knew well - David.

Given that I had essentially ended a relationship with her, I didn't have the right to pass judgment on whom she chose to date next. David was an odd choice, though - he was exceptionally laid-back to the point of being nearly asleep at times. Cass and David were a couple now, and, upon her invitation, ten days later, I found myself at Cass's home for the first time since our separation, with David and a few friends.

All of us were low on money. I had just started my first job and barely managed to sustain my vehicle and pay some rent to my parents. One sunny, early Saturday evening was spent downstairs at Cass's house with the patio doors open, overlooking the long, sparse garden of her place, which led to fields behind. Nowadays, these fields probably have houses built on them, but back then, it was a pleasant landscape to gaze at.

Joined by a regular cigarette for me, and a glass of Cinzano & Lemonade (the only affordable alcohol that we who drank could tolerate), the evening was quite mellow, and a considerable amount of time passed chatting and chuckling.

As the night progressed, and the sun sank, several friends left, leaving Cass, David, and me. Cass and I were enjoying ourselves immensely - we had a lot to discuss. David participated in the conversations with his usual laid-back nature. There was no awkwardness.

Cass appeared pleased with David, and it was gratifying to see her so cheerful. Amongst everyone I knew, she was the epitome of "full of life" and her contentment was delightful to witness. Cass and I were so engrossed in talking that David almost had to signal his desire to speak. We had a friendly banter rhythm that we'd never possessed before.

I was conscious that Cass and David were sleeping together. A friend had casually mentioned this in a conversation a few days prior when I stated I was going over to see her.

But Cass wasn't in the church anymore, so it was her call, and I'm confident she had plenty to offer. I suspect for her, the beginning of her relationship with David marked the ending of her participation in the church and, in consequence, she became the subject of speculation and gossip about her romance from former acquaintances - not that she bothered with their opinion.

I was still a virgin. I had several female friends but preferred their company. However, I was often labeled a "lovely guy," which, despite the odd illicit encounter that sometimes led to kissing and closeness, meant I had never seriously considered anything more.

Cass was an attractively styled woman, coupled with that staunch personality. She had long hair, often tied back at the nape of her neck, revealing a face with inquisitive eyes. Her nose had a slightly protruding bridge, giving her a recognizable profile, and she typically had a natural expression that revealed a smile waiting to happen.

She was only about 5'3" tall, which tended to accentuate her bust. Cass's breasts were sizable enough that she always wore substantial bras, as without them, her back muscles would ache. Her body had a shapely waist that harmonized with her legs, which were usually wearing leggings or tracksuit pants. If she wore a dress, it would be just above knee-length, with a neck cut that showcased her bust without being overly tight.

She had a distinct sense of style and once told me that her shape made it challenging to find clothing that suited her well, so when she found a dress that fit, she'd purchase a couple. In a dress, Cass's bare legs would be adorned with fairly high-heeled court shoes. As I'd mentioned earlier, she was a woman amongst women. She TRULY was a woman amongst women.

Returning to that specific evening. The day had been unexpectedly warm. Cass was still wearing the dress from her morning music sessions at school. The other chums who hung around that evening had dispersed. With everyone else away, Cass proposed that the three of us--Cass, David, and me--should watch a movie. Since we lived in the video era before DVDs, this entailed either setting the timer for recordings or sitting through the broadcast.

We'd all indulged in a few of the well-known Cinzanos during the course of the evening. I got an additional round of them (which I'd somewhat diluted with a few gulps of water throughout the night). Cass collected a blanket to cover us on the sofa and we settled in to watch the movie she wanted to catch.

After about fifteen minutes, Cass placed her hand on my thigh. Taking into account that this was the first time I'd been at her house since our breakup, this came as a surprise; I hadn't anticipated even the slightest physical contact. Thankfully, her hand was moving - very gently, kneading my thigh and then, with a more determined motion, maneuvering her hand to lie across my lower abdomen.

While sitting close to Cass on her left side, I started feeling aroused due to her touch on my right. It was both surprising and pleasurable for me. I hadn't expected this level of intimacy from her, especially after spending the evening believ­­­­[evil][/the evening considering her attractiveness.][/

Cass continued to rub my thigh sensuously, causing my erection to become more pronounced. She understood the impact of her actions and intentionally provoked me further. Although confused, I couldn't help but enjoy her advances. Meanwhile, David sat on the other side of Cass, unaware of the intimate exchange. Although I had no interest in disrupting their relationship, I found it challenging to navigate the situation.

As Cass's touches began to arouse me, I decided to respond. I placed a hand on her thigh, instantly feeling her leg move away. Determined to continue, I began a slow, circular motion with my hand on her thigh. Cass's grip on my leg tightened, signaling encouragement.

Moving up her leg, I wrapped my fingers around her skirt, attempting to lift it, but not wanting to appear too obvious. Her hand on my thigh pushed harder, indicating her desire for more intimacy. This unspoken conversation intrigued me. Our movements were subtle but purposeful.

I managed to lift a small portion of her skirt, revealing her bare leg. Sensing her obvious arousal, I traced my hand along her thigh, near her groin area. After moving to a more private spot, my hand slid along her leg, slowly revealing more intimate places than we had explored before.

Her grip on my leg grew heavier, causing my erection to become even harder. The blanket covered us, allowing us to touch without arousing David's curiosity. The slow, deliberate pace of our movements intensified the pleasure.

This exchange lasted for around 30 minutes. I feared revealing our contact with each other through our physical responses and movements. Therefore, I quickly withdrew my hand and retrieved more drinks.

The dim light from the TV made it difficult for David to notice my aroused state, allowing me to hide my erection under my jeans. Back with our drinks, David returned to his seat. Cass subtly placed her hand on my thigh, squeezing it gently. I returned the gesture by touching her bare thigh. However, we remained still for the rest of the movie.

I struggled to focus on the movie throughout the remainder of its duration, lost in thought about the moments we shared. I contemplated different outcomes and possible consequences, ab­­­­[aising][/worries like committing infidelity, desiring Cass, being in an unusual place, and keeping the advances from my friend David. The anticipation significantly stimulated my adrenaline.

As the movie ended, it felt appropriate for me to leave. It wasn't odd at Cas­­­­[casser's place][/to call goodbye to Cass when she wasn't in the same room and exit. I headed to the kitchen, looking through the door at Cass and David. Seizing the opportunity for a private conversation, I walked out of the front door.

"Cass, are you alright?" I asked outside.

"Yes, yes, I just needed to..."

"What did you need, Cass?"

"I need to..."

David arrived, interrupting our conversation. With the question left hanging, we all resumed our positions and finished the movie. Afterward, Cass placed her hand on my thigh once more, giving it a gentle squeeze. In response, I held her thigh.

As the movie concluded, I found myself unable to disregard the intimate exchange we had shared. I walked to my car, overwhelmed by the thoughts racing through my head. Passion, excitement, fear, unexpected desire, extramarital affairs, sex, and the charge of disco­­­­­[very][/being in an open space.

Unexpectedly, the door opened.

"Andy, wait."

"What is it, Cass?"

Cass reached out to me in her bare feet, running into the darkness. "I need to kiss you."

[and] with that, she pulled me towards her, pressing her lips against mine. It wasn't a brief kiss. Both of us held each other's faces as our tongues intertwined. My brain buzzed with a hundred unspoken emotions as I wrapped my arms around her in a natural, instinctual response. In that moment, I was unsure about the implications of what we were doing. Passion, betrayal, simple human desire, and the temptation of forbidden pleasure consumed my thoughts.

We broke the kiss, fresh air filling our lungs. Despite the cold night, we continued to hold each other.

"Hey Cass, we probably shouldn't do this."

"But I always wanted you, Cass. I couldn't resist anymore. Ignore all the crap that happened before."

"What are you trying to say?"

Cass was attempting to convey "We should have done...shared. Every time we were together, I wanted you like this."

She then did something we hadn't even considered when we were together. Her hands reached between us and rested on my hard erection. She lightly squeezed and caressed me through my jeans.

"I really wanted you...wanted this...every time we were together." She squeezed my rock-hard cock.

"Me too, Cass, but with church and everything, it didn't seem right."

"Touch me, Andy."

She kissed me again and stared at me. It felt so wrong...yet so right.

The darkness enveloped us as we continued kissing. As if to encourage me, Cass undid my belt, unbuttoned my pants, and lowered my zip. I felt her hand slide along my length and squeeze me again—only my underwear was between her and me.

I didn't hesitate. I gathered the loose material of her skirt into my hand and slid underneath it, reaching for her thigh. I could feel the seam of her underwear, the mound of her pubic hair beneath the cotton cloth. Cass gasped and then exhaled.

A whispered command in my ear. "There, Andy. There."

I had never experienced this before, but the feel of her underwear told me that she was warm and aroused. My porn magazine education (how we learned many things in the 80's) gave me a vague idea of what to do next. I slid my hand behind the elastic of her underwear, through the soft hair, and met the heat and wetness of her lips.

Cass broke away from our kiss to catch her breath and then pushed herself toward me. She whispered, "Inside."

I pushed my finger into the moist fold I felt between her legs. I could feel a burning wetness as I pushed between her labia and I could feel warmth, little folds of skin, and a natural valley that seemed to draw my finger further in.

Cass pulled away from our kiss to draw breath and then pushed herself toward me, whispering "Inside."

I pushed my finger into the moist fold I felt between her legs. I could feel a burning wetness as I pushed between her labia and I could feel warmth, little folds of skin, and a natural valley that seemed to draw my finger further in.

We kissed for what felt like an eternity. Cass's free hand explored through my hair, up and down my body, reaching my butt and holding me tightly. Her other hand on my dick squeezed and urged wetness to leak from the tip. I wondered if she'd reach inside my pants so I could feel her hold my hardness directly. Cass was moving in sync with my arousal of her.

It's unclear when we stopped, but we both seemed to know it was time to go. I said, "Oh my god. This is incredible but...I should leave, Cass."

"I wish you'd stay, Andy."

"It's not fair on David, Cass."

"I know but that was amazing. Why couldn't we have done this before?"

"Two words—the church, Cass. Let's talk about this next week. I don't want us to lose touch again."

"Okay. I'll work on it, Andy."

"Good. Let's meet again soon. Stay safe, Cass."

With one last deep, passionate but ultimately forbidden kiss, Cass went inside, and I walked home. My mind was swirling with the emotions and sensations of this secret, forbidden encounter.

I could smell Cass on me, feeling her grasping at me, closer than we ever got before. I was disoriented. Should I even be desiring my ex? The sensible part of my brain couldn't process what had just happened. In isolation, it was magnificent. I loved the sensation of touching and intimacy with her. Earth-shattering.

Our initial relationship ended abruptly, but these intense moments revealed that the spark between us hadn't vanished.

Cass's relationship with David was an imbalanced and strained affair throughout its duration. I, along with others, would be there to help her later. David was quiet but his obliviousness to what had happened became clear as it frequently occurred.

Cass and I spoke on the phone shortly after that night and we both knew it was beautiful but wrong given the circumstances. Cass confessed that David was unaware of anything that had transpired. We agreed to keep some control. Cass said she wanted me to meet her best friend. That was Eva. She said we'd get along like two houses on fire.

At the very least, I had Cass back in my life, and I was grateful for it. I couldn't quite comprehend what was happening between us. We would entwine and flirt for quite some time more.

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