angelas-first
FIRST TIME SEX STORIES

Angelas First

Angelas First

by harlyquinn69
20 min read
3.98 (8600 views)
adultfiction

It was 2009, move-in day at a small Christian college. Angela was a curvy 18-year-old with what she proudly described as "mid-sized, right-sized" breasts. Her parents weren't overly strict--trusting her for good reason. She was, after all, the quintessential "good girl." Well, except for that one time, one encounter with a boy when she was 18.

She didn't know what else to call it but "an encounter." It was after homecoming, and somehow she'd ended up alone with her high school "friend," who was also 18, in the back of a van his buddy had lent them. Her parents thought she was under the watchful eye of a school chaperone. She liked him, she trusted him, and after two years of knowing him, she thought, Why not?

But being with a boy in that way was a no-no. No, no, no, no.

He was kind, understanding, and just as awkward as she was, which made the whole thing unexpectedly special. But Angela had her boundaries. Bra and panties stayed on. No penetration. And to his credit, he was gracious, even fumbling in the most innocent ways. No need for a condom; he came in his shorts after a bit of light petting. Angela touched it--that thing. It reminded her of one of those water-filled novelty toys with a hard center.

For his part, he'd stroked her in all the right places. She'd inadvertently masturbated a few times before falling asleep at night but hadn't sought it out intentionally. Yet, his touch was different. Sweet. Fumbling fingers made their way under her panties, clumsily rubbing in circles. When she cried out in an unexpected orgasm, shaking slightly, it startled them both.

Afterward, there was the near-miss of getting caught and the quiet, mutual decision the next day: they'd wait for marriage. Those feelings were too strong and too risky, and neither of them wanted kids just yet.

Dana, on the other hand, was a wild card--hyper and full of energy, ADHD to the core. Her boundless energy made her a star on the soccer field. At barely five feet, she was one of the smallest but also one of the fastest, sharpest, and most aggressive defenders on her team. She didn't need to run opponents down--they couldn't get past her. Her scholarship had landed her at this small Christian college.

Dana had been with boyfriends before, all 18 or older. It wasn't like she'd waited for prom night to lose her virginity. High school boys and their hormones had been... underwhelming. Her last boyfriend--the one she fondly called "The Ex"--had been different. Their breakup hadn't been about fighting. It was college, distance, and the inevitability of change. But before it ended, they'd had one final, spectacular night together--arguably the best sex either had ever had. The next morning, they'd said mean things, and it was over.

Things unfolded as they do when two girls have to share the same small space. Angela wasn't shy, but as an only child with a bedroom all to herself, she wasn't used to worrying about being seen. Late nights in just a nightgown, or quick naked dashes in and out of the bathroom after a shower, had been her normal. That normal evaporated the first time Dana walked in unexpectedly.

Angela's mad dash for cover was met with laughter, and an hour later, they'd smoothed it over. After that, Angela stopped worrying about the "Bouncing Ta Ta nightgown." as Dana called it As for Dana, she had, as she put it, a "banging little body" and didn't mind showing it. Her perky little B-cups seemed to have a permanent VIP pass to the room. If she wanted to sit topless at the shared computer, Angela would just have to deal.

It wasn't long before they started talking about boys. Dana admitted she had a bit of experience but only one truly memorable night, with The Ex. Angela shared her story of sweetness in the back of the van and her decision to wait for marriage.

Bedtime, however, was where things diverged. Angela was the scholar, often up late studying. Dana had to be up early for practice, which meant Angela had to be quiet after dark.

It was during one of these late nights that Angela first heard the buzzing. Followed by a soft sigh of satisfaction. Then deep, steady breathing as Dana drifted into sleep.

Dana, it seemed, had brought her toys. And if she didn't want to share, well, Angela wasn't about to ask.

It was only the first quarter. The paper wouldn't write itself.

The first few weeks went by, and things were smooth--until he showed up. Chester was a sophomore and part of the boys' soccer team. For some reason, he started hanging out with Angela and Dana at lunch and dinner. Dana and Chester would be all chummy during meals, chatting and laughing, but by the end, he'd simply get up and leave.

Angela didn't think much of it. Nor did she think much about Dana's new habit of "going for a walk by myself to clear my head." She figured it was just Dana being Dana. After all, this small college didn't forbid boyfriends and girlfriends for the general student body, though they did frown on athletes getting "too friendly with the opposite sex" during the season. The unwritten rules were clear: "There is a time and place for fraternizing. School is for studying, and the rest of your time should be spent on soccer or swimming or whatever sport you earned your scholarship for."

So when Chester started making moves on Angela when Dana wasn't around, she was caught a little off guard--but flattered. He was nice on the eyes. Sure, his chest wasn't that broad, but that butt. Why did she like looking at that butt? And why did her eyes keep wandering to check if he was bulging on the other side of his pants? She couldn't help herself.

Seven weeks into the school year and two weeks into what she could only call a "courtship," she let him kiss her. He asked very politely, and she said yes. The next week, in his dorm room, they went to a place she'd been before with her "friend" back home--except this time, the boy was a man. A college man. He was completely naked and very much ready for action.

Chester was polite, though, always asking before he moved his hand. When she spelled it out--no penetration, no condom, and no, the panties stayed on--he didn't argue, didn't hint, didn't ask again. He just... accepted it.

He took off her bra, and she let him. That was enough for her. Then he showed her how to stroke his cock. He asked if she'd kiss it. She said no. So they stuck with the basics: up and down, up and down, as his hand stroked her panties in time with her strokes on him.

When he spouted out the white stuff, they both started laughing. He asked her if she enjoyed it. Did she...? Did she... cum? Not wanting to hurt his feelings, she said yes.

That was on a Wednesday.

On Thursday, he asked if she was doing anything Saturday night and if she'd like to go out on a date.

The girls' soccer team had an away game that weekend, while the boys' team was at home Friday. Angela could barely keep herself from spilling the whole thing to Dana, but she held back. Chester told her his scholarship might be in jeopardy if anyone thought his grades or playing were suffering because of a girlfriend.

Girlfriend. He'd called her his girlfriend.

Angela couldn't stop smiling. Sure, they had to keep it on the down low--at least until soccer season was over--but in that moment, she didn't care.

Saturday came, and Chester managed to borrow someone's car to drive them to another town for dinner. Over the meal, he carefully hinted--almost as an afterthought--that maybe they could use the condom tonight. He was so casual about it that Angela couldn't help herself; she started giggling.

"Yes!" she said.

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Chester blinked, confused. "Yes? What do you mean, 'Yes?'"

Angela smirked. "Well, yes, I might need to protect your willy--for no glove, no love!" She giggled uncontrollably. "I mean, we wouldn't want a mistake after we let your pet snake out." The words "snake" and "mistake" set her into another fit of giggles.

Chester leaned back, trying to play it cool, but grinning despite himself. "Do you want to go swimming?" he asked, completely out of the blue.

Angela tilted her head. "Well, the school's pool is closed, and I didn't bring a swimsuit with me. I don't even think I packed one back at the dorm."

"That's fine," he said. "There's a Wally Mart next to the hotel. We can pick one up and be in the hot tub in less than an hour."

"Wait, wait, wait--what?" she stammered. "Hotel?"

With that, Chester reached into his pocket and flashed a room key card for the hotel they'd passed earlier on the way into town.

"Um, um, um... um..." Angela felt her brain short-circuiting. "Y-yes? We can go get a bathing suit and then go swimming and... and... then..."

"Yes?" Chester teased. "We can? I mean, if you like, you can help me pick out the 'bubble wrap,'" he added, trying to keep his composure.

Angela waved him off, her cheeks burning. "No, no. I'm sure whatever you get will be fine. I-I'll be getting a bikini. My parents would never let me wear a two-piece," she muttered.

And just like that, they were on their way. Angela picked out her bikini, and Chester grabbed the condoms. He paid for everything, put the condoms in the car, and then went back into the store to "help" her with the suit before they headed straight to the hotel.

It was obvious he'd thought this all through.

As soon as they got into the room, Angela made a beeline for the bathroom. "I need to, um, use the bathroom and, and, and get changed," she mumbled, shutting the door behind her.

Inside, her mind raced. We're going to... do it. I'm going to be good... It's going to be fun... I could get off and enjoy it... Slowly, she slipped out of her clothes, standing naked in front of the mirror. With one hand, she massaged a breast, and with the other, she traced down to her nether region. She was suddenly transported back to that night in the van, remembering the gentle rub of her high school "friend." Her face flushed, and she stopped.

Chester was just outside.

Her inner monologue kicked into overdrive. Why am I hesitating? I've had a few fingers close, and that one time... but... but he's going to actually... Oh god. And what if I... No. Stop. No getting off and no getting knocked up. Just... do this. I want this. Chester may not be my husband-to-be, but if I flounder, I'll at least know what not to do when the right guy shows up.

Angela shook herself out of her thoughts. She finished slipping into the bikini, the small fabric making her feel like a little slut all on its own. Wrapping herself in a towel, she opened the bathroom door.

Chester was sitting on the bed. His eyes widened, almost bugging out of his head, but he managed to keep himself together. They walked hand-in-hand down to the hotel's indoor pool.

The pool room was surprisingly empty. When they stepped inside, a warm breeze greeted them, making Angela shiver slightly as she dipped her toes into the pool water.

"Nice," she sighed.

Then she turned toward the hot tub. She walked over, let the towel fall casually off her shoulders, and glanced back at Chester. "Are you coming?" she asked, raising an eyebrow.

Chester smirked, leaning casually against the doorframe. "Not yet," he said with a grin. "And the rubbers are still in the room."

Once in the hot tub, they were drawn together like magnets. At first, they sat side by side, but soon his hand found its way to her knee. He looked at her, his hand tentatively moving toward her pussy. Angela gave a small shake of her head--no. He nodded wordlessly, respecting her boundary, and instead moved his hand to her shoulder, then down to her tummy.

She leaned into him, her body pressing closer until she was almost on his lap. Her butt cheek brushed against his dick, teasingly close. Angela shifted a little more, just enough so that his hand came to rest on her bare stomach. She lifted her head, and they kissed--slow and neat. His hand slid upward, resting gently on her breast, and she kissed him deeper in response.

This slow, teasing rhythm continued for a few minutes. Chester never tried to go between her legs again while they were in the hot tub, but he did manage to lick one of her breasts after a particularly deep kiss. Angela couldn't help but enjoy being felt up and even licked, but the heat of the water was starting to get to her.

"Um, I need to go for a swim and cool down," she said, breaking their embrace.

Chester immediately stepped back and helped her out of the hot tub gracefully, his eyes filled with hunger as he watched her move. Angela's curves seemed to go on forever, and she didn't stop to look back at him until she was on the last step into the pool.

"Well, are you coming for some more?" she called over her shoulder.

Chester grinned, got out of the hot tub, and walked to the deep end of the pool. He cannonballed in, disappearing beneath the surface. Swimming underwater, he made his way toward her. Angela, still in the shallow end, stood in water just shy of covering her C-plus cup breasts.

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Then he did it. Chester swam right under her and put his mouth between her legs. Angela froze, feeling what must have been his tongue pressing against her suit. Before she could fully process the sensation, he surfaced, kissed her, and whispered in her ear, "May I lick your wet pussy again?"

Her response was a slight nod, and he was back under the water. This time, she spread her legs slightly, and Chester pulled her bikini bottom aside, spending his air licking at her pussy. Just as the bubbling, tingling feeling began to build inside her, he stopped.

Chester came out of the water and kissed her again, this time slipping one hand between her legs, teasing her under the water.

"Um, we need to get to that bed. Now," she said breathlessly.

Once in the room, everything became a blur. They were in swimsuits, so getting naked took only seconds. Angela barely registered the damp bed beneath them before Chester was between her legs, trying to go down on her.

"Please," she whispered, almost pleading. "Before I change my mind."

Chester wasted no time. He had the condom on so quickly that she had to ask, "Where is it?"

"Right here," he said, holding it up.

"May I?" she asked, but he was already on top of her in a simple missionary position.

At first, he went slowly, letting the condom pick up the spit and pussy juice left behind as lube. He tried to hold her gaze, but Angela had her eyes squeezed shut, her body trembling. Chester assumed it was pleasure, but Angela's thoughts were a whirlwind of confusion.

What is this? she wondered. It feels good, I guess. I feel... full? But where's the bubbly feeling? She couldn't stop herself from giggling nervously, which broke any chance of her climaxing.

Chester, however, didn't notice. He thought he was king--the great conjurer. What Angela didn't know, but Chester did, was that Dana had told him Angela was a virgin. He'd never mentioned it, but in that moment, he felt like he'd claimed a trophy.

He came hard, letting out a triumphant groan as he collapsed on top of her. Meanwhile, Angela's thoughts drifted absurdly: Missionary position? None of those missionaries I knew growing up would be doing this with me.

And just like that, it was over. Angela lay there silently while Chester got up, saying, "Um, I'm going to rinse off this pool water. Shall I shower or bathe with you?"

"No, no, you go right ahead," she heard herself say, her voice distant.

Once Chester was in the bathroom, Angela began to cry softly. The tears came slow at first, then heavier as she fell asleep in the damp, sticky bed they had made. She didn't make a sound when Chester returned, and he took her silence as pride--convinced he was so good she simply couldn't handle any more.

In the morning, Chester tried to talk to her, but Angela locked herself in the bathroom, playing refugee until it was time to leave. On the ride back to campus, they spoke only once, agreeing on one thing: Don't tell Dana.

There would be two more times Angela let him bed her..

The second time was a surprising success--one that Angela hadn't fully expected but couldn't stop thinking about afterward. Chester had coaxed her back to his dorm room with the same sweet charm he always used, playing the part of the bashful admirer. He told her she deserved better than him, which only made her want to prove that she was right to choose him, even just for now. But this time, things were different. The moment his tongue met her pussy, she realized just how different.

It was soft, almost tentative at first, like he was trying to gauge her reactions with every flick and swirl. She tensed for a moment--it was so new, so intimate--but as his tongue moved in gentle circles, her body began to relax. A slow warmth spread through her, and she found herself melting into the moment, her knees shaking as his hands gripped her thighs to keep her steady.

Chester wasn't rushing. His pace was slow, deliberate, as though he had all the time in the world to explore her. He alternated between broad, flat strokes of his tongue and tighter, more focused flicks over her clit, each movement sending electric pulses through her body. Angela couldn't help but gasp when he sucked lightly, the pressure a perfect counterpoint to the rhythm he'd built.

Her hands gripped the bedspread tightly, her breaths coming in shallow, quick bursts. Every nerve in her body felt like it was on fire, and the sensation kept building, higher and higher, until she couldn't hold it back any longer. She cried out, her thighs trembling as waves of pleasure rolled through her, one after another.

By the time Chester lifted his head, she was spent--completely undone in a way she hadn't thought possible. It wasn't just physical; it was the feeling of being cared for, of someone taking their time to focus entirely on her. And for the first time, she wasn't giggling nervously after coming. She was simply basking in the afterglow, letting herself feel all of it.

But then Chester climbed on top of her, and everything shifted. Where his tongue had been patient and attentive, his thrusts were anything but. It felt like he was drilling for oil, his movements rushed and aimless, as though speed alone would get them where they needed to be. Angela tried to meet his rhythm, but there wasn't much rhythm to follow--just a chaotic frenzy that left her feeling more bewildered than satisfied.

She wanted to tell him to slow down, to take his time, but the words wouldn't come. He looked so eager, so convinced he was doing everything right, that she didn't have the heart to stop him. Instead, she closed her eyes, trying to find her own pleasure in the moment. And while she did manage to come, it wasn't because of him--it was despite him.

By the time it was over, Angela felt more drained than fulfilled. Chester, on the other hand, looked triumphant, like he'd just conquered the world. She couldn't help but think, Does he even realize how bad this was?

By Thursday night, with Dana out of town for a soccer game, Angela was ready for round three. This time, she had a plan: give Chester a blowjob to wear him out, hoping it would help him slow down and actually make love to her.

When the time came, Chester sat on the edge of the bed, propped up against the headboard with a few pillows behind him. Angela stood nervously for a moment before stripping down, the cool air making her shiver as she knelt between his legs. He eagerly pulled himself free, his cock already hard and waiting.

"Help me learn to do it right," she said softly, glancing up at him. Her cheeks were flushed, not just from embarrassment but from excitement she didn't fully understand yet.

Chester grinned. "Just start slow. Use your hand, too. You'll do great."

Angela wrapped her fingers around his shaft hesitantly, marveling for a moment at how warm and firm it felt in her hand. She leaned forward, letting her lips brush the tip, and when Chester sighed in approval, it gave her a little more confidence. Slowly, she took him into her mouth, her tongue swirling experimentally as she adjusted to the unfamiliar sensation.

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