Once is an Accident

NOTE: This story contains elements of cheating and unprotected sex. Don't do these things in real life, folks.

This is a stab at one of my favorite genres, accidental penetrations, so apologies if it's a little less "realistic."

###

The text popped up on my screen: "Are you ready for me? I hope you're saving up all your cum for when I see you tomorrow."

Lysa attached a video. It was taken last summer, right before we were going to be apart for months. The video started on her face, scrunched up in pleasure, then scanned down her chest, her breasts bouncing in rhythm, nipples beautifully hard. The video kept going further down, over her toned abs, to the fuzzy dusting of blonde hair on her pussy. Further down, and I could see her flowery pussy lips opening, welcoming my cock over and over with a wet sound.

Behind the camera, I could hear myself say in a low, gruff voice, "Fuck, Lysa, I'm about to cum."

"Cum inside me," Lysa moaned on the video. "Cum in me, fill up my pussy..."

On the video my cock drove deep into her, as far as it could go, then throbbed, emptying cum into her pussy. Lysa moaned off-camera. In the light of the flash, I pulled my cock from her grasping pussy, letting the cum spill out of her. As the camera tilted up, angling the shot to include not only the cum dripping from her pussy but also her heaving breasts and her face, blonde hair and eyes gazing down at me, I paused the video.

"Come on," I typed back. "That's not fair. You're making it very hard to stick to our agreement."

I'm ashamed to admit that quitting masturbation for three weeks was a harder task than I'd expected, but my girlfriend was going to be out of town for that whole time, and I'd agreed to save it for her. Lysa loved cum more than anything, and I was happy to oblige her, knowing the pent up passion would make my first time back inside her extra good.

Our junior year of college ended three weeks ago, so our whole friend group had gone down to my friend Henry's family's place in the Catskills for a vacation before starting our summer jobs. Lysa had to visit family, so she was only coming for the last chunk of the trip.

"Only 16 more hours," Lysa texted back. "I get in late tonight."

"Wake me up when you do," I texted with a flirty emoji.

"I've got a few ideas of how." She attached another picture, this one of her with two fingers buried inside her wet pussy.

"I'm blocking you," I joked. "Too much teasing, and it's only 9 A.M."

From the door of my room, I heard a knock.

"One second," I called out, before texting Lysa: "Have to go, big day of hiking ahead." I put my phone down next to me, then yelled to the door: "Come in!"

Tess stepped through the door, looking alert and chipper in athletic clothing. She took in the room, frowning.

"We've been here one night and it looks like a tornado hit your room."

My best friend from childhood, Tess grew up two streets away from me. We were even each other's first kiss when we were 12. But that was all long ago. Both of us had chosen the same college, several states away from our hometown, and remained good friends. I can't say people didn't ask about me and Tess, though. She was undeniably beautiful: big blue eyes below dark eyebrows, high cheekbones and angular features, chestnut-brown hair tied in a tight braid. And yes, I had spent my teenage years observing the changes in her body, watching as she grew into a stunning, willowy woman with a shapely ass and breasts that were on the smaller side but perfectly fit her short frame. I knew she was beautiful, but our relationship was never really romantic (not counting the first kiss), which suited us perfectly. We worked too well as friends to risk anything. Besides, she had been the one to introduce me to Lysa, and Tess was dating Henry.

"You know how I feel about putting clothes in drawers while on vacation. Besides, you don't have to share my room," I said. I stealthily tucked my semi-hard cock into my waistband and stood, brushing past her to pick up one of the shirts from the ground. Sniffing it, I put it on.

"You're horrible," Tess said with a laugh. "Anyway, I was just coming to rouse you for breakfast. Everyone else is done eating, but what else is new?"

"Should I pack a hat? It's supposed to get up to the 90s, right?"

"I don't know. Henry and Greg were saying there's a chance of rain. Can I check the weather on your phone?"

"Go for it."

Tess picked up my phone, then let out a yelp and dropped it. She blushed furiously "Holy crap, whoops! Sorry!"

"What?" I crossed to the bed and picked up my phone. Lysa had texted one last picture, this one a closeup of us having sex. The caption read: "Don't tire yourself out too much." Tess had picked up my phone only to get an eyeful of my hard cock, wet and veiny, stretching out her friend's pussy.

"Sorry, I didn't realize that would be up on my phone," I said, embarrassed. "Lysa's been... sending me stuff in preparation for her getting in tonight."

"Oh, yeah, no, I get it." Tess blushed even deeper, then paused. "I -- I only looked for a second, so I barely saw anything."

"No, of course." It was more flustered than I'd seen her in a long time. Neither of us knew what to say.

"I'll just check the weather on my own phone," Tess said, and left.

Tess came from a religious family, so her reaction wasn't unexpected. When you're raised by parents who don't even mention the existence of sex to you, it can be tough to bounce back. I'd been the one to explain sex to her, one day when we were teenagers, coming back from school. Even so, by now I figured she'd gotten over the embarrassment and shame surrounding sex, considering she was dating Henry, but she was still fairly innocent. Then again, she had just been surprised with a closeup picture of her two friends having sex, so who wouldn't be embarrassed?

I'm sure that was it, I thought as I got dressed for the hike. Regular embarrassment.

###

Despite my late start, a few cups of black coffee jolted me into alertness for the hike. Our other friends, Marina, Bo, and Sarah, were experienced hikers who were glad to drag us along at their fast pace, up trails with pine needles that covered treacherous rocks and roots. I spent most of the hike watching where I put my foot, expecting to twist an ankle any second. When I did hike without my eyes glued to the ground, I found them drawn up perfect, strong, slender legs to Tess's ass in her tight athletic shorts. She was walking ahead of me, holding hands with Henry.

I shook my head. Clearly, a mixture of Lysa's teasing and the sexual frustration of the last few weeks had turned me into a dog, slobbering over anything with the slightest female form.

We stopped for water at a clearing that looked out over the miles of trees below us. As I drank from my water bottle, Henry pulled me aside.

"Can I ask you something, man? It's about Tess."

"What's up?" I thought maybe Tess had told him about the picture she'd seen of Lysa and me and prepared to apologize.

"Tess and I have been dating for like four months now, and..." he paused, a little awkward. "I know this is weird, since you guys have been friends forever, but I'm just gonna say it: I kinda thought we'd be doing more, sexually, by now. All we've done is dry humping, nothing below the clothes."

Hearing that was surprising, but not completely unexpected. So Tess was still a virgin. I don't know how that made me feel. Part of me was bummed for my friends that they were missing out on all the great things sex had to offer, but another part of me, one I didn't realize was there, felt a flash of... something. Not surprise, but maybe lust. I tried not to show emotion on my face as he went on:

"She's said she's waiting for marriage to actually have sex, which I totally understand, but do you think she'd want to do anything more than just makeout and dry hump? Not even just for me. I'd love to make her... finish, you know."

"I haven't talked with her about it," I said truthfully. "It's not the sort of thing we discuss."

"Do you know if she's ever gone further than that with her previous boyfriends?"

"What previous boyfriends?" Tess had never dated anyone seriously before Henry. Heck, the only reason I knew she was straight in high school was that she'd talk about having crushes on boys, but when I'd tell her to do something, she'd refuse. "If I were you, dude, I'd just let her lead the way. She does what she wants, but not before she's ready."

On the way back down the mountain I watched Tess with more curiosity. It certainly explained her reaction to the picture -- she was totally inexperienced, so maybe it was more disgust at what she had seen. I felt bad for just leaving my phone open. I knew her well enough to know her reaction wouldn't be one of judgment, but it had to make her uncomfortable. I resolved to apologize when I got the chance.

By the end of the hike we were all dripping with sweat. As Tess pulled her shirt up to mop off her flushed face, I could make out the tender curve of her breasts beneath her sports bra, and, I noted with another pang somewhere in my stomach, surprisingly hard nipples. When she lowered the shirt she was looking right at me. I looked away, too late.

Damn, I thought, cursing the fact that Lysa wouldn't return for another eight or nine hours. I just needed to stop myself from getting horny for long enough not to do something stupid.

###

"Well, I'm gonna head to bed," Henry said, getting up. It was late at night and we'd put on a movie after the night of drinking had wound down. Just about everybody had drifted off from the movie and gone to sleep, save for me, Henry, and Tess, who'd seen it through to the end. We were all tired, dressed for bed.

"I'll be right there," Tess said, as Henry wandered off groggily. Then she turned to me, a small smile on her lips. "T minus two hours until Lysa gets here. Are you excited?"

"Of course. I miss her a lot."

"I mean, are you... excited?" Tess said, gesturing down at my crotch.

"Ha ha ha," I said sarcastically.

Tess sat in a comfortable recliner across from me, her legs crossed under her. Without realizing, my eyes drifted down her pajama-clad form and I saw with a start that she wasn't wearing panties under her loose pajama shorts. I could make out a dark bush and the tight cleft at the top of what seemed to be her beautiful innie pussy. Of course she wasn't shaven, I thought, my cock beginning to thicken. She'd never even had sex.

"I guess she hasn't been too far away, what with all those pictures," Tess said.

She shifted on the chair. I got an even better view of her bush, and through it her neat pussy lips.

"Yeah. I'm sorry about that. You didn't have to see that." I tore my eyes away from the faint glimpse of her pussy.

"No, I liked it," Tess said. "The wifi's terrible out here, so my porn has been taking forever to load. Easier to just get it of the two of you."

"There's plenty more where that came from," I joked.

"Is there?"

I looked at her, trying to decide whether she was bluffing. We'd both had a lot to drink, but the several hours of the movie had sobered us up. She didn't usually speak this brazenly.

"Yeah. Videos, too."

Tess's face was now as pink as mine. Was she not joking around?

"Can I see?"

"Should I airdrop them, or just email?"

Tess stood up and moved across the room to me. My heart started to beat fast. I couldn't stand up, because I was rock hard.

"Show me."

Trying not to let my hands shake, I opened my phone. I pulled up the picture she'd seen, the closeup on Lysa's pussy with my bare cock drilling into it.

"Really?" I asked.

Tess nodded. She leaned down, and I caught the soft curve of her small breast down her sleep shirt. I hesitated, then thought, Fuck it. I turned the phone to her. She drank in the picture onscreen with her eyes.

"I've already seen this one," she whispered, sending a shiver up my spine. This was bad. I was too horny. I should lock my phone and get out of here. I swiped to the next one -- the video of me and Lysa, paused with the cum trickling out of her pussy, her tits and face in the shot.

"Where are you?"

I rewound the video. The only sound in the room was the slick squishing sound of me entering Lysa, then her moaning. Tess's mouth was half-open as she watched.

"Fuck, Lysa, I'm about to cum." At that, I quickly paused the video, returning to my senses. This was too much. Too personal. Lysa wouldn't want me showing intimate videos of us to one of our best friends. And did I really want Tess to see my dick? I was more drunk than I thought. And so was she, if she allowed it.

"Sorry," I mumbled. "I shouldn't show you that."

"No, it's okay," Tess muttered. "It's hot. I have a thing for small dicks."

I looked up at her. She was grinning. We both burst into laughter.

"Oh, you motherfucker," I said, leaping up to grab her. She shrieked and tried to make an escape, but I grabbed her and tackled her, tickling her, onto the couch. We were both laughing. Only when I paused for breath did I realize what a bad idea that had been. I was still completely hard, and was only wearing my boxers.

From beneath me, Tess tickled me back, and I grabbed her arms, trying to keep her from tickling me.

The rest of it happened fast. I was on top of her, hard, and somewhere in the maneuvering my cock must have slipped out of the hole in my boxers. I knew that reaching down to fix the situation would immediately make it clear to her what had happened, so I tried to keep her pinned, unable to look down. That was my undoing -- Tess spread her legs, trying to get them around me for some purchase.

All of a sudden, as she did, I felt my cock press up through the leg of her baggy shorts, against her hairy mound. She gasped in surprise, moving her lower body back, but all that did was make my cock slip down, nestling into the hot wetness between her lips. It happened so fast I didn't even think about the fact that she was dripping wet.

"Is that your --" Tess started to ask, trying to reposition herself.

Then I felt her pussy open and I slipped inside her. We both froze. I looked down. Her hairy pussy lips were stretched around my cock. I didn't have time to think about how amazing her pussy looked -- how long I'd wondered what it would look like, what she'd feel like. Though I was only a few inches into her, it was almost too much for me.

"You're... inside me." Her voice quavered.

It happened in such slow motion that the freeze-frame image of Tess below me, looking down in open-mouth surprise at her shorts pulled to the side, her wet pussy clenching my bare cock, is burned into my mind, though the moment only lasted a second or two.

"I'm sorry," I said. "I didn't mean to..."

"No, I wasn't wearing panties, it's my..." She trailed off, her breath ragged.

The moment was dreamlike. Neither of us were moving to pull apart. My cock throbbed inside her and she gasped. I felt her pussy clench. She was getting wetter, somehow. Involuntarily, I pushed an inch further into her, my cock moving on its own to bury itself as deep into her scalding hot pussy as it could.

"Wait," she said, her voice soft and strained. "Don't --" Then she was cut off by a gasp. Her body shuddered and her legs, which were still around me, pushed me deeper into her. I bottomed out in her unbelievably tight pussy. Tess was small, but she could take my whole length buried snugly inside her. She was coming, hard, trying to stifle her own moans as her pussy clenched around me.

"Fuuuuuuuck, I'm commmingggggg..." Tess whimpered.

Her body jerked, and she wrapped her arms around me, pushing our bodies fully together. Her pussy was too tight. I wasn't going to last, especially since it had been three weeks with no sex or masturbation. I was bare inside of her, and if she didn't even trim her pussy, what were the chances she used birth control? I couldn't cum in her. With the last ounce of my willpower, I tried to pull out.

"Tess, I'm gonna --"

I only made it halfway. Tess, who was still shuddering in orgasm, firmly pulled me back into her. That feeling of sliding the rest of my length back into her tight, tiny pussy was the end of it. I felt my cock swelling up, before I came hard, deep inside her.

As my cock jerked, shooting cum against the back walls of her pussy, her eyes snapped open. She could feel my warmth splashing into her. "No, no, I'm not -- oooohhhhhh --" She writhed in orgasm again, while I emptied three weeks' worth of cum into her. Any thought of trying to pull out was forgotten. All I wanted to do was bury into her and fill her up. I came and came. Each jerk of my cock within her drew another small "Ooh" from her. Her pussy squeezed me tighter than any I'd experienced.

"Oh my goddd...." she moaned softly. I slumped down on top of her, breathing heavily into her neck. We stayed like that for a while, until the last jerks of my cock and the last of her small shudders subsided, indicating that we'd ridden out our climaxes.

I lifted my head to look down at her. She was beautiful -- blue eyes wide, cheeks flushed, her hair a mess on her sweaty forehead. Through her white sleep shirt, I could see the outlines of her areolae and the tiny tents of her nipples. We looked at each other for a long moment, faces close together, then she shook her head in wonder.

"I can't believe that just happened." Tess looked down at the place where my cock was still buried inside her. Her pussy was overflowing with my white cum, dripping out around my cock. "You came inside me," she said, quietly.

"I'm so sorry," I said, "I didn't mean to --"

"No, I stopped you from pulling out. I... I've never cum that hard in my life. It's my fault. It was so good... I didn't want it to end."

"Me neither," I said, and she let out a small laugh. As she did, her pussy squeezed me, milking another drop of cum from me.

I breathed out and lifted myself up, pulling my cock out of Tess with a soft squishing noise. Even after such a hard pounding, her pussy lips were tight and perfect. My cum trickled out from between them, and she reached down to catch it on her fingers. "Wow."

"I'm sorry."

"Do you always... cum this much? How does Lysa take it all?"

My insides twisted at the mention of Lysa. "Oh, god --"

"Don't feel bad. It was an accident." Tess was still on her back, legs spread, looking up at me, not making any effort to cover her small, hairy, freshly fucked pussy. It was a beautiful sight.

"Yeah," I said. "An accident."

"No need to explain to either Lysa or Henry why you took your best girl friend's virginity and pumped her pussy full of cum, especially when it wasn't on purpose."

"Jesus, Tess." In the rush of sensations, I'd forgotten. "I just took your virginity."

She finally stood, barely coming up to my collarbone. I couldn't read her expression. Then she pulled off her shirt, revealing beautifully round, petite breasts that sat high on her chest, with dark nipples that looked big on her small tits. She then slid down her shorts, exposing her pussy in all its glory. A line of my cum ran out of her and down her legs.

"I'm going to need to shower." She looked so serious. I couldn't tell if she was angry, confused, sad -- I was horrified to think I'd just ruined one of my longest friendships.

"Tess, I --"

"Come join me."

She took a step toward me, then threw her arms around me. I hugged her back. I could feel my cock, which in my dazed state I hadn't tucked back into my boxers, pressing into her pubic mound. I was still wet with our combined juices. Tess looked up at me. Tentatively, as if we hadn't just fucked, I leaned in to kiss her. Our lips met in a spark of passion, our tongues probing hungrily for each other. Finally we broke apart.