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."
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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.
