Avoiding Entanglements

The usual disclaimers apply, all characters are over 18, they're completely fictional, and my writing style is amateurish at best. Please enjoy this story.

***

Clarissa's family had faced a lot of challenges over the years, starting a week after she was born. That was when her father died, leaving his wife with three kids and only enough life insurance money to bury him. The oldest child, Wendy, pitched in to help take care of her younger siblings, and their Mom was able to get enough work to support them.

When Clarissa was ten years old her Mom remarried, to a kind and loving man named Jake. Life improved for all of them with Jake around. Better income, a decent and dedicated father figure, and a happier mother.

Clarissa finished High School in June, and turned 18 two days later. Her family threw her a big party, to celebrate both events at once. Late that evening, after the party was over, Wendy knocked on her bedroom door.

"Hi Clari, can I come in?"

"Sure."

"Hey sweetie, so how does it feel to be an adult now, huh?"

"Same, I guess."

"I have another present for you, but this one comes with a story." She'd already given her baby sister a gift at the party. Clarissa wondered what was up.

"A story? Okay."

"Right. So. You're heading to university in September, and I wanted to make sure you succeed. Unlike me."

"But you did fine, you got your degree and everything."

"Oh honey, no, it took me six years to finish a three year program."

Clarissa gave her sister a puzzled look.

"Yeah, well, when I started university everyone else was heading into adulthood, filled with the idea that they're able to make choices and do things and be responsible. Me, I was finally free NOT to be an adult for once. I could let it all go, and be irresponsible."

"But you were always the dependable one!" Clarissa said.

"Yes, I know. You don't remember Dad, but I do. I don't think Dale does either. Mom had to work two jobs after Dad died and it was up to me to take care of you two. I was just a kid myself, and when you were a baby I was almost like your mom. I did everything for you two. Cooking, cleaning, diapers, laundry, everything. Even after school started that fall, I still took care of you guys every afternoon when I got home."

Clarissa had started to cry silently.

"Oh sweetie, don't cry. I love you both. We're family, and I would do it all over again if I had to. But listen, when I went off to university I quit adulting for a while. I had fun. I partied, messed around, you know. That wrecked my grades. Set me back a year. Then I met a guy, and I thought I was in love. The next two years were wrecked by that. Too much time with him, too much time ignoring school. That set me back even more. I finally got my head on straight, dumped him, and finished my degree.

"Clari listen to me. Please, do not set yourself up for the kind of failure I had. Don't go chasing after guys, don't play those games. Enjoy yourself, but don't get into a relationship at school. You're paying for this education, paying a lot for it, so don't blow it. Don't waste this opportunity. You will probably meet some guy and think you're in love, but believe me, it's just an infatuation."

"But people do fall in love, don't they?"

"Yes, but usually not the perfect forever kind of love that you mean. My gift and my advice is to take care of yourself and don't set yourself up for heartbreak, not while you're at school. Here, this is for you."

Wendy handed Clarissa a gift-wrapped package. She tore it open and looked at the contents with a combination of shock and confusion. "Is this what I think it is?"

"It's a sex toy, a vibrator. This will keep you happy and satisfied, so you won't need to get tangled up in romance with guys."

"You're serious? You think I should just play with myself instead of dating?"

"Absolutely. This is what I switched to after ditching Derrick. Clarissa, meet 'Bob', your Battery Operated Boyfriend. Once I stopped being distracted by guys, I finished school pretty fast. Not that guys aren't great, but it's too much of a distraction."

"Um, so, how does this work? I mean like, besides the obvious."

"Nothing tricky there, it is just what it looks like. Open the box and install the batteries. That switch there turns it on, and sets the level to fast or slow"

Clarissa followed her sister's instructions and very shortly the blue penis shaped object was humming in her hand. Her eyes went wide, and she said "This is supposed to, um, fit? Like, inside me?"

"Oh honey, don't worry about that. Believe me, it'll fit. So, now you have a plastic boyfriend who won't mess with your head or hurt you or dump you, and you can satisfy all your urges but you can still concentrate on school. I know this sounds weird, but I believe in it. Be safe and be happy, OK?" Wendy hugged her little sister, got up, and left.

Clarissa shut it off and shoved her new toy under her pillow, then wondered what she was supposed to do. Finally, she grabbed her phone and texted her bff Jenn.

+J U up?+

+Hey birthday girl. Sup?+

+I need advice+

+Need help adulting some shit?"

+Oh yeah. Wendy gave me a special prezzie+

+What did you get?+

+A sex toy+

+WTF!?+

+Vibrator+

+And?+

+And I don't know what to do+

+Really? Turn it on and stick it in!+

+Ugh. I know how it works. I don't know if I should+

+YES. You should you MUST and tomorrow you will tell me everything!+

+Eeww I thought you would give me some actual advice+

+I am. Use it. And tell me everything! All deets!!+

+I can't+

+Why not?+

+Too scary+

+Not as scary as a real one+

+Oh god that is so true. But I cant. What if someone hears it?+

+Is it loud?+

+Kinda+

+Block the door with pillows like for sleepovers+

+Maybe+

+I expect a full report+

+Fine. Nite J+

+Nite C+

Clarissa washed up, brushed her teeth, and got ready for bed. She dithered a bit trying to decide if she wanted to put her PJs on yet, finally just tossing them on her bed. Two pillows jammed against the bottom of the door was their standard way of blocking the giggling and talking during sleepovers. Once they started doing that there were no more noise complaints.

Clarissa and Jenn had talked about masturbation a bit, and they'd both tried it, but not often and not very successfully. As bffs they talked about everything, even this, so of course Jenn wanted to know. Right. With the covers pulled down, and just a bedside lamp on, she inspected the toy. Then she looked at herself, her pink pussy with fine dark hair around it. Despite her sister's insistence, there was no way this thing would fit.

She grabbed her phone again, and opened a private browser window. She searched 'masturbating with a vibrator'. Most of the results were porn sites, but there was one that seemed to be more informational. There was even a slide show. No pictures, just illustrations, and the text was quite informative. Okay, enough stalling, it was time to try it.

Clarissa switched the thing to low, and the quiet hum filled the room. She looked at the door, and felt a stab of fear. Shit! Everyone would hear! It was too loud! No, the pillows worked for sleepovers, they would work now.

She had to try this. Clarissa picked up her phone and looked at the diagrams again. The phone went back on the night stand and she got ready. Legs spread, she looked at herself. There was a neat triangle of dark hair above her pussy, and more soft downy hair along the swells of her outer labia. She wasn't overly hairy down there, not like some of the girls she'd seen in the change room after gym class. Her pussy was usually just a neat dark slit down the middle of that puffy mound, unless she was aroused.

That was when things were a little different. Those dark, wrinkled inner lips would start to peek through. It didn't happen often, but when it did she thought it looked weird. And that was also when she'd get wet down there. She understood what that was all about from health class and the talk her Mom had given her about sex. When she felt wet like that in public, she felt like her pussy was bulging out and would be obvious to everyone, so she avoided thinking about sexy stuff most of the time.

She moved the humming toy down and touched the tip to her protruding inner lips. Clarissa gasped, then looked at the door, and realised she would have to be quiet too. She returned the toy to her pussy, and moved the humming thing along her slit. The dark lips seemed to flow around the tip of the toy, and they vibrated along with the muted hum. That looked positively surreal. But it felt incredible!

She stifled another gasp, and continued to move the tip of the toy slowly up and down. The vibrations went deep inside her, stirring nerve endings she didn't know she had. Her arousal increased, made her pussy wetter, and when she ran the thing over her clit on one pass she yelped at the sensation. She directed another frantic look at the door, then she moved the vibe in a slow circle around her clit. 'Oh. My. Fucking. God.' she whispered. This was better than any prior masturbation session had ever been, by far!

As she swirled the toy around the outside of her sex, her orgasm roared up and consumed her senses. Her thighs quivered, her breath came in short panting gasps, and she felt a flood of wetness in her pussy. Clarissa chased her orgasm, running the toy over her clit repeatedly, until the glorious sensations faded. She turned the vibe off and set it aside, flopping on the bed to rest for a minute. Then she inspected the results of her experiment. Those inner lips were now fully exposed, like a flower that had opened its petals. Bigger than she'd ever seen them. And she was wet, VERY wet, dripping on her sheets, in fact. She got up and grabbed a towel and laid down on that. Despite how good that orgasm was, she still hadn't done the deed yet. There was still more to try. More inside.

She'd never had a serious boyfriend, and was still a virgin. which made her understandably wary of putting this huge thing inside her pussy. The toy was over 7 inches long, and big enough to fill her fist. Even though she understood how sex worked, the idea that this would go in there was still a little scary. Clarissa got herself comfortable again, and switched on the toy. One again, she started by touching her labia and clit, as she worked herself closer to the next step.

She was certain that she was wet enough, and ready enough, so she changed her grip on the vibe and pressed the tip into her opening. Just a bit, just to see how it felt. The vibrations were amazing, it felt better than anything! She pressed it a little further in, and the stimulation made her groan softly. It felt so good, so incredible, as she held the tip of the vibrator inside her pussy. The fullness from the intruding head, the stretched out feeling of her vagina, these were new, amazing, and unique feelings. Her head lolled back as her thighs and stomach muscles clenched as she came again. Desperate not to cry out, she clamped her eyes and mouth shut, concentrating on the amazing sensations coming from her spasming pussy.

Waves of rapture flowed over her, all pouring out from that amazing, quivering, sodden receptacle between her legs. Any orgasm before this was forgotten, discounted by the power of what was coursing through her nerves right then and there. On and on it went, and she thrilled with with ecstasy of it. When she finally came down off her orgasmic high, she was sweating and dizzy, lying limp on the bed. The vibe was buried deep in her pussy, all the way, with just the base protruding, humming away to the bland little tune that had caused all this. She had no idea how it got shoved all the way inside her, but there it was. It did fit! And wow, the incredible stretched feeling from that thing inside her was awesome. She could feel her inner muscles working against the intruder deep inside her, seemingly trying to push it out and suck it in deeper at the same time.

She pulled it clumsily out of her sopping wet pussy and turned it off. Wow. That was absolutely fucking amazing. Was that what sex was all about? No fucking wonder her sister had almost failed out of university over this. She looked down at herself, and saw that her inner labia were even bigger and wetter than earlier. They were almost like butterfly wings now. Clarissa was suddenly overcome with drowsiness. She shoved the vibe under her pillow and pulled up her covers, asleep in minutes.

---

She awoke the next morning feeling a little bit sore between her legs. That was probably to be expected, being her first time and all. She put her PJ's on, and found the towel she'd put on the bed last night. It was stained a bit but there was no blood. That was odd, wasn't she supposed to bleed the first time? Maybe the vibe wasn't the same as a real penis? She put her pillows back on the bed, wrapped the toy in the towel and went to take her shower. She washed the toy off but didn't try using it again. Not yet. But it was tempting, as the noise of the shower would drown out the humming.

After she finished in the shower, Clarissa went back to her room and got dressed. Then she took out her phone and searched online for 'first time' advice and discovered that some girls don't bleed when they lose their virginity. Sports or active lifestyle or just plain luck might mean there was no hymen to break. She recalled now that they'd been told all this in health class. She wondered if technically she was still a virgin now or not.

Her phone pinged with an oncoming text.

+good morning sunshine!+

+Hi J+

+Spill. How did it go last nite?+

+Awesome+

+Details!+

+The big O is bigger than I thought+

+Really?+

+OMG yes!+

+Better than before?+

+No comparison+

+Did it hurt the first time?+

+No it was fine. No pain no blood+

+How big is it?+

+Hang on+

Clarissa rummaged on her desk for a ruler, then checked the vibrator.

+18 cm and 5 cm thick+

+Holy fuck. You took that your first time?+

+Yah, things just kind of escalated and suddenly it was all in+

+Wow+

Her phone started ringing, it was Jenn.

"Hey!"

"So it was good?"

"Yeah, soooo good. Not like before, like with my fingers."

"Really, wow, so you're okay and everything? Not walking funny?"

"I'm a little sore, but it's fine."

"You gonna use it again?"

"Oh god, yes. Every chance I get. It's awesome!"

"Send me pix."

"What? Ewww, no!"

"No, dummy, pix of your toy. JUST the toy, please. I don't need to see any more than that!"

"Okay, okay."

"Oh hey, I was gonna ask if you want to come up the the cottage for Canada Day this weekend. We'll going up Thursday night and stay till Sunday. When does your job start?"

"I don't start till Monday the 5th, so I can go. Oh, wait, Wendy is here this week. Mom and Jake might want to do some family stuff while she's around. I'll call you back after breakfast, okay?"

"Okay, bye Clari."

"Bye!"

Clarissa went down for breakfast and asked if she could go to Jenn's cottage for the weekend, or were there plans with Wendy being home?

"I was gonna go back tomorrow but I changed my mind and I'm leaving today after lunch" Wendy said.

"Will you be back in time to start work?" Jake asked.

"Yeah, Jenn said they'd be back Sunday night, so no problem."

"Jake and I will probably just hang out here with Dale, unless you got plans too, young man?"

"Nothing so far Mom."

"Go have fun this weekend, because once you start work you'll probably be stuck at that all summer without a break." her stepdad told her.

After breakfast Clarissa went upstairs to brush her teeth and then laid down on her bed to call Jenn.

"C! Any news? Can you come?"

"Yup, all good. You guys gonna pick me up?" That was the usual deal, Jenn's Dad would swing by on their way out of town to pick Clarissa up.

"Sure thing!"

"Cool."

"Hey, Clari?"

"Yeah?"

Jenn's voice dropped to a whisper "Can you bring it with you?"

"What?"

"It. Your new toy."

"My toy? Uh, yeah, I guess. Why?"

"I wanna see it."

"'See' it?" Clarissa asked leadingly.

"Maybe try it?"

"Oh, you naughty girl!"

"You should talk! You're the one with the sex toy, babe. That's pretty naughty yourself."

"Okay fine, I'll bring it."

---

Clarissa was thinking about the trip to Jenn's cottage, and how Jennifer wanted to maybe try Clari's new 'toy'. She decided to get her friend a 'graduation' present. She did a little web surfing to see if she could order one for Jenn, that way she'd have her very own. There wasn't much time, so she paid extra for fast delivery. She just hoped her family didn't see the package when it arrived.

Clari was watchful over the next couple of days, and when she heard the noise of the delivery van pulling up outside, she was quick to get to the door. It was a plain brown cardboard box, and the label didn't say anything stupid like "Sex Toy" in big red letters like she'd feared. She took the box upstairs and pulled out the new toy and gift wrapped it for Jenn. She was gonna be so surprised!

---

Everything was packed the next day, so Clarissa was ready to go when her brother called upstairs that Jennifer was there. When she lugged her bag downstairs, Jenn gave her a hug and whispered "Got it?".

"Uh huh" she replied, and they both smiled. Clarissa felt a surge of nervous energy course through her, because there was more packed in there than Jenn expected.

They arrived at the cottage at about 8:30 that night. Clarissa had been here many times before. It was a rustic little place, with two loft bedrooms. Downstairs had great room with a fireplace at one end and the kitchen at the other. Kind of rustic but comfortable. There was only one bathroom, which was downstairs off the great room. A garage, woodshed, outhouse, and dock made up the rest of the property. There was a small sailboat moored, and a canoe sitting under the eaves of the garage. The lake was long and moderately broad, with lots of little islands and bays. Perfect for exploring by canoe.

Jenn had a double bed in her room, and the two of them always shared it when Clarissa stayed over. She'd spent many weekends and holidays up here with her BFF, ever since they were like 5 years old. They'd met in Kindergarten and had been inseparable ever since. The girls dumped their bags in the room and Jenn said "I think Dad's gonna start a fire. We can make s'mores."

The evening was spent around the fire pit, talking, laughing, and eating junk food. This was punctuated by the sound of people swatting mosquitos and the loons crying out across the lake. Jenn's parents asked them what their plans were for the first, and they said they were spend the day swimming and paddling.

The girls went to bed the same time as Jenn's Mom, leaving her Dad to take care of the fire and the minimal cleanup. Jenn asked about Clari's toy in a whispered conversation. Sound carried easily through the cottage, as it wasn't well insulated, so they couldn't get it out until her parents were gone. Sleep was a long time coming for both of them that night.

***

After breakfast they decided to take out the canoe. They'd learned to wear swim suits when paddling, because when it got hot they'd just jump out for a swim to cool off. Getting back in the boat was a bit of an acrobatic trick, but they'd both mastered that when they were little kids.

Jenn stripped and donned a fairly conservative one piece suit. She blushed a little as she did this, because suddenly the idea of masturbating in front of Clari made her nervous about being naked with her. Clarissa disrobed and put on her bikini. Jenn felt a surge of tingling in her pussy as she watched Clarissa change. She was excited about using her toy. But when? So far no good opportunity had presented itself.