She searches the internet for info

Jennifer didn't know much about anal sex. Still, she was determined to give James her ass even if she didn't like it. There were two major problems with this, though. For one, she had to convince him to have sex with her. Then, she had to figure out how to fit his big, black, cock into her virgin asshole. She decided to focus on the latter first. No point in convincing him to fuck her if she can't fit his cock inside her, right?

So, she started the same way she handled any new problem: research. The first thing she found when she searched the internet for anal sex was, of course, porn. And so much of it! Before long, she found interracial porn as well. Young white girls taking big, black cocks in their assholes. And they all seemed to love it! She spent a few days on her "research" and ended up masturbating a lot.

Still, she didn't find much that was informative. James would be back from his business trip tomorrow and then he'd be off the rest of the week for Christmas. She hoped during that time to have some time alone with him but she still had no idea what to do. Then, she decided to talk to her friend Vanessa about it. Vanessa was experienced with anal sex. Very experienced to hear her talk. She often had sleepovers with Vanessa so when she called her mom at work to tell her she was going over to Vanessa's, her mom didn't think anything of it. So, she called Vanessa to let her know she was coming over. The phone rang for a good while before Vanessa answered.

"...hello?" Vanessa sounded a bit strange.

"Hey V, I really need to come over and talk." Then, she heard muttering in the background.

"Okay, sure, come on over."

When she got to Vanessa's, she immediately realized what she had done. The car in front wasn't Vanessa's parents' car. It was her boyfriend Lance's. "Oops." She went inside and upstairs to Vanessa's room. Vanessa was dressed but it was obvious she had dressed in a hurry due to how wrinkled her clothes were. Lance, however, was just in his boxers and looked very annoyed.

"You two were fucking, weren't you? Sorry..."

"Well, you sounded like this was something important, so what's up?" Vanessa asked.

"I need some advice. See, I need to learn about anal sex."

With that, Lance perked up. "That is what we were doing when you interrupted us," he said. "How about I show you what it's like?"

"Down boy," Vanessa said annoyed. "If you want to finish what we started, quit thinking with your dick and behave. Anyway Jennifer, who's the lucky guy?"

"Um, wellllll. It's James, my step-father."

"That's fucking hot! So, what do you want to know?"

"See, I saw his cock and it's really big. I have no idea how something like that would fit."

"Hmmm. Lance, take off your shorts." Lance stood up and dropped his boxers, revealing his hard cock. Jennifer hadn't counted on Lance being here and didn't know where this was going. On the one hand, he was cute with his short, blond hair and athletic build and his cock was on the large end up the cocks she had experienced. On the other hand, she didn't want to lose her virginity to Vanessa's boyfriend. "Earth to Jennifer."

"Oh, sorry. What did you say?"

"I said is his cock bigger than Lance's?"

"It's thicker. Maybe longer."

"I see. The first time Lance tried to stick it in my ass didn't go so well. For one, he didn't warn me!"

"I said I was sorry!" Lance said defensively.

"I had snuck him in here to fool around. He actually eats my ass, which was amazing by the way. Then, he gets behind me and tries to stick his cock in. But with only his spit as lube, his cock wouldn't fit. That and I clinched like Hell on instinct since I didn't know what he was doing. After I whacked him upside the head for trying to fuck me without consent, I decided to give it a try. But first, I had him get some Vaseline and finger me. I needed him to loosen up my hole first. After he got two fingers up my ass, he managed to get his cock in there."

"So, what you're saying is that I need to loosen my asshole first?"

"Yeah. But if James is that much bigger than Lance, you might need more than fingers. Hold on a sec." She went under her bed and pulled out a box. Jennifer came over for a closer look as Vanessa put the box on the bed and opened it.

"What are...those?"

"Sex toys." She had an interesting collection of things like dildos and vibrators. "What? I can't sneak Lance in here every day. A girl has needs. Ah, here's just the thing." She handed Jennifer a jeweled buttplug.

"Um, what's this for?"

"It's a buttplug. You stick it up your butt. See how it starts narrow and gets wider? That's to stretch out your butthole."

"What's the jewel for?"

"To look cute. Also, that's the handle to pull it out. Now, take off your clothes."

"Take off my clothes? Why?!"

"Since you're here for the night and I fully intend of fucking Lance tonight, you're going to join us in exchange for the buttplug. Don't worry, I'm not going to let Lance fuck your ass. Your mouth and big tits are another story." Vanessa quickly stripped out of her clothes and knelt down in front of Lance. Her tits were a C cup. Not small, but no where near as big as Jennifer's double Ds.

Jennifer hesitated for a moment and considered going home. But this whole strange situation did have her turned on. She wasn't seeing anyone currently and as long as Vanessa kept her promise she could use a man's touch right then. So, she took off her clothes and joined Vanessa on the floor.

Vanessa was already sucking Lance's cock and passed it to Jennifer who immediately deep throated it. Vanessa may be the anal expert but Jennifer was the oral expert. Lance moaned and started to fuck Jennifer's face.

"Fuck! Vanessa can't take my cock so deep without gagging!" Vanessa was used to using a blowjob as foreplay but for Jennifer the blowjob was the main event so rather than try to get her boyfriend's cock back from Jennifer, she watched her in fascination. This was the first time anyone else had sucked Lance's cock. As much as he was obviously enjoying it, it was going to be the last time, too, but she still wanted to watch.

Because Lance had been fucking Vanessa for awhile before Jennifer called, it wasn't long before he shot his load into Jennifer's mouth. Jennifer likewise swallowed every drop.

"Damn girl, I'm impressed!" Vanessa said. "How is it you can't keep a boyfriend if you can suck cock like that?"

"Because eventually they want more than my mouth and I won't put out."

"Good point. Now, get in bed." Jennifer laid down on Vanessa's bed and saw the hungry look in Lance's eyes. His cock was soft, though, so when he got in bed with her, she knew that he couldn't fuck her right then. Instead, he grabbed her tits and started sucking on them. Every guy she was ever with had done the same. Everyone loved her big tits and she loved having them played with.

"Okay, that's enough," Vanessa said sounding slightly annoyed. "Time to return the favor, Lance." Jennifer didn't know what she meant until Lance moved down and started to lick her very wet pussy. She moaned loudly as Lance worked his magic. Lance and Vanessa might not have vaginal sex but her pussy still got plenty of attention from Lance. Likewise, the boyfriends Jennifer had sucked off had eaten her out, too, but most weren't as good as Lance. Her toes curled up and she ended up squeezing her thighs around his head. Lance ate her out like his life depended on it because it did. He had to make her cum before he suffocated. But soon, she let out a moan that was closer to a scream and released him.

As Jennifer lay there panting with her legs spread, Lance's cock was rock hard, again. His every instinct told him to slide in there and fuck her virgin pussy. But before he could try, Vanessa got on top of Jennifer and gave him a new target.

Jennifer found herself face to face with Vanessa with their breasts pushing together. "What are you doing?"

"Taking a bullet for yo--Ohhhhhhhh!" Vanessa's amused expression suddenly changed as her eyes rolled back into her head momentarily. Then, her smile returned but it was a look of absolute lust. Jennifer realized what was happening. Lance had put his cock in Vanessa's ass and they were having sex on top of her. If she was into girls at all, this would have been very hot and she could have made out with Vanessa while Lance fucked her. But she was straight as an arrow so this was just uncomfortable and weird.

"Um, guys? Can you let me out?"

"You're no fun."

"I disagree," Lance said as he maneuvered them off of Jennifer. They repositioned in doggystyle without him taking his cock out and then he continued to fuck Vanessa's ass. Jennifer filed away this bisexual encounter with her best friend that almost happened to be dealt with later and instead took this opportunity to get a close look at actual anal sex. Lance was really pounding away at Vanessa's ass and she seemed to be loving every second! Jennifer started to reconsider letting Lance have a good with her ass after all but suspected that Vanessa wouldn't want to share anyway. Still, she couldn't help but reach her right hand between her legs and play with her pussy while the left pinched her nipples.

Since Lance had just cum, he lasted a long time. During that time, Vanessa and Jennifer both came more than once. However, Jennifer's orgasms were the quiet ones she was used to having under the covers at night. Vanessa's orgasms were loud, more frequent, and had plenty of dirty talk in between. Finally, Lance yelled out, "I'm gonna cum!"

"Fuck! Fuck! Cum in my ass! I want to feel your hot load!" Then, he thrust all the way inside and stayed there. Jennifer moved closer and could see his cock twitch as he shot his cum inside of Vanessa. When he pulled his cock out, he was soft, again, but Vanessa's ass gaped open allowing Jennifer to see some of the cum.

"That was so hot," Jennifer said.

"Oh shit, Jennifer, I forgot you were still here."

"I didn't," Lance said. "Having her watch really turned me on."

"...yeah, you should go before you get any bright ideas, Lance," Vanessa said as she looked at Lance sternly. "Oh but first, Jennifer, bend over the bed and spread your ass."

"Um, you're sending some mixed signals here," Jennifer said as she did as she was told.

"See, this is why Lance is leaving. I can't trust that he won't try to fuck you and you're horny enough to let him. No, he's going to put the buttplug in."

"Oh, okay." She wanted to argue that she'd never fuck Vanessa's boyfriend but Vanessa was right. She was too horny to resist if Lance took advantage. But then, instead of feeling the cold tip of the metal buttplug, she felt Lance's warm tongue on her asshole causing her to gasp. Lance was eating her ass! "Fuck, that feels... I don't know. I've never felt anything like this!"

"Just relax and enjoy it. This will make getting the plug in easier." Lance's tongue in her ass was starting to feel good. Really good. But then, he stopped and she felt the plug being pushed into her ass. She tried her best to not tense up and eventually the plug was in her ass. "Now, you're going to keep it in all night. You can go, Lance." Lance put his clothes back on and left. Jennifer then became very aware that she and Vanessa were still naked and Vanessa was looking at her. "Sooo, just throwing it out here. Want to try a little girl-on-girl?"

"No, I don't."

"Fine. Put on your PJs."